IP Library Granted Patent US 9,079,923
Granted Patent B2
US 9,079,923 · App. 13/187,833 · Granted Jul 14, 2015

Multidentate ketoimine ligands for metal complexes

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Quick Facts
Patent No.
US 9,079,923
App. No.
13/187,833
Granted
Jul 14, 2015
Kind
B2
Abstract

The present invention is a plurality of metal-containing complexes of a multidentate ketoiminate.

Claims (24)

1. A compound having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5-6 are individually selected from the group consisting of C 1-2 alkyl; L is a neutral ligand coordinated to the metal via an oxygen or nitrogen atom; n is 0 or 1; X and Z are independently selected from O or N; when X is N, m is 2 and the two R 5 are each independently selected from the group consisting of C 1-2 alkyl; when X is O, m is 1 and R 5 is selected from the group consisting of C 1-2 alkyl; q can be 0 or 1; when q is 0, Z and R 6 are not present; when q is 1, Z is either N, p is 2 and the two R 6 are each independently selected from the group consisting of C 1-2 alkyl; or Z is O, p is 1 and R 6 is selected from the group consisting of C 1-2 alkyl; when q is 0, n must be 1; when X is N and Z is O and q is 1, n must be 1.

2. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5-6 are individually selected from the group consisting of C 1-2 alkyl; L is a neutral ligand coordinated to the metal via an oxygen or nitrogen atom.

3. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, and a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5 is selected from the group consisting of C 1-2 alkyl; L is a neutral ligand coordinated to the metal via an oxygen or nitrogen atom.

4. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, and a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5-6 are individually selected from the group consisting of C 1-2 alkyl, R is selected from the group consisting of C 1-2 alkyl; L is a neutral ligand coordinated to the metal via an oxygen or nitrogen atom.

5. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, and a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5-6 are individually selected from the group consisting of C 1-2 alkyl, R and R are individually selected from the group consisting of C 1-2 alkyl.

6. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, and a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5 is selected from the group consisting of C 1-2 alkyl, R is selected from the group consisting of C 1-2 alkyl.

7. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, and a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5 is selected from the group consisting of C 1-2 alkyl, R and R are individually selected from the group consisting of C 1-2 alkyl.

8. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, and a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5-6 are individually selected from the group consisting of C 1-2 alkyl, R and R are individually selected from the group consisting of C 1-2 alkyl; L is a neutral ligand coordinated to the metal via an oxygen or nitrogen atom.

9. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, and a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5 is selected from the group consisting of C 1-2 alkyl, R is selected from the group consisting of C 1-2 alkyl; L is a neutral ligand coordinated to the metal via an oxygen or nitrogen atom.

10. The compound of claim 1 having the formula:

wherein M is selected from the group consisting of magnesium, calcium, strontium, and barium; wherein R 1 is selected from the group consisting of branched alkyl, fluoroalkyl, cycloaliphatic, and a C 6 aryl and a C 10 aryl; R 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloaliphatic, and aryl; R 3 is linear or branched selected from the group consisting of alkyl, fluoroalkyl, cycloaliphatic, and aryl; R 4 is a linear or branched alkyl bridge having 2 to 10 carbon atoms; R 5 is selected from the group consisting of C 1-2 alkyl, R and R are individually selected from the group consisting of C 1-2 alkyl; L is a neutral ligand coordinated to the metal via an oxygen or nitrogen atom.

11. The compound of claim 1 wherein the neutral ligand is selected from the group consisting of ether, amines, organic amides, and ketones.

12. A composition comprising the compound of claim 1 dissolved in a solvent selected from the group consisting of glyme solvents having from 1 to 20 ethoxy —(C 2 H 4 O)— repeat units; C 2 -C 12 alkanols, organic ethers selected from the group consisting of dialkyl ethers comprising C 1 -C 6 alkyl moieties, C 4 -C 8 cyclic ethers; C 12 -C 60 crown O 4 -O 20 ethers wherein the prefixed C i range is the number i of carbon atoms in the ether compound and the suffixed O i range is the number i of oxygen atoms in the ether compound; C 6 -C 12 aliphatic hydrocarbons; C 6 -C 18 aromatic hydrocarbons; organic esters; organic amines; polyamines and organic amides.

13. A vapor deposition process for forming a conformal metal oxide thin film on a substrate, wherein the metal is selected from the group consisting of magnesium, calcium, strontium and barium the process comprising: introducing a precursor source and an oxygen containing agent into a deposition chamber to deposit the metal oxide film on the substrate, the improvement which comprises using the compound of claim 1 as said precursor source.

14. A vapor deposition process for forming a conformal metal oxide thin film on a substrate, wherein the metal is selected from the group consisting of magnesium, calcium, strontium and barium the process comprising: introducing a precursor source and an oxygen containing agent into a deposition chamber to deposit the metal oxide film on the substrate, the improvement which comprises using the composition of claim 12 as said precursor source.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Oct 7, 2019
From: CITIBANK, N.A., AS AGENT
To: VERSUM MATERIALS US, LLC
Reel/Frame 050647/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 20, 2017
From: AIR PRODUCTS AND CHEMICALS, INC.
To: VERSUM MATERIALS US, LLC
Reel/Frame 041772/0733 →
PATENT SECURITY AGREEMENT Recorded Oct 27, 2016
From: VERSUM MATERIALS US, LLC
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 040503/0442 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2011
From: LEI, XINJIAN; SPENCE, DANIEL P.
To: AIR PRODUCTS AND CHEMICALS, INC.
Reel/Frame 027099/0989 →