Material for organic electroluminescence devices and organic electroluminescence device using the material

Abstract

A material for organic electroluminescence devices comprising a compound in which a heterocyclic group having nitrogen is bonded to an arylcarbazolyl group or a carbazolylalkylene group and an organic electroluminescence device comprising an anode, a cathode and an organic thin film layer comprising at least one layer and disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises the material for organic electroluminescence devices described above. The material can provide an organic electroluminescence device emitting bluish light with a high purity of color. The organic electroluminescence device uses the material.

1 - 18 . (canceled) 
     
     
         19 . A material for organic electroluminescence devices which comprises a compound represented by formula (1) or (2):
   (Cz-) n A  (1)
     Cz(-A) m   (2)
   wherein Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylalkylene group;   A represents a group represented by formula (A):
   (M) p -(L) q -(M′) r   (A)
 
   wherein M and M′ may be the same or different and each independently represent an unsubstituted imidazole ring or a substituted or unsubstituted nitrogen-containing heteroaromatic ring, the nitrogen-containing heteroaromatic ring being selected from the group consisting of a pyrazine ring, an aziridine ring, an azaindolizine ring, an indolizine ring, an indole ring, an isoindole ring, an indazole ring, a purine ring, a pteridine ring, a β-carboline ring, a naphthyridine ring, a quinoxaline ring, a terpyridine ring, a bipyridine ring, an acridine ring, a phenanthroline ring, a phenazine ring, and an imidazopyridine ring,   L represents a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms,   p represents an integer of 0 to 2,   q represents an integer of 1 or 2,   r represents an integer of 0 to 2, and   p+r represents an integer of 1 or greater;   n and m each represent an integer of 1 to 3; and   the substituent for each of Cz, M, and M′ is at least one group selected from the group consisting of a halogen atom, a carbazole group, a hydroxyl group, a substituted amino group, an unsubstituted amino group, a nitro group, a cyano group, a silyl group, a trifluoromethyl group, a carbonyl group, a carboxyl group, a substituted alkyl group, an unsubstituted alkyl group, a substituted alkenyl group, an unsubstituted alkenyl group, a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, an unsubstituted aromatic heterocyclic group, a substituted aralkyl group, an unsubstituted aralkyl group, a substituted aryloxy group, an unsubstituted aryloxy group, a substituted alkyloxyl group, and an unsubstituted alkyloxyl group.   
     
     
         20 . (canceled) 
     
     
         21 . The material for organic electroluminescence devices according to  claim 19 , wherein formula (1) or (2) is represented by: 
       
         
           
           
               
               
           
         
         wherein Cz and A are as defined above. 
       
     
     
         22 . The material for organic electroluminescence devices according to  claim 19 , wherein the arylcarbazolyl group is bonded to A via the aryl portion of the arylcarbazolyl group or via the carbazolyl portion of the arylcarbazolyl group. 
     
     
         23 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer comprising at least one layer and disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises a material for organic electroluminescence devices described in  claim 19 . 
     
     
         24 . The organic electroluminescence device according to  claim 23 , wherein the organic thin film layer comprises a light emitting layer and the light emitting layer comprises the material for organic electroluminescence devices. 
     
     
         25 . The organic electroluminescence device according to  claim 23 , wherein the organic thin film layer comprises a light emitting layer, the light emitting layer comprises an organic host material, and the organic host material comprises the material for organic electroluminescence devices. 
     
     
         26 . The organic electroluminescence device according to  claim 23 , wherein the organic thin film layer comprises en electron transporting layer and the electron transporting layer comprises the material for organic electroluminescence devices. 
     
     
         27 . A material for organic electroluminescence devices which comprises a compound represented by formula (1) or (2):
   (Cz-) n A  (1)
     Cz(-A) m   (2)
   wherein Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylalkylene group;   A represents a group represented by formula (A):
   (M) p -(L) q -(M′) r   (A)
 
   wherein M and M′ may be the same or different and each independently represent a substituted imidazole ring or a substituted or unsubstituted triazine ring,   L represents a single bond, a substituted or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or an unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms,   p represents an integer of 0 to 2,   q represents an integer of 1 or 2,   r represents an integer of 0 to 2, and   p+r represents an integer of 1 or greater;   n and m each represent 2 or 3; and   the substituent for each of Cz, M, and M′ is at least one group selected from the group consisting of a halogen atom, a carbazole group, a hydroxyl group, a substituted amino group, an unsubstituted amino group, a nitro group, a cyano group, a silyl group, a trifluoromethyl group, a carbonyl group, a carboxyl group, a substituted alkyl group, an unsubstituted alkyl group, a substituted alkenyl group, an unsubstituted alkenyl group, a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, an unsubstituted aromatic heterocyclic group, a substituted aralkyl group, an unsubstituted aralkyl group, a substituted aryloxy group, an unsubstituted aryloxy group, a substituted alkyloxyl group, and an unsubstituted alkyloxyl group.   
     
     
         28 . The material for organic electroluminescence devices according to  claim 27 , wherein formula (1) or (2) is represented by: 
       
         
           
           
               
               
           
         
         wherein Cz and A are as defined above. 
       
     
     
         29 . The material for organic electroluminescence devices according to  claim 27 , wherein the arylcarbazolyl group is bonded to A via the aryl portion of the arylcarbazolyl group or via the carbazolyl portion of the arylcarbazolyl group. 
     
     
         30 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer comprising at least one layer and disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises a material for organic electroluminescence devices described in  claim 27 . 
     
     
         31 . The organic electroluminescence device according to  claim 30 , wherein the organic thin film layer comprises a light emitting layer and the light emitting layer comprises the material for organic electroluminescence devices. 
     
