WO2005105746A1 - 有機金属錯体、発光性固体、有機el素子及び有機elディスプレイ - Google Patents
有機金属錯体、発光性固体、有機el素子及び有機elディスプレイ Download PDFInfo
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- WO2005105746A1 WO2005105746A1 PCT/JP2004/006329 JP2004006329W WO2005105746A1 WO 2005105746 A1 WO2005105746 A1 WO 2005105746A1 JP 2004006329 W JP2004006329 W JP 2004006329W WO 2005105746 A1 WO2005105746 A1 WO 2005105746A1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical group CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
- C07C37/66—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring by conversion of hydroxy groups to O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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Definitions
- Organometallic complexes, luminescent solids, organic EL devices and organic EL displays Organometallic complexes, luminescent solids, organic EL devices and organic EL displays
- the present invention relates to an organic metal complex, a luminescent solid, and an organic EL device using the organometallic complex or the luminescent solid, which emit phosphorescence and are suitable as a luminescent material or a color conversion material in an organic EL device, a lighting device, or the like. , And an organic EL display using the organic EL element
- the organic EL device has a structure in which one or more thin organic layers are sandwiched between a negative electrode and a positive electrode, and holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic material layer, respectively.
- the recombination energy when the holes and the electrons recombine in the organic layer excites the luminescent center of the luminescent material in the organic layer, and the luminescent material is deactivated from the excited state to the ground state. It is a light emitting element using light emitted at the time.
- the organic EL element has features such as self-luminous light and high-speed response, has good visibility, is ultra-thin, lightweight, and has excellent high-speed response and moving image display properties. It is expected to be applied to displays.
- a fluorescent material having a high luminous luminous property is doped as a guest material in a small amount with respect to a luminous luminous host material as a main material, so that luminescence exhibiting high luminous efficiency is obtained. It has been proposed to form a layer (CW Tang, SA Van Slyke, and CH Chen, Journal of Applied Physics vol. 65, 3610 (1989)).
- organic EL devices using an organometallic complex that emits phosphorescence at room temperature include a platinum element and a nitrogen element as described in JP-A-2002-36532.
- a metal complex having an NNNNC type tridentate ligand composed of two coordination bonds and a direct bond between a platinum element and a carbon atom is given as an example.
- this metal complex does not have sufficient phosphorescence luminous efficiency at room temperature, and an organic EL device using this metal complex has a problem that the luminous efficiency is low.
- Patent Document 1
- An object of the present invention is to solve the conventional problems and achieve the following objects.
- the present invention uses an organometallic complex, a luminescent solid, or an organometallic complex or a luminescent solid which emits phosphorescent light and is suitable as a luminescent material or a color conversion material in an organic EL element, a lighting device, or the like.
- An organic EL device with excellent luminous efficiency, thermal and electrical stability, a very long driving life, and a high performance and long life using this organic EL device.
- An object of the present invention is to provide an organic EL display which can be made constant, is suitable for a full-color display or the like having a good color balance without changing the light emitting area, and has a long driving life. Disclosure of the invention
- the metal atom and the N lambda C New type of tridentate ligands showed strong phosphorescent metal complex comprising a specific monodentate ligand, illustrate preferred good sublimable organic EL element,
- a good neat film, a dope film, etc. can be formed by vacuum evaporation, and it is suitable as a light emitting material in an organic EL device or a lighting device, etc., and an organic EL device and an organic EL display using the organometallic complex. Is known to have excellent longevity, luminous efficiency, thermal and electrical stability, extremely long drive life, and high performance.
- the present invention is based on the above findings by the present inventors, and the present invention for solving the above problems is as follows.
- the organometallic complex of the present invention is a tridentate in which a metal atom is bonded to the metal atom tridentate via two nitrogen atoms and a carbon atom, and the carbon atom is located between the two nitrogen atoms. And for the metal atom.
- Luminescence from organic substances is classified into fluorescence and phosphorescence depending on the nature of the excited state that produces light emission.However, conventionally, organic substances generally do not produce phosphorescence, so they are used in organic EL elements and lighting devices. Fluorescent light-emitting materials have been used as light-emitting materials and color conversion materials. However, from the EL emission mechanism, it is expected that a phosphorescent state will be generated with a probability four times that of the fluorescent state. Therefore, application of metal complexes that generate phosphorescent light at room temperature to light-emitting materials is not possible. It is effective in increasing the efficiency of EL devices, and has attracted attention in recent years.
- the organometallic complex of the present invention Since the phosphorescence is strongly generated from the organometallic complex of the present invention, the internal quantum efficiency of an EL device using a fluorescent material is 25% at the maximum, whereas 1% at the maximum in theory. Luminous efficiency as high as 0% can be achieved. Therefore, the organometallic complex exhibiting strong phosphorescence is suitable as a light emitting material or the like in an organic EL device or the like.
- the organometallic complexes of the present invention by changing the skeletal structure in particular of the tridentate ligand ( ⁇ ⁇ C ⁇ ⁇ -type) or the monodentate ligand, such substituents and number, etc., and emission You can change the color.
- the luminescent solid of the present invention contains the organometallic complex of the present invention.
- the luminescent solid of the present invention containing the organometallic complex of the present invention has an extremely long driving life, is excellent in life and luminous efficiency, and can be suitably used for lighting devices, display devices, and the like.
- the organic EL device of the present invention has an organic thin film layer between a positive electrode and a negative electrode, and the organic thin film layer contains the organometallic complex.
- the organic EL device of the present invention containing the organometallic complex of the present invention has a very long driving life, is excellent in life and luminous efficiency, and can be suitably used for lighting devices, display devices and the like.
- the organic EL display of the present invention uses the organic EL device of the present invention.
- the organic EL display of the present invention using the organic EL element of the present invention has a very long driving life and is excellent in life, luminous efficiency, and the like.
- FIG. 1 is a schematic explanatory diagram showing an example of a layer configuration in an organic EL device of the present invention.
- FIG. 2 is a schematic explanatory diagram showing an example of a structure of an organic EL display.
- FIG. 3 is a schematic explanatory view showing one structural example of an organic EL display.
- FIG. 4 is a schematic explanatory view showing one structural example of an organic EL display.
- FIG. 5 is a schematic explanatory view showing one structural example of a passive matrix organic EL display (passive matrix panel).
- FIG. 6 is a schematic explanatory diagram showing a circuit in the passive matrix organic EL display (passive matrix panel) shown in FIG.
- FIG. 7 is a schematic explanatory view showing an example of the structure of an active matrix organic EL display (active matrix panel).
- FIG. 8 is a schematic explanatory diagram showing a circuit in the active matrix organic EL display (active matrix panel) shown in FIG.
- Figure 9 is a chart of the IR spectrum of Pt (3,5-di (2-pyridyl) toluene) (bihue-loxyside).
- FIG. 10 is a chart of the IR spectrum of Pt (3,5_di (2-pyridyl) tonolene) (OH).
- Figure 11 is a chart of the IR status of Pt (3,5-di (2-pyridyl) toluene) (1,2,4-triazolate).
- Figure 12 is a chart of the IR spectrum of Pt (3,5-di (2-pyridyl) toluene) (2-benzothiazolate).
- Figure 13 is a chart of the IR status of Pt (3,5-di (2-pyridyl) toluene) (phenylacetylide).
- FIG. 14 is a schematic diagram for explaining an outline of an experiment for calculating a phosphorescence quantum yield.
- FIG. 15 is a chart of the EL spectrum of the organic EL device of Example 14. BEST MODE FOR CARRYING OUT THE INVENTION (Organometallic complex and luminescent solid)
- the organometallic complex of the present invention comprises a metal atom, a specific tridentate ligand bound to the metal atom at a tridentate, and a specific monodentate ligand bound to the metal atom at a monodentate. It has.
- the luminescent solid of the present invention contains the above-mentioned organometallic complex of the present invention, and further contains other components appropriately selected according to the purpose.
- the embodiment of the luminescent solid is not particularly limited and can be appropriately selected depending on the purpose. Examples thereof include a crystal and a thin film.
- the content of the organic complex metal in the luminescent solid is not particularly limited and can be appropriately selected depending on the purpose. Usually, the content is 0.1 to 50% by mass, and preferably 0.5 to 50% by mass. Highly efficient light emission can be obtained at 20% by mass.
- One metal atom is 0.1 to 50% by mass, and preferably 0.5 to 50% by mass. Highly efficient light emission can be obtained at 20% by mass.
