IP Library Granted Patent US 7,034,169
Granted Patent B1
US 7,034,169 · App. 11/111,455 · Granted Apr 25, 2006

Volatile metal β-ketoiminate complexes

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Quick Facts
Patent No.
US 7,034,169
App. No.
11/111,455
Granted
Apr 25, 2006
Kind
B1
Abstract

Metal complexes, containing copper, silver, gold, cobalt, ruthenium, rhodium, platinum, palladium, nickel, osmium, and/or indium, and methods for making and using same are described herein. In certain embodiments, the metal complexes described herein may be used as precursors to deposit metal or metal-containing films on a substrate through, for example, atomic layer deposition or chemical vapor deposition conditions.

Claims (40)

1. A complex represented by formula (I) or (II):

wherein M is a metal selected from Cu, Au, Ag, Co, Ru, Rh, Pt, In, Pd, Ni, Os, and mixtures thereof;

wherein R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom; an alkyl having a formula C n H 2n+1 wherein n is a number ranging from 1 to 20; a fluoroalkyl having a formula C n H x F y wherein the product of (x+y) equals the product of (2n+1) and n is a number ranging from 1 to 20; an alkylsilane having a formula (R 5 ) 3 Si wherein R 5 is each independently an alkyl, a fluoralkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms; an aryl comprising from 6 to 18 carbon atoms; an alkyl-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroalkyl-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroaryl comprising from 6 to 18 carbon atoms; an alkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; a fluoroalkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; an ether having a formula (CH 2 ) n O(C m H 2m+1 ) where n is a number ranging from 1 to 20 and m is a number ranging from 1 to 20; an alkoxy comprising from 1 to 20 carbon atoms; an amide group comprising from 1 to 20 carbon atoms; a halogen atom; and a nitro group NO 2 ;

wherein L is a ligand selected from carbon monoxide; an alkylnitrile comprising from 2 to 20 carbon atoms; a silylnitrile having a formula (R 6 ) 3 SiCN wherein R 6 is each independently an alkyl comprising from 1 to 20 carbon atoms; an alkyne comprising from 1 to 20 carbon atoms; a silylalkyne having a formula (R 7 ) 3 SiCCR 8 wherein R 7 is each independently an alkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms and R 8 is each independently a hydrogen atom, an alkoxy, or an alkyl comprising from 1 to 20 carbon atoms; a bis(silyl)alkyne having a formula (R 9 ) 3 SiCCSi(R 9 ) 3 wherein R 9 is each independently an alkyl, an amide or an alkoxy comprising from 1 to 20 carbon atoms; an alkene comprising from 1 to 20 carbon atoms; a diene comprising from 1 to 20 carbon atoms; a triene comprising from 1 to 20 carbon atoms; a silylalkene having a formula (R 10 ) 3 SiC(R 17 )C(R 17 ) 2 wherein R 10 is each independently an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; a bis(silyl)alkene having a formula (R 11 ) 3 SiCR 17 CR 17 Si(R 11 ) 3 wherein R 11 is each independently an alkyl comprising from 1 to 20 carbon atoms, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; an allene comprising from 3 to 20 carbon atoms; a allene having a formula (R 12 ) 2 CCC(R 12 ) 2 where R 12 is each independently a hydrogen atom, an alkyl, an alkyl silane, an alkoxysilane, or an amidosilane having a formula (R 13 ) 3 Si wherein R 13 is each independently an alkyl, alkoxy, or an amide comprising from 1 to 20 carbon atoms; an alkylisocyanide comprising from 1 to 20 carbon atoms; a silylisocyanide having a formula (R 14 ) 3 SiNC wherein R 14 is each independently an alkyl comprising from 1 to 20 carbon atoms; an allyl comprising from 1 to 20 carbon atoms; an allylsilane having a formula (R 15 ) 3 SiC(R 17 ) 2 R 17 C(R 17 ) 2 where R 15 is an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and a bis(silyl)allyl having a formula (R 16 ) 3 SiC(R 17 ) 2 CR 17 CR 17 Si(R 16 ) 3 where R 16 comprises from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and

wherein an organometallic bond between M and L is selected from 2 single bonds and 1 single bond.

2. The complex of claim 1 wherein M is Cu.

3. The complex of claim 1 wherein at least one of substituents R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 connect to form a cyclic structure.