     
         32 . The organic electroluminescence device according to  claim 30 , wherein the organic thin film layer comprises a light emitting layer, the light emitting layer comprises an organic host material, and the organic host material comprises the material for organic electroluminescence devices. 
     
     
         33 . The organic electroluminescence device according to  claim 30 , wherein the organic thin film layer comprises en electron transporting layer and the electron transporting layer comprises the material for organic electroluminescence devices. 
     
     
         34 . A material for organic electroluminescence devices which comprises a compound represented by formula (1) or (2):
   (Cz-) n A  (1)
     Cz(-A) m   (2)
   wherein Cz represents a substituted arylcarbazolyl group or a substituted or unsubstituted carbazolylalkylene group;   A represents a group represented by formula (A):
   (M) p -(L) q -(M′) r   (A)
 
   wherein M and M′ may be the same or different and each independently represent a substituted or unsubstituted pyridine ring,   L represents a single bond, a substituted or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or an unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms,   p represents an integer of 0 to 2,   q represents an integer of 1 or 2,   r represents an integer of 0 to 2, and   p+r represents an integer of 1 or greater;   n represents 3 and m represents 2 or 3; and   the substituent for each of Cz, M, and M′ is at least one group selected from the group consisting of a halogen atom, a carbazole group, a hydroxyl group, a substituted amino group, an unsubstituted amino group, a nitro group, a cyano group, a silyl group, a trifluoromethyl group, a carbonyl group, a carboxyl group, a substituted alkyl group, an unsubstituted alkyl group, a substituted alkenyl group, an unsubstituted alkenyl group, a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, an unsubstituted aromatic heterocyclic group, a substituted aralkyl group, an unsubstituted aralkyl group, a substituted aryloxy group, an unsubstituted aryloxy group, a substituted alkyloxyl group, and an unsubstituted alkyloxyl group.   
     
     
         35 . The material for organic electroluminescence devices according to  claim 34 , wherein formula (1) or (2) is represented by: 
       
         
           
           
               
               
           
         
         wherein Cz and A are as defined above. 
       
     
     
         36 . The material for organic electroluminescence devices according to  claim 34 , wherein the arylcarbazolyl group is bonded to A via the aryl portion of the arylcarbazolyl group or via the carbazolyl portion of the arylcarbazolyl group. 
     
     
         37 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer comprising at least one layer and disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises a material for organic electroluminescence devices described in  claim 34 . 
     
     
         38 . The organic electroluminescence device according to  claim 37 , wherein the organic thin film layer comprises a light emitting layer and the light emitting layer comprises the material for organic electroluminescence devices. 
     
     
         39 . The organic electroluminescence device according to  claim 37 , wherein the organic thin film layer comprises a light emitting layer, the light emitting layer comprises an organic host material, and the organic host material comprises the material for organic electroluminescence devices. 
     
     
         40 . The organic electroluminescence device according to  claim 37 , wherein the organic thin film layer comprises en electron transporting layer and the electron transporting layer comprises the material for organic electroluminescence devices. 
     
     
         41 . A material for organic electroluminescence devices which comprises a compound represented by formula (1) or (2):
   (Cz-) n A  (1)
     Cz(-A) m   (2)
   wherein Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylalkylene group, wherein the arylcarbazolyl group is bonded to A via a m-phenylene group in the aryl portion of the arylcarbazolyl group or via the carbazolyl portion of the arylcarbazolyl group;   A represents a group represented by formula (A):
   (M) p -(L) q -(M′) r   (A)
 
   wherein M and M′ may be the same or different and each independently represent a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted triazine ring, or a substituted imidazole ring,   L represents a single bond, a substituted or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or an unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms,   p represents an integer of 0 to 2,   q represents an integer of 1 or 2,   r represents an integer of 0 to 2, and   p+r represents an integer of 1 or greater;   n and m each represent an integer of 1 to 3; and   the substituent for each of Cz, M, and M′ is at least one group selected from the group consisting of a halogen atom, a carbazole group, a hydroxyl group, a substituted amino group, an unsubstituted amino group, a nitro group, a cyano group, a silyl group, a trifluoromethyl group, a carbonyl group, a carboxyl group, a substituted alkyl group, an unsubstituted alkyl group, a substituted alkenyl group, an unsubstituted alkenyl group, a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic heterocyclic group, an unsubstituted aromatic heterocyclic group, a substituted aralkyl group, an unsubstituted aralkyl group, a substituted aryloxy group, an unsubstituted aryloxy group, a substituted alkyloxyl group, and an unsubstituted alkyloxyl group.   
     
     
         42 . The material for organic electroluminescence devices according to  claim 41 , wherein formula (1) or (2) is represented by: 
       
         
           
           
               
               
           
         
         wherein Cz and A are as defined above. 
       
     
     
         43 . An organic electroluminescence device comprising an anode, a cathode and an organic thin film layer comprising at least one layer and disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises a material for organic electroluminescence devices described in  claim 41 . 
     
     
         44 . The organic electroluminescence device according to  claim 43 , wherein the organic thin film layer comprises a light emitting layer and the light emitting layer comprises the material for organic electroluminescence devices. 
     
     
         45 . The organic electroluminescence device according to  claim 43 , wherein the organic thin film layer comprises a light emitting layer, the light emitting layer comprises an organic host material, and the organic host material comprises the material for organic electroluminescence devices. 
     
     
         46 . The organic electroluminescence device according to  claim 43 , wherein the organic thin film layer comprises en electron transporting layer and the electron transporting layer comprises the material for organic electroluminescence devices.