GB2295392A - Organometallic complexes of aluminium, gallium and indium - Google Patents
Organometallic complexes of aluminium, gallium and indium Download PDFInfo
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- GB2295392A GB2295392A GB9523981A GB9523981A GB2295392A GB 2295392 A GB2295392 A GB 2295392A GB 9523981 A GB9523981 A GB 9523981A GB 9523981 A GB9523981 A GB 9523981A GB 2295392 A GB2295392 A GB 2295392A
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- gallium
- indium
- aluminium
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229910052733 gallium Inorganic materials 0.000 title claims abstract description 21
- 229910052782 aluminium Inorganic materials 0.000 title claims abstract description 19
- 239000004411 aluminium Substances 0.000 title claims abstract description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 229910052738 indium Inorganic materials 0.000 title claims abstract description 18
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 125000002524 organometallic group Chemical group 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- PMYWPCUIMGLRHO-UHFFFAOYSA-N n,n'-diphenylbenzenecarboximidamide Chemical compound C=1C=CC=CC=1NC(C=1C=CC=CC=1)=NC1=CC=CC=C1 PMYWPCUIMGLRHO-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002471 indium Chemical class 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- FEDWSEVYKWTKEZ-UHFFFAOYSA-N n,n'-bis(4-chlorophenyl)ethanimidamide Chemical compound C=1C=C(Cl)C=CC=1N=C(C)NC1=CC=C(Cl)C=C1 FEDWSEVYKWTKEZ-UHFFFAOYSA-N 0.000 claims description 2
- RDBJQMPXVALQIE-UHFFFAOYSA-N n,n'-bis(4-fluorophenyl)ethanimidamide Chemical compound C=1C=C(F)C=CC=1N=C(C)NC1=CC=C(F)C=C1 RDBJQMPXVALQIE-UHFFFAOYSA-N 0.000 claims description 2
- RFWAAHAPVPVWCT-UHFFFAOYSA-N n,n'-dicyclohexylethanimidamide Chemical compound C1CCCCC1N=C(C)NC1CCCCC1 RFWAAHAPVPVWCT-UHFFFAOYSA-N 0.000 claims description 2
- CLWIJUQLAFJNOF-UHFFFAOYSA-N n,n'-diphenylethanimidamide Chemical compound C=1C=CC=CC=1N=C(C)NC1=CC=CC=C1 CLWIJUQLAFJNOF-UHFFFAOYSA-N 0.000 claims description 2
- ZQUVDXMUKIVNOW-UHFFFAOYSA-N n,n'-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1NC=NC1=CC=CC=C1 ZQUVDXMUKIVNOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000320 amidine group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000001947 vapour-phase growth Methods 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 abstract description 9
- 239000003446 ligand Substances 0.000 abstract description 6
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000005229 chemical vapour deposition Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OTRPZROOJRIMKW-UHFFFAOYSA-N triethylindigane Chemical compound CC[In](CC)CC OTRPZROOJRIMKW-UHFFFAOYSA-N 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- XCZXGTMEAKBVPV-UHFFFAOYSA-N trimethylgallium Chemical compound C[Ga](C)C XCZXGTMEAKBVPV-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 229910000980 Aluminium gallium arsenide Inorganic materials 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- GPXJNWSHGFTCBW-UHFFFAOYSA-N Indium phosphide Chemical compound [In]#P GPXJNWSHGFTCBW-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- NWAIGJYBQQYSPW-UHFFFAOYSA-N azanylidyneindigane Chemical compound [In]#N NWAIGJYBQQYSPW-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- RPQDHPTXJYYUPQ-UHFFFAOYSA-N indium arsenide Chemical compound [In]#[As] RPQDHPTXJYYUPQ-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PTXGUWDEUKICHG-UHFFFAOYSA-N n,n-diphenylbenzenecarboximidamide Chemical compound C=1C=CC=CC=1C(=N)N(C=1C=CC=CC=1)C1=CC=CC=C1 PTXGUWDEUKICHG-UHFFFAOYSA-N 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 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
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- 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
- C07F5/069—Aluminium compounds without C-aluminium linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel organometallic complexes of aluminium, gallium and indium are disclosed, having improved stability and volatility for use in CVD processes. These are donor ligand complexes of the formula ML 3 where M is the metal, and L is a ligand containing an amidine (R'N---C(R')---NR') group, where R is H, alkyl etc.
