Organic electroluminescent device
View Patent ↗Provided is a practically useful organic EL element having high efficiency and high driving stability while being capable of being driven at a low voltage. The organic EL element has a light-emitting layer and any other organic layer between an anode and a cathode opposite to each other. The light-emitting layer contains at least two host materials and at least one light-emitting dopant. At least one of the host materials is a host material selected from compounds each having one or two indolocarbazole skeletons, and at least one of the other host materials is a host material selected from carbazole compounds each substituted with a dibenzofuran or a dibenzothiophene.
1. An organic electroluminescent element, comprising one or more light-emitting layers between an anode and a cathode opposite to each other, wherein:
at least one of the one or more light-emitting layers contains at least two host materials and at least one light-emitting dopant; and
the at least two host materials comprise a material selected from compounds each represented by any one of the following general formulae (1) and (2), and a material selected from compounds each represented by the following general formula (3):
where:
a ring a, a ring c, and a ring c′ each independently represent an aromatic ring or heterocycle represented by the formula (a1) fused at arbitrary positions of two adjacent rings;
a ring b, a ring d, and a ring d′ each independently represent a heterocycle represented by the formula (b1) fused at arbitrary positions of two adjacent rings;
X 1 represents CR 7 or N;
Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 22 carbon atoms, or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms;
Z represents a divalent linking group selected from an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, and a linked aromatic group obtained by linking 2 to 10 aromatic rings of the aromatic hydrocarbon group and the aromatic heterocyclic group, and a group bonded to N comprises an aromatic hydrocarbon group having 6 to 22 carbon atoms, or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms;
R 1 to R 7 each independently represent hydrogen, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a diaralkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 22 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms;
L 1 and L 2 each independently represent an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group obtained by linking 2 to 10 aromatic rings of the aromatic hydrocarbon group and the aromatic heterocyclic group; and
p and q each represent an integer of from 0 to 7, h, i, j, k, l, and m each represent an integer of 4, n represents an integer of 2, when a plurality of L 1 's, L 2 's, R 1 's, R 2 's, R 3 's, R 4 's, R 5 's, R 6 's, or R 7 's exist, the plurality of groups may be identical to or different from each other, and the aromatic hydrocarbon group or aromatic heterocyclic group in any one of Ar 1 , Ar 2 , L 1 , L 2 , Z, and R 1 to R 7 may have a substituent, and when the group has a substituent, the substituent comprises a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a diaralkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, or an alkylsulfonyl group having 1 to 20 carbon atoms;
where L 3 's each independently represent hydrogen or a monovalent group, and E represents oxygen or sulfur, and
wherein at least one of L 3 's in the general formula (3) represents a monovalent group represented by the formula (e1):
where:
L 4 's each independently represent hydrogen, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a dialkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group obtained by linking 2 to 10 aromatic rings of the aromatic hydrocarbon group and the aromatic heterocyclic group;
X 2 's each independently represent CL 4 or nitrogen; and
the aromatic hydrocarbon group or aromatic heterocyclic group in L 4 may have a substituent, and when the group has a substituent, the substituent comprises a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a dialkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, or an alkylsulfonyl group having 1 to 20 carbon atoms.
2. An organic electroluminescent element according to claim 1 , wherein a difference (ΔEA) in electron affinity between the material selected from the compounds each represented by any one of the general formulae (1) and (2), and the material selected from the compounds each represented by the general formula (3) is more than 0.1 eV.
3. An organic electroluminescent element according to claim 1 , wherein in the general formulae (1) and (2), at least one of Ar 1 and Ar 2 represents a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, and X 1 represents CR 7 .
4. An organic electroluminescent element according to claim 1 , wherein the compounds each represented by the general formula (3) comprise compounds each represented by the general formula (4):
where X 2 , L 4 , and E are identical in meaning to X 2 , L 4 , and E in the general formula (3) and the formula (e1), respectively.
5. An organic electroluminescent element according to claim 4 , wherein the compounds each represented by the general formula (4) comprise compounds each represented by the general formula (5):
where L 4 and E are identical in meaning to L 4 and E in the general formula (4), respectively.
6. An organic electroluminescent element according to claim 1 , wherein the light-emitting dopant comprises a phosphorescent light-emitting dopant formed of an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold.
7. An organic electroluminescent element according to claim 1 , wherein in the general formulae (1) and (2), at least one of Ar 1 and Ar 2 represents a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, and X 1 represents CR 7 ; and
a difference (ΔEA) in electron affinity between the material selected from the compounds each represented by any one of the general formulae (1) and (2), and the material selected from the compounds each represented by the general formula (3) is more than 0.1 eV.
8. An organic electroluminescent element according to claim 2 ,
wherein the difference (ΔEA) is 0.2-1.5 eV.
9. An organic electroluminescent element comprising one or more light-emitting layers between an anode and a cathode opposite to each other, wherein:
at least one of the one or more light-emitting layers contains at least two host materials and at least one light-emitting dopant; and
the at least two host materials comprise a material selected from compounds each represented by any one of the following general formulae (1) and (2), and a material selected from compounds each represented by the following general formula (3):
where:
a ring a, a ring c, and a ring c′ each independently represent an aromatic ring or heterocycle represented by the formula (a1) fused at arbitrary positions of two adjacent rings;
a ring b, a ring d, and a ring d′ each independently represent a heterocycle represented by the formula (b1) fused at arbitrary positions of two adjacent rings;
X 1 represents CR 7 or N;
Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 22 carbon atoms, or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms;
Z represents a divalent linking group selected from an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, and a linked aromatic group obtained by linking 2 to 10 aromatic rings of the aromatic hydrocarbon group and the aromatic heterocyclic group, and a group bonded to N comprises an aromatic hydrocarbon group having 6 to 22 carbon atoms, or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms;
R 1 to R 7 each independently represent hydrogen, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl grout having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a diaralkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 22 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms;
L 1 and L 2 each independently represent an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group obtained by linking 2 to 10 aromatic rings of the aromatic hydrocarbon group and the aromatic heterocyclic group; and
p and q each represent an integer of from 0 to 7, h, i, i, k, l, and m each represent an integer of 4, n represents an integer of 2, when a plurality of L 1 's, L 2 's, R 1 's, R 2 's, R 3 's, R 4 's, R 5 's, R 6 's, or R 7 's exist, the plurality of groups may be identical to or different from each other, and the aromatic hydrocarbon group or aromatic heterocyclic group in any one of Ar 1 , Ar 2 , L 1 , L 2 , Z, and R 1 to R 7 may have a substituent, and when the group has a substituent, the substituent comprises a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a diaralkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, or an alkylsulfonyl group having 1 to 20 carbon atoms;
where L 3 's each independently represent hydrogen or a monovalent group, and E represents oxygen or sulfur, and
wherein the material selected from compounds each represented by the general formula (3) is selected from compounds in the group consisting of:
10. An organic electroluminescent element according to claim 9 , wherein the material selected from compounds each represented by the general formula (3) is selected from compounds in the group consisting of:
11. An organic electroluminescent element according to claim 9 , wherein the material selected from compounds each represented by the general formula (3) is selected from compounds in the group consisting of:
12. An organic electroluminescent element according to claim 9 , wherein the material selected from compounds each represented by the general formula (3) is selected from compounds in the group consisting of:
13. An organic electroluminescent element according to claim 9 , wherein the material selected from compounds each represented by the general formula (3) is selected from compounds in the group consisting of: