WO2012018086A1 - Composé bis(dialkylamide) de magnésium et procédé pour la production d'un film mince contenant du magnésium à l'aide du composé du magnésium - Google Patents

Composé bis(dialkylamide) de magnésium et procédé pour la production d'un film mince contenant du magnésium à l'aide du composé du magnésium Download PDF

Info

Publication number
WO2012018086A1
WO2012018086A1 PCT/JP2011/067880 JP2011067880W WO2012018086A1 WO 2012018086 A1 WO2012018086 A1 WO 2012018086A1 JP 2011067880 W JP2011067880 W JP 2011067880W WO 2012018086 A1 WO2012018086 A1 WO 2012018086A1
Authority
WO
WIPO (PCT)
Prior art keywords
magnesium
compound
dialkylamide
group
general formula
Prior art date
Application number
PCT/JP2011/067880
Other languages
English (en)
Japanese (ja)
Inventor
藤村　整
宏樹 金戸
Original Assignee
宇部興産株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 宇部興産株式会社 filed Critical 宇部興産株式会社
Priority to KR1020137005201A priority Critical patent/KR20130136445A/ko
Priority to JP2012527770A priority patent/JP5817727B2/ja
Publication of WO2012018086A1 publication Critical patent/WO2012018086A1/fr

Links

Images

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/65—Metal complexes of amines
    • 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/02—Magnesium 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
    • C23C16/22—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
    • C23C16/403—Oxides of aluminium, magnesium or beryllium

