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WO2018182309A1 - Composition pour déposer un film mince contenant du silicium contenant un composé bis(aminosilyl)alkylamine et procédé de fabrication de film mince contenant du silicium l'utilisant - Google Patents

Composition pour déposer un film mince contenant du silicium contenant un composé bis(aminosilyl)alkylamine et procédé de fabrication de film mince contenant du silicium l'utilisant Download PDF

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Publication number
WO2018182309A1
WO2018182309A1 PCT/KR2018/003655 KR2018003655W WO2018182309A1 WO 2018182309 A1 WO2018182309 A1 WO 2018182309A1 KR 2018003655 W KR2018003655 W KR 2018003655W WO 2018182309 A1 WO2018182309 A1 WO 2018182309A1
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Prior art keywords
chemical formula
silicon
thin film
composition
aminosilyl
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PCT/KR2018/003655
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English (en)
Inventor
Sung Gi Kim
Jeong Joo Park
Joong Jin Park
Se Jin Jang
Byeong-Il Yang
Sang-Do Lee
Sam Dong Lee
Sang Ick Lee
Myong Woon Kim
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DNF Co Ltd
Original Assignee
DNF Co Ltd
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Priority claimed from KR1020180035010A external-priority patent/KR20180110612A/ko
Application filed by DNF Co Ltd filed Critical DNF Co Ltd
Priority to CN201880019422.XA priority Critical patent/CN110431204B/zh
Priority to US16/499,215 priority patent/US11393676B2/en
Priority to JP2019553053A priority patent/JP6876145B2/ja
Publication of WO2018182309A1 publication Critical patent/WO2018182309A1/fr
Anticipated expiration legal-status Critical
Priority to US17/572,509 priority patent/US11749522B2/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/16—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
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    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/34—Nitrides
    • C23C16/345—Silicon nitride
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/40—Oxides
    • C23C16/401—Oxides containing silicon
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    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/44—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating
    • C23C16/455—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
    • C23C16/45523—Pulsed gas flow or change of composition over time
    • C23C16/45525—Atomic layer deposition [ALD]
    • C23C16/45527—Atomic layer deposition [ALD] characterized by the ALD cycle, e.g. different flows or temperatures during half-reactions, unusual pulsing sequence, use of precursor mixtures or auxiliary reactants or activations
    • C23C16/45536—Use of plasma, radiation or electromagnetic fields
    • C23C16/4554—Plasma being used non-continuously in between ALD reactions
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/44—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating
    • C23C16/455—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
    • C23C16/45523—Pulsed gas flow or change of composition over time
    • C23C16/45525—Atomic layer deposition [ALD]
    • C23C16/45553—Atomic layer deposition [ALD] characterized by the use of precursors specially adapted for ALD
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
    • H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
    • H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
    • H01L21/02164—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material being a silicon oxide, e.g. SiO2
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
    • H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
    • H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
    • H01L21/0217—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material being a silicon nitride not containing oxygen, e.g. SixNy or SixByNz
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
    • H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
    • H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
    • H01L21/02219—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and nitrogen
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
    • H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
    • H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
    • H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
    • H01L21/02274—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition in the presence of a plasma [PECVD]
    • H—ELECTRICITY
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    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
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    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
    • H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
    • H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
    • H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
    • H01L21/0228—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition deposition by cyclic CVD, e.g. ALD, ALE, pulsed CVD
    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/62—Nitrogen atoms

Definitions

  • the present invention relates to a composition for depositing a silicon-containing thin film and a method for manufacturing a silicon-containing thin film using the same, and more particularly, to a composition for depositing a silicon-containing thin film, containing a specific compound, a bis(aminosilyl)alkylamine compound as a precursor for depositing a thin film, and a method for manufacturing a silicon-containing thin film using the same.
