Novel compound, method for preparing same, precursor compound comprising same, and method for manufacturing thin film using precursor compound

Abstract

The present invention relates to a compound capable of thin film deposition and, specifically, to: a novel compound that can be applied to atomic layer deposition (ALD) or chemical vapor deposition (CVD), and has excellent reactivity, volatility, and thermal stability; a method for preparing the compound; a precursor compound comprising the compound; and a method for manufacturing a thin film using the precursor compound.

Description

A novel compound, a method for preparing the same, a precursor compound containing the same, and a method for preparing a thin film using the same

[0001] The present invention relates to a novel compound capable of thin film deposition via Atomic Layer Deposition (ALD) and Chemical Vapor Deposition (CVD), a method for preparing said compound, a precursor compound comprising said novel compound, and a method for preparing a thin film using said precursor compound.

[0002] As semiconductor devices become more highly integrated and miniaturized, it is becoming increasingly important to form metal and metal oxide thin films of uniform thickness for application in various technologies such as microelectronics, magnetic information storage, and catalysts.

[0003] Chemical Vapor Deposition (CVD) or Atomic Layer Deposition (ALD) is used to fabricate metal and metal oxide thin films. In particular, ALD enables the formation of desired thin films by sequentially injecting and removing reactive materials into a chamber, allows for easy compositional control, and can form films of uniform thickness. Furthermore, ALD offers excellent step coverage, which is advantageous for growing thin films uniformly on complex and sophisticated devices.

[0004] In order to manufacture thin films using atomic layer deposition, precursor compounds play an important role. There is a growing need to develop precursor compounds that are structurally stable and capable of forming thin films over a wide temperature range (ALD window) during the ALD / CVD process, through the design of new structures for novel precursor compounds that possess high volatility, high thermal stability, and high reactivity with various oxidizing agents, nitriding agents, or reducing agents.

[0005] To date, the development of precursor compounds using various ligands has been ongoing, and representative known ligands include halogens, alkoxides, cyclopentadienes, beta-diketonates, amides, and amidins. However, most known precursor compounds are solid compounds, or they may cause problems such as low volatility, vapor pressure, or stability, or impurity contamination during thin film deposition. Therefore, there is a need for the development of novel precursor compounds that overcome these drawbacks and enable thin film deposition with excellent step coverage.

[0006] [Prior Art Literature]

[0007] [Patent Literature]

[0008] (Patent Document 1) Republic of Korea Published Patent Application No. 10-2018-0044802

[0009] The present invention aims to provide a novel compound applicable to Atomic Layer Deposition (ALD) or Chemical Vapor Deposition (CVD) and a precursor compound containing the same.

[0010] In particular, the purpose is to provide a precursor compound that is liquid, has excellent thermal stability and volatility, possesses excellent ALD characteristics, is almost free of impurities, enables thin film deposition with excellent step coverage, and has a high vapor pressure, enabling uniform thin film deposition over a wide temperature range.

[0011] In addition, the present invention aims to provide a method for manufacturing the novel compound and a method for manufacturing a thin film using the precursor compound.

[0012] However, the problems that this invention seeks to solve are not limited to those mentioned above, and other unmentioned problems will be clearly understood by a person skilled in the art from the description below.

[0013] One aspect of the present invention provides a compound represented by the following chemical formula 1.

[0014]

[0015] [Chemical Formula 1]

[0016]

[0017]

[0018] In the above chemical formula 1,

[0019] M is Al, Ga, or In, and

[0020] R1 and R2 are each independently hydrogen or, a halogen element or, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms or, an alkoxy group or, an alkyl amine or an alkoxyalkyl, and

[0021] n is an integer from 1 to 5, and

[0022] R3 to R5 are each independently hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

[0023] Another aspect of the present invention provides a precursor comprising the above compound.

[0024] Another aspect of the present invention provides a method for manufacturing a thin film comprising the step of introducing a precursor containing the above compound into a reactor.

[0025] Another aspect of the present invention provides a method for producing a compound represented by Chemical Formula 4 by reacting a compound represented by Chemical Formula 2 below with a compound represented by Chemical Formula 3 below.

[0026]

[0027] [Chemical Formula 2]

[0028]

[0029]

[0030] [Chemical Formula 3]

[0031]

[0032]

[0033] [Chemical Formula 4]

[0034]

[0035]

[0036] In the above chemical formula 2,

[0037] M is Al, Ga, or In, and

[0038] R6 and R7 are each independently hydrogen or, a halogen element or, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms or, an alkoxy group or, an alkyl amine, and

[0039] X1 is a halogen element, and

[0040] In the above chemical formula 3,

[0041] m is an integer from 1 to 5, and

[0042] R8 to R 10 Each is independently hydrogen or, substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms, and

[0043] M1 is MgX2, Li, Na, or K, and

[0044] X2 is a halogen element, and

[0045] In the above chemical formula 4,

[0046] R 11 and R 12 Each is independently hydrogen or, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms or, an alkoxy group or, an alkyl amine or an alkoxyalkyl, and

[0047] R 13 to R 15 Each is independently hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

[0048] The novel compound according to the present invention and the precursor compound containing the novel compound have excellent reactivity, volatility, and thermal stability, are liquid, and enable uniform thin film deposition with excellent properties, thereby enabling the securing of excellent thin film properties, thickness, and step coverage.

[0049] The above properties provide a precursor suitable for atomic layer deposition and chemical vapor deposition.

[0050] FIG. 1 shows (3-methoxypropyl)dimethylgallium of Synthesis Example 1 of the present invention, measured by hydrogen nuclear magnetic resonance spectroscopy ( 1 This is a graph showing the results of analysis using H-NMR.

[0051] FIG. 2 shows (3-methoxypropyl)dimethylindium of Synthesis Example 2 of the present invention, measured by hydrogen nuclear magnetic resonance spectroscopy ( 1 This is a graph showing the results of the analysis using H-NMR.

[0052] FIG. 3 shows the tris(3-methoxypropyl)gallium of Synthesis Example 3 of the present invention by hydrogen nuclear magnetic resonance spectroscopy ( 1 This is a graph showing the results of analysis using H-NMR.

[0053] FIG. 4 shows the bis(3-methoxypropyl)gallium chloride of Synthesis Example 4 of the present invention by hydrogen nuclear magnetic resonance spectroscopy ( 1 This is a graph showing the results of analysis using H-NMR.

[0054] FIG. 5 shows hydrogen nuclear magnetic resonance spectroscopy using bis(3-methoxypropyl)(methyl)gallium of Synthesis Example 5 of the present invention ( 1 This is a graph showing the results of the analysis based on H-NMR.

[0055] FIG. 6 shows the hydrogen nuclear magnetic resonance spectroscopy ( 1 This is a graph showing the results of analysis using H-NMR.

