GB2309970A - Reducing viscosity of dimethylaluminium hydride - Google Patents
Reducing viscosity of dimethylaluminium hydride Download PDFInfo
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- GB2309970A GB2309970A GB9707230A GB9707230A GB2309970A GB 2309970 A GB2309970 A GB 2309970A GB 9707230 A GB9707230 A GB 9707230A GB 9707230 A GB9707230 A GB 9707230A GB 2309970 A GB2309970 A GB 2309970A
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- United Kingdom
- Prior art keywords
- viscosity
- lewis base
- dmah
- amount
- ether
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- TUTOKIOKAWTABR-UHFFFAOYSA-N dimethylalumane Chemical compound C[AlH]C TUTOKIOKAWTABR-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000002879 Lewis base Substances 0.000 claims abstract description 26
- 150000007527 lewis bases Chemical class 0.000 claims abstract description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 7
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 4
- OXQOBQJCDNLAPO-UHFFFAOYSA-N 2,3-Dimethylpyrazine Chemical compound CC1=NC=CN=C1C OXQOBQJCDNLAPO-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 4
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 claims description 2
- UUNMKKRWFDYYKW-UHFFFAOYSA-N 2,2-dimethylpentane-3,3-diamine Chemical compound CCC(N)(N)C(C)(C)C UUNMKKRWFDYYKW-UHFFFAOYSA-N 0.000 claims description 2
- BODVSESPBZOELC-UHFFFAOYSA-N 2-(2-phenylethyl)-1h-imidazole Chemical compound N=1C=CNC=1CCC1=CC=CC=C1 BODVSESPBZOELC-UHFFFAOYSA-N 0.000 claims description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 claims description 2
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 2
- TZHYFNJRLMHJCM-UHFFFAOYSA-N n-(3-phenylpropyl)aniline Chemical compound C=1C=CC=CC=1CCCNC1=CC=CC=C1 TZHYFNJRLMHJCM-UHFFFAOYSA-N 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- WWVNWQJKWKSDQM-UHFFFAOYSA-N triethylarsane Chemical compound CC[As](CC)CC WWVNWQJKWKSDQM-UHFFFAOYSA-N 0.000 claims description 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims 1
- KAHVZNKZQFSBFW-UHFFFAOYSA-N n-methyl-n-trimethylsilylmethanamine Chemical compound CN(C)[Si](C)(C)C KAHVZNKZQFSBFW-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 33
- 238000007740 vapor deposition Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000012159 carrier gas Substances 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 235000010210 aluminium Nutrition 0.000 description 4
- 238000005229 chemical vapour deposition Methods 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- -1 lithium aluminum hydride Chemical compound 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 101100220066 Arabidopsis thaliana CDA4 gene Proteins 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- ORVACBDINATSAR-UHFFFAOYSA-N dimethylaluminum Chemical compound C[Al]C ORVACBDINATSAR-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/065—Aluminium compounds with C-aluminium linkage compounds with an Al-H linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
A method of reducing the viscosity of dimethylaluminum hydride comprises adding at least one Lewis base to dimethylaluminum hydride in an amount of 0.01 to 10% by weight of the dimethylaluminum hydride.