4. The complex of claim 3 wherein substituents R 3 and R 4 connect to form a cyclic structure.

5. The complex of claim 3 wherein substituents R 1 and R 2 connect to form a cyclic structure.

6. The complex of claim 1 having formula (I).

7. The complex of claim 1 having formula (II).

8. The complex of claim 7 wherein the two M atoms are the same.

9. The complex of claim 7 wherein the two M atoms are different.

10. A method for depositing a film comprising metal on a substrate, the method comprising:

contacting the substrate with a metal complex having formula (I) or (II) wherein the contacting is conducted at conditions sufficient for the complex to react and form the film

wherein M is a metal selected from Cu, Au, Ag, Co, Ru, Rh, Pt, In, Pd, Ni, Os, and mixtures thereof;

wherein R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom; an alkyl having a formula C n H 2n+1 wherein n is a number ranging from 1 to 20; a fluoroalkyl having a formula C n H x F y wherein the product of (x+y) equals the product of (2n+1) and n is a number ranging from 1 to 20; an alkylsilane having a formula (R 5 ) 3 Si wherein R 5 is each independently an alkyl, a fluoralkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms; an aryl comprising from 6 to 18 carbon atoms; an alkyl-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroalky-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroaryl comprising from 6 to 18 carbon atoms; an alkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; a fluoroalkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; an ether having a formula (CH 2 ) n O(C m H 2m+1 ) where n is a number ranging from 1 to 20 and m is a number ranging from 1 to 20; an alkoxy comprising from 1 to 20 carbon atoms; an amide group comprising from 1 to 20 carbon atoms; a halogen atom; and a nitro group NO 2 ;

wherein L is a ligand selected from carbon monoxide; an alkylnitrile comprising from 2 to 20 carbon atoms; a silylnitrile having a formula (R 6 ) 3 SiCN wherein R 6 is each independently an alkyl comprising from 1 to 20 carbon atoms; an alkyne comprising from 1 to 20 carbon atoms; a silylalkyne having a formula (R 7 ) 3 SiCCR 8 wherein R 7 is each independently an alkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms and R 8 is each independently a hydrogen atom, an alkoxy, or an alkyl comprising from 1 to 20 carbon atoms; a bis(silyl)alkyne having a formula (R 9 ) 3 SiCCSi(R 9 ) 3 wherein R 9 is each independently an alkyl, an amide or an alkoxy comprising from 1 to 20 carbon atoms; an alkene comprising from 1 to 20 carbon atoms; a diene comprising from 1 to 20 carbon atoms; a triene comprising from 1 to 20 carbon atoms; a silylalkene having a formula (R 10 ) 3 SiC(R 17 )C(R 17 ) 2 wherein R 10 is each independently an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; a bis(silyl)alkene having a formula (R 11 ) 3 SiCR 17 CR 17 Si(R 11 ) 3 wherein R 11 is each independently an alkyl comprising from 1 to 20 carbon atoms, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; an allene comprising from 3 to 20 carbon atoms; a allene having a formula (R 12 ) 2 CCC(R 12 ) 2 where R 12 is each independently a hydrogen atom, an alkyl, an alkyl silane, an alkoxysilane, or an amidosilane having a formula (R 13 ) 3 Si wherein R 13 is each independently an alkyl, alkoxy, or an amide comprising from 1 to 20 carbon atoms; an alkylisocyanide comprising from 1 to 20 carbon atoms; a silylisocyanide having a formula (R 14 ) 3 SiNC wherein R 14 is each independently an alkyl comprising from 1 to 20 carbon atoms; an allyl comprising from 1 to 20 carbon atoms; an allylsilane having a formula (R 15 ) 3 SiC(R 17 ) 2 R 17 C(R 17 ) 2 where R 15 is an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and a bis(silyl)allyl having a formula (R 16 ) 3 SiC(R 17 ) 2 CR 17 CR 17 Si(R 16 ) 3 where R 16 comprises from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and

wherein an organometallic bond between M and L is selected from 2 single bonds and 1 single bond.

11. An electronic device comprising a film comprising metal wherein the film is deposited from a precursor mixture comprising at least one complex having formula (I) or (II):

wherein M is a metal selected from Cu, Au, Ag, Co, Ru, Rh, Pt, In, Pd, Ni, Os, and mixtures thereof;

wherein R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom; an alkyl having a formula C n H 2n+1 wherein n is a number ranging from 1 to 20; a fluoroalkyl having a formula C n H x F y wherein the product of (x+y) equals the product of (2n+1) and n is a number ranging from 1 to 20; an alkylsilane having a formula (R 5 ) 3 Si wherein R 5 is each independently an alkyl, a fluoralkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms; an aryl comprising from 6 to 18 carbon atoms; an alkyl-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroalky-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroaryl comprising from 6 to 18 carbon atoms; an alkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; a fluoroalkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; an ether having a formula (CH 2 ) n O(C m H 2m+1 ) where n is a number ranging from 1 to 20 and m is a number ranging from 1 to 20; an alkoxy comprising from 1 to 20 carbon atoms; an amide group comprising from 1 to 20 carbon atoms; a halogen atom; and a nitro group NO 2 ;

