WO2014189340A1 - Nouveau composé ruthénium, son procédé de fabrication, composition de précurseur destiné au dépôt d'un film le comprenant, et procédé de dépôt de film l'utilisant - Google Patents

Nouveau composé ruthénium, son procédé de fabrication, composition de précurseur destiné au dépôt d'un film le comprenant, et procédé de dépôt de film l'utilisant Download PDF

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Publication number
WO2014189340A1
WO2014189340A1 PCT/KR2014/004667 KR2014004667W WO2014189340A1 WO 2014189340 A1 WO2014189340 A1 WO 2014189340A1 KR 2014004667 W KR2014004667 W KR 2014004667W WO 2014189340 A1 WO2014189340 A1 WO 2014189340A1
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ruthenium
group
formula
ruthenium compound
iso
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PCT/KR2014/004667
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English (en)
Korean (ko)
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한원석
김소영
이미희
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주식회사 유피케미칼
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Priority claimed from KR1020140062819A external-priority patent/KR20140138085A/ko
Publication of WO2014189340A1 publication Critical patent/WO2014189340A1/fr

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    • 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
    • C23C16/18—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 from metallo-organic compounds
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium compounds

Definitions

  • the present application relates to a novel ruthenium compound, a method for producing the ruthenium compound, a precursor composition for film deposition including the ruthenium compound, and a method for depositing a film using the precursor composition.
  • ruthenium is used to minimize leakage current. It is necessary to use an electrode.
  • ruthenium metal Since ruthenium metal is excellent in adhesion to copper metal and difficult to form a solid solution with Cu, it is actively applied to seed layer in Cu wiring process using electroplating during semiconductor manufacturing process. Is being studied.
  • RuO 2 ruthenium oxide
  • ⁇ bulk 46 ⁇ ⁇ cm
  • thermal stability 800 ° C.
  • Application as a lower electrode is a potent material.
  • ruthenium metals and ruthenium oxides have excellent step coverage on uneven surfaces for use as capacitor electrodes in next generation electronic devices that are becoming extremely fine, especially DRAM (Dynamic Random Access Memory) devices with high step ratios.
  • DRAM Dynamic Random Access Memory
  • a liquid at room temperature and having a relatively high vapor pressure using 2,4- (dimethylpentadienyl) (ethylcyclopentadienyl) ruthenium [2,4- (dimethylpentadienyl) (ethylcyclopentadienyl) Ru, DER] and an oxygen-containing gas Atomic layer deposition is also known.
  • 2,4- (dimethylpentadienyl) (ethylcyclopentadienyl) ruthenium [2,4- (dimethylpentadienyl) (ethylcyclopentadienyl) Ru, DER] and an oxygen-containing gas Atomic layer deposition is also known.
  • film growth per raw material supply cycle is only 0.034 nm / cycle ["Investigation on the Growth Initiation of Ru Thin Films by Atomic Layer Deposition” Chemistry of Materials, volume 22, 2850-2856 (2010)].
  • the present application is to provide a novel ruthenium compound, a method for producing the ruthenium compound, a precursor composition for film deposition comprising the ruthenium compound, and a method for depositing a film using the precursor composition.
  • a first aspect of the present application provides a ruthenium compound, represented by the following Chemical Formula 1:
  • R 1 and R 2 each independently include H or C 1-5 linear or branched alkyl groups.
  • the second aspect of the present application is represented as a RuX 2 (p-cymene)] compound represented by the following formula ( 2 ), M 2 CO 3 , in an organic solvent containing an alcohol having 5 or less carbon atoms.
  • a method for preparing a ruthenium compound according to the first aspect of the present application comprising reacting a mixture containing a carbonate salt of an alkali metal and a diazadiene ligand represented by the following general formula (3) to obtain a ruthenium compound of the general formula (1) to provide:
  • M comprises Li, Na, or K
  • X comprises Cl, Br, or I
  • R 1 and R 2 each independently include H or C 1-5 linear or branched alkyl groups.
  • the third aspect of the present application is represented by the [RuX 2 (p-cymene)] 2 compound, the alkali metal (M) and the following formula
  • a process for preparing a ruthenium compound according to the first aspect of the present application comprising reacting a mixture containing a diazadiene ligand to obtain a ruthenium compound of Formula 1:
  • M comprises Li, Na, or K
  • X comprises Cl, Br, or I
  • R 1 and R 2 each independently include H or C 1-5 linear or branched alkyl groups.
  • a fourth aspect of the present application provides a ruthenium-containing film or precursor composition for thin film deposition, comprising the ruthenium compound according to the first aspect of the present application.
  • the fifth aspect of the present application provides a method of depositing a ruthenium-containing film or thin film using the ruthenium-containing film or precursor composition for thin film deposition according to the fourth aspect of the present application.
  • a ruthenium compound and a method for preparing the same are much faster than a conventional ruthenium precursor compound used as a precursor of atomic layer deposition or chemical vapor deposition, per film feed cycle of a raw material gas of atomic layer deposition.
  • the novel ruthenium compounds according to one embodiment of the present disclosure can be used to form ruthenium-containing films or thin films and can be easily mass produced from commercial raw materials.
  • DSC differential scanning calorimetry
  • 3A-3D are images of cross-sectional Scanning Electron Microscopy (SEM) of ruthenium-containing thin films formed according to Example 2 herein.
  • Example 4 is a result of Auger analysis of a ruthenium-containing thin film formed on a silicon (Si) substrate according to Example 2 of the present application.
  • Example 5 is a result of OJ analysis of a ruthenium-containing thin film formed on a titanium nitride (TiN) substrate according to Example 2 of the present application.
  • step to or “step of” does not mean “step for.”
  • 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 1-10 or C 1-5 alkyl groups, for example, methyl, ethyl, propyl, Butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, or all possible isomers thereof may be included, but may not be limited thereto.
  • alkali metal refers to a metal belonging to Group 1 of the periodic table, and may be Li, Na, K, Rb, or Cs, but may not be limited thereto.
  • halogen refers to an element belonging to Group 17 of the periodic table, which may be F, Cl, Br or I, but may not be limited thereto.
  • a first aspect of the present application provides a ruthenium compound, represented by the following Chemical Formula 1:
  • R 1 and R 2 each independently include H or C 1-5 linear or branched alkyl groups.
  • ruthenium by chemical vapor deposition (CVD) or atomic layer deposition (ALD) using the novel ruthenium compound itself or a composition comprising the novel ruthenium compound It is possible to deposit a thin film containing.
  • CVD chemical vapor deposition
  • ALD atomic layer deposition
  • 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, sec-butyl group, tert-butyl group, n-pentyl group, iso-pentyl group, sec-pentyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, and may include those selected from the group consisting of isomers thereof However, this may not be limited.
  • R 1 and R 2 may be an iso-propyl group or tert-butyl group, but may not be limited thereto.
  • HNCHCHNH in the diazadiene ligand may be abbreviated as H-DAD
  • MeNCHCHNMe may be abbreviated as Me-DAD
  • EtNCHCHNEt may be abbreviated as Et-DAD
  • n PrNCHCHN n Pr is abbreviated as n Pr-DAD I PrNCHCHN i Pr may be abbreviated as i Pr-DAD
  • n BuNCHCHN n Bu may be abbreviated as n Bu-DAD
  • t BuNCHCHN t Bu may be abbreviated as t Bu-DAD
  • sec BuNCHCHN sec Bu may be abbreviated as sec Bu-DAD.
  • the second aspect of the present application is represented by the compound [RuX 2 (p-cymene)] 2 represented by the following Chemical Formula 2, M 2 CO 3 in an organic solvent containing an alcohol having 5 or less carbon atoms.
  • a method for producing a ruthenium compound according to the first aspect of the present application comprising reacting a mixture containing a carbonate salt of an alkali metal and a diazadiene ligand represented by Formula 3 to obtain a ruthenium compound of Formula 1 Provides:
  • M comprises Li, Na, or K
  • X comprises Cl, Br, or I
  • R 1 and R 2 each independently include H or C 1-5 linear or branched alkyl groups.
  • the reaction for obtaining the ruthenium compound of Formula 1 may be a reflux reaction, but may not be limited thereto.
  • the organic solvent may include a primary alcohol or a secondary alcohol having 5 or less carbon atoms, but may not be limited thereto.