Description
METHOD OF REDUCING VISCOSITY OF D IMETHYLALUMINUM HYDRIDE
The present invention relates to a dimethylaluminum hydride composition, a process for producing the same and a method of reducing the viscosity of dimethylaluminum hydride. More particularly, it relates to a dimethylaluminum hydride composition having a viscosity of not more than about 2000 mPas (rn?as is equivalent to 'centipoise) at normal temperature (250C), which is superior in handling properties, a process for producing the same and a method of reducing the viscosity of dimethylaluminum hydride to not more than about 2000 mPas at normal temperature under atmospheric pressure
Dimethylaluminum hydride (hereinafter abbreviated to "DMAH") is mainly used as an aluminum raH material in a chemical vapor deposition process (e.g. metal organic chemical vapor deposition, metal organic molecular beam epltaxy, etc ). In the process, the dimethylaluminum hydride is introduced into a vapor deposition device according to method (1) comprising supplying a carrier gas such as hydrogen whose flow is controlled by a mass flow controller into a DMAH solution in a storage container, bubbling the carrier gas through the solution and then introducing the bubbled carrier gas saturated with DMAH into a vapor deposition device; method (2) comprising directly heating a DMAH storage container to evaporate DMAR at a temperature below its boiling point and introducing DMAH vapor into a vapor deposition device while controlling the flow using a mass flow controller; or method (3) comprising pressurizing a DMAH storage container using a carrier gas such as hydrogen or nitrogen, transferring DMAH in the container to an evaporator in the liquid state, heating D-H in the evaporator to evaporate DSSH and supplying a carrier gas to introduce DMAH vapor into a vapor deposition device.
Bowever, DMAH has the following problems on use. That is, it is difficult to transfer DMAH from a storage container to the device to be used and to conduct bubbling at the time of the vapor deposition reaction because DESH has high viscosity, i.e., from several thousands to several ten thousands at room temperature. From the manufacturing point of view, it is difficult to transfer or deactivate
DMAH as compared with other normal organic aluminums because
DMAH has a self-ignition property and high viscosity. A method of reducing the viscosity of dimethylaluminum hybrid has thus been desired.
Under these circumstances, the present inventors have intensively studied methods of reducing the viscosity of dimethylaluminum hydride even at normal temperature under atmospheric pressure. As a result, it has been found that a remarkable effect of reducing the viscosity of Db2H is obtained when a very small amount of a Lewis base is added to DMAII. Thus, the present invention has been accomplished.
An object of the present invention is to provide a dimethylaluminum hydride composition having a low viscosity at normal temperature under atmospheric pressure, which is easily handled.
Another object of the present invention is to provide a process for producing the same.
Still another object of the present invention is to provide a method of reducing the viscosity of dimethylaluminum hydride
These objects as well as other objects and advantages of the present invention will become apparent to those skilled in the art from the following description.
In suramary, the present invention provides a dimethylaluminum hydride composition having a viscosity of not more than about 2000 mPa-s at 25'C, comprising dimethylaluminum hydride and at least one Lewis base in an amount of -01 to 10 t by weight of dimethylaluminum hydride, and a process for producing the same.
The present invention further provides a method of reducing the viscosity of dimethylaluminum hydride to not more than about 2000 mP & s at normal temperature (25 C) under atmospheric pressure, which comprises adding at least one
Lewis base to dimethylaluminum hydride in an amount of 0.01 to 10 8 by weight of dimethylaluminum hydride.
The present invention relates to a DMAH composition comprising dimethylaluminum hydride and a Lewis base in an amount of visually from 0.01 to about 10 % by weight, preferably from about 0.03 to about 1.0 % by weight, based on DMAH, wherein the viscosity of the DMAH composition at normal temperature (25 C) is not more than about 2000 mPas, normally not more than about 1000 mPa-s, and preferably from about 10 to about 500 mPas. Such a composition is extremely superior in-handling properties.
The DMAH composition may consist essentially pf dimethylaluminum hydride and at least one Lewis base.
According to a typical process for producing the DMAH composition, a Lewis base is added in the amount of usually from 0.01 t:o about 10 % by weight, preferably from about 0.03 to about 1.0 % by weight based on DMAH, followed by mixing n.he.nMAH to be used is not a specific one, and is D!SH hiving a vi CO ty of more t0an 2000 mPas at normal temperature, normally from several thousands to several ten thousands mPas, particularly from about 4000 to 20000 mPas and more particularly from about 4000 to 10000 mPas at normal temperature (25 'C), which is commercially available or obtainable by a known synthetic method, for example, by reacting dimethylaluminum chloride with alkali metal hydride or by reacting trimethylaluminum with lithium aluminum hydride ( e.g., USP 4,924,019 and J. Am. Chem. Soc. 75, 835 (1953)).
