WO2022259859A1 - Phénoxazines, et élément électroluminescent organique, dispositif d'affichage, dispositif d'imagerie, équipement électronique, dispositif d'éclairage et objet mobile les comprenant - Google Patents

Phénoxazines, et élément électroluminescent organique, dispositif d'affichage, dispositif d'imagerie, équipement électronique, dispositif d'éclairage et objet mobile les comprenant Download PDF

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WO2022259859A1
WO2022259859A1 PCT/JP2022/021210 JP2022021210W WO2022259859A1 WO 2022259859 A1 WO2022259859 A1 WO 2022259859A1 JP 2022021210 W JP2022021210 W JP 2022021210W WO 2022259859 A1 WO2022259859 A1 WO 2022259859A1
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light
group
organic light
layer
emitting
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Japanese (ja)
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武史 關口
祐斗 伊藤
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キヤノン株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H05B33/02—Details
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to phenoxazines with specific structures that are useful as light-emitting materials, and organic light-emitting devices, display devices, imaging devices, electronic devices, lighting devices, and moving bodies each having the same.
  • An organic electroluminescence device is an electronic device having a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. By injecting electrons and holes from the pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and the organic light-emitting device emits light when the excitons return to the ground state. . It is known that fluorescence is emitted when the energy of the singlet of the organic compound emits light, and phosphorescence is emitted when the energy of the triplet of the organic compound emits light. It is known that the emission efficiency of phosphorescence tends to be higher than that of fluorescence because the energy generated in triplet excitation energy is larger than the energy generated in singlet excitation energy.
  • thermally excited delayed fluorescence materials are known in which the energy generated in triplet crosses the energy of singlet inversely with the energy of room temperature. This material exhibits the same efficiency as phosphorescence while having the characteristics of fluorescence.
  • the development of light-emitting organic compounds with even higher performance is required, and various organic materials are being actively developed.
  • Patent Document 1 describes an organic compound having a triazine.
  • the following compound A and an organic light-emitting device having the compound A are described as a light-emitting material having a phenoxazine structure, and emit green light. is stated.
  • Patent Document 3 describes an organic compound having a phenoxazine structure and a carbazole structure, and describes an organic light emitting device using the organic compound as a material for an electron blocking layer by providing an arylamine in the carbazole structure. ing.
  • phenoxazine compounds As described above, various phenoxazine compounds have been developed for use in organic EL devices. However, these are phenoxazine compounds having an electron-withdrawing group, and are not materials that emit blue light.
  • the organic compounds described in Patent Documents 1 and 2 are green light-emitting materials, and organic compounds that have a phenoxazine skeleton and emit blue light have not been known.
  • the present invention has been made in view of the above problems, and an object thereof is to provide a blue light-emitting material having a phenoxazine skeleton.
  • the present invention provides an organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer comprises the following general An organic light-emitting device comprising an organic compound represented by formula (1).
  • A has a lowest unoccupied molecular orbital (LUMO) of ⁇ 1.79 eV or more and ⁇ 0.77 eV or less, and an electron donating group containing a biphenyl group, a terphenyl group, a quaterphenyl group or a carbazole structure and does not contain an electron-withdrawing group.
  • LUMO lowest unoccupied molecular orbital
  • A may have an alkyl group, an alkoxy group, an alkylthio group, a substituted amino group, or a cycloalkyl group as a substituent.
  • n represents an integer of 1 or more.
  • R 1 to R 8 each independently represent a hydrogen atom or a substituent.
  • the substituents include a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted amino group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, and a substituted or unsubstituted alkynyl group.
  • it is selected from an unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amido group, and a substituted or unsubstituted silyl group.
  • an organic compound that has a phenoxazine skeleton and emits blue light.
  • FIG. 1 is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the invention
  • FIG. 1 is a schematic cross-sectional view of an example of a display device using an organic light-emitting element according to an embodiment of the invention
  • FIG. 1 is a schematic diagram of an example of a display device using an organic light-emitting device according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of an imaging device according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of a mobile device according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of a display device according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of a foldable display device; FIG. It is a mimetic diagram showing an example of a lighting installation concerning one embodiment of the present invention.
  • 1 is a schematic diagram showing an automobile as an example of a moving body according to an embodiment of the present invention;
  • FIG. 1 is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention;
  • FIG. It is an example of the wearable device which concerns on one Embodiment of this invention, and is a schematic diagram which shows the form which has an imaging device.
  • the organic compound according to the present invention is characterized by having a structure represented by general formula (1).
  • A has a lowest unoccupied molecular orbital (LUMO) of ⁇ 1.79 eV or more and ⁇ 0.77 eV or less, and an electron donating group containing a biphenyl group, a terphenyl group, a quaterphenyl group or a carbazolyl structure and does not contain an electron-withdrawing group.
