Patent · US8771807B2 · B2 · US

Organoaminosilane precursors and methods for making and using same

(11) Publication number

US8771807B2

(21) Application number

13/474,076

(22) Filing date

2012-05-17

(30) Priority date

2011-05-24

(43) Publication date

2014-07-08

(45) Date of grant

2014-07-08

(52) CPC

C07F Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium: 7/10, 7/025
C23C Coating metallic material; coating material with metallic material; surface treatment of metallic material by diffusion into the surface, by chemical conversion or substitution; coating by vacuum evaporation, by sputtering, by ion implantation or by chemical vapour deposition, in general: 16/24, 16/30, 16/308, 16/32, 16/345, 16/347, 16/401, 16/402, 16/45553
H10P Generic processes or apparatus for the manufacture or treatment of devices covered by class H10: 14/6339, 14/6687, 14/69215, 14/6922

(73) Assignee

XIAO MANCHAO; LEI XINJIAN; HAN BING; O'NEILL MARK LEONARD; PEARLSTEIN RONALD MARTIN; HO RICHARD; CHANDRA HARIPIN; DERECSKEI-KOVACS AGNES; AIR PROD & CHEM

(54) Title

Organoaminosilane precursors and methods for making and using same

(57) Abstract

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.

Full text

View on Google Patents

Claims (10)

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.
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.
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.
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.
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.
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.
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.
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.
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.
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.

Citations (97)

EP0481706A1
EP1149934A2
EP1724373A1
EP1967609A2
EP2392691A1
GB1123252A
JP2000195801A
JP2001156063A
JP2005026244A
JP2009516906A
JP2010043081A
JP2012532193A
JPH06132276A
JPH06132284A
JPH07235535A
JPH08227890A
KR20050018641A
US2002086541A1
US2002175393A1
US2003124818A1
US2005048204A1
US2005085098A1
US2005163927A1
US2006022803A1
US2006045986A1
US2006051975A1
US2006062913A1
US2006099831A1
US2006216950A1
US2006228903A1
US2006258173A1
US2007160774A1
US2007275166A1
US2008038936A1
US2008260969A1
US2009069588A1
US2009075490A1
US2009205568A1
US2010209624A1
US2011136347A1
US2011178322A1
US2012178953A1
US2013022745A1
US4200666A
US4863755A
US4992299A
US5008422A
US5234869A
US5250473A
US5382550A
US5458689A
US5622784A
US5656076A
US5772757A
US5837056A
US5874368A
US6153261A
US6268299B1
US6391803B1
US6486015B1
US6486083B1
US6500772B2
US6559074B1
US6586056B2
US6630413B2
US6716772B2
US6890869B2
US6974780B2
US7098150B2
US7122222B2
US7125582B2
US7172792B2
US7332618B2
US7351670B2
US7365029B2
US7446217B2
US7462376B2
US7473655B2
US7482286B2
US7510984B2
US7531679B2
US7601652B2
US7651961B2
US7713346B2
US7786320B2
US7875556B2
US7932413B2
WO02065508A2
WO2004010467A2
WO2004017383A2
WO2004030071A1
WO2005080628A2
WO2005093126A1
WO2006036538A2
WO2006097525A2
WO2007002040A2
WO2011005653A1

Record as JSON

{
  "publication_number": "US8771807B2",
  "country": "US",
  "kind": "B2",
  "title": "Organoaminosilane precursors and methods for making and using same",
  "abstract": "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.",
  "claims": [
    "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."
  ],
  "cpc": [
    "C07F 7/10",
    "C07F 7/025",
    "C23C 16/24",
    "C23C 16/30",
    "C23C 16/308",
    "C23C 16/32",
    "C23C 16/345",
    "C23C 16/347",
    "C23C 16/401",
    "C23C 16/402",
    "C23C 16/45553",
    "H10P 14/6339",
    "H10P 14/6687",
    "H10P 14/69215",
    "H10P 14/6922"
  ],
  "assignees": [
    "XIAO MANCHAO",
    "LEI XINJIAN",
    "HAN BING",
    "O'NEILL MARK LEONARD",
    "PEARLSTEIN RONALD MARTIN",
    "HO RICHARD",
    "CHANDRA HARIPIN",
    "DERECSKEI-KOVACS AGNES",
    "AIR PROD & CHEM"
  ],
  "filing_date": "2012-05-17",
  "publication_date": "2014-07-08",
  "grant_date": "2014-07-08",
  "priority_date": "2011-05-24",
  "application_number": "US-201213474076-A",
  "family_id": "46197051",
  "citations": [
    "EP0481706A1",
    "EP1149934A2",
    "EP1724373A1",
    "EP1967609A2",
    "EP2392691A1",
    "GB1123252A",
    "JP2000195801A",
    "JP2001156063A",
    "JP2005026244A",
    "JP2009516906A",
    "JP2010043081A",
    "JP2012532193A",
    "JPH06132276A",
    "JPH06132284A",
    "JPH07235535A",
    "JPH08227890A",
    "KR20050018641A",
    "US2002086541A1",
    "US2002175393A1",
    "US2003124818A1",
    "US2005048204A1",
    "US2005085098A1",
    "US2005163927A1",
    "US2006022803A1",
    "US2006045986A1",
    "US2006051975A1",
    "US2006062913A1",
    "US2006099831A1",
    "US2006216950A1",
    "US2006228903A1",
    "US2006258173A1",
    "US2007160774A1",
    "US2007275166A1",
    "US2008038936A1",
    "US2008260969A1",
    "US2009069588A1",
    "US2009075490A1",
    "US2009205568A1",
    "US2010209624A1",
    "US2011136347A1",
    "US2011178322A1",
    "US2012178953A1",
    "US2013022745A1",
    "US4200666A",
    "US4863755A",
    "US4992299A",
    "US5008422A",
    "US5234869A",
    "US5250473A",
    "US5382550A",
    "US5458689A",
    "US5622784A",
    "US5656076A",
    "US5772757A",
    "US5837056A",
    "US5874368A",
    "US6153261A",
    "US6268299B1",
    "US6391803B1",
    "US6486015B1",
    "US6486083B1",
    "US6500772B2",
    "US6559074B1",
    "US6586056B2",
    "US6630413B2",
    "US6716772B2",
    "US6890869B2",
    "US6974780B2",
    "US7098150B2",
    "US7122222B2",
    "US7125582B2",
    "US7172792B2",
    "US7332618B2",
    "US7351670B2",
    "US7365029B2",
    "US7446217B2",
    "US7462376B2",
    "US7473655B2",
    "US7482286B2",
    "US7510984B2",
    "US7531679B2",
    "US7601652B2",
    "US7651961B2",
    "US7713346B2",
    "US7786320B2",
    "US7875556B2",
    "US7932413B2",
    "WO02065508A2",
    "WO2004010467A2",
    "WO2004017383A2",
    "WO2004030071A1",
    "WO2005080628A2",
    "WO2005093126A1",
    "WO2006036538A2",
    "WO2006097525A2",
    "WO2007002040A2",
    "WO2011005653A1"
  ]
}

Record 2,135 of 5,000 in Patents full text (MLC-0201). Request the full dataset.