(Pentaphenyl)phenyl Group Containing Compound, Polymeric Derivative Thereof And Method For Forming The Same

Abstract

The present invention discloses an iridium complex containing a (pentaphenyl)phenyl ligand, having the following general equation: in which G is primary ligand, R′ and R″ are auxiliary ligands. On the other hand, the present invention discloses a compound with a 9-[(pentaphenyl)phenyl]carbazole structure and its polymeric derivative.

1 . An iridium complex containing a (pentaphenyl)phenyl ligand, having the following general equation: 
     
       
         
         
             
             
         
       
       wherein G comprises one selected from the group consisting of the following: 
     
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     in which R′ and R″ are auxiliary ligands and R 1 ˜R 117  can be the same or different and they are independently selected from the group consisting of the following: hydrogen atom and electron-withdrawing group. 
   
   
       2 . The iridium complex according to  claim 1 , wherein said R′ and R″ are each selected from one of the following: 
     
       
         
         
             
             
         
       
     
   
   
       3 . The iridium complex according to  claim 1 , wherein said electron-withdrawing group comprises one selected from the group consisting of the following: fluoro-group and trifluoro-methyl group. 
   
   
       4 . The iridium complex according to  claim 1 , comprising one selected from the group consisting of the following: 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
   
   
       5 . The iridium complex according to  claim 1 , wherein the iridium complex is utilized in a phosphorescence device. 
   
   
       6 . The iridium complex according to  claim 5 , wherein the iridium complex is used as a guest material in a phosphorescence device. 
   
   
       7 . A method for forming an iridium complex containing a (pentaphenyl)phenyl ligand, comprising:
 providing a first reagent, having the following general equation:   
     
       
         
         
             
             
         
       
     
     in which Z is a group VA element, X 1  and X 2  are independently selected from the group consisting of the following: chlorine (Cl), bromine (Br), and iodine (I), and X 1 is different from X 2 ;
 providing a second reagent, having the following general equation: 
 
     
       
         
         
             
             
         
       
     
     in which R is a hydrogen atom, alkyl group or aryl group, R 1 , R 2 , R 3 , and R 4  can be the same or different, and R 1 , R 2 , R 3 , and R 4  are independently selected from the group consisting of the following: hydrogen atom and electron-withdrawing group;
 performing a Suzuki coupling reaction between said first reagent and said second reagent to form a first intermediate with the following structure: 
 
     
       
         
         
             
             
         
       
       performing a Sonogashira coupling reaction between phenylacetylene and said first intermediate to form a second intermediate having the following general equation: 
     
     
       
         
         
             
             
         
       
       performing a Diels-Alder reaction between tetraphenylcyclopentadienone (TPCDO) and said second intermediate to form a third intermediate having the following general equation: 
     
     
       
         
         
             
             
         
       
       performing an addition reaction between iridium chloride and said third intermediate to form a halogen-bridged dimer iridium complex having the following general equation: 
     
     
       
         
         
             
             
         
       
     
     in which X 3  is selected from the group consisting of the following: chlorine (Cl), bromine (Br), and iodine (I); and
 performing a substitution reaction between a chelating agent and said halogen-bridged dimer iridium complex to form said iridium complex containing a (pentaphenyl)phenyl ligand wherein said iridium complex containing a (pentaphenyl)phenyl ligand has the following general equation: 
 
     
       
         
         
             
             
         
       
     
   
   
       8 . A compound with a 9-[(pentaphenyl)phenyl]carbazole structure, having the following general equation: 
     
       
         
         
             
             
         
       
     
     in which G 1  and G 2  can be the same or different and G 1  and G 2  are independently selected from the group consisting of the following: hydrogen atom, carboxyl group, hydroxyl group, amino group, double bond group or triple bond group, halogen atom, 
     
       
         
         
             
             
         
       
     
     —B(OR) 2 , 
     
       
         
         
             
             
         
       
     
     and —Ar-G 3 , where R is a hydrogen atom, alkyl group, or aryl group, Ar is an aryl group, G 3  is a hydrogen atom, carboxyl group, hydroxyl group, amino group, double bond group or triple bond group. 
   
   
       9 . The compound according to  claim 8 , wherein said compound with a 9-[(pentaphenyl)phenyl]carbazole structure is utilized in an organic solar cell device. 
   
   
       10 . The compound according to  claim 8 , wherein said compound with a 9-[(pentaphenyl)phenyl]carbazole structure is utilized in an organic electroluminescence device and/or phosphorescence device. 
   
   
       11 . The compound according to  claim 10 , wherein said compound with a 9-[(pentaphenyl)phenyl]carbazole structure is used as a hole injection material, hole transport material, emitting material or host material in an organic electroluminescence device and/ or phosphorescence device. 
   
   
       12 . A polymer derived from a 9-[(pentaphenyl)phenyl]carbazole structure, formed by a reaction between said compound with a 9-[(pentaphenyl)phenyl]carbazole structure according to  claim 8  and at least one reactive monomer, wherein said reactive monomer is selected from the group consisting of the following: 
     
       
         
         
             
             
         
       
     
     in which R 1 , R 2 , R 3 , R 4 , and R 5  are independently selected from the group consisting of the following: alkyl group and aryl group, G 4  is a halogen atom, —B(OR) 2 , 
     
       
         
         
             
             
         
       
     
     carboxyl group, hydroxyl group, amino group, double bond group or triple bond group, where R is a hydrogen atom, alkyl group, or aryl group. 
   
   
       13 . The polymer according to  claim 12 , wherein said polymer derived from a 9-[(pentaphenyl)phenyl]carbazole structure is utilized in an organic solar cell device. 
   
   
       14 . The compound according to  claim 12 , wherein said polymer derived from a 9-[(pentaphenyl)phenyl]carbazole structure is utilized in an organic electroluminescence device and/ or phosphorescence device. 
   
   
       15 . The compound according to  claim 14 , wherein said polymer derived from a 9-[(pentaphenyl)phenyl]carbazole structure is used as a hole injection material, hole transport material, emitting material or host material in an organic electroluminescence device and/ or phosphorescence device. 
   
   
       16 . A method for forming 9-[(pentaphenyl)phenyl]carbazole, comprising:
 providing a carbazole compound and a dihalo compound, each having the following general equation:   
     
       
         
         
             
             
         
       
     
     respectively, in which X 1  and X 2  can be the same or different and X 1  and X 2  are independently selected from the group consisting of the following: chlorine (Cl), bromine (Br), and iodine (I);
 performing a substitution reaction between said carbazole and said dihalo compound to form a first intermediate having the following structural equation: 
 
     
       
         
         
             
             
         
       
       performing a Sonogashira coupling reaction between phenylacetylene and said first intermediate to form a second intermediate having the following general equation: 
     
     
       
         
         
             
             
         
       
     
     performing a Diels-Alder reaction between tetraphenylcyclopentadienone (TPCDO) and said second intermediate to form 9-[(pentaphenyl)phenyl]carbazole having the following general equation: