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. By using the organic electroluminescent compound of the present disclosure, it is possible to provide an organic electroluminescent device having low driving voltage and/or excellent power efficiency and/or improved driving lifespan.

1 . An organic electroluminescent compound represented by the following formula 1: 
       
         
           
           
               
               
           
         
         wherein 
         X represents O or S; 
         L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; 
         Ar represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or −NR 11 R 12 ; 
         R 1  to R 3 , each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2  and R 3 , respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; 
         R 11  to R 14 , each independently, represent a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; 
         n represents 1 or 2; where if n represents 2, each Ar may be the same or different; 
         a and b, each independently, represent an integer of 1 to 3; c represents an integer of 1 to 4; where if a to c, each independently, represent an integer of 2 or more, each of R 1  to R 3  may be the same or different; and 
         the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P. 
       
     
     
         2 . The organic electroluminescent compound according to  claim 1 , wherein the substituents of the substituted aryl(ene), the substituted heteroaryl(ene), the substituted alkyl, and the substituted mono- or polycyclic, alicyclic or aromatic ring, or the combination thereof, in L, Ar, R 1  to R 3 , and R 11  to R 14 , each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; 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 (C 3 -C30)cycloalkyl; a (C 3 -C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C1-C30)alkyl or a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (3- to 30-membered)heteroaryl; 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- (C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; 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
 L represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene;   Ar represents a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or —NR 11 R 12 ;   R 1  to R 3 , each independently, represent hydrogen, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2  and R 3 , respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;   R 11  to R 14 , each independently, represent a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl; and   a to c, each independently, represent 1 or 2.   
     
     
         4 . The organic electroluminescent compound according to  claim 1 , wherein
 L represents a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene;   Ar represents a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or —NR 11 R 12 ;   R 1  to R 3 , each independently, represent hydrogen, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2  and R 3 , respectively, to form an unsubstituted, mono- or polycyclic, (C5-C18) aromatic ring;   R 11  to R 14 , each independently, represent a substituted or unsubstituted (C6-C18)aryl; and   a to c, each independently, represent 1 or 2.   
     
     
         5 . The organic electroluminescent compound according to  claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         6 . A host material comprising the organic electroluminescent compound according to  claim 1 . 
     
     
         7 . An electron buffer 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 device comprises at least one light-emitting layer disposed between a first electrode and a second electrode, wherein the light-emitting layer comprises a host and a dopant, wherein the host comprises a plurality of host compounds, and wherein at least one host compound of the plurality of host compounds is the organic electroluminescent compound. 
     
     
         10 . The organic electroluminescent device according to  claim 8 , wherein the organic electroluminescent device comprises a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode; and an electron transport layer and an electron buffer layer between the light-emitting layer and the second electrode, and wherein the electron buffer layer comprises the organic electroluminescent compound.