  • Electron-withdrawing groups include cyano, triazyl, pyrimidyl, triazyl, and fluorine groups.
  • A may have a structure consisting only of a biphenyl group and a carbazolyl group among the above.
  • the biphenyl group and carbazolyl group may have a substituent.
  • the LUMO value of A is an organic compound that can emit good blue light by selecting an appropriate substituent.
  • the LUMO of A may be estimated by molecular orbital calculations. Values calculated by density functional theory (B3LYP/6-31G * ) can be used for molecular orbital calculations.
  • Blue light can be emitted when the LUMO calculation value of A is -1.79 eV or more and -0.77 eV or less.
  • the LUMO of A is more preferably ⁇ 1.25 eV or more and ⁇ 0.77 eV or less.
  • A may have an alkyl group, an alkoxy group, an alkylthio group, a substituted amino group, or a cycloalkyl group as a substituent.
  • n an integer of 1 or more.
  • the nitrogen atoms of multiple phenoxazine structures may be bonded to A.
  • R 1 to R 8 each independently represent a hydrogen atom or a substituent.
  • the substituents include a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted amino group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, and a substituted or unsubstituted alkynyl group.
  • it is selected from an unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amido group, and a substituted or unsubstituted silyl group.
  • the alkyl group may be an alkyl group having 1 to 20 carbon atoms. More preferably, it may be an alkyl group having 1 to 8 carbon atoms or an alkyl group having 1 to 4 carbon atoms.
  • the cycloalkyl group may be a cycloalkyl group having 3 to 8 carbon atoms.
  • the alkoxy group may be an alkoxy group having 1 to 20 carbon atoms. More preferably, it may be an alkoxy group having 1 to 8 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
  • the alkylthio group may be an alkylthio group having 1 to 8 carbon atoms.
  • the substituted amino group may be an amino group having an alkyl group as a substituent, that is, an alkyl-substituted amino group.
  • the alkyl group may have from 1 to 8 carbon atoms.
  • the substituted or unsubstituted alkenyl group may have 2 to 20 carbon atoms, or 2 to 8 carbon atoms.
  • the substituted or unsubstituted alkynyl group may have 3 to 20 carbon atoms, or 3 to 8 carbon atoms.
  • the substituted or unsubstituted alkoxycarbonyl group may have 2 to 20 carbon atoms, or 2 to 8 carbon atoms.
  • the above substituent may further have a substituent, and may have a halogen atom, an alkyl group, or a phenyl group as a substituent.
  • Table 1 shows the calculated values of LUMO.
  • the organic light-emitting device of this embodiment has at least a first electrode, a second electrode, and an organic compound layer arranged between these electrodes.
  • One of the first electrode and the second electrode is an anode and the other is a cathode.
  • the organic compound layer may be a single layer or a multi-layer laminate as long as it has a light-emitting layer.
  • the organic compound layer includes, in addition to the light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole/exciton blocking layer, an electron transport layer, an electron It may have an injection layer or the like.
  • the light-emitting layer may be a single layer, or may be a laminate composed of a plurality of layers.
  • At least one layer of the organic compound layer contains the organometallic complex of the present embodiment.
  • the organic compound according to the present embodiment is included in any of the light-emitting layer, the hole injection layer, the hole transport layer, the electron blocking layer, the hole/exciton blocking layer, the electron transport layer, the electron injection layer, and the like. is The organic compound according to this embodiment is preferably contained in the light-emitting layer.
  • the light-emitting layer when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer composed only of the organic compound according to this embodiment. A layer composed of such an organometallic complex and another compound may also be used.
  • the organic compound according to this embodiment when the light-emitting layer is a layer composed of the organometallic complex according to this embodiment and another compound, the organic compound according to this embodiment may be used as a host of the light-emitting layer, or may be used as a guest. You may It may also be used as an assist material that can be included in the light-emitting layer.
  • the host is a compound having the largest mass ratio among the compounds constituting the light-emitting layer.
  • a guest is a compound having a mass ratio smaller than that of a host among the compounds constituting the light-emitting layer, and is a compound responsible for main light emission.
  • the assist material is a compound that has a lower mass ratio than that of the host among the compounds that constitute the light-emitting layer and that assists the light emission of the guest.
  • the assist material is also called a second host.
  • the host material can also be called the first compound, and the assist material can be called the second compound.
  • the light-emitting layer further has a first organic compound different from the compound according to the present invention, and the first organic compound has the lowest excited singlet energy than the organic compound represented by the general formula (1). may be a configuration with a large value.
  • the concentration of the guest is preferably 0.01% by mass or more and 20% by mass or less with respect to the entire light-emitting layer, and more preferably 0.1% by mass or more and 10% by mass. % or less is more preferable.
  • This light-emitting layer may be a single layer or multiple layers, and by including a light-emitting material having another light-emitting color, it is possible to mix red light emission, which is the light-emitting color of the present embodiment.