- the metal atom acts as a central metal in the organometallic complex.
- the metal atom is not particularly limited and can be appropriately selected depending on the purpose. For example, Fe, Co, Ni, Ru, Rh, Pd, Os, IR, Pt and the like. These are contained in one molecule of the organometallic complex, and each metal atom in two or more molecules of the organometallic complex may be used alone or in combination of two or more. Good.
- Pt is particularly preferable (in this case, the organometallic complex is a platinum complex).
- Tridentate ligand Tridentate ligand
- the tridentate ligand is a tridentate bond to the metal atom via two nitrogen atoms and a carbon atom, and the carbon atom is located between the two nitrogen atoms (N ⁇ C ⁇ N-type) is not particularly limited and may be appropriately selected depending on the intended purpose.
- the two nitrogen atoms and the three carbon atoms are part of different ring structures.
- the two nitrogen atoms are a first nitrogen atom and a second nitrogen atom
- the first nitrogen atom adjacent to the first nitrogen atom in the ring structure containing the first nitrogen atom is preferred.
- the monodentate ligand is not particularly limited as long as it binds to the metal atom through one atom selected from C atom, N atom, O atom, P atom and S atom. Can be appropriately selected depending on the purpose, but if the charge of the whole organometallic complex can be made neutral, the organometallic complex can be given sublimability. preferable. Specific example of one organometallic complex
- organometallic complex of the present invention include, for example, an organometallic complex represented by the following general formula (1).
- M represents the above-described metal atom.
- Ar 1, Ar 2 and Ar 3 represent a ring structure, and are preferably selected from a five-membered ring group, a six-membered ring group, and a condensed ring group thereof.
- Ar 2 has a benzene ring structure, a pyridine ring structure, and a pyrimidine ring structure.
- M represents the above metal atom
- Ar 1 and Ar 2 represent the above ring structure.
- Ar 1 or Ar 3 is a monocyclic heteroaromatic group or a polycyclic heteroaromatic group, and specifically, the following structure is more preferable.
- Ar 1 and Ar 3 may be the same or different from each other, but are preferably the same as each other.
- Rl, 12 and 13 each represent a hydrogen atom or a substituent that replaces Ar1, Ar2 and Ar3, and may be the same or different; Each may be plural, and adjacent ones may combine to form a ring structure.
- R 1, R 2 and R 3 are preferably a halogen atom, a cyano group, an alkoxy group, an amino group, an alkyl group, an alkyl acetate group, a cycloalkyl group, an aryl group, an aryloxy group, and the like. No. These may be further substituted with known substituents.
- Preferable examples of L include a group having the following structure.
- a hydrogen atom may be substituted with an organic group or a halogen atom
- R represents a hydrogen atom, an alkyl group, or an aryl group.
- 4 and 15 represent any of a hydrogen atom, an alkyl group, an aryl group, an alkoxyl group, and an aryloxy group.
- the organometallic complex represented by the general formula (1) is electrically neutral and exhibits sublimability in a vacuum, not only a known coating method but also a true coating method can be used for forming a thin film. This is advantageous in that an empty deposition method or the like can be suitably applied.
- the structure of Ar 2 having a benzene ring structure is as follows.
- the structure of the above Ar 1 and the above Ar 3 also having a benzene ring structure is as follows.
- the photoluminescence (PL) of the organometallic complex of the present invention (hereinafter sometimes abbreviated simply as “PL”)
- the quantum yield is defined as the aluminum quinoline complex (A)
- the PL quantum efficiency can be measured and calculated as follows, for example. That is, as shown in FIG. 14, a thin film sample 102 on a transparent substrate is irradiated obliquely with excitation light (365 nm steady light) 100 from a light source, and a spectral radiance meter (CS-1000, manufactured by Minolta) is used.
- the PL photon number [sample (sample)] is calculated from the PL spectrum of the thin film measured using 104 and the conversion. Simultaneously with emission measurements, the excitation light transmitted through ⁇ Pi reflected from the sample was Osamuhikari by the mirror 106, the total strength [J (sam P le)] of the photo die Detect at mode 108.
- the PL quantum yield of the sample thin film can be calculated by the following equation. I. P (sampie) / ⁇ I (substrate)-I (sample)]
- the method for synthesizing the organometallic complex of the present invention is not particularly limited and may be appropriately selected depending on the intended purpose.
- the tridentate ligand ( N ⁇ CN type) and the metal atom Suitable examples include a method in which an organometallic complex (precursor) having a halogen atom (chlorine atom) is reacted with a hydrogen-substituted or alkali-metal-substituted monodentate ligand according to appropriately selected conditions.
- the above reaction can be suitably performed even in the presence of a catalyst.
- the catalyst is not particularly limited and can be appropriately selected depending on the purpose.
- a copper salt-organoamine catalyst, and the like are preferably used. No. These may be used alone or in combination of two or more.
- the method for synthesizing the organometallic complex (precursor) having the tridentate ligand, the metal atom, and the halogen atom (chlorine atom) is not particularly limited and may be appropriately selected depending on the purpose.
- a method described in the above-mentioned document [DJ Cardenas and AM Ech avarren, Organome tallies Vol. 183337 (19 ")] can be preferably exemplified.
- the organometallic complex of the present invention is as described above. Although it has excellent PL quantum efficiency and high luminous efficiency, it can be suitably used in various fields.However, the organic EL element and the lighting device can be used in various fields.
- each color of red, green and blue is used in order to obtain a full-color display.
- a combination of 9 organic EL elements is used as one pixel, but in this case, three color organic EL elements are required.
- the organometallic complex of the present invention can adjust or change the emission color by appropriately changing the molecular structure of the tridentate ligand, and can emit red, green, and blue light. It is advantageous to apply the organometallic complex to the organic EL device.
- the organic EL device of the present invention has an organic thin film layer between a positive electrode and a negative electrode, and the organic thin film layer contains the organometallic complex of the present invention. Of layers or members.
- the organic thin film layer is not particularly limited and can be appropriately selected depending on the intended purpose.
- the organic thin film layer has at least a light emitting layer, and further has a hole injection layer, a hole transport layer, and a hole as needed. It may have a blocking layer, an electron transport layer, an electron injection layer, and the like.
- the light emitting layer may be formed as a single function as a light emitting layer, or may be formed with multiple functions such as a light emitting layer and an electron transport layer, a light emitting layer and a hole transport layer, and the like.
- One light emitting layer emitting layer is not particularly limited and can be appropriately selected depending on the intended purpose.
- the organic thin film layer has at least a light emitting layer, and further has a hole injection layer, a hole transport layer, and a hole as needed. It may have a blocking layer, an electron transport layer, an electron injection layer, and the like.
- the light emitting layer may be formed as a single function as a light emitting layer, or may be
- the light-emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose.
- the light-emitting layer preferably contains the organometallic complex of the present invention as a light-emitting material.
- the light-emitting layer may be formed by forming the organometallic complex alone, or may be formed of another material other than the organometallic complex, such as the organometallic complex of the present invention.
- the material may include a host material having an emission wavelength near the light absorption wavelength of the guest material.
- the host material is preferably contained in the light emitting layer, but may be contained in a hole transport layer, an electron transport layer, or the like.
- the host material When the organometallic complex of the present invention as the guest material is used in combination with the host material, the host material is first excited when EL light emission occurs. And the emission wavelength of the host material and the absorption wavelength of the guest material (the organometallic complex) Because of the overlap, the excitation energy efficiently moves from the host material to the guest material, the host material returns to the ground state without emitting light, and only the guest material in the excited state uses the excitation energy as light. Since it emits, it has excellent luminous efficiency and color purity.
- the light-emitting molecules approach each other to cause an interaction between the light-emitting molecules, which causes a phenomenon called “concentration quenching” that lowers the light emission efficiency.
- concentration quenching occurs because the organometallic complex that is the guest compound is dispersed at a relatively low concentration in the host compound. Is effectively suppressed and the light emission efficiency is excellent.
- the host material generally has excellent film forming properties, and thus is advantageous in that the light emitting properties are maintained and the film forming properties are excellent. is there. '
- the host material is not particularly limited and may be appropriately selected depending on the purpose.
- a material having an emission wavelength near the light absorption wavelength of the guest material is preferable.
