WO2021152940A1 - Composé, élément électroluminescent à couche mince organique, dispositif d'affichage, et dispositif d'éclairage - Google Patents

Composé, élément électroluminescent à couche mince organique, dispositif d'affichage, et dispositif d'éclairage Download PDF

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WO2021152940A1
WO2021152940A1 PCT/JP2020/040397 JP2020040397W WO2021152940A1 WO 2021152940 A1 WO2021152940 A1 WO 2021152940A1 JP 2020040397 W JP2020040397 W JP 2020040397W WO 2021152940 A1 WO2021152940 A1 WO 2021152940A1
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light emitting
layer
compound
derivatives
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徳田貴士
長尾和真
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東レ株式会社
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Priority to KR1020227024572A priority Critical patent/KR102618174B1/ko
Priority to JP2020560846A priority patent/JP7052885B2/ja
Priority to CN202080082975.7A priority patent/CN114746402A/zh
Publication of WO2021152940A1 publication Critical patent/WO2021152940A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/19—Tandem OLEDs

Definitions

  • the present invention relates to a compound having a specific structure, and an organic thin film light emitting device, a display device, and a lighting device using the compound.
  • organic thin-film light-emitting devices have been steadily put into practical use, such as being used in displays for televisions and smartphones.
  • organic thin film light emitting devices there are still many technical problems with existing organic thin film light emitting devices. Above all, achieving both high-efficiency light emission and long life of the organic thin-film light-emitting element has become a major issue.
  • fluoranthene derivatives having a fluoranthene skeleton and an aromatic heterocyclic group containing electron-accepting nitrogen see, for example, Patent Document 1
  • a pyrene skeleton and an aryl group or a heteroaryl group have been used so far.
  • Patent Document 2 and Non-Patent Document 1 a compound having a cyano group and a heteroaryl group (see, for example, Patent Document 3), an aromatic heterocycle containing a triphenylene skeleton and electron-accepting nitrogen.
  • Compounds having and see, for example, Patent Document 4 have been developed.
  • Patent Documents 1 and 2 and Non-Patent Document 1 a compound having a specific structure in which a nitrogen-containing aromatic heterocycle is linked with fluoranthene or pyrene enhances luminous efficiency, enables low-voltage drive, and has excellent durability.
  • a thin film light emitting element can be obtained.
  • Patent Documents 3 to 4 disclose that an organic thin film light emitting device having excellent durability can be obtained by a compound having a specific structure having a cyano group, a triphenylene skeleton and a nitrogen-containing aromatic heterocycle.
  • the luminous efficiency and durability required for organic thin-film light emitting devices have been increasing more and more, and there is a demand for a technology that achieves both higher luminous efficiency and durable life.
  • An object of the present invention is to provide an organic thin film light emitting device having excellent luminous efficiency and durable life in view of the problems of the prior art.
  • the present invention is a compound represented by the following general formula (1).
  • any one of X 1 ⁇ X 3 is a nitrogen atom, and the other is a methine group.
  • L 1 is a substituted or unsubstituted biphenylene group, a terphenylene group, a naphthylene group, a quarter phenylene group, a dimethylfluoreneylene group, a diphenylfluorenylene group or a spirobifluoreneylene group.
  • the substituent is an alkyl group or an alkoxy group.
  • A is a phenanthrenyl group, a pyrenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group or a spirobifluorenyl group.
  • the present invention is not limited to the following embodiments, and can be variously modified and implemented according to an object and an application.
  • any one of X 1 to X 3 is a nitrogen atom, and the other is a methine group.
  • L 1 is a substituted or unsubstituted biphenylene group, a terphenylene group, a naphthylene group, a quarter phenylene group, a dimethylfluoreneylene group, a diphenylfluorenylene group or a spirobifluoreneylene group.
  • the substituent is an alkyl group or an alkoxy group.
  • A is a phenanthrenyl group, a pyrenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group or a spirobifluorenyl group.
  • substitution or unsubstituted means that a hydrogen atom is bonded, and “substitution” means that at least a part of a hydrogen atom is substituted. .. The same applies to the case of "substituted or unsubstituted” in the compound described below or its partial structure.
  • the alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group and a tert-butyl group, which are substituents. May or may not have.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 or more and 20 or less, more preferably 1 or more and 8 or less, from the viewpoint of availability and cost.
  • the alkoxy group refers to a group in which an alkyl group is bonded to oxygen, such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a tert-butoxy group. It may or may not have a substituent.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is usually in the range of 1 or more and 20 or less, more preferably 1 or more and 8 or less, from the viewpoint of availability and cost.
  • Patent Documents 1 to 4 and Non-Patent Document 1 describe compounds X, Y, Z, V represented by the following formulas. W is shown.
  • a compound having a fluoranthenyl group such as compound X has a high driving voltage, and still has problems in luminous efficiency and durable life.
  • a compound in which a nitrogen-containing aromatic heterocycle and a polycyclic aromatic hydrocarbon are linked by a phenylene group, such as compound Y has a small effect of improving the intermolecular interaction by the linking group, so that the driving voltage is sufficiently lowered. It was difficult to do so, and there were problems in light emission efficiency and durable life.
  • the LUMO level becomes too deep due to the cyano group, so that the driving voltage becomes high, and there are problems in luminous efficiency and durable life.
  • a compound having a plurality of pyrenyl groups such as compound V and a compound having a triphenylenyl group such as compound W tend to crystallize in an element due to their high crystallinity, and have problems in durability life and drive stability.
  • Compound represented by the general formula (1) introduces a larger linking group having a molecular weight than a phenylene group in L 1.
