Material for organic electroluminescent devices and organic electroluminescent devices made by using the same

Abstract

A material for electroluminescent devices which comprises a compound in which a heterocyclic group having nitrogen is bonded to carbazolyl group and an organic electroluminescent device having at least one organic thin film layer which is sandwiched between the cathode and the anode and contains the above material in at least one layer, are provided. The material can provide organic electroluminescent devices emitting bluish light with a high purity of color. The organic electroluminescence device uses the material.

The invention claimed is: 
     
       1. A compound according to formula (1):
   (Cz-) n M m    ( 1 )
 
 
       wherein:
 each Cz is independently a substituted carbazolyl group or an unsubstituted carbazolyl group; 
 each substituted carbazolyl group Cz independently comprises at least one substituent selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, and an unsubstituted aromatic heterocyclic group; 
 each M is independently a substituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted aziridine, an unsubstituted aziridine, a substituted azaindolizine, an unsubstituted azaindolizine, a substituted isoindole, an unsubstituted isoindole, a substituted indazole, an unsubstituted indazole, a substituted purine, an unsubstituted purine, a substituted pteridine, an unsubstituted pteridine, a substituted β-carboline, an unsubstituted β-carboline, a substituted quinoxaline, an unsubstituted quinoxaline, a substituted quinazoline, an unsubstituted quinazoline, a substituted phenanthroline, an unsubstituted phenanthroline, a substituted phenazine, or an unsubstituted phenazine; 
 each substituted group M independently comprises at least one substituent selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, and an unsubstituted aromatic heterocyclic group; 
 m is an integer of 1 to 3; 
 n is an integer of 1 to 3; and 
 at least one group M is bonded to at least one carbazolyl group Cz at a 9-position of the at least one carbazolyl group Cz; and 
 a triplet energy gap of the compound is 2.5 to 3.3 eV. 
 
     
     
       2. The compound according to  claim 1 , wherein the compound is a compound according to any one of formulas (2), (3), and (5) to (8): 
       
         
           
           
               
               
           
         
       
     
     
       3. An organic electroluminescence device, comprising:
 an anode; 
 a cathode; and 
 an organic thin film layer; 
 wherein: 
 the organic thin film layer is disposed between the anode and the cathode; and 
 the organic thin film layer comprises the compound according to  claim 1 . 
 
     
     
       4. The organic electroluminescence device according to  claim 3 , wherein:
 the organic thin film layer comprises a light emitting layer; and 
 the light emitting layer comprises the compound according to formula (1). 
 
     
     
       5. The organic electroluminescence device according to  claim 3 , wherein:
 the organic thin film layer comprises a light emitting layer; 
 the light emitting layer comprises a host material; and 
 the host material comprises the compound according to formula (1). 
 
     
     
       6. The organic electroluminescence device according to  claim 3 , wherein:
 the organic thin film layer comprises an electron transporting layer; and 
 the electron transporting layer comprises the compound according to formula (1). 
 
     
     
       7. The compound according to  claim 1 , wherein a singlet energy gap of the compound is 2.8 to 3.8 eV. 
     
     
       8. The compound according to  claim 1 , wherein a singlet energy gap of the compound is 2.9 to 3.6 eV. 
     
     
       9. The compound according to  claim 1 , wherein a triplet energy gap of the compound is 2.5 to 3.3 eV. 
     
     
       10. The organic electroluminescent device according to  claim 3 , wherein the organic electroluminescent device emits bluish light. 
     
     
       11. The organic electroluminescent device according to  claim 3 , wherein the organic electroluminescent device emits light by multiplet excitation to a triplet state or higher. 
     
