Aminobenzene compositions and related devices and methods

Abstract

Oligomers and/or polymers comprising a backbone comprising arylamine and fluorinated alkyleneoxy moieties which may be crosslinked. Ink formulations and devices can be formed from the oligomers or polymers, or corresponding monomers. Doped compositions can be formed. Charge injection and transport layers can be formed. Improved stability can be achieved in organic electronic devices such as OLEDs and OPVs.

1 . A composition comprising a polymeric or oligomeric backbone comprising at least one repeat moiety comprising at least one O-arylamine, and at least one repeat moiety comprising at least one fluorinated alkyleneoxy. 
     
     
         2 . The composition of  claim 1 , wherein the repeat moiety comprising O-arylamine and the repeat moiety comprising fluorinated alkyleneoxy are alternating moieties. 
     
     
         3 . The composition of  claim 1 , wherein the O-arylamine comprises triarylamine. 
     
     
         4 . The composition of  claim 1 , wherein the O-arylamine moiety comprises at least two nitrogen atoms. 
     
     
         5 . The composition of  claim 1 , wherein the fluorinated alkyleneoxy comprises a C 1 -C 10  alkylene ether. 
     
     
         6 . The composition of  claim 1 , wherein the fluorinated alkyleneoxy comprises a fluorinated C 1 -C 10  vinyl ether. 
     
     
         7 . The composition of  claim 1 , wherein the fluorinated alkyleneoxy comprises a trifluoroalkyleneoxy moiety. 
     
     
         8 . The composition of  claim 1 , wherein the composition comprises a soluble, linear polymer comprising the O-arylamine and the fluorinated alkyleneoxy. 
     
     
         9 . The composition of  claim 1 , wherein the composition is crosslinked. 
     
     
         10 . An oligomer or polymer comprising repeat units represented by
   O—Ar 1  and  (I)
     O—R 1 —O—Ar 2 —O—R 2   (II)
   wherein,   Ar 1  comprises arylamine,   Ar 2  comprises an aryl, and   R 1  and R 2  are independently selected from C 1 -C 10  fluorinated alkylenes.   
     
     
         11 . The oligomer or polymer of  claim 10 , wherein the repeat units (I) and (II) are alternating. 
     
     
         12 . The oligomer or polymer of  claim 10 , wherein Ar 1  is represented by 
       
         
           
           
               
               
           
         
         wherein,
 J 1 , J 2  and J 3  are independently selected from hydrogen, C 1 -C 10  alkyl, perfluoroalkyl, thioalkyl, alkoxy, alkylaryl, arylalkyl, aryloxy, heteroaryl, cyano, halo and alkylthio groups, 
 k is an integer from 1 to 4, 
 m is an integer from 1 to 5, and 
 n is an integer from 1 to 5; 
 
         or wherein Ar 1  is represented by 
       
       
         
           
           
               
               
           
         
       
     
     
         13 . (canceled) 
     
     
         14 . The oligomer or polymer of  claim 10 , wherein Ar 2  is represented by 
       
         
           
           
               
               
           
         
         wherein z is an integer from 1 to 5; 
         or wherein Ar 2  is represented by: 
       
       
         
           
           
               
               
           
         
         wherein
 J 1 , J 2  and J 3  are independently selected from hydrogen, C 1 -C 10  alkyl, perfluoroalkyl, thioalkyl, alkoxy, alkylaryl, arylalkyl, aryloxy, heteroaryl, cyano, halo and alkylthio groups, 
 k is an integer from 1 to 4, 
 m is an integer from 1 to 5, and 
 n is an integer from 1 to 5; 
 
         or wherein Ar 2  is represented by 
       
       
         
           
           
               
               
           
         
         wherein,
 R 3  is an optionally fluorinated C 1 -C 10  alkyl, and 
 Z is an integer from 1 to 5; 
 
         or wherein Ar 2  is represented by 
       
       
         
           
           
               
               
           
         
       
     
     
         15 - 17 . (canceled) 
     
     
         18 . The oligomer or polymer of  claim 10 , wherein R 1  and R 2  are independently selected from fluoroalkyl. 
     
     
         19 . The oligomer or polymer of  claim 10 , wherein R 1  and R 2  are trifluoroethyl, and wherein the oligomer or polymer is insoluble and crosslinked or soluble. 
     
