IP Library Granted Patent US 11,691,993
Granted Patent B2
US 11,691,993 · App. 16/635,452 · Granted Jul 4, 2023

1,1,1-tris(organoamino)disilane compounds and method of preparing same

Inventors: Byung K. Hwang (Wilmington, DE); Xiaobing Zhou (Wilmington, DE)
Assignee: JIANGSU NATA OPTO-ELECTRONIC MATERIALS CO. LTD.
C07F7/025C01B21/068C01B33/126C23C16/345C23C16/402C23C16/45525
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Quick Facts
Patent No.
US 11,691,993
App. No.
16/635,452
Granted
Jul 4, 2023
Kind
B2
Abstract

A 1,1,1-tris(organoamino)disilane compound and a method of preparing the 1,1,1-tris(organoamino)disilane compound are disclosed. The method comprises aminating a 1,1,1-trihalodisilane with an aminating agent comprising an organoamine compound to give a reaction product comprising the 1,1,1-tris(organoamino)disilane compound, thereby preparing the 1,1,1-tris(organoamino)disilane compound. A film-forming composition is also disclosed. The film-forming composition comprises the 1,1,1-tris(organoamino)disilane compound. A film formed with the film-forming composition, and a method of forming the film, are also disclosed. The method of forming the film comprises subjecting the film-forming composition comprising the 1,1,1-tris(organoamino)disilane compound to a deposition condition in the presence of a substrate, thereby forming the film on the substrate.

Claims (31)

1. A 1,1,1-tris(organoamino)disilane compound having the following formula:

wherein: (i) each R 1 and R 2 is —CH 3 , such that the 1,1,1-tris(organoamino)disilane compound is 1,1,1-tris(dimethylamino)disilane; or (ii) each R 1 is H and each R 2 is —CH 2 CH 3 , such that the 1,1,1-tris(organoamino)disilane compound is 1,1,1-tris(ethylamino)disilane.

2. A method of preparing a 1,1,1-tris(organoamino)disilane compound, said method comprising:

aminating a 1,1,1-trihalodisilane with an aminating agent to give a reaction product comprising the 1,1,1-tris(organoamino)disilane compound, thereby preparing the 1,1,1-tris(organoamino)disilane compound;

wherein the aminating agent comprises an organoamine compound having the formula HNR 1 R 2 , wherein each R 1 is an independently selected hydrocarbyl group having from 1 to 10 carbon atoms, and each R 2 is an independently selected hydrocarbyl group having from 1 to 10 carbon atoms or H;

wherein the 1,1,1-tris(organoamino)disilane compound having the following formula:

wherein: (i) each R 1 and R 2 is —CH, such that the 1,1,1-tris(organoamino)disilane compound is 1,1,1-tris(dimethylamino)disilane, or (ii) each R 1 is H and each R 2 is —CH 2 CH 3 , such that the 1,1,1-tris(organoamino)disilane compound is 1,1,1-tris(ethylamino)disilane.

3. The method of claim 2 , further comprising isolating the 1,1,1-tris(organoamino)disilane compound from the reaction product.

4. The method of claim 3 , wherein isolating the 1,1,1-tris(organoamino)disilane compound from the reaction product comprises: (i) filtering the reaction product; (ii) distilling the reaction product; or (iii) both (i) and (ii).

5. The method of any claim 2 , wherein the aminating agent further comprises a halogen scavenging agent other than the organoamine compound.

6. The method of claim 5 , wherein (i) a molar ratio of the 1,1,1-trihalodisilane to the organoamine compound of the aminating agent is from 1:3 to 1:1000; (ii) a molar ratio of the 1,1,1-trihalodisilane to the halogen scavenging agent of the aminating agent is from 1:3 to 1:1000; or (iii) both (i) and (ii).

7. The method of claim 2 , wherein a molar ratio of the 1,1,1-trihalodisilane to the organoamine compound of the aminating agent is from 1:6 to 1:1000.

8. The method of claim 2 , wherein: (i) aminating is carried out in a vehicle; (ii) aminating is carried out at a reduced temperature; (iii) the 1,1,1-trihalodisilane is 1,1,1-trichlorodisilane; or (iv) any combination of (i) to (iii).