  • a silicon-containing thin film is manufactured through various deposition processes in a semiconductor field to thereby be manufactured in various forms such as a silicon film, a silicon oxide film, a silicon nitride film, a silicon carbonitride film, and a silicon oxynitride film, and an application field of the silicon-containing thin film may be wide.
  • the silicon oxide film and the silicon nitride film have a significantly excellent barrier property and oxidation resistance
  • the silicon oxide film and the silicon nitride film are used as an insulating film, a diffusion barrier, a hard mask, an etch stop layer, a seed layer, a spacer, a trench isolation, an intermetallic dielectric material, and a passivation layer in manufacturing an apparatus.
  • TFT thin film transistor
  • MOCVD metal-organic chemical vapor deposition
  • ALD atomic layer deposition
  • LPCVD low-pressure chemical vapor deposition
  • PECVD plasma-enhanced chemical vapor deposition
  • PEALD plasma-enhanced atomic layer deposition
  • a precursor used to form the silicon-containing thin film may include silane, silane compounds, aminosilane, and alkoxysilane compounds.
  • Specific examples thereof may include silane chloride compounds such as dichlorosilane (SiH 2 Cl 2 ) and hexachlorodisilane (Cl 3 SiSiCl 3 ), trisilylamine (N(SiH 3 ) 3 ), bis-diethylaminosilane (H 2 Si(N(CH 2 CH 3 ) 2 ) 2 ), di-isopropylaminosilane (H 3 SiN(i-C 3 H 7 ) 2 ), and the like.
  • silane chloride compounds such as dichlorosilane (SiH 2 Cl 2 ) and hexachlorodisilane (Cl 3 SiSiCl 3 ), trisilylamine (N(SiH 3 ) 3 ), bis-diethylaminosilane (H 2 Si(N(CH 2 CH 3 ) 2
  • An object of the present invention is to provide a composition for depositing a silicon-containing thin film, containing a bis(aminosilyl)alkylamine compound capable of being used as a precursor of the silicon-containing thin film.
  • Another object of the present invention is to provide a method for manufacturing a silicon-containing thin film using the composition for depositing a silicon-containing thin film according to the present invention.
  • Another object of the present invention is to provide a bis(aminosilyl)alkylamine compound capable of being used as a precursor of a silicon-containing thin film.
  • composition for depositing a silicon-containing thin film containing: a bis(aminosilyl)alkylamine compound, which has excellent physical properties as a precursor for thin film deposition, as a precursor for silicon-containing thin film deposition, wherein the bis(aminosilyl)alkylamine compound is represented by the following Chemical Formula 1.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 1 to R 4 are each independently hydrogen, (C1-C7)alkyl, or (C2-C7)alkenyl, or R 1 and R 2 , and R 3 and R 4 are each independently linked to each other to form a ring; and
  • R 5 to R 8 are each independently hydrogen, halogen, (C1-C7)alkyl, or (C2-C7)alkenyl.)
  • R 5 to R 7 may be each independently hydrogen, halogen, (C1-C7)alkyl, or (C2-C7)alkenyl, and R 8 may be hydrogen.
  • the bis(aminosilyl)alkylamine compound according to the exemplary embodiment of the present invention may be represented by the following Chemical Formula 2 or 3.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 5 to R 7 are each independently hydrogen, halogen, (C1-C7)alkyl, or (C2-C7)alkenyl;
  • R 11 to R 14 are each independently hydrogen, (C1-C5)alkyl, or (C2-C5)alkenyl;
  • n and m are each independently an integer of 1 to 7.
  • R 5 to R 7 may be each independently hydrogen or (C1-C5)alkyl
  • R 11 to R 14 may be each independently hydrogen, (C1-C5)alkyl, or (C2-C5)alkenyl
  • n and m may be each independently an integer of 1 to 4.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 4 or 5.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 11 to R 14 are each independently hydrogen, (C1-C7)alkyl, or (C2-C7)alkenyl;
  • R 5 and R 6 are each independently (C1-C7)alkyl, or (C2-C7)alkenyl;
  • n and m are each independently an integer of 1 to 7.
  • R may be (C1-C5)alkyl; R 5 and R 6 may be each independently (C1-C5)alkyl; and n and m may be each independently an integer of 1 to 4.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 6 or 7.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 11 to R 14 are each independently hydrogen, (C1-C7)alkyl, or (C2-C7)alkenyl;
  • n and m are each independently an integer of 1 to 7.
  • R may be (C1-C5)alkyl; R 11 to R 14 may be each independently hydrogen, (C1-C5)alkyl, or (C2-C5)alkenyl; and n and m may be each independently an integer of 1 to 4.
  • the bis(aminosilyl)alkylamine compound according to the exemplary embodiment of the present invention may be selected from the following compounds, but is not limited thereto.
  • the composition for depositing a silicon-containing thin film may be deposited by an atomic layer deposition (ALD) method, a chemical vapor deposition (CVD) method, a metal-organic chemical vapor deposition (MOCVD) method, a low-pressure chemical vapor deposition (LPCVD) method, a plasma-enhanced chemical vapor deposition (PECVD) method, or a plasma-enhanced atomic layer deposition (PEALD) method
  • the silicon-containing thin film may be a silicon oxide (SiO 2 ) film, a silicon oxy carbide (SiOC) film, a silicon nitride (SiN) film, a silicon oxy nitride (SiON) film, a silicon carbonitride (SiCN) film, or a silicon carbide (SiC) film.
  • the method for manufacturing a silicon-containing thin film may include: a) maintaining a temperature of a substrate mounted in a chamber at 30 to 500°C;
  • composition for depositing a silicon-containing thin film described above with the substrate to adsorb the composition for depositing a silicon-containing thin film in the substrate;
  • reaction gas is supplied after being activated by generating plasma with a plasma power of 50 to 1000 W.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 may be represented by Chemical Formula 2 or 3.
  • a composition for depositing a silicon-containing thin film contains a bis(aminosilyl)alkylamine compound which is a liquid at room temperate and has high volatility and excellent thermal stability as a precursor, such that a high-quality silicon-containing thin film having a high purity and durability may be provided under lower plasma power and film formation temperature conditions.
  • a silicon-containing thin film using the composition for depositing a silicon-containing thin film according to the present invention excellent thermal stability and deposition rate, and excellent stress intensity may be implemented even under a low film formation temperature condition, and in a silicon-containing thin film manufactured thereby, contents of impurities such as carbon, oxygen, and hydrogen are minimized, thereby making it possible to manufacture a silicon-containing thin film having a high purity, excellent physical and electrical properties, excellent resistance against hydrogen fluoride, an excellent water vapor transmission rate, and an excellent step coverage.
  • FIG. 1 is a view illustrating a result obtained by measuring vapor pressures of bis(aminosilyl)alkylamine compounds prepared in Examples 1 and 2.
  • FIG. 2 is a view illustrating results obtained by performing thermogravimetric analysis on the bis(aminosilyl)alkylamine compounds prepared in Examples 1 and 2.
  • FIG. 3 is a view illustrating results obtained by performing infrared spectroscopic analysis on deposited films of silicon oxide thin films manufactured in Examples 3 to 5.
  • FIG. 4 is a view illustrating results obtained by performing infrared spectroscopic analysis on deposited films of silicon nitride thin films manufactured in Examples 6 to 9.
  • the present invention provides a composition for depositing a silicon-containing thin film containing a bis(aminosilyl)alkylamine compound, which is a liquid at room temperature and has high volatility and excellent thermal stability to thereby be used as a useful precursor for forming a silicon-containing thin film, wherein the bis(aminosilyl)alkylamine compound is represented by the following Chemical Formula 1.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 1 to R 4 are each independently hydrogen, (C1-C7)alkyl, or (C2-C7)alkenyl, or R 1 and R 2 , and R 3 and R 4 are each independently linked to each other to form a ring; and
  • R 5 to R 8 are each independently hydrogen, halogen, (C1-C7)alkyl, or (C2-C7)alkenyl.)
