WO2014084557A1 - Composés de précurseur de silicium et procédé de dépôt de film mince contenant du silicium l'utilisant - Google Patents

Composés de précurseur de silicium et procédé de dépôt de film mince contenant du silicium l'utilisant Download PDF

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WO2014084557A1
WO2014084557A1 PCT/KR2013/010720 KR2013010720W WO2014084557A1 WO 2014084557 A1 WO2014084557 A1 WO 2014084557A1 KR 2013010720 W KR2013010720 W KR 2013010720W WO 2014084557 A1 WO2014084557 A1 WO 2014084557A1
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silicon
nhr
sicl
formula
thin film
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PCT/KR2013/010720
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English (en)
Korean (ko)
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한원석
고원용
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주식회사 유피케미칼
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    • 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
    • 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
    • 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
    • C23C16/06—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 metallic material
    • 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
    • C23C16/34—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
    • 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

Definitions

  • the present application relates to a silicon precursor compound and a method for preparing the silicon precursor compound, a precursor composition for depositing a silicon-containing thin film containing the silicon precursor compound, and a method for depositing a silicon-containing thin film using the precursor compound.
  • Silicon-containing thin films include semiconductors such as microelectronic devices such as RAM (memory and logic chips), flat panel displays including thin film transistors (TFTs), and semiconductor technologies such as the solar field. It is used as a diffusion mask, an antioxidant film, a dielectric film, and the like. In the recent process of manufacturing such a thin film, the thin film is formed by thermal oxidation at a high temperature of 900 ° C. or higher, or by Low Pressure Chemical Deposition (LPCVD) at 700 ° C. or higher. Eliminates efficient, cost-effective production of silicon-containing thin films for the field. In particular, with the miniaturization of semiconductor devices, the necessity of lowering the process temperature is increasing.
  • LPCVD Low Pressure Chemical Deposition
  • Typical chemical vapor deposition precursors for forming a silicon-containing thin film include silane, disilane, dichlorosilane, and trichlorosilane. These precursors have a high minimum film deposition temperature, which precludes their use as precursors for semiconductor applications where low processing temperatures are required. In addition, because the xylene precursor is spontaneously ignited, highly toxic, and susceptible to corrosion, strict safety precautions are required.
  • atomic layer deposition to form a silicon-containing thin film is expected to improve the thickness uniformity and physical properties of the thin film and to lower the processing temperature, thereby improving the characteristics of the semiconductor device.
  • very effective applications are expected in the case of gate spacers, which require excellent properties and coating properties at very thin thicknesses.
  • the present application is to provide a silicon precursor compound, represented by the following formula (1) or formula (2), and a method for preparing the same:
  • R 1 and R 2 are each independently H or a C 1-5 linear or branched alkyl group
  • n and m are each independently 1-3.
  • R 1 to R 4 are each independently H or C 1-5 linear or branched alkyl groups
  • x is 0 or 1
  • y 1 or 2
  • z is 0 or 2.
  • the present invention is to provide a precursor composition for silicon-containing thin film deposition comprising the silicon precursor compound.
  • the present application is to provide a method for depositing a silicon-containing thin film using the silicon precursor compound.
  • a first aspect of the present application provides a silicon precursor compound, represented by the following Chemical Formula 1:
  • R 1 and R 2 are each independently H or a C 1-5 linear or branched alkyl group
  • n and m are each independently 1 to 3.
  • a second aspect of the present application provides a silicon precursor compound, represented by the following Chemical Formula 2:
  • R 1 to R 4 are each independently H or a C 1-5 linear or branched alkyl group
  • x is 0 or 1
  • y 1 or 2
  • z is 0 or 2.
  • the third aspect of the present application provides a method for producing a silicon precursor compound, represented by the formula (1).
  • the fourth aspect of the present application provides a method for producing a silicon precursor compound, represented by the formula (2).
  • the fifth aspect of the present application provides a precursor composition for depositing a silicon-containing thin film including the silicon precursor compound according to Formula 1 or Formula 2.