Description
ORGSNOMETALLIC COMPLEXES OF ALUMINLUM GALLIUM AND INDIUM
This invention relates to volatile organometallic complexes of aluminium, gallium and indium.
Volatile organometallic compounds of aluminium, gallium and indium, e.g. the aluminium, gallium and indium alkyls, especially trimethyl gallium and triethyl indium, are of considerable interest as volatile sources of aluminium, gallium and indium metal in CVD (chemical vapour deposition) processes. Of particular interest are CVD processes employing a volatile source of aluminium, gallium or indium in the manufacture, by chemical vapour deposition on the surface of a suitable substrate, of compound semi-conductor materials such as gallium arsenide (GaAs), indium arsenide (InAs), indium phosphide (InP), indium aluminium gallium arsenide (InA1GaAs) or wide bandgap material systems such as aluminium, gallium or indium nitride.
Metal alkyls, such as trimethylaluminium, trimethylgallium and triethylindium, are, however, unstable at elevated temperature, pyrophoric and extremely sensitive to air, and are explosively hydrolytic in contact with moisture. Such materials can, therefore, be manufactured and used only under very stringent conditions.
In accordance with the present invention we have discovered that amidine complexes of aluminium, gallium and indium possess good stability at room temperature, are substantially non-pyrophoric, and show excellent thermal stability in the vapour phase. They are, therefore, of high utility as a volatile source of aluminium, gallium and indium in CVD processes of all kinds.
In accordance with the present invention, therefore, there are provided novel organometallic complexes of the formula I where M is aluminium, gallium or indium; and L is an organic ligand containing a substituted or unsubstituted amidino [R'N---C(R')---NR'] group.
The advantages of the complexes of the present invention are that they are more stable to air and moisture. Moreover, they reduce the levels of residual, unwanted alkyl groups during and after CVD processes.
The reduced alkyl content of the complex of the present invention also reduces significantly the possibility of carbon inclusion in the deposited product.
Furthermore, the complex of the present invention has a distinct advantage over the acetylacetonato analogues which are typically used in MOCVD in that the highly preferred complexes of the present invention contain no oxygen, the presence of which is detrimental to film formation. In this regard, AcAc gives Gaze,.
Preferred amidine ligands are amidines of the formula II:
R'N(H)C(R') =NR' II where R' is H, C,-C8 alkyl or haloalkyl, C3-C8 cycloalkyl, optionally including an
NH- group in the ring, C3-C8 cycloalkenyl, phenyl or substituted phenyl containing from 1-3 (C,-C8)alkyl or halo-substituents, trimethylsilyl or halogen, the R' groups being the same or different.
Typical amidine ligands within that formula are N,N'-diphenylbenzamidine, N,N'di(p-chlorophenyl)acetamidine, N, N' -diphenylformamidine, N,N'-di(p-fluorophenyl)acetamidine, benzamidine, acetamidine, and N ,N ' -dicyclohexylacetamidine.
Other suitable amidine ligands will be apparent to those skilled in the art, as will be methods for the preparation of such amidines.
The amidine complexes of this invention are prepared by reacting a suitable amount of the trialkylaluminium, trialkylgallium or trialkylindium compounds, e.g.
trimethylaluminium, trimethylgallium or triethylindium with the ligand under anhydrous conditions in vacuo or under an inert atmosphere, preferably, but not necessarily in the presence of an anhydrous hydrocarbon solvent such as toluene or n-hexane. That reaction may be represented as follows: vacuolinert gas
The alkane (RH) evolved during the course of the reaction is removed preferably continuously, following which the product complex can be recovered by removal of the slight excess of aluminium, gallium or indium trialkyl, amidine, and the solvent, if present, preferably by distillation in vacuo.
Whilst the alkyl substituents of the aluminium, gallium or indium triaikyl reactant will usually be the same, trialkyls containing different alkyl groups may be used.
Aluminium, gallium and indium complexes in accordance with this invention and the preparation thereof will now be described by way of examples, in which reference is made to the following Figures:
Figure 1 which shows the x-ray crystal diffraction results for In(PhNCPhNPh)3; and
Figure 2 which shows the thermogravimetric analysis curves of the various complexes according to the invention.
In all the Examples, the reactions were carried out on a vacuum line.