- the following structural formula (1) An aromatic amine derivative represented by the following structural formula (2), a carbazole derivative represented by the following structural formula (3), an oxine complex represented by the following structural formula (3), and 1,3 represented by the following structural formula (4) , 6,8-Tetrafluorovinylene compound, 4,4,1-bis (2,2,1-divinyl) -1 1,1,1-biphenyl (DPVB i) represented by the following structural formula (5)
- Main emission wavelength 470 nm)
- p-Cesquiphenyl (main emission wavelength 400 nm) represented by the following structural formula (6)
- n represents an integer of 2 or 3.
- Ar represents a divalent or trivalent aromatic group or a heterocyclic aromatic group.
- R 7 and R 8 may be the same as or different from each other, and represent a monovalent aromatic group or a heterocyclic aromatic group.
- the monovalent aromatic group or heterocyclic aromatic group is not particularly limited and may be appropriately selected depending on the purpose.
- N, N, -dinaphthyl-N, N, diphenyl- [1,1, -biphenyl] represented by the following structural formula (1) -11 1,4,4-Diamine (NPD) (main emission wavelength 430 nm) and its derivatives are preferred.
- Ar represents a divalent or trivalent group containing an aromatic ring or a divalent or trivalent group containing a heterocyclic aromatic ring shown below.
- R represents a linking group, and examples thereof include the following.
- R 9 and R 10 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, an aryl group, a cyano group, an amino group, an acyl group, Represents an alkoxycarbonyl group, a carbonyl group, an alkoxy group, an alkylsulfonyl group, a hydroxyl group, an amide group, an aryloxy group, an aromatic hydrocarbon ring group, or an aromatic heterocyclic group, which are further substituted with a substituent.
- n represents an integer, and 2 or 3 is preferable.
- Ar is an aromatic group in which two benzene rings are connected via a single bond
- R 9 and R 1 ° are hydrogen atoms
- CBP 4,4,1-bis (9-l-rubazolyl) -biphenyl
- main emission wavelength 380 nm
- R 11 represents a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, an aryl group, a cyano group, an amino group, an acyl group, an alkoxycarbyl group, or a propyloxyl group.
- R 1 2 ⁇ 1 5 may be the different from one may be identical or different, represent a hydrogen atom or a substituent.
- Preferred examples of the substituent include an alkyl group, a cycloalkyl group and an aryl group, and these may be further substituted with a substituent.
- the host material as the polymer material is not particularly limited and can be appropriately selected depending on the purpose. Examples thereof include polyparaphenylenevinylene (PPV), polythiophene (PAT), Polyparaphenylene (PPP), Polyvinylcarbazole (PVCz), Polyfluorene (PF), Poly
- R represents a hydrogen atom, a halogen atom, an alkoxy group, an amino group, an alkyl group, a cycloalkyl group, an aryl group which may contain a nitrogen atom or a sulfur atom, or an aryloxy group; It may be substituted with a substituent.
- X represents an integer.
- PVC z polyvinyl carbazole represented by the following structural formula (8) is preferable in terms of efficient energy transfer from the host to the guest.
- R 17 and R 18 each represent a plurality of substituents provided at arbitrary positions of the cyclic structure, and each independently represents a hydrogen atom, a halogen atom, an alkoxy group, an amino group.
- arbitrary adjacent substituent positions may be bonded to each other to form an aromatic ring which may contain a nitrogen atom, a sulfur atom, and an oxygen atom. May be substituted with a group.
- X represents an integer.
- the host material which is the polymer material When the host material which is the polymer material is used, the host material is dissolved in a solvent, and the organometallic complex of the present invention which is the guest material is mixed to prepare a coating solution.
- a hole transporting layer material and an electron transporting layer material can be simultaneously mixed in a solution on the layer to form a film.
- These wet film forming methods are particularly suitable when the multifunctional light emitting layer is formed as a single layer (a hole transport layer, an electron transport layer and a light emitting layer).
- the layer containing the organometallic complex in the light emitting layer is not particularly limited. It can be appropriately selected depending on, for example, from 0.1 to 5 0 wt% and and even good preferred, from 0.5 to 2 and more preferably 0 mass 0/0.
- the content is less than 0.1% by mass, the life and luminous efficiency may not be sufficient. If the content is more than 50% by mass, the color purity may be reduced. It is preferable that the content be in the preferable range in terms of life, luminous efficiency, and the like.
- the content of the organometallic complex in these layers is the same as described above. can do.
- the light emitting layer is capable of injecting holes from the positive electrode, the hole injection layer, the hole transport layer, or the like when an electric field is applied, and injecting electrons from the negative electrode, the electron injection layer, the electron transport layer, or the like.
- other light-emitting materials may be contained in the range that does not impair the light emission, in addition to the organometallic complex.
- the light emitting layer can be formed according to a known method, and examples thereof include a vapor deposition method, a wet film formation method, an MBE (molecular beam epitaxy) method, a cluster ion beam method, a molecular lamination method, an LB method, a printing method, and a transfer method. It can be suitably formed by a method, etc.
- the vapor deposition method is preferable in that it can be easily and efficiently manufactured at low cost without using a waste liquid without using an organic solvent.
- the light emitting layer is formed in a single layer structure, For example, when the light emitting layer is formed as a hole transporting layer, a light emitting layer, and an electron transporting layer, a wet film forming method is also preferable.
- the vapor deposition method is not particularly limited and can be appropriately selected from known methods depending on the purpose. Examples thereof include a vacuum vapor deposition method, a resistance heating vapor deposition, a chemical vapor deposition method, and a physical vapor deposition method. Examples of the chemical vapor deposition method include a plasma CVD method, a laser CVD method, a thermal CVD method, and a gas source CVD method.
- the formation of the light-emitting layer by the vapor deposition method may be performed, for example, by vacuum-depositing the organometallic complex, and when the light-emitting layer contains the host material in addition to the organometallic complex, This can be suitably performed by co-evaporating the host material by vacuum evaporation. In the former case, production is easy because co-evaporation is not necessary. is there.
- the wet film forming method is not particularly limited and may be appropriately selected from known methods according to the purpose. Examples thereof include an ink jet method, a spin coat method, a der coat method, a bar coat method, and a blade coat method. , A casting method, a dip method, a curtain coating method and the like.
- a solution in which the material of the light emitting layer is dissolved or dispersed together with a resin component can be used (applied or the like).
- the resin component include polyvinyl carpazole, polycarbonate, and poly. Butyl chloride, polystyrene, polymethyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, butyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester Resins, alkyd resins, epoxy resins, silicone resins, and the like.
- the formation of the light emitting layer by the wet film forming method is performed, for example, by using a solution (coating solution) in which the organometallic complex and the resin material used as necessary are used as a solvent (coating and drying).
- a solution (coating solution) is dissolved in a solvent obtained by dissolving the organometallic complex, the host material and, if necessary, the resin material used in a solvent.
- (coating and drying) it can be suitably performed.
- the thickness of the light emitting layer is not particularly limited and may be appropriately selected depending on the purpose. For example, 1 to 50 nm is preferable, and 3 to 20 nm is more preferable.
- the thickness of the light-emitting layer is within the preferred numerical range, the luminous efficiency, luminous brightness, and color purity of light emitted by the organic EL element are sufficient, and when the thickness is within the more preferred numerical range, it is remarkable. This is advantageous in that One positive electrode
- the positive electrode is not particularly limited and may be appropriately selected depending on the intended purpose. However, the positive electrode may be appropriately selected from the organic thin film layer, and more specifically, when the organic thin film layer has only the light emitting layer.
- the hole transport layer When the organic thin film layer further has the hole transport layer, the hole transport layer
- a layer capable of supplying holes (carrier) to the hole injection layer is preferable.
- the material of the positive electrode is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Among them, a material having a work function of 4 eV or more is preferable.
- Specific examples of the material of the positive electrode include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO); metals such as gold, silver, chromium, and nickel; Mixtures or laminates with conductive metal oxides; inorganic conductive substances such as copper iodide and copper sulfide; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and laminates of these with ITO, etc. . These may be used alone or in combination of two or more. Among these, conductive metal oxides are preferable, and ITO is particularly preferable from the viewpoints of productivity, high conductivity, transparency, and the like.
- the thickness of the positive electrode is not particularly limited and may be appropriately selected depending on the material and the like, but is preferably 1 to 500 nm, more preferably 20 to 200 nm.
- the positive electrode is usually formed on a substrate made of glass such as soda lime glass or non-alkali glass, or a transparent resin.
