Organic electroluminescence device and display

Abstract

In an organic electroluminescence device including a cathode and an anode, at least an emitting layer and an electron transporting layer are provided between the cathode and the anode. The emitting layer contains a host material formed of a naphthacene derivative represented by the following formula (1) and a dopant material formed of a compound having a pyrromethene skeleton represented by the following formula (2) or a metal complex of the compound. The electron transporting layer is preferably a benzoimidazole derivative.

1 - 20 . (canceled) 
     
     
         21 . An organic electroluminescence device, comprising:
 a cathode;   an anode; and   an emitting layer provided between the cathode and the anode, wherein   the emitting layer comprises a host and a dopant,   the host is a naphthacene derivative represented by a formula (1) as follows, and   the dopant is a compound having a pyrromethene skeleton represented by a formula (2) as follows or a metal complex of the compound,   
       
         
           
           
               
               
           
         
         in the formula (1), Q 10 , Q 40 , Q 50 , Q 60 , Q 70 , Q 80 , Q 110 , Q 120 , Q 130  and Q 140  each representing a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group, Q 10 , Q 40 , Q 50 , Q 60 , Q 70 , Q 80 , Q 110 , Q 120 , Q 130  and Q 140  being allowed to be mutually the same or different, 
         Q 20  and Q 30  in the formula (1) each representing a substituted or unsubstituted heterocylic group, Q 20  and Q 30  being allowed to be mutually the same or different, 
         in the formula (2): at least one of R 15  to R 21  being a substitute containing an aromatic ring or forming a condensed ring with an adjacent substituent while the rest of R 15  to R 21  each representing a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, a halogen, a haloalkane, a haloalkene, a haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group, the rest of R 5  to R 21  each being allowed to form a condensed ring or an aliphatic ring with an adjacent substituent, the groups listed above each having 1 to 20 carbon atoms, R 15  to R 21  being allowed to be mutually the same or different and being allowed to be substituted or unsubstituted; X representing a carbon atom or a nitrogen atom on a condition that R 21  above does not exist when X represents a nitrogen atom; and a metal in the metal complex is at least one metal selected from the group consisting of boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc and platinum. 
       
     
     
         22 . The organic electroluminescence device according to  claim 21 , wherein
 the substituted or unsubstituted heterocyclic group represented by Q 20  and Q 30  is a condensed polycyclic aromatic heterocyclic group having 2 to 20 carbon atoms.   
     
     
         23 . The organic electroluminescence device according to  claim 21 , wherein
 the heterocyclic group represented by Q 20  and Q 30  comprises a substituent, the substituent forming a condensed ring, and   the condensed ring is substituted or unsubstituted.   
     
     
         24 . The organic electroluminescence device according to  claim 21 , wherein
 the substituted or unsubstituted heterocyclic group represented by Q 20  and Q 30  is at least one substituted or unsubstituted condensed polycyclic aromatic heterocyclic group selected from the group consisting of quinoline, isoquinoline, quinoxaline, phenazine, acridine, indole, carbazole, phenoxazine, phenothiazine, benzothiazole, benzothiophen, benzofuran, acridone, benzoimidazole, coumarin and flavone.   
     
     
         25 . The organic electroluminescence device according to  claim 21 , wherein
 the metal complex represented by the formula (2) is a metal complex having a pyrromethene skeleton represented by a formula (2-1) as follows,   
       
         
           
           
               
               
           
         
         where: at least one of R 22  to R 28  is a substituent having an aromatic ring or forms a condensed aromatic ring together with an adjacent substituent while the rest of R 22  to R 28  each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkene, haloalkene, haloalkyne, a cyan group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group, the rest of R 22  to R 28  each being allowed to form a condensed ring or an aliphatic ring with an adjacent substituent, R 22  to R 28  being allowed to be mutually the same or different and being allowed to be substituted or unsubstituted; R 29  and R 30  are allowed to be mutually the same or different and each are selected from the group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group; and X representing a carbon atom or a nitrogen atom on a condition that R 21  above does not exist when X represents a nitrogen atom. 
       
     
     
         26 . The organic electroluminescence device according to  claim 25 , wherein
 at least one of R 22  to R 28  in the metal complex having the pyrromethene skeleton represented by the formula (2-1) is a substituent having an aromatic ring.   
     
     
         27 . The organic electroluminescence device according to  claim 25 , wherein
 at least one of R 22  to R 28  in the metal complex having the pyrromethene skeleton represented by the formula (2-1) forms a condensed aromatic ring together with an adjacent substituent.   
     
     
         28 . The organic electroluminescence device according to  claim 21 , wherein
 at least one of Q 10  and Q 40  in the naphthacene derivative represented by the formula (1) is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.   
     
     
         29 . The organic electroluminescence device according to  claim 21 , wherein
 the dopant is contained in the emitting layer at a doping concentration of 0.1 to 10 mass %.   
     
     
         30 . The organic electroluminescence device according to  claim 29 , wherein
 the dopant is contained in the emitting layer at a doping concentration of 0.5 to 2 mass %.   
     
     
         31 . The organic electroluminescence device according to  claim 21 , further comprising:
 an electron transporting layer provided between the cathode and the anode, wherein the electron transporting layer comprises a compound represented by a formula (4) as follows,
   (A) m -(B) n   (4)
 
   where: A represents a substituted or unsubstituted condensed aromatic hydrocarbon group having three or more rings; B represents a substituted or unsubstituted heterocyclic group; and m and n each represent an integer in a range of 1 to 6.   
     
     
         32 . The organic electroluminescence device according to  claim 31 , wherein
 A in the compound represented by the formula (4) has a skeleton in its molecule, the skeleton selected from the group consisting of anthracene, phenanthrene, naphthacene, pyrene, chrysene, benzoanthracene, pentacene, dibenzoanthracene, benzopyrene, fluorene, benzofluorene, fluoranthene, benzofluoranthene, naphthofluoranthene, dibenzofluorene, dibenzopyrene and dibenzofluoranthene.   
     
     
         33 . The organic electroluminescence device according to  claim 31 , wherein
 B in the compound represented by the formula (4) is a nitrogen-containing heterocyclic group.   
     
     
         34 . The organic electroluminescence device according to  claim 33 , wherein
 B in the compound represented by the formula (4) has a skeleton in its molecule, the skeleton selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinoxaline, acridine, imidazopyridine, imidazopyrimidine, phenanthroline, pyrazole, imidazole and benzoimidazole.   
     
     
         35 . The organic electroluminescence device according to  claim 34 ,
 wherein the compound represented by the formula (4) is a benzoimidazole derivative represented by a formula (5) or a formula (6) as follows,   
       
         
           
           
               
               
           
         
         where: R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; p represents an integer in a range of 1 to 4; R 11  represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms; R 12  represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; L represents a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted quinolinylene group or a substituted or unsubstituted fluorenylene group; and Ar 1  represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group or a substituted or unsubstituted quinolyl group, at least one of R, R 11 , R 12 , L and Ar 1  corresponding to A in the compound represented by the formula (4) and being a condensed aromatic hydrocarbon group having three or more rings. 
       
     
     
         36 . The organic electroluminescence device according to  claim 21 , wherein
 the emitting layer emits light of orange to red.   
     
     
         37 . A display, comprising the organic electroluminescence device according to  claim 21 .