  • the primary alcohol or secondary alcohol having 5 or less carbon atoms may serve as a solvent and also act as a reducing agent.
  • ruthenium compounds according to one embodiment of the present application can be prepared in an economical and simple process that does not require a separate reducing agent.
  • the primary alcohol or secondary alcohol having 5 or less carbon atoms is methanol, ethanol, n-propyl alcohol, iso-propyl alcohol, n-butanol, iso-butanol, n-pentanol, iso- Pentanol, and combinations thereof may be selected from the group consisting of, but may not be limited thereto.
  • M comprises Li, Na, or K
  • X comprises Cl, Br, or I
  • R 1 and R 2 each independently include H or C 1-5 linear or branched alkyl groups.
  • the reaction for obtaining the ruthenium compound of Formula 1 may be a reflux reaction, but may not be limited thereto.
  • the organic solvent includes an ether selected from the group consisting of dimethyl ether, diethyl ether, dipropyl ether, ethylene glycol dimethyl ether (DME), and ethylene glycol diethyl ether. It may be, but may not be limited thereto.
  • the [RuX 2 (p-cymene)] 2 compound represented by Chemical Formula 2 may be a ruthenium trihalide hydrate ( It is prepared by a method comprising reacting a mixture containing RuX 3 ⁇ nH 2 O) and ⁇ -terpinene represented by the following formula (4) or ⁇ -terpinene represented by the following formula (5): It may be, but may not be limited thereto.
  • ⁇ -terpinene, ⁇ -terpinene, ⁇ -Phellandrene, ⁇ -phellandrene, or an isomer thereof may be used instead of the ⁇ -terpinene or ⁇ -terpinene.
  • X is Cl, Br, or I
  • n is an integer of 0 or 10 or less.
  • the ruthenium trihalide hydrate (RuX 3 ⁇ nH 2 O) and ⁇ -terpinene of the formula (4) or ⁇ -terpinene of the formula (5) are alcohols. It may be added to an organic solvent containing and reacted to form the compound [RuX 2 (p-cymene)] 2 . Then, as in Scheme 1 or 2, the formed [RuX 2 (p-cymene)] 2 compound; Carbonate salts of alkali metals (M 2 CO 3 ) or alkali metals; And reflux reaction of the mixture containing the diazadiene ligand to prepare a ruthenium compound represented by Chemical Formula 1.
  • a fourth aspect of the present application provides a ruthenium-containing film or precursor composition for thin film deposition, comprising the ruthenium compound according to the first aspect of the present application.
  • the fifth aspect of the present application provides a method of depositing a ruthenium-containing film or a thin film using the ruthenium compound according to the first aspect of the present application or the ruthenium-containing film or the precursor composition for thin film deposition.
  • the ruthenium-containing film may be a nanometer-thick thin film, but is not limited thereto.
  • depositing the ruthenium-containing film may be performed by organometallic chemical vapor deposition (MOCVD) or atomic layer deposition (ALD), but may not be limited thereto.
  • MOCVD organometallic chemical vapor deposition
  • ALD atomic layer deposition
  • depositing the ruthenium-containing film comprises contacting a substrate including a ruthenium compound according to the first aspect of the present disclosure or a precursor composition for depositing a ruthenium-containing film according to the third aspect to a substrate surface. It may be carried out by a process comprising the.
  • depositing the ruthenium-containing film comprises contacting a substrate comprising a ruthenium compound according to the first aspect of the present application or a precursor composition for ruthenium-containing film deposition according to the third aspect to a substrate. And at the same time or alternately may be carried out by a process further comprising contacting the substrate containing the reaction gas to the substrate.
  • the deposition of the ruthenium-containing film may include alternately applying a gas and a reaction gas including a ruthenium compound according to the first aspect of the present disclosure or a ruthenium-containing film deposition composition according to the third aspect to the substrate surface.
  • Atomic layer deposition (ALD) methods may be used, but may not be limited thereto.
  • depositing the ruthenium-containing film comprises simultaneously contacting a substrate surface with a gas and a reaction gas comprising a ruthenium compound according to the first aspect of the present application or a precursor composition for ruthenium-containing film deposition according to the third aspect.
  • Chemical vapor deposition (CVD) may be used, but the present invention may not be limited thereto.
