Organic-electroluminescent-element material and organic electroluminescent elements using same
View Patent ↗Disclosed are an organic electroluminescent device that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple construction, and a material for an organic electroluminescent device to be used in the device. The material is a material for an organic electroluminescent device formed of a carborane compound having an indolocarbazole skeleton and one or two or more carborane groups each bonded thereto directly or through a divalent group. In addition, the device is an organic electroluminescent device having organic layers including a light-emitting layer between an anode and a cathode laminated on a substrate, in which at least one layer of the organic layers contains the material for an organic electroluminescent device. In addition, the device is an organic electroluminescent device containing, as a host material for a light-emitting layer containing a phosphorescent light-emitting dopant and the host material, the material for an organic electroluminescent device.
1. A material for an organic electroluminescent device, comprising a carborane compound represented by the general formula (1):
wherein:
a ring A represents an aromatic ring represented by the formula (1a), the ring being fused with an adjacent ring at an arbitrary position, a ring B represents a heterocycle represented by the formula (1b) whose nitrogen-containing five-membered ring is fused with an adjacent ring at an arbitrary position, and X represents a methine group;
a ring Z represents a divalent carborane group C 2 B 10 H 10 represented by the formula (1c), wherein a total number of the ring Z is 1 to 3, and when the plurality of rings Z's are present in a molecule, the rings may be identical to or different from each other;
p, q, r, and s each represent a number of repetitions, and m and n each represent a number of substitutions, and p, q, r, and s, and m and n each represent an integer of from 0 to 2, provided that any one of q×m, r×n, p, and s represents an integer of 1 or more;
L 1 and L 4 each independently represent a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 22 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group formed by linking 2 to 6 arbitrary aromatic groups each selected from the substituted or unsubstituted aromatic hydrocarbon group and the substituted or unsubstituted aromatic heterocyclic group, and the linked aromatic group may be linear or branched;
L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 22 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a linked aromatic group formed by linking 2 to 6 arbitrary aromatic groups each selected from the substituted or unsubstituted aromatic hydrocarbon group and the substituted or unsubstituted aromatic heterocyclic group, and the linked aromatic group may be linear or branched;
R 1 and R 5 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 22 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group formed by linking 2 to 6 arbitrary aromatic groups each selected from the substituted or unsubstituted aromatic hydrocarbon group and the substituted or unsubstituted aromatic heterocyclic group, and the linked aromatic group may be linear or branched; and
R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 22 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a linked aromatic group formed by linking 2 to 6 arbitrary aromatic groups each selected from the substituted or unsubstituted aromatic hydrocarbon group and the substituted or unsubstituted aromatic heterocyclic group, and the linked aromatic group may be linear or branched.
2. A material for an organic electroluminescent device according to claim 1 , wherein q and r in the general formula (1) each represent an integer of 0.
3. A material for an organic electroluminescent device according to claim 1 , wherein L 1 and L 4 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 16 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups each selected from the aromatic hydrocarbon group and the aromatic heterocyclic group, and L 2 and 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 18 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups each selected from the aromatic hydrocarbon group and the aromatic heterocyclic group.
4. A material for an organic electroluminescent device according to claim 3 , wherein L 1 and L 4 each independently represent a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups each selected from the aromatic heterocyclic group, and L 2 and L 3 each independently represent a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups each selected from the aromatic heterocyclic group.
5. A material for an organic electroluminescent device according to claim 1 , wherein R 1 and R 5 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 16 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups each selected from the aromatic hydrocarbon group and the aromatic heterocyclic group, and R 2 , R 3 , and R 4 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 18 carbon atoms, or a linked aromatic group formed by linking 2 to 6 aromatic groups each selected from the aromatic hydrocarbon group and the aromatic heterocyclic group.
6. An organic electroluminescent device having a structure in which an anode, organic layers, and a cathode are laminated on a substrate, wherein at least one layer of the organic layers comprises an organic layer containing the material for an organic electroluminescent device of claim 1 .
7. An organic electroluminescent device according to claim 6 , 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.
8. An organic electroluminescent device according to claim 6 , wherein the organic layer containing the material for an organic electroluminescent device comprises a light-emitting layer containing a phosphorescent light-emitting dopant.
9. An organic electroluminescent device according to claim 8 , wherein an emission wavelength of the phosphorescent light-emitting dopant has an emission maximum wavelength at 600 nm or less.
10. An organic electroluminescent device having a structure in which an anode, organic layers, and a cathode are laminated on a substrate, wherein at least one layer of the organic layers comprises an organic layer containing the material for an organic electroluminescent device of claim 2 .
11. An organic electroluminescent device having a structure in which an anode, organic layers, and a cathode are laminated on a substrate, wherein at least one layer of the organic layers comprises an organic layer containing the material for an organic electroluminescent device of claim 3 .
12. An organic electroluminescent device having a structure in which an anode, organic layers, and a cathode are laminated on a substrate, wherein at least one layer of the organic layers comprises an organic layer containing the material for an organic electroluminescent device of claim 4 .
13. An organic electroluminescent device having a structure in which an anode, organic layers, and a cathode are laminated on a substrate, wherein at least one layer of the organic layers comprises an organic layer containing the material for an organic electroluminescent device of claim 5 .