Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex
View Patent ↗An organic light-emitting device comprising a light-emitting layer or a plurality of thin organic compound layers containing a light emitting layer interposed between a pair of electrodes, wherein at least one layer comprises at least one light emitting material containing a compound having a partial structure represented by following formula (21) or a tautomer thereof: wherein the compound having the partial structure represented by formula (21) has two or more different ligands.
1. An organic light-emitting device comprising:
a light-emitting layer or a plurality of thin organic compound layers containing a light emitting layer interposed between a pair of electrodes, wherein at least one layer comprises at least one light emitting material containing a compound having a partial structure represented by following formula (21) or a tautomer thereof:
wherein the compound having the partial structure represented by formula (21) has two or more different ligands.
2. The organic light-emitting device according to claim 1 , wherein the compound having the partial structure represented by formula (21) has one iridium atom per molecule.
3. The organic light-emitting device according to claim 1 , wherein the number of carbon atoms in the compound having the partial structure represented by formula (21) is from 15 to 100.
4. The organic light-emitting device according to claim 1 , wherein the compound having the partial structure represented by formula (21) has a nitrogen-containing heterocyclic derivative ligand or a diketone ligand.
5. The organic light-emitting device according to claim 1 , wherein the compound having the partial structure represented by formula (21) is a compound represented by following formula (23):
wherein R 11 and R 12 each represents a substituent; R 13 , R 14 and R 15 each represents a hydrogen atom or a substituent; m 1 represents an integer of from 0 to 4; and m 2 represents an integer of from 0 to 6.
6. The organic light-emitting device according to claim 5 , wherein m 1 or m 2 is plural, and one of the plurality of R 11 s is connected to another of the plurality of R 11 s to form a cyclic structure, or one of the plurality of R 12 s is connected to another of the plurality of R 12 s to form a cyclic structure, or one of the plurality of R 11 s is connected to one of the plurality of R 12 s to form a cyclic structure.
7. The organic light-emitting device according to claim 5 , wherein R 11 and R 12 each represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a halogen atom, a cyano group or a cyclic structure obtained by the connection of one of the plurality of R 11 s to another of the plurality of R 11 s, or one of the plurality of R 12 s to another of the plurality of R 12 s, or one of the plurality of R 11 s to one of the plurality of R 12 s.
8. The organic light-emitting device according to claim 5 , wherein R 11 and R 12 each represents an alkyl group, an aryl group or groups which are connected to each other to form an aromatic group.
9. The organic light-emitting device according to claim 5 , wherein R 13 and R 15 each represents an alkyl group, an aryl group or a heteroaryl group; and R 14 represents a hydrogen atom or an alkyl group.
10. The organic light-emitting device according to claim 5 , wherein R 13 and R 15 each represents an alkyl group; and R 14 represents a hydrogen atom.
11. The organic light-emitting device according to claim 5 , wherein m 1 represents an integer of from 0 to 2.
12. The organic light-emitting device according to claim 5 , wherein m 2 represents an integer of from 0 to 2.
13. The organic light-emitting device according to claim 5 , wherein a quinoline derivative ligand in the compound represented by formula (23) is formed by at least four rings.
14. The organic light-emitting device according to claim 1 , wherein the compound having the partial structure represented by formula (21) is a compound represented by following formula (24):
wherein R 11 and R 12 each represents a substituent; m 1 represents an integer of from 0 to 4; m 2 represents an integer of from 0 to 6; Z 2 represents an atomic group which forms an aryl ring or a heteroaryl ring; Z 3 represents an atomic group which forms a nitrogen-containing heteroaryl ring; and n 1 represents an integer of from 1 to 2.
15. The organic light-emitting device according to claim 14 , wherein m 1 or m 2 is plural, and one of the plurality of R 11 s is connected to another of the plurality of R 11 s to form a cyclic structure, or one of the plurality of R 12 s is connected to another of the plurality of R 12 s to form a cyclic structure, or one of the plurality of R 11 s is connected to one of the plurality of R 12 s to form a cyclic structure.
16. The organic light-emitting device according to claim 14 , wherein R 11 and R 12 each represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a halogen atom, a cyano group or a cyclic structure obtained by the connection of one of the plurality of R 11 s to another of the plurality of R 11 s, or one of the plurality of R 12 s to another of the plurality of R 12 s, or one of the plurality of R 11 s to one of the plurality of R 12 s.
17. The organic light-emitting device according to claim 14 , wherein R 11 and R 12 each represents an alkyl group, an aryl group or groups which are connected to each other to form an aromatic group.