  • composition for depositing a silicon-containing thin film according to the present invention contains a precursor for depositing a thin film represented by Chemical Formula 1, such that film formation may be performed at a low temperature, and at the same time, a high-quality thin film having high durability may be easily manufactured.
  • composition for depositing a silicon-containing thin film according to the present invention contains the precursor for depositing a thin film represented by Chemical Formula 1, the thin film may be deposited at a high thin film deposition rate, and the film has excellent stress properties and water vapor transmission rate.
  • the reason may be that as the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1, contained in the composition for depositing a silicon-containing thin film has two aminosilyl groups and one alkyl or alkenyl group as substituents, the bis(aminosilyl)alkylamine compound has high volatility and excellent thermal stability.
  • R 5 to R 7 may be each independently hydrogen, halogen, (C1-C7)alkyl, or (C2-C7)alkenyl, and R 8 may be hydrogen.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 5 to R 7 are each independently hydrogen, halogen, (C1-C7)alkyl, or (C2-C7)alkenyl;
  • R 11 to R 14 are each independently hydrogen, (C1-C5)alkyl, or (C2-C5)alkenyl;
  • n and m are each independently an integer of 1 to 7.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 2 or 3 two aminosilyl functional groups and one alkyl or alkenyl group are substituted, such that the bis(aminosilyl)alkylamine compound is thermally stable, and at the same time, the bis(aminosilyl)alkylamine compound has a silazane backbone in which at least one hydrogen atom in at least one of two aminosilyl functional groups is substituted, such that the bis(aminosilyl)alkylamine compound has high volatility as a liquid at room temperature. Therefore, the bis(aminosilyl)alkylamine compound may be significantly usefully used to form a silicon-containing thin film.
  • the bis(aminosilyl)alkylamine compound according to the present invention which is a compound having the silazane backbone, essentially has two aminosilyl functional groups ( and or and ), and silyl in one of the aminosilyl functional groups necessarily has a functional group containing at least one hydrogen atom ( or ), such that the bis(aminosilyl)alkylamine compound may have excellent effects as the precursor for depositing a thin film.
  • R 5 to R 7 may be each independently hydrogen or (C1-C5)alkyl
  • R 11 to R 14 may be each independently hydrogen, (C1-C5)alkyl, or (C2-C5)alkenyl
  • n and m may be each independently an integer of 1 to 4.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 according to the present invention may be represented by the following Chemical Formula 4 or 5.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 11 to R 14 are each independently hydrogen, (C1-C7)alkyl, or (C2-C7)alkenyl;
  • R 5 and R 6 are each independently (C1-C7)alkyl, or (C2-C7)alkenyl;
  • n and m are each independently an integer of 1 to 7.
  • R may be (C1-C5)alkyl; R 5 and R 6 may be each independently (C1-C5)alkyl; and n and m may be each independently an integer of 1 to 4. More preferably, the bis(aminosilyl)alkylamine compound may be represented by Chemical Formula 4, and in Chemical Formula 4, R may be (C1-C3)alkyl; and R 5 and R 6 may be each independently (C1-C3)alkyl.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 6 or 7.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 11 to R 14 are each independently hydrogen, (C1-C7)alkyl, or (C2-C7)alkenyl;
  • n and m are each independently an integer of 1 to 7.
  • R may be (C1-C5)alkyl; R 11 to R 14 may be each independently hydrogen, (C1-C5)alkyl, or (C2-C5)alkenyl; n and m may be each independently an integer of 1 to 4.
  • R may be (C1-C5)alkyl; R 11 to R 14 may be each independently (C1-C5)alkyl; and n and m may be each independently 1 to 4.
  • the bis(aminosilyl)alkylamine compound may be represented by Chemical Formula 6, wherein in Chemical Formula 6, R may be (C1-C3)alkyl; and R 11 to R 14 may be each independently (C1-C3)alkyl.
  • the bis(aminosilyl)alkylamine compound When silyl groups of two aminosilyl groups in the silazane backbone of the bis(aminosilyl)alkylamine compound according to the present invention have two or four hydrogen atoms, the bis(aminosilyl)alkylamine compound has more excellent reactivity and thermal stability as the precursor for depositing a thin film, such that a higher-quality thin film may be manufactured.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 4 may be represented by the following Chemical Formula 4-1.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 1 and R 2 are each independently hydrogen, (C1-C7)alkyl, or (C2-C7)alkenyl, or R 1 and R 2 is each independently linked to each other to form a ring;
  • R 5 is (C1-C7)alkyl or (C2-C7)alkenyl.)
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 6 may be represented by the following Chemical Formula 6-1.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 1 and R 2 are each independently (C1-C7)alkyl, or (C2-C7)alkenyl, or are linked to each other to form a ring.)
  • bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 may include the following compounds.
  • the composition for depositing a silicon-containing thin film according to the present invention needs to necessarily contain the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 as the precursor for depositing a thin film, and the bis(aminosilyl)alkylamine compound may be contained in the composition for depositing a silicon-containing thin film in a content range in which the content may be recognized by those skilled in the art in consideration of film formation conditions, a thickness, properties, or the like of the thin film.
  • alkyl means linear, branched, and cyclic saturated and unsaturated hydrocarbons having 1 to 7 carbon atoms, preferably, 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms, and examples thereof may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, neobutyl, pentyl, and the like.
  • halogen means a halogen element, and examples thereof include fluoro, chloro, bromo, and iodo.
  • alkenyl as a single group or a part of another group means a straight-chain, branched-chain, or cyclic hydrocarbon radical having 2 to 7 carbon atoms and one or more carbon-carbon double bonds.
  • a more preferable alkenyl radical is a lower alkenyl radical having 2 to 5 carbon atoms.
  • the most preferable lower alkenyl radical is a lower alkenyl radical having about 2 to 3 carbon atoms.
  • the alkenyl group may be substituted at a random usable attachment point. Examples of the alkenyl radical include ethenyl, propenyl, allyl, butenyl, and 4-methylbutenyl.
  • alkenyl and “lower alkenyl” include radicals having cis and trans orientations or alternatively, E and Z orientations.
  • R 1 and R 2 , and R 3 and R 4 are each independently linked to each other to form a ring
  • the phrase “R 1 and R 2 , and R 3 and R 4 are each independently linked to each other to form a ring” includes the case in which R 1 and R 2 are linked to each other to form a ring but R 3 and R 4 do not form a ring; the case in which on the contrary, R 1 and R 2 do not form a ring but R 3 and R 4 are linked to each other to form a ring; and the case in which R 1 and R 2 are linked to each other to form a ring and R 3 and R 4 are linked to each other to form a ring, wherein the formed ring may be an alicyclic or aromatic ring containing N, and preferably, an alicyclic ring.
  • alicyclic ring means a compound that is not an aromatic compound among organic compounds having a cyclic bonding structure.
  • the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1 according to the present invention may be prepared using a method as long as the method may be recognized by those skilled in the art.
  • the present invention provides a method for manufacturing a silicon-containing thin film using the composition for depositing a silicon-containing thin film according to the present invention.
  • the composition for depositing a silicon-containing thin film according to the present invention containing the bis(aminosilyl)alkylamine compound represented by Chemical Formula 1, which is a liquid art room temperature and normal pressure and has high volatility and excellent thermal stability, as the precursor is used, the handling may be easy, it is possible to manufacture various thin films, and it is possible to manufacture a silicon-containing thin film having a high purity, an excellent water vapor transmission rate, and excellent thin film stress properties at a high deposition rate even at a low temperature and a low power.
