Beta-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same

Abstract

The β-ketoimine ligand is represented by the following formula 1: wherein R1 and R2 are each independently a C1-C5 alkyl group. A metal complex compound includes the β-ketoimine ligand. A method of forming the β-ketoimine ligand and a method of forming a thin film using the metal complex compound including β-ketoimine ligand are provided.

1 . A β-ketoimine compound represented by the following Formula 1: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently a C 1 -C 5  alkyl group. 
       
     
     
         2 . The β-ketoimine compound as claimed in  claim 1 , wherein R 1  and R 2  are each independently a methyl group or an ethyl group. 
     
     
         3 . A method for preparing a β-ketoimine compound, the method comprising:
 synthesizing an ether ester by converting a hydroxyl group of a hydroxypivalic acid ester into an alkoxy group using an alkylating agent; 
 synthesizing a β-diketone compound by allowing the ether ester to react with a ketone compound; and 
 synthesizing the β-ketoimine ligand by allowing the β-diketone compound to react with 1-dimethylamino-2-propylamine. 
 
     
     
         4 . The method as claimed in  claim 3 , wherein the β-ketoimine compound is represented by the following Formula 1: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently a C 1 -C 5  alkyl group. 
       
     
     
         5 . The method as claimed in  claim 3 , wherein the hydroxypivalic acid ester is hydroxypivalic acid methyl ester. 
     
     
         6 . The method as claimed in  claim 3 , wherein the ether ester is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein R 1  is a C 1 -C 5  alkyl group. 
       
     
     
         7 . The method as claimed in  claim 3 , wherein the ketone compound is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein R 2  is a C 1 -C 5  alkyl group. 
       
     
     
         8 . The method as claimed in  claim 3 , wherein the alkylating agent is p-toluenesulfonic acid methyl ester or p-toluenesulfonic acid ethyl ester. 
     
     
         9 . A metal complex compound represented by the following Formula 3: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently a C 1 -C 5  alkyl group, M represents a metal, and n is an integer ranging from 1 to 5. 
       
     
     
         10 . The metal complex compound as claimed in  claim 9 , wherein the metal is strontium. 
     
     
         11 . The metal complex compound as claimed in  claim 9 , wherein R 1  and R 2  are each independently a methyl group or an ethyl group. 
     
     
         12 . The metal complex compound as claimed in  claim 9 , wherein the metal complex compound is prepared by allowing a β-ketoimine ligand represented by the following Formula 1 to react with a group I or II metal or a metal raw material including the group I or II metal: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently a C 1 -C 5  alkyl group. 
       
     
     
         13 . A metal precursor for forming a metal thin film, the metal precursor including a metal complex compound as claimed in  claim 9 . 
     
     
         14 . The metal precursor as claimed in  claim 13 , wherein the metal is strontium. 
     
     
         15 . A method for forming a metal thin film on a workpiece, the method comprising:
 vaporizing a metal precursor including the metal complex compound as claimed in  claim 9 , and   supplying the vaporized metal precursor to form a metal thin film on the workpiece.   
     
     
         16 . The method as claimed in  claim 15 , further comprising supplying a reactive gas simultaneously or sequentially with the supplying of the vaporized metal precursor, wherein the forming of the metal thin film on the workpiece includes allowing the reactive gas to react with the vaporized metal precursor. 
     
     
         17 . The method as claimed in  claim 16 , wherein the reactive gas includes one or more of water, oxygen, ozone and hydrogen peroxide. 
     
     
         18 . A method for forming a metal thin film on a workpiece, the method comprising:
 supplying a first raw material including a metal complex compound including a metal and a β-ketoimine ligand represented by the following Formula 1 coordinated to the metal, and a second raw material including a reactive gas; and   allowing the first raw material and the second raw material to react with each other, thereby forming the metal thin film on the workpiece:   
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently a C 1 -C 5  alkyl group. 
       
     
     
         19 . The method as claimed in  claim 18 , wherein R 1  and R 2  are each independently a methyl group or an ethyl group, and the metal is strontium. 
     
     
         20 . The method as claimed in  claim 18 , further including supplying a third raw material including a metal precursor containing barium or titanium.