     
       12. An organic electroluminescence device, comprising:
 an anode; 
 a cathode; and 
 an organic thin film layer; 
 wherein: 
 the organic thin film layer is disposed between the anode and the cathode; and 
 the organic thin film layer comprises a light emitting layer; 
 the light emitting layer comprises a host material; and 
 the host material comprises a compound according to formula (1):
   (Cz-) n M m    (1)
 
 
 
       wherein:
 each Cz is independently a substituted carbazolyl group or an unsubstituted carbazolyl group; 
 each substituted carbazolyl group Cz independently comprises at least one substituent selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, and an unsubstituted aromatic heterocyclic group; 
 each M is independently a substituted pyridine, an unsubstituted pyridine, a substituted pyrimidine, an unsubstituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted aziridine, an unsubstituted aziridine, a substituted azaindolizine, an unsubstituted azaindolizine, a substituted isoindole, an unsubstituted isoindole, a substituted indazole, an unsubstituted indazole, a substituted purine, an unsubstituted purine, a substituted pteridine, an unsubstituted pteridine, a substituted β-carboline, an unsubstituted β-carboline, a substituted quinoxaline, an unsubstituted quinoxaline, a substituted quinazoline, an unsubstituted quinazoline, a substituted phenanthroline, an unsubstituted phenanthroline, a substituted phenazine, or an unsubstituted phenazine; 
 each substituted group M independently comprises at least one substituent selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, and an unsubstituted aromatic heterocyclic group; 
 m is an integer of 1 to 3; 
 n is an integer of 1 to 3; and 
 at least one group M is bonded to at least one carbazolyl group Cz at a 9-position of the at least one carbazolyl group Cz. 
 
     
     
       13. The organic electroluminescence device according to  claim 12 , wherein the compound is a compound according to any one of formulas (2), (3), and (5) to (8): 
       
         
           
           
               
               
           
         
       
     
     
       14. The organic electroluminescence device according to  claim 12 , wherein:
 the organic thin film layer comprises a light emitting layer; and   the light emitting layer comprises the compound according to formula (1).   
     
     
       15. The organic electroluminescence device according to  claim 12 , wherein:
 the organic thin film layer comprises a light emitting layer;   the light emitting layer comprises a host material; and   the host material comprises the compound according to formula (1).   
     
     
       16. The organic electroluminescence device according to  claim 12 , wherein:
 the organic thin film layer comprises an electron transporting layer; and   the electron transporting layer comprises the compound according to formula (1).   
     
     
       17. The organic electroluminescence device according to  claim 12 , wherein at least one group M is a substituted pyrimidine, an unsubstituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted aziridine, an unsubstituted aziridine, a substituted azaindolizine, an unsubstituted azaindolizine, a substituted isoindole, an unsubstituted isoindole, a substituted indazole, an unsubstituted indazole, a substituted purine, an unsubstituted purine, a substituted pteridine, an unsubstituted pteridine, a substituted β-carboline, an unsubstituted β-carboline, a substituted quinoxaline, an unsubstituted quinoxaline, a substituted quinazoline, an unsubstituted quinazoline, a substituted phenanthroline, an unsubstituted phenanthroline, a substituted phenazine, or an unsubstituted phenazine. 
     
     
       18. The organic electroluminescence device according to  claim 12 , wherein a singlet energy gap of the compound is 2.8 to 3.8 eV. 
     
     
       19. The organic electroluminescence device according to  claim 12 , wherein a singlet energy gap of the compound is 2.9 to 3.6 eV. 
     
     
       20. The organic electroluminescence device according to  claim 12 , wherein a triplet energy gap of the compound is 2.5 to 3.3 eV. 
     
     
       21. The organic electroluminescent device according to  claim 12 , wherein the organic electroluminescent device emits bluish light. 
     
     
       22. The organic electroluminescent device according to  claim 12 , wherein the organic electroluminescent device emits light by multiplet excitation to a triplet state or higher. 
     
     
       23. The compound according to claim 1, wherein each M is independently a substituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted aziridine, an unsubstituted aziridine, a substituted azaindolizine, an unsubstituted azaindolizine, a substituted isoindole, an unsubstituted isoindole, a substituted indazole, an unsubstituted indazole, a substituted purine, an unsubstituted purine, a substituted pteridine, an unsubstituted pteridine, a substituted β-carboline, an unsubstituted β-carboline, a substituted quinazoline, an unsubstituted quinazoline, a substituted phenanthroline, an unsubstituted phenanthroline, a substituted phenazine, or an unsubstituted phenazine.  
     
     
       24. The compound according to claim 1, wherein each M is independently a substituted pyrimidine, a substituted pyrazine, or an unsubstituted pyrazine.  
     
