WO2023190159A1 - Composé, matériau d'élément électroluminescent et élément électroluminescent obtenu à l'aide de celui-ci, matériau d'élément de conversion photoélectrique, composition de conversion de couleur, feuille de conversion de couleur, unité de source de lumière, dispositif d'affichage et dispositif d'éclairage - Google Patents

Composé, matériau d'élément électroluminescent et élément électroluminescent obtenu à l'aide de celui-ci, matériau d'élément de conversion photoélectrique, composition de conversion de couleur, feuille de conversion de couleur, unité de source de lumière, dispositif d'affichage et dispositif d'éclairage Download PDF

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WO2023190159A1
WO2023190159A1 PCT/JP2023/011821 JP2023011821W WO2023190159A1 WO 2023190159 A1 WO2023190159 A1 WO 2023190159A1 JP 2023011821 W JP2023011821 W JP 2023011821W WO 2023190159 A1 WO2023190159 A1 WO 2023190159A1
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group
ring
substituted
light emitting
compound
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Japanese (ja)
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大貴 野田
一成 川本
和真 長尾
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東レ株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
    • F21V9/00—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters
    • F21V9/08—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters for producing coloured light, e.g. monochromatic; for reducing intensity of light
    • 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
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00

Definitions

  • the present invention relates to a novel compound and a light emitting device material, a light emitting device, a photoelectric conversion device material, a color conversion composition, a color conversion sheet, a light source unit, a display device, and a lighting device using the same.
  • Organic thin-film light-emitting devices emit light by recombining electrons injected from the cathode and holes injected from the anode in a light-emitting layer sandwiched between the two electrodes.They can be made thinner and have a lower driving voltage. It has characteristics such as high brightness, and the ability to emit multicolor light.
  • an object of the present invention is to provide a compound having high luminous efficiency, excellent durability, and green luminescent properties.
  • the present invention is a compound having a structure represented by the following general formula (1).
  • Ring A 1 and Ring B 1 are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 30 ring carbon atoms, or substituted or unsubstituted aromatic hydrocarbon rings having 5 to 30 ring atoms. It is a group heterocycle.
  • Ring C 1 is a substituted or unsubstituted polycyclic aromatic hydrocarbon having 11 or more and 20 or less ring atoms.
  • Ring D 1 is a substituted or unsubstituted polycyclic aromatic hydrocarbon having 7 or more and 20 or less ring atoms.
  • X is O, N-R A or S
  • R A is an alkyl group, cycloalkyl group, alkenyl group, imino group, aryl group or heteroaryl group. These groups may further have a substituent.
  • R A may further be bonded to ring A 1 or ring B 1 via a linking group to form a ring structure. In that case, the linking group is a single bond, -O-, -S-, >CR A1 R A2 or >SiR A3 R A4 .
  • R A1 to R A4 are each independently hydrogen, halogen, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, and these groups may further have a substituent.
  • R A1 and R A2 or R A3 and R A4 may be further bonded via a linking group.
  • L is a single bond, O, S, >CR A5 R A6 or > SiR A7 R A8 .
  • R A5 to R A8 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these groups further have a substituent. Good too. Furthermore, R A5 and R A6 and R A7 and R A8 may be further bonded via a linking group.
  • the compound of the present invention has green luminescent properties with high luminous efficiency and excellent durability.
  • the polycyclic aromatic compounds described in Patent Documents 1 to 4 have strong and highly planar skeletons, and therefore exhibit high fluorescence quantum yields. Furthermore, since the peak half width at the emission wavelength is small, color purity can be improved.
  • the vibration of the compound having the structure represented by the general formula (1) is restricted, deactivation in the excited state is suppressed, and the light emitting element of the light emitting element is Efficiency and durability can be improved.
  • Ring A 1 and Ring B 1 are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 30 ring carbon atoms, or substituted or unsubstituted aromatic hydrocarbon rings having 5 to 30 ring atoms. It is a group heterocycle.
  • Ring C 1 is a substituted or unsubstituted polycyclic aromatic hydrocarbon having 11 or more and 20 or less ring atoms.
  • Ring D 1 is a substituted or unsubstituted polycyclic aromatic hydrocarbon having 7 or more and 20 or less ring atoms.
  • X is O, N-R A or S
  • R A is an alkyl group, cycloalkyl group, alkenyl group, imino group, aryl group or heteroaryl group. These groups may further have a substituent.
  • R A may further be bonded to ring A 1 or ring B 1 via a linking group to form a ring structure. In that case, the linking group is a single bond, -O-, -S-, >CR A1 R A2 or >SiR A3 R A4 .
  • R A1 to R A4 are each independently hydrogen, halogen, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, and these groups may further have a substituent.
  • R A1 and R A2 or R A3 and R A4 may be further bonded via a linking group.
  • L is a single bond, O, S, >CR A5 R A6 or > SiR A7 R A8 .
  • R A5 to R A8 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these groups further have a substituent. Good too. Furthermore, R A5 and R A6 and R A7 and R A8 may be further bonded via a linking group.
  • L is preferably a single bond.
  • ring C 1 and ring D 1 contain a ring structure represented by any of the following chemical formulas (2-1) to (2-8), and are substituted or unsubstituted.
  • Polycyclic aromatic hydrocarbons are preferred.
  • ring C 1 and ring D 1 are the same.
  • the compound having the structure represented by general formula (1) is more preferably a compound represented by general formula (3) below.
  • R 1 to R 19 are each independently hydrogen, halogen, cyano group, alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, An aryl ether group, an arylthioether group, an aryl group, a heteroaryl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, or a silyl group. These groups may further have a substituent. Among these, hydrogen, an alkyl group, an aryl group, and a heteroaryl group are preferred.
  • Ring A 1 and Ring B 1 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring atoms or a substituted or unsubstituted aromatic heterocycle having 5 to 30 ring atoms. It is. Ring A 1 is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 ring carbon atoms. Ring B 1 is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 ring atoms or a substituted or unsubstituted aromatic heterocycle having 5 to 10 ring atoms.
  • X 1 is O, NR 20 or S
  • R 20 is an alkyl group, cycloalkyl group, alkenyl group, imino group, aryl group or heteroaryl group. These groups may further have a substituent.
  • R 20 may further be bonded to ring A 1 or ring B 1 via a linking group to form a ring structure.
  • the linking group is a single bond, -O-, -S-, >CR 21 R 22 or >SiR 23 R 24 .
  • R 21 to R 24 are each independently hydrogen, halogen, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, and these groups may further have a substituent.
  • R 21 and R 22 or R 23 and R 24 may be further bonded via a linking group.
  • X 1 is preferably NR 20
  • R 20 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkenyl group.
  • a substituted or unsubstituted imino group is preferred.
  • any of the following general formulas (4-1) to (4-5) A compound having the structure represented by the following is more preferable, and can further improve the color purity, light-emitting element efficiency, and durability of the light-emitting element.
  • a compound in which X 1 is NR 20 and R 20 is a substituted or unsubstituted alkenyl group or a substituted or unsubstituted imino group is represented by the following general formula (5-1) or (5-2).
