IP Library Granted Patent US 9,613,799
Granted Patent B2
US 9,613,799 · App. 15/073,899 · Granted Apr 4, 2017

Methods for depositing films with organoaminodisilane precursors

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Quick Facts
Patent No.
US 9,613,799
App. No.
15/073,899
Granted
Apr 4, 2017
Kind
B2
Abstract

Described herein are precursors and methods for forming silicon-containing films. In one aspect, there is provided a precursor of Formula I: wherein R 1 is selected from linear or branched C 3 to C 10 alkyl group, linear or branched C 3 to C 10 alkenyl group, linear or branched C 3 to C 10 alkynyl group, C 1 to C 6 dialkylamino group, electron withdrawing group, and C 6 to C 10 aryl group; R 2 is selected from hydrogen, linear or branched C 1 to C 10 alkyl group, linear or branched C 3 to C 6 alkenyl group, linear or branched C 3 to C 6 alkynyl group, C 1 to C 6 dialkylamino group, C 6 to C 10 aryl group, linear or branched C 1 to C 6 fluorinated alkyl group, electron withdrawing group, and C 4 to C 10 aryl group; optionally wherein R 1 and R 2 are linked together to form ring selected from substituted or unsubstituted aromatic ring or substituted or unsubstituted aliphatic ring; and n=1 or 2.

Claims (21)

1. An organoaminodisilane precursor comprising a Si—N bond, a Si—Si bond, and a Si—H 3 group represented by the following Formula I below:

wherein R 1 is selected from a linear or branched C 3 to C 10 alkyl group, a linear or branched C 3 to C 10 alkenyl group, a linear or branched C 3 to C 10 alkynyl group, a C 1 to C 6 dialkylamino group, an electron withdrawing group, and a C 6 to C 10 aryl group; R 2 is selected from hydrogen, a linear or branched C 1 to C 10 alkyl group, a linear or branched C 3 to C 6 alkenyl group, a linear or branched C 3 to C 6 alkynyl group, a C 1 to C 6 dialkylamino group, a C 6 to C 10 aryl group, a linear or branched C 1 to C 6 fluorinated alkyl group, an electron withdrawing group, and a C 4 to C 10 aryl group; optionally wherein R 1 and R 2 are linked together to form a ring selected from a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring; and n=1 or 2; wherein R 1 and R 2 in Formula I cannot both be iso-propyl.

2. The organoaminodisilane precursor of claim 1 wherein the R 1 and R 2 are linked together to form a ring.

3. The organoaminodisilane precursor of claim 1 wherein R 1 and R 2 are the same provided that R 1 and R 2 are not methyl or ethyl.

4. The organoaminodisilane precursor of claim 1 selected from the group consisting of di-sec-butylaminodisilane, di-tert-butylaminodisilane, 2,6-dimethylpiperidinodisilane, 2,2,6,6-tetramethylpiperidinodisilane, cyclohexyl-iso-propylaminodisilane, phenylmethylaminodisilane, phenylethylaminodisilane, di-cyclohexylaminodisilane, trans-decahydroquinolinyldisilane, 1,1-bis(t-butylamino)disilane, 1,1-bis(tert-pentylamino)disilane, 1,1-bis(iso-propylamino)disilane, 1,1-bis(iso-propylmethlamino)disilane, 1,1-dipiperidinodisilane, 1,1-dipyrrolidinodisilane, 1,1-di(2,6-dimethylpiperidino)disilane, 1,1-bis(di-sec-butylamino)disilane.

5. The organoaminodisilane precursor of claim 4 comprising di-sec-butylaminodisilane.

6. The organoaminodisilane precursor of claim 4 comprising 2,6-dimethylpiperidinodisilane.

7. The organoaminodisilane precursor of claim 4 comprising phenylethylaminodisilane.

8. A composition comprising:

(a) at least one organoaminodisilane precursor comprising a Si—N bond, a Si—Si bond, and a Si—H 3 group represented by the following Formula I below:

wherein R 1 is selected from a linear or branched C 3 to C 10 alkyl group, a linear or branched C 3 to C 10 alkenyl group, a linear or branched C 3 to C 10 alkynyl group, a C 1 to C 6 dialkylamino group, an electron withdrawing group, and a C 6 to C 10 aryl group; R 2 is selected from hydrogen, a linear or branched C 1 to C 10 alkyl group, a linear or branched C 3 to C 6 alkenyl group, a linear or branched C 3 to C 6 alkynyl group, a C 1 to C 6 dialkylamino group, a C 6 to C 10 aryl group, a linear or branched C 1 to C 6 fluorinated alkyl group, an electron withdrawing group, and a C 4 to C 10 aryl group; optionally wherein R 1 and R 2 are linked together to form a ring selected from a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring; and n=1 or 2; and

(b) a solvent wherein the solvent has a boiling point and wherein the difference between the boiling point of the solvent and that of the at least one organoaminodisilane is 40° C. or less.

9. The composition of claim 8 wherein the organoaminodisilane comprises at least one selected from the group consisting of di-iso-propylaminodisilane, di-sec-butylaminodisilane, di-tert-butylaminodisilane, 2,6-dimethylpiperidinodisilane, 2,2,6,6-tetramethylpiperidinodisilane, cyclohexyl-iso-propylaminodisilane, phenylmethylaminodisilane, phenylethylaminodisilane, di-cyclohexylaminodisilane, trans-decahydroquinolinyldisilane, 1,1-(N,N′-di-tert-butylethylenediamino)disilane, 1,1-(N,N′-di-iso-propylethylenediamino)disilane, 1,1-bis(t-butylamino)disilane, 1,1-bis(tert-pentylamino)disilane, 1,1-bis(iso-propylamino)disilane, 1,1-bis(iso-propylmethlamino)disilane, 1,1-dipiperidinodisilane, 1,1-dipyrrolidinodisilane, 1,1-bis(diethylamino)disilane, 1,1-bis(di-iso-propylamino)disilane, 1,1-di(2,6-dimethylpiperidino)disilane, 1,1-bis(di-sec-butylamino)disilane.

10. The composition of claim 8 wherein the solvent comprises at least one selected from the group consisting of ether, tertiary amine, alkyl hydrocarbon, aromatic hydrocarbon, tertiary aminoether.

11. A vessel which is used to deliver a precursor for the deposition of a silicon-containing film, the vessel comprising:

at least one organoaminodisilane precursor comprising a Si—N bond, a Si—Si bond, and a Si—H 3 group represented by the following Formula I below:

wherein R 1 is selected from a linear or branched C 3 to C 10 alkyl group, a linear or branched C 3 to C 10 alkenyl group, a linear or branched C 3 to C 10 alkynyl group, a C 1 to C 6 dialkylamino group, an electron withdrawing group, and a C 6 to C 10 aryl group; R 2 is selected from hydrogen, a linear or branched C 1 to C 10 alkyl group, a linear or branched C 3 to C 6 alkenyl group, a linear or branched C 3 to C 6 alkynyl group, a C 1 to C 6 dialkylamino group, a C 6 to C 10 aryl group, a linear or branched C 1 to C 6 fluorinated alkyl group, an electron withdrawing group, and a C 4 to C 10 aryl group; optionally wherein R 1 and R 2 are linked together to form a ring selected from a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring; and n=1 or 2, and

wherein the purity of the precursor is about 98% or greater.

12. The vessel of claim 11 wherein the vessel is comprised of stainless steel.

13. The organoaminodisilane precursor of claim 1 wherein n=2 and R 1 and R 1 are linked together to form a ring.

14. The organoaminodisilane precursor of claim 1 wherein n=2 and R 1 and R 2 are linked together to form a ring.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Oct 7, 2019
From: CITIBANK, N.A., AS AGENT
To: VERSUM MATERIALS US, LLC
Reel/Frame 050647/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 20, 2017
From: AIR PRODUCTS AND CHEMICALS, INC.
To: VERSUM MATERIALS US, LLC
Reel/Frame 041772/0733 →
PATENT SECURITY AGREEMENT Recorded Oct 27, 2016
From: VERSUM MATERIALS US, LLC
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 040503/0442 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2016
From: XIAO, MANCHAO; LEI, XINJIAN; SPENCE, DANIEL P.; CHANDRA, HARIPIN; HAN, BING; O'NEILL, MARK LEONARD; MAYORGA, STEVEN GERARD; MALLIKARJUNAN, ANUPAMA
To: AIR PRODUCTS AND CHEMICALS, INC.
Reel/Frame 038762/0411 →