Synthesis of ([A1(PhNCPhNPh),) N,N' -Diphenylbenzamidine (1 .70g, 6.25mmol) was suspended in dry degassed hexane (40 mls), cooled to -78 C and a solution of AlMe3, in hexanes (1.1 cm3, 2 M) was added via syringe. The stirred solution was left to warm to room temperature and and the resulting white suspension was heated under reflux for 12 hours, giving a flocculent pale yellow suspension. The solvent was removed under vacuum to give a pale green/yellow solid which was dissolved in a minimum quantity of chloroform and recrystallised by cooling to -35 C, producing a slightly air sensitive pale green powder.
Yield: 62% Found: C, 79.97; H, 5.59; N. 9.55% C57H45N6Al requires C, 80.86; H, 5.55; N, 10.30% 'H NMR (CDCl3) 7.20 (ArH, 3H, t, 7Hz), 7.09 (ArH, 6H, t, 7Hz), 7.00 (ArH, 12H, t, SHz), 6.86 (ArH, 12H, t, 7Hz), 6.64(ArH, 12H, d, 7Hz).
HRMS(EI): calcd for C57H45N6Al (M)+ m/z 840.342112, found m/z 840.352 + 0.0016 MS (EI) m/z 840 (M+, 6%), 56([M-PhNCPhNPh]+,23 %), 272([LH]+, 10%), 180([M-(PhNCPhNPh)2AlNPH)J1, 100%.
Synthesis of {Ga(NPhCPhNPh)3}
N,N'Diphenylbenzamidine (0.95g, 3.5 mmol) and monomethylgalliumbis(N,N'diphenylbenzamidine) (2.19g, 3.Smmol) were dissolved in a sealed tube and heated to 200 C for 30 mins, over which time methane (1 mole equivalent) was evolved.
The pale yellow solid was dissolved in chloroform (15cm3), and the solution cooled to -35 C, producing slightly air sensitive pale yellow crystals. These were isolated by removing the solvent by filtration and washed with hexane (2 x 10cm3), and dried in vacuum.
Yield 2.0g (65%) Found: C, 77.10 H, 5.25, N,9.40 C5,H45N6 Ga requires C, 77.47, H,5.13, N, 9.51.
'H NMR (CDCl3) 6.68 (d, 12H, 0-ArH-N), 6.87 (t, 6H, p-ArH-N), 6.94 (d, 6H, o ArH-C), 7.03 (t, 12H, m-ArH-N), 7.13 (t, 6H, m-ArH-C), 7.21 (t, 3H, p-ArH-C).
13C NMR (CDCl3) 166.70 (N-C-N), 144.60 (Ar-N), 130.97 (Ar-C), 129.50 (0-Ar-C), 129.23 (p-Ar-C), 128.27 (m-Ar-C), 127.83 (m-Ar-N), 124-71 (o-Ar-N), 121.78 (p
Ar-N).
M.S.(EI) : 882 (M, 7.0), 611 ([M-PhNCPhNPh]+, 26.4), 77(Phl, 100%).
Synthesis of [Ga(PhNCMeNPh)3J This complex was prepared by the same procedure to that used for gallium-tris(N,N1- diphenylbenzamidinato). The product is a colourless solid.
Yield: 1.1 lug (65 %).
C42H39N6Ga requires; C, 72.32; H, 5.64; N, 12.5%.
Found: C, 72.02; H, 5.50; N, 11.80% 'H NMR (CDCl3); 6/ppml.95 (s, 9H, CH3), 6.63 (d, 12H, o-ArH-N), 6.85 (t, 6H, p-ArH-N), 7.00 (t, 12H, m-ArH-N).
Synthesis of [In(PhNCPhNPh)3] N,N1-diphenylbenzamidine (0.55g, 2.02mmol) was reacted with ethylindium-bis
N,N'-diphenylbenzamidine) (1.39g, 2.02mmol) as a melt at 1800C, and 1 mole equivalent of ethane was evolved over 0.5 hour. Recrystallisation of the solid from chloroform gave pale a yellow crystals, which isolated by filtration and washed with hexane (2 x 10cm3).
Yield: 1.24g (66%).
C42H39N6 In requires C, 73.71; H, 4.88; N,9.05%.
Found: C, 74.44; H, 4.81; N, 8.83%.
