Indenopyridine-based compound and organic light-emitting device including the same

Abstract

Provided are an indenopyridine-based compound and an organic light-emitting device including the same. The indenopyridine-based compound is represented by Formula 1:

1 .- 20 . (canceled) 
     
     
         21 . An indenopyridine-based compound represented by Formula 1: 
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         X 1  is a nitrogen atom (N) or C(R 11 ); X 2  is N or C(R 12 ); X 3  is N or C(R 13 ); X 4  is N or C(R 14 ); wherein only one of X 1  to X 4  is N; 
         L 1  is selected from: 
         i) an anthracenylene group, a chrysenylene group, and a pyrenylene group; and 
         ii) an anthracenylene group, a chrysenylene group, and a pyrenylene group, each substituted with at least one selected from: 
         a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group; 
         a phenyl group, a naphthyl group, a pyridyl group, and a triazinyl group; and 
         a phenyl group, a naphthyl group, a pyridyl group, and a triazinyl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group; 
         n1 is 1, 2, or 3; 
         R 1  and R 2  are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxyl group, a substituted or unsubstituted C 1 -C 30  alkyl group, a substituted or unsubstituted C 2 -C 30  alkenyl group, a substituted or unsubstituted C 2 -C 30  alkynyl group, a substituted or unsubstituted C 1 -C 30  alkoxy group, a substituted or unsubstituted C 3 -C 30  cycloalkyl group and a substituted or unsubstituted C 3 -C 30  cycloalkenyl group, 
         R 11  to R 14 , R 3 , and R 4  are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxyl group, a substituted or unsubstituted C 1 -C 30  alkyl group, a substituted or unsubstituted C 2 -C 30  alkenyl group, a substituted or unsubstituted C 2 -C 30  alkynyl group, a substituted or unsubstituted C 1 -C 30  alkoxy group, a substituted or unsubstituted C 3 -C 30  cycloalkyl group, a substituted or unsubstituted C 3 -C 30  cycloalkenyl group, a substituted or unsubstituted C 6 -C 30  aryl group, a substituted or unsubstituted C 6 -C 30  aryloxy group, and a substituted or unsubstituted C 6 -C 30  arylthio group; and 
         a1 and a2 are each independently selected from an integer of 0, 1, 2 and 3. 
       
     
     
         22 . The indenopyridine-based compound as claimed in  claim 21 , wherein:
 L 1  is selected from an anthracenylene group, a chrysenylene group, and a pyrenylene group.   
     
     
         23 . The indenopyridine-based compound as claimed in  claim 21 , wherein n1 is an integer of 1 or 2. 
     
     
         24 . The indenopyridine-based compound as claimed in  claim 21 , wherein:
 a moiety represented by (L 1 ) n1  is one selected from Formulae 3-1 to 3-4:   
       
         
           
           
               
               
           
         
         wherein, in Formulae 3-1 to 3-4, 
         * is a binding site with R 4 , and 
         ** is a binding site with an indenopyridine ring portion of Formula 1. 
       
     
     
         25 . The indenopyridine-based compound as claimed in  claim 21 , wherein R 1  and R 2  are each independently selected from a hydrogen atom, a deuterium atom and a methyl group. 
     
     
         26 . The indenopyridine-based compound as claimed in  claim 21 , wherein R 11  to R 14 , and R 3  are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a nitro group, and a methyl group. 
     
     
         27 . The indenopyridine-based compound as claimed in  claim 21 , wherein:
 a2 is 1, 2, or 3, and   R 4  is selected from:   i) a phenyl group, a naphthyl group, and an anthryl group; and   ii) a phenyl group, a naphthyl group, and an anthryl group, each substituted with at least one selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, a tert-butyl group, a phenyl group, a naphthyl group, and an anthryl group.   
     
     
         28 . The indenopyridine-based compound as claimed in  claim 21 , wherein:
 a2 is 1, 2, or 3, and   R 4  is selected from a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.   
     