Definitions

  • the present invention relates to a novel magnesium bis (dialkylamide) compound and a method for producing a magnesium-containing thin film by a chemical vapor deposition method (hereinafter referred to as a CVD method) using the magnesium compound.
  • magnesium compound for producing a magnesium-containing thin film various types of magnesium compounds such as alkyl magnesium, magnesium alkoxide, magnesium diketonate have been studied (for example, see Patent Documents 1 and 2). Among them, bis (cyclopentadienyl) magnesium and related compounds are mainly used.
  • Patent Document 3 As raw materials for forming other metal-containing thin films such as titanium-containing thin films, zirconium-containing thin films, hafnium-containing thin films, and aluminum-containing thin films, compounds having a dialkylamide ligand have been proposed (Patent Document 3). reference).
  • Magnesium bis (dialkylamide) compounds are also known, and are used, for example, as polymerization catalysts, raw materials for producing pharmaceuticals, agricultural chemicals, and the like (see, for example, Non-Patent Document 1 and Patent Document 4).
  • magnesium compounds are not necessarily optimal in the production of magnesium-containing thin films, such as vapor pressure, thermal stability, and reactivity, and even the most adopted bis (cyclopentadienyl) magnesium contains magnesium. It was difficult to say that the magnesium compound was sufficient to produce a thin film. Therefore, a magnesium compound that satisfies all physical properties such as vapor pressure, thermal stability, and reactivity has been demanded.
  • An object of the present invention is to provide an industrially suitable magnesium compound, more specifically, production of a magnesium-containing thin film by a CVD method, which can solve the above-mentioned problems and can produce a magnesium-containing thin film by a simple method.
  • the present invention provides a magnesium compound suitable for the above.
  • Another object of the present invention is to provide a method for producing a magnesium-containing thin film using the magnesium compound.
  • the present invention relates to the following matters.
  • R 1 represents an isopropyl group or a branched alkyl group having 4 to 6 carbon atoms
  • R 2 represents a linear or branched alkyl group having 1 to 5 carbon atoms, provided that R 1 and R 2 are both isopropyl groups, R 1 and R 2 are both isobutyl groups, and R 1 is an isopropyl group and R 2 is a methyl group.
  • R 3 and R 4 may be the same or different and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms.
  • R 1 represents an isopropyl group or a branched alkyl group having 4 to 6 carbon atoms
  • R 2 represents a linear or branched alkyl group having 1 to 5 carbon atoms, provided that R 1 and R 2 are both isopropyl groups, R 1 and R 2 are both isobutyl groups, and R 1 is an isopropyl group and R 2 is a methyl group.
  • R 1 represents an isopropyl group or a branched alkyl group having 4 to 6 carbon atoms
  • R 2 represents a linear or branched alkyl group having 1 to 5 carbon atoms, provided that R 1 and R 2 are both isopropyl groups, R 1 and R 2 are both isobutyl groups, and R 1 is an isopropyl group and R 2 is a methyl group.
  • a novel magnesium bis (dialkylamide) compound particularly suitable for film formation by the CVD method.
  • a magnesium compound Using the magnesium compound, a magnesium-containing thin film can be produced with good film forming characteristics by a CVD method.
  • the magnesium bis (dialkylamide) compound of the present invention is represented by the general formula (1).
  • R 1 represents an isopropyl group or a branched alkyl group having 4 to 6 carbon atoms such as t-butyl group, t-pentyl group or neopentyl group
  • R 2 represents a methyl group
  • R 1 and R 2 are both isopropyl groups
  • R 1 and R 2 are both isobutyl groups
  • R 1 is an isopropyl group and R 2 is a methyl group.
  • Two R 1 may be different, two R 2 may be different, but the two R 1 are the same, since the two R 2 may be the same compound can be relatively easily synthesized, preferable.
  • R 1 is a branched alkyl group having 4 to 5 carbon atoms
  • R 2 is a linear or branched alkyl group having 1 to 5 carbon atoms.
  • R 1 is particularly preferably a t-butyl group, a t-pentyl group, or a neopentyl group.
  • R 2 is particularly preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, a t-pentyl group, or a neopentyl group.
  • R 1 is a t-butyl group, a t-pentyl group, more preferably a t-butyl group
  • R 2 is a linear or branched alkyl group having 1 to 5 carbon atoms, more preferably a methyl group.
  • Ethyl group isopropyl group, t-butyl group, t-pentyl group, and neopentyl group.