The Lwis base used in the present invention refers to a compound having at least one single pair of electrons and which can be coordinated with DtiAd, Examples of the Lewis base include organic compounds containing at least one element selected from the element groups Vb and VIb in the
Periodic Table and organic compounds containing at least one element selected from N, P, As, 0 and S. Specific examples thereof include ethers such as diethyl ether, dibutyl ether, methyl butyl ether, anisole, diphenyl ether, benzyl ether, dirnethoxyethane, diethoxyethane, tetrahydrofuran and dioxane; urines such as triethylamine, trioctylamine, dimethylprpylamine, dimethyldodecylamine, dimethylamnotrimethylsilane, dimethylallylamine, diisopropylethylamine, dimethylaniline, benzylethylaniline, tetramethylethylenediamine, tetramethyldiaminopropane and tetramethylhexamethylenediamine; heterocyclic compounds having at least one nitrogen atom in a ring structure such as pyridine, dimethylaminopyridine, collidine, pyrazine, dimethylpyrazine, pyrazole, quinoline, isoquinoline, triazine, triazole, quinaldine, imidazole and benzylmethylimidazole; sulfides such as dimethyl sulfide, diethyl sulfide and diphenyl sulfide; heterocyclic compounds having at least one sulfur atom in a ring structure such as thiophene; phosphines such as triethylphosphine and triphenylphosphine; organoarsine such as triethylarsine, etc. Among them, diethyl ether, butyl ether, tetrahydrofuran, triethylamine, dimethyldodecylamine and åimethylaniline are preferred.
The Lewis base may be normally added to DMAH at normal temperature in an amount of usually from about 0.01 to about 10 8 by weight, preferably from about 0.03 to about 1 % by weight of DMAH, followed by mixing. After the operat:ion, there can be obtained a DMAH composition having a viscosity of not more than about 2000 mPas even at normal temperature (25 "C) under atmospheric pressure, which is superior in handling properties.
The upper limit of the amount of the Lewis base may be usually decided by the permissible purity of DMAH as limited by its application.
When the Lewis base is added in an amount of from 0.01 to 1 % by weight of DMAH, a sufficient effect of reducing the viscosity of the resulting composition can usually be obtained in handling DMAH at normal temperature, i.e. a viscosity of not more than about 2000 mPas, preferably not more than about 1000 mPas, and more preferably not more than about 500 mPas.
The Lewis base to be used can suitably be selected depending on the application of the DMAH. The Lewis bases containing oxygen generally have a better effect in reducing the viscosity. When even a very small amount of oxygen impurity exerts a deleterious influence c'n the use of the
DMAH composition, other Lewis bases such as compounds containing at least one nitrogen atom ( i.e. amines and heterocyclic compounds having nitrogen atom in a ring structure ) are preferably used.
A prowess comprising adding the Lewis base to DStH, followed by mixing, is only shown as an example of a process for producing the DMAH composition according to the present invention. As a matter of course, the process of previously adding the Lewis base at the time of synthesizing DMAH may be used in the present invention if the amount of the Lewis base in the DMAH composition is sufficient for the purpose of reducing the viscosity.
The DA2H composition whose viscosity is reduced according to the present invention may be used as an aluminum raw material in the chemical vapor deposition process after introduction into a vapor deposition device according to a method comprising bubbling a carrier gas such as hydrogen gas in a solution comprising the DMAB composition to form a vapor of DMAH, or a method comprising heating a solution comprising the DMAH composition in an evaporator to evaporate DMAH and supplying a carrier gas therein.
The method for evaporating the DMAH composition, method for introducing into the vapor deposition device, method for using in the vapor deposition device and devices used for these methods may be methods or devices which have hitherto been known, and are not specifically limited.
