Polyarylamine ketones

Abstract

Polymers comprising a backbone comprising at least one arylamine repeat moiety and at least one linking moiety, wherein the linking moiety does not comprise an aryl moiety. Ink formulations and organic electronic devices such as OLEDs or OPVs can be formed from the polymers and doped polymers. The polymers can be used in a hole injection layer, hole transport layer, a hole extraction layer, or as a host material in an emissive layer. Improved stability can be achieved in organic electronic devices such as OLEDs and OPVs.

1 - 111 . (canceled) 
     
     
         112 . An OLED device comprising a hole injection layer disposed next to a hole transport layer, wherein the hole injection layer comprises:
 at least one arylamine polymer; and   at least one dopant;   
       wherein the arylamine polymer consists essentially of a backbone consisting essentially of at least one arylamine repeat moiety and at least one linking repeat moiety, wherein the arylamine repeat and linking repeat moieties are alternating moieties, and wherein the backbone is free of oxygen atoms, wherein the linking repeat moiety consists of a bivalent carbonyl group, a bivalent sulfone group, or a group >C═C(CN)R, wherein R is, H, CN, F, or alkyl, and does not comprise an aryl moiety, and wherein the backbone consists essentially of only one aryl group between the linking repeat moiety and the amine of the arylamine, wherein the OLED device is a phosphorescent organic light emitting diode (PHOLED) device, a small molecule organic light emitting diode (SMOLED) device, or a polymer light emitting diode (PLED) device. 
     
     
         113 . The device of  claim 112 , wherein the device is a PHOLED device. 
     
     
         114 . The device of  claim 112 , wherein the device is a SMOLED device. 
     
     
         115 . The device of  claim 112 , wherein the device is a PLED device. 
     
     
         116 . The device of  claim 112 , wherein the device has an efficiency of at least about 3 cd/A. 
     
     
         117 . The device of  claim 112 , wherein the device has a voltage of about 2 to about 15 volts. 
     
     
         118 . The device of  claim 112 , wherein the device has a brightness of at least 250 cd/m 2 . 
     
     
         119 . The device of  claim 112 , wherein the device has an efficiency of at least 3 cd/A, a voltage of 2-15 volts, and a brightness of at least about 250 cd/m 2 . 
     
     
         120 . The device of  claim 112 , wherein the polymer is a crosslinked polymer. 
     
     
         121 . The device of  claim 112 , wherein the polymer is a branched polymer. 
     
     
         122 . The device of  claim 112 , wherein the polymer is a crosslinked, branched polymer. 
     
     
         123 . The device of  claim 112 , wherein the polymer has a glass transition temperature of at least 180° C. 
     
     
         124 . The device of  claim 112 , wherein the polymer is free of a melting temperature. 
     
     
         125 . The device of  claim 112 , wherein the polymer has a glass transition temperature of at least 180° C., and wherein the polymer is free of a melting temperature. 
     
     
         126 . The device of  claim 112 , wherein the polymer has a decomposition onset temperature of at least 450° C. 
     
     
         127 . The device of  claim 112 , wherein the hole injection layer has a thickness of approximately 20 nm to 60 nm. 
     
     
         128 . The device of  claim 112 , wherein the hole transport layer is applied by vapor deposition mm 
     
     
         129 . The device of  claim 112 , wherein the hole injection layer is applied by solution processing. 
     
     
         130 . An OLED device comprising a hole injection layer disposed next to a hole transport layer, wherein the hole injection layer comprises:
 at least one arylamine polymer; and   at least one dopant;   wherein the arylamine polymer consists essentially of a backbone consisting essentially of at least one arylamine repeat moiety and at least one linking repeat moiety, wherein the arylamine repeat and linking repeat moieties are alternating moieties, and wherein the backbone is free of oxygen atoms, wherein the linking repeat moiety consists of a bivalent carbonyl group, a bivalent sulfone group, or a group >C═C(CN)R, wherein R is, H, CN, F, or alkyl, and does not comprise an aryl moiety, and wherein the backbone consists essentially of only one aryl group between the linking repeat moiety and the amine of the arylamine, wherein the arylamine polymer is represented by at least one of formulae (I) or (II):   
       
         
           
           
               
               
           
         
         wherein: Ar 1  and Ar 2  are independently an unsubstituted or substituted aryl group, and LINK is the linking repeat moiety defined above; or 
       
       
         
           
           
               
               
           
         
       
       wherein: Ar 1  and Ar 2  are independently an unsubstituted or substituted aryl group and LINK is the linking repeat moiety defined above. 
     
     
         131 . An OLED device comprising a hole injection layer disposed next to a hole transport layer, wherein the hole injection layer comprises:
 at least one arylamine polymer; and   at least one dopant;   
       wherein the arylamine polymer consists essentially of a backbone consisting essentially of at least one arylamine repeat moiety and at least one linking repeat moiety, wherein the arylamine repeat and linking repeat moieties are alternating moieties, and wherein the backbone is free of oxygen atoms, wherein the linking repeat moiety consists of a bivalent carbonyl group, a bivalent sulfone group, or a group >C═C(CN)R, wherein R is, H, CN, F, or alkyl, and does not comprise an aryl moiety, and wherein the backbone consists essentially of only one aryl group between the linking repeat moiety and the amine of the arylamine, wherein the arylamine polymer is represented by at least one of formulae (III) or (IV) 
       
         
           
           
               
               
           
         
       
       wherein:
 J 1  and J 2  are independently selected from hydrogen, C 1 -C 10  alkyl, perfluoroalkyl, thioalkyl, alkoxy, alkylaryl, arylalkyl, aryloxy, heteroaryl, cyano, halo, alkylthio, trialkyl silyl, trialkoxysilyl, trialkyl silyloxy, hydroxyl, thioaryl, dialkylamine, diarylamine, cyano, halogen, quarternary ammonium salt, sulfonate ester, sulfonate salt, carboxylic ester, ketone, semifluoroalkyl, perfluoroaryl, semi-fluoroaryl, aryl, alkylsilyl, arylsilyl, alkoxysilyl, and aryloxysilyl groups; 
 x is an integer from 1 to 5, 
 y is an integer from 1 to 5, or 
 wherein the LINK moiety is the linking repeat moiety defined above and does not comprise an aryl moiety. 
 
       
         
           
           
               
               
           
         
       
       wherein:
 J 1  and J 2  are independently selected from hydrogen, C 1 -C 10  alkyl, perfluoroalkyl, 
 thioalkyl, alkoxy, alkylaryl, arylalkyl, aryloxy, heteroaryl, cyano, halo, alkylthio, trialkyl silyl, trialkoxysilyl, trialkyl silyloxy, hydroxyl, thioaryl, dialkylamine, diarylamine, cyano, halogen, quarternary ammonium salt, sulfonate ester, sulfonate salt, carboxylic ester, ketone, semifluoroalkyl, perfluoroaryl, semi-fluoroaryl, aryl, alkylsilyl, arylsilyl, alkoxysilyl, and aryloxysilyl groups, 
 x is an integer from 1 to 5, 
 y is an integer from 1 to 5, and 
 wherein the LINK moiety is the linking repeat moiety defined above and does not comprise an aryl moiety.