  • the gas comprising a ruthenium compound according to the first aspect of the present application or a ruthenium-containing film deposition composition according to the third aspect is bubbling, gas phase flow control method
  • the substrate surface may be contacted using a known method such as a direct liquid injection method or a liquid transfer method.
  • the reaction gas used in the ALD and CVD method is a semiconductor such as hydrogen (H 2 ) gas, ammonia (NH 3 ) gas, oxygen (O 2 ) gas, ozone (O 3 ) gas
  • the gas used in the process may be used to form a ruthenium-containing film, but may not be limited thereto.
  • a ruthenium-containing film containing less impurities may be formed.
  • a ruthenium oxide film may be formed, but may not be limited thereto.
  • the ruthenium compound according to the exemplary embodiment of the present invention is a complex in which a weak coordination bond is connected between the ruthenium center metal and the ligand, and thus, decomposition of the ligand may occur well at a relatively low temperature, thereby lowering the deposition temperature.
  • the ligands of p-cymene and diazadiene separated from the ruthenium center metal are easily removed from the reaction chamber through vacuum exhaust, impurities such as carbon, nitrogen, and oxygen are reduced in the deposited thin film, or No impurities remain or substantially no residue.
  • N, N'- diisopropyl-1,4-diaza-1,3-butadiene N, N'- diisopropyl-1,4- diaza-1,3-butadiene, i
  • a solution of 37 g (0.259 mol, 3 equivalents) of Pr-DAD was slowly added to the stirred suspension at room temperature for 3 hours, and then the mixture was refluxed for 15 hours to complete the reaction.
  • the compound for the comparative example was prepared as follows.
  • Boiling point (bp) 105 ° C. (0.3 torr);
  • thermogravimetric analysis TGA
  • DSC differential scanning calorimetry analysis
  • FIG. 1 is a thermal gravimetric analysis (TGA) graph of ruthenium compound prepared according to Example 1
  • FIG. 2 is a differential scanning calorimetry (DSC) graph of ruthenium compound prepared according to Example 1.
  • TGA thermal gravimetric analysis
  • DSC differential scanning calorimetry
  • Example 2 Formation of ruthenium-containing thin film by atomic layer deposition using (p-cymene) ( i Pr-DAD) Ru and oxygen (O 2 ) gas prepared in Example 1
  • Substrates used for deposition include a silicon (Si) wafer, a wafer coated with a silicon oxide (SiO 2 ) film on the silicon substrate as 100 nm thick, a wafer coated with a silicon nitride (SiN) film on a silicon substrate as 50 nm thick, and a silicon substrate A wafer in which a titanium nitride (TiN) film was coated as 50 nm thick was used.
  • the temperature of the substrate was adjusted to 250 °C and the precursor is placed in a container of stainless steel (stainless steel) material using argon gas having a flow rate of 60 sccm as a carrier gas of the precursor while heating the vessel at a temperature of 120 °C It was fed to the substrate surface in a gaseous state.
  • the working pressure of the reactor was adjusted to 0.5 torr, and ruthenium precursor gas and oxygen (O 2 ) gas were alternately contacted with the substrate placed in the atomic layer deposition chamber. The oxygen gas was flowed at 60 sccm.
  • FIGS. 3A-3D are images of cross-sectional Scanning Electron Microscopy (SEM) of ruthenium-containing thin films formed according to Example 2, and FIG. 4 is on a silicon (Si) substrate according to Example 2 Auger analysis result of the formed ruthenium-containing thin film (Auger) analysis, Figure 5 is a result of the ozone analysis of the ruthenium-containing thin film formed on a titanium nitride (TiN) substrate according to this embodiment. As can be seen from Figures 3a to 3d, it was confirmed that even on Si and SiO 2 substrates, a film having a flat surface having almost no difference with TiN was obtained.
  • SEM Scanning Electron Microscopy
  • the terpinene compound used as a starting material in Preparation Example 1 can be easily obtained commercially even at a large capacity of several tens of Kg or hundreds of Kg. Therefore, the ruthenium compound of Example 1 synthesized from the terpinene can be easily mass-produced from commercial raw materials, and is liquid at room temperature, which is very advantageous for industrial use for the purpose of depositing a film containing Ru.
  • novel ruthenium compounds according to the present invention can be easily mass-produced from commercial raw materials, and are liquid at room temperature, which is very advantageous for industrial use for the purpose of depositing a film containing Ru.

