Ortho-substituted thermally activated delayed fluorescence material and organic light-emitting device comprising same

Abstract

A thermally activated delayed fluorescent (TADF) material is provided. The TADF material has a form in which an electron donating group and an electron withdrawing group are connected to benzene and the electron withdrawing group is position in an ortho position to the electron donating group.

1 - 18 . (canceled) 
     
     
         19 . A light-emitting material represented by the following Chemical Formula 2: 
       
         
           
           
               
               
           
         
         in Chemical Formula 2, 
         R 1  and R 2  are, independently of each other, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R 1  and R 2  are optionally combined together with the nitrogen (N) to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl group, 
         R 17  and R 18  are, independently of each other, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C30 alkyloxy group, a substituted or unsubstituted C3-C30 aryloxy group, a C1-C9 alkylsilyl group, or a substituted or unsubstituted —NR a R b , 
         the R a  and R b  are independently selected from the group consisting of hydrogen, heavy hydrogen, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group, the R a  and R b  are optionally combined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl group, and 
         R 22  to R 25  are, independently of each other, a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted fused arylamine group, a substituted or unsubstituted phosphine or phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide or sulfone group. 
       
     
     
         20 . The light-emitting material of  claim 19 ,
 wherein, in Chemical Formula 2, R 22  to R 25  are, independently of each other, hydrogen, deuterium, a halogen group, a substituted or unsubstituted C4-C6 aryl group, or a substituted or unsubstituted C1-C3 alkyl group.   
     
     
         21 . The light-emitting material of  claim 19 ,
 wherein, in Chemical Formula 2, —NR 1 R 2  is any one of Structural Formulas A1 to A19:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         in Structural Formulas A1 to A19, 
         R 1  is the same as R 1  in the Chemical Formula 2, 
         R 11  to R 14  are, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, 
         Sub 1  and Sub 2  are, independently of each other, hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted —NR c R d , a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide group, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylsilyl group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group, 
         R c  and R d  are, independently of each other, selected from the group consisting of a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R c  and R d  are optionally be joined together with the nitrogen (N) to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl, and 
         Sub 1  and Sub 2  are, regardless of each other, optionally fused to a main body to which they are bonded to form a substituted or unsubstituted cyclic or a substituted or unsubstituted aryl. 
       
     
     
         22 . The light-emitting material of  claim 19 ,
 wherein, in Chemical Formula 2, —NR 1 R 2  is any one of Structural Formulas A1 to A45:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         in Structural Formulas A1 to A45, 
         R 11  to R 14  are, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, and 
         Sub 1  to Sub 4  are, independently of each other, hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide group, or a substituted or unsubstituted sulfone group. 
       
     
     
         23 . The light-emitting material of  claim 19 ,
 wherein, the light-emitting material represented by Chemical Formula 2 is represented by any one of the following Chemical Formulas 7 to 10:   
       
         
           
           
               
               
           
         
         in Chemical Formulas 7 to 10, 
         R 17 , R 18 , and R 22  to R 25  are as defined in the Chemical Formula 2, 
         R 11  and R 12  are, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, 
         Sub 1  and Sub 2  are, independently of each other, hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted —NR c R d , a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide group, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylsilyl group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group, 
         R c  and R d  are, independently of each other, selected from the group consisting of a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; R c  and R d  are optionally be joined together with the nitrogen (N) to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl, and 
         Sub 1  and Sub 2  are, regardless of each other, optionally fused to a main body to which they are bonded to form a substituted or unsubstituted cyclic or a substituted or unsubstituted aryl. 
       
     
     
         24 . The light-emitting material of  claim 19 ,
 wherein the triazine group in Chemical Formula 2 is the same as one of the following Structural Formulas B1 to B27:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         in Structural Formulas B1 to B27, 
         R 11  and R 12  are, independently of each other, hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group, and 
         Sub 5  and Sub 6  are, independently of each other, hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide group, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group; Sub 5  and Sub 6  are, regardless of each other, optionally fused to a main body to which they are bonded to form a substituted or unsubstituted cyclic or a substituted or unsubstituted aryl. 
       
     
     
         25 . The light-emitting material of  claim 19 ,
 wherein the light-emitting material represented by Chemical Formula 2 is represented by any one of the following Compounds 1 to 66:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         26 . An organic light emitting diode comprising sequentially stacked an anode, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode,
 wherein one selected from among the hole transporting layer, the light emitting layer and the electron transporting layer comprises the light-emitting material of  claim 19 .   
     
     
         27 . The organic light emitting diode of  claim 26 ,
 wherein the light emitting layer comprises a host material and a dopant material, and   the dopant material comprises the light-emitting material of  claim 19 .   
     
     
         28 . The organic light emitting diode of  claim 27 ,
 wherein the dopant material is a delayed fluorescent light emitting material.