  • magnesium bis (dialkylamide) compound of the present invention examples include compounds represented by the following formulas (6) to (20).
  • the synthesis of the magnesium bis (dialkylamide) compound of the present invention can be carried out by the following method (A) or (B) (hereinafter also referred to as the reaction of the present invention).
  • R 1 and R 2 are as defined above, and R 3 and R 4 represent a linear or branched alkyl group having 1 to 10 carbon atoms. R 3 and R 4 are the same. Or they may be different, and X represents a halogen atom.
  • Method (A) is a method of synthesizing a magnesium bis (dialkylamide) compound by reacting a dialkylmagnesium compound with a dialkylamine.
  • the dialkylmagnesium compound used in the reaction (A) of the present invention is represented by the general formula (2).
  • R 3 and R 4 are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, t-pentyl group.
  • R 3 and R 4 may be the same or different.
  • dialkylmagnesium compound used in the reaction (A) of the present invention a commercially available product can be used, and it can be produced from metallic magnesium by a known method.
  • di (n-butyl) magnesium or n-butylethylmagnesium is preferably used.
  • the dialkylamine used in the reaction (A) of the present invention is represented by the general formula (3).
  • R 1 and R 2 correspond to R 1 and R 2 in the formula (1), respectively, and have the same meanings as described above.
  • the dialkylamine used in the reaction (A) of the present invention includes t-butylmethylamine, t-butylethylamine, t-butylisopropylamine, di-t-butylamine, t-butyl-t-pentylamine, di- -T-pentylamine and the like are preferable.
  • the amount of the dialkylamine used is preferably 1.5 to 3.0 mol, more preferably 1.8 to 2.2 mol, per 1 mol of dialkylmagnesium.
  • the reaction (A) of the present invention is preferably performed in an organic solvent.
  • the organic solvent used is not particularly limited as long as it does not inhibit the reaction.
  • ethers such as diethyl ether, tetrahydrofuran, dimethoxyethane, and dioxane
  • aliphatics such as hexane, heptane, cyclohexane, methylcyclohexane, and ethylcyclohexane
  • hydrocarbons include aromatic hydrocarbons such as toluene and xylene, and ethers, aliphatic hydrocarbons, and mixed solvents of ethers and aliphatic hydrocarbons are preferably used.
  • the amount of the organic solvent used is preferably 1 to 100 g, more preferably 1 to 10 g, with respect to 1 g of dialkyl magnesium.
  • the reaction (A) of the present invention is performed by, for example, a method of mixing a dialkylmagnesium compound, a dialkylamine and an organic solvent and reacting them with stirring.
  • the reaction temperature at that time is preferably ⁇ 20 to 120 ° C., more preferably 0 to 100 ° C., and the reaction pressure is not particularly limited.
  • Method (B) is a method of synthesizing a magnesium bis (dialkylamide) compound by reacting lithium dialkylamide synthesized from dialkylamine and alkyllithium with dihalogenomagnesium.
  • the dialkylamine used in the reaction (B) of the present invention is represented by the general formula (3).
  • R 1 and R 2 correspond to R 1 and R 2 in the formula (1), respectively, and have the same meanings as described above.
  • the alkyl lithium used in the reaction (B) of the present invention is not particularly limited, and examples thereof include methyl lithium, ethyl lithium, n-butyl lithium, s-butyl lithium, t-butyl lithium, etc., preferably n- Butyl lithium is used.
  • the amount of the alkyl lithium used is preferably 0.8 to 1.2 mol, more preferably 0.9 to 1.1 mol, per 1 mol of dialkylamine.
  • lithium dialkylamide is synthesized from dialkylamine and alkyllithium, and this lithium dialkylamide is reacted with dihalogenomagnesium.
  • the dihalogeno magnesium used in the reaction (B) of the present invention is represented by the general formula (5).
  • X represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a chlorine atom.
  • the amount of dihalogenomagnesium used is preferably 0.3 to 0.6 mol, more preferably 0.45 to 0.55 mol, per 1 mol of dialkylamine.
  • the amount of lithium dialkylamide used is preferably 1.5 to 3.0 mol, more preferably 1.8 to 2.2 mol, per 1 mol of dihalogenomagnesium. .
  • the reaction (B) of the present invention is preferably performed in an organic solvent.
  • the organic solvent used is not particularly limited as long as it does not inhibit the reaction.
  • ethers such as diethyl ether, tetrahydrofuran, dimethoxyethane, and dioxane
  • aliphatics such as hexane, heptane, cyclohexane, methylcyclohexane, and ethylcyclohexane
  • hydrocarbons include aromatic hydrocarbons such as toluene and xylene, and ethers, aliphatic hydrocarbons, and mixed solvents of ethers and aliphatic hydrocarbons are preferably used.