[0056] Figures 7(a) and 7(b) are graphs showing the vapor pressure at different temperatures of (3-methoxypropyl)dimethylgallium of Synthesis Example 1 of the present invention and (3-methoxypropyl)dimethylindium of Synthesis Example 2, respectively.

[0057] Figures 8(a) and 8(b) are graphs showing the results of analyzing (3-methoxypropyl)dimethylgallium of Synthesis Example 1 of the present invention and (3-methoxypropyl)dimethylindium of Synthesis Example 2, respectively, according to thermogravimetric analysis (TGA).

[0058] Figures 9(a) and 9(b) are graphs showing the results of analyzing (3-methoxypropyl)dimethylgallium of Synthesis Example 1 of the present invention and (3-methoxypropyl)dimethylindium of Synthesis Example 2, respectively, according to Differential Scanning Calorimetry (DSC). In this case, a positive value of mW / mg indicates exothermic reaction (exo-up).

[0059] The operation and effects of the invention will be described in more detail below through specific embodiments. However, these embodiments are merely examples of the invention and do not define the scope of the invention.

[0060] Prior to this, terms and words used in this specification and claims should not be interpreted as being limited to their ordinary or dictionary meanings, but should be interpreted in a meaning and concept consistent with the technical spirit of the invention, based on the principle that the inventor can appropriately define the concept of the terms to best describe his invention.

[0061] Therefore, it should be understood that the configuration of the embodiments described in this specification is merely one of the most preferred embodiments of the present invention and does not represent all of the technical ideas of the present invention, and that various equivalents and modifications that can replace them may exist at the time of filing this application.

[0062] In this specification, singular expressions include plural expressions unless the context clearly indicates otherwise. In this specification, terms such as “comprising,” “comprising,” or “having” are intended to specify the existence of the implemented features, numbers, steps, components, or combinations thereof, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, components, or combinations thereof.

[0063] In the present specification, "a to b" and "a~b" indicating numerical ranges are defined as ≥ a and ≤ b.

[0064]

[0065] A compound according to one aspect of the present invention may be represented by the following chemical formula 1.

[0066] [Chemical Formula 1]

[0067]

[0068]

[0069]

[0070] In the above chemical formula 1,

[0071] M can be Al, Ga, or In,

[0072] R1 and R2 may each independently be hydrogen or, a halogen element or, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms or, an alkoxy group or, an alkyl amine or an alkoxyalkyl, and

[0073] n can be an integer from 1 to 5, and

[0074] R3 to R5 may each independently be hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

[0075] In one embodiment of the present invention, R1 and R2 may each independently be fluorine (F), chlorine (Cl), bromine (Br), hydrogen, methyl group, ethyl group, n-propyl group or iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, iso-pentyl group, neo-pentyl group, sec-pentyl group, tert-pentyl group, methylamine group, dimethylamine group, ethylamine group, diethylamine group, methoxyethyl, methoxypropyl, ethoxyethyl, ethoxypropyl, methoxy group or ethoxy group.

[0076] In addition, the alkyl group of the alkoxyalkyl group may be branched. For example, it may include an alkoxyalkyl group such as 3-methoxy-2-methyl-propyl or 3-ethoxy-2,2-dimethyl-propyl.

[0077] In one embodiment of the present invention, R3 to R5 may each independently be hydrogen, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a neo-pentyl group, a sec-pentyl group, a tert-pentyl group, a hexyl group, or an iso-hexyl group.

[0078] In one embodiment of the present invention, M is Al, Ga or In, R1 and R2 are methyl groups, n is 3, R3 and R4 are hydrogen, and R5 may be a methyl group.

[0079] In one embodiment of the present invention, M is Al, Ga or In, R1 and R2 are each independently a 3-methoxypropyl group, a halogen element, a methyl or dimethylamine group, n is 3, R3 and R4 are hydrogen, and R5 may be a methyl group.

[0080] Specifically, the above M is Ga, and the vapor pressure at 20°C may be 1 Torr or more, at 30°C may be 2 Torr or more, or at 40°C may be 3 Torr or more.

[0081] For example, when M is Ga, the vapor pressure of the compound at 20°C may be 1 Torr or more and 10 Torr or less, 1.5 Torr or more and 8 Torr or less, 2 Torr or more and 7 Torr or less, 2.5 Torr or more and 6 Torr or less, or 3 Torr or more and 5 Torr or less.

[0082] For example, when M is Ga, the vapor pressure of the compound at 30°C may be 2 Torr or more and 11 Torr or less, 2.5 Torr or more and 10 Torr or less, 3 Torr or more and 9 Torr or less, 3.5 Torr or more and 8 Torr or less, 4 Torr or more and 9 Torr or less, 5 Torr or more and 8.5 Torr or less, or 5.5 Torr or more and 8 Torr or less.

[0083] For example, when M is Ga, the vapor pressure of the compound at 40°C may be 3 Torr or more and 15 Torr or less, 4 Torr or more and 14 Torr or less, 5 Torr or more and 13.5 Torr or less, 6 Torr or more and 13 Torr or less, 6.5 Torr or more and 12.5 Torr or less, 7 Torr or more and 12 Torr or less, 8 Torr or more and 11.5 Torr or less, or 8.5 Torr or more and 11 Torr or less.

[0084] Specifically, the above M is In, and may have a vapor pressure of 0.3 Torr or more at 20°C, a vapor pressure of 0.6 Torr or more at 30°C, or a vapor pressure of 1.3 Torr or more at 40°C.

[0085] For example, when M is In, the vapor pressure of the compound at 20°C may be 0.3 Torr or more and 4 Torr or less, 0.4 Torr or more and 3.5 Torr or less, 0.5 Torr or more and 3 Torr or less, 0.6 Torr or more and 2.5 Torr or less, 0.65 Torr or more and 2 Torr or less, or 0.7 Torr or more and 1.5 Torr or less.

[0086] For example, when M is In, the vapor pressure of the compound at 30°C may be 0.6 Torr or more and 5 Torr or less, 0.7 Torr or more and 4.5 Torr or less, 0.8 Torr or more and 4 Torr or less, 0.9 Torr or more and 3.5 Torr or less, 1 Torr or more and 3 Torr or less, or 1.2 Torr or more and 2.5 Torr or less.

[0087] For example, when M is In, the vapor pressure of the compound at 40°C may be 1.3 Torr or more and 7 Torr or less, 1.5 Torr or more and 6 Torr or less, 1.7 Torr or more and 5.5 Torr or less, 1.9 Torr or more and 5 Torr or less, 2 Torr or more and 4.5 Torr or less, or 2.2 Torr or more and 4 Torr or less.

[0088] In one embodiment of the present invention, the compound represented by Chemical Formula 1 may be a colorless, transparent liquid at room temperature. Additionally, the compound represented by Chemical Formula 1 may have a low melting point, a high vapor pressure, and excellent volatility at low temperatures.

