WO2024181527A1 - フェナントロリン化合物および有機エレクトロルミネッセンス素子 - Google Patents

フェナントロリン化合物および有機エレクトロルミネッセンス素子 Download PDF

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WO2024181527A1
WO2024181527A1 PCT/JP2024/007517 JP2024007517W WO2024181527A1 WO 2024181527 A1 WO2024181527 A1 WO 2024181527A1 JP 2024007517 W JP2024007517 W JP 2024007517W WO 2024181527 A1 WO2024181527 A1 WO 2024181527A1
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French (fr)
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幸喜 加瀬
炳善 梁
ヒョン旭 車
煕載 金
雄太 平山
秀一 林
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Hodogaya Chemical Co Ltd
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Priority to KR1020257029268A priority patent/KR20250154398A/ko
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
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    • 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
    • H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
    • H—ELECTRICITY
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    • 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
    • H10K59/10—OLED displays
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to a compound suitable for self-luminous electronic elements suitable for various display devices, in particular a phenanthroline compound suitable for organic electroluminescence elements (hereinafter abbreviated as organic EL elements), and to organic EL elements, electronic elements, and electronic devices that use said compound.
  • organic EL elements organic electroluminescence elements
  • Organic EL elements are self-luminous, so they are brighter and have better visibility than liquid crystal elements, and are capable of producing clearer displays, so they have been the subject of vigorous research.
  • C. W. Tang et al. of Eastman Kodak Company made organic EL elements using organic materials practical by developing a layered structure element in which various roles are assigned to each material. They layered a phosphor capable of transporting electrons and an organic material capable of transporting holes, and injected both charges into the phosphor layer to emit light, thereby obtaining a high brightness of 1000 cd/m2 or more at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).
  • An anode, hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, and cathode are sequentially provided on a substrate to create a light-emitting element with a bottom emission structure that emits light from the bottom, thereby achieving high efficiency and durability (see, for example, Non-Patent Document 1).
  • semi-transparent electrodes such as LiF/Al/Ag (see, for example, Non-Patent Document 2), Ca/Mg (see, for example, Non-Patent Document 3), and LiF/MgAg are used for the cathode.
  • the current efficiency was 38 cd/A when there was no capping layer, whereas in a light-emitting element using ZnSe with a thickness of 60 nm as a capping layer, the efficiency was improved by about 1.7 times to 64 cd/A. It has also been shown that the maximum points of the transmittance of the semi-transparent electrode and the capping layer do not necessarily coincide with the maximum points of the efficiency, and that the maximum point of the light extraction efficiency is determined by the interference effect (see, for example, Non-Patent Document 3).
  • Alq3 tris(8-hydroxyquinoline)aluminum
  • Alq3 is known as an organic EL material that is generally used as a green emitting material or an electron transport material, and has a weak absorption in the vicinity of 450 nm, which is close to the emission wavelength of blue emitting materials, so that in the case of blue emitting elements, there are problems such as a decrease in color purity and a decrease in light extraction efficiency.
  • the use of an organic capping layer that exhibits a high refractive index in the emission wavelength range of the element is effective in improving the light extraction efficiency of an organic EL element.
  • the organic capping materials proposed so far do not have a sufficiently high refractive index in the emission wavelength range of the organic EL element, and the reality is that they are unable to sufficiently improve the efficiency of the element.
  • the inventors have conducted extensive research with the aim of providing an organic compound that has a high refractive index and a low extinction coefficient for light with wavelengths of 450 nm to 750 nm. Furthermore, they have conducted extensive research with the aim of providing an organic EL element with high efficiency.
  • phenanthroline compounds have excellent stability and durability in a thin film state, and that by adding a specific aromatic ring group or aromatic heterocyclic group to the phenanthroline compound, a material can be obtained that has a high refractive index and a low extinction coefficient in the wavelength range of 450 nm to 750 nm. They also discovered that by using such a phenanthroline compound as a material for the capping layer, an organic EL element with high luminous efficiency and long life can be realized.
  • the present invention has been proposed based on these findings and specifically has the following configuration.
  • Ar represents an unsubstituted heteroaryl group.
  • L1 and L2 each independently represent a single bond, an arylene group, or a heteroarylene group, and at least one hydrogen atom of the arylene group and the heteroarylene group may be substituted with an atom or group selected from the group consisting of a deuterium atom, a cyano group, a nitro group, a halogen atom, a silyl group, an alkyl group, an alkyloxy group, an alkenyl group, an aryloxy group, an arylalkyloxy group, an aryl group, and a heteroaryl group.
  • X represents a methylene group, an oxygen atom, or a sulfur atom, and at least one hydrogen atom of the methylene group may be substituted with an atom or group selected from the group consisting of a deuterium atom, a cyano group, a nitro group, a halogen atom, a silyl group, an alkyl group, an alkyloxy group, an alkenyl group, an aryloxy group, an arylalkyloxy group, an aryl group, and a heteroaryl group.