As described above, a D1AH composition of the present invention has a viscosity of not more than about 2000 mPas at normal emperature, normally not more than about 1000 mPa-s, which is superior in handling properties. The viscosity of DMAH can be easily reduced by an extremely simple operation of adding a very small amount of a Lewis base to DM). Therefore, the industrial utility value of the DMAH composition as the aluminum raw material in the chemical vapor deposition process is quite significant.
The following Examples and Comparative Example further illustrate the present invention in detail but are not. to be construed to limit the scope thereof.
In the present invention, analysis of concentration of ether in :MAS and viscosity analysis of DMAH were conducted by the method described below.
Analysis of ether: After DMAH was diluted with dodecane, the resulting solution was hydrolyzed. Then, the content of the ether (diethyl ether and THF) in water, dodecane and gas were respectively determined by gas chromatography, and the content was converted into-the ether concentration to D!SH. As the amount of the ether calculated by the above analysis was found to be identical to the amount actually added, all of the amounts of Lewis base in ths Examples and of heptane in the Comparatlve Example ar= shown by the amounts added.
Viscosity analysis of DMAH: After DMAH as a sample was supplied t one of two containers connected to each other with a capillary, an inert gas was introduced into this container under pressure and transferred to the other container, At this point, the transfer amount and tilne were measured, and then they were substituted into the
Poiseuille's equation to determine viscosity.
Example 1
Diethyl ether was added to commercially available! DISH (17 g) (manufactured by Sumitomo Chemical Industries Co.,
Ltd., viscosity: 7700 mPas, purity of 99.999 % calculated from inorganic material analysis ) in the amount shown in
Table I and, after stirring with a magnetic stirrer, the viscosity of the resulting DMAH composition was measured at room temperature (25 C) The results are shown in Table 1.
< Table 1 >
Experiment No Amount of diethyl Viscosity of DMAH ether added composition 1 None 7700 2 0,09 300 3 0.13 180 4 0.64 45 5 4.28 19 The amount of diethyl ether added is represented bv % by eight based on DMAH.
Example 2
According to the same manner as that described in
Example 1 except for adding THF in place of diethyl ether in the amount shown in Table 2, the mixture was stirred with a magnetic stirrer, and then the viscosity of the result:ing DMAH composition was measured at room temperature (25 C).
The results are shown in Table 2.
< Table 2 >
Experiment No. Amount of TllF Viscosity of DMAH added. composition 1. None 7700 2 0.03 1200 ~ ~ ~ 0.15 135 Example 3
According to then same manner as that described in
Example 1 except for adding triethylamine in place of diethyl ether in the amount shown in Table 3, the mixture was stirred with a magnetic stirrer, and then the viscosity of the resulting DMAH composition was measured at room temperature (25 C). The results are shown in Table 3.
< Table 3 >
Experiment No. Amount of Viscosity of DMAH triethylamine added composition 1 None 7700 2 0.14 1100 3 0.71 140 Comparative Example 1 According to the same manner as that described in
Example 1 excerpt for adding heptane in place of diethyl ether in the amount shown in Table 4, the mixture was stirred with a magnetic stirrer, and then the viscosity of the resulting DMAH composition was measured at room temperature (25 C). The results are shown in Table 4.
< Table 4 >
Experiment No. Amount of heptane Viscosity of DrthH added composition I None 7700 2 2.9 5600 3 17.1 1500 4 31.4 640 Example 4
N,N-dimethylaniline was added to commercially available
DMAH (17 g) (manufactured by Sumitomo Chemical Industries
Co., Ltd., viscosity: 10000 mPa-s, purity of 99.999 % calculated from inorganic material Analysis ) in the amount shown in Table 5 and, after stirring with a magnetic stirrer, the viscosity of the resulting DtiAH composition was measured at room temperature (25 C). The results are shown in Table 5.
< Table 5 >
Experiment No. Amount of Viscosity of DMAH N,N-dimethylaniline composition 1 None 10000 2 C.10 860 3 0.25 220
Claims (11)
1. A method of reducing the viscosity of dimethylaluminum hydride, which comprises adding at least one Lewis base to dimethylaluminum hydride in an amount of 0.01 to 10% by weight of the dimethylaluminum hydride.
2. A method according to claim 1, wherein the amount of the Lewis base is from 0.01 to 1% by weight based on the dimethylaluminum hydride.
3. A method according to claim 1 or 2, wherein the amount of the Lewis base is from 0.03 to 1.0% by weight based on the dimethylaluminum hydride.
4. A method according to any one of claims 1 to 3, wherein the viscosity is not more than 2000 mPa.s at 250C.
5. A method according to claim 4, wherein the viscosity is not more than 1000 mPa.s at 250C.
6. A method according to claim 5, wherein the viscosity is not more than 500 mPa.s at 250C.
7. A method according to any one of claims 1 to 6, wherein the Lewis base is an organic compound containing at least one element selected from groups Vb and VIb in the
Periodic Table.
8. A method according to claim 7, wherein the Lewis base is an organic compound containing at least one element selected from the group consisting of N, P, As, 0 and S.
9. A method according to claim 8, wherein the Lewis base is selected from the group consisting of diethyl ester, dibutyl ether, methyl butyl ether, anisole, diphenyl ether, benzyl ether, dimethoxyethane, diethoxyethane, tetrahydrofuran, dioxane, triethylamine, trioctylamine, dimethylpropylamine, dimethyldodecylamine, dimethylaminotrimethylsilane, dimethylallylamine, diisopropylethylamine, dimethylaniline, benzylethylaniline, tetramethylethylenediamine, tetramethyldiaminopropane, tetramethylhexamethylenediamine, pyridine, dimethylaminopyridine, collidine, pyrazine, dimethylpyrazine, pyrazole, quinoline, isoquinoline, triazine, triazole, quinaldine, imidazole, benzylmethylimidazole, dimethyl sulfide, diethyl sulfide, diphenyl sulfide, thiophene, triethylphosphine, triphenylphosphine and triethylarsine.
10. A method according to claim 9, wherein the Lewis base is selected from the group consisting of diethyl ether, dibutyl ether, tetrahydrofuran, triethylamine, dimethyldodecylamine and dimethylaniline.
11. A method according to claim 1 substantially as hereinbefore described in any one of Examples 1 to 4.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10675895 | 1995-04-28 | ||
| JP8014117A JPH0912581A (en) | 1995-04-28 | 1996-01-30 | Dimethylaluminum hydride composition, its production and viscosity adjustment of dimethylaluminum hydride |
| GB9608938A GB2300189B (en) | 1995-04-28 | 1996-04-29 | Dimethylaluminum hydride composition and process for producing the same |
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| Publication Number | Publication Date |
|---|---|
| GB9707230D0 GB9707230D0 (en) | 1997-05-28 |
| GB2309970A true GB2309970A (en) | 1997-08-13 |
| GB2309970B GB2309970B (en) | 1998-01-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9707230A Expired - Fee Related GB2309970B (en) | 1995-04-28 | 1996-04-29 | Method of reducing viscosity of dimethylaluminum hydride |
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| Country | Link |
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| GB (1) | GB2309970B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2300189A (en) * | 1995-04-28 | 1996-10-30 | Sumitomo Chemical Co | Dimethylaluminum hydride composition, process for producing the same and method of reducing viscosity of dimethylaluminum hydride |
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1996
- 1996-04-29 GB GB9707230A patent/GB2309970B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2300189A (en) * | 1995-04-28 | 1996-10-30 | Sumitomo Chemical Co | Dimethylaluminum hydride composition, process for producing the same and method of reducing viscosity of dimethylaluminum hydride |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2309970B (en) | 1998-01-07 |
| GB9707230D0 (en) | 1997-05-28 |
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| Date | Code | Title | Description |
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| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20000429 |