  • the interaction between the molecules is enhanced, and the horizontal orientation of the vapor-deposited film is facilitated. Due to these effects, the charge transport property can be further increased, the drive voltage can be reduced, and the luminous efficiency can be improved. Further, by increasing the intermolecular interaction, the glass transition temperature can be increased and the durable life can be improved.
  • a high charge is obtained by selecting a phenanthrenyl group, a pyrenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group or a spirobifluorenyl group having high flatness and large overlap between molecules. Since it has transportability, it can be driven at a low voltage and the luminous efficiency can be improved.
  • the compound represented by the general formula (1) has a large electron transport property. Further, since it has a flexible structure composed of a plurality of pyridyl groups, it has a large coordinating property to a metal atom. Therefore, when the compound represented by the general formula (1) is used as the organic layer in the light emitting device, a stable layer can be formed. In particular, when the organic layer is an electron transport layer, an electron injection layer or a charge generation layer, these layers are more stable and exhibit excellent performance.
  • any one of X 1 to X 3 is a nitrogen atom, and the other is a methine group. It is preferable that X 3 is a nitrogen atom from the viewpoint of enhancing the coordination with the metal atom and forming a more stable layer. By forming a more stable ligand layer, it can be driven at a low voltage and the durable life can be further improved.
  • L 1 is a substituted or unsubstituted biphenylene group, turphenylene group, naphthylene group, quarter phenylene group, dimethylfluorenylene group, diphenylfluorenylene group or spirobifluoreneylene group.
  • L 1 is these groups, as described above, the interaction between the molecules becomes high, and the charge transport property and the film quality stability can be made higher.
  • L 1 is preferably a substituted or unsubstituted biphenylene group, a terphenylene group, or a naphthylene group, and more preferably a substituted or unsubstituted biphenylene group.
  • the substituent is an alkyl group or an alkoxy group. These substituents are preferable because they can improve the stability of the compound without lowering the charge transport property of the compound.
  • A is a phenanthrenyl group, a pyrenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group or a spirobifluorenyl group. From the viewpoint of further improving the luminous efficiency and the durable life, A is preferably a pyrenyl group.
  • Examples of the compound represented by the above general formula (1) include the compounds shown below. The following is an example, and even if the compound is not specified here, it is similarly preferably used as long as it is represented by the general formula (1).
  • the compound represented by the general formula (1) can be synthesized by a known synthetic method.
  • Examples of the synthesis method include, but are not limited to, a coupling reaction between an aryl halide derivative using palladium and an arylboronic acid derivative.
  • the compound represented by the general formula (1) is preferably used as a light emitting device material.
  • the light emitting device material in the present invention represents a material used for any layer of the light emitting device, and as described later, is used for a hole injection layer, a hole transport layer, a light emitting layer, and / or an electron transport layer.
  • the materials used for the protective film (cap layer) of the electrodes are also included.
  • the organic thin film light emitting device has an anode and a cathode, and an organic layer interposed between the anode and the cathode, and the organic layer emits light by electric energy.
  • the layer structure between the anode and the cathode in such an organic thin film light emitting element includes 1) a light emitting layer / an electron transporting layer, 2) a hole transporting layer / a light emitting layer, and 3) positive, in addition to the structure consisting of only a light emitting layer.
  • Hole transport layer / light emitting layer / electron transport layer 4) hole injection layer / hole transport layer / light emitting layer / electron transport layer, 5) hole transport layer / light emitting layer / electron transport layer / electron injection layer, 6) Lamination such as hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer, 7) hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer
  • the configuration can be mentioned.
  • tandem type in which a plurality of the above laminated configurations are laminated via an intermediate layer may be used.
  • the intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and a known material structure can be used.
  • Specific examples of the tandem type include 8) hole transport layer / light emitting layer / electron transport layer / charge generation layer / hole transport layer / light emitting layer / electron transport layer, 9) hole injection layer / hole transport.
  • Charge generation as an intermediate layer between the anode and cathode such as layer / light emitting layer / electron transport layer / electron injection layer / charge generation layer / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer
  • a laminated structure including layers can be mentioned.
  • each of the above layers may be either a single layer or a plurality of layers, and may be doped.
  • the organic thin film light emitting device may include a layer using a capping material that improves the light emitting efficiency due to the optical interference effect.
  • the compound represented by the general formula (1) may be used in any of the above layers in the light emitting device, but is particularly preferably used in the electron transport layer, the charge generation layer or the electron injection layer.
  • the organic thin film light emitting element of the present invention has at least an electron transport layer between the anode and the cathode, and the electron transport layer contains a compound represented by the general formula (1), between the anode and the cathode. It has at least a charge generation layer and a light emitting layer, and the charge generation layer contains a compound represented by the general formula (1), and at least an electron injection layer and a light emitting layer are provided between the anode and the cathode.
  • the electron injection layer contains the compound represented by the general formula (1).
  • the anode and the cathode have a role of supplying a sufficient current for light emission of the device, and at least one of them is transparent or semi-transparent in order to extract light. It is desirable to be transparent.
  • the anode formed on the substrate is a transparent electrode.
  • the substrate In order to maintain the mechanical strength of the light emitting element, it is preferable to form the light emitting element on the substrate.
  • the substrate include glass substrates such as soda glass and non-alkali glass, and plastic substrates.
  • the thickness of the glass substrate may be sufficient to maintain the mechanical strength, and 0.5 mm or more is sufficient.
  • the material of the glass it is preferable that the amount of eluted ions from the glass is small, and non-alkali glass is preferable.
  • soda lime glass coated with a barrier coat such as SiO 2 is also commercially available, and this can also be used.