  • A represents an unsubstituted phenanthrolinyl group.
  • A represents an unsubstituted 1,10-phenanthrolinyl group, and Ar, L 1 , L 2 and X are as defined in formula (A).
  • X in the general formula (B) is a methylene group, and at least one hydrogen atom of the methylene group may be substituted with an atom or group selected from the group consisting of a deuterium atom, a cyano group, a nitro group, a halogen atom, a silyl group, an alkyl group, an alkyloxy group, an alkenyl group, an aryloxy group, an arylalkyloxy group, an aryl group, and a heteroaryl group.
  • An organic EL element having at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and a capping layer in this order, wherein the capping layer contains a phenanthroline compound represented by the general formula (A) described in 1).
  • the capping layer may be a mixed layer containing two or more kinds of compounds, or may have a laminated structure, and each layer constituting the laminated structure may be a single layer made of one kind of compound, or may be a mixed layer containing two or more kinds of compounds.
  • An electronic device or electronic element having a pair of electrodes and at least one organic layer sandwiched between them, the organic layer containing a phenanthroline compound represented by the general formula (A) described in 1).
  • the phenanthroline compound of the present invention has a high refractive index and a low extinction coefficient for light with wavelengths of 450 nm to 750 nm. Therefore, by using the phenanthroline compound of the present invention as a material for the capping layer, an organic EL element with improved efficiency can be realized.
  • FIG. 1 is a diagram showing an example of the configuration of an organic EL element of the present invention.
  • to is a term that indicates a range, and for example, "5 to 10" means “5 to 10", and the range includes the numbers before and after "to” as the lower and upper limits, and the numerical range expressed using “to” means the range includes the numbers before and after "to” as the lower and upper limits.
  • hydrogen atom means " 1 H (protium)" (normal hydrogen atom)
  • deuterium atom means “ 2 H (deuterium D)”.
  • transparent means that the transmittance of visible light is 50% or more, for example, 80% or more, for example, 90% or more, for example, 99% or more.
  • the transmittance of visible light can be measured by an ultraviolet-visible spectrophotometer.
  • the phenanthroline compound of the present invention has a structure represented by the following general formula (A).
  • Ar represents an unsubstituted heteroaryl group.
  • the "heteroaryl group" of the "unsubstituted heteroaryl group” represented by Ar may be a monocyclic heteroaryl group, or may be composed of a fused ring in which two or more rings are fused.
  • the multiple constituent rings of the fused ring constituting the heteroaryl group may all be heterocycles, or may contain a heterocycle and a hydrocarbon ring (e.g., a benzene ring).
  • the heterocycle and the hydrocarbon ring as constituent rings may be aromatic rings or aliphatic rings, but the fused rings as a whole are aromatic heterocycles.
  • heteroatoms contained in the heteroaryl group include nitrogen atoms, sulfur atoms, and oxygen atoms.
  • the heteroatoms contained in the heteroaryl group may be one or two or more. When the heteroaryl group contains two or more heteroatoms, the heteroatoms may be the same or different.
  • the number of atoms constituting the ring skeleton of the heteroaryl group is, for example, 4 to 40, may be 5 to 20, may be 5 to 16, or may be 6 to 14.
  • the number of carbon atoms in the heteroaryl group is, for example, 3 to 35, and may be 3 to 30 or 2 to 20.
  • heteroaryl group examples include groups selected from heteroaryl groups having 2 to 20 carbon atoms, such as a pyridyl group, a pyrimidinyl group, a triazinyl group, a furyl group, a pyrrolyl group, a thienyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, an oxazolopyridyl group, a quinoxalinyl group, a quinazolinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, an
  • Ar is preferably an unsubstituted 2-benzoxazolyl group, an unsubstituted 2-benzothiazolyl group, an unsubstituted 2-oxazolopyridyl group, an unsubstituted 2-benzofuranyl group, or an unsubstituted 2-benzothienyl group, and more preferably an unsubstituted 2-benzothiazolyl group or an unsubstituted 2-oxazolopyridyl group.
  • L1 and L2 each independently represent a single bond, an arylene group, or a heteroarylene group, and L1 and L2 may be the same or different.
  • the "arylene group" in L1 and L2 may be a monocyclic arylene group, or may be composed of a fused ring in which two or more rings are fused, or a linked ring in which two or more rings are linked by a single bond.
  • each of the rings constituting the fused ring constituting the arylene group may be an aromatic hydrocarbon ring (e.g., a benzene ring) or an aliphatic hydrocarbon ring, but the fused rings as a whole form an aromatic hydrocarbon ring.
  • the number of carbon atoms in the arylene group is, for example, 6 to 40, and may be 6 to 30, 6 to 20, or 6 to 14.