  • a compound having a structure is more preferable, and can further improve the color purity, light-emitting element efficiency, and durability of the light-emitting element.
  • R 1 to R 19 are the same as R 1 to R 19 in general formula (3). .
  • R 201 to R 207 and R 210 to R 214 each independently represent hydrogen, halogen, cyano group, alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, alkynyl group, Formed between an alkoxy group, an alkylthio group, an aryl ether group, an arylthioether group, an aryl group, a heteroaryl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a silyl group, or adjacent groups among these groups. It is a saturated or unsaturated ring.
  • These groups may further have a substituent.
  • Ar 1 to Ar 3 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. .
  • Y 1 to Y 2 are each independently a single bond, O, S, CR 150 R 151 or SiR 152 R 153 , and in general formula (4 In -4) to (4-5), W 1 to W 2 are each independently NR 154 , O or S.
  • R 150 to R 154 each independently represent hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, and these groups may further have a substituent.
  • R 150 and R 151 or R 152 and R 153 may further be bonded via a linking group.
  • the linking group is a single bond, -O-, -S-, >CR 21 R 22 or >SiR 23 R 24 .
  • Y 1 and Y 2 are preferably single bonds from the viewpoint of further improving the color purity, light emitting element efficiency, and durability of the light emitting element.
  • W 3 to W 4 are each independently N or CR 220 .
  • R 220 is hydrogen, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group, and these groups may further have a substituent. From the viewpoint of further improving the color purity, light emitting element efficiency, and durability of the light emitting element, R220 is preferably an aryl group.
  • the isotopic species of hydrogen atoms present in the molecule of the compound of the present invention is not particularly limited.
  • all hydrogen atoms in the molecule may be 1 H, or some or all of them may be 2 H (deuterium D).
  • unsubstituted in the case of “substituted or unsubstituted” means that a hydrogen atom or a deuterium atom is bonded.
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • a cyano group is a group whose structure is represented by -C ⁇ N. Here, it is the carbon atom that is bonded to the other group.
  • 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; It may or may not have.
  • the number of carbon atoms in the alkyl group is not particularly limited, but from the viewpoint of availability and cost, it is preferably in the range of 1 to 20, more preferably 1 to 8.
  • the number of carbon atoms here includes the number of carbon atoms contained in a substituent bonded to an alkyl group, and the same applies to other substituents that define the number of carbon atoms.
  • the cycloalkyl group refers to, for example, a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, or an adamantyl group, which may or may not have a substituent.
  • the number of carbon atoms forming the ring is not particularly limited, but is preferably in the range of 3 or more and 20 or less.
  • the alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, allyl group, butadienyl group, and may or may not have a substituent.
  • the number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • a cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, even if it has a substituent. You don't have to.
  • the number of carbon atoms forming the ring is not particularly limited, but is preferably in the range of 3 or more and 20 or less.
  • the alkynyl group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may or may not have a substituent.
  • the number of carbon atoms in the alkynyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • An alkoxy group refers to a functional group to which an aliphatic hydrocarbon group is bonded via an ether bond, such as a methoxy group, ethoxy group, or propoxy group, and may or may not have a substituent. Good too.
  • the number of carbon atoms in the alkoxy group is not particularly limited, but is preferably in the range of 1 to 20.
  • An alkylthio group is an alkoxy group in which the oxygen atom of the ether bond is replaced with a sulfur atom.
  • the hydrocarbon group of the alkylthio group may or may not have a substituent.
  • the number of carbon atoms in the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20.
  • the aryl ether group refers to a group to which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, which may or may not have a substituent.
  • the number of ring carbon atoms in the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • An arylthioether group is an aryl ether group in which the oxygen atom of the ether bond is replaced with a sulfur atom. This may or may not have substituents.
  • the number of ring carbon atoms in the arylthioether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • Aryl groups include, for example, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, benzophenanthryl group, and benzanthracetyl group.
  • Indicates aromatic hydrocarbon groups such as nyl group, chrysenyl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, benzofluoranthenyl group, dibenzaanthracenyl group, perylenyl group, and helicenyl group. This may or may not have substituents.
  • phenyl group biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, pyrenyl group, fluoranthenyl group, and triphenylenyl group are preferable.
  • the number of carbon atoms forming the ring is not particularly limited, but is preferably in the range of 6 or more and 40 or less, more preferably 6 or more and 30 or less.
  • a substituted phenyl group when there are substituents on two adjacent carbon atoms in the phenyl group, these substituents may form a ring structure with each other.
  • the resulting group is a "substituted phenyl group,” "aryl group having a structure in which two or more rings are condensed,” or "an aryl group having a structure in which two or more rings are condensed.” ⁇ heteroaryl group having a heteroaryl group''.
  • Heteroaryl groups include, for example, pyridyl group, furanyl group, thiophenyl group, quinolinyl group, isoquinolinyl group, pyrazinyl group, pyrimidyl group, pyridazinyl group, triazinyl group, naphthyridinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, Benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, benzocarbazolyl group, carbolinyl group, indolocarbazolyl group, benzofurocarbazolyl group, benzothienocarba Non-carbon groups such as zolyl group, dihydroindenocarbazolyl group, benzoquinolinyl group, acridinyl
  • the naphthyridinyl group refers to any of the following: 1,5-naphthyridinyl group, 1,6-naphthyridinyl group, 1,7-naphthyridinyl group, 1,8-naphthyridinyl group, 2,6-naphthyridinyl group, 2,7-naphthyridinyl group. Show that.
  • a heteroaryl group may or may not have a substituent.
  • the number of ring-forming atoms is not particularly limited, but is preferably in the range of 3 or more and 40 or less, more preferably 3 or more and 30 or less.
  • the amino group is a substituted or unsubstituted amino group.
  • the number of carbon atoms in the amino group is not particularly limited, but is preferably in the range of 2 or more and 50 or less, more preferably 6 or more and 40 or less, particularly preferably 6 or more and 30 or less.
  • a silyl group refers to a functional group to which a substituted or unsubstituted silicon atom is bonded, such as an alkylsilyl group such as a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a propyldimethylsilyl group, or a vinyldimethylsilyl group. and arylsilyl groups such as phenyldimethylsilyl group, tert-butyldiphenylsilyl group, triphenylsilyl group, and trinaphthylsilyl group.
  • the number of carbon atoms in the silyl group is not particularly limited, but is preferably in the range of 1 to 30.
  • the carboxyl group, oxycarbonyl group, and carbamoyl group may or may not have a substituent.
  • substituents include an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and these substituents may be further substituted.
  • the number of carbon atoms in the imino group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • aromatic hydrocarbon rings include a monocyclic benzene ring, a biphenyl ring, a fused bicyclic naphthalene ring, and a tricyclic terphenyl ring (m-terphenyl, o -terphenyl, p-terphenyl), fused tricyclic ring systems such as acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, fused tetracyclic ring system such as triphenylene ring, pyrene ring, naphthacene ring, and fused pentacyclic ring system. Examples include perylene ring and pentacene ring.
