Material for organic electroluminescent elements, and organic electroluminescent element using same
View Patent ↗Disclosed are an organic electroluminescent device (organic EL device) having improved luminous efficiency, sufficiently secured driving stability, and a simple construction, and a material for an organic EL device. The material for an organic EL device includes a carborane compound having a structure in which at least one carborane ring and at least one dibenzothiophene ring are present, and the at least one carborane ring is bonded to the at least one dibenzothiophene ring at position 1, 2, or 3. In addition, the organic EL device includes, between an anode and a cathode laminated on a substrate, at least one organic layer, in which the at least one organic layer includes the carborane compound.
1. A material for an organic electroluminescent device, comprising a carborane compound represented by the general formula (1), (2), or (3):
wherein,
a ring A represents a divalent carborane group C 2 B 10 H 10 represented by the formula (1a) or the formula (1b), and when a plurality of rings A are present in a molecule thereof, the rings may be identical to or different from each other;
r represents a number of repetitions and represents an integer of 0;
L 1 and L 2 each represent a divalent substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a divalent substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, or a divalent linked aromatic group formed by linking 2 to 6 aromatic groups selected from the aromatic hydrocarbon groups or the aromatic heterocyclic groups, terminal L 1 and L 2 may each represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and when L 1 and L 2 each represent the linked aromatic group, the group may be linear or branched, and aromatic rings to be linked may be identical to or different from each other;
L 3 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, a linked aromatic group formed by linking 2 to 6 aromatic groups selected from the substituted or unsubstituted aromatic hydrocarbon groups and the substituted or unsubstituted aromatic heterocyclic groups, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, and when L 3 represents the linked aromatic group, the group may be linear or branched, and aromatic rings to be linked may be identical to or different from each other;
wherein when the aromatic group in each of L 1 to L 3 has a substituent, the substituent is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an acetyl group, the aromatic group may have a plurality of substituents, and the plurality of substituents may be identical to or different from each other; and
wherein, in each of the general formulae (1) to (3), at least one of L 1 to L 3 is a carbazolyl (Cz) group or a Cz containing group.
2. The material for an organic electroluminescent device according to claim 1 , wherein, in each of the general formulae (1) to (3), the ring A represents a divalent carborane group C 2 B 10 H 8 represented by the formula (1a).
3. The material for an organic electroluminescent device according to claim 1 , wherein, in each of the general formulae (1) to (3), L 1 to L 3 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups selected from the aromatic hydrocarbon groups and the aromatic heterocyclic groups.
4. The material for an organic electroluminescent device according to claim 1 , wherein, in each of the general formulae (1) to (3), L 1 to L 3 each independently represent a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups selected from the aromatic heterocyclic groups.
5. The material for an organic electroluminescent device according to claim 1 , wherein, the carborane compound has one dibenzothiophene (DBT) group or DBT containing group.
6. The material for an organic electroluminescent device according to claim 1 , wherein, in each of the general formulae (1) to (3), L 1 to L 2 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups selected from the aromatic hydrocarbon groups and the aromatic heterocyclic group, and L 3 represent hydrogen, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups selected from the aromatic hydrocarbon groups and the aromatic heterocyclic group.
7. The material for an organic electroluminescent device according to claim 6 , wherein,
the substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms is selected from groups each produced by removing a hydrogen atom from an aromatic hydrocarbon compound of benzene, naphthalene, fluorene, anthracene, phenanthrene, triphenylene, fluoranthene, pyrene, or chrysene,
the substituted or unsubstituted aromatic heterocyclic group is selected from groups each produced by removing a hydrogen atom from an aromatic heterocyclic compound of pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, naphthyridine, carbazole, acridine, azepine, tribenzazepine, phenazine, phenoxazine, phenothiazine, dibenzophosphole, or dibenzoborole,
the linked aromatic groups each produced by removing a hydrogen atom from biphenyl, terphenyl, phenylnaphthalene, diphenylnaphthalene, phenylanthracene, diphenylanthracene, diphenylfluorene, bipyridine, bipyrimidine, bitriazine, biscarbazole, phenylpyridine, phenylpyrimidine, phenyltriazine, phenylcarbazole, diphenylpyridine, diphenyltriazine, or bis(carbazolyl)benzene, and
the aromatic hydrocarbon group, the aromatic heterocyclic group, or the linked aromatic group may have a substituent, the substituent is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an acetyl group, and the alkyl group and the alkoxy group may be linear, branched, or cyclic.
8. The material for an organic electroluminescent device according to claim 1 , wherein, in each of the general formulae (1) to (3), L 3 represents a hydrogen atom.
9. An organic electroluminescent device having a structure in which an anode, at least one organic layer, and a cathode are laminated on a substrate, wherein the at least one organic layer comprises an organic layer containing the material for an organic electroluminescent device of claim 1 .
10. The organic electroluminescent device according to claim 9 , wherein the organic layer containing the material for an organic electroluminescent device comprises at least one layer selected from the group consisting of a light-emitting layer, an electron-transporting layer, and a hole-blocking layer.
11. The organic electroluminescent device according to claim 9 , wherein the organic layer containing the material for an organic electroluminescent device comprises a light-emitting layer containing a phosphorescent light-emitting dopant.