9. The method of claim 8 , wherein aminating is carried out in a vehicle, and wherein the vehicle comprises an organic solvent.

10. The method of claim 8 , wherein aminating is carried out at a reduced temperature, and wherein the reduced temperature is less than 0° C.

11. The method of claim 2 , wherein aminating comprises combining the 1,1,1-trihalodisilane and the aminating agent to aminate the 1,1,1-trihalodisilane to give the 1,1,1-tris(organoamino)disilane compound.

12. The method of claim 2 , wherein: (i) the organoamine compound is dimethylamine, and the 1,1,1-tris(organoamino)disilane compound is 1,1,1-tris(dimethylamino)disilane; or (ii) the organoamine compound is ethylamine, and the 1,1,1-tris(organoamino)disilane compound is 1,1,1-tris(ethylamino)disilane.

13. A reaction product comprising a 1,1,1-tris(organoamino)disilane compound, wherein the reaction product comprising the 1,1,1-tris(organoamino)disilane compound is formed by a method comprising:

aminating a 1,1,1-trihalodisilane with an aminating agent to give a reaction product comprising the 1,1,1-tris(organoamino)disilane compound, thereby preparing the 1,1,1-tris(organoamino)disilane compound,

wherein the 1,1,1-tris(organoamino)disilane compound having the following formula:

wherein: (i) each R 1 and R 2 is —CH 3 , such that the 1,1,1-tris(organoamino)disilane compound is 1,1,1-tris(dimethylamino)disilane; or (ii) each R 1 is H and each R 2 is —CH 2 CH 3 , such that the 1,1,1-tris(organoamino)disilane compound is 1,1,1-tris(ethylamino)disilane,

wherein the aminating agent comprises an organoamine compound having the formula HNR 3 R 4 , wherein each R 3 is an independently selected hydrocarbyl group having from 1 to 10 carbon atoms, and each R 4 is an independently selected hydrocarbyl group having from 1 to 10 carbon atoms or H.

14. The reaction product of claim 13 , wherein the reaction product comprises the 1,1,1-tris(organoamino)disilane compound in an amount of at least 70 wt. % based on the total weight of the reaction product.

15. The reaction product of claim 13 , wherein the reaction product has a total content of halogen and/or halide of less than 100 ppm.

16. A film-forming composition, wherein the film-forming composition comprises the 1,1,1-tris(organoamino)disilane compound of claim 1 .

17. A method of forming a film, said method comprising:

subjecting a film-forming composition to a deposition condition in the presence of a substrate, thereby forming the film on the substrate;

wherein the film-forming composition is the film-forming composition of claim 16 .

18. A film formed by a method comprising:

subjecting a film-forming composition to a deposition condition in the presence of a substrate, thereby forming the film on the substrate,

wherein the film-forming composition is the film-forming composition of claim 16 .

Assignments (5)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME PREVIOUSLY RECORDED AT REEL: 056680 FRAME: 0354. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 3, 2021
From: ZHOU, XIAOBING; HWANG, BYUNG K.
To: DOW SILICONES CORPORATION
Reel/Frame 057405/0334 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSINGOR NAME PREVIOUSLY RECORDED ON REEL 056695 FRAME 0754. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 3, 2021
From: DOW SILICONES CORPORATION
To: DDP SPECIALTY ELECTRONIC MATERIALS US 9, LLC
Reel/Frame 057406/0046 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2021
From: ZHOU, XIAOBING; HWANG, BYUNG K.
To: DOW CORNING CORPORATION
Reel/Frame 056680/0354 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2021
From: DOW CORNING CORPORATION
To: DDP SPECIALTY ELECTRONIC MATERIALS US 9, LLC
Reel/Frame 056695/0754 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2021
From: DDP SPECIALTY ELECTRONIC MATERIALS US 9, LLC
To: JIANGSU NATA OPTO-ELECTRONIC MATERIALS CO. LTD.
Reel/Frame 055054/0570 →