Complex fluorene-containing compounds for use in OLED devices

Abstract

An electroluminescent device, including a space-apart anode and cathode; and an emissive layer disposed between the space-apart anode and cathode and including an organic compound having a complex fluorene structure represented by one of the following formulas: wherein: X 1 , X 2 , X 3 , and X 4 are individually the same or different and include a moiety containing CH or N; R 1 , R 2 , R 3 , and R 4 are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4 or both are groups that form fused aromatic or heteroaromatic rings.

What is claimed is:  
     
         1 . An electroluminescent device, comprising 
 a) a space-apart anode and cathode; and    b) an emissive layer disposed between the space-apart anode and cathode and including an organic compound having a complex fluorene structure represented by one of the following formulas:                          wherein:    X 1 , X 2 , X 3 , and X 4  are individually the same or different and include a moiety containing CH or N; R 1 , R 2 , R 3 , and R 4  are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4  or both are groups that form fused aromatic or heteroaromatic rings.    
     
     
         2 . The electroluminescent device of  claim 1  wherein the organic compound having the complex fluorene structure is a small molecule or a polymer or mixture thereof.  
     
     
         3 . The electroluminescent device of  claim 1  wherein the organic compound having the complex fluorene structure is a small molecule represented by formula:  
       
         
           
           
               
               
           
         
       
       wherein Y 1  and Y 2  each individually represent a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, or heteroaryl or other conjugated groups, and y 1  and y 2  are integers from 0 to 6, and wherein Y 1  and Y 2  are the same or different.  
     
     
         4 . The organic compound in  claim 1  wherein the organic compound having the complex fluorene structure is a polymer represented by repeating units of formula (V) or formula (VI)  
       
         
           
           
               
               
           
         
       
       wherein:  
       X 5  and X 6  are linking groups, Y 1  and Y 2  are each individually represented as a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, or heteroaryl or other conjugated groups, and y 1  and Y 2  are integers from 0 to 6, and x is an integer from 0 to 6.  
     
     
         5 . A method of making an electroluminescent device, comprising the steps of: 
 a) providing a space-apart anode and cathode; and    b) depositing an emissive layer between the space-apart anode and cathode and including an organic compound having a complex small molecule or fluorene structure represented by one of the following formulas                          wherein:    X 1 , X 2 , X 3 , and X 4  are individually the same or different and include a moiety containing CH or N; R 1 , R 2 , R 3 , and R 4  are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4  or both are groups that form fused aromatic or heteroaromatic rings; or R 3 , or R 4  or both represent one or more than one substituents.    
     
     
         6 . The method of  claim 5  wherein the organic compound having the complex fluorene structure is a polymer produced according to the following reaction: contacting (a) aromatic monomers having at least two reactive trifluorosulfonate groups and aromatic monomers having at least two reactive boron derivative groups selected from boronic acid, boronic ester, or borane groups or (b) aromatic monomers having one reactive trifluorosulfonaate group and one boron derivative group selected from boronic acid, boronic ester, or borane groups, with each other; in a reaction mixture which comprises: (i) a catalytic amount of a catalyst, (ii) an organic or inorganic base, and (iii) an organic solvent, under reaction conditions sufficient to form conjugated polymer.  
     
     
         7 . An electroluminescent device which comprises an anode, a cathode, and an organic compound disposed between the space-apart anode and cathode, the organic compound being doped with one or more fluorescent dyes, phosphorescent dopants, or other light emitting materials, the organic compound including complex fluorene structure is represented by one of the following formulas  
       
         
           
           
               
               
           
         
       
       wherein:  
       X 1 , X 2 , X 3 , and X 4  are individually the same or different and include a moiety containing CH or N; R 1 , R 2 , R 3 , and R 4  are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4  or both are groups that form fused aromatic or heteroaromatic rings; or R 3 , or R 4  or both represent one or more than one substituents.