     
         29 . The indenopyridine-based compound as claimed in  claim 21 , wherein a2 is an integer of 0 or 1. 
     
     
         30 . The indenopyridine-based compound as claimed in  claim 21 , wherein:
 a2 is 1; and   a1 is 3.   
     
     
         31 . The indenopyridine-based compound as claimed in  claim 21 , wherein the indenopyridine-based compound is represented by Formula 1a: 
       
         
           
           
               
               
           
         
         wherein, in Formula 1a, 
         a moiety represented by (L 1 ) n1  is one selected from Formulae 3-1 to 3-4: 
       
       
         
           
           
               
               
           
         
         
           wherein, in Formulae 3-1 to 3-4, 
           * is a binding site with R 4 , and 
           ** is a binding site with an indenopyridine ring portion of Formula 1a; 
         
         R 1  and R 2  are each independently selected from a hydrogen atom, a deuterium atom and a methyl group, 
         R 3  and R 12  to R 14  are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a nitro group, and a methyl group; 
         R 4  is selected from a phenyl group, a 1-naphthyl group, and a 2-naphthyl group; 
         a1 is 3; and 
         a2 is an integer of 0 or 1. 
       
     
     
         32 . The indenopyridine-based compound as claimed in  claim 21 , wherein the indenopyridine-based compound is represented by one of Formulae 1b to 1e: 
       
         
           
           
               
               
           
         
         wherein, in Formulae 1b to 1e, 
         a moiety represented by (L 1 ) n1  is one selected from Formulae 3-1 to 3-4: 
       
       
         
           
           
               
               
           
         
         
           wherein, in Formulae 3-1 to 3-4, 
           * is a binding site with R 4 , and 
           ** is a binding site with an indenopyridine ring portion of Formulae 1b to 1e; 
         
         R 1  and R 2  are each independently selected from a hydrogen atom, a deuterium atom and a methyl group; 
         R 13  is selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a nitro group, and a methyl group; 
         R 4  is selected from a phenyl group, a 1-naphthyl group, and a 2-naphthyl group; and 
         a2 is an integer of 0 or 1. 
       
     
     
         33 . The indenopyridine-based compound as claimed in  claim 21 , wherein the indenopyridine-based compound represented by Formula 1 is one selected from Compounds 2, 4, 6, 10, 14 and 17 to 19: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         34 . An organic light-emitting device (OLED), comprising:
 a first electrode;   a second electrode facing the first electrode; and   an organic layer that is disposed between the first electrode and the second electrode and includes an emission layer,   wherein the organic layer includes at least one indenopyridine-based compound of  claim 21 .   
     
     
         35 . The OLED as claimed in  claim 34 , wherein the organic layer further includes a hole transporting region including at least one selected from a hole injection layer, a hole transport layer, a functional layer having both hole injecting and transporting capabilities, a buffer layer, and an electron blocking layer between the first electrode and the emission layer, and further includes an electron transporting region including at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer between the emission layer and the second electrode. 
     
     
         36 . The OLED as claimed in  claim 34 , wherein the emission layer includes the indenopyridine-based compound. 
     
     
         37 . The OLED as claimed in  claim 36 , wherein the emission layer further includes a dopant, and the indenopyridine-based compound serves as a host. 
     
     
         38 . The OLED as claimed in  claim 37 , wherein the dopant is an amine-based compound represented by Formula 100: 
       
         
           
           
               
               
           
         
         wherein, in Formula 100, 
         X is selected from an anthracenyl group, a chrysenyl group, a pyrenyl group, and a benzopyrenyl group; 
         Ar 101  and Ar 102  are each independently selected from 
         i) a phenyl group, a naphthyl group, and a biphenyl group; and 
         ii) a phenyl group, a naphthyl group, and a biphenyl group, each substituted with at least one of a deuterium atom, a fluorine atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, and a phenyl group; and 
         n is an integer of 2 to 4. 
       
     
     
         39 . The OLED as claimed in  claim 37 , wherein the dopant is one selected from Compounds 101 to 109: