WO2021149510A1 - Complexe bore-pyrrométhène, élément électroluminescent le contenant, élément électroluminescent, dispositif d'affichage et dispositif d'éclairage - Google Patents

Complexe bore-pyrrométhène, élément électroluminescent le contenant, élément électroluminescent, dispositif d'affichage et dispositif d'éclairage Download PDF

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WO2021149510A1
WO2021149510A1 PCT/JP2021/000458 JP2021000458W WO2021149510A1 WO 2021149510 A1 WO2021149510 A1 WO 2021149510A1 JP 2021000458 W JP2021000458 W JP 2021000458W WO 2021149510 A1 WO2021149510 A1 WO 2021149510A1
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light emitting
groups
aryl
compound
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星野秀尭
長尾和真
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東レ株式会社
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Priority to CN202180007056.8A priority Critical patent/CN114787170A/zh
Priority to JP2021500982A priority patent/JPWO2021149510A1/ja
Priority to KR1020227022664A priority patent/KR102650329B1/ko
Publication of WO2021149510A1 publication Critical patent/WO2021149510A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • C07F5/022—Boron compounds without C-boron linkages
    • 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
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/20—Delayed fluorescence emission
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices

Definitions

  • the present invention relates to a pyrromethene boron complex, a light emitting device containing the pyromethene boron complex, a display device, and a lighting device.
  • the organic thin film light emitting element that emits light by recombining the electrons injected from the cathode and the holes injected from the anode in the light emitting layer sandwiched between the two electrodes is thin, has a low drive voltage, and emits high brightness. Furthermore, it has the feature that multicolor light emission is possible by selecting a light emitting material. In particular, by using a host material and a dopant material in combination for the light emitting layer, it is possible to obtain a light emitting element that emits light of the three primary colors of blue, green, and red with high efficiency.
  • a dye having a high fluorescence quantum yield is usually used.
  • a complex having a pyrromethene skeleton is a compound having requirements necessary for obtaining high efficiency as a dopant such as high fluorescence quantum yield, small Stokes shift and small peak half-value width of emission spectrum, and a pyrromethene complex can be used as a dopant.
  • the light emitting element used is known to exhibit good element characteristics (see, for example, Patent Document 1). Further, in recent years, aiming at high luminous efficiency, a light emitting element containing a TADF (Thermally Activated Fluorescence) material and a pyromethene boron complex has been studied (see, for example, Patent Document 2).
  • TADF Thermally Activated Fluorescence
  • the color gamut is represented by a triangle connecting the coordinates of the vertices indicating the emission of red, green, and blue in the xy chromaticity diagram.
  • Chromaticity is determined by the combination of emission peak wavelength and color purity.
  • the color purity is determined by the width of the emission spectrum, and the narrower the width of the emission spectrum and the closer to monochromatic light, the higher the color purity. Increasing the color purity is particularly important for widening the color gamut, and there is a strong demand for a light emitting material having a sharp emission spectrum.
  • an organic thin film light emitting element when used as a display device or a lighting device, it is required to improve the durability of the light emitting element. In order to improve the durability of the light emitting element, it is necessary to improve the stability of the light emitting material.
  • the organic thin film light emitting element is desired to have high luminous efficiency from the viewpoint of improving brightness and power saving. Especially in mobile display devices whose use has been expanding in recent years, power saving has become a particularly important issue.
  • the pyrromethene boron complex is a useful light emitting material that can obtain a sharp emission spectrum when used as a dopant, but is required to have higher luminous efficiency and higher durability in a light emitting device. ..
  • An object of the present invention is to solve the problems of the prior art and to provide a light emitting material having a high fluorescence quantum yield and a sharp emission spectrum, and a light emitting element having high luminous efficiency, color purity and durability. be.
  • the present invention is a pyrromethene boron complex represented by the general formula (1).
  • R 1 to R 6 are independently hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, respectively. It is selected from the group consisting of an arylthioether group, an aryl group, a heteroaryl group, an amino group, a silyl group, a siloxanyl group and a boryl group. These groups may further have substituents. However, at least one of R 1 to R 4 is a hydrogen atom or an alkyl group.
  • X 1 and X 2 are independently alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, arylether group and arylthioether group, respectively. , Heteroaryl group, halogen, and cyano group. These groups may further have substituents.
  • R 7 is represented by the following general formula (2).
  • R 8 to R 10 are independently hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, arylether group, respectively.
  • R 11 is an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an arylthioether group, an aryl group or a heteroaryl group.
  • Ar 1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • another aspect of the present invention is an element having an anode and a cathode, and a light emitting layer existing between the anode and the cathode, and the light emitting layer emits light by electric energy, and the light emitting layer contains the light emitting layer. It is a light emitting element containing the above-mentioned pyromethene boron complex.
  • the present invention is not limited to the following embodiments, and can be variously modified and implemented according to an object and an application.
  • the pyrromethene boron complex according to the present invention is represented by the general formula (1).
  • R 1 to R 6 are independently hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, respectively. It is selected from the group consisting of an arylthioether group, an aryl group, a heteroaryl group, an amino group, a silyl group, a siloxanyl group and a boryl group. These groups may further have substituents. However, at least one of R 1 to R 4 is a hydrogen atom or an alkyl group.
  • X 1 and X 2 are independently alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, arylether group and arylthioether group, respectively. , Heteroaryl group, halogen, and cyano group. These groups may further have substituents.
  • R 7 is represented by the following general formula (2).
  • R 8 to R 10 are independently hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, arylether group, respectively.
  • R 11 is an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an arylthioether group, an aryl group or a heteroaryl group.
  • Halogen cyano group, aldehyde group, acyl group, carboxyl group, ester group, amide group, sulfonyl group, sulfonic acid ester group, sulfonamide group, amino group, nitro group, silyl group, siroxanyl group, boryl group and phosphine oxide. Selected from the group consisting of groups. These groups may further have substituents.
  • Ar 1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • bridgehead position In pyrromethene skeleton, there is a case where the site to be substituted by R 7 hereinafter referred to as "bridgehead position".
  • a substance having a pyrromethene skeleton represented by the following formula and a substance having a condensed ring structure in a part of the pyrromethene skeleton and having a wide ring structure are collectively referred to as "pyromethene”.
  • hydrogen may be deuterium.
  • the substituents in the case of substitution include an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group and a thiol.
  • unsubstituted means that the atom bonded to the target basic skeleton or group is only a hydrogen atom or a deuterium atom.
  • substituted or unsubstituted in the compound described below or its partial structure.
  • the alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group and a tert-butyl group, which are substituted. It may be non-replaceable.
  • the additional substituent when substituted is not particularly limited, and examples thereof include an alkyl group, a halogen, an aryl group, and a heteroaryl group, and this point is also common to the following description.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 or more and 20 or less, and more preferably 1 or more and 8 or less from the viewpoint of availability and cost.
  • the cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, or an adamantyl group, which may be substituted or unsubstituted.
  • the number of carbon atoms in the alkyl group moiety is not particularly limited, but is preferably in the range of 3 or more and 20 or less.
  • the heterocyclic group refers to an aliphatic ring having an atom other than carbon such as a pyran ring, a piperidine ring, and a cyclic amide in the ring, which may be substituted or unsubstituted.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably in the range of 2 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, an allyl group, or a butadienyl group, which may be substituted or unsubstituted.
  • the carbon number of the alkenyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, etc., which may be substituted or unsubstituted. ..
  • the number of carbon atoms of the cycloalkenyl group is not particularly limited, but is preferably in the range of 3 or more and 20 or less.
  • the alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may be substituted or unsubstituted.
