Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent device with improved driving voltage and/or power efficiency can be provided by using the organic electroluminescent compound according to the present disclosure.

1 . An organic electroluminescent compound represented by the following formula 1: 
       
         
           
           
               
               
           
         
         wherein 
         R 3  to R 6  each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, or the group represented by the following formula A; 
       
       
         
           
           
               
               
           
         
         at least two of R 3  to R 6  each independently are represented by formula A, with a proviso that both R 3  and R 6  are not simultaneously represented by formula A; 
         L′ each independently represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene; 
         Ar′ and Ar″ each independently represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s); 
         R 1  and R 2  each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, or -L 3 -N—(Ar 5 )(Ar 6 ); or may be linked to an adjacent substituent to form a ring; 
         L 3  each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; 
         Ar 5  and Ar 6  each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; 
         a is an integer of 1 to 4, b is 1 or 2, and when a and b are each an integer of 2 or more, each of R 1  and R 2  may be the same or different from each other; and 
         when there are a plurality of substituents represented by the same symbol, each of the substituents represented by the same symbol may be the same or different from each other. 
       
     
     
         2 . The organic electroluminescent compound according to  claim 1 , wherein the substituents of the substituted alkyl, the substituted alkylene, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkylene, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring of an aliphatic ring(s) and an aromatic ring(s) each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a phosphine oxide; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (5- to 50-membered)heteroaryl unsubstituted or substituted with at least one of a (C1-C30)alkyl(s), a (C6-C30)aryl(s), and a di(C6-C30)arylamino(s); a (C6-C30)aryl unsubstituted or substituted with at least one of a (C1-C30)alkyl(s), a (3- to 50-membered)heteroaryl(s), and a mono- or di- (C6-C30)arylamino(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C2-C30)alkenylamino; a mono- or di- (C6-C30)arylamino unsubstituted or substituted with at least one of a (C1-C30)alkyl(s), a (5- to 30-membered)heteroaryl(s), and a di(C6-C30)arylamino(s); a mono- or di- (3- to 30-membered)heteroarylamino; a (C1-C30)alkyl(C2-C30)alkenylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkyl(3- to 30-membered)heteroarylamino; a (C2-C30)alkenyl(C6-C30)arylamino; a (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; a (C6-C30)aryl(3- to 30-membered)heteroarylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a (C6-C30)arylphosphine; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl. 
     
     
         3 . The organic electroluminescent compound according to  claim 1 , wherein formula 1 is represented by the following formula 1-1 or 1-2: 
       
         
           
           
               
               
           
         
         wherein 
         L 1  and L 2  each independently are as L′ defined in  claim 1 ; 
         Ar 1  to Ar 2  each independently are as Ar′ and Ar″ defined in  claim 1 ; 
         R 7  is as R 1  and R 2  defined in  claim 1 ; 
         c is 1 or 2, wherein in the case where c is 2, each R 7  may be the same of different from each other; and 
         R 1 , R 2 , a, and b are as defined in  claim 1 . 
       
     
     
         4 . The organic electroluminescent compound according to  claim 1 , wherein R 3  to R 6 , which are not represented by formula A, represent hydrogen;
 L′ each independently represents a single bond, or a substituted or unsubstituted (C6-C12)arylene;   Ar′ and Ar″ each independently represent a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or a substituted or unsubstituted fused ring of a (C3-C10)aliphatic ring(s) and a (C6-C15)aromatic ring(s);   R 1  and R 2  each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (5- to 15-membered)heteroaryl, or -L 3 -N—(Ar 5 )(Ar 6 );   L 3  each independently represents a single bond; and   Ar 5  and Ar 6  each independently represent a substituted or unsubstituted (C6-C12)aryl.   
     
     
         5 . The organic electroluminescent compound according to  claim 1 , wherein R 3  to R 6 , which are not represented by formula A, represent hydrogen;
 L′ each independently represents a single bond, or a substituted or unsubstituted (C6-C12)arylene;   Ar′ and Ar″ each independently represent a (C6-C25)aryl unsubstituted or substituted with at least one of a (C1-C6)alkyl(s) and a (C6-C12)aryl(s); a (5- to 20-membered)heteroaryl unsubstituted or substituted with at least one (C6-C12)aryl(s); or a fused ring of a (C3-C10)aliphatic ring(s) and a (C6-C15)aromatic ring(s) unsubstituted or substituted with at least one (C1-C6)alkyl(s);   R 1  and R 2  each independently represent hydrogen; a (C6-C15)aryl unsubstituted or substituted with at least one (C1-C6)alkyl(s); a (5- to 15-membered)heteroaryl unsubstituted or substituted with at least one (C6-C12)aryl(s); or -L 3 -N—(Ar 5 )(Ar 6 );   L 3  each independently represents a single bond; and   Ar 5  and Ar 6  each independently represent an unsubstituted (C6-C12)aryl.   
     
     
         6 . The organic electroluminescent compound according to  claim 1 , wherein the compound represented by formula 1 is selected from the following compounds: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         7 . An organic electroluminescent material comprising the organic electroluminescent compound according to  claim 1 . 
     
     
         8 . An organic electroluminescent device comprising the organic electroluminescent compound according to  claim 1 . 
     
     
         9 . The organic electroluminescent device according to  claim 8 , wherein the organic electroluminescent compound is comprised in a hole transport zone.