Organoaminosilanes and methods for making same
First Claim
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1. A method for preparing a compound selected from a group consisting of organoaminosilane, an organoaminodisilane, and an organoaminocarbosilane, the method comprising the steps of:
- reacting at least one imine having a formula R—
N═
CR′
R″
wherein R, R′ and
R″
are each independently selected from hydrogen, a C1-10 linear alkyl group, a C3-10 branched alkyl, a C3-10 cyclic alkyl group, a C2-10 alkenyl group, a C4-10 aromatic group, a C4-10 heterocyclic group, a C1-10 linear organoamino group, a C2-10 branched organoamino group, a silyl group, a C1-10 linear carbosilyl group, and a C2-10 branched carbosilyl group, wherein at least one of R′ and
R″
or R and R′
, or none of R′ and
R″
or R and R′
are be linked to form a substituted or unsubstituted cyclic ring and a silicon source selected from the group consisting of silane, disilane, methylsilane, ethylsilane, diethylsilane, phenylsilane, 1,4-disilabutane, 1,3-disilapropane, 2-methyl-1,3-disilapropane, 1-silacyclopentane, 1-methyl-1-silacyclopentane, 1-silacyclobutane, and 1,3-disilacyclobutane, in the presence of a catalyst, wherein the catalyst is not a calcium hydride complex under reaction conditions sufficient for the imine and silicon source to react and provide the compound.
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Abstract
Organoaminosilanes, such as without limitation di-iso-propylaminosilane (DIPAS), are precursors for the deposition of silicon containing films such as silicon-oxide and silicon-nitride films. Described herein are methods to make organoaminosilane compounds, or other compounds such as organoaminodisilanes and organoaminocarbosilanes, via the catalytic hydrosilylation of an imine by a silicon source comprising a hydridosilane.
11 Citations
8 Claims
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1. A method for preparing a compound selected from a group consisting of organoaminosilane, an organoaminodisilane, and an organoaminocarbosilane, the method comprising the steps of:
reacting at least one imine having a formula R—
N═
CR′
R″
wherein R, R′ and
R″
are each independently selected from hydrogen, a C1-10 linear alkyl group, a C3-10 branched alkyl, a C3-10 cyclic alkyl group, a C2-10 alkenyl group, a C4-10 aromatic group, a C4-10 heterocyclic group, a C1-10 linear organoamino group, a C2-10 branched organoamino group, a silyl group, a C1-10 linear carbosilyl group, and a C2-10 branched carbosilyl group, wherein at least one of R′ and
R″
or R and R′
, or none of R′ and
R″
or R and R′
are be linked to form a substituted or unsubstituted cyclic ring and a silicon source selected from the group consisting of silane, disilane, methylsilane, ethylsilane, diethylsilane, phenylsilane, 1,4-disilabutane, 1,3-disilapropane, 2-methyl-1,3-disilapropane, 1-silacyclopentane, 1-methyl-1-silacyclopentane, 1-silacyclobutane, and 1,3-disilacyclobutane, in the presence of a catalyst, wherein the catalyst is not a calcium hydride complex under reaction conditions sufficient for the imine and silicon source to react and provide the compound.- View Dependent Claims (2, 3, 4, 5)
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6. A method for preparing a compound selected from the group consisting of an organoaminosilane, an organoaminodisilane, and an organoaminocarbosilane, in the presence of a catalyst comprising an alkaline earth metal complex, the method comprising the steps of:
- reacting at least one imine having a formula R—
N═
CR′
R″
wherein R, R′ and
R″
are each independently selected from the group consisting of hydrogen, a C1-10 linear alkyl group, a C3-10 branched alkyl, a C3-10 cyclic alkyl group, a C2-10 alkenyl group, a C4-10 aromatic group, a C4-10 heterocyclic group, a C1-10 linear organoamino group, a C2-10 branched organoamino group, a silyl group, a C1-10 linear carbosilyl group, and a C2-10 branched carbosilyl group, wherein at least one of R′ and
R″
or R and R′
, or none of R′ and
R″
or R and R′
are be linked to form a substituted or unsubstituted cyclic ring and a silicon source comprising at least one hydridosilane wherein the hydridosilane has a formula R1R2R3SiH wherein R1 and R2 are each independently selected from the group consisting of, a C1-10 linear alkyl group, a C3-10 branched alkyl group, a C4-10 cyclic alkyl group, a C2-10 alkenyl group, a C4-10 aromatic group, a C4-10 heterocyclic group, a C1-10 linear organoamino group, a C2-10 branched organoamino group, a silyl group, a C1-10 linear carbosilyl group, and a C2-10 branched carbosilyl group, R3 is hydrogen and wherein at least one of R1 and R2, R1 and R3, R2 and R3 or none of R1 and R2, R1 and R3, or R2 and R3 are linked to form a substituted or unsubstituted cyclic ring.
- reacting at least one imine having a formula R—
-
7. A method of preparing an organoamine having a formula HN(R)(CHR′
- R″
) wherein R, R′ and
R″
are independently selected from the group consisting of hydrogen, a C1-10 linear alkyl group, a C3-10 branched alkyl group, a C3-10 cyclic alkyl group, a C2-10 alkenyl group, a C4-10 aromatic group, a C4-10 heterocyclic group, a C1-10 linear organoamino group, a C2-10 branched organoamino group, a C1-10 linear carbosilyl group, and a C2-10 branched carbosilyl groups wherein at least one of R′ and
R″
or R and R′
or none of R′ and
R″
or R and R′
are linked to form a substituted or an unsubstituted cyclic ring, the method comprising the steps of;reacting an imine having a formula R—
N═
CR′
R″
wherein R, R′ and
R″
are each independently selected from the group consisting of, hydrogen, a C1-10 linear alkyl group, a C3-10 branched alkyl group, a C3-10 cyclic alkyl group, a C2-10 alkenyl group, a C4-10 aromatic group, a C4-10 heterocyclic group, a C1-10 linear organoamino group, a C2-10 branched organoamino groups, a silyl group, a C1-10 linear carbosilyl group, and a C2-10 branched carbosilyl group wherein at least one of R′ and
R″
or R and R′
or none of R′ and
R″
or R and R′
are linked to form a substituted or unsubstituted cyclic ring and a silicon source comprising a hydridosilane in the presence of an alkaline earth metal catalyst under conditions sufficient for the imine and silicon source to react and provide a compound selected from an organoaminosilane, an organoaminodisilane, and an organoaminocarbosilane;reacting the compound with a proton source under conditions sufficient to provide the organoamine. - View Dependent Claims (8)
- R″
Specification
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Current AssigneeVersum Materials US Inc.
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Original AssigneeVersum Materials US Inc.
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InventorsXiao, Manchao, MacDonald, Matthew R., Ho, Richard, Lei, Xinjian
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Primary Examiner(s)Katakam, Sudhakar
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Assistant Examiner(s)Adzamli, Kofi
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Application NumberUS14/956,748Publication NumberTime in Patent Office650 DaysField of Search556410US Class CurrentCPC Class CodesC07F 7/025 without C-silicon linkagesC07F 7/10 containing nitrogen having ...
