Organometallic compounds

• US 7,547,631 B2
• Filed: 10/04/2006
• Issued: 06/16/2009
• Est. Priority Date: 07/31/2006
• Status: Active Grant

• Current Assignee: Rohm and Haas Electronic Materials LLC (DuPont de Nemours, Inc.)
• Original Assignee: Rohm and Haas Electronic Materials LLC (DuPont de Nemours, Inc.)
• Inventors: Wang, Qing Min, Shenai-Khatkhate, Deodatta Vinayak
• Primary Examiner(s): NAZARIO GONZALEZ, PORFIRIO
• Application Number:
  US11/542,923
• Publication Number:
  US 20080026577A1
• Time in Patent Office: 986 Days
• Field of Search: 556/18, 556/20, 438/680, 438/681, 427/248.1, 106/1.25, 564/15
• US Class Current: 438/680
• CPC Class Codes: C07F 17/02 of metals of Groups 8, 9 or 10 of the Periodic System
• CPC Class Codes: C07F 9/5045 Complexes or chelates of phosphines with metallic compounds or metals
• CPC Class Codes: C23C 16/34 Nitrides C23C16/303 takes precedence
• CPC Class Codes: C23C 16/40 Oxides

Abstract

Organometallic compounds containing a phosphoamidinate ligand are provided. Such compounds are particularly suitable for use as vapor deposition precursors. Also provided are methods of depositing thin films, such as by ALD and CVD, using such compounds.

Claims

1. A method of depositing a film comprising the steps of:

providing a substrate in a vapor deposition reactor;

conveying as a precursor an organometallic compound of the formula (R¹YCR²PR³)_nM^+mL¹_(m-n)L²_p, wherein R¹, R² and R³ are independently chosen from H, (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl and aryl;

Y═

N or P;

M=a metal;

L¹=an anionic ligand;

L²=a neutral ligand;

m=the valence of M;

n=1-6;

p=0-3; and

wherein m>

n in a gaseous form to the reactor; and

depositing a film comprising the metal on the substrate.

2. The method of claim 1 wherein L¹ is chosen from hydride, halide, azide, alkyls, alkenyl, alkynyl, carbonyl, amido, alkylamido, dialkylamido, dialkylamidoalkyl, imido, hydrazido, phosphido, nitrosyl, nitryl, nitrate, nitrile, alkoxy, dialkylaminoalkoxy, alkoxyalkyldialkylamino, siloxy, diketonates, ketoiminates, cyclopentadienyls, silyls, pyrazolates, and amidinates.

3. The method of claim 1 wherein L² is chosen from CO, NO, alkenes, dienes, trienes, alkynes, and aromatic compounds.

4. The method of claim 1 wherein M is chosen from a Group 2 to Group 16 metal.

5. The method of claim 1 wherein the organometallic compound is in a composition further comprising an organic solvent;

and wherein the method further comprises the step of conveying the composition into the reactor using direct liquid injection.

6. A method of depositing a film comprising the steps of:

providing a substrate in a vapor deposition reactor;

conveying as a first precursor an organometallic compound of the formula (R¹YCR²PR³)_nM^+mL¹_(m-n)L²_p, wherein R¹, R² and R³ are independently chosen from H, (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl and aryl;

Y═

N or P;

M=a metal;

L¹=an anionic ligand;

L²=a neutral ligand;

m=the valence of M;

n=1-6;

p=0-3; and

wherein m>

n in a gaseous form to the reactor;

chemisorbing the first precursor compound on the surface of the substrate;

removing any non-chemisorbed first precursor compound from the reactor;

conveying a second precursor in a gaseous form to the reactor;

reacting the first and second precursors to form a film on the substrate; and

removing any unreacted second precursor.

7. The method of claim 6 wherein the second precursor is selected from oxygen, ozone, water, peroxide, alcohols, nitrous oxide and ammonia.

8. The method of claim 6 wherein L¹ is chosen from hydride, halide, azide, alkyls, alkenyl, alkynyl, carbonyl, amido, alkylamido, dialkylamido, dialkylamidoalkyl, imido, hydrazido, phosphido, nitrosyl, nitryl, nitrate, nitrile, alkoxy, dialkylaminoalkoxy, alkoxyalkyldialkylamino, siloxy, diketonates, ketoiminates, cyclopentadienyls, silyls, pyrazolates, and amidinates.

9. The method of claim 6 wherein L² is chosen from CO, NO, alkenes, dienes, trienes, alkynes, and aromatic compounds.

10. The method of claim 6 wherein M is chosen from a Group 2 to Group 16 metal.

11. A method for preparing phosphoamidine compounds comprising reacting a nitrile compound with a primary phosphine in the presence of a metal trifluoromethanesulfonate catalyst.

12. The method of claim 11 further comprising reacting a primary amine with the nitrile compound and the primary phosphine.