Organic electroluminescent element, material for organic electroluminescent element, and ligth emitting device, display device and lighting device each using organic electroluminescent element

Abstract

An organic electroluminescent element which has a substrate, a pair of electrodes disposed on this substrate and composed of an anode and a cathode, and at least one organic layer disposed between these electrodes and including a light-emitting layer, and in which a compound expressed by General Formula 1-1 is contained in at least one layer of the aforementioned light-emitting layer(s) exhibits high luminous efficiency, excellent blue color purity, and little change in chromaticity accompanying drive deterioration. (R 1 to R 10 [each] represent a hydrogen atom or a substituent, and at least one of R 1 to R 10 is a substituent expressed by General Formula 1-2; however, a pyrene skeleton is never contained in R 1 to R 10 ; the asterisk indicates the bonding position with a pyrene ring; X 1 to X 5 [each] represent a carbon atom or a nitrogen atom, and at least one of X 1 to X 5 is a nitrogen atom; R 11 to R 15 [each] represent a hydrogen atom or a substituent, and at least one of R 11 to R 15 is an alkyl group or a silyl group; however, if X 1 to X 5 represent nitrogen atoms, there is no R 11 to R 15 bonded on these nitrogen atoms.)

1 . An organic electroluminescent element having
 a substrate,   a pair of electrodes disposed on this substrate and composed of an anode and a cathode, and   at least one organic layer disposed between these electrodes and including a light-emitting layer, wherein   a compound expressed by General Formula 1-1 below is contained in at least one layer of said light-emitting layer(s):   
       
         
           
           
               
               
           
         
       
       R 1  to R 10  each independently represents a hydrogen atom or a substituent, and at least one of R 1  to R 10  is a substituent expressed by General Formula 1-2 below; however, a pyrene skeleton is never contained in R 1  to R 10 : 
       
         
           
           
               
               
           
         
       
       wherein the asterisk indicates a bonding position with a pyrene ring; X 1  to X 5  each independently represents a carbon atom or a nitrogen atom, and at least one of X 1  to X 5  is a nitrogen atom; R 11  to R 15  each independently represents a hydrogen atom or a substituent, and at least one of R 11  to R 15  represents an alkyl group or a silyl group; however, if X 1  to X 5  represent nitrogen atoms, there is no R 11  to R 15  bonded on these nitrogen atoms. 
     
     
         2 . The organic electroluminescent element according to  claim 1 , wherein R 1  to R 10  in General Formula 1-1 above do not jointly form a ring. 
     
     
         3 . The organic electroluminescent element according to  claim 1 , wherein the compound expressed by General Formula 1-1 above is expressed by General Formula 2 below: 
       
         
           
           
               
               
           
         
       
       R 2  to R 10  each independently represents a hydrogen atom or a substituent; X 1 , X 3 , and X 5  each independently represents a carbon atom or a nitrogen atom, and at least one of X 1 , X 3 , and X 5  is a nitrogen atom; R 11  to R 15  each independently represents a hydrogen atom or a substituent, and at least one of R 11  to R 15  represents an alkyl group or a silyl group, but if X 1 , X 3 , and X 5  represent nitrogen atoms, there is no R 11 , R 13 , or R 15  bonded on these nitrogen atoms; however, a pyrene skeleton is never contained in R 2  to R 15 , and even when R 11  to R 15  jointly form a ring, a pyrene skeleton is never formed. 
     
     
         4 . The organic electroluminescent element according to  claim 1 , wherein R 12  and/or R 14  in General Formula 1-1 above is an alkyl group or a silyl group. 
     
     
         5 . The organic electroluminescent element according to  claim 1 , wherein both R 12  and R 14  in General Formula 1-1 above are an alkyl group or a silyl group. 
     