  • the number of carbon atoms of the alkynyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.
  • the alkoxy group refers to a functional group in which an aliphatic hydrocarbon group is bonded via an ether bond such as a methoxy group, an ethoxy group, or a propoxy group, and the aliphatic hydrocarbon group may be substituted or unsubstituted. good.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • the alkylthio group is one in which the oxygen atom of the ether bond of the alkoxy group is replaced with a sulfur atom.
  • the hydrocarbon group of the alkylthio group may be substituted or unsubstituted.
  • the number of carbon atoms of the alkylthio group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • the aryl ether group refers to a functional group in which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may be substituted or unsubstituted.
  • the number of carbon atoms of the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • the arylthio ether group is one in which the oxygen atom of the ether bond of the aryl ether group is replaced with a sulfur atom.
  • the aromatic hydrocarbon group in the arylthioether group may be substituted or unsubstituted.
  • the number of carbon atoms of the arylthioether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • the aryl group may be either a monocyclic ring or a fused ring, and may be, for example, a phenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthrasenyl group, a benzophenanthryl group or a benzo.
  • aromatic hydrocarbon group such as anthrasenyl group, chrysenyl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, benzofluoranthenyl group, dibenzoanthrasenyl group, perylenel group and helisenyl group.
  • a group selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, a pyrenyl group, a fluoranthenyl group and a triphenylenyl group is preferable.
  • the aryl group may be substituted or unsubstituted.
  • a group in which a plurality of phenyl groups such as a biphenyl group and a terphenyl group are bonded via a single bond is treated as a phenyl group having an aryl group as a substituent.
  • the number of carbon atoms of the aryl group is not particularly limited, but is preferably in the range of 6 or more and 40 or less, and more preferably 6 or more and 30 or less. Further, in the case of a phenyl group, when there are substituents on two adjacent carbon atoms in the phenyl group, a ring structure may be formed between these substituents.
  • the heteroaryl group may be either a monocyclic group or a fused ring, and may be, for example, a pyridyl group, a furanyl group, a thiophenyl group, a quinolinyl group, an isoquinolinyl group, a pyrazinyl group, a pyrimidyl group, a pyridadinyl group, a triazinyl group, a naphthyldinyl group, a synnolinyl group, Phtalazinyl group, quinoxalinyl group, quinazolinyl group, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, benzocarbazolyl group, carbolinyl group, indolocarbazolyl group, benzo Flocarbazolyl group, benzothienocarbazolyl group,
  • hetero atom a nitrogen atom, an oxygen atom, or a sulfur atom is preferable.
  • the heteroaryl group may be substituted or unsubstituted.
  • the number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably in the range of 2 or more and 40 or less, and more preferably 2 or more and 30 or less.
  • Halogen refers to an atom selected from fluorine, chlorine, bromine and iodine.
  • the cyano group is a functional group whose structure is represented by -CN. Here, it is the carbon atom that is bonded to the other group.
  • the acyl group refers to a functional group in which an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, etc. are bonded via a carbonyl group, such as an acetyl group, a propionyl group, a benzoyl group, and an acryryl group. .. These substituents may be further substituted.
  • the number of carbon atoms of the acyl group is not particularly limited, but is preferably 2 or more and 40 or less, and more preferably 2 or more and 30 or less.
  • the ester group refers to, for example, a functional group in which an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or the like is bonded via an ester bond. These substituents may be further substituted.
  • the number of carbon atoms of the ester group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • a methyl ester group such as a methoxycarbonyl group, an ethyl ester group such as an ethoxycarbonyl group, a propyl ester group such as a propoxycarbonyl group, a butyl ester group such as a butoxycarbonyl group, and an isopropyl such as an isopropoxymethoxycarbonyl group.
  • examples thereof include an ester group, a hexyl ester group such as a hexyloxycarbonyl group, and a phenyl ester group such as a phenoxycarbonyl group.
  • the amide group refers to, for example, a functional group in which an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group or the like is bonded via an amide bond. These substituents may be further substituted.
  • the number of carbon atoms of the amide group is not particularly limited, but is preferably in the range of 1 or more and 20 or less. More specifically, a methylamide group, an ethylamide group, a propylamide group, a butylamide group, an isopropylamide group, a hexylamide group, a phenylamide group and the like can be mentioned.
  • the number of carbon atoms of the sulfonyl group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • the sulfonic acid ester group refers to, for example, a functional group in which an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group and the like are bonded via a sulfonic acid ester bond.
  • these substituents may be further substituted.
  • the number of carbon atoms of the sulfonic acid ester group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • the sulfonamide group refers to, for example, a functional group in which an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group and the like are bonded via a sulfonamide bond.
  • these substituents may be further substituted.
  • the number of carbon atoms of the sulfonamide group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.
  • the amino group is a substituted or unsubstituted amino group.
  • substituents in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group and a branched alkyl group.
  • aryl group and heteroaryl group a phenyl group, a naphthyl group, a pyridyl group and a quinolinyl group are preferable. These substituents may be further substituted.
  • the number of carbon atoms is not particularly limited, but is preferably 2 or more and 50 or less, more preferably 6 or more and 40 or less, and particularly preferably 6 or more and 30 or less.
  • the silyl group refers to a functional group to which a substituted or unsubstituted silicon atom is bonded, and is, for example, an alkylsilyl group such as a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a propyldimethylsilyl group, or a vinyldimethylsilyl group.
  • arylsilyl groups such as phenyldimethylsilyl group, tert-butyldiphenylsilyl group, triphenylsilyl group and trinaphthylsilyl group.
  • Substituents on silicon may be further substituted.
  • the number of carbon atoms of the silyl group is not particularly limited, but is preferably in the range of 1 or more and 30 or less.
  • the siloxanyl group refers to a silicon compound group via an ether bond such as a trimethylsiloxanyl group. Substituents on silicon may be further substituted.
  • the boryl group is a substituted or unsubstituted boryl group.
  • substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, an alkoxy group and a hydroxyl group, and among them, an aryl group and an aryl ether group are preferable.
  • R 50 and R 51 are each independently selected from the same group as R 1 to R 6.
  • the pyromethene boron complex has a strong and highly flat skeleton, and therefore exhibits a high fluorescence quantum yield. Further, since the peak half width of the emission spectrum is small, efficient emission and high color purity can be achieved in the emission element.
  • the substituent R 7 is introduced into the bridgehead position of the pyrromethene skeleton.
  • the introduction of the R 7, it is possible to provide a high fluorescence quantum yield and semi-width small Pirometenhou boron complex.
  • Ar 1 and R 11 in the substituent R 7 are the above groups, respectively, it is possible to suppress the intramolecular rotation of the bridge head position with respect to the pyrromethene skeleton and cause energy deactivation. It is advantageous for improving the luminous efficiency.
  • R 1 to R 4 is a hydrogen atom or an alkyl group, vibrational relaxation in the excited state can be reduced, and the half width of the emission spectrum can be reduced.
  • the stability of the pyromethene boron complex affects the durability of the light emitting device.
  • R 11 is preferably a bulky substituent, preferably a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and R 4 are selected from the above group and affect the emission peak wavelength, crystallinity, sublimation temperature, etc. of the pyrromethene boron complex. From the viewpoint of reducing the half width of the emission spectrum, R 1 and R 4 are preferably hydrogen atoms or alkyl groups. Further, from the viewpoint of further improving the fluorescence quantum yield, it is more preferable that R 1 and R 4 are alkyl groups.
  • R 2 and R 3 are selected from the above group and mainly affect the emission peak wavelength, the half width of the emission spectrum, the stability, or the crystallinity of the pyrromethene boron complex. At least one or preferably both of R 2 and R 3 are hydrogen atoms, from the viewpoint of making the half-value width of the emission spectrum smaller, improving the stability, and easiness of synthesis including recrystallization. It is preferably a group selected from the group consisting of substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups. Further, from the viewpoint of further reducing the half width, it is more preferable that R 2 and R 3 are alkyl groups.
  • R 5 and R 6 are selected from the above group and mainly affect the emission peak wavelength, the half width of the emission spectrum, the stability, or the crystallinity of the pyrromethene boron complex. From the viewpoint of reducing the half width of the emission spectrum, improving the stability, and easiness of synthesis including recrystallization purification, at least one or preferably both of R 5 and R 6 are hydrogen atoms. Alternatively, it is preferably a substituted or unsubstituted alkyl group.
  • X 1 and X 2 are selected from the above. From the viewpoint of luminescence properties and thermal stability, X 1 and X 2 are selected from the group consisting of an alkoxy group, a haloalkyl group, a haloalkoxy group, an aryl ether group, a haloaryl ether group, a haloaryl group, a halogen atom and a cyano group. It is preferably a group.
  • the haloalkyl group is an alkyl group substituted with at least one halogen.
  • a haloaryl group is an aryl group substituted with at least one halogen.
  • X 1 and X 2 are fluorine atoms, fluorine-containing alkyl groups, and fluorine-containing alkoxy groups. It is more preferably a group selected from the group consisting of a fluorine-containing aryl group and a cyano group, further preferably a fluorine atom or a cyano group, and most preferably a fluorine atom.
  • These are electron-attracting groups, which can reduce the electron density of the pyrromethene skeleton and increase the stability of the compound.
  • the pyrromethene boron complex represented by the general formula (1) is J. Org. Chem., Vol.64, No. 21, pp.7813-7819 (1999), Angew. Chem., Int. Ed. Engl., It can be manufactured by referring to the methods described in vol.36, pp.1333-1335 (1997), Org. Lett., Vol.12, pp.296 (2010), etc.
  • a coupling reaction between a halogenated derivative of the pyromethene boron complex and a boronic acid or boronic acid ester derivative is used. Examples include, but are not limited to, methods of forming carbon-carbon bonds.
  • carbon-nitrogen is used by using a coupling reaction between a halogenated derivative of the pyromethene boron complex and an amine or carbazole derivative. Examples include, but are not limited to, methods of generating bonds.
  • the obtained pyromethene boron complex is subjected to organic synthetic purification such as recrystallization and column chromatography, and then the low boiling point component is removed by purification by heating under reduced pressure, which is generally called sublimation purification, to improve the purity. Is preferable.
  • the heating temperature in the sublimation purification is not particularly limited, but is preferably 330 ° C. or lower, more preferably 300 ° C. or lower, from the viewpoint of preventing thermal decomposition of the pyromethene boron complex.
  • the purity of the pyrromethene boron complex produced in this manner is preferably 99% by weight or more from the viewpoint of enabling the light emitting device to exhibit stable characteristics.
  • the optical properties of the pyrromethene boron complex represented by the general formula (1) can be obtained by measuring the absorption spectrum and the emission spectrum of the diluted solution.
  • the solvent is not particularly limited as long as it dissolves the pyrromethene boron complex and the absorption spectrum of the solvent is transparent and does not overlap with the absorption spectrum of the pyromethene boron complex.
  • toluene and the like are exemplified.
  • the concentration of the solution is not particularly limited as long as it has sufficient absorbance and does not cause concentration dimming, but it is preferably in the range of 1 ⁇ 10 -4 mol / L to 1 ⁇ 10 -7 mol / L.
  • the absorption spectrum can be measured by a general ultraviolet-visible spectrophotometer.
  • the emission spectrum can be measured by a general fluorescence spectrophotometer.
  • the emission spectrum of the light emitted by the pyrromethene boron complex represented by the general formula (1) by irradiation with excitation light is sharp.
  • high brightness and high color purity can be achieved by the resonance effect of the microcavity structure in the top emission element, which is the mainstream in display devices and lighting devices, but when the emission spectrum is sharp, this resonance effect appears more strongly and is high. It is advantageous for efficiency.
  • the half width of the emission spectrum is preferably 60 nm or less, more preferably 50 nm or less, further preferably 45 nm or less, and particularly preferably 28 nm or less.
  • the luminous efficiency of the light emitting element depends on the fluorescence quantum yield of the light emitting material itself. Therefore, it is desired that the fluorescence quantum yield of the light emitting material is as close to 100% as possible.
  • the pyromethene boron complex represented by the general formula (1) has a high fluorescence quantum yield by suppressing rotation and vibration at the bridge head position and reducing heat deactivation by having R 11 and Ar 1 as described above. You can get the rate. From the above viewpoint, the fluorescence quantum yield of the pyrromethene boron complex is preferably 90% or more, more preferably 95% or more. However, the fluorescence quantum yield shown here is obtained by measuring a diluted solution using toluene as a solvent with an absolute quantum yield measuring device.
  • the pyrromethene boron complex represented by the general formula (1) can achieve high luminous efficiency, it is used as a light emitting element material in a light emitting element.
  • the light emitting device material in the present invention represents a material used for any layer of the light emitting device, and is selected from a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, as will be described later.
  • the material used for the protective film (cap layer) of the electrode is also included.
  • the pyrromethene boron complex represented by the general formula (1) has high light emitting performance, and therefore is preferably a material used for the light emitting layer.
  • the light emitting device of the present invention has an anode and a cathode, and an organic layer existing between the anode and the cathode.
  • the organic layer preferably includes at least a light emitting layer, and the light emitting layer is an organic electroluminescent device that emits light by electric energy.
  • the light emitting element of the present invention may be either a bottom emission type or a top emission type.
  • the layer structure of the organic layer between the anode and the cathode includes not only the light emitting layer but also 1) light emitting layer / electron transporting layer, 2) hole transporting layer / light emitting layer, and 3).
  • Hole transport layer / light emitting layer / electron transport layer 4) hole injection layer / hole transport layer / light emitting layer / electron transport layer, 5) hole transport layer / light emitting layer / electron transport layer / electron injection layer, 6 ) Hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer, 7) hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer, 8) Examples thereof include a laminated structure such as a hole injection layer / a hole transport layer / an electron blocking layer / a light emitting layer / a hole blocking layer / an electron transport layer / an electron injection layer.
  • tandem type light emitting element in which a plurality of the above laminated configurations are laminated via an intermediate layer may be used.
  • 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 insulation layer, and the like, and known material configurations can be used.
  • Preferred specific examples of the tandem type light emitting element are 9) 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.
  • Laminated configurations such as transport layer / electron injection layer can be mentioned.
  • each of the above layers may be either a single layer or a plurality of layers, and may be doped. Further, there is also an element configuration including a layer using a capping material for improving the luminous efficiency due to the optical interference effect.
  • the pyrromethene boron complex represented by the general formula (1) may be used for any layer in the above device configuration, but since it has a high fluorescence quantum yield and thin film stability, it is a light emitting layer. It is preferable to use it for.
  • the substrate is not particularly limited, and examples thereof include a glass plate, a ceramic plate, a resin film, a resin thin film, and a metal thin plate.
  • a glass substrate is preferably used from the viewpoint of being transparent and easy to process.
  • a glass substrate having high transparency is preferable for a bottom emission element that extracts light through the substrate.
  • flexible displays and foldable displays are increasing in mobile devices such as smartphones, and resin films and resin thin films obtained by curing varnish are preferably used for this purpose.
  • a heat-resistant film is used as the resin film, and specific examples thereof include a polyimide film and a polyethylene naphthalate film.
  • various wirings, circuits, and TFT switching elements for driving the organic EL may be provided on the surface of the substrate.
  • the anode is formed on the substrate.
  • various wirings, 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 it is preferably a transparent or translucent electrode for a bottom emission type element, and a reflective electrode for a top emission type element. Is preferable.
  • Materials for the transparent or translucent electrode include conductive metal oxides such as zinc oxide, tin oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); or gold, silver, aluminum, chromium and the like.
  • conductive metal oxides such as zinc oxide, tin oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); or gold, silver, aluminum, chromium and the like.
  • Metals; conductive polymers such as polythiophene, polypyrrole, polyaniline and the like are exemplified. However, when a metal is used, it is preferable to reduce the film thickness so that light can be semi-transmitted.
  • ITO indium tin oxide
  • ITO indium tin oxide
  • the material of the reflective electrode is preferably one that does not absorb all light and has high reflectance. Specifically, metals such as aluminum, silver, and platinum are exemplified.
  • the optimum method can be adopted depending on the forming material, and examples thereof include a sputtering method, a vapor deposition method, and an inkjet method.
  • a sputtering method is used when an anode is formed of a metal oxide
  • a thin-film deposition method is used when an anode is formed of a metal.
  • the film thickness of the anode is not particularly limited, but is preferably several nm to several hundred nm.
  • these electrode materials may be used alone, or a plurality of materials may be laminated or mixed.
  • the cathode is formed on the surface opposite the anode with the organic layer in between, and is particularly preferably formed on 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 it is preferably a reflective electrode for a bottom emission type element and a translucent electrode for a top emission type element. Is preferable.
  • Metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium are generally used as cathode materials; these metals are combined with low work function metals such as lithium, sodium, potassium, calcium and magnesium. Alloys and multilayer laminated films; or conductive metal oxides such as zinc oxide, indium tin oxide (ITO), and indium zinc oxide (IZO) are preferable. Among them, a metal selected from aluminum, silver and magnesium as a main component is preferable from the viewpoints of electric resistance value, ease of film formation, film stability, luminous efficiency and the like. Further, when the cathode is composed of magnesium and silver, electron injection into the electron transport layer and the electron injection layer in the present invention becomes easy, and low voltage drive becomes possible, which is preferable.
  • a protective layer (Protective layer) To protect the cathode, it is preferable to laminate a protective layer (cap layer) on the cathode.
  • the material constituting the protective layer is not particularly limited, but for example, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium; alloys using these metals; silica, titania, silicon nitride and the like.
  • Inorganic substances Organic polymer compounds such as polyvinyl alcohol, polyvinyl chloride, and hydrocarbon-based polymer compounds can be mentioned. However, when the light emitting element has an element structure (top emission structure) that extracts light from the cathode side, the material used for the protective layer is selected from materials having light transmission in the visible light region.
  • the hole injection layer is a layer that is inserted between the anode and the hole transport layer to facilitate hole injection.
  • the hole injection layer may be one layer or a plurality of layers may be laminated.
  • the presence of a hole injection layer between the hole transport layer and the anode enables lower voltage drive, which not only improves the durable life of the device, but also improves the carrier balance of the device and improves the luminous efficiency. It is preferable to do so.
  • a preferable example of the hole injection material is an electron donating hole injection material (donor material). These are materials whose HOMO level is shallower than that of the hole transport layer and which is close to the work function of the anode, so that the energy barrier with the anode can be reduced.
  • benzidine derivatives 4,4', 4 "-tris (3-methylphenyl (phenyl) amino) triphenylamine (m-MTDATA), 4,4', 4" -tris (1-naphthyl (1-naphthyl)
  • Aromatic amine materials such as starburst arylamines such as phenyl) amino) triphenylamine (1-TNATA); carbazole derivatives, pyrazoline derivatives, stilben compounds, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiasols.
  • Heterocyclic compounds such as derivatives, phthalocyanine derivatives, and porphyrin derivatives
  • examples of polymer systems include polycarbonate and styrene derivatives having the monomer in the side chain, polythiophene such as PEDOT / PSS, polyaniline, polyfluorene, polyvinylcarbazole, and polysilane. Will be done. These materials may be used alone or in combination of two or more kinds of materials. Further, a plurality of materials may be laminated to form a hole injection layer.
  • the hole injection material is an electron acceptor hole injection material (acceptor material).
  • the hole injection layer may be composed of the acceptor material alone, or the donor material may be doped with the acceptor material.
  • the acceptor material is a material that forms a charge transfer complex between the adjacent hole transport layers when used alone and with the donor material when used by doping the donor material. It is more preferable to use such a material because it contributes to the improvement of the conductivity of the hole injection layer and the decrease of the driving voltage of the element, and the effects of improving the luminous efficiency and improving the durable life can be obtained.
  • 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), N-type organic semiconductor compounds such as fluorinated copper phthalocyanine; fullerene and the like are exemplified.
  • the hole injection layer may be one layer or may be composed of a plurality of layers laminated.
  • 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 formed by laminating a plurality of layers.
  • the hole transport layer is formed by one type of hole transport material alone, or by laminating or mixing two or more types of hole transport materials. Further, the hole transport material preferably has high hole injection efficiency and efficiently transports the injected holes. For that purpose, it is required to be a substance having an appropriate ionization potential, a high hole mobility, excellent stability, and less likely to generate impurities as traps.
  • the substance satisfying such conditions is not particularly limited, but for example, a benzidine derivative, an aromatic amine-based material group called starburst arylamine; a carbazole derivative, a pyrazoline derivative, a stillben-based compound, a hydrazone-based compound, and the like.
  • Heterocyclic compounds such as benzofuran derivatives, dibenzofuran derivatives, thiophene derivatives, benzothiophene derivatives, dibenzothiophene derivatives, fluorene derivatives, spirofluorene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives; Examples thereof include polycarbonate and styrene derivatives, polythiophene, polyaniline, polyfluorene, polyvinylcarbazole and polysilane.
  • the light emitting layer is a layer that emits light by the excitation energy generated by the recombination of holes and electrons.
  • the light emitting layer may be composed of a single material, but from the viewpoint of color purity, it is preferable to have a first compound and a second compound which is a dopant exhibiting strong light emission.
  • Suitable examples of the first compound include a host material responsible for charge transfer and a thermally activated delayed fluorescent compound.
  • the pyrromethene boron complex represented by the general formula (1) is a dopant of the light emitting layer because it has a particularly excellent fluorescence quantum yield and the half width of the emission spectrum is narrow and high color purity can be achieved. It is preferably used as the second compound. If the doping amount of the second compound is too large, a concentration quenching phenomenon occurs. Therefore, it is preferably 20% by weight or less, more preferably 10% by weight or less, and 5% by weight or less, based on the total weight of the light emitting layer. More preferably, 2% by weight or less is most preferable. Further, if the doping concentration is too low, sufficient energy transfer is unlikely to occur. Therefore, the weight is preferably 0.1% by weight or more, more preferably 0.5% by weight or more, based on the weight of the entire light emitting layer.
  • the host material does not have to be limited to only one type of compound, and two or more types may be mixed and used, or may be used in a laminated manner.
  • the host material is not particularly limited, but is a compound having a fused aryl ring such as naphthacene, pyrene, anthracene, and fluoranten and a derivative thereof; N, N'-dinaphthyl-N, N'-diphenyl-4,4'-diphenyl-.