[0089] In one embodiment of the present invention, when the compound represented by Formula 1 contains Ga, the temperature of the half-life (T) as a result of thermogravimetric analysis 1 / 2 ) may be 65℃ or higher and 100℃ or lower, 70℃ or higher and 95℃ or lower, 75℃ or higher and 90℃ or lower, and 80℃ or higher and 85℃ or lower.

[0090] In one embodiment of the present invention, when the compound represented by Formula 1 contains Ga, the residual amount of the compound at 250°C as a result of thermogravimetric analysis may be 0.8 or more and 2.0% or less, 0.9 or more and 1.9% or less, 1.0 or more and 1.8% or less, 1.1 or more and 1.7% or less, or 1.2 or more and 1.6% or less.

[0091] In one embodiment of the present invention, when the compound represented by Formula 1 contains In, the temperature of the half-life (T) as a result of thermogravimetric analysis 1 / 2 ) may be 85°C or higher and 120°C or lower, 90°C or higher and 115°C or lower, 95°C or higher and 110°C or lower, and 97°C or higher and 105°C or lower.

[0092] In one embodiment of the present invention, when the compound represented by Formula 1 contains In, the residual amount of the compound at 250°C as a result of thermogravimetric analysis may be 0.8 or more and 2.0% or less, 0.9 or more and 1.9% or less, 1.0 or more and 1.8% or less, 1.1 or more and 1.7% or less, or 1.2 or more and 1.6% or less.

[0093] In one embodiment of the present invention, when the compound represented by Chemical Formula 1 contains Ga, the onset temperature may be 360°C or higher and 420°C or lower, 370°C or higher and 410°C or lower, 380°C or higher and 400°C or lower, 385°C or higher and 395°C or lower, or 387°C or higher and 392°C or lower as a result of thermal characteristic DSC analysis.

[0094] In one embodiment of the present invention, when the compound represented by Chemical Formula 1 contains Ga, the peak temperature of the thermal property DSC analysis result may be 380°C or higher and 440°C or lower, 390°C or higher and 430°C or lower, 410°C or higher and 425°C or lower, 412°C or higher and 423°C or lower, or 413°C or higher and 420°C or lower.

[0095] In one embodiment of the present invention, when the compound represented by Chemical Formula 1 contains In, the onset temperature may be 250°C or higher and 310°C or lower, 260°C or higher and 300°C or lower, 265°C or higher and 295°C or lower, 270°C or higher and 290°C or lower, or 275°C or higher and 285°C or lower as a result of thermal characteristic DSC analysis.

[0096] In one embodiment of the present invention, when the compound represented by Chemical Formula 1 contains In, the peak temperature of the thermal property DSC analysis result may be 280°C or higher and 370°C or lower, 290°C or higher and 360°C or lower, 300°C or higher and 350°C or lower, 310°C or higher and 345°C or lower, or 320°C or higher and 340°C or lower.

[0097]

[0098] Another aspect of the present invention is a precursor that may include a compound represented by the above chemical formula 1.

[0099] Another aspect of the present invention provides a method for manufacturing a thin film comprising the step of introducing a precursor comprising a compound represented by the above chemical formula 1 into a reactor.

[0100] In one embodiment of the present invention, the step of introducing the precursor (e.g., a precursor compound for vapor deposition or a precursor composition for vapor deposition) into a reactor (chamber) may include a step of physical adsorption, chemical adsorption, or physical and chemical adsorption.

[0101] In one embodiment of the present invention, the method for manufacturing the thin film may include both atomic layer deposition (ALD) and chemical vapor deposition (CVD).

[0102] More specifically, the above deposition method may include Metal Organic Chemical Vapor Deposition (MOCVD), Low Pressure Chemical Vapor Deposition (LPCVD), Pulsed Chemical Vapor Deposition (P-CVD), Plasma Enhanced Atomic Layer Deposition (PE-ALD), or a combination thereof.

[0103] The method for manufacturing the above thin film may preferably be atomic layer deposition, but is not limited thereto.

[0104] In atomic layer deposition (ALD), the reactants must be highly volatile, stable, and highly reactive. ALD is a method in which reaction materials are supplied separately, allowing a thin film of monolayer or less to grow through surface reactions during a single deposition cycle, and the ligands of the reaction materials adsorbed on the substrate are removed through chemical reactions with other reaction materials supplied later. When heating the precursor compounds that serve as reactants for atomic layer deposition, being in a liquid phase can be much more advantageous in terms of reaction rate and process than being in a solid phase.

[0105] In one embodiment of the present invention, the method for manufacturing the thin film may further include the step of introducing an oxidizing agent, a nitrating agent, a reducing agent, or a combination thereof into a reactor.

[0106] Specifically, a thin film can be manufactured using hydrogen (H2), water vapor (H2O), hydrogen peroxide vapor (H2O2), oxygen (O2), a mixture of oxygen and hydrogen (O2+H2), ozone (O3), nitrogen (N2), ammonia (NH3), hydrazine (N2H4), or a combination thereof as a reaction gas, but is not limited thereto.

[0107] For example, to deposit an oxide thin film, water vapor (H2O), oxygen (O2), ozone (O3), or a combination thereof can be used as a reaction gas, and to deposit a nitride thin film, nitrogen (N2), ammonia (NH3), hydrazine (N2H4), or a combination thereof can be used as a reaction gas. In addition, hydrogen (H2) can be used as a reaction gas to deposit a metal thin film.

[0108] In one embodiment of the present invention, when the method for manufacturing the thin film is atomic layer deposition (ALD), it may include a first purging step for purging the precursor from the chamber prior to the step of injecting the reaction gas, and / or a second purging step for purging by-products that do not react with or are generated by reacting with the precursor after the step of injecting the reaction gas.

[0109] In the above purging step, the movement of the precursor onto the substrate is facilitated, the inside of the reactor is maintained at a pressure suitable for deposition, and impurities present in the reactor are released to the outside. That is, a process of purging an inert gas such as argon (Ar), nitrogen (N2), or helium (He) into the reactor before and after the supply of the reaction gas may be additionally performed.

[0110] In one embodiment of the present invention, the method for manufacturing the thin film may have a precursor temperature in the range of 20°C or higher and 60°C or lower.

[0111] For example, the temperature of the precursor compound may be 22°C or higher and 55°C or lower, 24°C or higher and 50°C or lower, 25°C or higher and 45°C or lower, or 26°C or higher and 40°C or lower.

[0112] In one embodiment of the present invention, preferably, the temperature of the precursor compound may be 30°C.

[0113] If the temperature of the precursor compound is below the range of the present invention, the reaction precursor compound may not evaporate sufficiently, and if it is above the range of the present invention, the reaction precursor compound may evaporate too quickly, making it impossible to accurately control the deposition process.