  • aromatic heterocycles include pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, and pyrimidine.
  • substituents include halogen, cyano group, alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, and aryl ether group. , an arylthioether group, an aryl group, a heteroaryl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, or a silyl group, and further, specific substituents that are preferred in the description of each substituent. is preferred. Moreover, these substituents may be further substituted with the above-mentioned substituents.
  • a compound having a structure represented by general formula (1) is described, for example, in "Advanced. Materials", 2016, vol. 28, p. It can be produced by referring to the method described in 2777-2781.
  • the obtained compound having the structure represented by the general formula (1) is purified by organic synthesis such as recrystallization and column chromatography, and then further purified by heating under reduced pressure, which is generally called sublimation purification. It is preferable to remove low-boiling components to improve purity.
  • the purity of the compound having the structure represented by general formula (1) is preferably 99% by weight or more from the viewpoint of stabilizing the characteristics of the light emitting device.
  • the peak wavelength is preferably 500 nm or more and 550 nm or less, and more preferably 510 nm or more and 540 nm or less.
  • the emission wavelength of the compound having the structure represented by general formula (1) is measured using a fluorescence spectrophotometer using a diluted solution with a concentration of 10 -5 mol/L using toluene as a solvent. I can do it.
  • the light-emitting element material in the present invention refers to a material that includes a compound having a structure represented by general formula (1) and is used for any layer of a light-emitting element.
  • Examples include materials used for hole injection layers, hole transport layers, light emitting layers, electron transport layers, and/or protective films (cap layers) of electrodes, which will be described later. Among these, it is suitably used for the light emitting layer because it has high light emitting device efficiency and color purity.
  • the light emitting element material may contain other components in addition to the compound having the structure represented by general formula (1).
  • other components include those exemplified as materials constituting a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and/or a protective film (cap layer) of an electrode, which will be described later.
  • the light emitting device of the present invention has a cathode, an anode, and one or more organic layers disposed between them, and emits light using electrical energy. It is preferable that at least one of the organic layers contains a compound having a structure represented by the above-mentioned general formula (1), and this organic layer is a light emitting layer.
  • the light emitting element of the present invention may be either a bottom emission type or a top emission type.
  • a top emission type light emitting element the narrower the half width, the higher the light emitting element efficiency due to the resonance effect of the microcavity. Therefore, it is possible to achieve both color purity and light emitting element efficiency at a higher level.
  • the layer structure between the anode and the cathode in such a light emitting device includes, in addition to the structure consisting only of the light emitting layer, 1) light emitting layer/electron transport layer, 2) hole transport layer/light emitting layer, 3) hole transport layer/emissive layer/electron transport layer, 4) hole injection layer/hole transport layer/emissive layer/electron transport layer, 5) hole transport layer/emissive layer/electron transport layer/electron injection layer, 6) hole Injection layer/hole transport layer/emissive layer/electron transport layer/electron injection layer, 7) hole injection layer/hole transport layer/emissive layer/hole blocking layer/electron transport layer/electron injection layer, 8) positive Examples include a laminated structure such as hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer.
  • the above laminated structure may be a tandem type in which a plurality of layers are laminated with an intermediate layer interposed therebetween.
  • the intermediate layer generally include an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, an intermediate insulating layer, etc., and known material configurations can be used.
  • hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/charge generation layer/hole injection layer/hole transport layer/light emitting layer/electron transport Laminated configurations such as layer/electron injection layer may be mentioned.
  • the light-emitting layers may be the same or different.
  • each of the above layers may be a single layer or multiple layers, and may be doped.
  • a protective layer may be further included, and the light emitting element efficiency can be further improved due to the optical interference effect.
  • the substrate It is preferable to form the light emitting element on a substrate in order to maintain the mechanical strength of the light emitting element, to have little thermal deformation, and to have barrier properties that prevent water vapor and oxygen from entering the light emitting layer.
  • the substrate include, but are not limited to, a glass plate, a ceramic plate, a resin film, a resin thin film, a metal thin plate, and the like.
  • glass substrates are preferably used because they are transparent and easy to process.
  • a glass substrate having high transparency is preferable.
  • resin films and resin thin films obtained by hardening varnish are suitably used for this purpose.
  • resin film a heat-resistant film is used, and specific examples include polyimide film and polyethylene naphthalate film.
  • various wirings, circuits, and switching elements using TFTs may be provided on the surface of the substrate to drive the organic EL.
  • an anode is formed on the substrate.
  • Various wiring, circuits, and switching elements may be interposed between the substrate and the anode.
  • the material used for the anode is not particularly limited as long as it can efficiently inject holes into the organic layer, but in the case of a bottom emission type light emitting element, a transparent or semitransparent electrode is preferable, and in the case of a top emission type light emitting element, In this case, a reflective electrode is preferable.
  • the material for the transparent or translucent electrode examples include conductive metal oxides such as zinc oxide, tin oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO), gold, silver, aluminum, chromium, etc. metals, and conductive polymers such as polythiophene, polypyrrole, and polyaniline.
  • conductive metal oxides such as zinc oxide, tin oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO)
  • gold, silver, aluminum, chromium, etc. metals examples of the material for the transparent or translucent electrode.
  • conductive polymers such as polythiophene, polypyrrole, and polyaniline.
  • ITO indium tin oxide
  • the material for the reflective electrode is preferably one that does not absorb any light and has a high reflectance, such as metals such as aluminum, silver, and platinum.
  • Two or more of these electrode materials may be used, or a plurality of materials may be laminated.
  • the film thickness of the anode is not particularly limited, but is preferably several nm to several hundred nm.
  • the optimal method for forming the anode can be selected depending on the forming material, and examples include sputtering, vapor deposition, and inkjet methods.
  • a sputtering method is preferably used, and when forming an anode using a metal, a vapor deposition method is preferably used.
  • the film thickness of the anode is not particularly limited, it is preferably several nm to several hundred nm.
  • the cathode is preferably formed on the surface opposite to the anode with the organic layer in between, and is particularly preferably formed on the surface of the electron transport layer or the electron injection layer.
  • the material used for the cathode is not particularly limited as long as it can efficiently inject electrons into the light-emitting layer, but in the case of a bottom-emission type light-emitting element, it is preferably a reflective electrode, and in the case of a top-emission type light-emitting element, it is preferably a translucent electrode. Preferably it is an electrode.
  • metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, alloys and multilayer laminated films of these metals and low work function metals such as lithium, sodium, potassium, calcium, and magnesium are used.
  • conductive metal oxides such as zinc oxide, indium tin oxide (ITO), and indium zinc oxide (IZO) are preferable.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • aluminum, silver, and magnesium are preferred as main components from the viewpoints of electrical resistance, ease of film formation, film stability, light emitting device efficiency, and the like.
  • the layer be composed of magnesium and silver because electron injection into the electron transport layer and the electron injection layer becomes easy and driving voltage can be reduced.
  • the material constituting the protective layer is not particularly limited, but includes, for example, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, alloys using these metals, silica, titania, and silicon nitride.
  • metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium
  • alloys using these metals silica, titania, and silicon nitride.
  • examples include inorganic substances, polyvinyl alcohol, polyvinyl chloride, organic polymer compounds such as hydrocarbon polymer compounds, and the like.
  • the material used for the protective layer is preferably selected from materials that are transparent in the visible light region.
  • the hole injection layer is a layer inserted between the anode and the hole transport layer to facilitate hole injection.
  • the hole injection layer may be a single layer or a plurality of layers may be laminated.
  • the presence of a hole injection layer between the hole transport layer and the anode not only allows lower voltage driving and improved durability, but also improves the carrier balance of the device and improves the light emitting device efficiency.
  • a preferable example of the hole injection material is an electron-donating hole injection material (donor material). These materials have a HOMO level shallower than that of the hole transport layer and are close to the work function of the anode, making it possible to reduce the energy barrier with the anode.
  • donor material electron-donating hole injection material
  • Aromatic amine materials such as starburst arylamines such as phenyl)amino)triphenylamine (1-TNATA), carbazole derivatives, pyrazoline derivatives, stilbene compounds, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole
  • heterocyclic compounds such as derivatives, phthalocyanine derivatives, and porphyrin derivatives
  • polymer-based polymers such as polycarbonate and styrene derivatives having the above monomers in their side chains
  • polythiophenes such as PEDOT/PSS
  • polyaniline polyfluorene
  • polyvinylcarbazole polysilane.
  • the hole-injecting material is an electron-accepting hole-injecting material (acceptor material).
  • the hole injection layer may be composed of an acceptor material alone, or may be formed by doping the acceptor material into the donor material.
  • the acceptor material is a material that forms a charge transfer complex with an adjacent hole transport layer when used alone, or with the donor material when used as a dope in the donor material. Use of such a material is more preferable because it contributes to improving the conductivity of the hole injection layer and lowering the driving voltage of the device, thereby improving the efficiency and durability of the light emitting device.
  • Acceptor materials include metal oxides such as molybdenum oxide, vanadium oxide, tungsten oxide, ruthenium oxide, charge transfer complexes such as tris(4-bromophenyl)aminium hexachloroantimonate (TBPAH), 1,4,5, 8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN6), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), fluorine Examples include n-type organic semiconductor compounds such as copper phthalocyanine, fullerene, and the like. When the hole injection layer contains an acceptor compound, the hole injection layer may be composed of one layer or a plurality of laminated layers.
  • 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 a single layer or may be composed of a plurality of laminated layers.
  • the hole transport layer is formed using one type of hole transport material alone or by laminating or mixing two or more types of hole transport materials. Further, it is preferable that the hole transport material has high hole injection efficiency and efficiently transports the injected holes. To this end, it is required that the material has an appropriate ionization potential, high hole mobility, excellent stability, and is unlikely to generate trapping impurities.
  • Substances that meet these conditions include, but are not particularly limited to, benzidine derivatives, an aromatic amine material group called starburst arylamines, carbazole derivatives, pyrazoline derivatives, stilbene compounds, hydrazone compounds, Heterocyclic compounds such as benzofuran derivatives, dibenzofuran derivatives, thiophene derivatives, benzothiophene derivatives, dibenzothiophene derivatives, fluorene derivatives, spirofluorene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives, etc., and in polymer systems, the above monomers are used as side chains. Examples include polycarbonate, styrene derivatives, polythiophene, polyaniline, polyfluorene, polyvinylcarbazole, and polysilane.
  • the light-emitting layer is a layer that emits light due to excitation energy generated by recombination of holes and electrons.
  • the light-emitting layer may be composed of a single material, from the viewpoint of color purity, it is preferable that the light-emitting layer contains a dopant material that emits light with a narrow half-value width and a matrix material.
  • the compound having the structure represented by the general formula (1) has a particularly excellent fluorescence quantum yield, a peak emission wavelength suitable for green emission, a narrow half-width, and a high color purity. Because of its excellent properties, it is preferable to use it as a dopant material for the light-emitting layer.
  • the content of the dopant material in the light emitting layer is preferably 5% by weight or less, more preferably 2% by weight or less, from the viewpoint of further suppressing the concentration quenching phenomenon.
  • the content of the dopant material in the light emitting layer is preferably 0.1% by weight or more, and more preferably 0.5% by weight or more.
  • the matrix material is preferably an organic compound that has a high charge transport ability and a high glass transition temperature.
  • the matrix material include, but are not limited to, compounds having a condensed aryl ring such as naphthacene, pyrene, anthracene, and fluoranthene, and derivatives thereof, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl Aromatic amine derivatives such as -1,1'-diamine, metal chelated oxinoid compounds such as tris(8-quinolinato)aluminum(III), bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives , coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, pyrrolopyrrole derivatives, thiadiazolopyridine derivatives, dibenzofuran derivative
  • a fluorescent material other than the compound having the structure represented by general formula (1) may be contained.
  • compounds having a fused aryl ring such as naphthacene, pyrene, anthracene, and fluoranthene and their derivatives, compounds having a heteroaryl ring and their derivatives, distyrylbenzene derivatives, aminostyryl derivatives, tetraphenylbutadiene derivatives, and stilbene derivatives.
  • a phosphorescent material may be contained as a dopant material.
  • the phosphorescent material includes at least one metal selected from the group consisting of iridium (Ir), ruthenium (Ru), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re).
  • a metal complex compound is preferred, and from the viewpoint of highly efficient light emission, an iridium complex or a platinum complex is more preferred.
  • the ligand preferably has a nitrogen-containing heteroaryl group such as a phenylpyridine skeleton, a phenylquinoline skeleton, or a carbene skeleton, but is not limited thereto.
  • the dopant material is only a compound having a structure represented by general formula (1).
  • the light-emitting layer further contains a compound that exhibits delayed fluorescence.
  • Compounds that exhibit delayed fluorescence have a small energy gap between the singlet excited state and the triplet excited state, causing a transition from the triplet excited state to the singlet excited state, and are materials that can utilize triplet excitons as delayed fluorescence. be.
  • this delayed fluorescence is utilized in an organic light emitting device, the light emitting device efficiency can be further improved.
  • Förster-type energy transfer occurs from the singlet excited state of the compound exhibiting delayed fluorescence to the singlet excited state of the dopant material, fluorescence emission from the singlet excited state of the dopant material is observed.
  • the dopant material is a fluorescent material having a sharp emission wavelength
  • a light emitting element with better light emitting element efficiency and color purity can be obtained.
  • the light-emitting layer contains a compound exhibiting delayed fluorescence
  • the light-emitting element efficiency is further improved, contributing to lower power consumption of the display.
  • the compound exhibiting delayed fluorescence may be a single material or a plurality of materials, such as when forming an exciplex complex.