  • the silicon-containing thin film manufactured by the method according to the present invention has excellent durability and electric properties, and resistance against hydrogen fluoride and step coverage thereof are also excellent.
  • the silicon-containing thin film may be formed by any method as long as it may be recognized by those skilled in the art.
  • the silicon-containing thin film may be formed by an atomic layer deposition (ALD) method, a chemical vapor deposition (CVD) method, a metal-organic chemical vapor deposition (MOCVD) method, a low-pressure chemical vapor deposition (LPCVD) method, a plasma enhanced chemical vapor deposition (PECVD) method, or a plasma enhanced atomic layer deposition (PEALD) method, but PECVD, ALD, or PEALD is more preferable in order to allow the thin film to be more easily deposited, and allow the manufactured thin film to have excellent properties.
  • ALD atomic layer deposition
  • CVD chemical vapor deposition
  • MOCVD metal-organic chemical vapor deposition
  • LPCVD low-pressure chemical vapor deposition
  • PECVD plasma enhanced chemical vapor deposition
  • PEALD plasma enhanced atomic layer deposition
  • the silicon-containing thin film according to the present invention may be a silicon oxide (SiO 2 ) film, a silicon oxy carbide (SiOC) film, a silicon nitride (SiN) film, a silicon oxy nitride (SiON) film, a silicon carbonitride (SiCN) film, or a silicon carbide (SiC) film, and various thin films having high quality, particularly, a thin film usable as an encapsulant of an organic light emitting diode (OLED), may be manufactured.
  • SiO 2 silicon oxide
  • SiOC silicon oxy carbide
  • SiN silicon nitride
  • SiON silicon oxy nitride
  • SiCN silicon carbonitride
  • SiC silicon carbide
  • the method for manufacturing a silicon-containing thin film according to the present invention may include:
  • composition for depositing a silicon-containing thin film according to the present invention contacting the composition for depositing a silicon-containing thin film according to the present invention with the substrate to adsorb the composition for depositing a silicon-containing thin film in the substrate;
  • the method for manufacturing a silicon-containing thin film according to the present invention may include:
  • composition for depositing a silicon-containing thin film according to the present invention with the substrate to adsorb the composition for depositing a silicon-containing thin film in the substrate;
  • reaction gas in step D) may remove a ligand of the bis(aminosilyl)alkylamine compound contained in the composition for depositing a silicon-containing thin film to form a Si-O atomic layer.
  • the reaction gas according to the exemplary embodiment of the present invention may be supplied after being activated by generating plasma at a plasma power of 50 to 1000 W.
  • a bis(aminosilyl)alkylamine compound according to the present invention is used as the precursor, such that the reaction gas may be activated at preferably 30 to 500°C, and more preferably 30 to 300°C by generating plasma at a low plasma power of 50 to 1000 W, preferably 100 to 800 W, and more preferably 400 to 600 W, thereby making it possible to manufacture the thin film.
  • deposition conditions may be adjusted depending on a structure or thermal properties of a desired thin film.
  • the deposition condition according to the exemplary embodiment of the present invention may include an injection flow rate of the composition for depositing a silicon-containing thin film containing the bis(aminosilyl)alkyl amine compound, injection flow rates of the reaction gas and a carrier gas, pressure, RF power, the temperature of the substrate, and the like.
  • the injection flow rate of the composition for depositing a silicon-containing thin film may be adjusted in a range of 10 to 1000 cc/min
  • the injection flow rate of the carrier gas may be adjusted in a range of 10 to 1000 cc/min
  • the injection flow rate of the reaction gas may be adjusted in a range of 1 to 1500 cc/min
  • the pressure may be adjusted in a range of 0.5 to 10 torr
  • the RF power may be adjusted in a range of 50 to 1000 W
  • the temperature of the substrate may be adjusted in a range of 30 to 500°C, preferably 80 to 300°C, but the deposition conditions are not limited thereto.
