IP Library Granted Patent US 9,677,178
Granted Patent B2
US 9,677,178 · App. 14/940,249 · Granted Jun 13, 2017

Alkoxyaminosilane compounds and applications thereof

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Quick Facts
Patent No.
US 9,677,178
App. No.
14/940,249
Granted
Jun 13, 2017
Kind
B2
Abstract

Alkoxyaminosilane compound 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 (13)

1. An alkoxyaminosilane for depositing a silicon-containing film selected from the group consisting of di-ethoxy(tert-butylamino)methylsilane, diethoxy(tert-pentylamino)methylsilane, diethoxy(iso-propoxyamino)methylsilane, diethoxy(tert-butylamino)methylsilane, diethoxy(tert-pentylamino)methylsilane, diethoxy(iso-propoxyamino)methylsilane, di-tert-butoxy(methylamino)methylsilane, di-tert-butoxy(ethylamino)methylsilane, ditert-butoxy(iso-propylamino)methylsilane, di-tert-butoxy(n-butylamino)methylsilane, di-tert-butoxy(sec-butylamino)methylsilane, di-tert-butoxy(iso-butylamino)methylsilane, di-tert-butoxy(tert-butylamino)methylsilane, di-tert-pentoxy(methylamino)methylsilane, di-tert-pentoxy(ethylamino)methylsilane, di-tert-pentoxy(iso-propylamino)methylsilane, di-tert-pentoxy(n-butylamino)methylsilane, di-tert-pentoxy(sec-butylamino)methylsilane, di-tert-pentoxy(iso-butylamino)methylsilane, di-tert-pentoxy(tert-butylamino)methylsilane, dimethoxy(phenylmethylamino)methylsilane, and diethoxy(phenylmethylamino)methylsilane.

2. A deposition process for depositing a silicon-containing film using at least one precursor comprising an alkoxyaminosilane selected from the group consisting of di-ethoxy(tert-butylamino)methylsilane, diethoxy(tert-pentylamino)methylsilane, diethoxy(iso-propoxyamino)methylsilane, diethoxy(tert-butylamino)methylsilane, diethoxy(tert-pentylamino)methylsilane, diethoxy(iso-propoxyamino)methylsilane, di-tert-butoxy(methylamino)methylsilane, di-tert-butoxy(ethylamino)methylsilane, ditert-butoxy(iso-propylamino)methylsilane, di-tert-butoxy(n-butylamino)methylsilane, di-tert-butoxy(sec-butylamino)methylsilane, di-tert-butoxy(iso-butylamino)methylsilane, di-tert-butoxy(tert-butylamino)methylsilane, di-tert-pentoxy(methylamino)methylsilane, di-tert-pentoxy(ethylamino)methylsilane, di-tert-pentoxy(iso-propylamino)methylsilane, di-tert-pentoxy(n-butylamino)methylsilane, di-tert-pentoxy(sec-butylamino)methylsilane, di-tert-pentoxy(iso-butylamino)methylsilane, di-tert-pentoxy(tert-butylamino)methylsilane, dimethoxy(phenylmethylamino)methylsilane, and diethoxy(phenylmethylamino)methylsilane.

3. The process of claim 2 , 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.

4. The process of claim 2 , wherein the deposition process further comprises a nitrogen source selected from the group consisting of ammonia, hydrazine, monoalkylhydrazine, dialkylhydrazine, nitrogen, nitrogen/hydrogen, ammonia plasma, nitrogen plasma, nitrogen/hydrogen plasma, and mixture thereof.

5. The process of claim 2 , wherein the deposition process further comprises an oxygen source selected from the group consisting of water (H 2 O) (e.g., deionized water, purifier water, and/or distilled water, a mixture containing water and other organic liquid), oxygen (O 2 ), oxygen plasma, ozone (O 3 ), NO, NO 2 , water plasma, carbon monoxide (CO), carbon dioxide (CO 2 ) and combinations thereof.

6. The process of claim 2 , 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.

7. The process of claim 2 , wherein the deposition process is flowable chemical vapor deposition (FCVD).

8. A vessel which is used to deliver a precursor for the deposition of a silicon-containing film, the vessel comprising the precursor selected from the group consisting of di-ethoxy(tert-butylamino)methylsilane, diethoxy(tert-pentylamino)methylsilane, diethoxy(iso-propoxyamino)methylsilane, diethoxy(tert-butylamino)methylsilane, diethoxy(tert-pentylamino)methylsilane, diethoxy(iso-propoxyamino)methylsilane, di-tert-butoxy(methylamino)methylsilane, di-tert-butoxy(ethylamino)methylsilane, ditert-butoxy(iso-propylamino)methylsilane, di-tert-butoxy(n-butylamino)methylsilane, di-tert-butoxy(sec-butylamino)methylsilane, di-tert-butoxy(iso-butylamino)methylsilane, di-tert-butoxy(tert-butylamino)methylsilane, di-tert-pentoxy(methylamino)methylsilane, di-tert-pentoxy(ethylamino)methylsilane, di-tert-pentoxy(iso-propylamino)methylsilane, di-tert-pentoxy(n-butylamino)methylsilane, di-tert-pentoxy(sec-butylamino)methylsilane, di-tert-pentoxy(iso-butylamino)methylsilane, di-tert-pentoxy(tert-butylamino)methylsilane, dimethoxy(phenylmethylamino)methylsilane, diethoxy(phenylmethylamino)methylsilane; and

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

9. The vessel of claim 8 wherein the vessel is comprised of stainless steel.

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

an alkoxyaminosilane selected from the group consisting of di-ethoxy(tert-butylamino)methylsilane, diethoxy(tert-pentylamino)methylsilane, diethoxy(iso-propoxyamino)methylsilane, diethoxy(tert-butylamino)methylsilane, diethoxy(tert-pentylamino)methylsilane, diethoxy(iso-propoxyamino)methylsilane, di-tert-butoxy(methylamino)methylsilane, di-tert-butoxy(ethylamino)methylsilane, ditert-butoxy(iso-propylamino)methylsilane, di-tert-butoxy(n-butylamino)methylsilane, di-tert-butoxy(sec-butylamino)methylsilane, di-tert-butoxy(iso-butylamino)methylsilane, di-tert-butoxy(tert-butylamino)methylsilane, di-tert-pentoxy(methylamino)methylsilane, di-tert-pentoxy(ethylamino)methylsilane, di-tert-pentoxy(iso-propylamino)methylsilane, di-tert-pentoxy(n-butylamino)methylsilane, di-tert-pentoxy(sec-butylamino)methylsilane, di-tert-pentoxy(iso-butylamino)methylsilane, di-tert-pentoxy(tert-butylamino)methylsilane, dimethoxy(phenylmethylamino)methylsilane, and diethoxy(phenylmethylamino)methylsilane; and

a silicon precursor selected from the group consisting of bis(tert-butylamino)silane (BTBAS), bis(diethylamino)silane (BDEAS), di-iso-propylaminosilane (DIPAS), di-sec-butylaminosilane (DSBAS), tris(dimethylamino)silane (TRDMAS), tetraethoxysilane (TEOS), triethoxysilane (TES), di-tert-butoxysilane (DTBOS), di-tert-pentoxysilane (DTPOS), methyltriethoxysilane (MTES), tetramethoxysilane (TMOS), trimethoxysilane (TMOS), methyltrimethoxysilane (MTMOS), di-tert-butoxymethylsilane, di-tert-butoxyethylsilane, di-tert-pentoxymethylsilane, and di-tert-pentoxyethylsilane.

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 Feb 12, 2016
From: SPENCE, DANIEL P.; LEI, XINJIAN; PEARLSTEIN, RONALD MARTIN; XIAO, MANCHAO; HO, RICHARD
To: AIR PRODUCTS AND CHEMICALS, INC.
Reel/Frame 037726/0148 →