Charge transport compositions and electronic devices made with such compositions

Abstract

The present invention relates to charge transport compositions. The invention further relates to electronic devices in which there is at least one active layer comprising such charge transport compositions.

1 . An electronic device comprising at least one layer comprising a charge transport composition having at least two triarylmethane carbons, said composition having Formula II in  FIG. 2 , wherein:
 Ar 1  can be the same or different at each occurrence and is selected from aryl and heteroaryl;   R 1  is the same or different at each occurrence and is selected from H, alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, C n H a F b , and C 6 H c F d ;   R 2  is the same or different at each occurrence and is selected from arylene, heteroarylene, arylenealkylene, and heteroarylenealkylene, with the proviso that when R 2  is arylenealkylene or heteroarylenealkylene, an arylene end is attached to the triarylmethane carbon;   Q is selected from a single bond and a multivalent group;   m is an integer equal to at least 2; and   p is 0 or 1, with the proviso that when p is 0, Q is a multivalent group that is arylene or heteroarylene.   
   
   
       2 . The device of  claim 1  wherein Q is selected from a hydrocarbon group with at least two points of attachment, selected from an aliphatic group, a heteroaliphatic group, an aromatic group, and a heteroaromatic group. 
   
   
       3 . The device of  claim 2  wherein Q is selected from alkyl groups, heteroalkyl groups, alkenyl groups, heteroalkenyl groups, alkynyl groups, and heteroalkynyl groups. 
   
   
       4 . The device of  claim 1  wherein Q is selected from single-ring aromatic groups, multiple-ring aromatic groups, fused-ring aromatic groups, single-ring heteroaromatic groups, multiple-ring aromatic groups, fused-ring aromatic groups, arylamines, silanes and siloxanes. 
   
   
       5 . The device of  claim 1 , wherein Q is selected from Formulae III(a) through III(h) in  FIG. 4 . 
   
   
       6 . The device of  claim 1  wherein Ar 1  is selected from phenyl, substituted phenyl, biphenyl, and substituted biphenyl. 
   
   
       7 . The device of  claim 6  wherein Ar 1  is selected from substituted phenyl and substituted biphenyl having at least one substituent selected from alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, C n H a F b , and C 6 H c F d , where
 a, b, c, and d are 0 or an integer, such that a+b=2n+1, and c+d=5, and   n is an integer.   
   
   
       8 . The device of  claim 1  wherein Ar 1  is selected from phenyl, substituted phenyl, biphenyl, and substituted biphenyl, wherein at least one carbon atom is replaced with a heteroatom. 
   
   
       9 . The device of  claim 1  wherein R 2  is selected from phenyl, substituted phenyl, biphenyl, substituted biphenyl, pyridyl, substituted pyridyl, bipyridyl, and substituted bipyridyl. 
   
   
       10 . The device of  claim 9  wherein R 2  is selected from substituted phenyl, substituted biphenyl, and substituted pyridyl, having at least one substituent selected from heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, C n H a F b , and C 6 H c F d , where
 a, b, c, and d are 0 or an integer, such that a+b=2n+1, and c+d=5, and   n is an integer.   
   
   
       11 . The device of  claim 1 , wherein the charge transport composition is selected from Formula II(a) through Formula II(f) in FIG. 
   
   
       12 . The device of  claim 1 , wherein at least one N(R 1 ) 2  is a fused heteroaromatic ring group. 
   
   
       13 . The device of  claim 12 , wherein at least one N(R 1 ) 2  is selected from N-carbazoles, benzodiazoles, and benzotriazoles. 
   
   
       14 . The device of  claim 1 , wherein at least one X is a fused heteroaromatic ring group. 
   
   
       15 . The device of  claim 14 , wherein at least one X is selected from N-carbazoles, benzodiazoles, and benzotriazoles. 
   
   
       16 . An electronic device comprising at least one layer comprising a charge transport composition selected from Formula II in  FIG. 2 , wherein:
 Q is selected from a single bond and a multivalent group;   m is an integer from 2 through 10;   Ar 1  can be the same or different at each occurrence and is selected from aryl and heteroaryl;   R 1  is the same or different at each occurrence and is selected from H, alkyl, heteroalkyl, aryl, heteroaryl, C n H a F b , and C 6 H c F d ; and   R 2  is the same or different at each occurrence and is selected from arylene, heteroarylene, arylenealkylene, and heteroarylenealkylene, with the proviso that when R 2  is arylenealkylene or heteroarylenealkylene, an arylene end is attached to the triarylmethane carbon.   
   
   
       17 . The device of  claim 16  wherein Q is selected from Formulae III(a) through III(h) in  FIG. 4 . 
   
   
       18 . The device of  claim 16  wherein the charge transport composition is selected from Formula II(a), Formula II(b), and Formula II(c) in  FIG. 5 . 
   
   
       19 . A device of  claim 16 , wherein the device is a light-emitting diode, light-emitting electrochemical cell, or a photodetector.