  • the reaction gas used in the method for manufacturing a silicon-containing thin film according to the present invention is not limited, but may be one selected from hydrogen (H 2 ), hydrazine (N 2 H 4 ), ozone (O 3 ), oxygen (O 2 ), nitrous oxide (N 2 O) ammonia (NH 3 ), nitrogen (N 2 ), silane (SiH 4 ), borane (BH 3 ), diborane (B 2 H 6 ), and phosphine (PH 3 ), or a mixed gas of one or more thereof, and the carrier gas may be one selected from nitrogen (N 2 ), argon (Ar), and helium (He), or a mixed gas of two or more thereof.
  • the substrate used in the method for manufacturing a silicon-containing thin film according to the present invention may be a substrate containing one or more semiconductor materials selected from Si, Ge, SiGe, GaP, GaAs, SiC, SiGeC, InAs, and InP; a silicon-on-insulator (SOI) substrate; a quartz substrate; a glass substrate for a display; or a flexible plastic substrate made of polyimide, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polymethylmethacrylate (PMMA), polycarbonate (PC), polyethersulfone(PES), polyester, and the like, but is not limited thereto.
  • SOI silicon-on-insulator
  • the silicon-containing thin film may be directly formed on the substrate.
  • a large number of conductive layers, dielectric layers, insulating layers, or the like, may also be formed between the substrate and the silicon-containing thin film.
  • the present invention provides a bis(aminosilyl)alkyl amine compound capable of being used as a precursor of a silicon-containing thin film.
  • the bis(aminosilyl)alkyl amine compound according to the present invention is represented by the following Chemical Formula 1.
  • R is (C1-C7)alkyl or (C2-C7)alkenyl
  • R 1 to R 4 are each independently hydrogen, (C1-C7)alkyl, or (C2-C7)alkenyl, or R 1 and R 2 , and R 3 and R 4 are each independently linked to each other to form a ring; and
  • R 5 to R 8 are each independently hydrogen, halogen, (C1-C7)alkyl, or (C2-C7)alkenyl.)
  • the bis(aminosilyl)alkyl amine compound according to the present invention represented by Chemical Formula 1 is a liquid at room temperature and has high volatility and excellent thermal stability as described above, such that the bis(aminosilyl)alkyl amine compound is used as a significantly useful precursor in forming a silicon-containing thin film.
  • the bis(aminosilyl)alkyl amine compound has excellent reactivity, such that the thin film may be deposited at a rapid deposition rate, and the thin film with a high purity may be manufactured.
  • the bis(aminosilyl)alkyl amine compound represented by Chemical Formula 1 may be represented by Chemical Formula 2, and more preferably Chemical Formula 6 or 7.
  • deposition was performed by a plasma enhanced atomic layer deposition (PEALD) method known in the art using a commercialized 200 mm single wafer shower head type ALD apparatus (CN1, Atomic Premium).
  • PEALD plasma enhanced atomic layer deposition
  • PECVD plasma enhanced chemical vapor deposition
  • CN1, Atomic Premium a commercialized 200 mm single wafer shower head type CVD apparatus
  • a thickness of a deposited silicon-containing thin film was measured using an ellipsometer (OPTI-PROBE 2600, THERMA-WAVE), and properties of the thin film were analyzed using infrared spectroscopy (IFS66V/S & Hyperion 3000, Bruker Optics), X-ray photoelectron spectroscopy, a water vapor transmission rate (WVTR) analyzer (MOCON, Aquatran 2), and a stress analyzer (Frontier Semiconductor, FSM500TC).
  • IFS66V/S & Hyperion 3000 Bruker Optics
  • WVTR water vapor transmission rate
  • FSM500TC Frier Semiconductor
  • Film was formed using the bis(ethylmethylaminosilyl)methyl amine compound prepared in Example 2 according to the present invention as a composition for forming a silicon oxide film in a general plasma enhanced atomic layer deposition (PEALD) apparatus using a plasma enhanced atomic layer deposition (PEALD) method known in the art.
