Imidazo derivatives

Abstract

The present invention relates to imidizo derivatives containing a plurality of imidizo moieties linked by aryl or heteroaryl groups. The resultant imidizo derivates may advantageously be used in organic electronic devices, such as multi-layer organic electroluminescent devices or organic photovoltaic devices, and in chemical sensing applications as a host material.

1 . A compound of the following formula: 
       
         
           
           
               
               
           
         
         wherein, R 1 , R 2 , R 3 , R 4 , and R 5  are each independently a hydrogen, an alkyl, an alkenyl, an alkynyl, an alkoxyl, an amino, an alkyl-substituted amino, an aryl-substituted amino, an aryl, a heteroaryl, a cyano group, a fluoro group, a chloro group, or a bromo group; 
         wherein n is an integer from 2 to 4; and 
         wherein Ar is a linkage unit comprising aryl or heteroaryl or substituted aryl or heteroaryl groups. 
       
     
     
         2 . The compound of  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5  are linked to form one of a saturated ring, unsaturated ring, aromatic ring, non-aromatic ring, or heteroaromatic ring. 
     
     
         3 . The method of making the compound of  claim 1 , formed by the following scheme: 
       
         
           
           
               
               
           
         
         wherein, R 1 , R 2 , R 3 , R 4 , and R 5  are each independently hydrogen, an alkyl, an alkenyl, an alkynyl, an alkoxyl, an amino, an alkyl-substituted amino, an aryl-substituted amino, an aryl, a heteroaryl, a cyano group, a fluoro group, a chloro group, or a bromo group; 
         wherein X is one of chloro, bromo, iodo, or cyano; 
         wherein Ar is a linkage unit comprising aryl or heteroaryl groups or substituted aryl or heteroaryl groups; 
         wherein Z is a reactive group; and 
         wherein n is an integer from 2 to 4. 
       
     
     
         4 . The method of  claim 3 , wherein R 1 , R 2 , R 3 , R 4 , and R 5  are linked to form one of a saturated ring, unsaturated ring, aromatic ring, non-aromatic ring, or heteroaromatic ring. 
     
     
         5 . The method of  claim 3 , wherein the compound is 1,4-bis(3-phenylimidazo[1,5-a]pyridin-1-yl)benzene. 
       
         
           
           
               
               
           
         
       
     
     
         6 . The method of  claim 3 , wherein the compound is 1,3-bis(3-phenylimidazo[1,5-a]pyridine-1-yl)benzene. 
       
         
           
           
               
               
           
         
       
     
     
         7 . The method of  claim 3 , wherein the compound is 1,3-bis(3-(pyridin-2-yl)imidazo[1,5-a]pyridin-1-yl)benzene. 
       
         
           
           
               
               
           
         
       
     
     
         8 . The method of  claim 3 , wherein the compound is 1,3-bis(3-(pyrimidin-2-yl)imidazo[1,5-a]pyridin-1-yl)benzene. 
       
         
           
           
               
               
           
         
       
     
     
         9 . The method of  claim 3 , wherein the compound is 1,3,5-tris(3-phenylimidazo[1,5-a]pyridin-1-yl)benzene. 
       
         
           
           
               
               
           
         
       
     
     
         10 . The method of  claim 3 , wherein the compound is 1,3,5-tris(3-(pyridin-2-yl)imidazo[1,5-a]pyridin-1-yl)benzene. 
       
         
           
           
               
               
           
         
       
     
     
         11 . The method of  claim 3 , wherein the compound is 2,4,6-tris(3-phenylimidazo[1,5-a]pyridin-1-yl)-1,3,5-triazine. 
       
         
           
           
               
               
           
         
       
     
     
         12 . An organic electroluminescence device, comprising:
 a support layer;   an anode disposed atop the support layer;   a cathode disposed opposite the anode; and   an organic electroluminescence material disposed between the anode and the cathode, wherein the organic electroluminescence material comprises a compound of the following formula:   
       
         
           
           
               
               
           
         
         wherein, R 1 , R 2 , R 3 , R 4 , and R 5  are each independently a hydrogen, an alkyl, an alkenyl, an alkynyl, an alkoxyl, an amino, an alkyl-substituted amino, an aryl-substituted amino, an aryl, a heteroaryl, a cyano group, a fluoro group, a chloro group, or a bromo group; wherein n is an integer from 2 to 4; and wherein Ar is a linkage unit comprising aryl or heteroaryl or substituted aryl or heteroaryl groups. 
       
     
     
         13 . The device of  claim 12 , wherein R 1 , R 2 , R 3 , R 4 , and R 5  are linked to form one of a saturated ring, unsaturated ring, aromatic ring, non-aromatic ring, or heteroaromatic ring. 
     
     
         14 . The device of  claim 12 , wherein the support layer comprises one of an optically transparent material or an opaque material. 
     
     
         15 . The device of  claim 12 , wherein the organic electroluminescence material further comprises a hole-transport layer disposed atop the anode and an electron-transport layer disposed atop the hole-transport layer. 
     
     
         16 . The device of  claim 15 , further comprising a luminescent layer disposed between the hole-transport layer and the electron-transport layer. 
     
     
         17 . The device of  claim 12 , wherein the anode and the cathode are connected to a power source.