[0114] In one embodiment of the present invention, the method for manufacturing the thin film may have a process temperature of 120°C or higher and 400°C or lower.

[0115] For example, the process temperature may be 130°C or higher and 360°C or lower, 140°C or higher and 350°C or lower, 150°C or higher and 340°C or lower, or 160°C or higher and 330°C or lower. Preferably, the process temperature may be 170°C or higher and 320°C or lower.

[0116] If the process temperature falls below the range of the present invention, the reaction rate is insufficient, and as the deposition rate slows down, the deposition may not be properly carried out. Additionally, the precursor compound may not diffuse sufficiently, which may lead to defects or problems with uniformity in the material and thin film, potentially causing the substrate or thin film to become unstable.

[0117] If the process temperature exceeds the range of the present invention, the reaction rate may be too fast, leading to the generation of impurities or the decomposition of precursor compounds or reaction gases, which may result in improper deposition and make it difficult to form a thin film.

[0118] In one embodiment of the present invention, when a method for manufacturing a thin film comprising the step of introducing a precursor compound into a reactor is used, a range (ALD window) in which the deposition rate is constant regardless of the process temperature may appear at 210°C or higher and 280°C or lower.

[0119] For example, the above ALD window may be 220°C or higher and 280°C or lower, 220°C or higher and 270°C or lower, 225°C or higher and 270°C or lower, 225°C or higher and 265°C or lower, or 230°C or higher and 260°C or lower.

[0120] In one embodiment of the present invention, the method for manufacturing the thin film may have a canister temperature of -20°C or higher and 110°C or lower.

[0121] For example, the canister temperature may be 0°C or higher and 105°C or lower, 10°C or higher and 100°C or lower, 15°C or higher and 95°C or lower, 20°C or higher and 90°C or lower, 25°C or higher and 80°C or lower, -10°C, 0°C, 10°C, 20°C, 30°C, 40°C, 50°C, 60°C, 70°C, 80°C, 90°C, and 100°C. The canister temperature may preferably be 30°C.

[0122] A canister is used to supply a source gas into a reaction chamber in a thin film manufacturing method. Typically, the canister vaporizes a precursor compound to generate a source gas and then supplies the source gas into the chamber.

[0123] If the canister temperature is below -20℃ or above 110℃, the uniformity of the thickness of the thin film produced through the above thin film manufacturing method may be significantly reduced. This is because, below -20℃, the supply amount of precursor compound to the chamber is insufficient, and above 110℃, it may be difficult to obtain a uniform film due to degradation by thermal energy or an excessive supply amount of precursor compound to the chamber.

[0124] In one embodiment of the present invention, the injection time of the precursor compound may be 1 second or more and 30 seconds or less, and the injection amount of the precursor compound carrier gas may be 10 sccm or more and 1,000 sccm or less.

[0125] For example, the injection time of the precursor compound may be 1 second or more and 29 seconds or less, 4 seconds or more and 27 seconds or less, 7 seconds or more and 25 seconds or less, 10 seconds or more and 23 seconds or less, 13 seconds or more and 21 seconds or less, and 15 seconds or more and 20 seconds or less.

[0126] The amount of purge gas injected in the first purge step above may be 20 sccm or more and 800 sccm or less, 40 sccm or more and 700 sccm or less, 60 sccm or more and 600 sccm or less, 80 sccm or more and 500 sccm or less, 100 sccm or more and 450 sccm or less, 150 sccm or more and 400 sccm or less, and 250 sccm or more and 350 sccm or less.

[0127] If the process is carried out exceeding or falling short of the above range, it may be difficult to form a suitable thin film. Specifically, if the injection time of the precursor compound is less than 1 second, there may be insufficient reactants required for the formation of the thin film, and a thin film of appropriate thickness may not be formed. On the other hand, if the injection time of the precursor compound exceeds 30 seconds, the composition ratio of the thin film produced may become inconsistent due to impurities caused by the residual compound after the reaction.

[0128] In addition, if the injection amount of the precursor compound carrier gas is less than 10 sccm, the residual amount of the precursor compound that is the reactant increases, which may lead to an improper reaction, and impurities may not be purged, resulting in the thin film layer being deposited unevenly.

[0129] In one embodiment of the present invention, the injection time of the reaction gas may be 1 second or more and 30 seconds or less, and the injection amount of the reaction gas may be 50 sccm or more and 3,000 sccm or less.

[0130] For example, the injection time of the reaction gas may be 2 seconds or more and 25 seconds or less, 2 seconds or more and 20 seconds or less, 3 seconds or more and 15 seconds or less, or 3 seconds or more and 10 seconds or less. Preferably, the injection time of the reaction gas may be 3 seconds or more and 7 seconds or less.

[0131] In addition, the amount of reaction gas injected may be, for example, 100 sccm or more and 2,500 sccm or less, 300 sccm or more and 2,000 sccm or less, 500 sccm or more and 1,500 sccm or less, 700 sccm or more and 1,300 sccm or less, and 900 sccm or more and 1,100 sccm or less.

[0132] In addition, if the injection amount of the reaction gas is less than 50 sccm, the residual amount of the precursor compound, which is the reactant, increases, and an improper reaction may occur, and impurities may be generated, causing the thin film layer to be deposited unevenly. On the other hand, if the injection amount of the reaction gas exceeds 3,000 sccm, impurities caused by the reaction gas compound may occur.

[0133] In one embodiment of the present invention, the purge gas injection time of the first purge step is 1 second or more and 1 minute or less, the purge gas injection time of the second purge step is 10 seconds or more and 1 minute or less, and the amount of purge gas injected in the first purge step and the second purge step may each independently be 100 sccm or more and 2,000 sccm or less.

[0134] For example, the purge gas injection time of the first purge step may be 3 seconds or more and 55 seconds or less, 6 seconds or more and 50 seconds or less, 9 seconds or more and 45 seconds or less, 12 seconds or more and 40 seconds or less, and 15 seconds or more and 35 seconds or less, and the purge gas injection time of the second purge step may be 10 seconds or more and 60 seconds or less, 20 seconds or more and 55 seconds or less, and 30 seconds or more and 50 seconds or less.

[0135] The amount of purge gas injected in the first purge step and the second purge step is, respectively, 100 sccm or more and 200 sccm or less, 100 sccm or more and 300 sccm or less, 100 sccm or more and 400 sccm or less, 100 sccm or more and 500 sccm or less, 100 sccm or more and 600 sccm or less, 100 sccm or more and 700 sccm or less, 100 sccm or more and 800 sccm or less, 100 sccm or more and 900 sccm or less, 100 sccm or more and 1,000 sccm or less, 100 sccm or more and 1,200 sccm or less, 100 sccm or more and 1,400 sccm or less, 100 sccm or more and 1,600 sccm or less, 100 sccm or more and 1,800 sccm or less, and 200 sccm or more and 1,700 sccm or less. It may be 300 sccm or more and 1,600 sccm or less, 400 sccm or more and 1,600 sccm or less, 500 sccm or more and 1,600 sccm or less, 600 sccm or more and 1,600 sccm or less, 700 sccm or more and 1,600 sccm or less, 800 sccm or more and 1,600 sccm or less, and 900 sccm or more and 1,600 sccm or less.

[0136] For example, the number of repetitions of the above cycle may be 10 or more.

[0137] For example, the number of repetitions of the above cycle may be 10 times or more, 100 times or more, 200 times or more, 500 times or more, 1,000 times or more, 5,000 times or more, 10,000 times or more, 50,000 times or more, 100,000 times or more, and 1,000,000 times or less.

[0138] If the process conditions for the reaction gas, process temperature, precursor compound, and purge gas described above are not satisfied, a thin film with excellent properties cannot be obtained.

[0139] In one embodiment of the present invention, the thin film produced by the method for producing the thin film may include an oxide film, a nitride film, a metal film, or a combination thereof.

[0140] Due to the excellent properties of the thin film produced by the present invention, the thin film deposited using the compound of the present invention is expected to be utilized as an active layer of a thin film transistor (TFT) in future display devices and can be used as a channel, etc., during the manufacture of memory semiconductors.

[0141] Another aspect of the present invention provides a method for producing a compound represented by Chemical Formula 1 by reacting a compound represented by Chemical Formula 2 below with a compound represented by Chemical Formula 3 below.

[0142] In the above reaction, tetrahydrofuran (THF), diethyl ether, hexane, or a combination thereof may be used as a solvent, but is not limited thereto.

[0143]

[0144] [Chemical Formula 2]

[0145]

[0146]

[0147] [Chemical Formula 3]

[0148]

[0149]

[0150] [Chemical Formula 4]

[0151]

[0152]

[0153] In the above chemical formula 2, M may be Al, Ga, or In, R6 and R-7 may each independently be hydrogen, a halogen element, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms, an alkoxy group, or an alkyl amine, and X1 may be a halogen element.

[0154] In the above chemical formula 3, m can be an integer from 1 to 5, and R8 to R 10 Each may independently be hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms, M1 is MgX2, Li, Na, or K, and X2 may be a halogen element.

[0155] In the above chemical formula 4, R 11 and R 12 Each may independently be hydrogen or, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms or, an alkoxy group or, an alkyl amine or an alkoxyalkyl, and R 13 to R 15 Each may independently be hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

[0156] The halogen elements of the above chemical formulas 2 and 3 may be, for example, F, Cl, or Br.

[0157] In one embodiment of the present invention, the compound produced by the above manufacturing method can be used as a precursor in an atomic layer deposition (ALD) or chemical vapor deposition (CVD) process.

[0158] In one embodiment, a compound represented by the following chemical formula 6 can be prepared by reacting the compound represented by chemical formula 4 with the compound of chemical formula 5.

[0159]

[0160] [Chemical Formula 5]

[0161]

[0162]

[0163] [Chemical Formula 6]

[0164]

[0165]

[0166] In the above chemical formulas 5 and 6, M may be Al, Ga, or In, X3 and X4 may be halogen elements, m is an integer from 1 to 5, and R 16 It may be silver, hydrogen, or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms, or an alkoxy group, or an alkyl amine, or an alkoxyalkyl, and R 17 to R 19 Each may independently be hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

[0167] In one embodiment, a compound represented by the following formula 9 can be prepared by reacting the compound represented by formula 6 with the compound of formula 7 or the compound of formula 8.

[0168]

[0169] [Chemical Formula 7]

[0170]

[0171]

[0172] [Chemical Formula 8]

[0173]

[0174]

[0175] [Chemical Formula 9]

[0176]

[0177]

[0178] In the above chemical formulas 7 to 9, M may be Al, Ga, or In, X5 may be a halogen element, m is an integer from 1 to 5, M2 is Li, Na, or K, and R 20 and R 21 Each may independently be a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms, and R 22 and R 23 Each may independently be a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms, or an alkyl amine, or an alkoxyalkyl, and R 24 to R 26 Each may independently be hydrogen or, substituted or unsubstituted linear or branched hydrocarbon groups having 1 to 6 carbon atoms.

[0179]

[0180] The present invention will be explained in more detail below through examples. However, the following examples are intended to explain the invention more specifically, and the scope of the invention is not limited by the following examples.

[0181]

[0182] [Synthesization Example 1] Synthesis of (3-Methoxypropyl)Dimethylgallium

[0183] 200 ml of tetrahydrofuran (THF) was added as a solvent to a 500 ml flask containing 88 g (0.65 mol) of dimethyl gallium chloride.

[0184] 0.65 mol of (3-methoxypropyl)magnesium chloride solution was slowly added to a dimethyl gallium chloride suspension using a dropping funnel at -78°C and stirred overnight at room temperature. The precipitate was removed from the stirred solution using a Celite filter. The filtrate was filtered under reduced pressure at 50 Torr at 20°C to remove the solvent, and then purified at 100 Torr at 110°C to obtain (3-methoxypropyl)dimethylgallium.

[0185] The synthesized (3-methoxypropyl)dimethylgallium was 84g, and the synthesis yield was 75%.

[0186] The results of the analysis of the synthesized (3-methoxypropyl)dimethylgallium by hydrogen nuclear magnetic resonance spectroscopy (1H-NMR) were as follows, and the graph of the analysis results is shown in Figure 1.

[0187]

[0188] 1H-NMR (400MHz, C6D6): δ 2.80 (t, 2H), 2.71 (s, 3H), 1.71 (m, 2H), 0.51 (t, 2H), -0.07 (s, 6H)

[0189]

[0190] [Synthesization Example 2] Synthesis of (3-Methoxypropyl)DimethylIndium

[0191] 200 ml of tetrahydrofuran (THF) was added as a solvent to a 500 ml flask containing 85 g (0.47 mol) of dimethyl indium chloride.

[0192] 0.47 mol of (3-methoxypropyl)magnesium chloride solution was slowly added to a dimethyl indium chloride suspension using a dropping funnel at -78°C and stirred overnight at room temperature. The precipitate was removed from the stirred solution using a Celite filter. The filtrate was filtered under reduced pressure at 20°C and 50 Torr to remove the solvent, and then purified at 90°C and 20 Torr to obtain (3-methoxypropyl)dimethylindium.

[0193] The synthesized (3-methoxypropyl)dimethylindium was 81 g, and the synthesis yield was 80%.

[0194] Hydrogen nuclear magnetic resonance spectroscopy of synthesized (3-methoxypropyl)dimethylindium ( 1 The analysis results based on H-NMR were as follows, and the graph of the analysis results is shown in Figure 2.