  • the amount of the organic solvent used is preferably 1 to 100 g, more preferably 1 to 10 g, with respect to 1 g of dialkylamine.
  • the amount of the organic solvent used in the reaction of lithium dialkylamide with dihalogenomagnesium is preferably 1 to 100 g, more preferably 1 to 10 g, relative to 1 g of dihalogenomagnesium. is there.
  • a dialkylamine, an alkyllithium and an organic solvent are mixed and reacted with stirring to synthesize a lithium dialkylamide compound, and then a dihalogenomagnesium is added and further reacted with stirring. Or isolating the synthesized lithium dialkylamide, and then mixing the resulting lithium dialkylamide, dihalogenomagnesium and an organic solvent and reacting with stirring.
  • the reaction temperature at that time is preferably ⁇ 20 to 100 ° C., more preferably 0 to 50 ° C., and the reaction pressure is not particularly limited.
  • the lithium dialkylamide compound may be isolated once before the reaction with dihalogenomagnesium or may not be used, and the reaction solution may be used as it is, and the organic solvent may be changed, removed and / or added as appropriate. You may do it.
  • the target magnesium bis (dialkylamide) compound is obtained by the reaction (A) or (B) of the present invention.
  • the synthesized magnesium bis (dialkylamide) compound is isolated and purified by a known method such as extraction, filtration, concentration, distillation, sublimation, recrystallization, column chromatography, etc. after completion of the reaction.
  • the magnesium bis (dialkylamide) compound which is the object of the present invention, and the dialkylmagnesium used in the production thereof are often unstable with respect to moisture and oxygen in the atmosphere. It is desirable to perform a reaction operation or a post-treatment of the reaction solution under gas conditions.
  • a magnesium-containing thin film can be formed with good film forming characteristics, for example, by the CVD method.
  • a method for vapor-depositing a magnesium-containing thin film on a film formation target it can be performed by a known CVD method or atomic layer deposition method (ALD method), for example, magnesium bis (dialkylamide) under normal pressure or reduced pressure.
  • Compound vapor as an oxygen source eg, oxidizing gas such as oxygen or ozone; water; alcohols such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butanol
  • reducing gas eg, hydrogen gas or It is possible to use a method of depositing a magnesium-containing thin film by feeding onto a film-forming target heated together with ammonia gas or a mixed gas thereof. Note that these gases (including vaporized liquids) may be diluted with an inert gas or the like.
  • a magnesium-containing thin film can be deposited by plasma CVD using the same raw material supply.
  • magnesium bis (dialkylamide) compound for thin film formation.
  • a method for vaporizing the magnesium bis (dialkylamide) compound used in the present invention for example, magnesium bis (dialkylamide) is used.
  • (Amide) compound itself is not only filled into the vaporization chamber or transported and vaporized, but also magnesium bis (dialkylamide) compound in a suitable solvent (eg hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, heptane, octane, etc.)
  • a suitable solvent eg hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, heptane, octane, etc.
  • Aromatic hydrocarbons such as toluene, ethylbenzene, xylene, etc .
  • ethers such as glyme, diglyme, triglyme, dioxane, tetrahydrofuran, etc.
  • the deposition conditions are, for example, that the pressure in the reaction system is preferably 1 Pa to 200 kPa, more preferably 10 Pa to 110 kPa.
  • the film object temperature is preferably 50 to 900 ° C., more preferably 100 to 600 ° C., and the temperature for vaporizing the magnesium bis (dialkylamide) compound is preferably 30 to 250 ° C., more preferably 60 to 200 ° C. .
  • an oxygen source for example, oxidizing gas, water vapor or alcohol vapor, or a mixed gas thereof
  • a reducing gas for example, hydrogen gas or ammonia gas, or these gases
  • the content ratio of the mixed gas is preferably 3 to 99% by volume, more preferably 5 to 98% by volume.
  • Example 1 (Method (A); synthesis of magnesium bis (t-butylmethylamide) (compound (6)))
  • metal magnesium 5.5 g (0.23 mol)
  • diethyl ether 20 ml
  • diethyl ether 25 g (0.18 mol)
  • bromobutane 25 g (0.18 mol)
  • Magnesium bis (t-butylmethylamide) was a novel compound represented by the following physical property values.
  • Example 2 (Method (A); synthesis of magnesium bis (t-butylethylamide) (compound (7))
