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.

What is claimed is: 
     
         1 . A light-emitting material represented by Chemical Formula 1: 
       
         
           
           
               
               
           
         
         in the Chemical Formula 1, 
         R EDG  is an electron donating group, 
         R EWG  is an electron withdrawing group, 
         R 5  to R 8  are, independently of each other, a hydrogen atom, a heavy hydrogen atom, a halogen group, a substituted or unsubstituted C 4 -C 6  aryl group, or a substituted or unsubstituted C 1 -C 3  alkyl group. 
       
     
     
         2 . The light-emitting material of  claim 1 , wherein the light-emitting material represented by Chemical Formula 1 is represented by any one of Chemical Formulas 2 to 4: 
       
         
           
           
               
               
           
         
         in Chemical Formulas 2 to 4, 
         R 1  to R 12  are, independently of each other, a substituted or unsubstituted C 1 -C 9  alkyl group, a substituted or unsubstituted C 5 -C 30  cycloalkyl group, a substituted or unsubstituted C 6 -C 30  aryl group, a substituted or unsubstituted C 6 -C 30  alkylaryl group, a substituted or unsubstituted C 6 -C 30  aralkyl group, or a substituted or unsubstituted C 3 -C 30  heteroaryl group; and R 1  and R 2 , R 3  and R 4 , R 5  and R 6 , R 7  and R 8 , R 9  and R 10 , or R 11  and R 12  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, 
         R 17  to R 19  are, independently of each other, a cyano group, a substituted or unsubstituted C 1 -C 9  alkyl group, a substituted or unsubstituted C 5 -C 30  cycloalkyl group, a substituted or unsubstituted C 6 -C 30  aryl group, a substituted or unsubstituted C 6 -C 30  alkylaryl group, a substituted or unsubstituted C 6 -C 30  aralkyl group, a substituted or unsubstituted C 3 -C 30  heteroaryl group, a substituted or unsubstituted C 1 -C 30  alkyloxy group, a substituted or unsubstituted C 3 -C 30  aryloxy group, a C 1 -C 9  alkylsilyl group, or a substituted or unsubstituted —NR a R b , 
         the R a  and R b  are independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted C 1 -C 9  alkyl group, a substituted or unsubstituted C 5 -C 30  cycloalkyl group, a substituted or unsubstituted C 6 -C 30  aryl group, a substituted or unsubstituted C 6 -C 30  aralkyl group, or a substituted or unsubstituted C 3 -C 30  heteroaryl group; and 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 45  are, independently of each other, hydrogen, deuterium, a halogen group, a substituted or unsubstituted C 4 -C 6  aryl group, or a substituted or unsubstituted C 1 -C 3  alkyl group. 
       
     
     
         3 . The light-emitting material of  claim 2 ,
 wherein the compound represented by Chemical Formula 2 is represented by Chemical Formula 5:   
       
         
           
           
               
               
           
         
         in Chemical Formula 5, R 1 , R 2 , and R 22  to R 25  are as defined in Chemical Formula 2, 
         Sub 5  and Sub 6  are, independently of each other, hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 -C 9  alkyl group, a substituted or unsubstituted C 6 -C 30  aryl group, a substituted or unsubstituted C 3 -C 30  heteroaryl group, a substituted or unsubstituted C 1 -C 9  alkyloxy group, a substituted or unsubstituted —NR e R f , 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; and Sub 5  and Sub 6  are, independently 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, 
         R e  and R f  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; and Re and R f  are optionally joined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl. 
       
     
     
         4 . The light-emitting material of  claim 3 ,
 wherein, in Chemical Formula 5, —NR 1 R 2  is any one selected from Structural Formulas A6, A8, A9, and A10:   
       
         
           
           
               
               
           
         
         in Structural Formulas A6, A8, A9, and A10, 
         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; and Sub 1  and Sub 2  are, independently 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, 
         R c  and R d  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 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; and R c  and R d  are optionally joined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl. 
       