  • Aromatic amine derivatives such as 1,1'-diamine; metal chelated oxynoid compounds such as tris (8-quinolinate) aluminum (III); bisstyryl derivatives such as distyrylbenzene derivatives; tetraphenylbutadiene derivatives, inden derivatives, Cmarin derivative, oxadiazole derivative, pyrolopyridine derivative, perinone derivative, pyrolopyrrole derivative, thiadiazolopyridine derivative, dibenzofuran derivative, carbazole derivative, indolocarbazole derivative, triazine derivative; Derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, polythiophene derivatives and the like can be used. Particularly preferred as the host material are anthracene derivatives or naphthacene derivatives.
  • the dopant material is not particularly limited, but may contain a fluorescent material other than the pyrromethene boron complex represented by the general formula (1).
  • a fluorescent material other than the pyrromethene boron complex represented by the general formula (1).
  • compounds having a condensed aryl ring such as naphthacene, pyrene, anthracene, and fluorantene and derivatives thereof; compounds having a heteroaryl ring and derivatives thereof; dystylylbenzene derivatives, aminostyryl derivatives, tetraphenylbutadiene derivatives, stilben derivatives, Examples thereof include aldazine derivatives, pyromethene derivatives, diketopyrrolo [3,4-c] pyrrole derivatives, coumarin derivatives, azole derivatives and metal complexes thereof, and aromatic amine derivatives.
  • a phosphorescent light emitting material may be contained as a dopant material.
  • the dopant that emits phosphorescent light is at least one metal selected from the group consisting of iridium (Ir), ruthenium (Ru), palladium (Pd), platinum (Pt), osmium (Os), and renium (Re). It is preferably a metal complex compound containing, and an iridium complex or a platinum complex is more preferable from the viewpoint of high-efficiency light emission.
  • the ligand preferably has, but is not limited to, a nitrogen-containing heteroaryl group such as a phenylpyridine skeleton or a phenylquinoline skeleton or a carbene skeleton.
  • the dopant material is preferably a pyrromethene boron complex represented by one kind of general formula (1).
  • the light emitting layer may further contain a third component for adjusting the carrier balance in the light emitting layer and for stabilizing the layer structure of the light emitting layer.
  • a third component a material that does not cause an interaction between the host material and the dopant material is selected.
  • Thermally Activated Delayed Fluorescent Compounds also commonly referred to as TADF materials, reduce the energy gap between the singlet excited state energy level and the triplet excited state energy level to reduce the energy gap from the triplet excited state to singlet. It is a material that promotes inverse intersystem crossing to the term excited state and improves the generation probability of singlet excited states.
  • the difference between the lowest excited singlet energy level and the lowest excited triplet energy level (referred to as ⁇ EST) in the TADF material is preferably 0.3 eV or less.
  • the singlet exciton of the second compound Fluorescent emission is observed.
  • the lowest excited singlet energy level of the first compound is larger than the lowest excited singlet energy level of the second compound.
  • the second compound is a fluorescent light emitting material having a sharp light emitting spectrum, a light emitting element having high efficiency and high color purity can be obtained.
  • the light emitting layer contains a thermally activated delayed fluorescent compound, high-efficiency light emission is possible, which contributes to low power consumption of the display.
  • the Thermally Activated Delayed Fluorescence Compound may be a compound that exhibits Thermally Activated Delayed Fluorescence with a Single Material, or exhibits Thermally Activated Delayed Fluorescence with a plurality of compounds as in the case of forming an exciplex complex. It may be a compound.
  • thermally activated delayed fluorescent compound a single compound or a plurality of compounds may be mixed and used, and known materials can be used. Specific examples thereof include benzonitrile derivatives, triazine derivatives, disulfoxide derivatives, carbazole derivatives, indolocarbazole derivatives, dihydrophenazine derivatives, thiazole derivatives, oxaziazole derivatives and the like.
  • a compound having an electron donating part (donor part) and an electron attracting part (acceptor part) in the same molecule is preferable.
  • the electron donating part (donor part) and the electron attracting part may be directly bonded via a single bond or a spiro bond, or may be bonded via a linking group. Examples of such a compound include a compound containing a structure represented by the following general formula (3).
  • A is an electron attracting part
  • B is an electron donating part
  • L is a linking group.
  • A's are the same or different from each other, and the A's may be bonded to each other to form a ring structure.
  • B's are the same or different from each other, and the B's may be bonded to each other to form a ring structure.
  • L is a directly bonded or substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming atomic ring-forming heteroaromatic ring group having 5 to 30 atoms, and these groups are mutually exclusive. It is a group selected from the group consisting of 2 to 5 linked groups and a methylene group having an alkyl fluoride group.
  • the direct bond includes a single bond and a spiro bond.
  • the heteroaromatic ring group does not include an aromatic amino group having an electron donating property or a ⁇ -electron excess heterocyclic functional group.
  • a and b are independently integers of 1 to 5.
  • a plurality of L may exist in the same molecule.
  • the plurality of L's are the same or different from each other, and the L's may be bonded to each other to form a saturated or unsaturated ring.
  • a plurality of Ls may be connected via A and / or B.
  • a plurality of A and / or B and L are present, a plurality of A and / or B may be bound to the same L or may be bound to different L.
  • the electron donating part indicates a part that is relatively electron-rich with respect to the adjacent part.
  • an aromatic amino group and a ⁇ -electron excess heterocyclic functional group can be mentioned.
  • Examples include linked groups. These groups may or may not be further substituted. Examples of the substituent in the case of substitution include the above-mentioned preferred substituent.
  • the electron attractor part indicates a part that is relatively electron deficient with respect to the adjacent part.
  • a phenyl group having an electron-attracting group or an electron-attracting group as a substituent and a ⁇ -electron-deficient heterocyclic functional group can be mentioned.
  • Specific examples thereof include an electron-attracting group selected from a carbonyl group, a sulfonyl group, a cyano group and a fluorine atom, a phenyl group having an electron-attracting group as a substituent, a pyrimidinyl group and a triazinyl group. These groups may or may not be further substituted. Examples of the substituent in the case of substitution include the above-mentioned preferred substituent.
  • Examples of the aromatic hydrocarbon group having 6 to 30 ring-forming carbon atoms used as the linking group L include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group and a dibenzofluorenyl group.
  • heteroaromatic ring group having 5 to 30 ring-forming atoms used as the linking group L examples include a pyridyl group, a furanyl group, a thiophenyl group, a quinolinyl group, an isoquinolinyl group, a pyrazinyl group, a pyrimidyl group, a pyridadinyl group and a triazinyl group.
  • a family group can be mentioned.
  • As the hetero atom a nitrogen atom, an oxygen atom, or a sulfur atom is preferable.
  • the heteroaromatic ring group may be
  • the thermally activated delayed fluorescent compound is not particularly limited, but examples thereof include the following.
  • the first compound is a thermally activated delayed fluorescent compound and the second compound is a pyrometheneboron complex represented by the general formula (1).
  • the light emitting layer further contains a third compound having a singlet energy larger than that of the first compound.
  • the third compound can have a function of confining the energy of the light emitting material in the light emitting layer, and can efficiently emit light. It is also preferable that the lowest excited triplet energy of the third compound is larger than the lowest excited triplet energy of the first compound.
  • a third compound it is preferable that it is an organic compound having a high charge transporting ability and a high glass transition temperature.
  • the third compound is not particularly limited, and examples thereof include the following.
  • the third compound may be a single compound or may be composed of two or more kinds of materials.
  • the third compound has an electron transporting property and the third compound has a hole transporting property.
  • the charge balance in the light emitting layer is adjusted and the bias of the light emitting region is suppressed to suppress the bias of the light emitting device. It can improve reliability and durability.
