Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device

Abstract

The present invention provides an organic compound having excellent properties, which is excellent in electron-injection/transport performance, has hole-blocking ability and is high stability in a thin-film state, as a material for an organic electroluminescence device having a high efficiency and a high durability, and provides is an organic electroluminescence device having a high efficiency and a high durability using the compound. The present invention relates to a compound having a substituted anthracene ring structure and a pyridoindole ring structure represented by general formula (1); and an organic electroluminescence device having a pair of electrodes and at least one organic layer interposed between the electrodes in which the at least one organic layer contains the compound.

1 . A compound comprising a substituted anthracene ring structure and a pyridoindole ring structure, represented by formula (1): 
       
         
           
           
               
               
           
         
       
       wherein:
 Ar 1  and Ar 2  are each independently a substituted or unsubstituted aromatic hydrocarbon group; 
 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group comprising 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; 
 W, X, Y, and Z are each a carbon atom or a nitrogen atom, provided that only one of W, X, Y, and Z is a nitrogen atoms and the nitrogen atom does not have a substituent R 1  to R 4 ; and 
 A is a divalent group of formula (A1-a): 
 
       
         
           
           
               
               
           
         
         wherein;
 n1 is 1 or 2; 
 R 9 , R 10 , and R 11  are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group comprising 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group; 
 D and E are each a carbon atom or a nitrogen atom, provided that when one or two of D and E are a nitrogen atom, the nitrogen atom does not have a substituent R 9  to R 11  or bonding group and when n1 is 2, a plurality of R 9 's, R 10 's, R 11 's, D's, and E's, may be different from each other. 
 
       
     
     
         2 . The compound of  claim 1 , wherein in formula (A1-a), n1 is 1 and at least one of D and E is a nitrogen atom. 
     
     
         3 . The compound of  claim 1 , wherein in formula (A1-a), n1 is 1 and each of D and E are nitrogen atoms. 
     
     
         4 . The compound of  claim 1 , wherein A is a divalent group of formula (A1-b): 
       
         
           
           
               
               
           
         
         wherein R 13 , R 14 , R 15 , R 16 , and R 17  are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group 
       
     
     
         5 . The compound of  claim 1 , wherein A is a divalent group of formula (A1-c): 
       
         
           
           
               
               
           
         
         wherein R 13 , R 14 , R 15 , and R 16  are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group. 
       
     
     
         6 . The compound of  claim 1 , wherein A is a divalent group of formula (A1-d): 
       
         
           
           
               
               
           
         
         wherein R 13 , R 14 , R 15 , and R 16  are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group. 
       
     
     
         7 . The compound of  claim 1 , wherein A is a divalent group of formula (A1-e): 
       
         
           
           
               
               
           
         
         wherein R 13  and R 14  are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group. 
       
     
     
         8 . An organic electroluminescence device, comprising a pair of electrodes and at least one organic layer interposed between the electrodes, wherein the organic layer comprises the compound of  claim 1 . 
     
     
         9 . The organic electroluminescence device of  claim 8 , wherein the organic layer comprises an electron-transport layer and the compound of formula (1) is present in the electron-transport layer. 
     
     
         10 . The organic electroluminescence device of  claim 8 , wherein the organic layer comprises a hole-blocking layer and the compound of formula (1) is present in the hole-blocking layer. 
     
     
         11 . The organic electroluminescence device of  claim 8 , wherein the organic layer comprises a light-emitting layer and the compound of formula (1) is present in the light-emitting layer. 
     
     
         12 . The organic electroluminescence device of  claim 8 , wherein the organic layer comprises an electron-injection layer and the compound of formula (1) is present in the electron-injection layer.