Deuterated compounds for electronic applications

Abstract

This invention relates to deuterated indolocarbazole compounds that are useful in electronic applications. It also relates to electronic devices in which the active layer includes such a deuterated compound.

1 . An indolocarbazole compound having Formula I or Formula II: 
       
         
           
           
               
               
           
         
       
       wherein:
 Ar 1  is an aromatic electron transporting group; 
 Ar 2  is selected from the group consisting of aryl groups and aromatic electron transporting groups; and 
 R 1  and R 2  are the same or different at each occurrence and are selected from the group consisting of H, D and aryl; 
 
       wherein the compound has at least one D. 
     
     
         2 . The compound of  claim 1 , which is at least 10% deuterated. 
     
     
         3 . The compound of  claim 1 , which is at least 50% deuterated. 
     
     
         4 . The compound of  claim 1 , which is 100% deuterated. 
     
     
         5 . The compound of  claim 1 , wherein Ar 1  is a nitrogen-containing heteroaromatic group. 
     
     
         6 . The compound of  claim 5 , wherein the nitrogen-containing heteroaromatic group is selected from the group consisting of 
       
         
           
           
               
               
           
         
       
       wherein:
 Ar 3  is an aryl group; 
 R 3  is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, aryl, aryloxy, siloxane, and silyl; 
 a is an integer from 0-4; 
 b is an integer from 0-3; 
 c is an integer from 0-2; 
 d is an integer from 0-5; and 
 e is 0 or 1. 
 
     
     
         7 . The compound of  claim 6 , wherein R 3  is selected from D and aryl. 
     
     
         8 . The compound of  claim 1 , wherein at least one of Ar 2  is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthracenyl, phenylnaphthylene, naphthylphenylene, deuterated derivatives thereof, and a group having Formula III: 
       
         
           
           
               
               
           
         
       
       where:
 R 4  is the same or different at each occurrence and is selected from the group consisting of H, D, alkyl, alkoxy, siloxane and silyl, or adjacent R 4  groups may be joined together to form an aromatic ring; and 
 m is the same or different at each occurrence and is an integer from 1 to 6. 
 
     
     
         9 . The compound of  claim 1 , wherein R 1  and R 2  are aryl. 
     
     
         10 . The compound of  claim 1 , wherein R 1  and R 2  are H or D. 
     
     
         11 . The compound of  claim 1 , selected from Compounds H1 through H14. 
     
     
         12 . An organic thin-film transistor comprising:
 a substrate   an insulating layer;   a gate electrode;   a source electrode;   a drain electrode; and   an organic semiconductor layer comprising an indolocarbazole compound having at least one deuterium substituent;   wherein the insulating layer, the gate electrode, the semiconductor layer, the source electrode and the drain electrode can be arranged in any sequence provided that the gate electrode and the semiconductor layer both contact the insulating layer, the source electrode and the drain electrode both contact the semiconductor layer and the electrodes are not in contact with each other.   
     
     
         13 . The organic thin-film transistor of  claim 12 , wherein the indolocarbazole compound has Formula I or Formula II: 
       
         
           
           
               
               
           
         
       
       wherein:
 Ar 1  is an aromatic electron transporting group; 
 Ar 2  is selected from the group consisting of aryl groups and aromatic electron transporting groups; and 
 R 1  and R 2  are the same or different at each occurrence and are selected from the group consisting of H, D and aryl; 
 wherein the compound has at least one D. 
 
     
     
         14 . An organic electronic device comprising a first electrical contact layer, a second electrical contact layer, and at least one active layer therebetween, wherein the active layer comprises an indolocarbazole compound having at least one deuterium substituent. 
     
     
         15 . The device of  claim 14 , wherein the indolocarbazole compound has Formula I or Formula II: 
       
         
           
           
               
               
           
         
       
       wherein:
 Ar 1  is an aromatic electron transporting group; 
 Ar 2  is selected from the group consisting of aryl groups and aromatic electron transporting groups; and 
 R 1  and R 2  are the same or different at each occurrence and are selected from the group consisting of H, D and aryl; 
 wherein the compound has at least one D. 
 
     
     
         16 . The device of  claim 14 , wherein the active layer is an electroactive layer which further comprises an electroactive dopant capable of electroluminescence having an emission maximum between 380 and 750 nm. 
     
     
         17 . The device of  claim 15 , wherein the active layer is an electroactive layer and consists essentially of a compound having Formula I or Formula II and an electroactive dopant compound. 
     
     
         18 . The device of  claim 16 , wherein the electroactive dopant is an organometallic complex. 
     
     
         19 . The device of  claim 18 , wherein the organometallic complex is a cyclometalated complex of iridium or platinum. 
     
     
         20 . The device of  claim 14 , further comprising a hole injection layer between the first electrical contact layer and the active layer. 
     
     
         21 . The device of  claim 20 , wherein the hole injection layer comprises at least one electrically conductive polymer and at least one fluorinated acid polymer.