Organoaminosilane precursors and methods for making and using same
View Patent ↗Described herein are organoaminosilane precursors which can be used to deposit silicon containing films which contain silicon and methods for making these precursors. Also disclosed herein are deposition methods for making silicon-containing films or silicon containing films using the organoaminosilane precursors described herein. Also disclosed herein are the vessels that comprise the organoaminosilane precursors or a composition thereof that can be used, for example, to deliver the precursor to a reactor in order to deposit a silicon-containing film.
1. An organoaminosilane represented by one of the following Formulas A, B, or C:
wherein R is independently selected from a C 3 to C 10 branched, alkyl group; a C 3 to C 10 cyclic alkyl group; a C 5 to C 10 aromatic group; a C 3 to C 10 saturated or unsaturated heterocyclic group; a linear or a branched C 3 to C 10 alkenyl group; a C 1 to C 10 alkoxy group; a C 1 to C 10 alkylamino group; and in Formula C, R can also be a silyl group with or without substituents;
wherein R 1 is independently selected from a C 3 to C 10 linear, branched alkyl group; a C 3 to C 10 cyclic alkyl group; a C 5 to C 10 aromatic group; a C 3 to C 10 saturated or unsaturated heterocyclic group; a hydrogen atom; a linear or a branched C 3 to C 10 alkenyl group; a C 1 to C 10 alkoxy group; a C 1 to C 10 alkylamino group; or a silyl group with substituents; and
wherein R 2 represents a single bond; a saturated or unsaturated, linear or branched, substituted or unsubstituted hydrocarbon chain wherein a number of carbon atoms ranges ranging from 1 to 10; a saturated or unsaturated carbocyclic or heterocyclic ring; SiR 2 ; or SiH 2 , and
wherein R and R 1 in Formula A are also combinable to form a cyclic group and
wherein anyone or more of R, R 1 and R 2 in Formula C are also combinable to form a cyclic group
provided that the organoaminosilane is one selected from the group consisting of the following:
(a) the organoaminosilane comprises 1-silyl-7-azaindole;
(b) the organoaminosilane comprises N-silyl-2,5-dimethylpyrrole;
(c) the organoaminosilane having Formula B wherein R is a substituted C 5 -C 10 aromatic group comprising one or more of the following substituents: an alkyl group, an alkenyl group, and an alkoxy group;
(d) the organoaminosilane having Formula B wherein R is a substituted C 2 to C 10 alkyl group wherein the alkyl group is substituted with one or more of the following: a hetero atom, an aromatic group, an alkylamino group, or an alkoxy group.
2. A composition for the deposition of a silicon containing film comprising:
an organoaminosilane having Formula A, B, and C or mixtures thereof:
wherein R is independently selected from a C 1 to C 10 linear or branched alkyl group; a C 3 to C 10 cyclic alkyl group; a C 5 to C 10 aromatic group; a C 3 to C 10 saturated or unsaturated heterocyclic group; a linear or a branched C 3 to C 10 alkenyl group; a C 1 to C 10 alkoxy group; a C 1 to C 10 alkylamino group; and in Formula C, R can also be a silyl group with or without substituents; R 1 is independently selected from a C 3 -C 10 linear or branched alkyl group; a C 3 to C 10 cyclic alkyl group; a C 5 to C 10 aromatic group; a C 3 to C 10 saturated or unsaturated heterocyclic group; a hydrogen atom; a linear or a branched C 3 to C 10 alkenyl group; a C 1 to C 10 alkoxy group; a C 1 to C 10 alkylamino group; or a silyl group with substituents; and R 2 represents a single bond; a saturated or unsaturated, linear or branched, substituted or unsubstituted, hydrocarbon chain wherein the number of carbon atoms ranges from 1 to 10; a saturated or unsaturated, carbocyclic or heterocyclic ring; SiR 2 ; or SiH 2 , and wherein R and R 1 in Formula A are also combinable to form a cyclic group; and
a solvent selected from the group consisting of an ether, a tertiary amine, a nitrile, a tertiary amino ether, or mixtures thereof.
3. The composition of claim 2 wherein the organoaminosilane and the solvent each has a boiling point and wherein the difference between the boiling point of the organoaminosilane and the boiling point of the solvent is 40° C. or less.
4. The composition of claim 2 wherein the organoaminosilane and the solvent each has a boiling point and wherein the difference between the boiling point of the organoaminosilane and the boiling point of the solvent is 20° C. or less.
