# US 10,501,484 B2 · Amine substituted trisilylamine and tridisilylamine compounds and synthesis methods thereof

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- Number: US 10,501,484 B2
- Document ID: US10501484B2
- Status: Granted
- Kind: B2
- Application number: 15/892,839
- Filed: 2018-02-09
- Published: 2018-06-14
- Granted: 2019-12-10
- Earliest claimed: 2013-09-27
- Assignees: L'Air Liquide, Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges Claude
- Applicants: L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude
- Inventors: Antonio Sanchez; Jean-Marc Girard; Gennadiy Itov; Manish Khandelwal; Matthew Damien Stephens; Peng Zhang
- Web page: https://patentgrep.com/patent/US10501484B2

## CPC

- C07F 7/025: {without C-silicon linkages}
- C07F 7/10: containing nitrogen {having a Si-N linkage}
- H10P 14/20: of semiconductor materials
- H10P 14/6687: {the compound comprising silicon and nitrogen}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

Halogen free amine substituted trisilylamine and tridisilylamine compounds and a method of their preparation via dehydrogenative coupling between the corresponding unsubstituted trisilylames and amines catalyzed by transition metal catalysts is described. This new approach is based on the catalytic dehydrocoupling of a Si—H and a N—H moiety to form an Si—N containing compound and hydrogen gas. The process can be catalyzed by transition metal heterogenous catalysts such as Ru(0) on carbon, Pd(0) on MgO) as well as transition metal organometallic complexes that act as homogeneous catalysts. The —Si—N containing products are halide free. Such compounds can be useful for the deposition of thin films by chemical vapor deposition or atomic layer deposition of Si containing films.

## Claims

### Claim 1

A halogen free composition comprising a precursor having the formula:
wherein R1 and R2 are independently selected from H or a linear or branched C1 to C6 alkyl; and R3, R4, and R5 are H, provided that R2 cannot be methyl or ethyl when R1 is H and R2 cannot be ethyl when R1 is ethyl.

### Claim 2 (depends on 1)

The halogen free composition of claim 1, wherein R1 and R2 are independently selected from the group consisting of H, methyl (Me), ethyl (Et), iso-propyl (iPr), and t-butyl (tBu).

### Claim 3 (depends on 2)

The halogen free composition of claim 2, wherein R1 is H.

### Claim 4 (depends on 3)

The halogen free composition of claim 3, wherein R2 is iPr.

### Claim 5 (depends on 3)

The halogen free composition of claim 3, wherein R2 is tBu.

### Claim 6 (depends on 5)

The halogen free composition of claim 5, the halogen free product comprising less than 3 ppm halogen.

### Claim 7 (depends on 2)

The halogen free composition of claim 2, wherein R1 is Me.

### Claim 8 (depends on 7)

The halogen free composition of claim 7, wherein R2 is Me.

### Claim 9 (depends on 7)

The halogen free composition of claim 7, wherein R2 is Et.

### Claim 10 (depends on 7)

The halogen free composition of claim 7, wherein R2 is iPr.

### Claim 11 (depends on 7)

The halogen free composition of claim 7, wherein R2 is tBu.

### Claim 12 (depends on 2)

The halogen free composition of claim 2, wherein R1 is Et.

### Claim 13 (depends on 12)

The halogen free composition of claim 12, wherein R2 is iPr.

### Claim 14 (depends on 12)

The halogen free composition of claim 12, wherein R2 is tBu.

### Claim 15 (depends on 2)

The halogen free composition of claim 2, wherein R1 is iPr.

### Claim 16 (depends on 15)

The halogen free composition of claim 15, wherein R2 is iPr.

### Claim 17 (depends on 16)

The halogen free composition of claim 16, the halogen free product comprising less than 3 ppm halogen.

### Claim 18 (depends on 15)

The halogen free composition of claim 15, wherein R2 is tBu.

### Claim 19 (depends on 2)

The halogen free composition of claim 2, the halogen free product comprising less than 3 ppm halogen.

### Claim 20 (depends on 1)

The halogen free composition of claim 1, the halogen free composition comprising less than 3 ppm halogen.