- the above-mentioned soda lime glass coated with a barrier coat such as the alkali-free glass and silica is preferable from the viewpoint of reducing the ions eluted from the glass.
- the thickness of the substrate is not particularly limited as long as it is a thickness sufficient to maintain mechanical strength, but when glass is used as the base material, it is usually 0.2 mm or more, and 0.7 mm or more. The above is preferred.
- the positive electrode may be formed, for example, by a vapor deposition method, a wet film formation method, an electron beam method, a sputtering method, a reactive sputtering method, an MBE (molecular beam epitaxy) method, a cluster ion beam method, an ion plating method, or a plasma polymerization method (high-frequency excitation ion A coating method of the ITO by a molecular lamination method, a molecular lamination method, a LB method, a printing method, a transfer method, a chemical reaction method (such as a sol-gel method), and the like. it can.
- the positive electrode can be subjected to washing and other processing to lower the driving voltage of the organic EL element and increase luminous efficiency.
- the other treatment for example, when the material of the positive electrode is ITO, a UV-ozone treatment, a plasma treatment and the like are preferably exemplified.
- the negative electrode is not particularly limited and may be appropriately selected depending on the intended purpose. However, the negative electrode may be selected from the organic thin film layer. When the organic thin film layer further has the electron transport layer, electrons are supplied to the electron transport layer, and when the organic thin film layer has an electron injection layer between the organic thin film layer and the negative electrode, electrons are supplied to the electron injection layer. Those that can do so are preferred.
- the material of the negative electrode is not particularly limited, and can be appropriately selected depending on the adhesion between the layer or the molecule adjacent to the negative electrode such as the electron transport layer and the light emitting layer, ionization potential, stability, and the like. Examples thereof include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof.
- the material for the negative electrode include alkali metals (eg, Li, Na, K, Cs, etc.), alkaline earth metals (eg, Mg, Ca, etc.), gold, silver, lead, and aluminum. Alloys, lithium-aluminum alloys or their mixed metals, magnesium-silver alloys or their mixed metals, rare earth metals such as indium, ytterbium, alloys of these, etc. Is mentioned. These may be used alone or in combination of two or more. Among these, a material having a work function of 4 eV or less is preferable, and aluminum, a lithium alloy or a mixed metal thereof, a magnesium silver alloy or a mixed metal thereof, and the like are more preferable.
- the thickness of the negative electrode is not particularly limited and may be appropriately selected depending on the material of the negative electrode and the like, but is preferably 1 to 10, OOOnm, and more preferably 20 to 200 nm.
- the negative electrode may be formed, for example, by a vapor deposition method, a wet film forming method, an electron beam method, a sputtering method, a reactive sputtering method, a MBE (molecular beam epitaxy) method, a clustering method.
- JP2004 / 006329 It can be suitably formed by the above-mentioned methods such as an electron beam method, an ion plating method, a plasma polymerization method (high frequency excitation ion plating method), a molecular lamination method, an LB method, a printing method, and a transfer method. .
- the two or more materials may be simultaneously deposited to form an alloy electrode or the like, or an alloy electrode or the like may be formed by depositing a previously prepared alloy. It may be formed.
- the resistance values of the positive electrode and the negative electrode are preferably low, and are preferably several hundreds ⁇ / port or less.
- the hole injection layer is not particularly limited and may be appropriately selected depending on the intended purpose.
- the hole injection layer preferably has a function of injecting holes from the positive electrode when an electric field is applied. .
- the material for the hole injection layer is not particularly limited and may be appropriately selected depending on the intended purpose.
- a starburst amine [4, 4 ′, 4 ′, (2-naphthylphenylamino) trifluoramine] hereinafter sometimes abbreviated as "2-1 TNATA”
- copper phthalocyanine copper phthalocyanine
- polyaniline polyaniline
- the thickness of the hole injection layer is not particularly limited and may be appropriately selected depending on the purpose.
- the thickness is preferably about 1 to 100 nm, and more preferably 5 to 50 nm.
- the hole injection layer is formed by, for example, a vapor deposition method, a wet film formation method, an electron beam method, a sputtering method, a reactive sputtering method, a MBE (molecular beam epitaxy) method, a cluster method. It can be suitably formed by the above-mentioned methods such as a single ion beam method, an ion plating method, a plasma polymerization method (high frequency excitation plating method), a molecular lamination method, an LB method, a printing method, and a transfer method.
- the hole transport layer is not particularly limited and may be appropriately selected depending on the intended purpose. For example, a layer having a function of transporting holes from the positive electrode when an electric field is applied is preferable.
- the material of the hole transport layer is not particularly limited and may be appropriately selected depending on the intended purpose. , Pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styryl anthracene, phthalenolenone, hydrazone, stinoleben, silazane, styrylamine, aromatic dimethylidin compound, porphyrin compound, polysilane compound, poly (N-vinylcarpazole) ), Aniline-based copolymers, thiophene oligomers and polymers, conductive polymer oligomers and polymers such as polythiophene, and carbon films.
- the hole transport layer and the light emitting layer can be formed.
- aromatic amine compounds are preferable, and specifically, TPD (N, N, diphenyl-1N, N, 1-bis (3-methylphenyl) -1 [1,1, -biphenyl] -1,4,1-diamine) and NPD (N, N, N, Ginaphthyl N, N, Jifueru [1,1,1bihueru] 1,4,4, Jiamin) are more preferable.
- the thickness of the hole transport layer is not particularly limited and may be appropriately selected depending on the intended purpose.
- the thickness is usually 1 to 500 nm, and is 10 to 100 nm. Is preferred.
- the hole transport layer can be formed by, for example, a vapor deposition method, a wet film formation method, an electron beam method, a sputtering method, a reactive sputtering method, a MBE (molecular beam epitaxy) method, a cluster ion beam method, an ion plating method, It can be suitably formed by the above-described methods such as a plasma polymerization method (high frequency excitation plating method), a molecular lamination method, an LB method, a printing method, and a transfer method.
- One hole blocking layer is not particularly limited and may be appropriately selected depending on the intended purpose.
- the thickness is usually 1 to 500 nm, and is 10 to 100 nm. Is preferred.
- the hole transport layer can be formed by, for example, a
- the hole blocking layer is not particularly limited and may be appropriately selected depending on the intended purpose.
- a layer having a function of blocking holes injected from the positive electrode is preferable.
- the material for the hole blocking layer is not particularly limited and can be appropriately selected depending on the purpose.
- the hole blocking layer When the organic EL device has the hole blocking layer, holes transported from the positive electrode side are blocked by the hole blocking layer, and electrons transported from the negative electrode pass through the hole blocking layer. To the light-emitting layer after passing through, the recombination of electrons and holes occurs efficiently in the light-emitting layer. Therefore, the recombination of the holes and the electrons in the organic thin film layer other than the light-emitting layer occurs. Bonding can be prevented, light emission from the target light emitting material can be efficiently obtained, and this is advantageous in terms of color purity and the like.
- the hole blocking layer is preferably disposed between the light emitting layer and the electron transport layer.
- the thickness of the hole blocking layer is not particularly limited and may be appropriately selected depending on the purpose.
- the thickness is usually about 1 to 500 nm, preferably 10 to 50 nm.
- the hole blocking layer may have a single-layer structure or a multilayer structure.
- the hole blocking layer may be formed by, for example, a vapor deposition method, a wet film formation method, an electron beam method, a sputtering method, a reactive sputtering method, a MBE (molecular beam epitaxy) method, a cluster ion beam method, an ion plating method, It can be suitably formed by the above-mentioned methods such as a plasma polymerization method (high-frequency excitation ion plating method), a molecular lamination method, an LB method, a printing method, and a transfer method.
- the electron transport layer is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include a function of transporting electrons from the negative electrode and a function of blocking holes injected from the positive electrode. Are preferred.
- the material of the electron transport layer is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include a quinoline derivative such as the aluminum quinoline complex (A1q), an oxadiazole derivative, a triazole derivative, and a phenanthate. Loline derivatives, perylene derivatives, pyridine derivatives, pyrimidine derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorene derivatives, and the like. When the material of the electron transport layer is mixed with the material of the light emitting layer to form a film, the electric charge is reduced.
- an electron transport layer and a light emitting layer can be formed, and when the material of the hole transport layer is also mixed and formed into a film, an electron transport layer and a hole transport layer and a light emitting layer can be formed.
