GB2123422A - Production of compounds for use in semiconductor preparation - Google Patents
Production of compounds for use in semiconductor preparation Download PDFInfo
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- GB2123422A GB2123422A GB08316317A GB8316317A GB2123422A GB 2123422 A GB2123422 A GB 2123422A GB 08316317 A GB08316317 A GB 08316317A GB 8316317 A GB8316317 A GB 8316317A GB 2123422 A GB2123422 A GB 2123422A
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- Prior art keywords
- ether
- compound
- formula
- inert diluent
- compounds
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 8
- 239000004065 semiconductor Substances 0.000 title description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 98
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000003701 inert diluent Substances 0.000 claims abstract description 18
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003085 diluting agent Substances 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical group [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims abstract description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000004411 aluminium Substances 0.000 claims abstract description 3
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052785 arsenic Chemical group 0.000 claims abstract description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 229910052733 gallium Inorganic materials 0.000 claims abstract description 3
- 238000011065 in-situ storage Methods 0.000 claims abstract description 3
- 229910052738 indium Chemical group 0.000 claims abstract description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical group [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 3
- 239000011574 phosphorus Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- IBEFSUTVZWZJEL-UHFFFAOYSA-N trimethylindium Chemical compound C[In](C)C IBEFSUTVZWZJEL-UHFFFAOYSA-N 0.000 claims description 4
- WWVNWQJKWKSDQM-UHFFFAOYSA-N triethylarsane Chemical compound CC[As](CC)CC WWVNWQJKWKSDQM-UHFFFAOYSA-N 0.000 claims description 2
- XCZXGTMEAKBVPV-UHFFFAOYSA-N trimethylgallium Chemical compound C[Ga](C)C XCZXGTMEAKBVPV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 6
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 5
- 241000349731 Afzelia bipindensis Species 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 3
- HTDIUWINAKAPER-UHFFFAOYSA-N trimethylarsine Chemical compound C[As](C)C HTDIUWINAKAPER-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 101100242814 Caenorhabditis elegans parg-1 gene Proteins 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal salt Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001983 dialkylethers Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5045—Complexes or chelates of phosphines with metallic compounds or metals
-
- 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
-
- 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
- C07F5/062—Al linked exclusively to C
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Compounds of the formula I, <IMAGE> wherein M is aluminium, gallium or indium; X is nitrogen, phosphorus or arsenic; and each of R1, R2, R3, R4, R5 and R6, any two of which may be the same or different, is alkyl or aryl are produced by preparing a compound of the formula II, <IMAGE> wherein M, R1, R2 and R3 are as defined above, in situ in an ether; removing the ether in the presence of an inert diluent and a compound of the formula III, <IMAGE> wherein X, R4, R5 and R6 are as defined above; and removing the diluent. Thus InMe3.PEt3 can be prepared with the use of diethyl ether and of benzene as the inert diluent.
Description
SPECIFICATION
Production of compounds for use in semi-conductor preparation
This invention relates to a method for the production of compounds for use in semi-conductor preparation.
In preparing semi-conductor materials, one may conveniently use compounds of the formula
wherein M is aluminium, gallium or indium; X is nitrogen, phosphorus or arsenic; and each of R1, R2, R3, R4, R5 and R6, any two of which may be the same or different, is alkyl or aryl. These compounds must be prepared in a form which is sufficiently pure to allow the consequent preparation of semi-conductors having an impurity level of less than 1 ppb. One method for using formula I compounds is the MOCVD method disclosed in European Patent Publication No.
52979. Such compounds are often referred to as "adducts".
Coates et al., J. C. S. (1956) 3351 discloses the reaction of pure trimethylindium with a
Lewis base, i.e. either diethyl ether or trimethylphosphine, to form the corresponding adduct.
The etherate lnMe3.Et2O is also disclosed by Runge et al., Z. Anorg. Allgem. Chem., 267 (1951) 39, where it is prepared from indium trichloride, methylmagnesium chloride and diethyl ether; by Todt et al., Z. Anorg. Allgem. Chem., 321 (1963) 120, where it is prepared from In
Mg alloy, methyl chloride and diethyl ether; and by Clark et al., J. Organometal. Chem., 8 (1967) 427, where it is prepared from indium trichloride methyllithium and diethyl ether, followed by distillation in vacuo.
Beachley et al., J. C. S. (1965) 3241 disclose the separation of ether from lnMe3.Et2O in benzene. The method of preparation of the etherate is quoted as the above-described method of
Todt et al.