  • a multi-layer means a state in which a light-emitting layer and another light-emitting layer are laminated. In this case, the emission color of the organic light-emitting element is not limited to red.
  • the film formation method is vapor deposition or coating film formation. The details of this will be described in detail in the examples that will be described later.
  • the organometallic complex according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material for an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, and the like.
  • the emission color of the organic light-emitting element is not limited to red. More specifically, white light emission may be used, or neutral color light may be used.
  • organic compound according to the present embodiment conventionally known low-molecular-weight and high-molecular-weight hole-injecting compounds or hole-transporting compounds, host compounds, light-emitting compounds, and electron-injecting compounds can be used as necessary.
  • a polarizing compound or an electron-transporting compound or the like can be used together. Examples of these compounds are given below.
  • the hole-injecting and transporting material a material having high hole mobility is preferable so that holes can be easily injected from the anode and the injected holes can be transported to the light-emitting layer.
  • a material having a high glass transition temperature is preferable.
  • Low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and others.
  • a conductive polymer can be mentioned.
  • the above hole injection transport materials are also suitably used for the electron blocking layer. Specific examples of the compound used as the hole-injecting and transporting material are shown below, but are of course not limited to these.
  • HT16 to HT18 can reduce the driving voltage by using them in the layer in contact with the anode.
  • HT16 is widely used in organic light emitting devices.
  • HT2, HT3, HT4, HT5, HT6, HT10, and HT12 may be used for the organic compound layer adjacent to HT16. Further, a plurality of materials may be used for one organic compound layer.
  • Light-emitting materials mainly involved in light-emitting functions include condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, tris(8 -quinolinolato) aluminum complexes, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes; Molecular derivatives are included.
  • condensed ring compounds e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.
  • quinacridone derivatives coumarin derivatives
  • stilbene derivatives tris(
  • the luminescent material is a hydrocarbon compound, it is possible to reduce a decrease in luminous efficiency due to exciplex formation and a decrease in color purity due to a change in the emission spectrum of the luminescent material due to exciplex formation, which is preferable.
  • a hydrocarbon compound is a compound composed only of carbon and hydrogen, and among the above exemplary compounds, BD7, BD8, GD5 to GD9, and RD1.
  • the light-emitting material is a condensed polycyclic ring containing a 5-membered ring, it is preferable because it has a high ionization potential, is difficult to oxidize, and becomes an element with a long service life.
  • the above exemplary compounds are BD7, BD8, GD5 to GD9, and RD1.
  • Examples of the light-emitting layer host or light-emitting assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, organic beryllium complexes, and the like.
  • Hydrocarbon compounds are compounds composed only of carbon and hydrogen, and are EM1 to EM12 and EM16 to EM27 among the above exemplary compounds.
  • the electron-transporting material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole-transporting material.
  • Materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron-transporting materials are also suitably used for the hole blocking layer.
  • the electron-injecting material can be arbitrarily selected from those that allow electrons to be easily injected from the cathode, and is selected in consideration of the balance with the hole-injecting property.
  • Organic compounds also include n-type dopants and reducing dopants. Examples thereof include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives and acridine derivatives.
  • An organic light-emitting device is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate.
  • Protective layers, color filters, microlenses, etc. may be provided over the cathode.
  • a planarization layer may be provided between it and the protective layer.
  • the planarizing layer can be made of acrylic resin or the like. The same applies to the case where a flattening layer is provided between the color filter and the microlens.
  • substrates examples include quartz, glass, silicon wafers, resins, and metals.
  • a switching element such as a transistor and wiring may be provided on the substrate, and an insulating layer may be provided thereon. Any material can be used for the insulating layer as long as a contact hole can be formed between the insulating layer and the first electrode, and insulation from unconnected wiring can be ensured.
  • a resin such as polyimide, silicon oxide, silicon nitride, or the like can be used.
  • a pair of electrodes can be used as the electrodes.
  • the pair of electrodes may be an anode and a cathode.
  • the electrode with the higher potential is the anode, and the other is the cathode.
  • the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.
  • a material with a work function that is as large as possible is good for the constituent material of the anode.
  • simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, mixtures containing these, or alloys combining these, tin oxide, zinc oxide, indium oxide, tin oxide Metal oxides such as indium (ITO) and zinc indium oxide can be used.
  • Conductive polymers such as polyaniline, polypyrrole and polythiophene can also be used.
  • the anode may be composed of a single layer, or may be composed of a plurality of layers.
  • chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used.
  • the above material can also function as a reflective film that does not have a role as an electrode.
  • a transparent conductive layer of an oxide such as indium tin oxide (ITO) or indium zinc oxide can be used, but is not limited to these.
  • ITO indium tin oxide
  • a photolithography technique can be used to form the electrodes.
  • a material with a small work function is preferable as a constituent material for the cathode.