  • the material used for the anode preferably allows holes to be efficiently injected into the organic layer. In addition, it is preferably transparent or translucent in order to extract light.
  • Materials used for the anode include, for example, conductive metal oxides such as zinc oxide, tin oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO), metals such as gold, silver, and chromium, and iodine. Examples thereof include inorganic conductive substances such as copper oxide and copper sulfide, and conductive polymers such as polythiophene, polypyrrole, and polyaniline. Among these, ITO glass and Nesa glass are preferable.
  • the resistance of the transparent electrode may be such that a sufficient current can be supplied to emit light from the element, but it is preferably low resistance from the viewpoint of power consumption of the element.
  • an ITO substrate of 300 ⁇ / ⁇ or less functions as an element electrode, but since it is now possible to supply a substrate of about 10 ⁇ / ⁇ , a low resistance substrate of 20 ⁇ / ⁇ or less is used. Is preferable.
  • the thickness of ITO can be arbitrarily selected according to the resistance value, and is usually used in the range of 45 to 300 nm.
  • the material used for the cathode is not particularly limited as long as it is a substance capable of efficiently injecting electrons into the light emitting layer.
  • Materials used for the cathode include, for example, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or these metals and low work function metals such as lithium, sodium, potassium, calcium, and magnesium. Examples include alloys and multi-layer lamination. Among them, aluminum, silver, and magnesium are preferable as the main components from the viewpoints of electrical resistance value, ease of film formation, film stability, luminous efficiency, etc., and electron injection into the electron transport layer and the electron injection layer is easy. Therefore, it is more preferable to be composed of magnesium and silver.
  • a protective layer (Protective layer) To protect the cathode, it is preferable to laminate a protective layer (cap layer) on the cathode.
  • the material constituting the protective layer is not particularly limited, but for example, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, alloys using these metals, silica, titania, silicon nitride and the like. Examples thereof include inorganic substances, polyvinyl alcohol, polyvinyl chloride, and organic polymer compounds such as hydrocarbon-based polymer compounds. Further, the compound represented by the general formula (1) can also be used as a protective layer. However, when the light emitting device has an element structure (top emission structure) that extracts light from the cathode side, the material used for the protective layer preferably has light transmission in the visible light region.
  • the hole injection layer is a layer inserted between the anode and the hole transport layer.
  • the hole injection layer may be one layer or a plurality of layers may be laminated.
  • the presence of the hole injection layer between the hole transport layer and the anode is preferable because it is driven at a lower voltage and not only the durability life is improved, but also the carrier balance of the device is improved and the luminous efficiency is also improved.
  • the material used for the hole injection layer is not particularly limited, but for example, 4,4'-bis (N- (3-methylphenyl) -N-phenylamino) biphenyl (TPD), 4,4'-bis (N). -(1-naphthyl) -N-phenylamino) biphenyl (NPD), 4,4'-bis (N, N-bis (4-biphenylyl) amino) biphenyl (TBDB), bis (N, N'-diphenyl- Benzidine derivatives such as 4-aminophenyl) -N, N-diphenyl-4,4'-diamino-1,1'-biphenyl (TPD232), 4,4', 4 "-tris (3-methylphenyl (phenyl)) Triaryl, a group of materials called starburst arylamines such as amino) triphenylamine (m-MTDATA), 4,4', 4 "-tris (1-naphthyl
  • Amine derivatives biscarbazole derivatives such as bis (N-arylcarbazole), bis (N-alkylcarbazole), pyrazoline derivatives, stilben compounds, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin Examples thereof include heterocyclic compounds such as derivatives, polycarbonate and styrene derivatives having the monomer on the side chain, and polymer-based materials such as polythiophene, polyaniline, polyfluorene, polyvinylcarbazole, and polysilane. From the viewpoint of smoothly injecting and transporting holes from the anode to the hole transport layer, a benzidine derivative and a starburst arylamine-based material group are more preferably used.
  • the acceptor compound is a material that forms a contacting hole transport layer when used as a monolayer film, a material that constitutes a hole injection layer when used by doping, and a material that forms a charge transfer complex. When such a material is used, the conductivity of the hole injection layer is improved, the driving voltage of the device is further reduced, and the luminous efficiency and the durable life can be further improved.
  • the accepting compound examples include metal chlorides such as iron (III) chloride, aluminum chloride, gallium chloride, indium chloride and antimony chloride, metal oxides such as molybdenum oxide, vanadium oxide, tungsten oxide and ruthenium oxide, and tris (tris ( 4-Bromophenyl) Aminium Hexachloroantimonate (TBPAH) and other charge transfer complexes, organic compounds having a nitro group, cyano group, halogen or trifluoromethyl group in the molecule, quinone compounds, acid anhydride compounds, fullerene And so on.
  • metal chlorides such as iron (III) chloride, aluminum chloride, gallium chloride, indium chloride and antimony chloride
  • metal oxides such as molybdenum oxide, vanadium oxide, tungsten oxide and ruthenium oxide
  • the hole injection layer may be a single layer regardless of whether the hole injection layer is composed of the acceptor compound alone or the hole injection layer is doped with the acceptor compound.
  • a plurality of layers may be laminated and configured.
  • the hole transport layer is a layer that transports holes injected from the anode to the light emitting layer.
  • the hole transport layer may be one layer or may be formed by laminating a plurality of layers.
  • Examples of the material used for the hole transport layer include those exemplified as the material used for the hole injection layer. From the viewpoint of smoothly injecting and transporting holes into the light emitting layer, triarylamine derivatives and benzidine derivatives are more preferable.