'H NMR (CDCl3): b/ppm 6.56 (d, 12H, o-ArH-N), 6.80 (t, 6H, p-ArH-N), 6.94 (t, 12H, m-ArH-N),m 7.01-7.05 (d, 6H, p-ArH-C), 7.11-7.26 (m, 9H, o-ArH-C, m
ArH-C).
Crystals of this compound suitable for x-ray diffraction were grown and characterisation by x-ray crystallography establishes the structure of the complex to be monomeric and to contain three bidentate amidinato groups, as shown in Figure 1 of the accompanying drawings.
Synthesis of [A1(PhNCMeNPh)J This complex was prepared using the same procedure as used for aluminium-tris(N,Ndiphnylbenzamidinato). A solution of Al2Me6 in hexanes (0.79cm3, 0.79mmol) was added to a suspension of N,N'-diphenylacetamidine (1 .0g, 4.76mmol) in hexane. The product is a colourless crystalline solid.
Yield: 0.82g (79%).
C42H39N6 Al requires C, 77.04; H, 6.00; N, 12.83%.
Found: C, 76.56; H, 6.09; N, 12.62%.
'H NMR (CDCl3); 6/pom 2.00 (s, 9H, CH3), 6.73 (d, 12H, o-ArH-N), 6.99 (t, 6H, p-ArH-N), 7. 18 (t, 12H, m-ArH-N).
Synthesis of {In(PhNCMeNPh)3}
N, N l-Diphenylacetamidine (0.53g, 2.52mmol) was reacted with ethylindum-bis(N ,N diphenylacetamidinato) (1.42g, 2.25mmol) in a sealed tube at 1800C and the product washed with hexane (2 x 10cm3). The product is a colourless solid.
Yield: 1.57g (84%).
C42H39N6In requires; C, 67.93; H, 5.29; N, 11.32%.
Found: C, 68.29; H. 4.77; N, 11.40%.
'H NMR (CDCl3); 6/pom. 1.94 (s, 9H, CH3), 6.63 (d, 12H, o-ArH-N), 6.85 (t, 6H, p-ArH-N). 7.02 (t, 12H, m-ArH-N).
The (TGA) thermogravimetric analysis curves of various complexes according to the present invention are shown in Figure 2 and show the complexes to be thermally stable to at least 200"C. (e.g. curve A) allowing ease of handling at ambient and moderately elevated temperatures. The following key applies:
A: Al(N,N'diphenylacetamidato)3 B: In(N, N ldiphenylbenzamidato)3 Thus the complexes may be readily volatalised intact, and have a useful thermal stability range; both of which properties make them useful metal precursors in metal
CVD operations. Further, observation of parent ions in the mass-spectra of these complexes may be thought indicative of the thermal-stability-volatility of such complexes under vacuo and thermal load.
Other modifications to the complexes of the present invention will be apparent to those skilled in the art.
Claims (5)
1. Organometallic aluminium, gallium and indium complexes of the formula I: ML3 wherein
M is aluminium, gallium or indium; and
L is an amidino group of the formula II R'N---C(R') --NR' II wherein
R' is H, C,-C8 alkyl or haloalkyl, C3-C8 cycloalkyl optionally including an NH- group in the ring, C3-C8 cycloalkyl, phenyl, substituted phenyl containing from 1-3 (C,-C5) alkyl or halo-substituents, trimethylsilyl or halogen, the R' groups being the same or different.
2. Organometallic aluminium, gallium and indium complexes according to claim 1 wherein the amidine group is derived from any one of the following: acetamidine, benzamidine, N, N' -diphenylbenzamidine, N,N' -di(p-chlorophenyl)-acetamidine, N, N ' -diphenylformamidine ,N, N' -diphenylacetamidine,N ,N '-di(p-tolyl)benzamidine, N, N '-di(p-fluorophenyl)acetamidine, and N, N' -dicyclohexylacetamidine.
3. A method for the chemical vapour phase deposition of aluminium, gallium or indium on a substrate which comprises contacting the substrate with a volatile organometallic gallium or indium in the vapour phase, wherein there is used an organometallic aluminium, gallium or indium complex according to claim 1 or claim 2.