[0195]

[0196] 1 H-NMR (400 MHz, C6D6): δ 2.81 (t, 2H), 2.72 (s, 3H), 1.80 (m, 2H), 0.59 (t, 2H), -0.06 (s, 6H)

[0197]

[0198] [Synthesization Example 3] Synthesis of Tris(3-Methoxypropyl)Gallium

[0199] 1 L of diethyl ether was added to a 2 L flask containing 65 g (0.37 mol) of gallium(III) chloride.

[0200] 0.65 mol of (3-methoxypropyl)magnesium chloride solution was slowly added to a gallium(III) chloride suspension using a dropping funnel at -78°C and stirred overnight at room temperature. The precipitate was removed from the stirred solution using a Celite filter. The filtrate was filtered under reduced pressure at 0.2 Torr at 20°C to remove the solvent, and then purified at 0.2 Torr at 50°C to obtain tris(3-methoxypropyl)gallium.

[0201] The reaction for the synthesis of tris(3-methoxypropyl) gallium is shown in Chemical Reaction Scheme 1 below.

[0202]

[0203] [Chemical Equation 1]

[0204]

[0205]

[0206] The synthesized tris(3-methoxypropyl)gallium was 95g, and the synthesis yield was 90%.

[0207] The results of the analysis of synthesized tris(3-methoxypropyl)gallium by hydrogen nuclear magnetic resonance spectroscopy (1H-NMR) were as follows, and the graph of the analysis results is shown in Fig. 3.

[0208]

[0209] 1H-NMR (400 MHz, C6D6): δ 3.19 (t, 6H), 3.06 (s, 9H), 1.95 (m, 6H), 0.51 (t, 6H)

[0210]

[0211] [Synthesization Example 4] Synthesis of Bis(3-Methoxypropyl)Gallium Chloride

[0212] A tris(3-methoxypropyl)gallium solution was prepared by adding 100 ml of pentane to a flask containing 16.7 g (0.06 mol) of tris(3-methoxypropyl)gallium synthesized according to Synthesis Example 3.

[0213] In addition, a gallium(III) chloride solution was prepared by adding 50 ml of pentane to a flask containing 5 g (0.03 mol) of gallium(III) chloride.

[0214] Subsequently, the prepared gallium(III) chloride solution was slowly added to the tris(3-methoxypropyl)gallium solution prepared at -78°C using a dropping funnel, and stirred overnight at room temperature. The precipitate was removed from the stirred solution using a Celite filter. The filtrate was filtered under reduced pressure at 20°C and 0.2 Torr to remove the solvent, and then purified at 90°C and 69 mTorr to obtain bis(3-methoxypropyl)gallium chloride.

[0215] The reaction for the synthesis of bis(3-methoxypropyl) gallium chloride is shown in Chemical Reaction Scheme 2 below.

[0216]

[0217] [Chemical Equation 2]

[0218]

[0219]

[0220] The synthesized bis(3-methoxypropyl) gallium chloride was 22.6 g, and the synthesis yield was 100%.

[0221] The results of the analysis of the synthesized bis(3-methoxypropyl) gallium chloride by hydrogen nuclear magnetic resonance spectroscopy (1H-NMR) were as follows, and the graph of the analysis results is shown in Fig. 4.

[0222]

[0223] 1H-NMR (400MHz, C6D6): δ 3.08 (s, 6H), 3.02 (t, 4H), 1.74 (m, 4H), 0.66 (t, 4H)

[0224]

[0225] [Synthesization Example 5] Synthesis of Bis(3-Methoxypropyl)(Methyl)Gallium

[0226] A bis(3-methoxypropyl)gallium chloride solution was prepared by adding 100 ml of pentane to a flask containing 23 g (0.09 mol) of bis(3-methoxypropyl)gallium chloride synthesized according to Synthesis Example 4.

[0227] 0.09 mol of a methylmagnesium bromine (MeMgBr) diethyl ether solution was slowly added to a bis(3-methoxypropyl) gallium chloride solution prepared at -78°C using a dropping funnel, and the mixture was stirred overnight at room temperature. The precipitate was removed from the stirred solution using a Celite filter. The filtrate was filtered under reduced pressure at 0.2 Torr at 20°C to remove the solvent, and then purified at 65 mTorr at 45°C to obtain bis(3-methoxypropyl)(methyl)gallium.

[0228] The reaction for the synthesis of bis(3-methoxypropyl)(methyl)gallium is shown in Chemical Reaction Scheme 3 below.

[0229]

[0230] [Chemical Equation 3]

[0231]

[0232]

[0233] The synthesized bis(3-methoxypropyl)(methyl)gallium was 16.6 g, and the synthesis yield was 80%.

[0234] The results of the analysis of synthesized bis(3-methoxypropyl)(methyl)gallium by hydrogen nuclear magnetic resonance spectroscopy (1H-NMR) were as follows, and the graph of the analysis results is shown in Fig. 5.

[0235]

[0236] 1H-NMR (400MHz, C6D6): δ 3.05(t, 4H), 2.94(s, 6H), 1.91 (m, 4H), 0.54 (t,4H), -0.03(s, 3H)

[0237]

[0238] [Synthesization Example 6] Synthesis of Dimethylaminobis(3-methoxypropyl)gallium

[0239] 100 ml of pentane was added to a flask containing 2.5 M n-BuLi (0.09 mol), and 4.1 g (0.09 mol) of dimethylamine was slowly added at -78°C. After the addition of dimethylamine was completed, lithium dimethylamide (LiDMA) was synthesized by stirring for 1 hour while maintaining -78°C.

[0240] In addition, a bis(3-methoxypropyl)gallium chloride solution was prepared by adding 100 ml of pentane to a flask containing 23 g (0.09 mol) of bis(3-methoxypropyl)gallium chloride prepared according to Synthesis Example 4.

[0241] Subsequently, the synthesized lithium dimethylamide was slowly added to bis(3-methoxypropyl)gallium chloride prepared at -78°C using a dropping funnel, and the mixture was stirred overnight at room temperature. The precipitate was removed from the stirred solution using a Celite filter. The filtrate was filtered under reduced pressure at 20°C and 0.2 Torr to remove the solvent, and then purified at 100°C and 75 mTorr to obtain dimethylamino bis(3-methoxypropyl)gallium.

[0242] The reaction for the synthesis of dimethylaminobis(3-methoxypropyl)gallium is shown in Chemical Reaction Scheme 2 below.

[0243]

[0244] [Chemical Equation 4]

[0245]

[0246]

[0247] The synthesized dimethylaminobis(3-methoxypropyl)gallium was 11.7 g, and the synthesis yield was 50%.

[0248] The results of the analysis of dimethylaminobis(3-methoxypropyl)gallium by hydrogen nuclear magnetic resonance spectroscopy (1H-NMR) were as follows, and the graph of the analysis results is shown in Fig. 6.