  • an excited complex may be formed between the electron-transporting third compound and the hole-transporting third compound. From the above viewpoint, it is preferable that the first compound and the third compound satisfy the relational expressions of the following formulas 1 to 4, respectively.
  • S1 represents the energy level of the lowest excited singlet state of each compound
  • T1 represents the energy level of the lowest excited triplet state of each compound.
  • Examples of the third electron-transporting compound include compounds containing a ⁇ -electron-deficient heteroaromatic ring. Specifically, 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (PBD), 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole (TAZ), 1,3-bis [5- (p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl ] Benzene (OXD-7), 9- [4- (5-phenyl-1,3,4-oxadiazol-2-yl) phenyl] -9H-carbazole (CO11), 2,2', 2'' -(1,3,5-Benzenetriyl) Tris (1-phenyl-1H-benzoimidazole) (TPBI), 2- [3- (dibenzo
  • a compound containing a ⁇ -electron excess type heteroaromatic ring and the like can be mentioned.
  • the electron transport layer is a layer in which electrons are injected from the cathode and further electrons are transported.
  • the electron transport material used for the electron transport layer is required to have a high electron affinity, a high electron mobility, excellent stability, and a substance in which impurities that serve as traps are unlikely to be generated. Further, a compound having a molecular weight of 400 or more is preferable because a compound having a low molecular weight tends to crystallize and deteriorate the film quality.
  • the electron transport layer in the present invention also includes a hole blocking layer capable of efficiently blocking the movement of holes as a synonym.
  • the hole blocking layer and the electron transporting layer may be formed alone or by laminating a plurality of materials.
  • the electron transporting material examples include polycyclic aromatic derivatives, styryl-based aromatic ring derivatives, quinone derivatives, phosphoroxide derivatives, quinolinol complexes such as tris (8-quinolinolate) aluminum (III), benzoquinolinol complexes, hydroxyazole complexes, and azomethine complexes. , Tropolone metal complexes and various metal complexes such as flavonol metal complexes. Since the driving voltage can be reduced and high-efficiency light emission can be obtained, it is preferable to use a compound having a heteroaryl group containing electron-accepting nitrogen.
  • the electron-accepting nitrogen represents a nitrogen atom forming a multiple bond with an adjacent atom.
  • the heteroaryl group containing electron-accepting nitrogen has a large electron affinity, electrons can be easily injected from the cathode, and a lower voltage drive becomes possible. In addition, the supply of electrons to the light emitting layer is increased, and the recombination probability is increased, so that the luminous efficiency is improved.
  • the compound having a heteroaryl group structure containing electron-accepting nitrogen include a pyridine derivative, a triazine derivative, a pyrazine derivative, a pyrimidine derivative, a quinoline derivative, a quinoxaline derivative, a quinazoline derivative, a naphthylidine derivative, a benzoquinoline derivative, a phenanthroline derivative, and an imidazole.
  • Preferred compounds include derivatives, oxazole derivatives, thiazole derivatives, triazole derivatives, oxaziazole derivatives, thiadiazol derivatives, benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, phenanthle midazole derivatives, and oligopyridine derivatives such as bipyridine and tarpyridine.
  • imidazole derivatives such as tris (N-phenylbenzimidazole-2-yl) benzene
  • oxadiazole derivatives such as 1,3-bis [(4-tert-butylphenyl) -1,3,4-oxadiazolyl] phenylene.
  • Triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole; phenanthroline derivatives such as vasocproin and 1,3-bis (1,10-phenanthroline-9-yl) benzene; 2,2 Benzene (benzo [h] quinoline-2-yl) -9,9'-benzoquinoline derivatives such as spirobifluorene; 2,5-bis (6'-(2', 2 "-bipyridyl))-1 , 1-Dimethyl-3,4-diphenylsilol and other bipyridine derivatives; 1,3-bis (4'-(2,2': 6'2 "-terpyridinyl)) benzene and other terpyridine derivatives; bis (1-naphthyl) ) -4- (1,8-naphthylidine-2-yl) naphthylidine derivatives such as phenylphosphine oxide
  • the electron transport material has a condensed polycyclic aromatic skeleton because the glass transition temperature is improved, the electron mobility is large, and the voltage can be lowered.
  • a condensed polycyclic aromatic skeleton a fluoranthene skeleton, an anthracene skeleton, a pyrene skeleton or a phenanthroline skeleton is preferable, and a fluoranthene skeleton or a phenanthroline skeleton is particularly preferable.
  • the electron transport material may be used alone or in combination of two or more. Further, the electron transport layer may contain a donor material.
  • the donor material is a compound that facilitates electron injection from the cathode or the electron injection layer into the electron transport layer by improving the electron injection barrier, and further improves the electrical conductivity of the electron transport layer.
  • the donor material include an alkali metal such as Li, an inorganic salt containing an alkali metal such as LiF, a complex of an alkali metal such as lithium quinolinol and an organic substance, an alkaline earth metal, and an alkaline earth metal.
  • alkali metal such as Li
  • an inorganic salt containing an alkali metal such as LiF
  • a complex of an alkali metal such as lithium quinolinol and an organic substance
  • an alkaline earth metal and an alkaline earth metal.
  • examples thereof 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.
  • metallic lithium, rare earth metal, or lithium quinolinol (Liq) is particularly preferable.
  • 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 and the above-mentioned donor material.
  • a phenanthroline derivative represented by the general formula (4) described later is preferable.
  • an insulator or a semiconductor inorganic substance for the electron injection layer. It is preferable to use these materials because it is possible to prevent a short circuit of the light emitting element and improve the electron injection property.
  • At least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides.
  • the charge generation layer in the present invention is a layer that generates or separates charges by applying a voltage and injects charges into adjacent layers.
  • the charge generation layer may be formed of one layer, or a plurality of layers may be laminated.
  • a layer that easily generates electrons as an electric charge is called an n-type charge generation layer, and a layer that easily generates holes is called a p-type charge generation layer.
  • the charge generation layer is preferably composed of a bilayer, and more preferably a pn junction type charge generation layer composed of an n-type charge generation layer and a p-type charge generation layer.
  • the pn junction type charge generation layer an electric charge is generated by applying a voltage in a light emitting element, or the charge is separated into holes and electrons, and these holes and electrons are separated into a hole transport layer and an electron transport layer. Is injected into the light emitting layer via.
  • the n-type charge generating layer supplies electrons to the first light emitting layer existing on the anode side to supply p-type charges.
  • the generation layer supplies holes to the second light emitting layer existing on the cathode side. Therefore, in a light emitting device having two or more light emitting layers, by having one or more charge generating layers between the light emitting layers, it is possible to further improve the element efficiency and reduce the driving voltage. The durability of the element can be further improved.
  • the n-type charge generation layer is composed of an n-type dopant and an n-type host, and conventional materials can be used for these.
  • the donor material exemplified as the material of the electron transport layer is preferably used.
  • alkali metals or salts thereof and rare earth metals are preferable, and materials selected from metallic lithium, lithium fluoride (LiF), lithium quinolinol (Liq) and metallic ytterbium are more preferable.
  • the n-type host those exemplified as the electron transport material are preferably used.
  • a material selected from a triazine derivative, a phenanthroline derivative and an oligopyridine derivative is preferable, a phenanthroline derivative or a terpyridine derivative is more preferable, and a phenanthroline derivative represented by the following general formula (4) is further preferable. That is, it is preferable that the charge generation layer contains the phenanthroline derivative represented by the general formula (4).
  • Ar 2 is selected from the group consisting of a p-valent aromatic hydrocarbon group and a p-valent heteroaromatic ring group.
  • p is a natural number from 1 to 3.
