Anthracene derivative and organic electroluminescence device using the derivative

Abstract

An anthracene derivative represented by general formula (I): wherein X and Y represent a trifunctional aromatic ring group or the like, (1) A 1 to A 4 represent an aryl group or a monovalent heterocyclic group or (2) A 1 and A 3 represent hydrogen atom and A 2 and A 4 represent a styryl group in which the phenyl portion may be substituted and the α-position or the β-position of the vinyl portion may be substituted with an alkyl group, R 1 to R 16 represent hydrogen atom, a halogen atom, cyano group, nitro group, alkyl group or the like, Q represents an arylene group or the like and p represents 0, 1 or 2; and an organic electroluminescence device which comprises at least an organic light emitting layer disposed between a pair of electrodes and the above anthracene derivative. The novel anthracene derivative exhibits a high efficiency of light emission and excellent heat resistance when the derivative is used as a material constituting an organic electroluminescence device.

1 . An anthracene derivative represented by general formula (I):  
       
         
           
           
               
               
           
         
       
       wherein X and Y each independently represent a substituted or unsubstituted trifunctional aromatic ring group having 6 to 30 carbon atoms or a substituted or unsubstituted trifunctional heterocyclic group having 4 to 30 carbon atoms; (1) A 1  to A 4  each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 4 to 30 carbon atoms or (2) A 1  represents hydrogen atom, A 2  represents a styryl group in which a phenyl portion may be substituted and an α-position or a β-position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms, A 3  represents hydrogen atom and A 4  represents a styryl group in which a phenyl portion may be substituted and an α-position or a β-position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms; R 1  to R 16  each independently represent hydrogen atom, a halogen atom, cyano group, nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group or a substituted or unsubstituted aryl group; adjacent groups represented by R 1  to R 16  may for rings by forming bonds between each other; Q represents a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 4 to 30 carbon atoms; and p represents a number selected from 0, 1 and 2.  
     
     
         2 . An anthracene derivative represented by general formula (II):  
       
         
           
           
               
               
           
         
       
       wherein (1) A 1  to A 4  each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 4 to 30 carbon atoms or (2) A 1  represents hydrogen atom, A 2  represents a styryl group in which a phenyl portion may be substituted and an α-position or a β-position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms, A 3  represents hydrogen atom and A 4  represents a styryl group in which a phenyl portion may be substituted and an α-position or a β-position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms; R 1  to R 16  each independently represent hydrogen atom, a halogen atom, cyano group, nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group or a substituted or unsubstituted aryl group; adjacent groups represented by R 1  to R 16  may for rings by forming bonds between each other; Q represents a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 4 to 30 carbon atoms; and p represents a number selected from 0, 1 and 2.  
     
     
         3 . An anthracene derivative represented by general formula (II′):  
       
         
           
           
               
               
           
         
       
       wherein (1) A 1  to A 4  each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 4 to 30 carbon atoms or (2) A 1  represents hydrogen atom, A 2  represents a styryl group in which a phenyl portion may be substituted and an α-position or a β-position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms, A 3  represents hydrogen atom and A 4  represents a styryl group in which a phenyl portion may be substituted and an α-position or a β-position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms; R 1  to R 16  each independently represent hydrogen atom, a halogen atom, cyano group, nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group or a substituted or unsubstituted aryl group; adjacent groups represented by R 1  to R 16  may for rings by forming bonds between each other; Q represents a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 4 to 30 carbon atoms; and p represents a number selected from 0, 1 and 2.  
     
     
         4 . An anthracene derivative represented by general formula (III):  
       
         
           
           
               
               
           
         
       
       wherein X and Y each independently represent a substituted or unsubstituted trifunctional aromatic ring group having 6 to 30 carbon atoms or a substituted or unsubstituted trifunctional heterocyclic group having 4 to 30 carbon atoms; R 1  to R 20  each independently represent hydrogen atom, a halogen atom, cyano group, nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group or a substituted or unsubstituted aryl group; adjacent groups represented by R 1  to R 20  may for rings by forming bonds between each other; Q represents a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 4 to 30 carbon atoms; and p represents a number selected from 0, 1 and 2.  
     
     
         5 . An organic electroluminescence device which comprises a light emitting area comprising an anthracene derivative described in  claim 1 .  
     
     
         6 . An organic electroluminescence device which comprises an organic light emitting layer comprising an anthracene derivative described in  claim 1 .  
     
     
         7 . An organic electroluminescence device according to  claim 5 , wherein the organic light emitting layer further comprises a substance forming a recombination site.  
     
     
         8 . An organic electroluminescence device according to  claim 6 , wherein the organic light emitting layer further comprises a substance forming a recombination site.  
     
     
         9 . An organic electroluminescence device according to  claim 7 , wherein the substance forming a recombination site is a fluorescent substance having a quantum yield of fluorescence of 0.3 to 1.0.  
     
     
         10 . An organic electroluminescence device according to  claim 8 , wherein the substance forming a recombination site is a fluorescent substance having a quantum yield of fluorescence of 0.3 to 1.0.  
     
     
         11 . An organic electroluminescence device according to  claim 7 , wherein the substance forming a recombination site is at least one compound selected from styrylamine compounds, quinacridone derivatives, rubrene derivatives, coumarine derivatives, perylene derivatives, pyrane derivatives and fluoranthene derivatives.  
     
     
         12 . An organic electroluminescence device according to  claim 8 , wherein the substance forming a recombination site is at least one compound selected from styrylamine compounds, quinacridone derivatives, rubrene derivatives, coumarine derivatives, perylene derivatives, pyrane derivatives and fluoranthene derivatives.  
     
     
         13 . An organic electroluminescence device according to  claim 5 , wherein a layer of a chalcogenide, a layer of a metal halide or a layer of a metal oxide is formed between the organic light emitting layer and a cathode or an anode.  
     
     
         14 . An organic electroluminescence device according to  claim 6 , wherein a layer of a chalcogenide, a layer of a metal halide or a layer of a metal oxide is formed between the organic light emitting layer and a cathode or an anode.