  • alkali metals such as lithium, alkaline earth metals such as calcium, simple metals such as aluminum, titanium, manganese, silver, lead, and chromium, or mixtures thereof may be used.
  • alloys obtained by combining these simple metals can also be used.
  • magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver and the like can be used.
  • Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used singly or in combination of two or more.
  • the cathode may be of a single-layer structure or a multi-layer structure.
  • it is preferable to use silver and in order to reduce aggregation of silver, it is more preferable to use a silver alloy. Any alloy ratio is acceptable as long as aggregation of silver can be reduced.
  • silver:other metal may be 1:1, 3:1, and the like.
  • the cathode may be a top emission element using an oxide conductive layer such as ITO, or may be a bottom emission element using a reflective electrode such as aluminum (Al), and is not particularly limited.
  • the method for forming the cathode is not particularly limited, but it is more preferable to use a direct current or alternating current sputtering method or the like because the film coverage is good and the resistance can be easily lowered.
  • the organic compound layer may be formed of a single layer or multiple layers. When it has multiple layers, it may be called a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on its function.
  • the organic compound layer is mainly composed of organic compounds, but may contain inorganic atoms and inorganic compounds. For example, it may have copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, and the like.
  • the organic compound layer may be arranged between the first electrode and the second electrode, and may be arranged in contact with the first electrode and the second electrode.
  • a protective layer may be provided over the cathode.
  • a protective layer may be provided over the cathode.
  • a passivation film such as silicon nitride may be provided on the cathode to reduce penetration of water or the like into the organic compound layer.
  • a silicon nitride film having a thickness of 2 ⁇ m may be formed by a CVD method as a protective layer.
  • a protective layer may be provided using an atomic deposition method (ALD method) after film formation by the CVD method.
  • the material of the film formed by the ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed by CVD on the film formed by ALD.
  • a film formed by the ALD method may have a smaller film thickness than a film formed by the CVD method. Specifically, it may be 50% or less, further 10% or less.
  • a color filter may be provided on the protective layer.
  • a color filter considering the size of the organic light-emitting element may be provided on another substrate and then bonded to the substrate provided with the organic light-emitting element.
  • a color filter may be patterned.
  • the color filters may be composed of polymers.
  • a planarization layer may be provided between the color filter and the protective layer.
  • the planarization layer is provided for the purpose of reducing unevenness of the underlying layer. Without limiting its purpose, it may also be referred to as a material resin layer.
  • the planarization layer may be composed of an organic compound, and may be a low-molecular or high-molecular compound, preferably a high-molecular compound.
  • the planarization layer may be provided above and below the color filter, and the constituent materials thereof may be the same or different.
  • Specific examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicon resin, urea resin, and the like.
  • the organic light-emitting device may have an optical member such as a microlens on its light exit side.
  • the microlenses may be made of acrylic resin, epoxy resin, or the like.
  • the purpose of the microlens may be to increase the amount of light extracted from the organic light-emitting device and to control the direction of the extracted light.
  • the microlens may have a hemispherical shape. When it has a hemispherical shape, among the tangents that are in contact with the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between the tangent and the hemisphere is the apex of the microlens.
  • the apex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangent lines that are tangent to the semicircle of the microlens in the sectional view, there is a tangent line that is parallel to the insulating layer, and the point of contact between the tangent line and the semicircle is the vertex of the microlens.
  • a line segment from the end point of the arc shape to the end point of another arc shape is assumed, and the midpoint of the line segment can be called the midpoint of the microlens.
  • a cross section that determines the vertex and the midpoint may be a cross section perpendicular to the insulating layer.
  • a counter substrate may be provided over the planarization layer.
  • the counter substrate is called the counter substrate because it is provided at a position corresponding to the substrate described above.
  • the constituent material of the counter substrate may be the same as that of the aforementioned substrate.
  • the opposing substrate may be the second substrate when the substrate described above is the first substrate.
  • Organic layer The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to one embodiment of the present invention are , is formed by the method described below.
  • Dry processes such as vacuum vapor deposition, ionization vapor deposition, sputtering, and plasma can be used for the organic compound layer that constitutes the organic light-emitting device according to one embodiment of the present invention.
  • a wet process in which a layer is formed by dissolving in an appropriate solvent and using a known coating method (for example, spin coating, dipping, casting method, LB method, inkjet method, etc.) can be used.
  • the film when forming a film by a coating method, the film can be formed by combining with an appropriate binder resin.
  • binder resin examples include polyvinylcarbazole resins, polycarbonate resins, polyester resins, ABS resins, acrylic resins, polyimide resins, phenol resins, epoxy resins, silicone resins, and urea resins, but are not limited to these. .
  • binder resins may be used singly as homopolymers or copolymers, or two or more may be used in combination.
  • additives such as known plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.