  • the reaction was conducted in the same manner as in Example 1 except that dialkylamine was changed to 11 g (0.11 mol) of t-butylethylamine in Example 1.
  • 5.8 g of magnesium bis (t-butylethylamide) was obtained as a white solid (isolation yield: 52%).
  • Magnesium bis (t-butylethylamide) was a novel compound represented by the following physical property values.
  • Example 3 (Method (B); Synthesis of Magnesium Bis (t-butylisopropylamide) (Compound (8)))
  • 1.8 g (16 mmol) of t-butylisopropylamine and 30 ml of heptane were added in an argon atmosphere.
  • 10 ml (16 mmol) of a 1.6 mol / l n-butyllithium hexane solution was slowly dropped while maintaining the liquid temperature at around 25 ° C., and the mixture was reacted at 25 ° C. for 2 hours with stirring.
  • the reaction solution was concentrated under reduced pressure to obtain 1.7 g of lithium-t-butylisopropylamide (isolation yield: 88%).
  • Magnesium bis (t-butylisopropylamide) was a novel compound represented by the following physical property values.
  • Example 4 Magnesium Bis (t-butyl-t-pentylamide) (Synthesis of Compound (10))
  • a 100 ml flask equipped with a stirrer, a thermometer and a dropping funnel 1.1 g (8.0 mmol) of t-butyl-t-pentylamine and 15 ml of heptane were added to a 100 ml flask equipped with a stirrer, a thermometer and a dropping funnel, and the liquid temperature was 25 ° C.
  • 5.0 ml (8.0 mmol) of a 1.6 mol / l n-butyllithium hexane solution was gently added dropwise and reacted at 25 ° C. for 2 hours with stirring.
  • the reaction solution was concentrated under reduced pressure to obtain 1.1 g of lithium-t-butyl-t-pentylamide (isolated yield; 90%).
  • Magnesium bis (t-butyl-t-pentylamide) was a novel compound represented by the following physical property values.
  • Example 5 (Vapor deposition experiment; Production of magnesium-containing thin film) Using the magnesium bis (t-butylmethylamide) (compound (6)) obtained in Example 1, a vapor deposition experiment by the CVD method was performed to evaluate the film forming characteristics. The apparatus shown in FIG. 1 was used for the vapor deposition experiment. Deposition conditions and film characteristics were as follows.
  • the apparatus shown in FIG. 1 has the following structure.
  • the magnesium compound in the magnesium raw material container (vaporizer) 7 maintained at a constant temperature by the thermostat 8 is heated and vaporized, and leaves the raw material container 7 along with the helium gas introduced through the mass flow controller 4.
  • the gas exiting the raw material container 7 is introduced into the reactor 9 together with the helium gas introduced through the mass flow controller 5.
  • oxygen gas which is a reaction gas, is also introduced into the reactor 9 via the mass flow controller 6.
  • the pressure in the reaction system is monitored by a pressure gauge 12 and controlled to a predetermined pressure by opening and closing a valve in front of the vacuum pump 14.
  • the central part of the reactor 9 has a structure that can be heated by the heater 11.
  • the magnesium compound introduced into the reactor 9 is set in the center of the reactor, and is oxidized and decomposed on the surface of the substrate 10 heated to a predetermined temperature by the heater 11 to form a magnesium-containing thin film on the substrate 10. Is done.
  • the gas exiting the reactor 9 is exhausted to the atmosphere through the trap 13 and the vacuum pump 14.
  • Comparative Example 1 (deposition experiment; production of magnesium-containing thin film) Using bis (cyclopentadienyl) magnesium, a vapor deposition experiment by a CVD method was performed in the same manner as in Example 5 to evaluate the film formation characteristics. Deposition conditions and film characteristics were as follows. In addition, various conditions were adjusted and the amount of raw material supply was equal to Example 5, and the vapor deposition experiment was conducted.
  • magnesium bis (dialkylamide) compound of the present invention a high-quality magnesium-containing thin film (magnesium oxide film) free from impurities such as carbon atoms and nitrogen atoms can be produced. did.
  • an industrially suitable and novel magnesium compound more specifically a magnesium compound suitable for producing a magnesium-containing thin film by a CVD method, which can produce a magnesium-containing thin film by a simple method. I can do it.
  • a method for producing a magnesium-containing thin film on a film formation target using the magnesium compound by a CVD method can be provided.
  • a magnesium bis (dialkylamide) compound is a useful compound as a raw material for producing a magnesium-containing thin film production material, a polymerization catalyst, pharmaceuticals, agricultural chemicals, and the like.

