IP Library Granted Patent US 9,200,167
Granted Patent B2
US 9,200,167 · App. 13/745,102 · Granted Dec 1, 2015

Alkoxyaminosilane compounds and applications thereof

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Quick Facts
Patent No.
US 9,200,167
App. No.
13/745,102
Granted
Dec 1, 2015
Kind
B2
Abstract

Alkoxyaminosilane compounds having formula I, and processes and compositions for depositing a silicon-containing film, are described herein: (R 1 R 2 )NSiR 3 OR 4 OR 5   Formula (I) wherein R 1 is independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group; R 2 and R 3 are each independently selected from hydrogen; a linear or branched C 1 to C 10 alkyl group; a C 3 to C 12 alkenyl group, a C 3 to C 12 alkynyl group, a C 4 to C 10 cyclic alkyl group, and a C 6 to C 10 aryl group; and R 4 and R 5 are each independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group.

Claims (32)

1. An alkoxyaminosilane for depositing a silicon-containing film having a general formula (I):

(R 1 R 2 )NSiR 3 OR 4 OR 5   Formula (I)

wherein R 1 is independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group; R 2 and R 3 are each independently selected from hydrogen; a linear or branched C 1 to C 10 alkyl group; a C 3 to C 12 alkenyl group, a C 3 to C 12 alkynyl group, a C 4 to C 10 cyclic alkyl group, and a C 6 to C 10 aryl group; and R 4 and R 5 are each independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group, wherein R 1 and R 2 are linked to form a ring or R 1 and R 2 are not linked to form a ring and wherein R 4 and R 5 are linked to form a ring or R 4 and R 5 are not linked to form a ring; and

wherein R 1 is selected from tert-butyl and tert-pentyl; and R 4 and R 5 comprise C 1 to C 5 alkyl groups selected from ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, and tert-butyl.

2. The alkoxyaminosilane of claim 1 , wherein R 4 and R 5 are linked to form a ring.

3. The alkoxyaminosilane of claim 1 comprising diethoxy(tert-butylamino)silane.

4. A deposition process for depositing a silicon-containing film using at least one precursor comprising an alkoxyaminosilane having a general formula (I):

(R 1 R 2 )NSiR 3 OR 4 OR 5   Formula (I)

wherein R 1 is independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group; R 2 and R 3 are each independently selected from hydrogen; a linear or branched C 1 to C 10 alkyl group; a C 3 to C 12 alkenyl group, a C 3 to C 12 alkynyl group, a C 4 to C 10 cyclic alkyl group, and a C 6 to C 10 aryl group; and R 4 and R 5 are each independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group wherein R 1 and R 2 are linked to form a ring or R 1 and R 2 are not linked to form a ring and wherein R 4 and R 5 are linked to form a ring or R 4 and R 5 are not linked to form a ring; and

wherein R 1 is selected from tert-butyl and tert-pentyl; and R 4 and R 5 comprise C 1 to C 5 alkyl groups selected from ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, and tert-butyl.

5. The process of claim 4 , wherein R 3 comprises H.

6. The process of claim 4 , wherein the deposition process is selected from the group consisting of cyclic CVD (CCVD), MOCVD (Metal Organic CVD), thermal chemical vapor deposition, plasma enhanced chemical vapor deposition (PECVD), high density PECVD, photon assisted CVD, plasma-photon assisted (PPECVD), cryogenic chemical vapor deposition, chemical assisted vapor deposition, hot-filament chemical vapor deposition, CVD of a liquid polymer precursor, deposition from supercritical fluids, and low energy CVD (LECVD), and flowable chemical vapor deposition.

7. The process of claim 4 , wherein the deposition process is selected from the group consisting of atomic layer deposition (ALD), plasma enhanced ALD (PEALD), and plasma enhanced cyclic CVD (PECCVD) process.

8. The process of claim 4 , wherein the deposition process is flowable chemical vapor deposition (FCVD).

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

the precursor having a general formula (I):

(R 1 R 2 )NSiR 3 OR 4 OR 5   Formula (I)

wherein R 1 is independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group; R 2 and R 3 are each independently selected from hydrogen; a linear or branched C 1 to C 10 alkyl group; a C 3 to C 12 alkenyl group, a C 3 to C 12 alkynyl group, a C 4 to C 10 cyclic alkyl group, and a C 6 to C 10 aryl group; and R 4 and R 5 are each independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group wherein R 1 and R 2 are linked to form a ring or R 1 and R 2 are not linked to form a ring and wherein R 4 and R 5 are linked to form a ring or R 4 and R 5 are not linked to form a ring; and and wherein R 1 is selected from tert-butyl and tert-pentyl; and R 4 and R 5 comprise C 1 to C 5 alkyl groups selected from ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, and tert-butyl; and

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

10. The vessel of claim 9 wherein the vessel is comprised of stainless steel.

11. A composition for the deposition of a dielectric film comprising:

an alkoxyaminosilane having a general formula (I):

(R 1 R 2 )NSiR 3 OR 4 OR 5   Formula (I)

wherein R 1 is independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group; R 2 and R 3 are each independently selected from hydrogen; a linear or branched C 1 to C 10 alkyl group; a C 3 to C 12 alkenyl group, a C 3 to C 12 alkynyl group, a C 4 to C 10 cyclic alkyl group, and a C 6 to C 10 aryl group; and R 4 and R 5 are each independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group wherein R 1 and R 2 are linked to form a ring or R 1 and R 2 are not linked to form a ring and wherein R 4 and R 5 are linked to form a ring or R 4 and R 5 are not linked to form a ring and wherein R 1 is selected from tert-butyl and tert-pentyl; and R 4 and R 5 comprise C 1 to C 5 alkyl groups selected from ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, and tert-butyl; and

a silicon precursor selected from the group consisting of bis(tert-butylamino)silane (BTBAS), tris(dimethylamino)silane (TRDMAS), tetraethoxysilane (TEOS), triethoxysilane (TES), di-tert-butoxysilane (DTBOS), di-tert-pentoxysilane (DTPOS), methyltriethoxysilane (MTES), tetramethoxysilane (TMOS), trim ethoxysilane (TMOS), methyltrimethoxysilane (MTMOS), di-tert-butoxymethylsilane, di-tert-butoxyethylsilane, di-tert-pentoxymethylsilane, and di-tert-pentoxyethylsilane.

12. The composition of claim 11 wherein the alkoxyaminosilane is selected from the group consisting of di-ethoxy(tert-butylamino) silane, diethoxy(tert-pentylamino)silane, diethoxy(tert-butylamino)silane, diethoxy(tert-pentylamino)silane, diethoxy(iso-propoxyamino)silane, di-tert-butoxy(tert-butylamino)silane, di-tert-pentoxy(tert-butylamino)silane.

13. The composition of claim 12 wherein the composition is selected from the group consisting of: tetraethoxysilane (TEOS) and di-ethoxy(tert-butylamino)silane; tetraethoxysilane (TEOS) and diethoxy(tert-pentylamino)silane; tetraethoxysilane(TEOS) and diethoxy(iso-propoxyamino)silane; triethoxysilane (TES) and diethoxy(tert-butylamino) silane; triethoxysilane (TES) and diethoxy(tert-pentylamino)silane; di-tert-butoxysilane (DTBOS) and di-tert-butoxy(tert-butylamino)silane; and di-tert-pentoxysilane (DTPOS) and di-tert-pentoxy(tert-butylamino) silane.

14. An alkoxyaminosilane for depositing a silicon-containing film having a general formula (I):

(R 1 R 2 )NSiR 3 OR 4 OR 5   Formula (I)

wherein R 1 is independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group; R 3 is selected from hydrogen; a linear or branched C 1 to C 10 alkyl group; a C 3 to C 12 alkenyl group, a C 3 to C 12 alkynyl group, a C 4 to C 10 cyclic alkyl group, and a C 6 to C 10 aryl group; and R 4 and R 5 are each independently selected from a linear or branched C 1 to C 10 alkyl group; a C 2 to C 12 alkenyl group; a C 2 to C 12 alkynyl group; a C 4 to C 10 cyclic alkyl group; and a C 6 to C 10 aryl group wherein R 1 and R 2 are linked to form a, ring or R 1 and R 2 are not linked to form a ring and wherein R 4 and R 5 are linked to form a ring R 4 and R 5 are not linked to form a ring; and wherein R 1 is selected from tert-butyl and tert-pentyl; and R 4 and R 5 comprise C 1 to C 5 alkyl groups selected from ethyl, n-propyl, iso propyl, n-butyl, sec-butyl, iso-butyl, and tert-butyl.

15. The alkoxyaminosilane of claim 14 wherein R 4 and R 5 are linked to form a ring.

16. An alkoxyaminosilane comprising at least one selected from the group consisting of di-ethoxy(tert-butylamino)silane, diethoxy(tert-pentylamino)silane, diethoxy(iso-propoxyamino)silane, diethoxy(tert-butylamino)silane, diethoxy(tert-pentylamino)silane, diethoxy(iso-propoxyamino)silane, di-tert-butoxy(methylamino)silane, di-tert-butoxy(ethylamino)silane, ditert-butoxy(iso-propylamino)silane, di-tert-butoxy(n-butylamino)silane, di-tert-butoxy(sec-butylamino)silane, di-tert-butoxy(iso-butylamino)silane, di-tert-butoxy(tert-butylamino)silane, di-tert-pentoxy(methylamino)silane, di-tert-pentoxy(ethylamino)silane, di-tert-pentoxy(iso-propylamino)silane, di-tert-pentoxy(n-butylamino)silane, di-tert-pentoxy(sec-butylamino)silane, di-tert-pentoxy(iso-butylamino)silane, di-tert-pentoxy(tert-butylamino)silane, dimethoxy(phenylmethylamino)silane, diethoxy(phenylmethylamino)silane, dimethoxy(phenylmethylamino)methylsilane, diethoxy(phenylmethylamino)methylsilane, dimethoxy(cis-2,6-dimethylpiperidino)silane, diethoxy(cis-2,6-dimethylpiperidino)silane, and dimethoxy(cis-2,6-dimethylpiperidino)methylsilane.

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 Jan 31, 2013
From: SPENCE, DANIEL P.; PEARLSTEIN, RONALD MARTIN; LEI, XINJIAN; XIAO, MANCHAO; HO, RICHARD; O'NEILL, MARK LEONARD; CHANDRA, HARIPIN
To: AIR PRODUCTS AND CHEMICALS, INC.
Reel/Frame 029730/0880 →