  • a light emitting device may have a pixel circuit connected to a light emitting element.
  • the pixel circuit may be of an active matrix type that independently controls light emission of the first light emitting element and the second light emitting element. Active matrix circuits may be voltage programmed or current programmed.
  • the drive circuit has a pixel circuit for each pixel.
  • the pixel circuit includes a light emitting element, a transistor that controls the light emission luminance of the light emitting element, a transistor that controls the light emission timing, a capacitor that holds the gate voltage of the transistor that controls the light emission luminance, and a capacitor for connecting to GND without passing through the light emitting element. It may have a transistor.
  • a light-emitting device has a display area and a peripheral area arranged around the display area.
  • the display area has a pixel circuit
  • the peripheral area has a display control circuit.
  • the mobility of the transistors forming the pixel circuit may be lower than the mobility of the transistors forming the display control circuit.
  • the gradient of the current-voltage characteristics of the transistors that make up the pixel circuit may be smaller than the gradient of the current-voltage characteristics of the transistors that make up the display control circuit.
  • the slope of the current-voltage characteristic can be measured by the so-called Vg-Ig characteristic.
  • a transistor that constitutes a pixel circuit is a transistor that is connected to a light emitting element such as a first light emitting element.
  • An organic light emitting device has a plurality of pixels.
  • a pixel has sub-pixels that emit different colors from each other.
  • the sub-pixels may each have, for example, RGB emission colors.
  • a pixel emits light in a region called a pixel aperture. This area is the same as the first area.
  • the pixel aperture may be 15 ⁇ m or less and may be 5 ⁇ m or more. More specifically, it may be 11 ⁇ m, 9.5 ⁇ m, 7.4 ⁇ m, 6.4 ⁇ m, or the like.
  • the distance between sub-pixels may be 10 ⁇ m or less, specifically 8 ⁇ m, 7.4 ⁇ m, and 6.4 ⁇ m.
  • the pixels can take a known arrangement form in a plan view. Examples may be a stripe arrangement, a delta arrangement, a pentile arrangement, a Bayer arrangement.
  • the shape of the sub-pixel in plan view may take any known shape. For example, a rectangle, a square such as a rhombus, a hexagon, and the like. Of course, if it is not an exact figure but has a shape close to a rectangle, it is included in the rectangle.
  • a combination of sub-pixel shapes and pixel arrays can be used.
  • An organic light-emitting device can be used as a constituent member of a display device or a lighting device.
  • Other applications include exposure light sources for electrophotographic image forming apparatuses, backlights for liquid crystal display devices, and light emitting devices having color filters as white light sources.
  • the display device has an image input unit for inputting image information from an area CCD, a linear CCD, a memory card, etc., has an information processing unit for processing the input information, and displays the input image on the display unit. It may be an image information processing apparatus that
  • the display unit of the imaging device or inkjet printer may have a touch panel function.
  • the driving method of this touch panel function may be an infrared method, a capacitive method, a resistive film method, or an electromagnetic induction method, and is not particularly limited.
  • the display device may also be used as a display section of a multi-function printer.
  • FIG. 1A is a cross-sectional schematic diagram of an example of a pixel that constitutes a display device according to this embodiment.
  • the pixel has sub-pixels 10 .
  • the sub-pixels are divided into 10R, 10G, and 10B according to their light emission.
  • the emission color may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like.
  • Each sub-pixel has a reflective electrode 2 as a first electrode on an interlayer insulating layer 1, an insulating layer 3 covering the edge of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, and a transparent electrode 5. , a protective layer 6 and a color filter 7 .
  • the interlayer insulating layer 1 may have transistors and capacitive elements arranged under or inside it.
  • the transistor and the first electrode may be electrically connected through a contact hole (not shown) or the like.
  • the insulating layer 3 is also called a bank or a pixel isolation film. It covers the edge of the first electrode and surrounds the first electrode. A portion where the insulating layer is not arranged is in contact with the organic compound layer 4 and becomes a light emitting region.
  • the organic compound layer 4 has a hole injection layer 41 , a hole transport layer 42 , a first light emitting layer 43 , a second light emitting layer 44 and an electron transport layer 45 .
  • the second electrode 5 may be a transparent electrode, a reflective electrode, or a transflective electrode.
  • the protective layer 6 reduces penetration of moisture into the organic compound layer. Although the protective layer is shown as one layer, it may be multiple layers. Each layer may have an inorganic compound layer and an organic compound layer.
  • the color filter 7 is divided into 7R, 7G, and 7B according to its color.
  • the color filters may be formed on a planarizing film (not shown).
  • a resin protective layer (not shown) may be provided on the color filter.
  • a color filter may be formed on the protective layer 6 .
  • a polarizing plate may be provided in addition to the color filter.
  • FIG. 1B is a schematic cross-sectional view showing an example of a display device having an organic light emitting element and a transistor connected to the organic light emitting element.
