Organic electroluminescent element and electronic device

Abstract

An organic electroluminescence device includes: an anode; an emitting layer; and a cathode, the emitting layer containing a first material, a second material and a third material, the first material being a fluorescent material, the second material being a delayed fluorescent material, the third material having a singlet energy larger than a singlet energy of the second material.

1 : An organic electroluminescence device comprising:
 an anode;   an emitting layer; and   a cathode, the emitting layer comprising a first material, a second material and a third material, wherein   the first material is a fluorescent material,   the second material is a delayed fluorescent material, and   the third material has a singlet energy larger than a singlet energy of the second material and includes at least one group selected from the group consisting of a group of formula (30b-1), a group of formula (30c-1), a group of formula (30d-1), a group of formula (30e-1), a group of formula (30e-2), a group of formula (30g), a group of formula (30h), and a group of formula (30i),   
       
         
           
           
               
               
           
         
         wherein 
         X 31 , X 34  and X 36  each independently represent a nitrogen atom or CR 31 ; 
         Y 31 , Y 32  and Y 35  to Y 38  each independently represent a nitrogen atom, CR 32  or a carbon atom bonded to another atom in the molecule of the third material; 
         R 31  and R 32  each independently represent a hydrogen atom or a substituent, the substituent being selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted diaryl phosphine oxide group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; 
         Y 39  represents NR 33 , an oxygen atom or a sulfur atom, R 33  being a substituent that is selected from the group consisting of a cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; 
         Z 31  is an oxygen atom, sulfur atom or CR 51 R 52    
         X 34  and Y 32  are optionally cross-linked via an oxygen atom, sulfur atom or CR 53 R 54 ; 
         R 51  to R 54  each independently represent the same as R 33  being the substituent; and 
         a wavy line shows a bonding position with another atom or another structure in the molecule of the third material, 
       
       
         
           
           
               
               
           
         
         wherein 
         X 31 , X 34  and X 36  each independently represent a nitrogen atom or CR 31 ; 
         Y 31 , Y 32 , Y 35 , Y 37  and Y 38  each independently represent a nitrogen atom or CR 32 ; 
         Y 41  to Y 45 , Y 47  and Y 48  each independently represent a nitrogen atom, CR 34  or a carbon atom bonded to another atom in the molecule of the third material; 
         R 31 , R 32  and R 34  each independently represent a hydrogen atom or a substituent, the substituent being selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted diaryl phosphine oxide group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; 
         Y 39  represents NR 33 , an oxygen atom or a sulfur atom; 
         Y 49  represents NR 35 , an oxygen atom or a sulfur atom; 
         R 33  and R 35  each independently represent a substituent that is selected from the group consisting of a cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; 
         Z 32  is an oxygen atom, sulfur atom or CR 51 R52; 
         X 34  and Y 32  are optionally cross-linked via an oxygen atom, sulfur atom or CR 53 R 54 ; 
         R 51  to R 4  each independently represent the same as R 33  and R 35  each being the substituent; and
 a wavy line(s) shows a bonding position with another atom or another structure in the molecule of the third material, 
 
       
       
         
           
           
               
               
           
         
         
           wherein 
         
         X 31 , X 34  and X 36  each independently represent a nitrogen atom or CR 31 ; 
         X 43 , X 44  and X 45  each independently represent a nitrogen atom or CR 36 ; 
         R 31  and R 36  each independently represent a substituent that is selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted diaryl phosphine oxide group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; 
         Z 33  is an oxygen atom, sulfur atom or CR 55 R 56 ; 
         X 34  and X 45  are optionally cross-linked via an oxygen atom, sulfur atom or CR 57 R 58 ; 
         R 55  to R 58  each independently represent a substituent that is selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring, and 
         a wavy line(s) shows a bonding position with another atom or another structure in the molecule of the third material, 
       
       
         
           
           
               
               
           
         
         wherein 
         X 31 , X 32 , X 34  and X 36  each independently represent a nitrogen atom or CR 31 ; 
         X 43 , X 44  and X 45  each independently represent a nitrogen atom or CR 36 ; 
         Y 31  to Y 35 , Y 37  and Y 38  each independently represent a nitrogen atom, CR 32  or a carbon atom bonded to another atom in the molecule of the third material; 
         Z 34  is an oxygen atom, sulfur atom or CR 55 R 56 ; 
         Z 35  is an oxygen atom, sulfur atom or CR 59 R 60 ; 
         R 31 , R 32  and R 36  each independently represent a hydrogen atom or a substituent, the substituent being selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted diaryl phosphine oxide group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; Y 39  is NR 33 , an oxygen atom or a sulfur atom: 
         R 33  is a substituent that is selected from the group consisting of a cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; 
         X 34  and X 45  are optionally cross-linked via an oxygen atom, sulfur atom or CR 57 R 58 ; 
         X 43  and Y 35  are optionally cross-linked via an oxygen atom, sulfur atom or CR 61 R 62 ; and R 55  to R 62  each independently represent the same as R 33  being the substituent; and. 
         a wavy line(s) shows a bonding position with another atom or another structure in the molecule of the third material, 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein 
         X 31 , X 32 , X 34  and X 36  each independently represent a nitrogen atom or CR 31 ; 
         Y 31  to Y 38 , Y 41  to Y 48  and Y 51  to Y 58  each independently represent a nitrogen atom, CR 37  or a carbon atom bonded to another atom in the molecule of the third material; 
         R 31  and R 37  each independently represent a hydrogen atom or a substituent, the substituent being selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted diaryl phosphine oxide group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; 
         Y 39  represents NR 33 , an oxygen atom or a sulfur atom, 
         R 33  being a substituent that is selected from the group consisting of a cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; 
         Y 49  and Y 59  each independently represent NR 38 , an oxygen atom or a sulfur atom, R 38  being each independently a hydrogen atom or a substituent, the substituent being selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms being a non-fused ring; and 
         a wavy line shows a bonding position with another atom or another structure in the molecule of the third material. 
       