  • the light emitting layer may be either a single layer or a plurality of layers, and each is formed of a light emitting material (host material, dopant material), which may be a mixture of the host material and the dopant material or the host material alone. It may be a mixture of two kinds of host materials and one kind of dopant material. That is, in the light emitting device according to the embodiment of the present invention, only the host material or the dopant material may emit light in each light emitting layer, or both the host material and the dopant material may emit light. From the viewpoint of efficiently utilizing electric energy and obtaining light emission with high color purity, the light emitting layer is preferably composed of a mixture of a host material and a dopant material.
  • the host material and the dopant material may be either one type or a plurality of combinations.
  • the dopant material may be contained entirely or partially in the host material.
  • the dopant material may be laminated or dispersed.
  • the emission color of the dopant material can be controlled.
  • the amount of the dopant material is preferably 30% by weight or less, more preferably 20% by weight or less, based on the host material, from the viewpoint of suppressing the concentration quenching phenomenon.
  • the doping method can be formed by a co-evaporation method with the host material, but it may be mixed with the host material in advance and then vapor-deposited at the same time.
  • the luminescent material examples include fused ring derivatives such as anthracene and pyrene known as luminescent materials, metal chelating oxynoid compounds such as tris (8-quinolinolate) aluminum, and bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives.
  • Tetraphenylbutadiene derivative Tetraphenylbutadiene derivative, inden derivative, coumarin derivative, oxadiazole derivative, pyrolopyridine derivative, perinone derivative, cyclopentadiene derivative, oxadiazole derivative, thiadiazolopyridine derivative, dibenzofuran derivative, carbazole derivative, indolocarbazole derivative, Examples thereof include polymers such as polyphenylene vinylene derivatives, polyparaphenylene derivatives, and polythiophene derivatives.
  • the host material contained in the luminescent material is not limited to only one kind of compound, and a plurality of compounds may be mixed and used, or one or more kinds of other host materials may be mixed and used. Further, they may be laminated and used.
  • the host material is not particularly limited, but is a compound having a fused aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluorene, fluorene, and inden, and a derivative thereof, N, N'-dinaphthyl-.
  • Aromatic amine derivatives such as N, N'-diphenyl-4,4'-diphenyl-1,1'-diamine, metal chelating oxynoid compounds such as tris (8-quinolinate) aluminum (III), distyrylbenzene derivatives, etc.
  • the hosts used when the light emitting layer emits triple term light include metal chelated oxinoid compounds, dibenzofuran derivatives, dibenzothiophene derivatives, carbazole derivatives, indolocarbazole derivatives, triazine derivatives, and triphenylene derivatives. Is preferably used.
  • Examples of the dopant material contained in the luminescent material include compounds having an aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, fluorantene, triphenylene, perylene, fluorene, and inden, and derivatives thereof (for example, 2- (benzothiazole-2-)).
  • aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, fluorantene, triphenylene, perylene, fluorene, and inden, and derivatives thereof (for example, 2- (benzothiazole-2-)).
  • -9,10-diphenylanthracene, 5,6,11,12-tetraphenylnaphthacene, etc. furan, pyrrol, thiophene, silol, 9-cilafluorene, 9,9'-spirobisilafluorene, benzothioph
  • Examples thereof include aromatic amine derivatives such as methylphenyl) -4,4'-diphenyl-1,1'-diamine.
  • aromatic amine derivatives such as methylphenyl) -4,4'-diphenyl-1,1'-diamine.
  • a dopant containing a diamine skeleton and a dopant containing a fluoranthene skeleton are preferable, and the luminous efficiency can be further improved.
  • the dopants used when the light emitting layer emits triplet (phosphorescent emission) include iridium (Ir), ruthenium (Ru), palladium (Pd), platinum (Pt), osmium (Os), and renium.
  • a metal complex compound containing at least one metal selected from the group consisting of (Re) is preferable.
  • the ligand preferably has a nitrogen-containing aromatic heterocycle such as a phenylpyridine skeleton, a phenylquinoline skeleton or a carbene skeleton.
  • the complex is not limited to these, and an appropriate complex is selected based on the required emission color, device performance, and relationship with the host compound.
  • Tris (2-phenylpyridyl) iridium complex Tris ⁇ 2- (2-thiophenyl) pyridyl ⁇ iridium complex, Tris ⁇ 2- (2-benzothiophenyl) pyridyl ⁇ iridium complex, Tris (2-phenyl) Benzothiazole) iridium complex, tris (2-phenylbenzoxazole) iridium complex, trisbenzoquinolin iridium complex, bis (2-phenylpyridyl) (acetylacetonate) iridium complex, bis ⁇ 2- (2-thiophenyl) pyridyl ⁇ iridium Complex, bis ⁇ 2- (2-benzothiophenyl) pyridyl ⁇ (acetylacetonate) iridium complex, bis (2-phenylbenzothiazole) (acetylacetonate) iridium complex, bis (2-phenylbenzoxazole
  • the triplet light emitting material used as the dopant material only one kind may be contained in the light emitting layer, or two or more kinds may be mixed and used.
  • the total weight of the dopant material is preferably 30% by weight or less, more preferably 20% by weight or less, based on the host material.
  • the preferred host and dopant in the triplet light emitting system are not particularly limited, but specific examples include the following.
  • the light emitting layer of the light emitting device according to the embodiment of the present invention contains a triplet light emitting material.
  • the light emitting layer contains a thermally activated delayed fluorescent material.
  • Thermally activated delayed fluorescence is explained on pages 87-103 of "State-of-the-art Organic EL" (edited by Chihaya Adachi and Hiroshi Fujimoto, published by CMC Publishing). In that document, by bringing the energy levels of the excited singlet and excited triplet states of a fluorescent material close together, the reverse energy transfer from the excited triplet state, which normally has a low transition probability, to the excited singlet state is high. It is explained that it occurs with efficiency and that Thermally Activated Fluorescence (TADF) is expressed. Further, FIG. 5 in the document describes the mechanism of delayed fluorescence generation. The emission of delayed fluorescence can be confirmed by transient PL (Photoluminescence) measurement.
  • Thermally activated delayed fluorescent material is also commonly referred to as TADF material.
  • the thermally activated delayed fluorescent material may be a single material exhibiting thermal activated delayed fluorescence, or a plurality of materials exhibiting thermal activated delayed fluorescence. When a plurality of materials are used, they may be used as a mixture, or layers made of each material may be laminated and used.
  • As the thermal activated delayed fluorescent material a known material can be used. Examples thereof include, but are not limited to, benzonitrile derivatives, triazine derivatives, disulfoxide derivatives, carbazole derivatives, indolocarbazole derivatives, dihydrophenazine derivatives, thiazole derivatives, oxaziazole derivatives and the like.
  • the element in which the TADF material is contained in the light emitting layer further contains a fluorescent dopant in the light emitting layer. This is because the TADF material converts triplet excitons into singlet excitons, and the fluorescent dopant receives the singlet excitons, so that higher luminous efficiency and longer device life can be achieved.
  • the electron transport layer is a layer in which electrons are injected from the cathode and further electrons are transported. It is desired that the electron transport layer has high electron injection efficiency and efficiently transports the injected electrons. Therefore, it is preferable that the material constituting the electron transport layer is a substance having a large electron affinity, a high electron mobility, excellent stability, and less likely to generate impurities that become traps during production and use. In particular, in the case of laminating with a thick film thickness, a compound having a molecular weight of 400 or more is preferable because a compound having a low molecular weight tends to be crystallized and the film quality is easily deteriorated.
  • the electron transport layer in the present invention includes a hole blocking layer capable of efficiently blocking the movement of holes as a synonym, and the hole blocking layer and the electron transport layer are laminated with a plurality of materials even if they are used alone. It may be configured.
  • Examples of the electron transporting material used for the electron transporting layer include condensed polycyclic aromatic derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis (diphenylethenyl) biphenyl, anthraquinone and diphenoquinone.
  • Kinon derivatives, phosphoroxide derivatives, quinolinol complexes such as tris (8-quinolinolate) aluminum (III), benzoquinolinol complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes and various metal complexes such as flavonol metal complexes can be mentioned.
  • a heteroaryl ring structure composed of elements selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus, and containing electron-accepting nitrogen, because the drive voltage can be further reduced and more efficient light emission can be obtained. It is preferable to use the compound having.
  • the electron-accepting nitrogen referred to here represents a nitrogen atom forming a multiple bond with an adjacent atom. Since the nitrogen atom has a high electronegativity, the multiple bond has an electron-accepting property. Therefore, aromatic heterocycles containing electron-accepting nitrogen have high electron affinity.
  • An electron transporting material having electron-accepting nitrogen makes it easier to receive electrons from a cathode having a high electron affinity, and can be driven at a lower voltage. In addition, the supply of electrons to the light emitting layer is increased, and the recombination probability is increased, so that the luminous efficiency is further improved.
  • heteroaryl ring containing electron-accepting nitrogen examples include a triazine ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a quinoline ring, a quinoxaline ring, a quinazoline ring, a naphthylidine ring, a pyrimidopyrimidine ring, a benzoquinoline ring, and a phenanthroline ring.
  • Examples thereof include an imidazole ring, an oxazole ring, an oxadiazole ring, a triazole ring, a thiazole ring, a thiaziazole ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, and a phenanthleiumidazole ring.
  • Examples of compounds having these heteroaryl ring structures include pyridine derivatives, triazine derivatives, quinazoline derivatives, pyrimidine derivatives, benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazol derivatives, triazole derivatives, and pyrazines.
  • Examples thereof include derivatives, phenanthroline derivatives, quinoxalin derivatives, quinoline derivatives, benzoquinolin derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives and naphthylidine derivatives.
  • imidazole derivatives such as tris (N-phenylbenzimidazole-2-yl) benzene, and oxadiazole derivatives such as 1,3-bis [(4-tert-butylphenyl) 1,3,4-oxadiazolyl] phenylene
  • Triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole
  • phenanthroline derivatives such as vasocproin and 1,3-bis (1,10-phenanthroline-9-yl) benzene
  • 2,2' -Bis (benzo [h] quinoline-2-yl) -9,9'-benzoquinoline derivatives such as spirobifluorene, 2,5-bis (6'-(2', 2 "-bipyridyl))-1
  • Bipyridine derivatives such as 1-dimethyl-3,4-diphenylsilol
  • terpyridine derivatives such as 1,
  • the condensed polycyclic aromatic skeleton may be a fluoranthene skeleton, an anthracene skeleton, pyrene skeleton or phenanthroline skeleton. More preferred.
  • the preferred electron transport material is not particularly limited, but specific examples include the following.
  • the compound represented by the general formula (1) is also preferable because it has high electron transportability and exhibits excellent properties as an electron transport material.
  • the electron-transporting material may be used alone, two or more of the electron-transporting materials may be mixed, or one or more of the other electron-transporting materials may be mixed with the electron-transporting material. It doesn't matter. It may also contain a donor compound.