  • a transistor is an example of an active device.
  • the transistors may be thin film transistors (TFTs).
  • a display device 100 in FIG. 1B includes a substrate 11 made of glass, silicon, or the like, and an insulating layer 12 provided thereon.
  • An active element 18 such as a TFT is arranged on the insulating layer, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are arranged.
  • the TFT 18 is also composed of a semiconductor layer 15 , a drain electrode 16 and a source electrode 17 .
  • An insulating film 19 is provided on the TFT 18 .
  • An anode 21 and a source electrode 17 constituting the organic light-emitting element are connected through a contact hole 20 provided in the insulating film.
  • the method of electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the mode shown in FIG. 1B. That is, it is sufficient that either one of the anode or the cathode is electrically connected to one of the TFT source electrode and the TFT drain electrode.
  • TFT refers to a thin film transistor.
  • the organic compound layer is illustrated as one layer, but the organic compound layer 22 may be multiple layers.
  • a first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element.
  • transistors are used as switching elements in the display device 100 of FIG. 1B, other switching elements may be used instead.
  • the transistors used in the display device 100 of FIG. 1B are not limited to transistors using a single crystal silicon wafer, and may be thin film transistors having an active layer on the insulating surface of the substrate.
  • active layers include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide.
  • a thin film transistor is also called a TFT element.
  • a transistor included in the display device 100 of FIG. 1B may be formed in a substrate such as a Si substrate.
  • a substrate such as a Si substrate.
  • formed in a substrate means that a substrate itself such as a Si substrate is processed to fabricate a transistor.
  • having a transistor in a substrate can be regarded as forming the substrate and the transistor integrally.
  • the organic light-emitting element according to the present embodiment is controlled in emission luminance by a TFT, which is an example of a switching element, and by providing the organic light-emitting elements in a plurality of planes, an image can be displayed with each emission luminance.
  • the switching elements according to the present embodiment are not limited to TFTs, and may be transistors made of low-temperature polysilicon, or active matrix drivers formed on a substrate such as a Si substrate. On the substrate can also mean inside the substrate. Whether the transistor is provided in the substrate or the TFT is used is selected depending on the size of the display portion. For example, if the size is about 0.5 inch, it is preferable to provide the organic light emitting element on the Si substrate.
  • FIG. 2 is a schematic diagram showing an example of the display device according to this embodiment.
  • Display device 1000 may have touch panel 1003 , display panel 1005 , frame 1006 , circuit board 1007 , and battery 1008 between upper cover 1001 and lower cover 1009 .
  • the touch panel 1003 and the display panel 1005 are connected to flexible printed circuits FPCs 1002 and 1004 .
  • Transistors are printed on the circuit board 1007 .
  • the battery 1008 may not be provided if the display device is not a portable device, or may be provided at another position even if the display device is a portable device.
  • the display device may have color filters having red, green, and blue.
  • the color filters may be arranged in a delta arrangement of said red, green and blue.
  • the display device may be used in the display section of a mobile terminal. In that case, it may have both a display function and an operation function.
  • Mobile terminals include mobile phones such as smart phones, tablets, head-mounted displays, and the like.
  • the display device may be used in the display section of an imaging device having an optical section having a plurality of lenses and an imaging device that receives light that has passed through the optical section.
  • the imaging device may have a display unit that displays information acquired by the imaging element.
  • the display section may be a display section exposed to the outside of the imaging device, or may be a display section arranged within the viewfinder.
  • the imaging device may be a digital camera or a digital video camera. An imaging device can also be called a photoelectric conversion device.
  • FIG. 3A is a schematic diagram showing an example of an imaging device according to this embodiment.
  • the imaging device 1100 may have a viewfinder 1101 , a rear display 1102 , an operation unit 1103 and a housing 1104 .
  • the viewfinder 1101 may have a display device according to this embodiment.
  • the display device may display not only the image to be captured, but also environmental information, imaging instructions, and the like.
  • the environmental information may include the intensity of outside light, the direction of outside light, the moving speed of the subject, the possibility of the subject being blocked by an obstacle, and the like.
  • a display device using the organic light-emitting device of the present invention Since the best time to take an image is a short amount of time, it is better to display the information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting device of the present invention. This is because the organic light emitting device has a high response speed.
  • a display device using an organic light-emitting element can be used more preferably than these devices and a liquid crystal display device, which require a high display speed.
  • the imaging device 1100 has an optical unit (not shown).
  • the optical unit has a plurality of lenses and forms an image on the imaging device housed in the housing 1104 .
  • the multiple lenses can be focused by adjusting their relative positions. This operation can also be performed automatically.
  • FIG. 3B is a schematic diagram showing an example of the electronic device according to this embodiment.
  • Electronic device 1200 includes display portion 1201 , operation portion 1202 , and housing 1203 .
  • the housing 1203 may include a circuit, a printed board including the circuit, a battery, and a communication portion.
  • the operation unit 1202 may be a button or a touch panel type reaction unit.
  • the operation unit may be a biometric recognition unit that recognizes a fingerprint and performs unlocking or the like.
  • An electronic device having a communication unit can also be called a communication device.
  • the electronic device may further have a camera function by being provided with a lens and an imaging device. An image captured by the camera function is displayed on the display unit. Examples of electronic devices include smartphones, notebook computers, and the like.
  • FIG. 4A and 4B are schematic diagrams showing an example of the display device according to this embodiment.
  • FIG. 4A shows a display device such as a television monitor or a PC monitor.
  • a display device 1300 has a frame 1301 and a display portion 1302 .
  • the light emitting device according to this embodiment may be used for the display unit 1302 .
  • the base 1303 is not limited to the form of FIG. 4A.
  • the lower side of the frame 1301 may also serve as the base.
  • the frame 1301 and the display unit 1302 may be curved. Its radius of curvature may be between 5000 mm and 6000 mm.
  • FIG. 4B is a schematic diagram showing another example of the display device according to this embodiment.
  • a display device 1310 in FIG. 4B is configured to be foldable, and is a so-called foldable display device.
  • the display device 1310 has a first display portion 1311 , a second display portion 1312 , a housing 1313 and a bending point 1314 .
  • the first display unit 1311 and the second display unit 1312 may have the light emitting device according to this embodiment.
  • the first display portion 1311 and the second display portion 1312 may be a seamless display device.
  • the first display portion 1311 and the second display portion 1312 can be separated at a bending point.
  • the first display unit 1311 and the second display unit 1312 may display different images, or the first and second display units may display one image.
  • FIG. 5A is a schematic diagram showing an example of the lighting device according to this embodiment.
  • the illumination device 1400 may have a housing 1401 , a light source 1402 , a circuit board 1403 , an optical film 1404 and a light diffusion section 1405 .
  • the light source may comprise an organic light emitting device according to this embodiment.
  • the optical filter may be a filter that enhances the color rendering of the light source.
  • the light diffusing portion can effectively diffuse the light from the light source such as lighting up and deliver the light over a wide range.
  • the optical filter and the light diffusion section may be provided on the light exit side of the illumination. If necessary, a cover may be provided on the outermost part.
  • a lighting device is, for example, a device that illuminates a room.
  • the lighting device may emit white, neutral white, or any other color from blue to red. It may have a dimming circuit to dim them.
  • the lighting device may have the organic light emitting device of the present invention and a power supply circuit connected thereto.
  • a power supply circuit is a circuit that converts an AC voltage into a DC voltage. Further, white has a color temperature of 4200K, and neutral white has a color temperature of 5000K.
  • the lighting device may have color filters.
  • the lighting device according to this embodiment may have a heat dissipation section.
  • the heat radiating part is for radiating the heat inside the device to the outside of the device, and may be made of metal, liquid silicon, or the like, which has a high specific heat.
  • FIG. 5B is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment.
  • the automobile has a tail lamp, which is an example of a lamp.
  • the automobile 1500 may have a tail lamp 1501, and may be configured to turn on the tail lamp when a brake operation or the like is performed.
  • the tail lamp 1501 may have the organic light emitting device according to this embodiment.
  • the tail lamp may have a protective member that protects the organic EL element.
  • the protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. A furandicarboxylic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.
  • a car 1500 may have a body 1503 and a window 1502 attached thereto.
  • the window may be a transparent display unless it is a window for checking the front and rear of the automobile.
  • the transparent display may comprise an organic light emitting device according to the present embodiments. In this case, constituent materials such as electrodes of the organic light-emitting element are made of transparent members.
  • a mobile object may be a ship, an aircraft, a drone, or the like.
  • the moving body may have a body and a lamp provided on the body.
  • the lighting device may emit light to indicate the position of the aircraft.
  • the lamp has the organic light-emitting element according to this embodiment.
  • the display device can be applied to systems that can be worn as wearable devices such as smart glasses, HMDs, and smart contacts.
  • An imaging display device used in such an application includes an imaging device capable of photoelectrically converting visible light and a display device capable of emitting visible light.
  • FIG. 6A illustrates glasses 1600 (smart glasses) according to one application example.
  • An imaging device 1602 such as a CMOS sensor or SPAD is provided on the surface side of lenses 1601 of spectacles 1600 . Further, the display device of each embodiment described above is provided on the rear surface side of the lens 1601 .
  • the spectacles 1600 further include a control device 1603 .
  • the control device 1603 functions as a power supply that supplies power to the imaging device 1602 and the display device according to each embodiment. Also, the control device 1603 controls operations of the imaging device 1602 and the display device.
  • the lens 1601 is formed with an optical system for condensing light onto the imaging device 1602 .