     
     
         2 : The organic electroluminescence device according to  claim 1 , wherein Y 39  and Y 49  are each independently an oxygen atom or a sulfur atom. 
     
     
         3 : The organic electroluminescence device according to  claim 1 , wherein
 R 31  is a hydrogen atom or a substituent, the substituent being selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.   
     
     
         4 : The organic electroluminescence device according to  claim 1 , wherein
 R 31  is a hydrogen atom, cyano group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.   
     
     
         5 : The organic electroluminescence device according to  claim 1 , wherein
 X 31 , X 32 , X 34  and X 36  are each independently CR 31 .   
     
     
         6 : The organic electroluminescence device according to  claim 1 , wherein
 R 32  is a hydrogen atom or a substituent, the substituent being selected from the group consisting of a halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.   
     
     
         7 : The organic electroluminescence device according to  claim 1 , wherein
 R 32  is a hydrogen atom or substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.   
     
     
         8 : The organic electroluminescence device according to  claim 1 , wherein
 Y 31  to Y 31  are each independently CR 32 .   
     
     
         9 : The organic electroluminescence device according to  claim 1 , wherein the third material is an aromatic hydrocarbon compound. 
     
     
         10 : The organic electroluminescence device according to  claim 1 , wherein the third material is an aromatic heterocyclic compound. 
     
     
         11 : The organic electroluminescence device according to  claim 1 , wherein
 a singlet energy EgS(M2) of the second material is larger than a singlet energy EgS(M1) of the first material.   
     
     
         12 : The organic electroluminescence device according to  claim 1 , wherein
 an energy gap Eg 77K (M2) at 77 K of the second material is larger than an energy gap Eg 77K (M1) at 77K of the first material, and an energy gap Eg 77K (M3) at 77 K of the third material is larger than the energy gap Eg 77K (M2) at 77 K of the second material.   
     
     
         13 : The organic electroluminescence device according to  claim 1 , wherein
 a difference ΔST(M2) between a singlet energy EgS(M2) of the second material and an energy gap Eg 77K (M2) at 77 K of the second material satisfies a relationship of a numerical formula (Numerical Formula 1) below,
   Δ ST ( M 2)= EgS ( M 2)− Eg   77K ( M 2)<0.3 [eV]  Numerical Formula 1.
 
   
     
     
         14 : The organic electroluminescence device according to  claim 1 , wherein
 a difference ΔST(M3) between a singlet energy EgS(M3) of the third material and an energy gap Eg 77K (M3) at 77 K of the third material satisfies a relationship of numerical formula (Numerical Formula 3) below,
   Δ ST ( M 3)= EgS ( M 3)− Eg   77K ( M 3)>0.3 [eV]  Numerical Formula 3.
 
   
     
     
         15 : The organic electroluminescence device according to  claim 1 , wherein an energy gap Eg 77K (M3) at 77K of the third material is 2.9 eV or more. 
     
     
         16 : The organic electroluminescence device according to  claim 1 , wherein
 an ionization potential Ip(M3) of the third material and an ionization potential Ip(M2) of the second material preferably satisfy a relationship of a numerical formula (Numerical Formula 4) below:
     Ip ( M 3)≥ Ip ( M 2)  (Numerical Formula 4).
 
   
     
     
         17 : The organic electroluminescence device according to  claim 1 , wherein an ionization potential Ip(M3) of the third material is 6.3 eV or more. 
     
     
         18 : The organic electroluminescence device according to  claim 1 , wherein an electron affinity Af(M3) of the third material is 2.8 eV or more. 
     
     
         19 : The organic electroluminescence device according to  claim 1 , wherein
 a difference ΔST(M1) between a singlet energy EgS(M1) of the first material and an energy gap Eg 77K (M1) at 77 K of the first material satisfies a relationship of a numerical formula (Numerical Formula 2) below:
   Δ ST ( M 1)= EgS ( M 1)− Eg   77K ( M 1)>0.3 [eV]  Numerical Formula 2.
 
   
     
     
         20 : The organic electroluminescence device according to  claim 1 , wherein the emitting layer comprises no phosphorescent metal complex. 
     
     
         21 : The organic electroluminescence device according to  claim 1 , wherein the first material emits a fluorescent light with a main peak wavelength of 550 nm or less. 
     
     
         22 : The organic electroluminescence device according to  claim 1 , wherein the first material emits a fluorescent light with a main peak wavelength of 480 nm or less. 
     
     
         23 : The organic electroluminescence device according to  claim 1 , wherein
 the first material is at least one compound selected from the group consisting of a pyrene derivative, an aminoanthracene derivative, an aminochrysene derivative, an aminopyrene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative and a styrylamine derivative.   
     
     
         24 : An electronic device comprising the organic electroluminescence device according to  claim 1 .