4. A compound substantially as described herein.
5. A
substantially as described herein.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9423614A GB9423614D0 (en) | 1994-11-23 | 1994-11-23 | Organometallic complexes of aluminium, gallium and indium |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9523981D0 GB9523981D0 (en) | 1996-01-24 |
| GB2295392A true GB2295392A (en) | 1996-05-29 |
| GB2295392B GB2295392B (en) | 1998-03-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9423614A Pending GB9423614D0 (en) | 1994-11-23 | 1994-11-23 | Organometallic complexes of aluminium, gallium and indium |
| GB9523981A Expired - Fee Related GB2295392B (en) | 1994-11-23 | 1995-11-23 | Organometallic complexes of aluminium,gallium and indium |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9423614A Pending GB9423614D0 (en) | 1994-11-23 | 1994-11-23 | Organometallic complexes of aluminium, gallium and indium |
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| Country | Link |
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| GB (2) | GB9423614D0 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004046417A2 (en) * | 2002-11-15 | 2004-06-03 | President And Fellows Of Harvard College | Atomic layer deposition using metal amidinates |
| US9029189B2 (en) | 2003-11-14 | 2015-05-12 | President And Fellows Of Harvard College | Bicyclic guanidines, metal complexes thereof and their use in vapor deposition |
| TWI633061B (en) * | 2015-09-28 | 2018-08-21 | 氣相成長股份有限公司 | Magnesium-based structural material, method for forming magnesium-based structural material, and novel compound |
-
1994
- 1994-11-23 GB GB9423614A patent/GB9423614D0/en active Pending
-
1995
- 1995-11-23 GB GB9523981A patent/GB2295392B/en not_active Expired - Fee Related
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004046417A2 (en) * | 2002-11-15 | 2004-06-03 | President And Fellows Of Harvard College | Atomic layer deposition using metal amidinates |
| WO2004046417A3 (en) * | 2002-11-15 | 2005-03-10 | Harvard College | Atomic layer deposition using metal amidinates |
| JP2006511716A (en) * | 2002-11-15 | 2006-04-06 | プレジデント・アンド・フェロウズ・オブ・ハーバード・カレッジ | Atomic layer deposition using metal amidinates. |
| US7557229B2 (en) | 2002-11-15 | 2009-07-07 | President And Fellows Of Harvard College | Atomic layer deposition using metal amidinates |
| EP2182088A1 (en) | 2002-11-15 | 2010-05-05 | President and Fellows of Harvard College | Atomic layer deposition using metal amidinates |
| US7737290B2 (en) | 2002-11-15 | 2010-06-15 | President And Fellows Of Harvard University | Atomic layer deposition using metal amidinates |
| JP2010156058A (en) * | 2002-11-15 | 2010-07-15 | President & Fellows Of Harvard College | Atomic layer deposition using metal amidinate |
| CN1726303B (en) * | 2002-11-15 | 2011-08-24 | 哈佛学院院长等 | Atomic layer deposition using metal amidinates |
| JP2011236223A (en) * | 2002-11-15 | 2011-11-24 | President & Fellows Of Harvard College | Atomic layer deposition using metal amidinate |
| CN102312214A (en) * | 2002-11-15 | 2012-01-11 | 哈佛学院院长等 | Use the ald of metal amidinates |
| JP2012162804A (en) * | 2002-11-15 | 2012-08-30 | President & Fellows Of Harvard College | Atomic layer deposition using metal amidinate |
| US8455672B2 (en) | 2002-11-15 | 2013-06-04 | President And Fellows Of Harvard | Atomic layer deposition using metal amidinates |
| CN102312214B (en) * | 2002-11-15 | 2013-10-23 | 哈佛学院院长等 | Atomic layer deposition using metal amidinates |
| CN102344460B (en) * | 2002-11-15 | 2014-05-28 | 哈佛学院院长等 | Atomic layer deposition using metal amidinates |
| US9029189B2 (en) | 2003-11-14 | 2015-05-12 | President And Fellows Of Harvard College | Bicyclic guanidines, metal complexes thereof and their use in vapor deposition |
| TWI633061B (en) * | 2015-09-28 | 2018-08-21 | 氣相成長股份有限公司 | Magnesium-based structural material, method for forming magnesium-based structural material, and novel compound |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2295392B (en) | 1998-03-25 |
| GB9523981D0 (en) | 1996-01-24 |
| GB9423614D0 (en) | 1995-01-11 |
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