  • a sixth aspect of the present disclosure provides a method for depositing a silicon-containing thin film using the silicon precursor chemical according to Formula 1 or Formula 2.
  • silicon precursor compound according to the present invention has improved properties with high thermal stability that does not deteriorate even under continuous heating, compared to the conventional silicon precursor compound, silicon-containing thin film deposition may be performed by chemical vapor deposition or atomic layer deposition. When used as a silicon precursor.
  • thermogravimetric analysis (TGA) graph of silicon precursor compound 1 according to an embodiment of the present disclosure.
  • DSC differential scanning calorimetry
  • thermogravimetric analysis graph of the silicon precursor compound 2 according to an embodiment of the present application.
  • Figure 4 is a differential scanning calorimetry graph of the silicon precursor compound 2 according to an embodiment of the present application.
  • thermogravimetric analysis graph of the silicon precursor compound 3 is a thermogravimetric analysis graph of the silicon precursor compound 3 according to an embodiment of the present application.
  • thermogravimetric analysis graph of the silicon precursor compound 4 according to an embodiment of the present application.
  • the term "combination (s) thereof" included in the representation of a makushi form refers to one or more mixtures or combinations selected from the group consisting of the components described in the representation of makushi form, It means to include one or more selected from the group consisting of the above components.
  • alkyl group may include linear or branched, saturated or unsaturated C 1-5 alkyl groups, respectively, for example methyl, ethyl, propyl, butyl, pentyl or their It may be to include all possible isomers of, but may not be limited thereto.
  • n Pr in the specific compound name means n-propyl (n-Pr), i Pr means iso-propyl (i-Pr), and n Bu is n-butyl (n-Bu) I Bu means iso-butyl (iso-Bu) and t Bu means tert -butyl (t-Bu).
  • a first aspect of the present application provides a silicon precursor compound represented by the following general formula (1):
  • R 1 and R 2 are each independently H or a C 1-5 linear or branched alkyl group; n and m are each independently 1 to 3.
  • the C 1-5 linear or branched alkyl group is a methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, tert -butyl group , n-pentyl, iso-pentyl, neo-pentyl or tert -pentyl may include, but may not be limited thereto.
  • a second aspect of the present application provides a silicon precursor compound represented by the following general formula (2):
  • R 1 to R 4 are each independently H or a C 1-5 linear or branched alkyl group; x is 0 or 1; y is 1 or 2; z is 0 or 2.
  • the C 1-5 linear or branched alkyl group is a methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, tert -butyl group , n-pentyl, iso-pentyl, neo-pentyl or tert -pentyl may include, but may not be limited thereto.
  • the silicon precursor compound according to Formula 1 or Formula 2 is (NH 2 Si (NHMe) 3 , (NH 2 Si (NHEt) 3 , (NH 2 Si (NH) n Pr) 3 , (NH 2 Si (NH) i Pr) 3 , (NH 2 Si (NH) n Bu) 3 , (NH 2 Si (NH) i Bu) 3 , (NH 2 Si (NH) t Bu) 3 , (NMe 2 Si (NHMe) 3 , (NMe 2 Si (NHEt) 3 , (NMe 2 Si (NH) n Pr) 3 , (NMe 2 Si (NH) i Pr) 3 , (NMe 2 Si (NH) n Bu) 3 , (NMe 2 Si (NH) i Bu) 3 , (NMe 2 Si (NH) i Bu) 3 , (NMe 2 Si (NH) i Bu) 3 , (NMe 2 Si (NH) i Bu) 3 , (NMe 2 Si (NH) i Bu) 3 , (NM
  • a third aspect of the present application is to react SiCl 4 and NH 2 R 2 in an organic solvent to form SiCl n (NHR 2 ) m as in Scheme 1 below; And forming a silicon compound by reacting the SiCl n (NHR 2 ) m and M (NR 1 2 ) in an organic solvent to form a silicon precursor compound of Formula 1 of the first aspect of the present application. to provide:
  • M is an alkali metal
  • R 1 , R 2 , n, and m are the same as defined above in the first aspect of the present application, respectively.
  • a fourth aspect of the present application is to react SiCl 4 and NH 2 R 4 in an organic solvent to form SiCl y (NHR 4 ) z as in Scheme 2 below; And reacting the SiCl y (NHR 2 ) z and M (R 1 NCHR 2 x CHR 2 x NR 3 ) in an organic solvent to form a silicon compound, represented by Formula 2 of the second aspect of the present application.
  • a silicon compound represented by Formula 2 of the second aspect of the present application.
  • M is an alkali metal and R 1 to R 4 , x, y, and z are each as defined above in the second aspect of the present application.
  • the fifth aspect of the present application provides a precursor composition for depositing a silicon-containing thin film including the silicon precursor compound according to Formula 1 or Formula 2, but may not be limited thereto.
  • the sixth aspect of the present disclosure provides a method of depositing a silicon-containing thin film using the silicon precursor compound according to Formula 1 or Formula 2, but may not be limited thereto.
