Diaminosilane compounds

Patent metadata

Field	Value
Publication number	US-10030037-B2
Application number	US-201515314300-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): (R 1 R 2 N)Si n H 2n (NR 3 R 4 ) (I) wherein subscript n, R 1 , R 2 , R 3 and R 4 are as defined herein. 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
R 1 R 2 N—SiH 2 Si(SiH 3 ) 2 SiH 2 NR 3 R 4   (I-l),

R 1 R 2 N—SiH 2 Si(SiH 3 ) 2 SiH 2 Si(SiH 3 ) 2 SiH 2 NR 3 R 4   (I-n),

R 1 R 2 N—SiH(NR 3 R 4 )SiH(SiH 3 )SiH 2 SiH 3   (I-hh),

or
R 1 R 2 N—SiH(NR 3 R 4 )Si(SiH 3 ) 2 SiH 2 Si(SiH 3 ) 3   (I-II),

wherein R 1 is methyl, propyl, butyl, pentyl, hexyl, or (C 3 -C 6 )cycloalkyl, and each R 2 , R 3 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl; 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 each R 3 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl; 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 R 3 and R 4 are bonded together to be —R 3a —R 4a — wherein —R 3a —R 4a — is (C 2 -C 5 )alkylene; or R 1 and R 3 are bonded together to be —R 1a —R 3a — wherein —R 1a —R 3a — is (C 2 -C 5 )alkylene and each of R 2 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl.

2. A compound of claim 1 that is
1,3-bis(diisopropylamino)-2,2-disilyltrisilane; 1,1-bis(diisopropylamino)-2,2-disilyltrisilane, 1,5-bis(diisopropylamino)-2,2,4,4-tetrasilylpentasilane; or 1,1-bis(diisopropylamino)-2,2,4,4-tetrasilylpentasilane.

3. 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.

4. A method of making the compound of claim 1 of formula
R 1 R 2 N—SiH 2 Si(SiH 3 ) 2 SiH 2 NR 3 R 4   (I-l),

R 1 R 2 N—SiH 2 Si(SiH 3 ) 2 SiH 2 Si(SiH 3 ) 2 SiH 2 NR 3 R 4   (I-n),

R 1 R 2 N—SiH(NR 3 R 4 )SiH(SiH 3 )SiH 2 SiH 3   (I-hh),

or
R 1 R 2 N—SiH(NR 3 R 4 )Si(SiH 3 ) 2 SiH 2 Si(SiH 3 ) 3   (I-II),

R 1 is methyl, propyl, butyl, pentyl, hexyl, or (C 3 -C 6 )cycloalkyl, and each R 2 , R 3 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl; 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 each R 3 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl; 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 R 3 and R 4 are bonded together to be —R 3a —R 4a — wherein —R 3a —R 4a — is (C 2 -C 5 )alkylene; or R 1 and R 3 are bonded together to be —R 1a —R 3a — wherein —R 1a —R 3a — is (C 2 -C 6 )alkylene and each of R 2 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl, the method comprising:
Contacting a compound of formula (c1):
(R 1 R 2 N)Si n X 2n (NR 3 R 4 )  (c1),

 wherein each X independently is a halogen atom selected from CI, Br, and I; n is 5 or 9, and R 1 , R 2 , R 3 , and R 4 are as defined above, and where the compound of formula (c1) has the same silicon backbone structure as in one of formulas (I-l), (I-n), (I-hh), or (I-II),with an aluminum hydride to give a mixture of the compound of formula (I-l), (I-n), (I-hh), or (I-II) and at least one reaction by-product.

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

6. A method of making a compound as in claim 1 of formula
R 1 R 2 N—SiH 2 Si(SiH 3 ) 2 SiH 2 NR 3 R 4   (I-l),

R 1 R 2 N—SiH 2 Si(SiH 3 ) 2 SiH 2 Si(SiH 3 ) 2 SiH 2 NR 3 R 4   (I-n),

R 1 R 2 N—SiH(NR 3 R 4 )SiH(SiH 3 )SiH 2 SiH 3   (I-hh),

or
R 1 R 2 N—SiH(NR 3 R 4 )Si(SiH 3 ) 2 SiH 2 Si(SiH 3 ) 3   (I-II),

R 1 is methyl, propyl, butyl, pentyl, hexyl, or (C 3 -C 6 )cycloalkyl, and each R 2 , R 3 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl; 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 each R 3 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl; 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 R 3 and R 4 are bonded together to be —R 3a —R 4a — wherein —R 3a —R 4a — is (C 2 -C 5 )alkylene; or R 1 and R 3 are bonded together to be —R 1a —R 3a — wherein —R 1a —R 3a — is (C 2 -C 5 )alkylene and each of R 2 and R 4 independently is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl, the method comprising:
Contacting a compound of formula (d1):
(R 1 R 2 N)Si n H 2n+1   (d1)

with a compound of formula (d2)
(HNR 3 R 4 )  (d2),

wherein n is 5 or 9, R 1 , R 2 , R 3 , and R 4 are as defined above, and where the compound of formula (d1) has the same silicon backbone structure as in one of formulas (I-l), (I-n), (I-hh), or (I-II), in the presence of a catalyst, wherein the catalyst comprises at least one of 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, Zn, Cd, or Hg to give a reaction mixture;
maintaining the reaction mixture ast 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.

7. The method of claim 6 , 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

• H10P14/69433

  the material being a silicon nitride not containing oxygen, e.g. SixNy or SixByNz · CPC title

• H10P14/69215

  the material being a silicon oxide, e.g. SiO2 · CPC title

• H10P14/6687

  the compound comprising silicon and nitrogen · CPC title

• H10P14/6334

  using decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition (deposition by physical ablation of a target H10P14/6329) · CPC title

• H10P14/3411

  Silicon, silicon germanium or germanium · CPC title