  • PEALD plasma enhanced atomic layer deposition
  • nitrous oxide was used together with plasma, and nitrogen corresponding to an inert gas was used for purging.
  • the film was formed at reaction gas and plasma time of 0.5 seconds.
  • a specific method for depositing a silicon oxide thin film was illustrated in Table 1.
  • Silicon oxide thin films were manufactured in the same manner as in Example 3 except for changing deposition conditions illustrated in the following Table 1 in Example 3, results obtained by analyzing the manufactured silicon oxide thin film were illustrated in the following Table 2, and results obtained by analyzing the deposited film using the infrared spectroscopy were illustrated in FIG. 3.
  • Film was formed using the bis(ethylmethylaminosilyl)methyl amine compound prepared in Example 2 according to the present invention as a composition for forming a silicon nitride film in a general plasma enhanced atomic layer deposition (PEALD) apparatus using a plasma enhanced atomic layer deposition (PEALD) method known in the art.
  • PEALD plasma enhanced atomic layer deposition
  • As a reaction gas nitrogen and ammonia were used together with plasma as first reaction gas, and nitrogen was used as a second reaction gas. The nitrogen corresponding to an inert gas was used for purging.
  • a specific method for depositing a silicon nitride thin film was illustrated in Table 3.
  • Silicon nitride thin films were manufactured in the same manner as in Example 6 except for changing conditions illustrated in the following Table 3 in Example 6, results obtained by analyzing the manufactured silicon oxide thin film were illustrated in the following Table 4, and results obtained by analyzing the deposited film using the infrared spectrometer were illustrated in FIG. 4.

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Abstract

L'invention concerne une composition pour déposer un film mince contenant du silicium contenant un composé bis(aminosilyl)alkylamine et un procédé de fabrication d'un film mince contenant du silicium l'utilisant, et plus particulièrement, une composition pour déposer un film mince contenant du silicium, contenant le composé bis(aminosilyl)alkylamine pouvant être utilisé de manière utile en tant que précurseur du film mince contenant du silicium, et un procédé de fabrication d'un film mince contenant du silicium l'utilisant.
PCT/KR2018/003655 2017-03-29 2018-03-28 Composition pour déposer un film mince contenant du silicium contenant un composé bis(aminosilyl)alkylamine et procédé de fabrication de film mince contenant du silicium l'utilisant Ceased WO2018182309A1 (fr)

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CN201880019422.XA CN110431204B (zh) 2017-03-29 2018-03-28 沉积含硅薄膜的含双(氨基甲硅烷基)烷基胺化合物的组合物及使用其制造含硅薄膜的方法
US16/499,215 US11393676B2 (en) 2017-03-29 2018-03-28 Composition for depositing silicon-containing thin film containing bis(aminosilyl)alkylamine compound and method for manufacturing silicon-containing thin film using the same
JP2019553053A JP6876145B2 (ja) 2017-03-29 2018-03-28 ビス（アミノシリル）アルキルアミン化合物を含むシリコン含有薄膜蒸着用組成物、およびそれを用いたシリコン含有薄膜の製造方法
US17/572,509 US11749522B2 (en) 2017-03-29 2022-01-10 Composition for depositing silicon-containing thin film containing bis(aminosilyl)alkylamine compound and method for manufacturing silicon-containing thin using the same

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KR1020180035010A KR20180110612A (ko) 2017-03-29 2018-03-27 비스(아미노실릴)알킬아민 화합물을 포함하는 실리콘 함유 박막증착용 조성물 및 이를 이용하는 실리콘 함유 박막의 제조방법

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CN113748226A (zh) * 2019-04-25 2021-12-03 弗萨姆材料美国有限责任公司 用于氧化硅薄膜的高温原子层沉积的有机氨基二硅氮烷
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