Landscapes

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

Abstract

La présente invention porte sur : un composé bis(dialkylamide) de magnésium représenté par la formule générale (1) (dans laquelle R1 représente un groupe isopropyle ou un groupe alkyle ramifié ayant 4-6 atomes de carbone ; et R2 représente un groupe alkyle linéaire ou ramifié ayant 1-5 atomes de carbone, un cas dans lequel chacun de R1 et R2 représente un groupe isopropyle, un cas dans lequel chacun de R1 et R2 représente un groupe isobutyle et un cas dans lequel R1 représente un groupe isopropyle et R2 représente un groupe méthyle étant exclus) ; et un procédé pour la production d'un film mince contenant du magnésium utilisant le composé du magnésium.
PCT/JP2011/067880 2010-08-06 2011-08-04 Composé bis(dialkylamide) de magnésium et procédé pour la production d'un film mince contenant du magnésium à l'aide du composé du magnésium WO2012018086A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020137005201A KR20130136445A (ko) 2010-08-06 2011-08-04 마그네슘비스(디알킬아미드) 화합물, 및 당해 마그네슘 화합물을 사용하는 마그네슘 함유 박막의 제조 방법
JP2012527770A JP5817727B2 (ja) 2010-08-06 2011-08-04 マグネシウムビス（ジアルキルアミド）化合物、及び当該マグネシウム化合物を用いるマグネシウム含有薄膜の製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010176838 2010-08-06
JP2010-176838 2010-08-06

Publications (1)

Publication Number Publication Date
WO2012018086A1 true WO2012018086A1 (fr) 2012-02-09

Family

ID=45559582

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/067880 WO2012018086A1 (fr) 2010-08-06 2011-08-04 Composé bis(dialkylamide) de magnésium et procédé pour la production d'un film mince contenant du magnésium à l'aide du composé du magnésium

Country Status (4)

Country Link
JP (1) JP5817727B2 (fr)
KR (1) KR20130136445A (fr)
TW (1) TWI504605B (fr)
WO (1) WO2012018086A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63238086A (ja) * 1987-03-13 1988-10-04 リチウム　コーポレーション　オブ　アメリカ エーテルを含まない有機金属アミド組成物
US5892083A (en) * 1997-12-01 1999-04-06 Wayne State University Organometallic source compounds for chemical vapor deposition
DE10061317C1 (de) * 2000-12-08 2002-04-04 Chemetall Gmbh Verfahren zur Herstellung von Magnesium-bis[di(organo)amiden] und deren Verwendung
JP2005126334A (ja) * 2003-10-21 2005-05-19 Mitsubishi Materials Corp 有機金属化合物及び該化合物を含む溶液原料並びに金属酸化膜薄膜
WO2008039960A1 (fr) * 2006-09-28 2008-04-03 Praxair Technology, Inc. Composés organométalliques hétéroleptiques
JP2009536267A (ja) * 2006-05-05 2009-10-08 アプライド マテリアルズ インコーポレイテッド 誘電膜の原子層堆積のための化学物質の光励起のための方法および装置

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4944894A (en) * 1988-02-25 1990-07-31 Lithium Corporatoin Of America Ether free organometallic amide compositions
TW200941596A (en) * 2008-03-19 2009-10-01 Univ Nat Formosa Method for manufacturing manganese-doped zinc-oxide (Mn-doped ZnO) thin film with adjustable energy gap using sol-gel process and spin coating method

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63238086A (ja) * 1987-03-13 1988-10-04 リチウム　コーポレーション　オブ　アメリカ エーテルを含まない有機金属アミド組成物
US5892083A (en) * 1997-12-01 1999-04-06 Wayne State University Organometallic source compounds for chemical vapor deposition
DE10061317C1 (de) * 2000-12-08 2002-04-04 Chemetall Gmbh Verfahren zur Herstellung von Magnesium-bis[di(organo)amiden] und deren Verwendung
JP2005126334A (ja) * 2003-10-21 2005-05-19 Mitsubishi Materials Corp 有機金属化合物及び該化合物を含む溶液原料並びに金属酸化膜薄膜
JP2009536267A (ja) * 2006-05-05 2009-10-08 アプライド マテリアルズ インコーポレイテッド 誘電膜の原子層堆積のための化学物質の光励起のための方法および装置
WO2008039960A1 (fr) * 2006-09-28 2008-04-03 Praxair Technology, Inc. Composés organométalliques hétéroleptiques