wherein L is a ligand selected from carbon monoxide; an alkylnitrile comprising from 2 to 20 carbon atoms; a silylnitrile having a formula (R 6 ) 3 SiCN wherein R 6 is each independently an alkyl comprising from 1 to 20 carbon atoms; an alkyne comprising from 1 to 20 carbon atoms; a silylalkyne having a formula (R 7 ) 3 SiCCR 8 wherein R 7 is each independently an alkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms and R 8 is each independently a hydrogen atom, an alkoxy, or an alkyl comprising from 1 to 20 carbon atoms; a bis(silyl)alkyne having a formula (R 9 ) 3 SiCCSi(R 9 ) 3 wherein R 9 is each independently an alkyl, an amide or an alkoxy comprising from 1 to 20 carbon atoms; an alkene comprising from 1 to 20 carbon atoms; a diene comprising from 1 to 20 carbon atoms; a triene comprising from 1 to 20 carbon atoms; a silylalkene having a formula (R 10 ) 3 SiC(R 17 )C(R 17 ) 2 wherein R 10 is each independently an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; a bis(silyl)alkene having a formula (R 11 ) 3 SiCR 17 CR 17 Si(R 11 ) 3 wherein R 11 is each independently an alkyl comprising from 1 to 20 carbon atoms, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; an allene comprising from 3 to 20 carbon atoms; an allene having a formula (R 12 ) 2 CCC(R 12 ) 2 where R 12 is each independently a hydrogen atom, an alkyl, an alkyl silane, an alkoxysilane, or an amidosilane having a formula (R 13 ) 3 Si wherein R 13 is each independently an alkyl, alkoxy, or an amide comprising from 1 to 20 carbon atoms; an alkylisocyanide comprising from 1 to 20 carbon atoms; a silylisocyanide having a formula (R 14 ) 3 SiNC wherein R 14 is each independently an alkyl comprising from 1 to 20 carbon atoms; an allyl comprising from 1 to 20 carbon atoms; an allylsilane having a formula (R 15 ) 3 SiC(R 17 ) 2 R 17 C(R 17 ) 2 where R 15 is an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and a bis(silyl)allyl having a formula (R 16 ) 3 SiC(R 17 ) 2 CR 17 CR 17 Si(R 16 ) 3 where R 16 comprises from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and

wherein an organometallic bond between the M and L is selected from 2 single bonds and 1 single bond.

12. A method of making a metal complex having a formula (I) or (II):

wherein M is a metal selected from Cu, Au, Ag, Co, Ru, Rh, Pt, In, Pd, Ni, Os, and mixtures thereof;

wherein R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom; an alkyl having a formula C n H 2n+1 wherein n is a number ranging from 1 to 20; a fluoroalkyl having a formula C n H x F y wherein the product of (x+y) equals the product of (2n+1) and n is a number ranging from 1 to 20; an alkylsilane having a formula (R 5 ) 3 Si wherein R 5 is each independently an alkyl, a fluoralkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms; an aryl comprising from 6 to 18 carbon atoms; an alkyl-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroalky-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroaryl comprising from 6 to 18 carbon atoms; an alkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; a fluoroalkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; an ether having a formula (CH 2 ) n O(C m H 2m+1 ) where n is a number ranging from 1 to 20 and m is a number ranging from 1 to 20; an alkoxy comprising from 1 to 20 carbon atoms; an amide group comprising from 1 to 20 carbon atoms; a halogen atom; and a nitro group NO 2 ;