18. The organic light-emitting device according to claim 14 , wherein Z 2 represents an atomic group which forms an aryl ring having from 6 to 30 carbon atoms or a 5- or 6-membered heteroaryl ring.
19. The organic light-emitting device according to claim 14 , wherein Z 3 represents a 5- or 6-membered nitrogen-containing heteroaryl ring.
20. The organic light-emitting device according to claim 14 , wherein m 1 represents an integer of from 0 to 2.
21. The organic light-emitting device according to claim 14 , wherein m 2 represents an integer of from 0 to 2.
22. The organic light-emitting device according to claim 14 , wherein a quinoline derivative ligand in the compound represented by formula (24) is formed by at least four rings.
23. The organic light-emitting device according to claim 1 , which is formed by a resistively-heated vacuum evaporation method, an electron beam method, a sputtering method, a molecular lamination method, a coating method, an ink jet method or a printing method.
24. The organic light-emitting device according to claim 23 , which is formed by a coating method.
25. The organic light-emitting device according to claim 1 , further comprising:
a hole transporting layer formed by a coating method.
26. The organic light-emitting device according to claim 1 , wherein the plurality of thin organic compound layers are formed by a resistively-heated vacuum evaporation method.
27. The organic light-emitting device according to claim 1 , which emits light having λmax of 590 nm or more.
28. The organic light-emitting device according to claim 1 , which is an organic electroluminescence device.
29. The organic light-emitting device according to claim 1 , further comprising:
a compound having an ionization potential of 5.9 eV or more interposed between a cathode of the pair of electrodes and the light-emitting layer.
30. The organic light-emitting device according to claim 1 , which emits light having a CIE chromaticity value x of 0.50 or more and a CIE chromaticity value y of 0.50 or less.
31. The organic light-emitting device according to claim 1 , which emits light having a half width of spectrum of 100 nm or less.
32. The organic light-emitting device according to claim 1 , wherein an anode of the pair of electrodes comprises an electrically-conductive metal oxide.
33. The organic light-emitting device according to claim 1 , wherein a cathode of the pair of electrodes is aluminum, a lithium-aluminum alloy or a mixture of aluminum and lithium or a magnesium-silver alloy or a mixture of magnesium and silver.
34. The organic light-emitting device according to claim 1 , which comprises a positive hole-injecting layer and a positive hole-transporting layer,
wherein the positive hole-injecting layer and the positive hole-transporting layer have an arylamine derivative.
35. The organic light-emitting device according to claim 1 , which comprises an electron-injecting layer and an electron-transporting layer,
wherein the electron-injecting layer and the electron-transporting layer are formed by a vacuum evaporation method.
36. The organic light-emitting device according to claim 1 , wherein the light-emitting layer is formed by a vacuum evaporation method.
37. The organic light-emitting device according to claim 1 , which comprises a positive hole-injecting layer or a positive hole-transporting layer,
wherein the positive hole-injecting layer or the positive hole-transporting layer contains a carbazole derivative, a triazole derivative, an oxazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative, a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, a styrylanthracene derivative, a fluorenone derivative, a hydrazone derivative, a stilbene derivative, a silazane derivative, an aromatic tertiary amine compound, a styrylamine compound, an aromatic dimethylidine compound, a porphyrin compound, a polysilane compound, a poly(N-vinylcarbazole) derivative, an aniline copolymer, a thiophene oligomer, a polythiophene or an organic silane derivative.
38. The organic light-emitting device according to claim 1 , which comprises following compound A′:
39. The organic light-emitting device according to claim 1 , which comprises a compound represented by following formula (24) and following compound A′:
wherein R 11 and R 12 each represents a substituent; m 1 represents an integer of from 0 to 4; m 2 represents an integer of from 0 to 6; Z 2 represents an atomic group which forms an aryl ring or a heteroaryl ring; Z 3 represents an atomic group which forms a nitrogen-containing heteroaryl ring; and n 1 represents an integer of 1 or 2.
40. The organic light-emitting device according to claim 1 , which comprises following compound C′:
41. The organic light-emitting device according to claim 1 , which comprises a layer composed of following compound C′:
42. The organic light-emitting device according to claim 1 , which is used for a display device, a display, a backlight, electrophotography, an illuminating light source, a recording light source, an exposure light source, a reading light source, a sign, an advertising display or an interior lighting.
43. A display, comprising the organic light-emitting device according to claim 1 .
44. A backlight, comprising the organic light-emitting device according to claim 1 .
45. A method for producing the organic light-emitting device according to claim 1 , the method comprising:
forming the light-emitting layer or the plurality of thin organic compound layers by a coating method.