  • the donor compound is a compound that facilitates electron injection from the cathode or the electron injection layer into the electron transport layer by improving the electron injection barrier, and further improves the electrical conductivity of the electron transport layer.
  • Preferred examples of donor compounds include alkali metals, inorganic salts containing alkali metals, complexes of alkali metals and organic substances, alkaline earth metals, inorganic salts containing alkaline earth metals or alkaline earth metals and organic substances. And the like.
  • Preferred types of alkali metals and alkaline earth metals include alkali metals such as lithium, sodium, potassium, rubidium and cesium, which have a low work function and a large effect of improving electron transport ability, and alkalis such as magnesium, calcium, cerium and barium. Examples include earth metals.
  • the metal is in a complex state with an inorganic salt or an organic substance rather than a simple substance. Further, it is more preferable that it is in a complex state with an organic substance in that it can be easily handled in the atmosphere and the addition concentration can be easily adjusted.
  • inorganic salts LiO, Li oxide such as 2 O, nitrides, LiF, NaF, fluorides KF, etc., Li 2 CO 3, Na 2 CO 3, K 2 CO 3, Rb 2 CO 3, Examples thereof include carbonates such as Cs 2 CO 3 and the like.
  • preferred examples of the alkali metal or alkaline earth metal include lithium and cesium from the viewpoint that the driving voltage can be further reduced.
  • organic substance in the complex with the organic substance include quinolinol, benzoquinolinol, pyridylphenol, flavonol, hydroxyimidazolipyridine, hydroxybenzazole, hydroxytriazole and the like.
  • a complex of an alkali metal and an organic substance is preferable from the viewpoint of being large enough to further reduce the driving voltage of the light emitting element.
  • a complex of lithium and an organic substance is more preferable, and lithium quinolinol (Liq), which can be obtained at a relatively low cost, is particularly preferable.
  • the ionization potential of the electron transport layer is not particularly limited, but is preferably 5.6 eV or more and 8.0 eV or less, and more preferably 5.6 eV or more and 7.0 eV or less.
  • the method for forming each of the above layers constituting the light emitting device is not particularly limited, such as resistance heating vapor deposition, electron beam deposition, sputtering, molecular lamination method, and coating method, but resistance heating vapor deposition or electron beam deposition is usually performed from the viewpoint of element characteristics. preferable.
  • an electron injection layer may be provided between the cathode and the electron transport layer.
  • the electron injection layer is inserted for the purpose of assisting the injection of electrons from the cathode to the electron transport layer, but when inserting, a compound having a heteroaryl ring structure containing electron-accepting nitrogen may be used.
  • the above donor material may be used.
  • an insulator or a semiconductor inorganic substance can be used for the electron injection layer. It is preferable to use these materials because it is possible to suppress a short circuit of the light emitting element and improve the electron injection property.
  • At least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides.
  • preferred alkali metal chalcogenides include, for example, Li 2 O, Na 2 S and Na 2 Se.
  • preferred alkaline earth metal chalcogenides include, for example, CaO, BaO, SrO, BeO, BaS and CaSe.
  • preferred alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, NaCl and the like.
  • preferred alkali earth metal halides include, for example, fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluoride.
  • a complex of an organic substance and a metal is also preferably used.
  • a complex of an organic substance and a metal is used for the electron injection layer, it is preferable because the film thickness can be easily adjusted.
  • Preferred examples of the organic substance in such an organometallic complex include quinolinol, benzoquinolinol, pyridylphenol, flavonol, hydroxyimidazolipyridine, hydroxybenzazole, hydroxytriazole and the like.
  • the compound represented by the general formula (1) is also preferable because it has high electron injection properties and exhibits excellent properties as a material for the electron injection layer.
  • the charge generation layer in the present invention is generally composed of a bilayer, and can be specifically used as a pn junction charge generation layer composed of an n-type charge generation layer and a p-type charge generation layer.
  • the pn junction type charge generation layer generates a charge or separates the charge into holes and electrons by applying a voltage in the light emitting element, and separates these holes and electrons into a hole transport layer and an electron. It is injected into the light emitting layer via the transport layer.
  • a light emitting element in which light emitting layers are laminated it functions as a charge generation layer of an intermediate layer.
  • the n-type charge generation layer supplies electrons to the first light emitting layer existing on the anode side, and the p-type charge generation layer supplies holes to the second light emitting layer existing on the cathode side. Therefore, the luminous efficiency of the light emitting element in which a plurality of light emitting layers are laminated can be further improved, the driving voltage can be lowered, and the durable life of the element can be further improved.
  • the n-type charge generation layer is composed of an n-type dopant and a host, and conventional materials can be used for these.
  • an alkali metal, an alkaline earth metal, or a rare earth metal can be used as the n-type dopant.
  • a triazine derivative, a phenanthroline derivative and an oligopyridine derivative can be used as a host.
  • the compound represented by the general formula (1) and the phenanthroline derivative are preferable because they exhibit excellent properties as a host of the n-type charge generation layer.
  • the phenanthroline derivative is used as the host of the n-type charge generation layer, it is preferable to use the compound represented by the general formula (1) as the electron transport material. This is because the electron injection barrier between these materials is small, so that the drive voltage in the device can be further reduced.
  • the p-type charge generation layer is composed of a p-type dopant and a host, and conventional materials can be used for these.
  • p-type dopants tetrafluorole-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), tetracyanoquinodimethane derivative, radialene derivative, iodine, FeCl 3 , FeF 3 , SbCl 5 Etc. can be used.
  • the p-type dopant is preferably a radialene derivative.
  • Arylamine derivatives are preferred as hosts.