  • the silicon-containing thin film deposition may be one deposited by organometallic chemical vapor deposition (MOCVD) or atomic layer deposition (ALD), for example, by atomic layer deposition (ALD) It may be deposited, but may not be limited thereto.
  • MOCVD organometallic chemical vapor deposition
  • ALD atomic layer deposition
  • the silicon oxide thin film and the silicon nitride thin film may be deposited by the atomic layer deposition method using the silicon precursor compound according to Chemical Formula 1 or Chemical Formula 2.
  • the silicon oxide thin film and the silicon nitride thin film are each independently a gas supply of a silicon precursor compound according to Formula 1 or Formula 2-purge gas supply-oxygen source gas supply-cycle of purge gas supply, or the formula 1 or Formula 2 And a conventional time division atomic layer deposition method and apparatus for repeating the cycle of gas supply of the silicon precursor compound-purge gas supply-nitrogen source gas supply-purge gas supply.
  • oxygen source gas examples include oxygen (O 2 ); Oxygen radicals (eg, radicals generated by O, OH, or plasma); Ozone (O 3 ); NO, N 2 O, or NO 2 ; Moisture (H 2 O) or H 2 O 2 may be used, but may not be limited thereto.
  • the nitrogen source gas may be ammonia (NH 3 ), plasma-activated ammonia, or a plasma-activated mixture of hydrogen (H 2 ) and nitrogen (N 2 ), but may not be limited thereto.
  • n-hexane n-hexane, C 6 H 14
  • the n-hexane extract was filtered through a Celite pad and a glass frit to remove the solvent under reduced pressure and distilled under reduced pressure to obtain a colorless liquid silicone precursor compound 1 represented by Formula 3 below.
  • a silicon oxide thin film and a silicon nitride thin film were deposited by atomic layer deposition.
  • the silicon oxide thin film and the silicon nitride thin film are each independently a cycle of gas supply of the silicon precursor compound 1-purge gas supply-oxygen source gas supply-purge gas supply, or gas supply of the silicon precursor compound 1-purge gas supply -Nitrogen feed gas feed-A conventional time division atomic layer deposition method and apparatus was used which repeats the cycle of purge gas feed.
  • the oxygen source gas is oxygen (O 2 ); Oxygen radicals (eg, radicals generated by O, OH, or plasma); Ozone (O 3 ); NO, N 2 O, or NO 2 ; Moisture (H 2 O) or H 2 O 2 can be used.
  • oxygen oxygen
  • Oxygen radicals eg, radicals generated by O, OH, or plasma
  • Ozone O 3
  • NO, N 2 O, or NO 2 NO 2
  • Moisture (H 2 O) or H 2 O 2 can be used.
  • nitrogen source gas ammonia (NH 3 ), plasma-activated ammonia, or plasma-activated hydrogen (H 2 ) and nitrogen (N 2 ) may be used.
  • n-hexane n-hexane, C 6 H 14
  • the n-hexane extract was filtered through a celite pad and a glass frit, and the filtrate was removed under reduced pressure, and distilled under reduced pressure to obtain a colorless liquid silicone precursor compound 2 represented by the following formula (4).
  • a silicon oxide thin film and a silicon nitride thin film were deposited by atomic layer deposition.
  • the silicon oxide thin film and the silicon nitride thin film were processed in the same manner as the deposition method of the silicon-containing thin film of Example 1, except that the silicon precursor compound 2 was used.
  • n-hexane n-hexane, C 6 H 14
  • the n-hexane extract was filtered through a celite pad and a glass frit, and the filtrate was removed under reduced pressure and distilled under reduced pressure to obtain a colorless liquid silicone precursor compound 3 represented by the following formula (5).
  • a silicon oxide thin film and a silicon nitride thin film were deposited by atomic layer deposition.
  • the silicon oxide thin film and the silicon nitride thin film were processed in the same manner as the deposition method of the silicon-containing thin film of Example 1, except that the silicon precursor compound 3 was used.
  • n-hexane C 6 H 14
  • the n-hexane extract was filtered through a pad of celite and a glass frit, and the filtrate was removed under reduced pressure, and distilled under reduced pressure to obtain a colorless liquid silicone precursor compound 4 represented by the following formula (6).
  • a silicon oxide thin film and a silicon nitride thin film were deposited by atomic layer deposition.
  • the silicon oxide thin film and the silicon nitride thin film were processed in the same manner as the deposition method of the silicon-containing thin film of Example 1, except that the silicon precursor compound 4 was used.
  • Thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) tests were performed to analyze the basic thermal properties of the silicon compounds 1 to 4 prepared in the above examples. At this time, the weight of each sample was taken to about 5 mg and placed in an alumina sample container and measured up to 500 °C at a temperature increase rate of 10 °C / min, the measured results are shown in Figures 1 to 8.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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  • Inorganic Chemistry (AREA)