[0249]

[0250] 1H-NMR (400 MHz, C6D6): δ 3.32 (t, 4H), 3.20 (s, 6H), 2.24 (s, 6H), 1.91 (m, 4H), 0.54 (t, 4H), 0.52 (m, 4H)

[0251]

[0252] [Example 1] Preparation of a Gallium Oxide Film Using Atomic Layer Deposition (ALD)

[0253] A gallium oxide film (Ga2O3) was prepared using an atomic layer deposition (ALD) apparatus with a (3-methoxypropyl)dimethylgallium precursor compound (Synthetic Example 1).

[0254] The substrate used in this experiment was a p-type Si wafer with a resistance of 0.02 Ω·cm. Prior to deposition, the p-type Si wafer was ultrasonically cleaned in acetone, ethanol, and deionized water (DI water) for 10 minutes each. The native oxide film on the Si wafer was removed after immersing it in a 10% HF solution (HF:H2O=1:9) for 10 seconds. The HF-cleaned Si wafer was immediately transferred to an atomic layer deposition (ALD) chamber.

[0255] Ozone (O3) was used as the reaction gas and injected at a flow rate of 1,000 sccm by controlling the on / off of the pneumatic valve. Argon (Ar), an inert gas, was used to purge the precursor compound and the reaction gas, and the flow rate was set to 1,500 sccm.

[0256] (Precursor compound injection for 10 seconds)-(Purge gas injection for 20 seconds)-(Reaction gas injection for 10 seconds)-(Purge gas injection for 20 seconds) were carried out sequentially, and this was considered one cycle.

[0257] At this time, the temperature of the precursor compound is 30 o It was C.

[0258] The temperature of the canister was maintained at 30℃, the process temperature was set to 120℃ to 400℃, and the number of cycles was set to 100 to deposit a gallium oxide film.

[0259] In addition, a gallium oxide film was prepared using a tris(3-methoxypropyl)gallium precursor compound (Synthetic Example 3) instead of a (3-methoxypropyl)dimethylgallium precursor compound (Synthetic Example 1) under the same conditions as the gallium oxide film deposition method described above.

[0260] It was confirmed that when a thin film is deposited using a compound according to Synthesis Example 1 or Synthesis Example 3, a thin film of uniform thickness can be stably manufactured.

[0261]

[0262] [Example 2] Preparation of an Indium Oxide Film Using Atomic Layer Deposition (ALD)

[0263] An indium oxide film (In2O3) was prepared by atomic layer deposition (ALD) using the (3-methoxypropyl)dimethylindium precursor compound synthesized in Synthesis Example 2.

[0264] A thin film was deposited under the same conditions as in Example 1, except that the precursor compound was (3-methoxypropyl)dimethylindium.

[0265] It was confirmed that when a thin film is deposited using the compound according to Synthesis Example 2, a thin film of uniform thickness can be stably manufactured.

[0266]

[0267] [Evaluation Example 1] Vapor pressure analysis of precursor compounds

[0268] Using the MST-7000 instrument from Maestec, the saturated vapor pressures of the precursor compound of Synthesis Example 1 ((3-methoxypropyl)dimethylgallium) and the precursor compound of Synthesis Example 2 ((3-methoxypropyl)dimethylindium precursor compound) under a closed-system isothermal condition were measured at 20°C, 30°C, and 40°C, respectively.

[0269] The vapor pressure at different temperatures was compared and analyzed with (3-aminopropyl)dimethylgallium ((CH3)2Ga(CH2)3N(CH3)2), which has a structure similar to the precursor compound ((3-methoxypropyl)dimethylgallium) of Synthesis Example 1, and the vapor pressure at different temperatures was compared and analyzed with (3-aminopropyl)dimethylindium ((CH3)2In(CH2)3N(CH3)2), which has a structure similar to the precursor compound ((3-methoxypropyl)dimethylindium precursor compound) of Synthesis Example 2. The vapor pressures of each compound at 20°C, 30°C, and 40°C are shown in Table 1, and the specific vapor pressure graph is shown in Figure 7.

[0270]

[0271]

[0272]

[0273] As a result of the measurement, it was found that the vapor pressure of Synthesis Example 1 was higher at all temperatures compared to (3-aminopropyl)dimethylgallium. In particular, the rate of increase in vapor pressure of Synthesis Example 1 was also higher compared to (3-aminopropyl)dimethylgallium.

[0274] Specifically, it was confirmed that the vapor pressure of (3-aminopropyl)dimethylgallium increased by 1.23 when the temperature increased by 20°C, with a rate of increase of 0.0615, whereas the vapor pressure of Synthesis Example 1 increased by 6.3 when the temperature increased by 20°C, with a rate of increase of 0.315.

[0275] In addition, the vapor pressure of Synthesis Example 2 was found to be higher at all temperatures compared to (3-aminopropyl)dimethylindium. In particular, the rate of increase in vapor pressure of Synthesis Example 2 was also higher compared to (3-aminopropyl)dimethylindium.

[0276] Specifically, it was confirmed that the vapor pressure of (3-aminopropyl)dimethylindium increased by 0.63 when the temperature increased by 20°C, with a rate of increase of 0.0315, whereas the vapor pressure of Synthesis Example 1 increased by 1.91 when the temperature increased by 20°C, with a rate of increase of 0.0955.

[0277]

[0278] [Evaluation Example 2] Thermogravimetric analysis (TGA) of precursor compounds

[0279] Thermogravimetric analysis of the precursor compound of Synthesis Example 1 ((3-methoxypropyl)dimethylgallium) and the precursor compound of Synthesis Example 2 ((3-methoxypropyl)dimethylindium) was performed using a Netzsch TG209 F1 Libra instrument.

[0280] Specifically, a 50 μL alumina crucible was used, and the amount of each sample was 10 mg. The temperature was increased from 30°C to 500°C at a rate of 10°C for measurement.

[0281] The thermogravimetric analysis results of the precursor compound of Synthesis Example 1 ((3-methoxypropyl)dimethylgallium) and the thermogravimetric analysis results of the precursor compound of Synthesis Example 2 ((3-methoxypropyl)dimethylindium precursor compound) are shown in Fig. 8.

[0282] As a result of thermogravimetric analysis, the half-life (T) of the precursor compound of Synthesis Example 1, as shown in Fig. 8, 1 / 2, The ℃) was 82℃. In addition, it was confirmed that the residual amount of the precursor compound of Synthesis Example 1 at 250℃ was 1.4%.

[0283] As a result of thermogravimetric analysis, the half-life (T) of the precursor compound of Synthesis Example 2, as shown in Fig. 8, 1 / 2 The ,°C) was 101°C. In addition, it was confirmed that the residual amount of the precursor compound of Synthesis Example 1 at 250°C was 1.55%.