12. The organic electroluminescent device according to claim 11 , wherein an emission wavelength of the phosphorescent light-emitting dopant has an emission maximum wavelength at 550 nm or less.
13. A material for an organic electroluminescent device, comprising a carborane compound represented by the general formula (1), (2), or (3):
wherein,
a ring A represents a divalent carborane group C 2 B 10 H 10 represented by the formula (1a) or the formula (1 b), and when a plurality of rings A are present in a molecule thereof, the rings may be identical to or different from each other;
r represents a number of repetitions and represents an integer of 0 or 1;
L 2 represents a single bond, a divalent substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a divalent substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, or a divalent linked aromatic group formed by linking 2 to 6 aromatic groups selected from the aromatic hydrocarbon groups or the aromatic heterocyclic groups, L 1 represents a divalent linked aromatic group formed by linking 2 aromatic groups selected from the aromatic hydrocarbon groups or the aromatic heterocyclic groups, terminal L 1 and L 2 may each represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and when L 1 and L 2 each represent the linked aromatic group, the group may be linear or branched, and aromatic rings to be linked may be identical to or different from each other, provided that when r represents 0, the single bond is excluded, and when r represents 1, at least one aromatic heterocyclic group is included;
L 3 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, a linked aromatic group formed by linking 2 to 6 aromatic groups selected from the substituted or unsubstituted aromatic hydrocarbon groups and the substituted or unsubstituted aromatic heterocyclic groups, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, and when L 3 represents the linked aromatic group, the group may be linear or branched, and aromatic rings to be linked may be identical to or different from each other;
wherein when the aromatic group in each of L 1 to L 3 has a substituent, the substituent is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an acetyl group, the aromatic group may have a plurality of substituents, and the plurality of substituents may be identical to or different from each other; and
wherein, in each of the general formulae (1) to (3), at least one of L 1 to L 3 is a carbazolyl (Cz) group or a Cz containing group.
14. A material for an organic electroluminescent device, comprising a carborane compound represented by the general formula (1), (2), or (3):
wherein,
a ring A represents a divalent carborane group C 2 B 10 H 10 represented by the formula (1a) or the formula (1 b), and when a plurality of rings A are present in a molecule thereof, the rings may be identical to or different from each other;
r represents a number of repetitions and represents an integer of 0 or 1;
L 1 represents a single bond, a divalent substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a divalent substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, L 2 represents a single bond, a divalent substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a divalent substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, or a divalent linked aromatic group formed by linking 2 to 6 aromatic groups selected from the aromatic hydrocarbon groups or the aromatic heterocyclic groups, terminal L 1 and L 2 may each represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and when L 1 and L 2 each represent the linked aromatic group, the group may be linear or branched, and aromatic rings to be linked may be identical to or different from each other, provided that when r represents 0, the single bond is excluded, and when r represents 1, at least one aromatic heterocyclic group is included;
L 3 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, a linked aromatic group formed by linking 2 to 6 aromatic groups selected from the substituted or unsubstituted aromatic hydrocarbon groups and the substituted or unsubstituted aromatic heterocyclic groups, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, and when L 3 represents the linked aromatic group, the group may be linear or branched, and aromatic rings to be linked may be identical to or different from each other;
wherein when the aromatic group in each of L 1 to L 3 has a substituent, the substituent is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an acetyl group, the aromatic group may have a plurality of substituents, and the plurality of substituents may be identical to or different from each other; and
wherein, in each of the general formulae (1) to (3), at least one of L 1 to L 3 is a carbazolyl (Cz) group or a Cz containing group.
15. A material for an organic electroluminescent device, comprising a carborane compound represented by the general formula (1), (2), or (3):
wherein,
a ring A represents a divalent carborane group C 2 B 10 H 10 represented by the formula (1a) or the formula (1b), and when a plurality of rings A are present in a molecule thereof, the rings may be identical to or different from each other;
r represents a number of repetitions and represents an integer of 0 or 1;
L 1 and L 2 each represent a single bond, a divalent substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a divalent substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, or a divalent linked aromatic group formed by linking 2 to 6 aromatic groups selected from the aromatic hydrocarbon groups or the aromatic heterocyclic groups, terminal L 1 and L 2 may each represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and when L 1 and L 2 each represent the linked aromatic group, the group may be linear or branched, and aromatic rings to be linked may be identical to or different from each other, provided that when r represents 0, the single bond is excluded, and when r represents 1, at least one aromatic heterocyclic group is included;
L 3 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, a linked aromatic group formed by linking 2 to 6 aromatic groups selected from the substituted or unsubstituted aromatic hydrocarbon groups and the substituted or unsubstituted aromatic heterocyclic groups, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, and when L 3 represents the linked aromatic group, the group may be linear or branched, and aromatic rings to be linked may be identical to or different from each other;
wherein when the aromatic group in each of L 1 to L 3 has a substituent, the substituent is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an acetyl group, the aromatic group may have a plurality of substituents, and the plurality of substituents may be identical to or different from each other;
wherein, in each of the general formulae (1) to (3), at least one of L 1 to L 3 is a carbazolyl (Cz) group or a Cz containing group; and
wherein, in each of the general formulae (1) to (3), L 1 or L 3 is Cz.