wherein L is a ligand selected from carbon monoxide; an alkylnitrile comprising from 2 to 20 carbon atoms; a silylnitrile having a formula (R 6 ) 3 SiCN wherein R 6 is each independently an alkyl comprising from 1 to 20 carbon atoms; an alkyne comprising from 1 to 20 carbon atoms; a silylalkyne having a formula (R 7 ) 3 SiCCR 8 wherein R 7 is each independently an alkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms and R 8 is each independently a hydrogen atom, an alkoxy, or an alkyl comprising from 1 to 20 carbon atoms; a bis(silyl)alkyne having a formula (R 9 ) 3 SiCCSi(R 9 ) 3 wherein R 9 is each independently an alkyl, an amide or an alkoxy comprising from 1 to 20 carbon atoms; an alkene comprising from 1 to 20 carbon atoms; a diene comprising from 1 to 20 carbon atoms; a triene comprising from 1 to 20 carbon atoms; a silylalkene having a formula (R 10 ) 3 SiC(R 17 )C(R 17 ) 2 wherein R 10 is each independently an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; a bis(silyl)alkene having a formula (R 11 ) 3 SiCR 17 CR 17 Si(R 11 ) 3 wherein R 11 is each independently an alkyl comprising from 1 to 20 carbon atoms, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; an allene comprising from 3 to 20 carbon atoms; a allene having a formula (R 12 ) 2 CCC(R 12 ) 2 where R 12 is each independently a hydrogen atom, an alkyl, an alkyl silane, an alkoxysilane, or an amidosilane having a formula (R 13 ) 3 Si wherein R 13 is each independently an alkyl, alkoxy, or an amide comprising from 1 to 20 carbon atoms; an alkylisocyanide comprising from 1 to 20 carbon atoms; a silylisocyanide having a formula (R 14 ) 3 SiNC wherein R 14 is each independently an alkyl comprising from 1 to 20 carbon atoms; an allyl comprising from 1 to 20 carbon atoms; an allylsilane having a formula (R 15 ) 3 SiC(R 17 ) 2 R 17 C(R 17 ) 2 where R 15 is an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and a bis(silyl)allyl having a formula (R 16 ) 3 SiC(R 17 ) 2 CR 17 CR 17 Si(R 16 ) 3 where R 16 comprises from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and

wherein an organometallic bond between M and L is selected from 2 single bonds and 1 single bond, the method comprising:

reacting a primary amine with a β-diketone compound to form a β-ketoimine intermediate product; and

deprotonating the β-ketoimine intermediate product using a base in the presence of a metal source and ligand (L) to form the copper complex having the formula (I) or (II).

13. Cu(I)(MeC(O)CHC(NMe)Me)(trimethylvinylsilane).

14. A complex represented by a following formula:

wherein R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom; an alkyl having a formula C n H 2n+1 wherein n is a number ranging from 1 to 20; a fluoroalkyl having a formula C n H x F y wherein the product of (x+y) equals the product of (2n+1) and n is a number ranging from 1 to 20; an alkylsilane having a formula (R 5 ) 3 Si wherein R 5 is each independently an alkyl, a fluoralkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms; an aryl comprising from 6 to 18 carbon atoms; an alkyl-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroalky-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroaryl comprising from 6 to 18 carbon atoms; an alkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; a fluoroalkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; an ether having a formula (CH 2 ) n O(C m H 2m+1 ) where n is a number ranging from 1 to 20 and m is a number ranging from 1 to 20; an alkoxy comprising from 1 to 20 carbon atoms; an amide group comprising from 1 to 20 carbon atoms; a halogen atom; and a nitro group NO 2 ;

wherein L is a ligand selected from carbon monoxide; an alkylnitrile comprising from 2 to 20 carbon atoms; a silylnitrile having a formula (R 6 ) 3 SiCN wherein R 6 is each independently an alkyl comprising from 1 to 20 carbon atoms; an alkyne comprising from 1 to 20 carbon atoms; a silylalkyne having a formula (R 7 ) 3 SiCCR 8 wherein R 7 is each independently an alkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms and R 8 is each independently a hydrogen atom, an alkoxy, or an alkyl comprising from 1 to 20 carbon atoms; a bis(silyl)alkyne having a formula (R 9 ) 3 SiCCSi(R 9 ) 3 wherein R 9 is each independently an alkyl, an amide or an alkoxy comprising from 1 to 20 carbon atoms; an alkene comprising from 1 to 20 carbon atoms; a diene comprising from 1 to 20 carbon atoms; a triene comprising from 1 to 20 carbon atoms; a silylalkene having a formula (R 10 ) 3 SiC(R 17 )C(R 17 ) 2 wherein R 10 is each independently an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; a bis(silyl)alkene having a formula (R 11 ) 3 SiCR 17 CR 17 Si(R 11 ) 3 wherein R 11 is each independently an alkyl comprising from 1 to 20 carbon atoms, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; an allene comprising from 3 to 20 carbon atoms; an allene having a formula (R 12 ) 2 CCC(R 12 ) 2 where R 12 is each independently a hydrogen atom, an alkyl, an alkyl silane, an alkoxysilane, or an amidosilane having a formula (R 13 ) 3 Si wherein R 13 is each independently an alkyl, alkoxy, or an amide comprising from 1 to 20 carbon atoms; an alkylisocyanide comprising from 1 to 20 carbon atoms; a silylisocyanide having a formula (R 14 ) 3 SiNC wherein R 14 is each independently an alkyl comprising from 1 to 20 carbon atoms; an allyl comprising from 1 to 20 carbon atoms; an allylsilane having a formula (R 15 ) 3 SiC(R 17 ) 2 R 17 C(R 17 ) 2 where R 15 is an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and a bis(silyl)allyl having a formula (R 16 ) 3 SiC(R 17 ) 2 CR 17 CR 17 Si(R 16 ) 3 where R 16 comprises from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and

wherein an organometallic bond between M and L is selected from 2 single bonds and 1 single bond.

15. A complex represented by a following formula:

wherein R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom; an alkyl having a formula C n H 2n+1 wherein n is a number ranging from 1 to 20; a fluoroalkyl having a formula C n H x F y wherein the product of (x+y) equals the product of (2n+1) and n is a number ranging from 1 to 20; an alkylsilane having a formula (R 5 ) 3 Si wherein R 5 is each independently an alkyl, a fluoralkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms; an aryl comprising from 6 to 18 carbon atoms; an alkyl-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroalky-substituted aryl comprising from 6 to 18 carbon atoms; a fluoroaryl comprising from 6 to 18 carbon atoms; an alkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; a fluoroalkyl-substituted fluoroaryl comprising from 6 to 18 carbon atoms; an ether having a formula (CH 2 ) n O(C m H 2m+1 ) where n is a number ranging from 1 to 20 and m is a number ranging from 1 to 20; an alkoxy comprising from 1 to 20 carbon atoms; an amide group comprising from 1 to 20 carbon atoms; a halogen atom; and a nitro group NO 2 ;

wherein L is a ligand selected from carbon monoxide; an alkylnitrile comprising from 2 to 20 carbon atoms; a silylnitrile having a formula (R 6 ) 3 SiCN wherein R 6 is each independently an alkyl comprising from 1 to 20 carbon atoms; an alkyne comprising from 1 to 20 carbon atoms; a silylalkyne having a formula (R 7 ) 3 SiCCR 8 wherein R 7 is each independently an alkyl, an amide, or an alkoxy comprising from 1 to 20 carbon atoms and R 8 is each independently a hydrogen atom, an alkoxy, or an alkyl comprising from 1 to 20 carbon atoms; a bis(silyl)alkyne having a formula (R 9 ) 3 SiCCSi(R 9 ) 3 wherein R 9 is each independently an alkyl, an amide or an alkoxy comprising from 1 to 20 carbon atoms; an alkene comprising from 1 to 20 carbon atoms; a diene comprising from 1 to 20 carbon atoms; a triene comprising from 1 to 20 carbon atoms; a silylalkene having a formula (R 10 ) 3 SiC(R 17 )C(R 17 ) 2 wherein R 17 is each independently an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; a bis(silyl)alkene having a formula (R 11 ) 3 SiCR 17 CR 17 Si(R 11 ) 3 wherein R 11 is each independently an alkyl comprising from 1 to 20 carbon atoms, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group comprising from 1 to 20 carbon atoms; an allene comprising from 3 to 20 carbon atoms; a allene having a formula (R 12 ) 2 CCC(R 12 ) 2 where R 12 is each independently a hydrogen atom, an alkyl, an alkyl silane, an alkoxysilane, or an amidosilane having a formula (R 13 ) 3 Si wherein R 13 is each independently an alkyl, alkoxy, or an amide comprising from 1 to 20 carbon atoms; an alkylisocyanide comprising from 1 to 20 carbon atoms; a silylisocyanide having a formula (R 14 ) 3 SiNC wherein R 14 is each independently an alkyl comprising from 1 to 20 carbon atoms; an allyl comprising from 1 to 20 carbon atoms; an allylsilane having a formula (R 15 ) 3 SiC(R 17 ) 2 R 17 C(R 17 ) 2 where R 15 is an alkyl, an alkoxy, or an amide comprising from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and a bis(silyl)allyl having a formula (R 16 ) 3 SiC(R 17 ) 2 CR 17 CR 17 Si(R 16 ) 3 where R 16 comprises from 1 to 20 carbon atoms and R 17 is independently a hydrogen atom or an alkyl group having from 1 to 20 carbon atoms; and

wherein an organometallic bond between M and L is selected from 2 single bonds and 1 single bond.

Assignments (3)
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 →