[0284]

[0285] [Evaluation Example 3] Differential Scanning Calorimetry (DSC) Analysis of Thermal Properties of Precursor Compounds

[0286] Differential Scanning Calorimetry (DSC) analysis of the thermal properties of the precursor compound of Synthesis Example 1 ((3-methoxypropyl)dimethylgallium) and the precursor compound of Synthesis Example 2 ((3-methoxypropyl)dimethylindium) was performed using a Netzsch DSC 214 Polyma instrument, and the measurement results are shown in Fig. 9.

[0287] Specifically, a high-pressure sample crucible with a capacity of 100 μL was used, and the amount of all samples was 2 mg. The temperature was increased from 30°C to 500°C at a rate of 10°C for measurement.

[0288] As a result of the measurement, it was confirmed that the onset and peak temperatures of the precursor of Synthesis Example 1 were 389℃ and 416℃, respectively.

[0289] In addition, it was confirmed that the onset and peak temperatures of the precursor in Synthesis Example 2 were 280℃ and 330℃, respectively.

[0290]

[0291] As described above, it has been confirmed that the compounds of the present invention possess excellent thermal and ALD properties, and in particular, due to their high vapor pressure, thin films of uniform thickness can be stably manufactured. When manufacturing thin films using the compounds of the present invention, the precursor is easy to control, making it easy to control the amount of impurities.

[0292] Due to these excellent characteristics, thin films deposited using the compounds of the present invention are expected to be utilized as active layers of thin film transistors (TFTs) in future display devices and can be used as channels, etc., during the manufacture of memory semiconductors.

[0293]

[0294] The scope of the present invention is defined by the claims set forth below rather than by the detailed description above, and all modifications or variations derived from the meaning and scope of the claims and equivalent concepts thereof should be interpreted as being included within the scope of the present invention.

[0295] The novel compound according to the present invention and the precursor compound containing the novel compound have excellent reactivity, volatility, and thermal stability, are liquid, and enable uniform thin film deposition with excellent properties, thereby enabling the securing of excellent thin film properties, thickness, and step coverage.

[0296] The above properties provide a precursor suitable for atomic layer deposition and chemical vapor deposition.

Claims

1. A compound represented by the following chemical formula 1. [Chemical Formula 1] In the above chemical formula 1, M is Al, Ga, or In, and R1 and R2 are each independently hydrogen or, a halogen element or, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms or, an alkoxy group or, an alkyl amine or an alkoxyalkyl, and n is an integer from 1 to 5, and R3 to R5 are each independently hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

2. In Paragraph 1, R1 and R2 are each independently hydrogen, fluorine (F), chlorine (Cl), bromine (Br), methyl group, ethyl group, n-propyl group or iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, iso-pentyl group, neo-pentyl group, sec-pentyl group, tert-pentyl group, methylamine group, dimethylamine group, ethylamine group, diethylamine group, methoxyethyl, methoxypropyl, ethoxyethyl, ethoxypropyl, methoxy group or ethoxy group, compound.

3. In Paragraph 1, R3 to R5 are each independently hydrogen, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, iso-pentyl group, neo-pentyl group, sec-pentyl group, tert-pentyl group, hexyl group, or iso-hexyl group, compound.

4. In Paragraph 1, M is Al, Ga, or In, and R1 and R2 are methyl groups, and n is 3, and R3 and R4 are hydrogen, R5 is a methyl group, compound.

5. In Paragraph 1, M is Al, Ga, or In, and R1 and R2 are each independently a 3-methoxypropyl group, a halogen element, a methyl or dimethylamine group, and n is 3, and R3 and R4 are hydrogen, R5 is a methyl group, compound.

6. In Paragraph 4, M is Ga, and At 20℃, the vapor pressure is 1 Torr or higher, and At 30℃, the vapor pressure is 2 Torr or higher, and Having a vapor pressure of 3 Torr or more at 40℃, compound.

7. In Paragraph 4, M is In, At 20℃, the vapor pressure is 0.3 Torr or higher, and At 30℃, the vapor pressure is 0.6 Torr or higher, and Having a vapor pressure of 1.3 Torr or higher at 40℃, compound.

8. Comprising a compound of any one of paragraphs 1 to 7, Precursor.

9. A step comprising introducing a precursor comprising a compound of any one of claims 1 to 7 into a reactor, Method for manufacturing a thin film.

10. In Paragraph 9, The method for manufacturing the above thin film includes Atomic Layer Deposition (ALD) or Chemical Vapor Deposition (CVD). Method for manufacturing a thin film.

11. In Paragraph 9, A step further comprising introducing an oxidizing agent, a nitrating agent, a reducing agent, or a combination thereof into a reactor, Method for manufacturing a thin film.

12. In Paragraph 9, The above thin film comprises an oxide film, a nitride film, a metal film, or a combination thereof. Method for manufacturing a thin film.

13. A compound represented by the following chemical formula 4 prepared by reacting a compound represented by the following chemical formula 2 with a compound represented by the following chemical formula 3, Method for preparing a compound. [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formula 2, M is Al, Ga, or In, and R6 and R7 are each independently hydrogen or, a halogen element or, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms or, an alkoxy group or, an alkyl amine, and X1 is a halogen element, and In the above chemical formula 3, m is an integer from 1 to 5, and R8 to R 10 Each is independently hydrogen or, substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms, and M1 is MgX2, Li, Na, or K, and X2 is a halogen element, and In the above chemical formula 4, R 11 and R 12 Each is independently hydrogen or, a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms or, an alkoxy group or, an alkyl amine or an alkoxyalkyl, and R 13 to R 15 Each is independently hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

14. In Paragraph 13 A compound represented by the following chemical formula 6 is prepared by reacting the compound represented by the above chemical formula 4 with the compound of the chemical formula 5. Method for preparing a compound. [Chemical Formula 5] [Chemical Formula 6] In the above chemical formulas 5 and 6, M is Al, Ga, or In, and X3 and X4 are halogen elements, m is an integer from 1 to 5, and R 16 It is silver, hydrogen, or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms, or an alkoxy group, or an alkyl amine, or an alkoxyalkyl, and R 17 to R 19 Each is independently hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

15. In Paragraph 14, A compound represented by the above chemical formula 6 reacted with the compound of chemical formula 7 or the compound of chemical formula 8 to produce a compound represented by the following chemical formula 9. Method for preparing a compound. [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] In the above chemical formulas 7 to 9, M is Al, Ga, or In, and X5 is a halogen element, and m is an integer from 1 to 5, and M2 is Li, Na, or K, and R 20 and R 21 Each is independently a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms, and R 22 and R 23 Each is independently a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 5 carbon atoms, or an alkyl amine, or an alkoxyalkyl, and R 24 to R 26 Each is independently hydrogen or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 6 carbon atoms.

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