Monoaminosilane compounds

Patent metadata

Field	Value
Publication number	US-10030038-B2
Application number	US-201515314323-A
Country	US
Kind code	B2
Filing date	May 29, 2015
Priority date	May 30, 2014
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

Disclosed is a compound of formula (I): (R1R2N)SinH2n+1 (I), wherein subscript n is an integer from 3 to 9; and each R1 and R2 independently is (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, or phenyl; or R1 is H and R2 is (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, or phenyl; or R1 and R2 are bonded together to be -R1a R2a wherein -R1a-R2a- is (C2-C6)alkylene. Also disclosed are a method of making, intermediates useful therein, method of using, and composition comprising the compound of formula (I).

First claim

What is claimed is:

1. A compound of formula (I):
(R 1 R 2 N)Si n H 2n+1   (I)

wherein subscript n is 5 or an integer from 7 to 9; and each R 1 and R 2 independently is (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, or phenyl; or R 1 is H and R 2 is (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, or phenyl; or R 1 and R 2 are bonded together to be -R 1a -R 2a - wherein -R 1a -R 2a - is (C 2 -C 5 )alkylene, and wherein when n=5 the compound of formula (I) is according to formula (I-l) R 1 R 2 N—SiH 2 Si(SiH 3 ) 3 (I-l).

2. The compound of claim 1 wherein each R 1 and R 2 independently is (C 1 -C 6 )alkyl; or R 1 is (C 1 -C 6 )alkyl and R 2 is (C 3 -C 5 )alkyl; or R 1 is methyl or ethyl and R 2 is isopropyl, sec-butyl, iso-butyl, or tert-butyl; or each R 1 and R 2 independently is isopropyl, sec-butyl, iso-butyl, or tert-butyl; or R 1 is methyl and R 2 is tert-butyl; or each R 1 and R 2 independently is (C 3 -C 4 )alkyl; or each R 1 and R 2 is isopropyl.

3. The compound of claim 1 wherein R 1 and R 2 are bonded together to be -R 1a -R 2a - wherein -R 1a -R 2a - is (C 3 -C 5 )alkylene.

4. The compound of claim 1 comprising a compound of formula R 1 R 2 N—SiH 2 Si(SiH 3 ) 2 SiH 2 Si(SiH 3 ) 3 (I-m), wherein R 1 and R 2 are as defined in claim 1 .

5. The compound according to formula (I) of claim 1 that is 1-(diisopropylamino)-2,2-disilyltrisilane; or
1-(diisopropylamino)-2,2,4,4-tetrasilylpentasilane.

6. A composition comprising the compound of claim 1 and at least one additional ingredient that is different than the compound of any one of the preceding claims.

7. A method of making a compound of formula (I):
(R 1 R 2 N)Si n H 2n+1   (I)

wherein subscript n is an integer from 3 to 9; and each R 1 and R 2 independently is (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, or phenyl; or R 1 is H and R 2 is (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, or phenyl; or R 1 and R 2 are bonded together to be -R 1a -R 2a - wherein -R 1a -R 2a - is (C 2 -C 5 )alkylene, the method comprising:
Contacting a compound of formula (c1): (R 1 R 2 N)Si n X 2n+1 (c1), wherein each X independently is a halogen atom selected from Cl, Br, and I; and n, R 1 and R 2 are as defined above, with an aluminum hydride to give a mixture of the compound of formula (I) and at least one reaction by-product.

8. A method of making a silicon-containing material, the method comprising subjecting a source gas comprising the compound of claim 1 to silicon deposition conditions in the presence of a substrate, to give a silicon-containing material formed on the substrate.

9. A method of making a compound of formula (I):
(R 1 R 2 N)Si n H 2n+1   (I)

wherein subscript n is an integer from 3 to 9; and each R 1 and R 2 independently is (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, or phenyl; or R 1 is H and R 2 is (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, or phenyl; or R 1 and R 2 are bonded together to be -R 1a -R 2a - wherein -R 1a -R 2a - is (C 2 -C 5 )alkylene, the method comprising:
contacting a compound of formula (d1): R 1 R 2 NH (d1) with a compound of formula (d2) Si n H 2(n+1) (d2), wherein n, R 1 and R 2 are as defined above, in the presence of a catalyst, wherein the catalyst comprises at least one the main group elements Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, B, Al, Ga, In, TI, C, Si, Ge, Sn, Pb, N, P, As, Bb, Bi, O, S, Se, Te, F, Cl, Br, I, An, Cd, or Hg to give a reaction mixture;
maintaining the reaction mixture at a temperature between about 0° C. to about 250° C.;
allowing the reaction to proceed to form the compound of formula (I) above;
separating the compound of formula (I) of the compound of formula (I) from the reaction mixture;
wherein the reaction mixture temperature may vary during the synthesis and is maintained such that the temperature of the reaction mixture is not allowed to drop below about 0° C. and not exceed about 250° C.

10. The method of claim 9 , wherein the catalyst comprises at least one of the elements Mg, Ca, Sr, Ba, B, Al, Ga, Ge or Sn.

Assignees

• Dow Corning
• Dow Silicones Corp

Inventors

• Rekken Brian D
• Zhou Xiaobing

Classifications

• C07F7/10 Primary

  containing nitrogen {having a Si-N linkage} · CPC title

• C07F7/126

  by reactions involving the formation of Si-Y linkages, where Y is not a carbon or halogen atom · CPC title

• C07F7/12

  Organo silicon halides · CPC title

• C23C16/18

  from metallo-organic compounds · CPC title