  • FIG. 6B illustrates glasses 1610 (smart glasses) according to one application.
  • the glasses 1610 have a control device 1612, and the control device 1612 is equipped with an imaging device corresponding to the imaging device 1602 and a display device.
  • An imaging device in the control device 1612 and an optical system for projecting light emitted from the display device are formed in the lens 1611 , and an image is projected onto the lens 1611 .
  • the control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operation of the imaging device and the display device.
  • the control device may have a line-of-sight detection unit that detects the line of sight of the wearer. Infrared rays may be used for line-of-sight detection.
  • the infrared light emitting section emits infrared light to the eyeballs of the user who is gazing at the displayed image.
  • a captured image of the eyeball is obtained by detecting reflected light of the emitted infrared light from the eyeball by an imaging unit having a light receiving element.
  • the user's line of sight to the displayed image is detected from the captured image of the eyeball obtained by capturing infrared light.
  • Any known method can be applied to line-of-sight detection using captured images of eyeballs.
  • line-of-sight detection processing is performed based on the pupillary corneal reflection method.
  • the user's line of sight is detected by calculating a line of sight vector representing the orientation (rotational angle) of the eyeball based on the pupil image and the Purkinje image included in the captured image of the eyeball using the pupillary corneal reflection method. be.
  • a display device may have an imaging device having a light-receiving element, and may control a display image of the display device based on user's line-of-sight information from the imaging device.
  • the display device determines, based on the line-of-sight information, a first visual field area that the user gazes at, and a second visual field area other than the first visual field area.
  • the first viewing area and the second viewing area may be determined by the control device of the display device, or may be determined by an external control device.
  • the display resolution of the first viewing area may be controlled to be higher than the display resolution of the second viewing area. That is, the resolution of the second viewing area may be lower than that of the first viewing area.
  • the display area has a first display area and a second display area different from the first display area. is determined the region where is high.
  • the first viewing area and the second viewing area may be determined by the control device of the display device, or may be determined by an external control device.
  • the resolution of areas with high priority may be controlled to be higher than the resolution of areas other than areas with high priority. In other words, the resolution of areas with relatively low priority may be lowered.
  • AI may be used to determine the first field of view area and areas with high priority.
  • the AI is a model configured to estimate the angle of the line of sight from the eyeball image and the distance to the object ahead of the line of sight, using the image of the eyeball and the direction in which the eyeball of the image was actually viewed as training data. It's okay.
  • the AI program may be possessed by the display device, the imaging device, or the external device. If the external device has it, it is communicated to the display device via communication.
  • display control When display control is performed based on visual recognition detection, it can be preferably applied to smart glasses that further have an imaging device that captures an image of the outside.
  • the smart glasses can display captured external information in real time.
  • Example 1 Evaluation of luminescence properties
  • a toluene solution (1.0 ⁇ 10 ⁇ 5 M) in which the exemplary compound (1) obtained in Synthesis Example 1 was dissolved was prepared, and the emission peak wavelength and the emission peak wavelength were measured using a fluorometer F-4500 (manufactured by Hitachi). Emission intensity at the emission peak wavelength was measured.
  • Comparative Example 1 Comparative compound (1), which is a blue light-emitting material, was also measured in the same manner as in Example 1.
  • Comparative Example 3 Comparative compound (3) having a calculated LUMO value of A of ⁇ 0.65 eV was also measured in the same manner as in Example 1.
  • Comparative Example 4 Comparative compound (4), whose calculated LUMO value of A is ⁇ 0.76 eV, was also measured in the same manner as in Example 1.
  • Comparative Example 5 Comparative compound (5) having a calculated LUMO value of A of ⁇ 1.89 eV was also measured in the same manner as in Example 1.
  • the LUMO of A in the general formula (1) is an appropriate value, so blue light emission can be obtained with high intensity. That is, a highly efficient blue light-emitting material can be obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un élément électroluminescent organique ayant une première électrode, une seconde électrode, et une couche de composé organique disposée entre les première et seconde électrodes, l'élément électroluminescent organique étant caractérisé en ce qu'un composé représenté par la formule générale (1) est utilisé dans la couche électroluminescente. La formule générale (1) comprend une ou plusieurs structures de phénoxazine et un A. A comprend une structure biphényle, une structure terphényle, une structure quaterphényle ou une structure carbazole. La valeur calculée de LUMO de A selon la théorie de la fonctionnelle de la densité (B3LYP/6-31G*) est comprise entre -1,79 eV et -0,77 eV. Cependant, A ne comprend pas les groupes attracteurs d'électrons suivants.
PCT/JP2022/021210 2021-06-11 2022-05-24 Phénoxazines, et élément électroluminescent organique, dispositif d'affichage, dispositif d'imagerie, équipement électronique, dispositif d'éclairage et objet mobile les comprenant WO2022259859A1 (fr)

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