     
       25. The organic electroluminescence device according to claim 3, wherein each M is independently a substituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted aziridine, an unsubstituted aziridine, a substituted azaindolizine, an unsubstituted azaindolizine, a substituted isoindole, an unsubstituted isoindole, a substituted indazole, an unsubstituted indazole, a substituted purine, an unsubstituted purine, a substituted pteridine, an unsubstituted pteridine, a substituted β-carboline, an unsubstituted β-carboline, a substituted quinazoline, an unsubstituted quinazoline, a substituted phenanthroline, an unsubstituted phenanthroline, a substituted phenazine, or an unsubstituted phenazine.  
     
     
       26. The organic electroluminescence device according to claim 3, wherein each M is independently a substituted pyrimidine, a substituted pyrazine, or an unsubstituted pyrazine.  
     
     
       27. The organic electroluminescent device according to claim 12, wherein each M is independently a substituted pyridine, an unsubstituted pyridine, a substituted pyrimidine, an unsubstituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted aziridine, an unsubstituted aziridine, a substituted azaindolizine, an unsubstituted azaindolizine, a substituted isoindole, an unsubstituted isoindole, a substituted indazole, an unsubstituted indazole, a substituted purine, an unsubstituted purine, a substituted pteridine, an unsubstituted pteridine, a substituted β-carboline, an unsubstituted β-carboline, a substituted quinazoline, an unsubstituted quinazoline, a substituted phenanthroline, an unsubstituted phenanthroline, a substituted phenazine, or an unsubstituted phenazine.  
     
     
       28. The organic electroluminescent device according to claim 12, wherein each M is independently a substituted pyridine, an unsubstituted pyridine, a substituted pyrimidine, an unsubstituted pyrimidine, a substituted pyrazine, or an unsubstituted pyrazine.  
     
     
       29. A compound according to formula (1):
   (Cz-) n M m    (1)
   wherein:   each Cz is independently a substituted carbazolyl group or an unsubstituted carbazolyl group;   each substituted carbazolyl group Cz independently comprises at least one substituent selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, and an unsubstituted aromatic heterocyclic group;   each M is independently a substituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted aziridine, an unsubstituted aziridine, a substituted azaindolizine, an unsubstituted azaindolizine, a substituted isoindole, an unsubstituted isoindole, a substituted indazole, an unsubstituted indazole, a substituted purine, an unsubstituted purine, a substituted pteridine, an unsubstituted pteridine, a substituted β-carboline, an unsubstituted β-carboline, a substituted quinoxaline, an unsubstituted quinoxaline, a substituted quinazoline, an unsubstituted quinazoline, a substituted phenanthroline, an unsubstituted phenanthroline, a substituted phenazine, or an unsubstituted phenazine;   each substituted group M independently comprises at least one substituent selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, and an unsubstituted aromatic heterocyclic group;   m is an integer of 1 to 3;   n is an integer of 1 to 3;   at least one group M is bonded to at least one carbazolyl group Cz at a 9-position of the at least one carbazolyl group Cz; and   a singlet energy gap of the compound is 2.8 to 3.8 eV.    
     
     
       30. The compound according to claim 29, wherein the compound is a compound according to any one of formulas (2), (3), and (5) to (8):  
       
         
           
           
               
               
           
         
       
     
     
       31. The compound according to claim 29, wherein each M is independently a substituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted aziridine, an unsubstituted aziridine, a substituted azaindolizine, an unsubstituted azaindolizine, a substituted isoindole, an unsubstituted isoindole, a substituted indazole, an unsubstituted indazole, a substituted purine, an unsubstituted purine, a substituted pteridine, an unsubstituted pteridine, a substituted β-carboline, an unsubstituted β -carboline, a substituted quinazoline, an unsubstituted quinazoline, a substituted phenanthroline, an unsubstituted phenanthroline, a substituted phenazine, or an unsubstituted phenazine.  
     
     
       32. The compound according to claim 29, wherein each M is independently a substituted pyrimidine, a substituted pyrazine, or an unsubstituted pyrazine.  
     
     
       33. The compound according to claim 1, wherein each M is independently a substituted pyrimidine, a substituted pyrazine, an unsubstituted pyrazine, a substituted quinazoline, or an unsubstituted quinazoline.