  • R 15 to R 22 may be the same or different from each other, 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 substitution position by p phenanthrolyl groups is an arbitrary position.
  • aromatic hydrocarbon group and the heteroaromatic ring group examples include those described in the above-mentioned examples of aryl groups and heteroaryl groups, but are not limited thereto.
  • the aromatic hydrocarbon group or heteroaromatic ring group may further have a substituent in addition to the phenanthryl group.
  • p is preferably 2.
  • the p-type charge generation layer is composed of a p-type dopant and a p-type host, and conventional materials can be used for these.
  • the acceptor material exemplified as the material of the hole injection layer, iodine, FeCl 3 , FeF 3 , SbCl 5, and the like are preferably used. Specific examples thereof include HAT-CN6, F4-TCNQ, tetracyanoquinodimethane derivative, radialene derivative, iodine, FeCl 3 , FeF 3 , SbCl 5 and the like.
  • a thin film of the p-type dopant may be formed, and the film thickness is preferably 10 nm or less. Further, an arylamine derivative is preferable as the p-type host.
  • the method for forming each of the above layers constituting the light emitting element may be either a dry process or a wet process, and is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, inkjet method, and printing method. Usually, resistance heating vapor deposition is preferable 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 substance, but it is preferably 1 to 1000 nm.
  • the film thicknesses of the light emitting layer, the electron transport layer, and the hole transport layer are preferably 1 nm or more and 200 nm or less, and more preferably 5 nm or more and 100 nm or less, respectively.
  • the light emitting device has a function of converting electric energy into light.
  • direct current is mainly used as electrical energy, but pulse current and alternating current can also be used.
  • the current value and the voltage value are not particularly limited, and the characteristic values required differ depending on the purpose of the device, but it is preferable that high brightness can be obtained at a low voltage from the viewpoint of power consumption and life of the device.
  • the half width of the light emission spectrum by energization is preferably 60 nm or less, more preferably 50 nm or less, and more preferably 45 nm or less. It is more preferably 30 nm or less, and particularly preferably 30 nm or less.
  • the light emitting device of the present invention has a narrow half width of the light emitting spectrum, it is more preferable to use it as a top emission type light emitting device. Due to the resonance effect of the microcavity, the top emission type light emitting element has higher luminous efficiency as the half width is narrower. Therefore, it is possible to achieve both high color purity and high luminous efficiency.
  • the light emitting element according to the embodiment of the present invention is suitably used as a display device such as a display that displays in a matrix and / or segment system, for example.
  • the light emitting element according to the embodiment of the present invention is preferably used as a backlight for various devices and the like.
  • the backlight is mainly used for the purpose of improving the visibility of display devices such as displays that do not emit light by itself, and is used for display devices such as liquid crystal displays, clocks, audio devices, automobile panels, display boards and signs.
  • the light emitting element of the present invention is preferably used for a liquid crystal display, particularly a backlight for a personal computer whose thinness is being studied, and can provide a backlight thinner and lighter than the conventional one.
  • the light emitting element according to the embodiment of the present invention is preferably used as various lighting devices.
  • the light emitting element according to the embodiment of the present invention can achieve both high luminous efficiency and high color purity, and can be made thinner and lighter, so that low power consumption and bright emission color can be achieved.
  • a lighting device with high design can be realized.
  • reaction product 360 mL of dichloromethane and 5.90 mL of diisopropylethylamine were added and stirred at room temperature for 30 minutes. Further, 4.10 mL of boron trifluorinated diethyl ether complex was added and stirred at room temperature for 4 hours, and then the solvent was distilled off. The mixture was removed, water was added, and the mixture was stirred. The organic layer was separated and washed with saturated brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled off. The obtained reaction product was purified by silica gelation chromatography to obtain 580 mg of a red powder.
  • Sublimation purification was performed to further increase the purity.
  • a metal container containing compound D-1 was placed in a glass tube, and this was heated at 190 ° C. under a pressure of 1 ⁇ 10 -3 Pa using an oil diffusion pump to sublimate compound D-1.
  • the solid adhering to the glass tube wall was recovered and confirmed by LC-MS analysis to have a purity of 99%.
  • reaction product 8.81 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and 200 mL of toluene were placed in a flask and stirred at 40 ° C. for 30 minutes. Then, 17.2 mL of diisopropylethylamine and 12.2 mL of boron trifluorinated diethyl ether complex were added and stirred at room temperature for 30 minutes, and then water was added and stirred. The organic layer was separated and washed with saturated brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled off.
  • DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
  • the obtained reaction product was purified by silica gelation chromatography to obtain 3.63 g of a red powder.
  • the obtained powder was analyzed by 1 H-NMR and LC-MS, and it was confirmed that the red powder was compound D-2 which is a pyrromethene boron complex.
  • 1 1 H-NMR (CDCl 3 (d ppm)): 7.72-7.63 (m, 4H), 7.47 (d, 2H), 7.23-7.12 (m, 8H), 5 .81 (s, 2H), 2.38 (s, 6H), 1.57 (s, 6H), 1.32 (s, 9H), 1.22 (s, 18H) MS (m / z) molecular weight; 721.
  • Sublimation purification was performed to further increase the purity.
  • a metal container containing compound D-2 was placed in a glass tube, and this was heated at 240 ° C. under a pressure of 1 ⁇ 10 -3 Pa using an oil diffusion pump to sublimate compound D-2.
  • the solid adhering to the glass tube wall was recovered and confirmed by LC-MS analysis to have a purity of 99%.
  • the pyrometheneboron complex used in the following examples and comparative examples is the compound shown below.
  • Table 1 shows the molecular weight and luminescence characteristics of these pyrromethene boron complexes measured in a toluene solution.
  • Example 1 Evaluation of fluorescent light emitting element
  • a glass substrate manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product having an ITO transparent conductive film deposited at 165 nm as an anode was cut into a size of 38 ⁇ 46 mm and etched.
  • the obtained substrate was ultrasonically cleaned with "Semicoclean 56" (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, then washed with ultrapure water and dried.
  • This substrate was subjected to UV-ozone treatment for 1 hour immediately before the device was manufactured, placed in a vacuum vapor deposition apparatus, and exhausted until the pressure in the apparatus became 5 ⁇ 10 -4 Pa or less.
  • HAT-CN6 was first deposited at 10 nm as a hole injection layer, and HT-1 was deposited at 50 nm as a hole transport layer.
  • H-1 as a host material and compound D-1 as a dopant material were vapor-deposited to a thickness of 20 nm so that the doping concentration was 1.0% by weight.
  • ET-1 was used as the electron transport layer and 2E-1 was used as the donor material, and the layers were laminated to a thickness of 30 nm so that the vapor deposition rate ratio of ET-1 and 2E-1 was 1: 1.
  • magnesium and silver were co-deposited at 1000 nm to form a cathode, and a 5 ⁇ 5 mm square device was manufactured.
  • the light emitting characteristics were an emission peak wavelength of 529 nm, a half width of 26 nm, and an external quantum efficiency of 4.0%. Further, the durability was evaluated by the time when the initial brightness was continuously energized with a current of 1000 cd / m 2 and the brightness became 90% of the initial brightness (hereinafter referred to as LT90). As a result, the LT90 of this light emitting element was 99 hours.
  • HAT-CN6, HT-1, H-1, ET-1 and 2E-1 are the compounds shown below, respectively.
  • Examples 2 to 15 Comparative Examples 1 to 3 A light emitting device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in Table 2 were used instead of the compound D-1 as the dopant material. The results are shown in Table 2.
  • Example 16 A glass substrate (manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product) having an ITO transparent conductive film deposited at 100 nm as an anode was cut into a size of 38 ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with "Semicoclean 56" (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, and then washed with ultrapure water.
  • “Semicoclean 56" trade name, manufactured by Furuuchi Chemical Co., Ltd.
  • This substrate was subjected to UV-ozone treatment for 1 hour immediately before the device was manufactured, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 -4 Pa or less.
  • HAT-CN6 was first deposited at 10 nm as a hole injection layer, and HT-1 was deposited at 40 nm as a hole transport layer.
  • the host material H-2, the compound D-1, and the TADF material compound H-3 are adjusted to a weight ratio of 79.5: 0.5: 20 to 30 nm. It was deposited to the thickness of.
  • compound ET-1 is used as the electron transport material and 2E-1 is used as the donor material, and the thickness of the compounds ET-1 and 2E-1 is 50 nm so that the vapor deposition rate ratio is 1: 1. It was laminated on the surface. Next, after depositing 2E-1 at 0.5 nm as an electron injection layer, magnesium and silver were co-deposited at 1000 nm to form a cathode, and a 5 ⁇ 5 mm square device was manufactured.
  • H-2 and H-3 are the compounds shown below.
  • Examples 17 to 20 Comparative Examples 4 to 6 A light emitting device was produced and evaluated in the same manner as in Example 16 except that the compounds shown in Table 3 were used as the dopant material. The results are shown in Table 3.
  • a light emitting device having high color purity, luminous efficiency and device durability can be manufactured.
  • the luminous efficiency can be increased in the manufacture of display devices such as displays and lighting devices.
  • Example 21 A glass substrate (manufactured by Geomatec Co., Ltd., 11 ⁇ / ⁇ , sputtered product) having an ITO transparent conductive film deposited at 165 nm as an anode was cut into 38 mm ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with "Semicoclean" 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, and then washed with ultrapure water.
  • “Semicoclean” 56 trade name, manufactured by Furuuchi Chemical Co., Ltd.
  • This substrate was subjected to UV-ozone treatment for 1 hour immediately before the device was manufactured, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 -4 Pa or less.
  • HAT-CN6 was first deposited at 5 nm as a hole injection layer, and then HT-1 was deposited at 50 nm as a hole transport layer.
  • H-1 was used as the hole blocking layer at 10 nm
  • the host material H-1 and the dopant compound D-1 were used as the light emitting layer in a weight ratio of 99.5: 0.5 to 20 nm. It was deposited to a thickness.
  • ET-1 was laminated to a thickness of 10 nm as an electron blocking layer
  • compound ET-3 was laminated to a thickness of 35 nm as an electron transporting layer.
  • the compound ET-3 which is an n-type host
  • metallic lithium which is an n-type dopant
  • HAT-CN6 was laminated at 10 nm as a p-type charge generation layer.
  • a hole transport layer of 50 nm, a hole blocking layer of 10 mn, and a light emitting layer of 20 nm were formed on the hole transport layer in the same manner as described above.
  • ET-2 was deposited at 10 nm as an electron blocking layer
  • ET-3 was deposited at 35 nm as an electron transporting layer.
  • magnesium and silver were co-deposited at 1000 nm to serve as a cathode, and a tandem type light emitting device of 5 mm ⁇ 5 mm square was produced.
  • the light emitting characteristics were an emission peak wavelength of 530 nm, a half width of 25 nm, an external quantum efficiency of 4.3%, and an LT90 of 110 hours. It was confirmed that the durability was improved as compared with Example 1 in which the light emitting layer was only one layer.
  • ET-2 and ET-3 are the compounds shown below.

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Abstract

La présente invention concerne un complexe bore-pyrrométhène représenté par la formule générale (1) qui permet d'obtenir : un matériau électroluminescent ayant un rendement quantique de fluorescence élevé et un spectre d'émission de lumière net ; et un élément électroluminescent ayant une efficacité d'émission de lumière élevée, une pureté de couleur et une durabilité. (R1 à R6 sont chacun indépendamment choisis dans le groupe constitué par un atome d'hydrogène, un groupe alkyle, un groupe cycloalkyle, un groupe hétérocyclique, un groupe alcényle, un groupe cycloalcényle, un groupe alcynyle, un groupe hydroxyle, un groupe thiol, un groupe alcoxy, un groupe alkylthio, un groupe aryle éther, un groupe aryle thioéther, un groupe aryle, un groupe hétéroaryle, un groupe amino, un groupe silyle, un groupe siloxanyle et un groupe boryle ; lesdits groupes peuvent également être des substituants ; ici, au moins l'un parmi R1 à R4 est un atome d'hydrogène ou un groupe alkyle ; X1 et X2 sont chacun indépendamment choisis dans le groupe constitué par un atome d'hydrogène, un groupe alkyle, un groupe cycloalkyle, un groupe hétérocyclique, un groupe alcényle, un groupe cycloalcényle, un groupe alcynyle, un groupe hydroxyle, un groupe thiol, un groupe alcoxy, un groupe alkylthio, un groupe aryle éther, un groupe aryle thioéther, un groupe aryle, un groupe hétéroaryle, un halogène, un groupe cyano, un groupe aldéhyde, un groupe acyle, un groupe carboxyle, un groupe ester, un groupe amide, un groupe sulfonyle, un groupe ester d'acide sulfonique, un groupe sulfonamide, un groupe amino, un groupe nitro, un groupe silyle, un groupe siloxanyle, un groupe boryle et un groupe oxyde de phosphine ; lesdits groupes peuvent également être des substituants ; R7 est représenté par la formule générale (2).) (R8 à R10 sont chacun indépendamment choisis dans le groupe constitué par un atome d'hydrogène, un groupe alkyle, un groupe cycloalkyle, un groupe hétérocyclique, un groupe alcényle, un groupe cycloalcényle, un groupe alcynyle, un groupe hydroxyle, un groupe thiol, un groupe alcoxy, un groupe alkylthio, un groupe aryle éther, un groupe aryle thioéther, un groupe aryle, un groupe hétéroaryle, un halogène, un groupe cyano, un groupe aldéhyde, un groupe acyle, un groupe carboxyle, un groupe ester, un groupe amide, un groupe sulfonyle, un groupe ester d'acide sulfonique, un groupe sulfonamide, un groupe amino, un groupe nitro, un groupe silyle, un groupe siloxanyle, un groupe boryle et un groupe oxyde de phosphine ; lesdits groupes peuvent également être des substituants ; R11 est choisi dans le groupe constitué par un groupe alkyle, un groupe cycloalkyle, un groupe hétérocyclique, un groupe alcényle, un groupe cycloalcényle, un groupe alcynyle, un groupe hydroxyle, un groupe thiol, un groupe alcoxy, un groupe alkylthio, un groupe aryle éther, un groupe aryle thioéther, un groupe aryle, un groupe hétéroaryle, un halogène, un groupe cyano, un groupe aldéhyde, un groupe acyle, un groupe carboxyle, un groupe ester, un groupe amide, un groupe sulfonyle, un groupe ester d'acide sulfonique, un groupe sulfonamide, un groupe amino, un groupe nitro, un groupe silyle, un groupe siloxanyle, un groupe boryle et un groupe oxyde de phosphine ; lesdits groupes peuvent également être des substituants ; Ar1 est un groupe aryle substitué ou non substitué, ou un groupe hétéroaryle substitué ou non substitué.)
PCT/JP2021/000458 2020-01-24 2021-01-08 Complexe bore-pyrrométhène, élément électroluminescent le contenant, élément électroluminescent, dispositif d'affichage et dispositif d'éclairage WO2021149510A1 (fr)

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