Organic electroluminescent compounds and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to organic electroluminescent compounds and an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present disclosure may be comprised in a light-emitting layer or an electron buffer layer, and is effective to produce an organic electroluminescent device having low driving voltage, excellent current and power efficiencies, and significantly improved operative lifespan.

1 . An organic electroluminescent compound represented by the following formula 1: 
       
         
           
           
               
               
           
         
         wherein 
         X 1  represents —N═, —NR 7 —, —O—, or —S—; 
         Y 1  represents —N═, —NR 8 —, —O—, or —S—; 
         with the provisos that when X 1  represents —N═, then Y 1  represents —NR 8 —, —O—, or —S—, and when X 1  represents —NR 7 —, then Y 1  represents —N═, —O—, or —S—, with the provisos that X 1  and Y 1  are not simultaneously —O—; X 1  and Y 1  are not simultaneously —S—; X 1  and Y 1  are not —O— and —S—, respectively; and X 1  and Y 1  are not —S— and —O—, respectively; 
         R 1  represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; 
         R 2  to R 4 , R 7 , and R 8 , 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, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; 
         a represents 1; b and c, each independently, represent 1 or 2; d represents an integer of 1 to 4; and 
         the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P. 
       
     
     
         2 . The organic electroluminescent compound according to  claim 1 , wherein formula 1 is represented by the following formula 2: 
       
         
           
           
               
               
           
         
         wherein 
         L 1  represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; 
         X 2  to X 4 , each independently, represent —N— or —CR 9 —; 
         Ar 1  and Ar 2 , each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; 
         R 9  has the same definition as R 2  to R 4 ; 
         e represents an integer of 1 to 3; and 
         X 1 , Y 1 , R 1  to R 4 , a, b, and c are as defined in  claim 1 . 
       
     
     
         3 . The organic electroluminescent compound according to  claim 1 , wherein formula 1 is represented by the following formula 3: 
       
         
           
           
               
               
           
         
         wherein 
         L 1  represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; 
         Z represents a single bond, or a substituted or unsubstituted (C1-C6)alkylene; 
         R 5  and R 6 , each independently, have the same definition as R 2  to R 4 ; 
         n represents 0 or 1; e represents an integer of 1 to 3; f and g, each independently, represent an integer of 1 to 4; and 
         X 1 , Y 1 , R 1  to R 4 , a, b and c are as defined in  claim 1 . 
       
     
     
         4 . The organic electroluminescent compound according to  claim 1 , wherein formula 1 is represented by the following formula 4: 
       
         
           
           
               
               
           
         
         wherein 
         L 1  represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; 
         Z represents a single bond, or a substituted or unsubstituted (C1-C6)alkylene; 
         W represents —NR 10 —, —O—, —S—, or —CR 11 R 12 —; 
         R 10  represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; 
         R 11  and R 12 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; 
         R 5  and R 6 , each independently, have the same definition as R 2  to R 4 ; 
         n represents 0 or 1; e and h, each independently, represent an integer of 1 to 3; g represents an integer of 1 to 4; and 
         X 1 , Y 1 , R 1  to R 4 , a, b and c are as defined in  claim 1 . 
       
     
     
         5 . The organic electroluminescent compound according to  claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         6 . An organic electroluminescent device comprising the organic electroluminescent compound according to  claim 1  as a host material.