Coates, J. C. S. (1951) 2006 discloses various competitive experiments, including the following:
Me3Ga.AsMe3 + PMe3oMe3Ga.PMe3 + Me3As
Me3Ga.PMe3 + NMe3oMe3Ga.NMe3 + Me3P Me3Ga.OMe2 + AsMe3 yMe3Ga.AsMe3 + Me2O Gribov et al, Dokl. Akad. Nauk. SSSR, 204, pages 350-351 (1972) disclose the preparation of Me3GaNEt3, Me3GaAsEt3, Me3GaSbEt3, Et3GaNEt3, and Et3GaAsEt3 by the room-temperature reaction of the trialkylgallium diethyl etherate and the group V trialkyl compound in stoichiometric proportions.
According to the present invention, a method for producing a compound of formula I comprises preparing a compound of the formula II,
wherein M, R,, R2 and R3 are as defined above, in situ in an ether; removing the ether in the presence of an inert diluent and a compound of the formula Ill,
wherein X, R4, R5 and R6 are as defined above; and removing the diluent.
The method of the invention can be used to produce a compound of formula I, from standard starting materials, having a purity sufficiently good for the growth of satisfactory semi-conductor materials. The method can be used safely on a commercial scale, apparently as a result of using a stabilised form of the formula II compound, and displacing the stabilising ether in a diluent, such that the ultimately unwanted components can be safely removed.
The compound of formula Il is usually a metal trialkyl compound such as trimethylgallium or trimethylindium. This compound is prepared, in a manner known per se, in an ether. The ether may be, for example, diphenyl ether but is preferably a dialkyl ether, e.g. of the formula R'OR" in which R' and R" are the same or different C16 alkyl groups. The ether is preferably dimethyl ether or, most preferably, diethyl ether.
By way of example, a salt of the element M (e.g. Inc3) is reacted with an alkali metal alkyl such as methyllithium, to give the formula il compound (e.g. trimethylindium) and an alkali metal salt such as lithium chloride. The starting salt may be used in ether, in which alkali metal salts are insoluble and therefore precipitate out. The desired etherate of the formula Il compound remains, suitably in solution in excess ether.
The inert diluent and the formula Ill compound are added, separately or simultaneously, to the etherate, before or after (but preferably before) any solids such as lithium chloride are separated off. Any solids are suitably removed by filtration, e.g. after the addition of inert diluent and formula Ill compound. Alternatively, although less preferably, the etherate and excess ether may be removed from any unwanted product of the formula ll compound preparation by distillation.
The formula ill compound will usually be a trialkyl compound such as triethyl phosphine or triethyl arsine. The inert diluent may be any suitable aromatic solvent, with benzene being preferred. The diluent should be inert to the extent that it does not form an adduct with the formula ll compound in competition with the ether.
Although it is usually the case for ethers and inert aromatic solvents, it is an advantage that these components should be miscible. Diethyl ether and benzene are completely miscible. It is also desirable that the formula Ill compound is soluble in the inert diluent; if it is insoluble, a heterogeneous reaction can be carried out. The etherate should be soluble in the inert diluent.
In the next step of the reaction, the ether is removed, to leave the formula I compound in the inert diluent. The ether may be removed by, for example, distillation. Although this reaction may not be favoured thermodynamically, it can be made to go by virtue of the ether's volatility. In order that ether should be distilled off, rather than the inert diluent or the formula Ill compound, the ether should have the highest volatility.
It is preferred that the inert diluent should have a boiling point at least 15C degrees higher than the ether (at 760 mm Hg). Such a difference allows the ether to be removed simply. A lower difference, e.g. of 1-5 C degrees does not prevent the desired reaction, but more complex removal apparatus, e.g. a spinning band column, is then necessary. By way of reference, diethyl ether and benzene have boiling points of 34.5 and 80"C, respectively, at 760 mm Hg.
In the final step of the method of the invention, the inert diluent is removed. It is helpful if, for this purpose, the formula I compound is insoluble in the diluent, so that the need for fractionation is minimised. It is preferred if the inert diluent can be removed by distillation, in which case it should have a higher volatility than any of the formulae I, il and Ill compounds.
Again, the difference is preferably at least 1 5 C degrees in boiling point at 760 mm Hg (the boiling point of triethyl phosphine is 129"C).
Examples of compounds which can be prepared by the method of the invention are Me3ln.PEt3; Me31n. AsEt3; Et31n.NEt3 and Me3Ga.PEt3. The existence of such a product in the reaction mixture can be determined by its distinct vapour pressure.
If desired, the product of formula I may be purified. For the preparation of the purest products, individual purification steps may be carried out, e.g. the passage of triethylphosphine over calcium hydride, but, for example, commercial indium chloride, diethyl ether and benzene are usually sufficiently pure. The product may be a solid which can be sublimed under vacuum.
The following Examples illustrate the method of the invention.
Example 1 InMe3.PEt3
InCI3 (25.1 g, 113.5 mmol) was stirred in c.50 ml diethyl ether overnight. CH3Li (164.5 ml of 2.07 M solution, 340.5 mmol) was added to the solution dropwise at O"C over 30 minutes.
The product was vacuum distilled at up to 100"C for 2 hours. A clear, colourless solution was collected. Benzene (100 ml) and P(C2H5)3 (16.7 ml, 13.49, 113.5 mmol) were added at once.
There was no visible change. Distillation was conducted under nitrogen, using a Perkin Triangle, to obtain a cloudy liquid which was transferred to a 100 ml flask. The solvent was pumped off at room temperature over c. 3 hours. A large mass of white powder, smelling strongly of phosphine, was left.
The product was sublimed over an oil bath, irradiated with a 250 W infra-red lamp and backed with an aluminium foil reflector. Local heat was applied with a hot air blower. The receiver was then cooled in dry ice. No condensation was observed on those parts warmed by the infra-red lamp, while melting was observed from 45"C. 1 8.4 g (58% of theory) of long needle-like, non-sticky, white crystals were obtained. Proton nmr integration gave P(C2H5)3:
In(CH3)3= 1.67 (theory), 1.74 (experimental). lR:2255 (w,sh), 1409 (m,sh), 1260 (w,sh), 1250 (m,sh), 1235 (w,sh), 1138 (s,sh), 1040 (vs,sh), 762 (s,sh), 758 (s,sh), 680 (s,br), 482 (vs,sh) (units:cm-', medium:Nujol mull).
Example 2 InMe3.PEt3 InCI3 (30.6 g, 138.4 mmol) was suspended in 75-110 ml diethyl ether. CH3Li (215.1 ml of 1.93 M solution, 415.1 mmol) was added dropwise, over an ice bath, over 20 minutes. The reaction mixture was then stirred for 30 minutes at room temperature and distilled trap-to-trap.
Benzene (100 ml) and PEt3 (20.4 ml) were added. The mixture was allowed to stand overnight.
Ether was then removed by fractionation. Subsequently, benzene was pumped off with excess
PEt3 at room temperature, over 2 hours. 38.4 g (50% of theory) of product were obtained.
Example 3 InMe3.PEt3
MeLi (70.5 ml of 1.93 M solution, 136 mmol) was added dropwise to InCI3 (10 g, 45.22 mmol) in a pot maintained at 14"C by a running water bath. The reaction mixture was stirred at room temperature for 1 hour. Benzene (100 ml) was added and the product filtered through a
No. 4 sinter to obtain a colourless liquid smelling strongly of InMe3.PEt3 (c. 7 ml) was added, and a cloudy white precipitate was formed immediately. The product was stored in the dark at - 25"C.
Following filtration through a No. 4 sinter, the white solid was isolated, to give a clear, colourless solution. This was stirred overnight, in the dark, at - 25"C.
The liquid was subjected to a careful fractional distillation. At 80"C, take-off was stopped and the temperature fell to 79"C over 30 minutes. The temperature rose to 81 C when fraction collected, and did not change appreciably. The solution was cloudy in part, but not opaque. The remaining solvent was pumped off.
The product was partially soluble in pentane. The yield was 7.0 g (56% of theory). A white crystalline solid remained after sublimation onto a room temperature cold finger at 100-110"C/10-3 torr; yield 2.2 g.
Example 4 InMe3.PEt3
InCI3 (52.3 g, 236.5 mmol) was covered with diethyl ether (c. 1 50 ml) and stirred at room temperature for 3 days to effect complete dissolution (other than a very small amount of white precipitate). The solution was cooled to 16"C in running water and MeLi (368 ml of 1.93 M solution, 709 mmol) was added. After 20 minutes, half the MeLi had been added, and a white precipitate appeared. Addition was completed after a further 45 minutes. The reaction mixture was stirred for 1 hour, whereupon PEt3 (28 g, 237 mmol, 35 ml) and benzene (200 ml) were added. The mixture was filtered through a No. 4 glass sinter. Filtration was easier after allowing the mixture to stand overnight. The filtered liquid was fractionated using a Perkin triangle; yield 27.6 g (42% of theory).
Example 5 Me3Ga.PEt3
GaCI3 (20.5 g, 116 mmol) in diethyl ether (c. 250 ml) was cooled to 18"C in running water.
MeLi (181.0 ml of 1.93 M solution, 349 mmol) was added over 2Q hours. A very coarse precipitate was obtained. The reaction mixture was allowed to stir overnight, whereupon it could be filtered, very smoothly, to give a clear, colourless liquid. Benzene and PEt3 (17.1 ml, 13.7 g) were added; an exothermic reaction was observed. A small amount of white precipitate formed and was filtered off. Fractionation was conducted as in earlier Examples. After sublimation, 27.07 g (43.2% of theory) of the product was obtained.
Claims (10)
1. A method for producing a compound of the formula I,
wherein M is aluminium, gallium or indium; X is nitrogen, phosphorus or arsenic; and each of R1, R2, R3, R4, R5 and R6, any two of which may be the same or different, is alkyl or aryl, which process comprises preparing a compound of the formula II,
wherein M, R1, R2 and R3 are as defined above, in situ in an ether; removing the ether in the presence of an inert diluent and a compound of the formula Ill,
wherein X, R4, R5 and R6 are as defined above; and removing the diluent.
2. A method according to claim 1, in which the formula II compound is trimethylindium or trimethylgallium.
3. A method according to claim 1 or claim 2, in which the formula Ill compound is triethylphosphine or triethylarsine.
4. A method according to any preceding claim, in which the removal of the ether is effected by distillation.
5. A method according to claim 4, in which the inert diluent has a boiling point at least 1 5 C degrees higher than the ether (at 760 mm Hg).
6. A method according to any preceding claim, in which removal of the inert diluent is effected by distillation.
7. A method according to claim 6 in which the formula Ill compound has a boiling point at least 1 5 C degrees higher than the inert diluent (at 760 mm Hg).
8. A method according to any preceding claim, in which the ether is diethyl ether.
9. A method according to any preceding claim, in which the inert diluent is benzene.
10. A method for the production of an adduct substantially as described in any one of
Examples 1 to 5 herein.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08316317A GB2123422B (en) | 1982-07-19 | 1983-06-15 | Production of compounds for use in semiconductor preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8220857 | 1982-07-19 | ||
| GB08316317A GB2123422B (en) | 1982-07-19 | 1983-06-15 | Production of compounds for use in semiconductor preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8316317D0 GB8316317D0 (en) | 1983-07-20 |
| GB2123422A true GB2123422A (en) | 1984-02-01 |
| GB2123422B GB2123422B (en) | 1985-11-06 |
Family
ID=26283381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08316317A Expired GB2123422B (en) | 1982-07-19 | 1983-06-15 | Production of compounds for use in semiconductor preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2123422B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985004405A1 (en) * | 1984-03-26 | 1985-10-10 | The Secretary Of State For Defence In Her Britanni | The preparation of metal alkyls |
| WO1989001479A1 (en) * | 1987-08-08 | 1989-02-23 | MERCK Patent Gesellschaft mit beschränkter Haftung | Cyclic or bicyclic aluminium, gallium or indium organic compounds and their use for vapour deposition of metals on substrates |
| US4885376A (en) * | 1987-10-13 | 1989-12-05 | Iowa State University Research Foundation, Inc. | New types of organometallic reagents and catalysts for asymmetric synthesis |
| EP0399190A1 (en) * | 1989-04-21 | 1990-11-28 | MERCK PATENT GmbH | Organometallic compounds of aluminium, gallium and indium for the manufacture of semiconductors and their use |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB923653A (en) * | 1959-07-17 | 1963-04-18 | Ziegler Karl | Process for separating triethyl aluminium from other ethyl metal compounds, and a new aluminium complex compound produced by the process |
| GB1119746A (en) * | 1966-04-11 | 1968-07-10 | Chisso Corp | Method for polymerizing vinyl compounds |
-
1983
- 1983-06-15 GB GB08316317A patent/GB2123422B/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB923653A (en) * | 1959-07-17 | 1963-04-18 | Ziegler Karl | Process for separating triethyl aluminium from other ethyl metal compounds, and a new aluminium complex compound produced by the process |
| GB1119746A (en) * | 1966-04-11 | 1968-07-10 | Chisso Corp | Method for polymerizing vinyl compounds |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985004405A1 (en) * | 1984-03-26 | 1985-10-10 | The Secretary Of State For Defence In Her Britanni | The preparation of metal alkyls |
| US4720561A (en) * | 1984-03-26 | 1988-01-19 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Preparation of metal alkyls |
| USRE33292E (en) * | 1984-03-26 | 1990-08-07 | The Secretary Of State For Defence In Her Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Preparation of metal alkyls |
| WO1989001479A1 (en) * | 1987-08-08 | 1989-02-23 | MERCK Patent Gesellschaft mit beschränkter Haftung | Cyclic or bicyclic aluminium, gallium or indium organic compounds and their use for vapour deposition of metals on substrates |
| US5015747A (en) * | 1987-08-08 | 1991-05-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Organometallic compounds |
| US4885376A (en) * | 1987-10-13 | 1989-12-05 | Iowa State University Research Foundation, Inc. | New types of organometallic reagents and catalysts for asymmetric synthesis |
| EP0399190A1 (en) * | 1989-04-21 | 1990-11-28 | MERCK PATENT GmbH | Organometallic compounds of aluminium, gallium and indium for the manufacture of semiconductors and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8316317D0 (en) | 1983-07-20 |
| GB2123422B (en) | 1985-11-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950615 |