     
         6 . The organic electroluminescent element according to  claim 1 , wherein the compound expressed by General Formula 1-1 above is expressed by any of General Formulas 3-1 to 3-3 below: 
       
         
           
           
               
               
           
         
       
       R 2  to R 10  represent each independently a hydrogen atom or a substituent; X 1 , X 3 , and X 5  represent each independently a carbon atom or a nitrogen atom, and at least one of X 1 , X 3 , and X 5  is a nitrogen atom; R 11  to R 15  represent each independently a hydrogen atom or a substituent, and at least one of R 11  to R 15  represents an alkyl group or a silyl group; at least one of X 6  to X 8  is a nitrogen atom; R 16  to R 20  represent each independently a hydrogen atom or a substituent, and at least one of R 16  to R 20  represents an alkyl group or a silyl group, but if X 1 , X 3 , X 5 , and X 6  to X 8  represent nitrogen atoms, there is no R 11 , R 13 , R 15 , R 16 , R 18 , or R 20  bonded on these nitrogen atoms; however, a pyrene skeleton is never contained in R 2  to R 20 , and even when R 11  to R 15  jointly form a ring, or even when R 16  to R 20  jointly form a ring, a pyrene skeleton is never formed. 
     
     
         7 . The organic electroluminescent element according to  claim 6 , wherein R 11  to R 20  in General Formulas 3-1 to 3-3 above represent each independently a hydrogen atom, an alkyl group, or a silyl group. 
     
     
         8 . The organic electroluminescent element according to  claim 6  or  7 , wherein at least two of X 1 , X 3 , and X 5  or at least two of X 6  to X 8  in General Formulas 3-1 to 3-3 above are nitrogen atoms. 
     
     
         9 . The organic electroluminescent element according to  claim 1 , wherein at least one of R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10  in General Formula 1-1 above is a substituent. 
     
     
         10 . The organic electroluminescent element according to  claim 1 , wherein at least one of R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10  in General Formula 1-1 above, General Formula 2 above, and General Formulas 3-1 to 3-3 above is a substituent from among an alkyl group, a silyl group, an amino group, a fluorine atom, and a phenyl group or pyridyl group that has been substituted with at least one of these groups. 
     
     
         11 . The organic electroluminescent element according to  claim 1 , wherein at least one of R 2  to R 10  in General Formula 1-1 above, General Formula 2 above, and General Formulas 3-1 to 3-3 above is an ortho-alkyl-substituted phenyl group. 
     
     
         12 . The organic electroluminescent element according to  claim 11 , wherein said ortho-alkyl-substituted phenyl group is an o-tolyl group, a 2,6-xylyl group, or a mesityl group. 
     
     
         13 . The organic electroluminescent element according to  claim 1 , wherein R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10  in General Formula 1-1 above are each an alkyl group, a silyl group, an amino group, a fluorine atom, a phenyl group or pyridyl group that has been substituted with at least one of these groups, or a hydrogen atom. 
     
     
         14 . The organic electroluminescent element according to  claim 1 , wherein the molecular weight of the compound expressed by General Formula 1-1 above is 1000 or less. 
     
     
         15 . The organic electroluminescent element according to  claim 1 , wherein the compound expressed by General Formula 1-1 above is a light-emitting material. 
     
     
         16 . The organic electroluminescent element according to  claim 1 , wherein said light-emitting layer includes an anthracene-based host material. 
     
     
         17 . A light-emitting device which makes use of the organic electroluminescent element according to  claim 1 . 
     
     
         18 . A display device which makes use of the organic electroluminescent element according to  claim 1 . 
     
     
         19 . A lighting device which makes use of the organic electroluminescent element according to  claim 1 . 
     
     
         20 . A material for an organic electroluminescent element composed of a compound expressed by General Formula 1-1 below: 
       
         
           
           
               
               
           
         
       
       R 1  to R 10  represent each independently a hydrogen atom or a substituent, and at least one of R 1  to R 10  is a substituent expressed by General Formula 1-2 below; however, a pyrene skeleton is never contained in R 1  to R 10 . 
       
         
           
           
               
               
           
         
       
       the asterisk indicates the bonding position with a pyrene ring; X 1  to X 5  represent each independently a carbon atom or a nitrogen atom, and at least one of X 1  to X 5  is a nitrogen atom; R 11  to R 15  represent each independently a hydrogen atom or a substituent, and at least one of R 11  to R 15  represents an alkyl group or a silyl group; however, if X 1  to X 5  represent nitrogen atoms, there is no R 11  to R 15  bonded on these nitrogen atoms. 
     
     
         21 . The material for an organic electroluminescent element according to  claim 20 , wherein R 1  to R 10  in General Formula 1-1 above do not jointly form a ring. 
     