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  • Engineering & Computer Science (AREA)
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Abstract

La présente invention concerne un nouveau composé ruthénium, un procédé de fabrication du composé ruthénium, une composition de précurseur pour le dépôt d'un film, la composition de précurseur comprenant le composé ruthénium, et un procédé de dépôt d'un film utilisant la composition de précurseur.
PCT/KR2014/004667 2013-05-24 2014-05-26 Nouveau composé ruthénium, son procédé de fabrication, composition de précurseur destiné au dépôt d'un film le comprenant, et procédé de dépôt de film l'utilisant WO2014189340A1 (fr)

Applications Claiming Priority (4)

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KR20130059234 2013-05-24
KR10-2013-0059234 2013-05-24
KR10-2014-0062819 2014-05-26
KR1020140062819A KR20140138085A (ko) 2013-05-24 2014-05-26 신규 루테늄 화합물, 이의 제조 방법, 이를 포함하는 막 증착용 전구체 조성물, 및 이를 이용하는 막의 증착 방법

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150056384A1 (en) * 2012-02-07 2015-02-26 L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Method for the deposition of a ruthenium containing film using arene diazadiene ruthenium(0) precursors
CN112292383A (zh) * 2018-07-27 2021-01-29 优美科股份公司及两合公司 金属有机化合物
US11643425B2 (en) * 2018-07-27 2023-05-09 Umicore Ag & Co. Kg Organometallic compounds for the manufacture of a semiconductor element or electronic memory

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KR20100060482A (ko) * 2008-11-27 2010-06-07 주식회사 유피케미칼 루테늄 금속 또는 루테늄 산화물 박막 증착용 유기 금속 전구체 화합물 및 이를 이용한 박막 증착 방법
KR20100071463A (ko) * 2008-12-19 2010-06-29 주식회사 유피케미칼 금속 박막 또는 금속 산화물 박막 증착용 유기금속 전구체 화합물 및 이를 이용한 박막 증착 방법
WO2013117955A1 (fr) * 2012-02-07 2013-08-15 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Procédé de dépôt d'un film contenant du ruthénium au moyen de précurseurs arène diazadiène ruthénium(0)

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KR20100060482A (ko) * 2008-11-27 2010-06-07 주식회사 유피케미칼 루테늄 금속 또는 루테늄 산화물 박막 증착용 유기 금속 전구체 화합물 및 이를 이용한 박막 증착 방법
KR20100071463A (ko) * 2008-12-19 2010-06-29 주식회사 유피케미칼 금속 박막 또는 금속 산화물 박막 증착용 유기금속 전구체 화합물 및 이를 이용한 박막 증착 방법
WO2013117955A1 (fr) * 2012-02-07 2013-08-15 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Procédé de dépôt d'un film contenant du ruthénium au moyen de précurseurs arène diazadiène ruthénium(0)

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
US20150056384A1 (en) * 2012-02-07 2015-02-26 L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Method for the deposition of a ruthenium containing film using arene diazadiene ruthenium(0) precursors
US9416443B2 (en) * 2012-02-07 2016-08-16 L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Method for the deposition of a ruthenium containing film using arene diazadiene ruthenium(0) precursors
CN112292383A (zh) * 2018-07-27 2021-01-29 优美科股份公司及两合公司 金属有机化合物
US11643425B2 (en) * 2018-07-27 2023-05-09 Umicore Ag & Co. Kg Organometallic compounds for the manufacture of a semiconductor element or electronic memory

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