Organic el device and anthracene derivative

Abstract

An organic EL device includes: an anode for injecting holes; a phosphorescent-emitting layer; a fluorescent-emitting layer; and a cathode for injecting electrons. The phosphorescent-emitting layer contains a phosphorescent host and a phosphorescent dopant for phosphorescent emission. The fluorescent-emitting layer contains a fluorescent host and a fluorescent dopant for fluorescent emission. The fluorescent host is at least one of an asymmetric anthracene derivative represented by a formula (1) below and a pyrene derivative represented by a formula (2) below.

1 - 9 . (canceled) 
     
     
         10 . An organic EL device, comprising:
 an anode for injecting holes;   a phosphorescent-emitting layer;   a fluorescent-emitting layer; and   a cathode for injecting electrons,   the phosphorescent-emitting layer containing a phosphorescent host and a phosphorescent dopant for phosphorescent emission,   the fluorescent-emitting layer comprising a fluorescent host and a fluorescent dopant for fluorescent emission,   the fluorescent host being at least one of an asymmetric anthracene derivative represented by a formula (1) below and a pyrene derivative represented by a formula (2) below,   
       
         
           
           
               
               
           
         
       
       where: Ar 1  and Ar 2  are different groups, each independently representing a group derived from a substituted or unsubstituted aromatic ring having 6 to 20 ring carbon atoms; the aromatic ring is substituted by one or more substituent(s) or unsubstituted; the substituent(s) is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, substituted or unsubstituted arylthio group having 5 to 50 ring atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted silyl group, carboxyl group, halogen atom, cyano group, nitro group and hydroxy group; when the aromatic ring is substituted by two or more substituents, the substituents are mutually the same or different; an adjacent set of the substituents is allowed to be bonded together to form a saturated or unsaturated cyclic structure;
 R 1  to R 8  each are selected from the group consisting of a hydrogen atom, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, substituted or unsubstituted arylthio group having 5 to 50 ring atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted silyl group, carboxyl group, halogen atom, cyano group, nitro group and hydroxy group; an adjacent set of substituents is allowed to be bonded together to form a saturated or unsaturated cyclic structure, 
 
       
         
           
           
               
               
           
         
       
       where: Ar 1a  and Ar 2a  each represent a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms;
 L each represent a substituted or unsubstituted phenylene group, substituted or unsubstituted naphthalenylene group, substituted or unsubstituted fluorenylene group or substituted or unsubstituted dibenzo-sylolylene group; 
 m is an integer of 0 to 2, nb is an integer of 1 to 4, s is an integer of 0 to 2 and t is an integer of 0 to 4; 
 L or Ar 1a  is bonded to pyrene in any one of 1st to 5th positions, and L or Ar 2a  is bonded to pyrene in any one of 6th to 10th positions; 
 when nb+t is even, Ar 1a , Ar 2a  and L satisfy the following (1) or (2), (1) Ar 1a ≠Ar 2a , wherein ≠ means that Ar 1a  and Ar 2a  are group of different structures, 
 
       (2) when Ar 1a =Ar 2a ,
 (2-1) m≠s or nb≠t, or both, or 
 (2-2) when m=s and nb=t and, 
 (2-2-1) L or the pyrene is bonded in a different bonding position on Ar 1a  and Ar 2a , or 
 (2-2-2) L or the pyrene is bonded in the same bonding position on Ar 1a  and Ar 2a , 
 substituting positions of L or Ar 1a  and Ar 2a  in the pyrene are not 1st and 6th positions or 2nd and 7th positions. 
 
     
     
         11 . The organic EL device according to  claim 10 , wherein, in place of the asymmetric anthracene derivative, a benzanthracene derivative represented by a formula (3) below is used as the fluorescent host, 
       
         
           
           
               
               
           
         
       
       where: Ar 1  and Ar 2  each independently represent a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms;
 R 1  to R 12  each are independently selected from the group consisting of a hydrogen atom, substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring carbon atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, substituted or unsubstituted arylthio group having 5 to 50 ring atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted silyl group, carboxyl group, halogen atom, cyano group, nitro group and hydroxyl group; 
 Ar 1 , Ar 2 , R 11  and R 12  each are allowed to be plural; and an adjacent set thereof is allowed to form a saturated or unsaturated cyclic structure. 
 
     
     
         12 . The organic EL device according to  claim 10 , wherein the phosphorescent dopant comprises a metal complex comprising: a metal selected from the group consisting of Ir, Pt, Os, Au, Cu, Re and Ru; and a ligand. 
     
     
         13 . The organic EL device according  claim 10 , wherein the fluorescent dopant is an amine compound represented by a formula (4) below, 
       
         
           
           
               
               
           
         
       
       where: P represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 40 ring atoms, or a substituted or unsubstituted styryl group; k is an integer of 1 to 3;
 Ar 1  to Ar 4  each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 40 ring atoms; s is an integer of 0 to 4; 
 an adjacent set of substituents for suitably-selected two of Ar 1 , Ar 4  and P is allowed to be bonded together to form a ring; and when k is 2 or more, P are mutually the same or different. 
 
     
     
         14 . The organic EL device according to  claim 10 , wherein the fluorescent dopant is a fluoranthene derivative represented by any one of formulae (5) to (8) below, 
       
         
           
           
               
               
           
         
       
       where: X 1  to X 52  each independently represent a hydrogen atom, halogen atom, substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkenyloxy group having 2 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkenylthio group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aralkyloxy group having 7 to 30 carbon atoms, substituted or unsubstituted aralkylthio group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, substituted or unsubstituted arylthio having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 2 to 30 carbon atoms, cyano group, silyl group, hydroxyl group, —COOR 1e  group wherein R 1e  represents a hydrogen atom, substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms or substituted or unsubstituted aryl group having 6 to 30 carbon atoms, —COR 2e  group wherein R 2e  represents a hydrogen atom, substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms or amino group, or —OCOR 3e  group wherein R 3e  represents a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or substituted or unsubstituted aryl group having 6 to 30 carbon atoms; an adjacent set of groups of X 1  to X 52  and an adjacent set of substituents of X 1  to X 52  are allowed be bonded together to form a substituted or unsubstituted carbocycle. 
     
     
         15 . The organic EL device according to  claim 10 , wherein the fluorescent dopant is represented by a formula (9) below, 
       
         
           
           
               
               
           
         
       
       where: A and A′ each represent an independent azine ring system corresponding to a six-membered aromatic ring containing one nitrogen or more;
 X a  and X b  represent independently-selected substituents capable of being bonded together to form a fused ring with respect to A or A′; 
 m and n each independently represent an integer of 0 to 4; 
 Z a  and Z b  represent independently-selected substituents; and 
 1, 2, 3, 4, 1′, 2′, 3′ and 4′ are each independently selected from a carbon atom and nitrogen atom. 
 
     
     
         16 . The organic EL device according to  claim 10 , wherein
 a wavelength of emission of the fluorescent-emitting layer is shorter than a wavelength of emission of the phosphorescent-emitting layer,   the fluorescent-emitting layer provides emission at a wavelength of 410 to 580 nm, and   the phosphorescent-emitting layer provides emission at a wavelength of 500 to 700 nm.   
     
     
         17 . The organic EL device according to  claim 16 , wherein the phosphorescent-emitting layer provides emission at a wavelength of 600 to 700 nm. 
     
     
         18 . The organic EL device according to  claim 17 , wherein the fluorescent-emitting layer is a blue emitting layer, and the phosphorescent-emitting layer is a red phosphorescent-emitting layer for providing red emission.