  • the compound exhibiting delayed fluorescence may be made of a single material or a plurality of materials, and known materials can be used. Specific examples include benzonitrile derivatives, triazine derivatives, disulfoxide derivatives, carbazole derivatives, indolocarbazole derivatives, dihydrophenazine derivatives, thiazole derivatives, and oxadiazole derivatives. Examples of compounds exhibiting such delayed fluorescence include, but are not particularly limited to, the following examples.
  • the light-emitting layer contains a compound having a structure represented by the above-mentioned general formula (1) as a dopant material, preferably further contains a compound exhibiting delayed fluorescence, and further contains a compound exhibiting delayed fluorescence and a matrix material. It is more preferable.
  • the excitation singlet energy of the dopant material is S 1 (1)
  • the excitation singlet energy of the compound exhibiting delayed fluorescence is S 1 (2)
  • the excitation singlet energy of the matrix material is S 1 (3)
  • Equation 1 It is preferable to satisfy the following relationship.
  • the matrix material can have a function of confining the energy of the compound exhibiting delayed fluorescence and the dopant material within the light emitting layer, making it possible to emit light efficiently and further improving the efficiency of the light emitting device.
  • matrix materials that satisfy the relationship of formula 1 with the compound having the structure represented by general formula (1) or the compound exhibiting delayed fluorescence described above include, but are not particularly limited to, the following examples: can be mentioned.
  • the electron transport layer is a layer into which electrons are injected from the cathode and further transports electrons.
  • the electron transport material used in the electron transport layer is required to have high electron affinity, high electron mobility, excellent stability, and be a substance that does not easily generate impurities that become traps. Further, from the viewpoint of suppressing film quality deterioration due to crystallization, a compound having a molecular weight of 400 or more is preferable.
  • the electron transport layer in the present invention also includes a hole blocking layer that can efficiently block the movement of holes.
  • the hole-blocking layer and the electron-transporting layer may be composed of a single layer or a stack of a plurality of materials.
  • electron transport materials include polycyclic aromatic derivatives, styryl aromatic ring derivatives, quinone derivatives, phosphorus oxide derivatives, quinolinol complexes such as tris(8-quinolinolato)aluminum(III), benzoquinolinol complexes, hydroxyazole complexes, and azomethine complexes. , various metal complexes such as tropolone metal complexes and flavonol metal complexes. From the viewpoint of reducing driving voltage and further improving light emitting device efficiency, it is preferable to use a compound having a heteroaryl group containing electron-accepting nitrogen.
  • the electron-accepting nitrogen refers to a nitrogen atom forming multiple bonds with adjacent atoms.
  • heteroaryl group containing electron-accepting nitrogen has a large electron affinity, electrons can be easily injected from the cathode, allowing lower voltage driving. In addition, more electrons are supplied to the light emitting layer, and the probability of recombination increases, so that the light emitting device efficiency is further improved.
  • compounds having a heteroaryl group structure containing electron-accepting nitrogen include pyridine derivatives, triazine derivatives, pyrazine derivatives, pyrimidine derivatives, quinoline derivatives, quinoxaline derivatives, quinazoline derivatives, naphthyridine derivatives, benzoquinoline derivatives, phenanthroline derivatives, and imidazole.
  • Examples include derivatives, oxazole derivatives, thiazole derivatives, triazole derivatives, oxadiazole derivatives, thiadiazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, phenanthroimidazole derivatives, and oligopyridine derivatives such as bipyridine and terpyridine. Two or more types of these may be used.
  • the electron transport material has a condensed polycyclic aromatic skeleton because the glass transition temperature is improved, the electron mobility is large, and the driving voltage can be reduced.
  • a fused polycyclic aromatic skeleton is preferably a quinolinol skeleton, a triazine skeleton, a fluoranthene skeleton, an anthracene skeleton, a pyrene skeleton, or a phenanthroline skeleton.
  • the electron transport layer may contain a donor material.
  • the donor material is a compound that improves the electron injection barrier, facilitates electron injection from the cathode or electron injection layer to the electron transport layer, and further improves the electrical conductivity of the electron transport layer.
  • donor materials include alkali metals such as Li, inorganic salts containing alkali metals such as LiF, complexes of alkali metals and organic substances such as lithium quinolinol, alkaline earth metals, and alkaline earth metals.
  • alkali metals such as Li
  • inorganic salts containing alkali metals such as LiF complexes of alkali metals and organic substances such as lithium quinolinol, alkaline earth metals, and alkaline earth metals.
  • examples include inorganic salts, complexes of alkaline earth metals and organic substances, rare earth metals such as Eu and Yb, inorganic salts containing rare earth metals, and complexes of rare earth metals and organic substances. Two or more types of these may be used. Among these, metallic lithium, rare earth metals, and lithium quinolinol (Liq) are preferred.
  • an electron injection layer may be provided between the cathode and the electron transport layer.
  • the electron injection layer is formed for the purpose of assisting the injection of electrons from the cathode to the electron transport layer, and is composed of a compound having a heteroaryl ring structure containing electron-accepting nitrogen, or the above-mentioned donor material. .
  • triazine derivatives, phenanthroline derivatives, and oligopyridine derivatives are preferred, phenanthroline derivatives and terpyridine derivatives are more preferred, and phenanthroline derivatives having a structure represented by the following general formula (4) are even more preferred. That is, the light emitting device of the present invention preferably contains a phenanthroline derivative having a structure represented by general formula (4) in the electron injection layer.
  • Ar 4 is selected from the group consisting of a p-valent aromatic hydrocarbon group and a p-valent aromatic heterocyclic group.
  • p is a natural number from 1 to 3.
  • R 301 to R 308 may be the same or different, and are selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an aryl group, and a heteroaryl group.
  • the p phenanthrolyl groups can be substituted at any position.
  • aromatic hydrocarbon group examples include, in the case of a monovalent group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a benzo Examples include phenanthryl group, benzanthracenyl group, chrysenyl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, benzofluoranthenyl group, dibenzaanthracenyl group, perylenyl group, and helicenyl group.
  • phenyl group biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, and their hydrogen atoms
  • a group from which at least a part of is removed is preferred.
  • the aromatic hydrocarbon group may or may not have a substituent.
  • the number of carbon atoms forming the ring is not particularly limited, but is preferably in the range of 6 or more and 40 or less, more preferably 6 or more and 30 or less.
  • substituents may form a ring structure.
  • the aromatic heterocyclic group refers to a cyclic aromatic group having one or more atoms other than carbon in the ring, for example, in the case of monovalent, pyridyl group, furanyl group, thiophenyl group, quinolinyl group, isoquinolinyl group, pyrazinyl group.
  • the naphthyridinyl group refers to any of the following: 1,5-naphthyridinyl group, 1,6-naphthyridinyl group, 1,7-naphthyridinyl group, 1,8-naphthyridinyl group, 2,6-naphthyridinyl group, 2,7-naphthyridinyl group. Show that.
  • the aromatic heterocyclic group may or may not have a substituent.
  • the number of carbon atoms forming the ring of the aromatic heterocyclic group is not particularly limited, but is preferably in the range of 2 to 40, more preferably 2 to 30.
  • the aromatic hydrocarbon group or the aromatic heterocyclic group may further have a substituent other than the phenanthryl group.