Abstract

La présente invention concerne des composés de précurseur de silicium et un procédé de production desdits composés de précurseur de silicium, des composés de précurseur pour déposer un film mince contenant du silicium comprenant les composés de précurseur de silicium, et un procédé de dépôt de film mince contenant du silicium à l'aide desdits composés de précurseur.
PCT/KR2013/010720 2012-11-27 2013-11-25 Composés de précurseur de silicium et procédé de dépôt de film mince contenant du silicium l'utilisant WO2014084557A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2012-0135483 2012-11-27
KR1020120135483A KR20140067786A (ko) 2012-11-27 2012-11-27 실리콘 전구체 화합물, 및 상기 전구체 화합물을 이용한 실리콘-함유 박막의 증착 방법

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Cited By (1)

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CN112813416A (zh) * 2019-09-25 2021-05-18 秀博瑞殷株式公社 薄膜制造方法

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KR101787204B1 (ko) * 2015-11-23 2017-10-18 주식회사 한솔케미칼 원자층 증착용(ald) 유기금속 전구체 화합물 및 이를 이용한 ald 증착법
KR102347201B1 (ko) * 2017-10-25 2022-01-04 한국화학연구원 실리콘 아미노아미드 이미드 화합물, 이의 제조방법 및 이를 이용하여 박막을 형성하는 방법
KR102157137B1 (ko) 2018-11-30 2020-09-17 주식회사 한솔케미칼 실리콘 전구체 및 이를 이용한 실리콘 함유 박막의 제조방법
WO2020111405A1 (fr) * 2018-11-30 2020-06-04 주식회사 한솔케미칼 Précurseur de silicium et procédé de fabrication de couche mince contenant du silicium l'utilisant

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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