     
     
         5 . The light-emitting material of  claim 2 ,
 wherein the compound represented by Chemical Formula 3 is represented by Chemical Formula 6:   
       
         
           
           
               
               
           
         
         in Chemical Formula 6, R 3 , R 4 , R 5 , R 6 , R 26  to R 29 , and R 30  to R 33  are as defined in Chemical Formula 3, 
         subs is 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 —NR e R f , 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; and Sub 5  is optionally fused to a main body to which it is bonded to form a substituted or unsubstituted cyclic or a substituted or unsubstituted aryl, 
         R e  and R f  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; and R e  and R f  are optionally joined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl. 
       
     
     
         6 . The light-emitting material of  claim 5 ,
 wherein, in Chemical Formula 6, the NR 3 R 4  and NR 5 R 6  are, independently of each other, any one selected from Structural Formulas A6, A8, A9, and A10:   
       
         
           
           
               
               
           
         
         in Structural Formulas A6, A8, A9, and A10, 
         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; and Sub 1  and Sub 2  are, independently 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, 
         R c  and R d  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 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; and R c  and R d  are optionally joined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl. 
       
     
     
         7 . The light-emitting material of  claim 2 ,
 wherein, the compound represented by Chemical Formula 2 is represented by any one of Chemical Formulas 7 to 10:   
       
         
           
           
               
               
           
         
         in the Chemical Formulas 7 to 10, R 17 , R 18 , and R 22  to R 25  are as defined in the Chemical Formula 2, 
         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; and Sub 1  and Sub 2  are, independently 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, 
         R c  and R d  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 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; and R c  and R d  are optionally joined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl. 
       
     
     
         8 . The light-emitting material of  claim 2 ,
 wherein, the compound represented by Chemical Formula 3 is represented by Chemical Formula 11:   
       
         
           
           
               
               
           
         
         in the Chemical Formula 11, 
         R 19 , and R 26  to R 33  are as defined in the Chemical Formula 3, 
         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; and Sub 1  and Sub 2  are, independently 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, 
         R c  and R d  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 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; and R c  and R d  are optionally joined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl. 
       
     
     
         9 . The light-emitting material of  claim 2 ,
 wherein the compound represented by Chemical Formula 4 is represented by Chemical Formula 12;   
       
         
           
           
               
               
           
         
         in the Chemical Formula 12, 
         R 34  to R 45  are as defined in the above Chemical Formula 4, 
         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; and Sub 1  and Sub 2  are, independently 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, 
         R c  and R d  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 aralkyl group, or a substituted or unsubstituted C3-C30 heteroaryl group; and R c  and R d  are optionally joined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl. 
       
     
     
         10 . The light-emitting material of  claim 2 ,
 wherein the light-emitting material represented by Chemical Formula 2 is represented by any one of Compounds 1 to 66:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         11 . The light-emitting material of  claim 2 ,
 wherein the light-emitting material represented by Chemical Formula 3 is represented by any one of Compounds 67 to 82:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         12 . The light-emitting material of  claim 2 ,
 wherein the light-emitting material represented by Chemical Formula 4 is represented by any one of Compounds 83 to 92:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         13 . The light-emitting material of  claim 2 ,
 wherein —NR 1 R 2 , —NR 3 R 4 , —NR 5 R 6 , —NR 7 R 8 , —NR 9 R 10 , and —NR 11 R 12  in Chemical Formulas 2 to 4 are, independently of each other, 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, 
         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. 
       
     
     
         14 . The light-emitting material of  claim 2 ,
 wherein the triazine group in Chemical Formula 2 is the same as any one of 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; and Sub 5  and Sub 6  are, independently 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. 
       
     
     
         15 . The light-emitting material of  claim 2 ,
 wherein the triazine group in Chemical Formula 3 is any one of Structural Formulas B28 to B49:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         in Structural Formulas B28 to B49, 
         R 11  and R 12  independently represent hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group. 
       
     
     
         16 . 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 at least one selected from the hole transporting layer, the light emitting layer and the electron transporting layer comprises the compound of  claim 1 .   
     
     
         17 . The organic light emitting diode of  claim 16 ,
 wherein the light emitting layer comprises a host material and a dopant material, and   the dopant material comprises the compound of  claim 1 .   
     
     
         18 . The organic light emitting diode of  claim 17 ,
 wherein the dopant material is a delayed fluorescent light emitting material.