Organoaminosilanes and methods for making same
US-2015246937-A1 · Sep 3, 2015 · US
US9969756B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9969756-B2 |
| Application number | US-201515512968-A |
| Country | US |
| Kind code | B2 |
| Filing date | Sep 23, 2015 |
| Priority date | Sep 23, 2014 |
| Publication date | May 15, 2018 |
| Grant date | May 15, 2018 |
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Disclosed are Si-containing film forming compositions comprising carbosilane substituted amine precursors. The carbosilane substituted amine precursors have the formula (R 1 ) a N(—SiHR 2 —CH 2 —SiH 2 R 3 ) 3−a , wherein a=0 or 1; R 1 is H, a C1 to C6 alkyl group, or a halogen; R 2 and R 3 is each independently H; a halogen; an alkoxy group having the formula OR′, wherein R′ is an alkyl group (C1 to C6); or an alkylamino group having the formula NR″ 2 , wherein each R″ is independently H, a C1-C6 alkyl group, a C1-C6 alkenyl group, or a C3-C10 aryl or heterocycle group. Also disclosed are methods of synthesizing the carbosilane substituted amine precursors and their use for deposition processes.
Opening claim text (preview).
We claim: 1. A Si-containing film forming composition comprising a carbosilane substituted amine precursor having the formula (R 1 ) a N(—SiHR 2 —CH 2 —SiH 2 R 3 ) 3−a , wherein a=0 or 1; R 1 is H, a C1 to C6 alkyl group, or a halogen; R 2 and R 3 is each independently H, a halogen, an alkoxy group having the formula OR′, wherein R′ is an alkyl group (C1 to C6), or an alkylamino group having the formula NR″ 2 , wherein each R″ is independently H, a C1-C6 alkyl group, a C1-C6 alkenyl group, or a C3-C10 aryl or heterocycle group. 2. The Si-containing film forming composition of claim 1 , wherein a=0 and the carbosilane substituted amine precursor has the formula N(—SiHR 2 —CH 2 —SiH 2 R 3 ) 3 . 3. The Si-containing film forming composition of claim 2 , wherein the carbosilane substituted amine precursor is selected from the group consisting of N(SiH 2 —CH 2 —SiH 2 (Cl)) 3 , N(SiH 2 —CH 2 —SiH 2 (Br)) 3 , N(SiH 2 —CH 2 —SiH 2 (I)) 3 , N(SiH 2 —CH 2 —SiH 2 (NH 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NMe 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NMeEt)) 3 , N(SiH 2 —CH 2 —SiH 2 (NEt 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NnPr 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NiPr 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NBu 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NiBu 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NtBu 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NAm 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NCyPentyl 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (Nhexyl 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NCyHex 2 )) 3 , N(SiH 2 —CH 2 —SiH 2 (NMeH)) 3 , N(SiH 2 —CH 2 —SiH 2 (NEtH)) 3 , N(SiH 2 —CH 2 —SiH 2 (NnPrH)) 3 , N(SiH 2 —CH 2 —SiH 2 (NiPrH)) 3 , N(SiH 2 —CH 2 —SiH 2 (NBuH)) 3 , N(SiH 2 —CH 2 —SiH 2 (NiBuH)) 3 , N(SiH 2 —CH 2 —SiH 2 (NtBuH)) 3 , N(SiH 2 —CH 2 —SiH 2 (NAmH)) 3 , N(SiH 2 —CH 2 —SiH 2 (OH)) 3 , N(SiH 2 —CH 2 —SiH 2 (OMe)) 3 , N(SiH 2 —CH 2 —SiH 2 (OEt)) 3 , N(SiH 2 —CH 2 —SiH 2 (OnPr)) 3 , N(SiH 2 —CH 2 —SiH 2 (OiPr)) 3 , N(SiH 2 —CH 2 —SiH 2 (OBu)) 3 , N(SiH 2 —CH 2 —SiH 2 (OiBu)) 3 , N(SiH 2 —CH 2 —SiH 2 (OtBu)) 3 , N(SiH 2 —CH 2 —SiH 2 (OAm)) 3 , N(SiH 2 —CH 2 —SiH 2 (OHexyl)) 3 , N(SiH 2 —CH 2 —SiH 2 (Cl)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (Br)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (I)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NH 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NMe 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NMeEt)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NEt 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NnPr 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NiPr 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NBu 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NiBu 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NtBu 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NHtBu)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NAm 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NHAm)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NCyPentyl 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (Nhexyl 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NCyHex 2 )) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NMeH)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NEtH)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NnPrH)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (NiPrH)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OH)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OMe)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OEt)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OnPr)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OiPr)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OBu)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OiBu)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OtBu)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OAm)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (OHexyl)) 