- Polymers such as carbazole and polycarbonate can be used.
- the thickness of the electron transport layer is not particularly limited and can be appropriately selected depending on the purpose.
- the thickness is usually about 1 to 500 nm, preferably 10 to 50 nm.
- the electron transport layer may have a single-layer structure or a multilayer structure.
- an electron transporting material whose light absorption edge has a shorter wavelength than that of the organometallic complex is used as the electron transporting material used for the electron transporting layer adjacent to the light emitting layer. Is limited to the light emitting layer, and is preferable from the viewpoint of preventing unnecessary light emission from the electron transport layer.
- Examples of the electron transporting material having a light absorption edge shorter in wavelength than the organometallic complex include a phenanthone-containing phosphorus derivative, an oxaziazole derivative, and a triazole derivative, and are represented by the following structural formula (68) 2,9_Dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and the compounds shown below are preferred.
- the electron transporting layer may be formed, for example, by a vapor deposition method, a wet film formation method, an electron beam method, a sputtering method, a reactive sputtering method, MBE (molecular beam epitaxy) method, cluster ion beam method, ion plating method, plasma polymerization method (high frequency excitation ion plating method), molecular lamination method, LB method, printing method, transfer method, etc. It can be suitably formed by a method.
- the material of the electron injection layer is not particularly limited and may be appropriately selected depending on the intended purpose.
- alkali metal fluorides such as lithium fluoride and alkaline earth metal fluorides such as sodium fluoride are used. And the like can be suitably used.
- the thickness of the electron injection layer is not particularly limited and can be appropriately selected depending on the purpose. For example, the thickness is usually about 0.1 to 10 nm, preferably 0.5 to 2 nm.
- the electron injection layer can be suitably formed by, for example, an evaporation method, an electron beam method, a sputtering method, or the like.
- the organic EL device of the present invention may have other layers appropriately selected according to the purpose.
- the other layers include a color conversion layer and a protective layer.
- the color conversion layer preferably contains a phosphorescent material, and more preferably contains the organometallic complex of the present invention. Note that the color conversion layer may be formed only of the organometallic complex, or may be formed containing another material.
- the organometallic complex may be used alone or in combination of two or more.
- an organic molecule excited by light of a certain wavelength emits light from the excited state and transitions to the ground state before being excited by interaction within the molecule or with other molecules. It is known that the excitation and emission wavelengths do not match because some of the energy is lost non-radiatively in the form of thermal energy. The energy difference between the excitation light and the emission is called the Stokes shift.
- the color conversion material used in the color conversion layer a fluorescent material which emits only light from a singlet due to a wide range of material selection has been used.
- the organometallic complex of the present invention is a phosphorescent material, when it is excited by light of a certain wavelength to generate a singlet excited state, it quickly transitions to a triplet excited state, which is a lower energy state.
- the phosphorescent light can be emitted, the Stokes shift is larger than that of the fluorescent material.
- the triplet state is about 0.1 to 2 eV lower than the energy of the singlet excited state.
- the color conversion layer it is better to make the color conversion layer as thin as possible because the material forming the organic EL element is degraded by the exudates of water, for example, residues of water and organic solvent, and the generation of non-light emitting areas is a major problem. .
- the use of a host that absorbs blue light captures the low absorptivity of the guest. It is not necessary to use different materials together, and high color conversion efficiency can be obtained even when used alone.Therefore, light emission from host molecules and color conversion fan It has the advantage that many problems such as reduced manufacturability and increased cost of substrate manufacturing can be solved at the same time.
- concentration quenching when the concentration of the fluorescent light emitting material is too high as described above, the concentration quenching often occurs and the light emission is remarkably weakened. It is known that concentration quenching is less likely to occur as compared with fluorescent light-emitting materials, and there is no restriction on the dispersion concentration. For example, the phosphorescent material emits more light even in a powder state than a fluorescent material. Conversely, if the dispersion concentration is too low, light emission is weakened due to the quenching effect of oxygen molecules. . The effectiveness of using the phosphorescent material in a powder state is that the deterioration of the color conversion layer can be suppressed.
- the color conversion layer Since the color conversion layer is constantly exposed to light during the photolithography process in the substrate fabrication stage, the IT0 patterning process, and in the process of performing color conversion as an element, the reduction in color conversion efficiency due to light degradation becomes a problem.
- a light-emitting material dispersed in a color conversion layer When a light-emitting material dispersed in a color conversion layer is used, the light-emitting material alone is exposed to light, so its deterioration is very fast, and it is very difficult to prevent it.
- a color conversion layer using a phosphorescent material in a powder state is exposed to light with a barta, so that deterioration can be suppressed, a long life, and a color conversion layer that does not change conversion efficiency can be obtained. it can.
- the position where the color conversion layer is provided is not particularly limited and can be appropriately selected depending on the purpose. For example, in the case of performing full color display, it is preferable to provide the color conversion layer on a pixel. Good.
- the color conversion layer is capable of converting incident light into light having a wavelength longer than that of the light by 100 nm or more. More preferably, it can be converted to light having a wavelength longer than that of the light by 150 nm or more.
- the color conversion layer be capable of converting light in a wavelength range from ultraviolet light to blue light to red light.
- the method for forming the color conversion layer is not particularly limited and can be appropriately selected depending on the intended purpose. Examples thereof include a vapor deposition method and a coating method.
- a known color filter may be used as the color conversion layer.
- the protective layer is not particularly limited and can be appropriately selected depending on the purpose. For example, molecules or substances such as moisture and oxygen that accelerate the deterioration of the organic EL element enter the organic EL element. What can suppress that is preferable.
- the material of the protective layer for example, I n, S n, P b, Au, Cu, Ag, A 1, T i, metals such as N i, MgO, S i O , S i 0 2, A 1 2 0 3, Ge O, N i O, C a O, B A_ ⁇ , F e 2 0 3, Y 2 0 3, T i 0 metal oxides such as 2, S i N, S iN x 0 y , etc.
- metals such as N i, MgO, S i O , S i 0 2, A 1 2 0 3, Ge O, N i O, C a O, B A_ ⁇ , F e 2 0 3, Y 2 0 3, T i 0 metal oxides such as 2, S i N, S iN x 0 y , etc.
- nitride Mg F 2, L i F , a 1 F 3, C a F 2 or the like of metal off Tsu fluoride, polyethylene, polypropylene, polymethyl methacrylate Tari rate, polyimide, polyurea, polytetrafluoroethylene full O b ethylene, Polychloroethylene trifluoroethylene, polydichloroethylene difluoroethylene, black ethylene trifluorene copolymer, ethylene and dichlorodifluoroethylene, monomer mixture containing tetrafluoroethylene and at least one comonomer Copolymer obtained by polymerization, fluorinated copolymer having a cyclic structure in the copolymer main chain, water absorption of 1% or more Sex substances, such as water absorption 0.1% or less of the moisture-proof materials.
- the protective layer may be formed, for example, by a vapor deposition method, a wet film forming method, a sputtering method, a reactive sputtering method, an MBE (molecular beam epitaxy) method, a cluster ion beam method, an ion plating method, a plasma polymerization method (high-frequency excitation ion plating). Ting method ), Printing method, transfer method, etc.
- the layer configuration in the organic EL device of the present invention is not particularly limited and can be appropriately selected depending on the purpose.
- the following layer configurations (1) to (13) namely, (1) positive electrode (2) Positive hole injection layer / hole transport layer Z light emitting layer Z electron transport layer / negative electrode, (3) Positive electrode z hole transport layer / light emitting layer / electron transport layer / electron injection layer Z negative electrode, (4) positive electrode / hole transport layer / light emitting layer / electron transport layer / negative electrode, (5) positive electrode / hole injection layer / (6) positive electrode / hole injection layer Z hole transport layer Z light emitting layer / electron transport layer / negative electrode, (7) positive electrode Z hole transport Layer / light emitting layer / electron transport layer Z electron injection layer / negative electrode, (8) positive electrode hole transport layer / light emitting layer / electron transport layer / negative electrode, (9) positive electrode / hole injection layer / hole transport layer / light emitting layer Layer Z electron transport layer Z electron injection layer / negative electrode, (10) positive electrode / hole injection
- Preferable examples include a Z negative electrode, (12) a positive electrode Z hole transport layer / light emitting layer / electron transport layer / negative electrode, and (13) a positive electrode Z hole transport layer / light emitting layer / electron transport layer / negative electrode.