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
C.J.ROHBOGNER ET AL., EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no. 11, 2009, pages 1781 - 1795 *
E.C.ASHBY ET AL.: "Reactions of Magnesium Hydrides. 3.Stereoselective Reduction of Cyclic and Bicyclic Ketones by Dialkylaminomagnesium Hydrides", JOURNAL OF ORGANIC CHEMISTRY, vol. 43, no. 8, 1978, pages 1564 - 1566 *

Also Published As

Publication number Publication date
TWI504605B (zh) 2015-10-21
KR20130136445A (ko) 2013-12-12
JPWO2012018086A1 (ja) 2013-10-03
JP5817727B2 (ja) 2015-11-18
TW201223957A (en) 2012-06-16

Similar Documents

Publication Publication Date Title
JP5857970B2 (ja) （アミドアミノアルカン）金属化合物、及び当該金属化合物を用いた金属含有薄膜の製造方法
JP6065840B2 (ja) トリス（ジアルキルアミド）アルミニウム化合物及び当該アルミニウム化合物を用いるアルミニウム含有薄膜の製造方法
EP2053036A1 (fr) Complexe organoruthénique et procédé de production de film mince de ruthénium au moyen du compelxe ruthénique
US10014089B2 (en) Liquid precursor compositions, preparation methods thereof, and methods for forming layer using the composition
JP2015224227A (ja) （アセチレン）ジコバルトヘキサカルボニル化合物の製造方法
JP3321729B2 (ja) トリメチル（エチルシクロペンタジエニル）白金とそ の製造方法及びそれを用いた白金含有薄膜の製造方法
US9556212B2 (en) Chemical deposition raw material formed of ruthenium complex and method for producing the same, and chemical deposition method
WO2013054863A1 (fr) Matière brute pour dépôt chimique en phase vapeur comportant un composé de platine organique et procédé de dépôt chimique en phase vapeur utilisant ladite matière brute pour dépôt chimique en phase vapeur
JP5919882B2 (ja) コバルト化合物の混合物、及び当該コバルト化合物の混合物を用いたコバルト含有薄膜の製造方法
JP5817727B2 (ja) マグネシウムビス（ジアルキルアミド）化合物、及び当該マグネシウム化合物を用いるマグネシウム含有薄膜の製造方法
JP3511228B2 (ja) エチルシクロペンタジエニル（１，５−シクロオクタ ジエン）イリジウムとその製造方法及びそれを用いた イリジウム含有薄膜の製造方法
JP6565448B2 (ja) 酸化アルミニウム膜の製造方法及び酸化アルミニウム膜の製造原料
WO2017030150A1 (fr) Procédé de fabrication d'un film d'oxyde d'aluminium, matériau pour la fabrication de film d'oxyde d'aluminium et composé d'aluminium
JP2017081857A (ja) ビス（シリルアミドアミノアルカン）金属化合物及び当該金属化合物を用いた金属含有膜の製造方法
JP5825169B2 (ja) コバルト含有薄膜の製造方法
JP5454141B2 (ja) 有機白金錯体及び当該白金錯体を用いた化学気相蒸着法による白金含有薄膜の製造法
WO2017150212A1 (fr) Procédé de production de film d'oxyde d'aluminium et matériau de départ de production pour film d'oxyde d'aluminium
JP2016222568A (ja) ビス（シリルアミドアミノアルカン）鉄化合物及び当該鉄化合物を用いた鉄含有膜の製造方法
JP2018027921A (ja) アミジナート配位子を有するジアルキルアルミニウム化合物の製造方法
JP2017110268A (ja) 酸化アルミニウム膜の製造原料及び酸化アルミニウム膜の製造方法
TW202033533A (zh) 金屬有機化合物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11814711

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2012527770

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20137005201

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 11814711

Country of ref document: EP

Kind code of ref document: A1