IP Library Granted Patent US 12,071,688
Granted Patent B2
US 12,071,688 · App. 17/214,701 · Granted Aug 27, 2024

Precursors and methods for preparing silicon-containing films

Inventors: SangJin Lee (Suwon, KR); DaHye Kim (Suwon, KR); Sungsil Cho (Anyang, KR); Seobong Chang (Suwon, KR); Jae Eon Park (HwaSung, KR); Bryan C. Hendrix (Danbury, CT); Thomas H. Baum (New Fairfield, CT); SooJin Lee (Suwon, KR)
Assignee: ENTEGRIS, INC.
C23C16/45553C07F7/025C07F7/10C23C16/345C23C16/402C23C16/45536C23C16/50H01L21/02219H01L21/02274H01L21/0228H01L21/02164H01L21/0217
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Quick Facts
Patent No.
US 12,071,688
App. No.
17/214,701
Granted
Aug 27, 2024
Kind
B2
Abstract

Provided are certain liquid silicon precursors useful for the deposition of silicon-containing films, such as films comprising silicon, silicon nitride, silicon oxynitride, silicon dioxide, silicon carbide, carbon-doped silicon nitride, or carbon-doped silicon oxynitride. Also provided are methods for forming such films utilizing vapor deposition techniques.

Claims (28)

1. A compound of Formula (I):

wherein each R 1 is independently selected from a group consisting of hydrogen, C 1 -C 4 alkyl, or a halogen atom selected from a group consisting of Cl, Br, and I, and wherein at least one R 1 is other than hydrogen.

2. The compound of claim 1 , wherein each R 1 is methyl.

3. The compound of claim 1 , wherein each R 1 is ethyl.

4. The compound of claim 1 , wherein each R 1 is a halogen atom selected from a group consisting of Cl, Br, and I.

5. A process for preparing a compound of Formula (I):

wherein each R 1 is independently selected from a group consisting of, C 1 -C 4 alkyl, or a halogen atom selected from a group consisting of Cl, Br, and I, wherein at least one R 1 is other than-hydrogen, which comprises the steps:

A. contacting a compound of the formula

with a compound of the formula M-R 3 , wherein M is lithium or potassium and R 3 is a C 1 -C 6 alkyl group, optionally containing a nitrogen atom, to provide a compound of Formula (II):

wherein each R 1 is independently selected from a group consisting of hydrogen, C 1 -C 4 alkyl, or a halide atom selected from a group consisting of Cl, Br, and I, and wherein R 2 is chosen from lithium or potassium; followed by

B. Reacting the compound of Formula (II) with a compound of the formula

wherein X is a halogen.

6. The process of claim 5 , wherein each R 1 is methyl.

7. The process of claim 5 , wherein the compound of the formula M-R 3 is selected from a group consisting of n-butyl lithium, methyl lithium, t-butyl lithium, lithium diisopropylamide, methyl potassium, and n-butyl potassium.

8. The process of claim 5 , wherein each R 1 is methyl, X is chloro, and M is lithium.

9. A method for depositing a silicon-containing film onto a surface of a microelectronic device, which comprises introducing at least one compound of Formula (I)

wherein each R 1 is independently selected from a group consisting of hydrogen, C 1 -C 4 alkyl, or a halogen atom selected from a group consisting of Cl, Br, and I, and wherein at least one R 1 is other than hydrogen,

to said surface in a reaction chamber, under vapor deposition conditions.

10. The method of claim 9 , wherein the silicon-containing film is silicon dioxide.

11. The method of claim 9 , wherein the silicon-containing film is silicon nitride.

12. The method of claim 9 , wherein the vapor deposition conditions are selected from a group consisting of chemical vapor deposition (CVD), atomic layer deposition (ALD), plasma-enhanced ALD (PEALD), plasma enhanced cyclical chemical vapor deposition (PECCVD), a flowable chemical vapor deposition (FCVD), a plasma-enhanced ALD-like process, or an ALD process with oxygen-containing reactants, a nitrogen-containing reactant, or a combination thereof.

13. The method of claim 10 , wherein the vapor deposition conditions comprise a temperature of about 150° C. to about 650° C., and a pulsing sequence comprising the steps:

(v) injection of precursor of Formula (I) for 0.1 to 30 seconds, followed by

(vi) purging for 1 to 30 seconds using an inert gas, followed by

(vii) injection of ozone at a flow rate of 50 to 500 secm, for about 0.1 to 30 seconds, followed by

(viii) purging for 1 to 30 seconds using an inert gas, and repeating steps (i) through (iv) until a film of desired thickness has been obtained.

14. The method of claim 13 , wherein the compound of Formula (I) is bis(dimethylsilyl)dimethylhydrazine.

15. The method of claim 13 , wherein the temperature is about 500 to 550° C.

Assignments (3)
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.; CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: TRUIST BANK, AS NOTES COLLATERAL AGENT
Reel/Frame 060613/0072 →
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.
To: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
Reel/Frame 060614/0980 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2021
From: LEE, SOOJIN; LEE, SANGJIN; KIM, DAHYE; CHO, SUNGSIL; CHANG, SEOBONG; PARK, JAE EON; HENDRIX, BRYAN C.; BAUM, THOMAS H.
To: ENTEGRIS, INC.
Reel/Frame 055742/0183 →
Continuity (2)
Provisional Application 63002855 · Mar 31, 2020
Related Publication 20210301400A1 · Sep 30, 2021