- the hole blocking layer is disposed between the light emitting layer and the electron transport layer.
- a layer configuration is preferably exemplified.
- FIG. 1 shows an embodiment of the above (4) positive electrode Z hole transport layer / light emitting layer / electron transport layer / negative electrode.
- the organic EL element 10 is a glass substrate 12
- a positive electrode 14 for example, an ITO electrode
- a hole transport layer 16 for example, a light-emitting layer 18, an electron transport layer 20, and a negative electrode 22 (for example, an A 1 -Li electrode) formed thereon are It has a layered structure laminated in this order.
- the positive electrode 14 (for example, an ITO electrode) and the negative electrode 22 (for example, an A1-Li electrode) are connected to each other via a power supply.
- the organic thin film layer 24 is formed by the hole transport layer 16, the light emitting layer 18 and the electron transport layer 20.
- the brightness half-source time of the organic EL device of the present invention longer Preferably, for example, in the continuous drive of the current density 5 O AZM 2, preferably not less than 5 hours, 2 0 hours or more , More preferably 40 hours or more, and particularly preferably 60 hours or more.
- the emission peak wavelength of the organic EL element of the present invention is not particularly limited and can be appropriately selected from visible light castles. For example, 600 to 65 nm is preferable.
- the organic EL device of the present invention emits light at a voltage of 10 V or less, preferably emits at 8 V or less, and more preferably emits at 7 V or less.
- the current efficiency of the organic EL device of the present invention is preferably 10 cd ZA or more at a current density of 5 A / m 2 , more preferably 30 cd / A or more, and 40 cd / A or more.
- the above is particularly preferred.
- the organic EL device of the present invention includes, for example, a computer, an in-vehicle display, an outdoor display, a household device, a business device, a household appliance, a traffic display, a clock display, a calendar display, and a luminescent device. Although it can be suitably used in various fields such as screens and audio equipment, it can be particularly suitably used for lighting devices and the following organic EL displays of the present invention.
- the organic EL display of the present invention is not particularly limited except that the organic EL element of the present invention is used, and a known configuration can be appropriately adopted.
- the organic EL display may be of a single-color emission type, of a multi-color emission type, or of a full-color type.
- the organic EL display As a method for making the organic EL display a full-color type, for example, as described in “Monthly Display”, September 2000, pages 33 to 37, three primary colors ( An organic EL element that emits light corresponding to blue (B), green (G), and red (R)) is arranged on a substrate.
- a color conversion method of converting blue light emitted by an organic EL element for blue light emission into red (R) and green (G) through a fluorescent dye layer Since the organic EL device of the present invention is used for emitting red light or the like, a three-color emission method, Method or the like can be suitably adopted.
- the color conversion method can be particularly preferably employed.
- this organic EL display has a blue light emitting electrode 25 disposed on an electrode 25 corresponding to a pixel.
- the organic thin film layer 30 is provided on one surface, and further has a transparent electrode 20 thereon. Then, on the transparent electrode 20, through a protective layer (planarizing layer) 15, a laminate of the color conversion layer 60 for red and the red color filter 65 and the color conversion layer 7 for green 0 and a laminate of green color filters 80 are arranged. Then, a glass substrate 10 is provided on these.
- the organic thin film layer 30 for emitting blue light emits blue light. Part of this blue light emission passes through the transparent electrode 20, passes through the protective layer 15 and the glass substrate 10 as it is, and is emitted to the outside.
- the red color conversion layer 60 and the green color conversion layer 70 exist the blue light emission is converted into red and green in these color conversion layers, respectively, and further, the red color
- the light passes through the filter 65 and the green color filter 80, they emit red light and green light, respectively, and pass through the glass substrate 10.
- the organic EL display can perform full-color display.
- FIG. 3 is a diagram showing a structural example of an organic EL display by a three-color light emitting method
- FIG. 4 is a diagram showing a structural example of an organic EL display by a white light method. Reference numerals in FIGS. 3 and 4 mean the same as those in FIG.
- the organic EL element of the present invention in order to manufacture a full-color organic EL display by the 3 ′ color emission method, for example, when the organic EL element of the present invention is used for emitting red light, It may be used for light emission of other colors. The color may be formed by the organic EL element of the present invention.) In addition, an organic EL element for emitting green light and an organic EL element for emitting blue light are required.
- the organic EL device for emitting blue light is not particularly limited and can be appropriately selected from known devices.
- the layer configuration is ITO (positive electrode). Negative electrode) and are preferably mentioned.
- the organic EL device for emitting green light is not particularly limited and can be appropriately selected from known devices.
- the layer configuration is ITO (positive electrode) / NPD / A1q / A 1 -Li (negative electrode), and the like are preferred.
- the mode of the organic EL display is not particularly limited and can be appropriately selected according to the purpose.
- “Nikkei Electronitas”, No. 765, March 13, 2000, 55- Preferable examples include a passive matrix panel and an active matrix panel as described on page 62.
- the passive matrix panel has, for example, as shown in FIG.
- a band-shaped positive electrode 14 for example, an ITO electrode
- a strip-shaped organic thin-film layer 24 for red light emission, an organic thin-film layer 26 for blue light emission, and an organic thin-film layer 28 for green light emission arranged in parallel to the cathode 14 and in a direction substantially perpendicular to the positive electrode 14.
- a negative electrode 22 having the same shape as these is provided.
- a circuit is formed in which a positive electrode line 30 composed of a plurality of positive electrodes 14 and a negative electrode line 32 composed of a plurality of negative electrodes 22 cross each other in a substantially perpendicular direction.
- a positive electrode line 30 composed of a plurality of positive electrodes 14
- a negative electrode line 32 composed of a plurality of negative electrodes 22 cross each other in a substantially perpendicular direction.
- Each of the organic thin-film layers 24, 26, and 28 for red, blue, and green light located at each intersection functions as a pixel, and there are a plurality of organic EL elements 34 corresponding to each pixel. .
- the passive matrix panel when a current is applied to one of the positive electrodes 14 in the positive electrode line 30 and one of the negative electrodes 22 in the negative electrode line 32 by the constant current source 36, the organic A current is applied to the EL thin film layer, and the organic EL thin film layer at that position emits light. By controlling the light emission of each pixel, a full-color image can be easily formed.
- the active matrix panel for example, as shown in FIG. 7, scanning lines, data lines, and current supply lines are formed in a grid pattern on a glass substrate 12, and the scanning lines forming a grid pattern are formed.
- a positive electrode 14 (for example, an ITO electrode) that can be driven by the TFT circuit 40 and is disposed in each of the grids.
- a negative electrode 22 is disposed on the organic thin film layer 24 for emitting red light, the organic thin film layer 26 for emitting blue light, and the organic thin film layer 28 for emitting green light.
- the organic thin film layer 24 for red light emission, the organic thin film layer 26 for blue light emission, and the organic thin film layer 28 for green light emission are respectively a hole transport layer 16, a light emitting layer 18 and an electron transport layer 20. have.
- a plurality of parallel scanning lines 46 and a plurality of parallel data lines 42 and current supply lines 44 are orthogonal to each other.
- a switching TFT 48 and a driving TFT 50 are connected to form a circuit.
- each of the organic thin-film elements 24, 26, and 28 for blue light emission, green light emission, and red light emission functions as a pixel, and in the active matrix panel, the stripes are arranged in a horizontal direction.
- the organic EL display of the present invention is, for example, a television, a mobile phone, a computer, an in-vehicle display, an outdoor display, a household device, a business device, a household appliance, a traffic display, a clock display, and a calendar display. , Luminescent screen, audio equipment, and the like.
- Synthesis Example 1 Synthesis of Pt (3,5-di (2-pyridyl) toluene) (bifluo-loxoside) (hereinafter referred to as “Pt (dpt) (obp)”)
- Pt (3,5-di (2-pyridyl) toluene) (biperoxide) (hereinafter referred to as “Pt (dpt) (obp)”) was synthesized as follows. That is, specifically, 3,5-dibromotoluene (5.0 g; 20 mmo 1), 2-tree n-butylstannylpyridine (26.9 g; 73 mmo 1), and bis ( Trihue Nilphosphine) Palladium. Dichloride (1.55 g; 2.2 mmo 1) and lithium chloride (11.7 g; 276 mmo 1) in 130 ml of toluene Refluxed for 2 days.