  • p is preferably 2.
  • an inorganic material such as an insulator or a semiconductor can also be used for the electron injection layer.
  • an inorganic material such as an insulator or a semiconductor can also be used for the electron injection layer. Use of these materials is preferable because short circuits in the light emitting element can be suppressed and electron injection properties can be improved.
  • metal compounds such as alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides are preferable. Two or more types of these may be used.
  • the charge generation layer in the present invention generally consists of a double layer, and specifically can be used as a pn junction charge generation layer consisting of an n-type charge generation layer and a p-type charge generation layer.
  • the pn junction type charge generation layer generates charges or separates the charges into holes and electrons when a voltage is applied in the light emitting element, and transfers these holes and electrons to the hole transport layer and the electron transport layer. injection into the light-emitting layer via the layer. Specifically, it functions as an intermediate charge generation layer in a light emitting element in which light emitting layers are stacked.
  • the n-type charge generation layer supplies electrons to the first light-emitting layer located on the anode side, and the p-type charge generation layer supplies holes to the second light-emission layer located on the cathode side. Therefore, the light emitting element efficiency in a light emitting element in which a plurality of light emitting layers are laminated can be improved, the driving voltage can be reduced, and the durability of the light emitting element is also improved.
  • the n-type charge generation layer consists of an n-type dopant and a host, and conventional materials can be used for these.
  • n-type dopants include alkali metals, alkaline earth metals, rare earth metals, and the like. Two or more types of these may be used. Among these, alkali metals or salts thereof, and rare earth metals are preferred, and lithium metal, lithium fluoride (LiF), lithium quinolinol (Liq), and ytterbium metal are more preferred.
  • examples of the host include triazine derivatives, phenanthroline derivatives, oligopyridine derivatives, and the like. Two or more types of these may be used.
  • the light emitting device of the present invention preferably contains a phenanthroline derivative having a structure represented by general formula (6) in the charge generation layer, and preferably contains a phenanthroline derivative having a structure represented by general formula (7). More preferred.
  • any one of Y 1 to Y 3 is a nitrogen atom, and the others are methine groups.
  • L 2 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted anthrylene group
  • L 3 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group or a substituted or unsubstituted anthrylene group.
  • the substituent is an alkyl group or an alkoxy group.
  • A is a phenyl group or a pyridyl group, and m is 0 or 1.
  • the p-type charge generation layer includes a p-type dopant and a host, and conventional materials can be used for these.
  • a p-type dopant tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)
  • tetracyanoquinodimethane derivatives tetracyanoquinodimethane derivatives
  • radialene derivatives iodine
  • Two or more types of these may be used.
  • arylamine derivatives are preferred.
  • the formation method of each of the above layers constituting the light emitting element may be either a dry process or a wet process, and examples thereof include resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination method, coating method, inkjet method, printing method, etc. . Among these, resistance heating vapor deposition is preferred from the viewpoint of device characteristics.
  • the thickness of the organic layer cannot be limited because it depends on the resistance value of the luminescent material, but it is preferably 1 to 1000 nm.
  • the thickness of each of the light-emitting layer, electron transport layer, and hole transport layer is preferably 1 nm or more and 200 nm or less, 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 electrical energy into light.
  • direct current is mainly used as electrical energy here
  • pulsed current or alternating current can also be used.
  • the current and voltage values There are no particular restrictions on the current and voltage values, and required characteristic values vary depending on the purpose of the device, but from the viewpoint of power consumption and durability of the device, it is preferable that high brightness can be obtained at low voltage.
  • the half-width is preferably 45 nm or less, more preferably 35 nm or less, and 30 nm or less at the emission wavelength when energized. The following are more preferred.
  • the light emitting device according to the embodiment of the present invention can achieve both high light emitting device efficiency and high color purity, and can also be made thinner and lighter, so it can be used, for example, as a display device or a lighting device. Suitably used.
  • Examples of display devices include display devices such as displays that use a matrix method, backlights for various devices, and the like.
  • Backlights are mainly used for the purpose of improving the visibility of display devices such as non-self-luminous displays, and are used in liquid crystal displays, clocks, audio devices, automobile panels, display boards, signs, and the like.
  • liquid crystal displays and in particular, for backlights for personal computers, for which thinning is being considered.
  • Examples of the lighting device include medical lighting, interior lighting, etc., and it is possible to realize a lighting device that combines low power consumption, bright luminous color, and high design.
  • the compounds of the present invention may be used in color conversion compositions that convert incident light from a light emitter, such as a light source, into light of a different wavelength from the incident light. It is preferable that the color conversion composition contains the compound represented by the above-mentioned general formula (1) and a binder resin.
  • converting into light with a wavelength different from that of the incident light preferably means converting into light with a longer wavelength than the incident light.
  • the color conversion composition of the present invention can be prepared by, for example, mixing a binder resin, a compound having a structure represented by general formula (1), and additives and solvents as necessary to a predetermined composition, and then stirring and It can be obtained by homogeneously mixing or kneading using a kneader.
  • the stirring/kneading machine include a homogenizer, a revolution-revolution type stirrer, a three-roller mill, a ball mill, a planetary ball mill, and a bead mill.
  • defoaming is also preferably carried out under vacuum or reduced pressure conditions. Further, certain specific components may be mixed in advance, or treatments such as aging may be performed. It is also possible to remove the solvent with an evaporator to reach the desired solids concentration.
  • the color conversion sheet of the present invention is a sheet that converts incident light from a light emitter such as a light source into light of a wavelength different from that of the incident light, and contains the color conversion composition of the present invention described above. It is preferable to convert the incident light into light with a longer wavelength than that of the incident light.
  • the color conversion sheet of the present invention preferably includes a color conversion layer that is a layer formed from the color conversion composition described above.
  • the amount of residual solvent in the color conversion layer is preferably 0.5% by weight or less from the viewpoint of further improving the durability of the color conversion sheet.
  • the amount of residual solvent in the color conversion layer is preferably 0.1% by weight or more from the viewpoint of further improving the luminous efficiency of the color conversion sheet.
  • a color conversion layer is formed by applying the color conversion composition prepared by the method described above onto a base material and drying it.
  • the binder resin is a thermosetting resin
  • the color conversion composition may be applied onto the base material and then heated and cured to form a color conversion layer
  • the binder resin is a photocurable resin
  • the color conversion composition The material may be applied onto a substrate and then photocured to form a color conversion layer.
  • the light source unit of the present invention includes at least a light source and the color conversion sheet of the present invention described above.
  • the light source included in the light source unit of the present invention serves as a source of the above-mentioned excitation light.
  • the method of arranging the light source and the color conversion sheet is not particularly limited, and the light source and color conversion sheet may be placed in close contact with each other, or a remote phosphor format may be used in which the light source and the color conversion sheet are separated. Good too.
  • the light source unit may further include a color filter for the purpose of increasing color purity.
  • any type of light source can be used as long as it emits light in a wavelength range that can be absorbed by the luminescent material.
  • any light source can be used in principle, such as a hot cathode tube, a cold cathode tube, a fluorescent light source such as an inorganic EL, an organic electroluminescent light source, an LED light source, an incandescent light source, or sunlight.
  • LED is a suitable light source, and for display (display device) and lighting applications, blue LED, which has a light source in the range of 430 to 500 nm, is an even more suitable light source because it can improve the color purity of blue light. be.
  • the light source may have one kind of luminescence peak or two or more kinds of luminescence peaks, but in order to improve color purity, it is preferable to have one kind of luminescence peak. It is also possible to use a plurality of light sources with different types of emission peaks in any combination.
  • the light source unit of the present invention is useful for various light sources such as space lighting and backlighting, and specifically, it can be used for display devices, lighting, interiors, signs, signboards, etc., but especially for display devices and lighting applications. It is particularly suitable for use in
  • the display device of the present invention includes at least the light emitting element of the present invention described above and/or the color conversion sheet described above.
  • the light source unit of the present invention described above is preferably used as a backlight unit in a display device such as a liquid crystal display.
  • a display device such as an organic EL display that displays in a matrix and/or segment format and has high luminous efficiency and excellent durability can be manufactured.
  • the lighting device of the present invention includes at least the light emitting element of the present invention described above and/or the color conversion sheet of the present invention described above.
  • this lighting device emits white light by combining a blue LED light source as a light source unit and a color conversion sheet that converts the blue light from the blue LED light source into light with a longer wavelength.
  • a lighting device can also be obtained using the above-described light emitting element of the present invention.
  • These lighting devices include, for example, medical lighting, interior lighting, and the like, and can achieve both bright luminescent color, high durability, and high design.
  • the compound of the present invention may be used in a photoelectric conversion material constituting a photoelectric conversion layer in a photoelectric conversion element having a photoelectric conversion layer between an anode and a cathode.
  • the photoelectric conversion material may be composed only of the compound having the structure represented by the general formula (1) of the present invention, but may further contain other photoelectric conversion materials in order to further increase the photoelectric conversion efficiency. .
  • Light emitting element characteristics A voltage was applied to the light emitting devices obtained in Examples 24 to 115 and Comparative Examples 7 to 41 so that the current density was 0.1 mA/cm 2 , and a spectral radiance meter CS-1000 manufactured by Konica Minolta, Inc. was used. The emission wavelength was measured using Based on the obtained emission wavelength, the light emitting device efficiency was determined on the assumption that Lambassian radiation was performed.
  • the emission wavelength was similarly measured when a voltage was applied to the light emitting devices obtained in Examples 24 to 115 and Comparative Examples 7 to 41 so that the current density was 10 mA/cm 2 , and the peak wavelength and half wavelength were measured.
  • the price range was calculated.
  • a voltage was applied to the light emitting devices obtained in Examples 24 to 115 and Comparative Examples 7 to 37 so that the current density was 10 mA/cm 2 , and the brightness of the light emitting devices was measured using a photodiode. Luminance. Further, a voltage was continuously applied so that the current density was 10 mA/cm 2 , and the time (LT90) at which the brightness reached 90% of the initial brightness was measured, and this was used as an index of durability.
  • Raw material 1A is published in Journal of American Chemical Society, 2020, vol. 142, p. It can be synthesized by the method disclosed in No. 19468-19472.
  • Raw material 1B is obtained from Angewandte chemie international edition, vol. 59, p. It can be synthesized by the method disclosed in No. 7813-7817.
  • Raw material 1A (5.5 g), raw material 1B (8.6 g), potassium phosphate (3.9 g) and N,N-dimethylformamide (60 ml) were placed in a flask and heated and stirred at 150°C for 6 hours under a nitrogen atmosphere. did. After heating and stirring, the reaction solution was cooled to room temperature, water and toluene were added, and the mixture was separated. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain intermediate INT1 (yield 73%).
  • Compound D-1 was purified by sublimation at 400° C. under a pressure of 1 ⁇ 10 ⁇ 3 Pa using an oil diffusion pump, and then used as a light emitting device material.
  • Table 1 shows the results of evaluating the luminescence properties of Compound D-1.
  • Compound D-2 was purified by sublimation at 400° C. under a pressure of 1 ⁇ 10 ⁇ 3 Pa using an oil diffusion pump, and then used as a light emitting device material.
  • Table 1 shows the results of evaluating the luminescence properties of Compound D-2.
  • Example 24 A glass substrate (manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which a 100 nm thick ITO transparent conductive film was deposited was cut into 38 mm ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned for 15 minutes using "Semico Clean” (registered trademark) 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.), and then washed with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before fabricating the device, placed in a vacuum evaporation device, and evacuated until the degree of vacuum in the device became 5 ⁇ 10 ⁇ 4 Pa or less.
  • "Semico Clean" registered trademark
  • This substrate was subjected to UV-ozone treatment for 1 hour immediately before fabricating the device, placed in a vacuum evaporation device, and evacuated until the degree of vacuum in the device became 5 ⁇ 10 ⁇ 4 Pa or less.
  • HAT-CN6 was deposited to a thickness of 10 nm as a hole injection layer by a resistance heating method.
  • compound HT-1 was deposited to a thickness of 40 nm as a first hole transport layer.
  • compound HT-2 was deposited to a thickness of 10 nm as a second hole transport layer.
  • Compound H-1 was used as a matrix material and Compound D-1 was used as a dopant material, and the dopant material was deposited to a thickness of 20 nm at a doping concentration of 1% by weight.
  • HAT-CN6 , HT-1, HT-2, H-1, ET-1, and 2E-1 are the compounds shown below.
  • Table 2 shows the results of evaluating the obtained light emitting device using the method described above.
  • Example 25-46 Comparative Examples 7-12
  • a light emitting device was produced in the same manner as in Example 24, except that the compounds listed in Table 2 were used as dopant materials, and Table 2 shows the evaluation results.
  • Example 47 A glass substrate (manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which a 100 nm thick ITO transparent conductive film was deposited was cut into 38 mm ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned for 15 minutes using "Semico Clean” (registered trademark) 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.), and then washed with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before fabricating the device, placed in a vacuum evaporation device, and evacuated until the degree of vacuum in the device became 5 ⁇ 10 ⁇ 4 Pa or less.
  • "Semico Clean" registered trademark
  • This substrate was subjected to UV-ozone treatment for 1 hour immediately before fabricating the device, placed in a vacuum evaporation device, and evacuated until the degree of vacuum in the device became 5 ⁇ 10 ⁇ 4 Pa or less.
  • HAT-CN6 was first deposited to a thickness of 10 nm as a hole injection layer, and then HT-3 was deposited to a thickness of 30 nm as a hole transport layer.
  • H-2 is used as a matrix material
  • compound D-1 is used as a dopant material
  • compound H-3 which is a compound showing delayed fluorescence, is mixed in a weight ratio of 79.0:1.0:20. It was deposited to a thickness of 30 nm.
  • ET-2 was laminated to a thickness of 10 nm as a hole blocking layer
  • ET-3 was laminated to a thickness of 40 nm as an electron transport layer.