5. An organoaminosilane of following Formula A:
wherein R is independently selected from a C 1 to C 10 linear or branched, alkyl group;
a C 3 to C 10 cyclic alkyl group; a C 5 to C 10 aromatic group; a C 3 to C 10 saturated or unsaturated heterocyclic group; a linear or a branched C 3 to C 10 alkenyl group; a C 1 to C 10 alkoxy group; or a C 1 to C 10 alkylamino group;
wherein R 1 is independently selected from a C 3 to C 10 linear, branched alkyl group; a C 3 to C 10 cyclic alkyl group; a C 5 to C 10 aromatic group; a C 3 to C 10 saturated or unsaturated heterocyclic group; a hydrogen atom; a linear or a branched C 3 to C 10 alkenyl group; a C 1 to C 10 alkoxy group; or a C 1 to C 10 alkylamino group; and
provided that R and R 1 in Formula A are one selected from the group consisting of the following:
(a) the organoaminosilane comprises 1-silyl-7-azaindole;
(b) R and R 1 are combined to form a 5 or 6 member heterocyclic substituted or unsubstituted, aliphatic ring and wherein the organoaminosilane comprises N-silyldecahydroquinoline;
(c) R and R 1 are the same substituents provided that both R and R 1 are not one of the following groups: ethyl, isopropyl, tert-butyl, isobutyl, sec-butyl, n-butyl, t-pentyl, and sec-pentyl groups; or
(d) R and R 1 are different substituents.
6. The organoaminosilane of claim 5 wherein R and R 1 are different substitutents and wherein the organoaminosilane is one selected from the group consisting of: N-propyl-isopropylaminosilane, N-methylcyclohexylaminosilane, N-ethylcyclohexylaminosilane-, allylphenylaminosilane, N-isopropylcyclohexylaminosilane, allylcyclopentylaminosilane, phenylcyclohexylaminosilane, and 2-(N-silylmethylamino)pyridine.
7. An organoaminosilane of following Formula B:
wherein R is selected from a C 6 to C 10 substituted aromatic group which is substituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, an amino group, and an alkoxy group or an unsubstituted aromatic group provided that R is not phenyl; a linear or a branched, substituted or unsubstituted C 3 to C 10 alkenyl group; a C 1 to C 10 alkoxyalkyl group; a C 1 to C 10 alkylamino or dialkylamino group; or a C 4 to C 10 linear or branched, substituted or unsubstituted alkyl group provided that R is not an unsubstituted tert-butyl, t-pentyl, or cyclohexyl group.
8. The organoaminosilane of claim 7 which is one selected from the group consisting of: N-(4-methoxyphenyl)disilazane, N-(3-methoxyphenyl)disilazane, N-(2-methoxyphenyl)disilazane, N-(4-chlorophenyl)disilazane, N-(2-chlorophenyl)disilazane, N-(2-ethylphenyl)disilazane, N-(2,6-diethylphenyl)disilazane, N-(2-propylphenyl)disilazane, N-(4-t-butylphenyl)disilazane, N-(4-iso-propylphenyl)disilazane, N-(2-iso-propylphenyl)disilazane, N-(3-ethylphenyl)disilazane, N-(4-sec-butylphenyl)disilazane, N-(4-vinylphenyl)disilazane, N-(3-methylphenyl)disilazane, N-(4-methylphenyl)disilazane, N-(2,4,6-trimethylphenyl)disilazane, and N-(2, 6-di-isopropylphenyl)disilazane.
9. An organoaminosilane selected from the group consisting of:
1-N-(2-pyridyl)disilazane, N,N-disilyl-2-aminopyrimidine, N-(4-methyl-2-pyridyl)disilazane, N-(6-methyl-2-pyridyl)disilazane, N-(3-methyl-2-pyridyl)disilazane, N-(5-methyl-2-pyridyl)disilazane, and N-[2-(4-methylpyrimidino)amino]disilazane.
10. An organoaminosilane selected from the group consisting of, N-(2-dimethylamino-1-methylethyl)disilazane, N-(2-dimethylaminoethyl)disilazane, N-(1-cyclohexylethyl)disilazane, N,N-disilylcumylamine, N-[3,3-dimethylbutyl-2]ldisilazane, N,N-disilyl-2-picolylamine, N,N-disilyl-2-(2-pyridyl)ethylamine, and N,N-disilyl-1-(4-methylphenyl)ethylamine.