  • the thickness of the organic layer cannot be limited because it depends on the resistance value of the luminescent substance, but it is preferably 1 to 1000 nm.
  • the film thicknesses of the light emitting layer, the electron transport layer, and the hole transport layer are preferably 1 nm or more and 200 nm or less, and more preferably 5 nm or more and 100 nm or less.
  • the light emitting element according to the embodiment of the present invention has a function of converting electric energy into light.
  • direct current is mainly used as electrical energy, but pulse current and alternating current can also be used.
  • the current value and the voltage value are not particularly limited, but in consideration of the power consumption and the life of the element, it is preferable that the current value and the voltage value are selected so as to obtain the maximum brightness with the lowest possible energy.
  • the light emitting element according to the embodiment of the present invention is suitably used as a display device such as a display that displays in a matrix and / or segment system, for example.
  • the light emitting element according to the embodiment of the present invention is also preferably used as a backlight for various devices and the like.
  • the backlight is mainly used for the purpose of improving the visibility of a display device such as a display that does not emit light by itself, and is used for a liquid crystal display, a clock, an audio device, an automobile panel, a display board, a sign, and the like.
  • the light emitting element of the present invention is preferably used for a liquid crystal display, particularly a backlight for a personal computer whose thinness is being studied, and can provide a backlight thinner and lighter than the conventional one.
  • the light emitting element according to the embodiment of the present invention is also preferably used as various lighting devices.
  • the light emitting element according to the embodiment of the present invention can achieve both high luminous efficiency and high color purity, and can be made thinner and lighter, so that low power consumption and bright emission color can be achieved.
  • a lighting device with high design can be realized.
  • the obtained compound 1 was sublimated and purified at about 340 ° C. under a pressure of 1 ⁇ 10 -3 Pa using an oil diffusion pump, and then used in Examples.
  • the HPLC purity (area% at the measurement wavelength of 254 nm) of Compound 1 before and after sublimation purification was 99.9%.
  • the obtained compound 2 was sublimated and purified at about 340 ° C. under a pressure of 1 ⁇ 10 -3 Pa using an oil diffusion pump, and then used in Examples.
  • the HPLC purity (area% at the measurement wavelength of 254 nm) of Compound 2 before and after sublimation purification was 99.9%.
  • the light emitting elements obtained in Examples 12 to 22 and Comparative Examples 15 to 28 were lit at a brightness of 1000 cd / m 2 , and the initial drive voltage was measured. Further, the voltage when the constant current was driven for 100 hours at a current density of 10 mA / cm 2 at room temperature was measured, and the amount of voltage increase from the initial drive voltage was calculated.
  • Examples 23 to 44 and Comparative Examples 29 to 56 were each driven with a current density of 10 mA / cm 2 , and the initial drive voltage was measured.
  • Example 12 to 22 and Comparative Examples 15 to 28 were lit at a current density of 10 mA / cm 2 , respectively, and the external quantum efficiency was measured to evaluate the luminous efficiency. It can be evaluated that the higher the external quantum efficiency, the better the luminous efficiency.
  • Luminance The light emitting elements obtained in Examples 23 to 44 and Comparative Examples 29 to 56 were lit at 10 mA / cm 2 , the brightness was measured, and the luminous efficiency was evaluated. It can be evaluated that the higher the brightness, the better the luminous efficiency.
  • Example 1 A glass substrate (manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product) having an ITO transparent conductive film deposited at 125 nm as an anode was cut into 38 mm ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with "Semicoclean" (registered trademark) 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, and then washed with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before the device was manufactured, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 -4 Pa or less.
  • "Semicoclean" registered trademark
  • UV-ozone treatment for 1 hour immediately before the device was manufactured, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 -4 Pa or less.
  • Layer 1 was formed.
  • aluminum was vapor-deposited at 60 nm to serve as a cathode, and a 5 mm ⁇ 5 mm square element was manufactured.
  • the film thickness referred to here is a crystal oscillation type film thickness monitor display value, and is common to other examples and comparative examples.
  • the initial drive voltage was 0.030 V
  • the amount of voltage increase when driven at 70 ° C. for 100 hours was 0.001 V.
  • Example 2 to 11 Comparative Examples 1 to 14
  • the device was manufactured in the same manner as in Example 1 except that the compound to be used and the vapor deposition rate ratio of the compound to the metal element were changed as shown in Table 1.
  • the results of each example and comparative example are shown in Table 1.
  • Compounds 2 to 23 are the compounds shown below.
  • Example 12 A glass substrate (manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which an ITO transparent conductive film was deposited as an anode at 165 nm was cut into 38 mm ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with "Semicoclean" 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, and then washed with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before the device was manufactured, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 -4 Pa or less.
  • "Semicoclean" 56 trade name, manufactured by Furuuchi Chemical Co., Ltd.
  • HAT-CN 6 was first vapor-deposited at 5 nm as a hole injection layer, and then HT-1 was vapor-deposited at 50 nm as a hole transport layer.
  • a mixed layer of the host material H-1 and the dopant material D-1 was vapor-deposited to a thickness of 20 nm so that the doping concentration was 5% by weight.
  • aluminum was vapor-deposited at 60 nm to serve as a cathode, and a 5 mm ⁇ 5 mm square light emitting device was manufactured.
  • Example 13 to 22 Comparative Examples 15 to 28 A light emitting device was produced in the same manner as in Example 12 except that the compound used and the vapor deposition rate ratio of the compound to the metal element were changed as shown in Table 2. The results of each example and comparative example are shown in Table 2.