- FIG. 9 shows the IR spectrum of P t (dpt) (obp).
- Pt (dpt) C1 was obtained in the same manner as in Synthesis Example 1, the obtained Pt (dt) CI10Omg (0.21 mmo1) was put in acetone 3 Om1 and stirred. To this, 29 mg (0.32 mmo 1) of 1,2,4-triazole'sodium salt was added, and the mixture was stirred at room temperature for 10 minutes. After a few drops of pure water, a yellow solid began to precipitate. Stir for 3 hours while heating, allow to cool, collect the precipitated solid by filtration, wash well with pure water, methanol, and getyl ether in order, and dry in vacuo to obtain Pt (dpt) (taz) yellow. A solid was obtained. The yield was 82%. The IR spectrum of P t (dpt) (taz) is shown in FIG.
- Synthesis Example 4 Synthesis of Pt (3,5-di (2-pyridyl) toluene) (benzothiazolone 2-thiolate) (hereinafter referred to as ⁇ t (dpt) (sbtz) J) After obtaining Pt (dpt) C1, the obtained Pt (dpt) CI10Omg (0.21 mmo1) and 2 _ Menolecaptobenzozothiazole were obtained in 100 ml of three-phase flask.42. 1 mg (0.25 mmo 1) and 0 ml of DMS03 were added and stirred in a nitrogen atmosphere.
- Pt (diqt) Cl 5-Di (1-isoquinolyl) toluene) Cl
- the yield was 42% by mass.
- the synthesis of Pt (diqt) (obp) was performed in the same manner as the synthesis of Pt (dpt) (obp), except that Pt (dpt) CI was replaced with Pt (diqt) CI. However, Pt (diqt) (obp) was obtained as an orange powder. The yield was 83%.
- Pt (3,5-di (1-isoquinolyl) toluene) C1 (hereinafter referred to as "Pt (diqt) Cl") was synthesized in the same manner as in Synthesis Example 5.
- the obtained Pt (diqt) C1lOOmg (0.21 mmo1) was put in Acetone 3Om1 and stirred.
- 56 mg (1 mmo 1) of KOH powder was added and stirred at room temperature for 10 minutes. After a few drops of pure water, a yellow solid began to precipitate.
- Synthesis Example 8 Synthesis of Pt (3,5-di (1-isoquinolyl) toluene) (benzothiazole-2-thiolate) (hereinafter referred to as "1: ((1 1 1;) (sbtz)”)
- Pt (diqt) Cl Pt (3,5-di (1-1 ⁇ soquinolyl) toluene) C1 (hereinafter referred to as "Pt (diqt) Cl") in the same manner as in Synthesis Example 5, 10 Om1 During the course, the obtained Pt (diqt) CI l O Omg (0.21 mm o 1), 2-mercaptobenzothiazole 42.1 mg (0.25 mm o 1) and DMS O 3 Om l And stirred in a nitrogen atmosphere. To this, 200 mg (5 mmo 1) of NaOH powder was added, refluxed for 5 hours, allowed to cool, and a large amount of pure water was added.
- 3,5-Di (2-pyridyl) toluene was prepared in the same manner as in the synthesis of 3,5-di (2-pyridyl) toluene, except that 3,5-bromotoluene was replaced with 3,5-bromopyridine in Synthesis Example 1.
- Pt (3,5-di (2-pyridyl) pyridine) Cl (hereinafter referred to as "Pt (dppr) Cl") was synthesized in the same manner as in Synthesis Example 9.
- the obtained Pt (dppr) C110Omg (0.21 mmo1) was put in Acetone 3Om1 and stirred. here Then, 0 «[powder 56111 ⁇ (lmmo 1) was added thereto, and the mixture was stirred at room temperature for 10 minutes. A few drops of pure water were added and a yellow solid began to precipitate.
- Synthesis Example 1 1 Synthesis of Pt (3,5-di (2-pyridyl) pyridine) (1,2,4-triazolate) (hereinafter referred to as “Pt (dppr) (taz)”) Pt (3,5-di (2-pyridyl) pyridine) C1 (hereinafter referred to as “Pt (dppr) Cl”) was synthesized in the same manner as in 9.
- the obtained Pt (dppr) C1lOOmg (0.21 mmo1) was put in 30 ml of acetone and stirred.
- 29 mg (0.32 mmo 1) of 1,2,4-triazole'sodium salt was added, and the mixture was stirred at room temperature for 10 minutes.
- Pt (dppr) Cl Pt (3,5-di (2-pyridyl) pyridine) C1 (hereinafter referred to as "Pt (dppr) Cl") in the same manner as in Synthesis Example 9, the mixture was placed in a 100 ml three-neck flask. Then, the obtained Pt (dppr) CI l O Omg (0.21 mm o 1), 2-mercaptobenzothiazole 42.1 mg (0.25 mm o 1), and DMS03 0 ml were added. The mixture was stirred in a nitrogen atmosphere. To this, 200 mg (5 mmo 1) of NaOH powder was added, refluxed for 5 hours, allowed to cool, and a large amount of pure water was added.
- Pt (dpt) CllO Omg (0.21 mmo 1) was placed in 30 ml of acetone and stirred.
- sodium in methanol 20 m 1 full enoki Sai de ⁇ 3 ⁇ 2 0 5 3 mg of (0. 32 mm o 1) was slowly litho dropwise. Stirred at room temperature for 10 minutes. The reaction proceeded with the addition of a few drops of pure water, and a pale yellow solid began to precipitate. The mixture was stirred for 3 hours while heating. After allowing to cool, the precipitated pale yellow solid was collected by filtration, washed well with pure water, methanol and getyl ether in that order, and dried in vacuo. Pt (dpt) (oph) was obtained as a pale yellow solid. The yield was 80%.
- Pt (dpt) (obp) synthesized in Synthesis Example 1 was synthesized on a quartz glass substrate by co-evaporation to obtain a thin film (luminescent solid) doped with 2% of CBP at a deposition rate ratio of 50 nm to a thickness of 50 nm. did.
- the PL (photoluminescence) quantum yield of this thin film (luminescent solid) was determined using the aluminum quinoline complex (Alq3) thin film (PL quantum yield: 22%) with known PL quantum yield as a reference. It was determined by measurement. That is, a thin film sample on a transparent substrate was irradiated obliquely with excitation light (365 nm steady light) from a light source.
- the number of PL photons [sample (sample)] was calculated by conversion from the PL spectrum of a thin film measured using a spectral radiance meter (CS-100, manufactured by Minolta). At the same time as the luminescence measurement, the total intensity [/ (sample)] of the excitation light transmitted and reflected from the sample was detected by the photodiode. Next, the same measurement is performed on the reference A1q3 thin film to determine the number of PL photons [ref. (Ref.)] Of the reference and the total intensity [/ (ref)] of the transmitted and reflected excitation light. Was. Next, the total intensity [/ (substrate)] of the transmitted and reflected excitation light only from the transparent substrate was measured.
- the PL quantum yield of the sample thin film can be calculated by the following equation.
- the organometallic complex as a luminescent material was converted from Pt (dpt) (obp) to the organic
- the quantum yield of phosphorescence of the formed thin film (luminescent solid) was measured under the same conditions as in Example 1 except that the metal complex was replaced. The results are shown in Table 1.
- a stacked organic EL device was produced. That is, the hole of the glass substrate with I TO electrodes, water, acetone, washed with isopropyl alcohol, a vacuum vapor deposition apparatus (1 X 1 0 one 4 P a, the substrate temperature is room temperature) using, on the I TO 4, 4 ', 4,, tri- (2-naphthylphenylamino) triphenylamine (2-TNA) TA) was formed to a thickness of 140 nm.
- the TPD having a thickness of 10 nm was formed as a hole transport layer on the hole injection layer.
- a hole transport layer a light emitting layer in which Pt (dpt) (obp) was doped with 2% of the above-mentioned CBP at a deposition rate ratio of 30 nm was formed.
- the BCP was formed as a hole blocking layer to a thickness of 20 nm.
- A1q was formed to a thickness of 20 nm as an electron transporting layer.
- LiF was deposited on the electron transporting layer to a thickness of 0.5 nm, and finally aluminum was deposited to a thickness of 100 nm and sealed in a nitrogen atmosphere.
- An organic EL device was produced under the same conditions as in Example 16 except that Pt (dpt) (obp) as the light emitting material was replaced with the organometallic complex shown in Table 2.