  • HT-3, H-2, H-3, ET-2, and ET-3 are the compounds shown below.
  • Table 3 shows the results of evaluating the obtained light emitting device using the method described above.
  • Example 48-69 Comparative Examples 13-18
  • a light emitting device was produced in the same manner as in Example 47 except that the compounds listed in Table 3 were used as dopant materials, and Table 3 shows the evaluation results.
  • Example 70 Tandem type light emitting element evaluation
  • a glass substrate manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product
  • the obtained substrate was ultrasonically cleaned for 15 minutes using "Semico Clean” (registered trademark) 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.), and then washed with ultrapure water.
  • This substrate was subjected to UV-ozone treatment for 1 hour immediately before fabricating the device, placed in a vacuum evaporation device, and evacuated until the degree of vacuum in the device became 5 ⁇ 10 ⁇ 4 Pa or less.
  • HAT-CN6 was first deposited to a thickness of 10 nm as a hole injection layer, and then HT-3 was deposited to a thickness of 30 nm as a hole transport layer.
  • a host material (third compound) H-2, a dopant material (first compound) compound G-1, and a TADF material (second compound) compound H-3 are used as a light-emitting layer.
  • ET-2 was laminated to a thickness of 10 nm as a hole blocking layer
  • ET-3 was laminated to a thickness of 40 nm as an electron transport layer.
  • compound ET-4 as an n-type host and metallic lithium as an n-type dopant were laminated to a thickness of 10 nm at a deposition rate ratio of 99:1.
  • HAT-CN6 was laminated to a thickness of 10 nm as a p-type charge generation layer.
  • a 30 nm thick hole transport layer and a 30 nm light emitting layer were formed in the same manner as above.
  • 10 nm of ET-2 was deposited as a hole blocking layer
  • 40 nm of ET-3 was deposited as an electron transport layer.
  • 2E-1 was deposited to a thickness of 0.5 nm as an electron injection layer, and then magnesium and silver were co-deposited to a thickness of 1000 nm to form a cathode, thereby producing a 5 mm x 5 mm square tandem light emitting device.
  • the light emitting device efficiency was 31.8% and the LT90 was 185 hours.
  • Example 71-92 A light emitting device was produced in the same manner as in Example 70, except that the compound listed in Table 4 was used instead of D-1 as the dopant material. The evaluation results are shown in Table 4.
  • Example 93-115 Light emission was carried out in the same manner as in Example 70, except that Compound ET-5 was used instead of Compound ET-4, which is an n-type host, as the n-type charge generation layer, and the compounds listed in Table 4 were used as the dopant materials. The device was fabricated. The evaluation results are shown in Table 4.
  • ET-4, ET-5 and Bphen are the compounds shown below.
  • [1] A compound having a structure represented by the above general formula (1).
  • [2] The compound according to [1], wherein in general formula (1), L is a single bond.
  • [3] A substituted or unsubstituted polycyclic aromatic hydrocarbon in which ring C 1 and ring D 1 contain a ring structure represented by any of the above general formulas (2-1) to (2-8).
  • [4] The compound according to any one of [1] to [3], wherein in general formula (1), ring C 1 and ring D 1 are the same.
  • [5] The compound according to any one of [1] to [4], which has a structure represented by the above general formula (3).
  • the compound having the structure represented by the above general formula (3) has a structure represented by the above general formula (5-1) or (5-2) [5] to [8] Compounds described.
  • a light emitting device material comprising the compound according to any one of [1] to [9].
  • It has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers is described in any one of [1] to [9].
  • a light emitting device containing a compound of [12] The light emitting device according to [11], wherein the organic layer containing the compound according to any one of [1] to [9] is a light emitting layer.
  • Photoelectric conversion element material comprising the compound according to any one of [1] to [9]
  • [21] A color conversion composition that converts incident light into light of a wavelength different from that of the incident light, the color conversion composition containing the compound according to any one of [1] to [9] and a binder resin. thing.
  • [22] A color conversion sheet comprising the color conversion composition according to [21] or a cured product thereof.
  • [23] A light source unit comprising a light source and the color conversion sheet according to [22].
  • a display device comprising the light emitting element according to any one of [11] to [19].
  • [25] A display device including the light source unit according to [23].
  • [26] A lighting device comprising the light emitting element according to any one of [11] to [19].
  • [27] A lighting device including the light source unit according to [23].

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Abstract

Le but de la présente invention est de fournir un composé qui présente une efficacité lumineuse élevée et une excellente durabilité et a des caractéristiques d'émission de lumière verte. La présente invention concerne un composé qui a la structure représentée par la formule générale (1). Dans la formule générale (1), le cycle A1 et le cycle B1 sont chacun un cycle hydrocarboné aromatique substitué ou non substitué ayant de 6 à 30 atomes de carbone formant un cycle ou un cycle hétérocyclique aromatique substitué ou non substitué ayant de 5 à 30 atomes formant un cycle. Le cycle C1 est un hydrocarbure aromatique polycyclique substitué ou non substitué ayant de 11 à 20 atomes formant un cycle. Le cycle D1 est un hydrocarbure aromatique polycyclique substitué ou non substitué ayant de 7 à 20 atomes formant un cycle. X est O, N-RA ou S et RA est un groupe alkyle, un groupe cycloalkyle, un groupe alcényle, un groupe imino, un groupe aryle ou un groupe hétéroaryle. Ces groupes peuvent avoir des groupes substituants. En outre, RA peut se lier au cycle A1 ou au cycle B1 par l'intermédiaire d'un groupe de liaison pour former un cycle. Dans ce cas, le groupe de liaison est une liaison simple, -O-, -S-, >CRA1RA2 ou >SiA3RA4. RA1 à RA4 représentent chacun indépendamment hydrogène, halogène, groupe alkyle, groupe cycloalkyle, groupe aryle ou groupe hétéroaryle et ces groupes peuvent avoir des groupes substituants. En outre, RA1 et RA2 ou RA3 et RA4 peuvent être liés par l'intermédiaire d'un groupe de liaison. L est une liaison simple, O, S, >CRA5RA6 ou >SiRA7RA8. RA5 à RA8 sont chacun indépendamment choisis dans le groupe constitué par un atome d'hydrogène, un atome d'halogène, un groupe alkyle, un groupe cycloalkyle, un groupe aryle et un groupe hétéroaryle, et ces groupes peuvent avoir des groupes substituants. En outre, RA5 et RA6 peuvent être liés par l'intermédiaire d'un groupe de liaison, et RA7 et RA8 peuvent être liés par l'intermédiaire d'un groupe de liaison.
PCT/JP2023/011821 2022-04-01 2023-03-24 Composé, matériau d'élément électroluminescent et élément électroluminescent obtenu à l'aide de celui-ci, matériau d'élément de conversion photoélectrique, composition de conversion de couleur, feuille de conversion de couleur, unité de source de lumière, dispositif d'affichage et dispositif d'éclairage WO2023190159A1 (fr)

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