  • Example 23 A glass substrate (manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which an ITO transparent conductive film was deposited as an anode at 165 nm was cut into 38 mm ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with "Semicoclean" 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, and then washed with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before the device was manufactured, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 -4 Pa or less.
  • "Semicoclean" 56 trade name, manufactured by Furuuchi Chemical Co., Ltd.
  • HAT-CN 6 was first vapor-deposited at 5 nm as a hole injection layer.
  • a light emitting unit (first light emitting unit) composed of a hole transport layer, a light emitting layer and an electron transport layer was formed on the hole injection layer.
  • HT-1 is vapor-deposited at 50 nm as a hole transport layer, and then a mixed layer of host material H-1 and dopant material D-1 is used as a light emitting layer to have a doping concentration of 5% by weight.
  • HAT-CN 6 was vapor-deposited at 10 nm as a P-type charge generation layer.
  • the initial drive voltage was 8.22 V
  • the brightness was 1820 cd / m 2
  • the durable life was 2500 hours.
  • Examples 24-33, Comparative Examples 29-42 A light emitting device was produced in the same manner as in Example 23, except that the compound used and the vapor deposition rate ratio of the compound to the metal element were changed as shown in Table 3. The results of each example and comparative example are shown in Table 3.
  • Example 34 Compound 1 obtained in Synthesis Example 1 was used in place of ET-1 in the formation of the electron transport layer, and ET-2 was used in place of compound 1 in the formation of the N-type charge generation layer.
  • a light emitting element was produced in the same manner as in Example 23 except for the above.
  • ET-2 is a compound shown below.
  • Examples 35 to 44, Comparative Examples 43 to 56 A light emitting device was produced in the same manner as in Example 34, except that the compound used and the vapor deposition rate ratio of the compound to the metal element were changed as shown in Table 4. The results of each example and comparative example are shown in Table 4.

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Abstract

L'objet de la présente invention est de fournir un composé représenté par la formule générale (1), au moyen duquel il est possible d'obtenir un élément électroluminescent à couche mince organique ayant une durée de vie et une efficacité d'émission de lumière supérieures. (Dans la formule générale (1), l'un quelconque de X1 à X3 est un atome d'azote et les autres sont des groupes méthine. L1 représente un groupe biphénylène substitué ou non substitué, un groupe terphénylène, un groupe naphtylène, un groupe quaterphénylène, un groupe diméthylfluorènylène, un groupe diphénylfluorénylène ou un groupe spirobifluorenylène. Cependant, lorsque ces groupes sont substitués, le substituant est un groupe alkyle ou un groupe alcoxy. "A" représente un groupe phénanthrényle, un groupe pyrényle, un groupe diméthylfluorényle, un groupe diphénylfluorényle ou un groupe spirobifluorényle.)
PCT/JP2020/040397 2020-01-30 2020-10-28 Composé, élément électroluminescent à couche mince organique, dispositif d'affichage, et dispositif d'éclairage WO2021152940A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024018915A1 (fr) * 2022-07-20 2024-01-25 東レ株式会社 Composé, élément électroluminescent, dispositif d'affichage et dispositif d'éclairage

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018041123A1 (fr) * 2016-08-31 2018-03-08 江苏三月光电科技有限公司 Composé ayant un noyau de fluorène et un hétérocycle contenant de l'azote à six chaînons et son application dans un dispositif électroluminescent organique
KR20190053563A (ko) * 2017-11-10 2019-05-20 주식회사 진웅산업 벤조플루오란텐계 화합물 및 이를 포함하는 유기발광소자
JP2019513133A (ja) * 2016-03-17 2019-05-23 メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ スピロビフルオレン構造を有する化合物
JP2020502088A (ja) * 2017-02-21 2020-01-23 エルジー・ケム・リミテッド 新規なヘテロ環式化合物およびこれを利用した有機発光素子
JP2020123477A (ja) * 2019-01-30 2020-08-13 東レ株式会社 発光素子、表示装置および照明装置

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012173073A1 (fr) 2011-06-15 2012-12-20 東レ株式会社 Matière d'élément électroluminescent et élément électroluminescent
CN106458899A (zh) * 2014-05-28 2017-02-22 东丽株式会社 荧蒽衍生物、含有其的电子设备、发光元件及光电转换元件
KR20160044959A (ko) 2014-10-16 2016-04-26 삼성에스디에스 주식회사 Ｗａｖｅ 기반의 안테나 제어 장치 및 제어방법
CN107848989B (zh) 2016-07-20 2021-06-11 株式会社Lg化学 新杂环化合物和包含其的有机发光器件
KR102443233B1 (ko) * 2017-09-22 2022-09-15 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019513133A (ja) * 2016-03-17 2019-05-23 メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ スピロビフルオレン構造を有する化合物
WO2018041123A1 (fr) * 2016-08-31 2018-03-08 江苏三月光电科技有限公司 Composé ayant un noyau de fluorène et un hétérocycle contenant de l'azote à six chaînons et son application dans un dispositif électroluminescent organique
JP2020502088A (ja) * 2017-02-21 2020-01-23 エルジー・ケム・リミテッド 新規なヘテロ環式化合物およびこれを利用した有機発光素子
KR20190053563A (ko) * 2017-11-10 2019-05-20 주식회사 진웅산업 벤조플루오란텐계 화합물 및 이를 포함하는 유기발광소자
JP2020123477A (ja) * 2019-01-30 2020-08-13 東レ株式会社 発光素子、表示装置および照明装置

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024018915A1 (fr) * 2022-07-20 2024-01-25 東レ株式会社 Composé, élément électroluminescent, dispositif d'affichage et dispositif d'éclairage

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