- Pt (dpt) (obp) as the light emitting material was replaced with the organometallic complex shown in Table 2.
- a voltage was applied to these organic EL elements using ITO as a positive electrode and an aluminum electrode as a negative electrode, and EL characteristics were measured.
- Table 2 shows the voltage, emission peak wavelength, and current efficiency at a current density of 5 AZm 2 .
- an organic EL device was manufactured. That is, a glass substrate with an ITO electrode was washed with water, acetone, and isopropyl alcohol, and a poly (3,4-ethylenedioxythiophene) was formed as a hole injection layer on the ITO by I spin coating. A polystyrenesulfonate thin film (PEDOT: PSS thin film) was formed to a thickness of 50 nm and dried by heating at 200 ° C for 2 hours.
- PEDOT PSS thin film
- a light emitting layer in which 3% of Pt (dpt) (obp) is dispersed in polybutyl carpasol (PVK) is applied by spin coating to a thickness of 35 nm, and formed.
- Beta at 120 ° C for 2 hours.
- the BCP was formed to a thickness of 20 nm as a hole blocking layer on the light emitting layer.
- A1q was formed to have a thickness of 20 nm as an electron transporting layer.
- the organic EL device manufactured in Example 16 was continuously driven at a current density of 50 A / m 2 , and a change in light emission luminance was examined.
- the luminance half-life from an initial luminance of 2365 cd / m 2 was 70 hours.
- the organic EL device manufactured in Example 17 was continuously driven at a current density of 50 A / m 2 , and a change in light emission luminance was examined. Luminance half-life from the initial luminance 2365 c DZM 2 was 70 hours.
- the organic EL device manufactured in Example 18 was continuously driven at a current density of 50 A / m 2 , and a change in light emission luminance was examined.
- the luminance half life from the initial luminance of 2412 cd / m 2 was 75 hours.
- the organic EL device manufactured in Example 19 was continuously driven at a current density of 50 A / m 2 , and a change in light emission luminance was examined. Luminance half-life from the initial luminance 2055 c DZM 2 was 60 hours.
- An organic EL device was fabricated under the same conditions as in Example 14 except that the light emitting material was changed from Pt (dpt) (obp) to Pt (dpt) CI in Example 16.
- the obtained organic EL device was continuously driven at a current density of 50 A / m 2 , and a change in light emission luminance was examined. Luminance half-life from the initial luminance 1 877 cd / m 2 is rarely in just 0.3 h.
- Synthesis Example 15 Synthesis of Pt (1,3-dipyrazolylbenzene) (phenoxide) (hereinafter referred to as “Pt (dpzb) (oph)”)
- Pt (dpzb) CI44Omg (1 mmo1) was placed in 150 ml of acetone and stirred. Here, it was slowly added dropwise sodium in methanol 1 00m 1 Hue Roh Kisaido ⁇ 3 ⁇ 2 0 272 mg (1. 6 mm o 1). The mixture was stirred at room temperature for 10 minutes. The reaction proceeded with the addition of a few drops of pure water, and a pale yellow solid began to precipitate. The mixture was stirred for 3 hours while heating. After allowing to cool, the precipitated pale yellow solid was collected by filtration, washed well with pure water, methanol and getyl ether in that order, and vacuum dried to obtain 40 mg of Pt (dpzb) (oph). .
- Pt (fdpb) (oph) was synthesized in the same manner as in Synthesis Example 1, except that 3,5-dibromotoluene was replaced with 1,3-dibu-mouth 5-fluorobenzene in Synthesis Example 1. .
- Pt (dpt) (pdph) was synthesized in the same manner as in Synthesis Example 3 except that 1,2,4-triazole'sodium salt was replaced with lithium'diphenylphosphide in Synthesis Example 3. .
- Example 3 Under the same conditions as in Example 1 except that the organometallic complex as the light emitting material was changed from Pt (dpt) (obp) to the organometallic complex shown in Table 3, the phosphorous of the formed thin film (luminescent solid) was changed. The quantum yield of light emission was measured. Table 3 shows the results. Table 3
- Example 16 An organic EL device was produced under the same conditions as in Example 16 except that the light emitting materials in Example 16 were changed as shown in Table 4. A voltage was applied to these devices using ITO as a positive electrode and an aluminum electrode as a negative electrode, and EL characteristics were measured. Table 4 shows the voltage, emission peak wavelength, and current efficiency when the current density was 5 AZm 2 . Table 4 Emitting materials Voltage (V) Emission peak wavelength (nm) Current efficiency (cd / A) Example 40 Pt (dpzb) (oph) 6. 4 430 12.8
- an organic metal complex which solves the above-mentioned conventional problems, emits phosphorescence, is suitable as a light-emitting material or a color conversion material in an organic EL device or a lighting device, etc .; a luminescent solid; Uses a luminescent solid, has excellent life, luminous efficiency, thermal and electrical stability, and has a long drive life.
- Organic EL device that uses this organic EL element for high performance, long life, and average drive current It is possible to provide an organic EL display having a long driving life, which is suitable for a full-color display or the like having a good color balance without changing the light-emitting area, regardless of the light-emitting area.
- the organometallic complex or luminescent solid of the present invention emits phosphorescent light and can be suitably used as a luminescent material or a color conversion material in an organic EL device, a lighting device, or the like.
- the organic EL element of the present invention uses the organometallic complex, it has excellent life, luminous efficiency, thermal and electrical stability, color conversion efficiency, etc., has a long driving life, and can be used in computers, on-vehicle displays, Suitable for use in various fields including outdoor display, household equipment, business equipment, home appliance, traffic display, clock display, calendar display, luminescent screen, audio equipment, etc.
- the present invention can be particularly suitably used for lighting devices and the following organic EL displays of the present invention.
- the organic EL display of the present invention uses the organic EL element, it has high performance and long life, and is used for televisions, mobile phones, computers, in-vehicle displays, outdoor displays, household appliances, commercial appliances, and home appliances. It can be suitably used in various fields including devices, traffic indicators, clock indicators, calendar indicators, luminescent screens, audio equipment, and the like.
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Abstract
Description
Claims
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JP2006512711A JP4880450B2 (ja) | 2004-04-30 | 2004-04-30 | 有機金属錯体、発光性固体、有機el素子及び有機elディスプレイ |
CN2004800429219A CN1984889B (zh) | 2004-04-30 | 2004-04-30 | 有机金属络合物、发光性固体、有机el元件及有机el显示器 |
US11/579,179 US20070224447A1 (en) | 2004-04-30 | 2004-04-30 | Organometallic Complex, Luminescent Solid, Organic el Element and Organic el Display |
PCT/JP2004/006329 WO2005105746A1 (ja) | 2004-04-30 | 2004-04-30 | 有機金属錯体、発光性固体、有機el素子及び有機elディスプレイ |
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EP1667493A1 (en) * | 2004-11-04 | 2006-06-07 | Fuji Photo Film Co., Ltd. | Organometallic complex, light-emitting solid, organic electroluminescent element and organic electroluminescent display |
US8106199B2 (en) | 2007-02-13 | 2012-01-31 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Organometallic materials for optical emission, optical absorption, and devices including organometallic materials |
CN102617614A (zh) * | 2004-12-28 | 2012-08-01 | 住友化学株式会社 | 高分子化合物及使用该高分子化合物的元件 |
US8389725B2 (en) | 2008-02-29 | 2013-03-05 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Tridentate platinum (II) complexes |
US8846940B2 (en) | 2007-12-21 | 2014-09-30 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Platinum (II) di (2-pyrazolyl) benzene chloride analogs and uses |
US9444063B2 (en) | 2013-05-16 | 2016-09-13 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, electronic device, and lighting device |
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US20200052229A1 (en) * | 2017-04-19 | 2020-02-13 | The University Of Hong Kong | Dendrimers containing luminescent platinum(ii) compounds for organic light-emitting devices and their preparation |
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KR102395784B1 (ko) | 2017-03-27 | 2022-05-10 | 삼성전자주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
KR20180109735A (ko) * | 2017-03-27 | 2018-10-08 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물 |
Also Published As
Publication number | Publication date |
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CN1984889B (zh) | 2011-08-24 |
US20070224447A1 (en) | 2007-09-27 |
JPWO2005105746A1 (ja) | 2008-03-13 |
JP4880450B2 (ja) | 2012-02-22 |
CN1984889A (zh) | 2007-06-20 |
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