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 compound of the present disclosure has a high glass transition temperature that can be used in a deposition process. Further, by comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having a low driving voltage, high luminous efficiency, and/or improved lifespan characteristics can be provided.

1 . An organic electroluminescent compound represented by the following formula 1: 
       
         
           
           
               
               
           
         
         wherein 
         X 1  to X 3  each independently represent CH or N, with a proviso that at least one of X 1  to X 3  are N; 
         Ar 1  and Ar 2  each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; 
         Ar 3  and Ar 4  each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; 
         L 1  represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; 
         R 1  and R 2  each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; or are linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic, aromatic ring, or a combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; 
         a represents an integer of 1 to 5, and b represents an integer of 1 to 4, in which if a and b represent an integer of 2 or more, each Ar 3  and each Ar 4  may be the same or different; and 
         the heteroaryl(ene) and the heterocycloalkyl contain at least one heteroatom selected from B, N, O, S, Si, and P. 
       
     
     
         2 . The organic electroluminescent compound according to  claim 1 , wherein substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (5- to 30-membered)heteroaryl(ene), the substituted (3- to 7-membered)heterocycloalkyl, the substituted (C3-C30)cycloalkyl, and the substituted mono- or polycyclic, (C3-C30) alicyclic, aromatic ring, or a combination thereof in Ar 1  to Ar 4 , 1_1, R 1 , and R 2  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 (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with a (5- to 30-membered)heteroaryl(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-(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl(s); 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
 X 1  to X 3  each independently represent CH or N, with a proviso that at least two of X 1  to X 3  are N;   Ar 1  and Ar 2  each independently represent a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;   Ar 3  and Ar 4  each independently represent hydrogen, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;   L 1  represents a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted (5- to 20-membered)heteroarylene;   R 1  and R 2  each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl; or are linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C5-C10) alicyclic, aromatic ring, or a combination thereof; and   a and b each independently represent an integer of 1 to 2.   
     
     
         4 . The organic electroluminescent compound according to  claim 1 , wherein
 X 1  to X 3  each independently represent N;   Ar 1  and Ar 2  each independently represent a (C6-C25)aryl unsubstituted or substituted with a (C1-C6)alkyl(s) or a (C6-C12)aryl(s), or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl(s);   Ar 3  and Ar 4  each independently represent hydrogen, an unsubstituted (C6-C20)aryl, or an unsubstituted (5- to 20-membered)heteroaryl;   L 1  represents a single bond, an unsubstituted (C6-C20)arylene, or an unsubstituted (5- to 20-membered)heteroarylene;   R 1  and R 2  each independently represent an unsubstituted (C1-C6)alkyl, or an unsubstituted (C6-C12)aryl; or are linked to each other to form an unsubstituted cyclopentane ring; and   a and b each independently represent 1.   
     
     
         5 . The organic electroluminescent compound according to  claim 1 , wherein formula 1 is at least one selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         6 . An organic electroluminescent material comprising the organic electroluminescent compound according to  claim 1 . 
     
     
         7 . An organic electroluminescent device comprising the organic electroluminescent compound according to  claim 1 . 
     
     
         8 . The organic electroluminescent device according to  claim 7 , wherein the organic electroluminescent compound is comprised in at least one of an electron buffer layer and an electron transport layer. 
     
     
         9 . A display device comprising the organic electroluminescent compound according to  claim 1 .