     
         22 . The material for an organic electroluminescent element according to  claim 20 , wherein the compound expressed by General Formula 1-1 above is expressed by General Formula 2 below: 
       
         
           
           
               
               
           
         
       
       R 2  to R 10  represent each independently a hydrogen atom or a substituent; X 1 , X 3 , and X 5  represent each independently a carbon atom or a nitrogen atom, and at least one of X 1 , X 3 , and X 5  is a nitrogen atom; R 11  to R 15  represent each independently a hydrogen atom or a substituent, and at least one of R 11  to R 15  represents an alkyl group or a silyl group, but if X 1 , X 3 , and X 5  represent nitrogen atoms, there is no R 11 , R 13 , or R 15  bonded on these nitrogen atoms; however, a pyrene skeleton is never contained in R 2  to R 15 , and even when R 11  to R 15  jointly form a ring, a pyrene skeleton is never formed. 
     
     
         23 . The material for an organic electroluminescent element according to  claim 20 , wherein R 12  and/or R 14  in General Formula 1-1 above is an alkyl group or a silyl group. 
     
     
         24 . The material for an organic electroluminescent element according to  claim 20 , wherein both R 12  and R 14  in General Formula 11 above are an alkyl group or a silyl group. 
     
     
         25 . The material for an organic electroluminescent element according to  claim 20 , wherein the compound expressed by General Formula 1-1 above is expressed by any of General Formulas 3-1 to 3-3 below: 
       
         
           
           
               
               
           
         
       
       R 2  to R 10  each independently represents a hydrogen atom or a substituent; X 1 , X 3 , and X 5  represent each independently a carbon atom or a nitrogen atom, and at least one of X 1 , X 3 , and X 5  is a nitrogen atom; R 11  to R 15  represent each independently a hydrogen atom or a substituent, and at least one of R 11  to R 15  represents an alkyl group or a silyl group; at least one of X 6  to X 8  is a nitrogen atom; R 16  to R 20  represent each independently a hydrogen atom or a substituent, and at least one of R 16  to R 20  represents an alkyl group or a silyl group, but if X 1 , X 3 , X 5 , and X 6  to X 8  represent nitrogen atoms, there is no R 11 , R 13 , R 15 , R 16 , R 18 , or R 20  bonded on these nitrogen atoms; however, a pyrene skeleton is never contained in R 2  to R 20 , and even when R 11  to R 15  jointly form a ring, or even when R 16  to R 20  jointly form a ring, a pyrene skeleton is never formed. 
     
     
         26 . The material for an organic electroluminescent element according to  claim 25 , wherein R 11  to R 20  in General Formulas 3-1 to 3-3 above each independently represents a hydrogen atom, an alkyl group, or a silyl group. 
     
     
         27 . The material for an organic electroluminescent element according to  claim 25 , wherein at least two of X 1 , X 3 , and X 5  or at least two of X 6  to X 8  in General Formulas 3-1 to 3-3 above are nitrogen atoms. 
     
     
         28 . The material for an organic electroluminescent element according to  claim 20 , wherein at least one of R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10  in General Formula 1-1 above is a substituent. 
     
     
         29 . The material for an organic electroluminescent element according to  claim 20 , wherein at least one of R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10  in General Formula 1-1 above, General Formula 2 above, and General Formulas 3-1 to 3-3 above is a substituent from among an alkyl group, a silyl group, an amino group, a fluorine groups. 
     
     
         30 . The material for an organic electroluminescent element according to  claim 20 , wherein at least one of R 2  to R 10  in General Formula 1-1 above is an ortho-alkyl-substituted phenyl group. 
     
     
         31 . The material for an organic electroluminescent element according to  claim 30 , wherein said ortho-alkyl-substituted phenyl group is an o-tolyl group, a 2,6-xylyl group, or a mesityl group. 
     
     
         32 . The material for an organic electroluminescent element according to  claim 20 , wherein R 2 , R 3 , R 4 , R 5 , R 7 , R 9 , and R 10  in General Formula 1-1 above are each an alkyl group, a silyl group, an amino group, a fluorine atom, a phenyl group or pyridyl group that has been substituted with at least one of these groups, or a hydrogen atom. 
     
     
         33 . The material for an organic electroluminescent element according to  claim 20 , wherein the molecular weight of the compound expressed by General Formula 1-1 above is 1000 or less. 
     
     
         34 . The material for an organic electroluminescent element according to  claim 20 , wherein the compound expressed by General Formula 1-1 above is a light-emitting material.