2 (SiH 2 —CH 2 SiH 3 ), N(SiH 2 —CH 2 —SiH 2 (Cl))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (Br))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (I))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NH 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NMe 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NMeEt))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NEt 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NnPr 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NiPr 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NBu 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NiBu 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NtBu 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NHtBu))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NAm 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NHAm))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NCyPentyl 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (Nhexyl 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NCyHex 2 ))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NMeH))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NEtH))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NnPrH))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (NiPrH))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OH))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OMe))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OEt))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OnPr))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OiPr))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OBu))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OiBu))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OtBu))(SiH 2 —CH 2 SiH 3 ) 2 , N(SiH 2 —CH 2 —SiH 2 (OAm))(SiH 2 —CH 2 SiH 3 ) 2 , and N(SiH 2 —CH 2 —SiH 2 (OHexyl))(SiH 2 —CH 2 SiH 3 ) 2 . 4. The Si-containing film forming composition of claim 2 , wherein the carbosilane substituted amine precursor is selected from the group consisting of N(SiH 2 —CH 2 —SiH 3 ) 3 , N(Si(H)(Cl)—CH 2 —SiH 3 ) 3 , N(Si(H)(Br)—CH 2 —SiH 3 ) 3 , N(Si(H)(I)—CH 2 —SiH 3 ) 3 , N(Si(H)(NH 2 )—CH 2 —SiH 3 ) 3 , N(Si(H)(NMe 2 )-CH 2 —SiH 3 ) 3 , N(Si(H)(NEtMe)-CH 2 —SiH 3 ) 3 , N(Si(H)(NEt 2 )-CH 2 —SiH 3 ) 3 , N(Si(H)(NnPr 2 )—CH 2 —SiH 3 ) 3 , N(Si(H)(NiPr 2 )—CH 2 —SiH 3 ) 3 , N(Si(H)(NBu 2 )-CH 2 —SiH 3 ) 3 , N(Si(H)(NiBu 2 )-CH 2 —SiH 3 ) 3 , N(Si(H)(NtBu 2 )-CH 2 —SiH 3 ) 3 , N(Si(H)(NHtBu)-CH 2 —SiH 3 ) 3 , N(Si(H)(NAm 2 )—CH 2 —SiH 3 ) 3 , N(Si(H)(NHAm)—CH 2 —SiH 3 ) 3 , N(Si(H)(NCyPentyl 2 )-CH 2 —SiH 3 ) 3 , N(Si(H)(Nhexyl 2 )-CH 2 —SiH 3 ) 3 , N(Si(H)(NCyHex 2 )-CH 2 —SiH 3 ) 3 , N(Si(H)(NMeH)—CH 2 —SiH 3 ) 3 , N(Si(H)(NEtH)—CH 2 —SiH 3 ) 3 , N(Si(H)(NnPrH)—CH 2 —SiH 3 ) 3 , N(Si(H)(NiPrH)—CH 2 —SiH 3 ) 3 , N(Si(H)(NBuH)—CH 2 —SiH 3 ) 3 , N(Si(H)(NtBuH)—CH 2 —SiH 3 ) 3 , N(Si(H)(OH)—CH 2 —SiH 3 ) 3 , N(Si(H)(OMe)-CH 2 —SiH 3 ) 3 , N(Si(H)(OEt)-CH 2 —SiH 3 ) 3 , N(Si(H)(OnPr)—CH 2 —SiH 3 ) 3 , N(Si(H)(OiPr)—CH 2 —SiH 3 ) 3 , N(Si(H)(OBu)-CH 2 —SiH 3 ) 3 , N(Si(H)(OiBu)-CH 2 —SiH 3 ) 3 , N(Si(H)(OtBu)-CH 2 —SiH 3 ) 3 , N(Si(H)(OAm)—CH 2 —SiH 3 ) 3 , N(Si(H)(OHexyl)-CH 2 —SiH 3 ) 3 , N(Si(H)(Cl)—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(Br)—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(I)—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NH 2 )—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NMe 2 )-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NMeEt)-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NEt 2 )-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NnPr 2 )—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NiPr 2 )—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NBu 2 )-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NiBu 2 )-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NtBu 2 )-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NHtBu)-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NAm 2 )—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NHAm)—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NCyPentyl 2 )-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(Nhexyl 2 )-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NCyHex 2 )-CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NMeH)—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NEtH)—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NnPrH)—CH 2 —SiH 3 ) 2 (SiH 2 —CH 2 SiH 3 ), N(Si(H)(NiPrH)—CH 2 —SiH
containing silicon · CPC title
deposition by cyclic CVD, e.g. ALD, ALE or pulsed CVD · CPC title
Silicon, silicon germanium or germanium · CPC title
Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides · CPC title
Silicon dioxide · CPC title
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