Organic Electroluminescent Materials and Devices

Abstract

The present invention relates to novel light-emitting materials. These materials comprise a side chain that includes a fully deuterated or partially deuterated alkyl chain. This new side chain could improve device lifetime compared to nondeuterated side chains.

1 . A composition comprising a first compound;
 wherein the first compound is capable of functioning as a fluorescent emitter in an organic light emitting device at room temperature;   wherein the first compound has at least one aromatic ring and at least one substituent R;   wherein each of the at least one R is independently selected from the group consisting of partially deuterated alkyl, partially deuterated cycloalkyl, fully deuterated alkyl, fully deuterated cycloalkyl and combinations thereof;   wherein each of the at least one R is directly bonded to one of the aromatic rings; and   wherein in each of the at least one R, a C having a deuterium attached thereto is attached to the aromatic ring.   
     
     
         2 . The composition of  claim 1 , wherein each of the at least one R is independently selected from the group consisting of partially deuterated alkyl, partially deuterated cycloalkyl, and combinations thereof 
     
     
         3 . The composition of  claim 1 , wherein each of the at least one R is independently selected from the group consisting of fully deuterated alkyl, fully deuterated cycloalkyl, and combinations thereof 
     
     
         4 . The composition of  claim 1 , wherein the alkyl contains at least two carbon atoms. 
     
     
         5 . The composition of  claim 1 , wherein the alkyl contains at least three carbon atoms. 
     
     
         6 . (canceled) 
     
     
         7 . The composition of  claim 1 , wherein the alkyl or cycloalkyl contains at least one fluorine atom. 
     
     
         8 . The composition of  claim 1 , wherein the alkyl is a straight chain alkyl. 
     
     
         9 . The composition of  claim 1 , wherein the alkyl is a branched chain alkyl. 
     
     
         10 . The composition of  claim 1 , wherein the alkyl or cycloalkyl contains primary, secondary, or tertiary carbons only. 
     
     
         11 . The composition of  claim 1 , wherein the cycloalkyl is monocyclic or bicyclic alkyl. 
     
     
         12 . The composition of  claim 1 , wherein the first compound is capable of emitting light from a singlet excited state to a singlet ground state at room temperature. 
     
     
         13 . The composition of  claim 1 , wherein each of the at least one R is independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         14 . The composition of  claim 1 , wherein the first compound comprises at least one organic group selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       and aza analogues thereof;
 wherein A is selected from the group consisting of O, S, Se, NR′ and CR′R″; 
 wherein R′ and R″ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
 wherein two adjacent substituents of R′ and R″ are optionally joined to form a ring. 
 
     
     
         15 . The composition of  claim 1 , wherein the first compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R 1  to R 5  each independently represent from mono to maximum number of substitutions they can have, or no substitution; 
         wherein R 1  to R 5  are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
         wherein at least one of R 1  to R 5  is R. 
       
     
     
         16 . The composition of  claim 1 , wherein the first compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein each R can be same or different. 
       
     
     
         17 . An organic light-emitting device (OLED) comprising:
 an anode;   a cathode; and   an organic layer, disposed between the anode and the cathode, comprising a first compound;   wherein the first compound is capable of functioning as a fluorescent emitter in an organic light emitting device at room temperature;   wherein the first compound has at least one aromatic ring and at least one substituent R;   wherein each of the at least one R is independently selected from the group consisting of partially deuterated alkyl, partially deuterated cycloalkyl, fully deuterated alkyl, fully deuterated cycloalkyl and combinations thereof;   wherein each of the at least one R is directly bonded to one of the aromatic rings; and   wherein in each of the at least one R, C having a deuterium attached thereto is attached to the aromatic ring.   
     
     
         18 . The OLED of  claim 17 , wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel. 
     
     
         19 . The OLED of  claim 17 , wherein the OLED further comprises a first phosphorescent emitting material. 
     
     
         20 . (canceled) 
     
     
         21 . The OLED of  claim 17 , wherein the OLED emits a white light. 
     
     
         22 . A formulation comprising a first compound;
 wherein the first compound is capable of functioning as a fluorescent emitter in an organic light emitting device at room temperature;   wherein the first compound has at least one aromatic ring and at least one substituent R;   wherein each of the at least one R is independently selected from the group consisting of partially deuterated alkyl, partially deuterated cycloalkyl, fully deuterated alkyl, fully deuterated cycloalkyl and combinations thereof;   wherein each of the at least one R is directly bonded to one of the aromatic rings; and   wherein in each of the at least one R, C having a deuterium attached thereto is attached to the aromatic ring.