     
         20 . A method of making the oligomer or polymer of  claim 10  comprising:
 co-polymerizing a first monomer represented by
   HO—Ar 4 —OH  (X)
 
 
 with a second monomer represented by
   R 5 —O—Ar 5 —O—R 6   (XII)
 
 
 wherein Ar 4  and Ar 5  are independently chosen from an aryl moiety or an arylamine moiety, such that at least one of Ar 4  and Ar 5  being an arylamine, and 
 R 5  and R 6  independently represent a fluorinated C 1 -C 10  alkylene. 
 
     
     
         21 . The method of  claim 20  wherein Ar 4  is represented by 
       
         
           
           
               
               
           
         
         wherein z is an integer from 1 to 5; 
         or wherein Ar 4  is represented by 
       
       
         
           
           
               
               
           
         
         
           wherein, 
           J 1 , J 2  and J 3  are independently selected from hydrogen, C 1 -C 10  alkyl, perfluoroalkyl, thioalkyl, alkoxy, alkylaryl, arylalkyl, aryloxy, heteroaryl, cyano, halo and alkylthio groups, 
           k is an integer from 1 to 4, 
           m is an integer from 1 to 5, and 
           n is an integer from 1 to 5; 
         
         or wherein Ar 4  is represented by 
       
       
         
           
           
               
               
           
         
       
     
     
         22 - 23 . (canceled) 
     
     
         24 . The method of  claim 20 , wherein Ar 5  is represented by 
       
         
           
           
               
               
           
         
         where z is 1-5; 
       
       or wherein Ar 5  is represented by 
       
         
           
           
               
               
           
         
         wherein, 
         J 1 , J 2  and J 3  are independently selected from hydrogen, C 1 -C 10  alkyl, perfluoroalkyl, thioalkyl, alkoxy, alkylaryl, arylalkyl, aryloxy, heteroaryl, cyano, halo and alkylthio groups, 
         k is an integer from 1 to 4, 
         m is an integer from 1 to 5, and 
         n is an integer from 1 to 5; 
       
       or wherein Ar 5  is represented by 
       
         
           
           
               
               
           
         
       
       or wherein Ar 5  is represented by 
       
         
           
           
               
               
           
         
         wherein, 
         R 3  is an optionally fluorinated C 1 -C 10  alkyl, and 
         Z is an integer from 1 to 5. 
       
     
     
         25 - 27 . (canceled) 
     
     
         28 . The method of  claim 20 , wherein R 5  and R 6  are independently selected from fluorinated C 1 -C 10  alkylene. 
     
     
         29 . The method of  claim 20 , wherein R 5  and R 6  are trifluoroalkylene. 
     
     
         30 - 39 . (canceled) 
     
     
         40 . A composition comprising:
 an oligomer or polymer comprising repeat units represented by
   O—Ar 1  and  (I)
 
   O—R 1 —O—Ar 2 —O—R 2   (II)
 
 wherein, 
 Ar 1  is an arylamine, 
 Ar 2  comprises an aryl, and 
 R 1  and R 2  are independently selected from C 1 -C 10  fluorinated alkyls; and 
   at least one solvent.   
     
     
         41 - 45 . (canceled) 
     
     
         46 . The composition of  claim 40 , comprising from about 50% wt to about 99% wt of said at least one solvent. 
     
     
         47 . The composition of  claim 40 , comprising from about 0.01% wt to about 5% wt of said oligomer or polymer. 
     
     
         48 - 49 . (canceled) 
     
     
         50 . A device comprising a layer comprising an oligomer or polymer comprising repeat units represented by
   O—Ar 1  and  (I)
     O—R 1 —O—Ar 2 —O—R 2   (II)
   wherein,   Ar 1  is an arylamine,   Ar 2  comprises an aryl, and   R 1  and R 2  are independently selected from C 1 -C 10  fluorinated alkyl.   
     
     
         51 . The device of  claim 50 , wherein said device is an organic light-emitting diode, polymer light emitting diode, phosphorescent organic light-emitting diode or organic photovoltaic device. 
     
     
         52 - 67 . (canceled) 
     
     
         68 . A composition comprising a polymeric or oligomeric backbone comprising at least one repeat moiety adapted to provide hole transport and at least one fluorinated repeat moiety, wherein the fluorinated repeat moiety is adapted from a monomer represented by 
       
         
           
           
               
               
           
         
       
       and
 wherein R is represented by one of 
 
       
         
           
           
               
               
           
         
       
     
     
         69 - 70 . (canceled)