IP Library › Granted Patent US 11,912,730
Granted Patent B2
US 11,912,730 · App. 18/066,903 · Granted Feb 27, 2024

Organoamino-functionalized cyclic oligosiloxanes for deposition of silicon-containing films

Inventors: Matthew R. MacDonald (Laguna Niguel, CA); John F. Lehmann (Schnecksville, PA)
Assignee: Versum Materials US, LLC
C07F7/0816C23C16/402C23C16/45553C23C16/52C23C16/45504
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Quick Facts
Patent No.
US 11,912,730
App. No.
18/066,903
Granted
Feb 27, 2024
Kind
B2
Abstract

Amino-functionalized cyclic oligosiloxanes, which have at least three silicon and three oxygen atoms as well as at least one organoamino group and methods for making the oligosiloxanes are disclosed. Methods for depositing silicon and oxygen containing films using the organoamino-functionalized cyclic oligosiloxanes are also disclosed.

Claims (13)

1. A method for depositing a film comprising silicon and oxygen onto a substrate, the method comprising the steps of:

a) providing a substrate in a reactor;

b) introducing into the reactor at least one silicon precursor compound selected from the group consisting of Formulae A-D

wherein R 1 is selected from the group consisting of a linear C 1 to C 10 alkyl group, a branched C 3 to C 10 alkyl group, a C 3 to C 10 cyclic alkyl group, a C 3 to C 10 heterocyclic group, a C 3 to C 10 alkenyl group, a C 3 to C 10 alkynyl group, and a C 4 to C 10 aryl group; R 2 is selected from the group consisting of hydrogen, a C 1 to C 10 linear alkyl group, a branched C 3 to C 10 alkyl group, a C 3 to C 10 cyclic alkyl group, a C 3 to C 10 heterocyclic group, a C 3 to C 10 alkenyl group, a C 3 to C 10 alkynyl group, and a C 4 to C 10 aryl group, wherein R 1 and R 2 are either linked to form a cyclic ring structure or are not linked to form a cyclic ring structure; R 3-11 are each independently selected from the group consisting of hydrogen, a linear C 1 to C 10 alkyl group, a branched C 3 to C 10 alkyl group, a C 3 to C 10 cyclic alkyl group, a C 2 to C 10 alkenyl group, a C 2 to C 10 alkynyl group, a C 4 to C 10 aryl group, and an organoamino group, NR 1 R 2 , wherein R 1 and R 2 are defined above; n=1, 2, or 3, and m=2 or 3;

c) purging the reactor with a purge gas;

d) introducing at least one of an oxygen-containing source and a nitrogen-containing source into the reactor; and

e) purging the reactor with the purge gas,

wherein the steps b through e are repeated until a desired thickness of film is deposited;

and wherein the method is conducted at one or more temperatures ranging from about 25° C. to 600° C.

2. The method of claim 1 wherein each of R 3-9 is independently selected from the group consisting of hydrogen and a C 1 to C 4 alkyl group.

3. The method of claim 1 , wherein R 1 is selected from the group consisting of a C 3 to C 10 cyclic alkyl group and a C 4 to C 10 aryl group.

4. The method of claim 1 , wherein the at least one silicon precursor compound is selected from the group consisting of 2,4-bis(dimethylamino)-2,4,6-trimethylcyclotrisiloxane, 2,4-bis(dimethylamino)-2,4,6,6-tetramethylcyclotrisiloxane, 2,4-bis(dimethylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4-bis(dimethylamino)-2,4,6,6,8,8-hexamethylcyclotetrasiloxane, 2,6-bis(dimethylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,6-bis(dimethylamino)-2,4,4,6,8,8-hexamethylcyclotetrasiloxane, 2-dimethylamino-2,4,6,8,10-pentamethylcyclopentasiloxane, 2-dimethylamino-2,4,4,6,6,8,8,10,10-nonamethylcyclopentasiloxane, 2,4-bis(methylamino)-2,4,6-trimethylcyclotrisiloxane, 2,4-bis(methylamino)-2,4,6,6-tetramethylcyclotrisiloxane, 2,4-bis(methylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4-bis(methylamino)-2,4,6,6,8,8-hexamethylcyclotetrasiloxane, 2,6-bis(methylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,6-bis(methylamino)-2,4,4,6,8,8-hexamethylcyclotetrasiloxane, 2-methylamino-2,4,6,8,10-pentamethylcyclopentasiloxane 2-methylamino-2,4,4,6,6,8,8,10,10-nonamethylcyclopentasiloxane, 2,4-bis(iso-propylamino)-2,4,6-trimethylcyclotrisiloxane, 2,4-bis(iso-propylamino)-2,4,6,6-tetramethylcyclotrisiloxane, 2,4-bis(iso-propylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4-bis(iso-propylamino)-2,4,6,6,8,8-hexamethylcyclotetrasiloxane, 2,6-bis(iso-propylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,6-bis(iso-propylamino)-2,4,4,6,8,8-hexamethylcyclotetrasiloxane, 2-iso-propylamino-2,4,6,8,10-pentamethylcyclopentasiloxane, 2-iso-propylamino-2,4,4,6,6,8,8,10,10-nonamethylcyclopentasiloxane, 2,4-bis(N-ethylmethylamino)-2,4,6-trimethylcyclotrisiloxane, 2,4-bis(N-ethylmethylamino)-2,4,6,6-tetramethylcyclotrisiloxane, 2,4-bis(N-ethylmethylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4-bis(N-ethylmethylamino)-2,4,6,6,8,8-hexamethylcyclotetrasiloxane, 2,6-bis(N-ethylmethylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,6-bis(N-ethylmethylamino)-2,4,4,6,8,8-hexamethylcyclotetrasiloxane, 2-(N-ethylmethylamino)-2,4,6,8,10-pentamethylcyclopentasiloxane, 2-(N-ethylmethylamino)-2,4,4,6,6,8,8,10,10-nonamethylcyclopentasiloxane, 2,4-bis(diethylamino)-2,4,6-trimethylcyclotrisiloxane, 2,4-bis(diethylamino)-2,4,6,6-tetramethylcyclotrisiloxane, 2,4-bis(diethylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4-bis(diethylamino)-2,4,6,6,8,8-hexamethylcyclotetrasiloxane, 2,6-bis(diethylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,6-bis(diethylamino)-2,4,4,6,8,8-hexamethylcyclotetrasiloxane, 2-diethylamino-2,4,6,8,10-pentamethylcyclopentasiloxane, 2-diethylamino-2,4,4,6,6,8,8,10,10-nonamethylcyclopentasiloxane, 2,4,6-tris(dimethylamino)-2,4,6-trimethylcyclotrisiloxane, 2,4,6,8-tetrakis(dimethylamino)-2,4,6,8-tetramethylcyclotetrasiloxane, 2,4,6-tris(methylamino)-2,4,6-trimethylcyclotrisiloxane, 2,4,6,8-tetrakis(methylamino)-2,4,6,8-tetramethylcyclotetrasiloxane.

5. The method of claim 1 wherein the silicon precursor compound further comprising at least one selected from the group consisting of a solvent and an inert gas.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2023
From: MACDONALD, MATTHEW R.; LEHMANN, JOHN F.
To: VERSUM PATENTS US, LLC
Reel/Frame 064041/0293 →
Continuity (4)
Division 17030187 · Sep 23, 2020
Continuation In Part 16838997 · Apr 2, 2020
Provisional Application 62829851 · Apr 5, 2019
Related Publication 20230138138A1 · May 4, 2023
Cited By (1)
US 12,534,579