  • Specific examples of the "arylene group” include groups selected from arylene groups having 6 to 30 carbon atoms, such as a phenylene group, a biphenyl-diyl group, a terphenyl-diyl group, a naphthalene-diyl group, an anthracene-diyl group, a phenanthone-diyl group, a fluorene-diyl group, a spirobifluone-diyl group, an indene-diyl group, a pyrene-diyl group, a perylene-diyl group, a fluoranthene-diyl group, and a triphenylene-diyl group.
  • heteroarylene group in L1 and L2
  • the explanation of the "heteroaryl group” in Ar above can be referred to by replacing “heteroaryl group” with “heteroarylene group”.
  • Specific examples of the "heteroaryl group” include divalent groups in which one hydrogen atom has been removed from the specific groups given as examples of the "heteroaryl group” in Ar.
  • L1 and L2 are each independently a single bond or an arylene group, and it is also preferable that at least one of L1 and L2 is a single bond.
  • the arylene group is preferably a phenylene group, and more preferably a 1,4-phenylene group.
  • the arylene group and the heteroarylene group in L1 and L2 may be unsubstituted, or at least one hydrogen atom of the arylene group and the heteroarylene group may be substituted with an atom or group (herein, the "group" may be referred to as a "substituent") selected from the group consisting of a deuterium atom, a cyano group, a nitro group, a halogen atom, a silyl group, an alkyl group, an alkyloxy group, an alkenyl group, an aryloxy group, an arylalkyloxy group, an aryl group, and a heteroaryl group.
  • group may be referred to as a "substituent” selected from the group consisting of a deuterium atom, a cyano group, a nitro group, a halogen atom, a silyl group, an alkyl group, an alkyloxy group, an alkenyl group, an
  • halogen atom examples include the following, respectively.
  • halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms
  • Silyl groups such as a trimethylsilyl group and a triphenylsilyl group
  • a linear or branched alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group
  • Alkenyl groups such as vinyl groups and allyl groups
  • Aryloxy groups such as a phenyloxy group and a tolyloxy group
  • Arylalkyloxy groups such as a benzyloxy group and a phenethyloxy group
  • substituents include an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 2 to 20 carbon atoms. These substituents may be further substituted with an atom or group selected from the group consisting of a deuterium atom, a cyano group, a nitro group, a halogen atom, a silyl group, an alkyl group, an alkyloxy group, an alkenyl group, an aryloxy group, an arylalkyloxy group, an aryl group, and a heteroaryl group.
  • substituents of a benzene ring including a benzene ring which is a constituent ring of a condensed ring
  • the benzene rings substituted with the substituents, or the multiple substituents substituted on the same benzene ring may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.
  • substituents of the methylene group the description of the substituents of the methylene group represented by X below can be referred to.
  • X represents a methylene group, an oxygen atom, or a sulfur atom, and at least one hydrogen atom of the methylene group may be substituted with an atom or group selected from the group consisting of a deuterium atom, a cyano group, a nitro group, a halogen atom, a silyl group, an alkyl group, an alkyloxy group, an alkenyl group, an aryloxy group, an arylalkyloxy group, an aryl group, and a heteroaryl group.
  • X is preferably a substituted or unsubstituted methylene group, and more preferably a dimethylmethylene group or an unsubstituted methylene group.
  • A represents an unsubstituted phenanthrolinyl group.
  • the positions of the nitrogen atoms in the phenanthrolinyl group are not particularly limited, but the 1st and 10th positions are preferred. That is, A in general formula (A) is preferably a 1,10-phenanthrolinyl group, and more preferably a 1,10-phenanthroline-2-yl group.
  • Ar-L 1 - and Ar-L 2 - may be bonded to any position of the benzene ring (the benzene ring constituting the ring skeleton) to which the bond is attached.
  • the phenanthroline compound represented by the general formula (A) has a structure represented by the following general formula (B).
  • A, Ar, L 1 , L 2 and X in the general formula (B) are the same as A, Ar, L 1 , L 2 and X in the general formula (A).
  • A, Ar, L 1 , L 2 and X in the general formula (B) the corresponding descriptions in the general formula (A) can be referred to.
  • the phenanthroline compound represented by the general formula (A) is a novel compound.
  • the compound represented by the general formula (A) can be synthesized, for example, by a known coupling reaction using a palladium catalyst or the like (for example, see Non-Patent Document 4).
  • the method for refining the phenanthroline compound represented by general formula (A) is not particularly limited, and can be any known method used for refining organic compounds, such as purification by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization purification using a solvent, crystallization purification, and sublimation purification, and the compound can be identified by NMR analysis.
  • As physical property values of the phenanthroline compound it is preferable to measure the melting point, glass transition point (Tg), refractive index, and extinction coefficient.
  • the melting point is an index of vapor deposition properties
  • the glass transition point (Tg) is an index of stability in the thin film state
  • the refractive index and extinction coefficient are indexes related to improvement of light extraction efficiency.
  • the melting point and glass transition point (Tg) can be measured using a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS) using powder.
  • the refractive index and extinction coefficient can be measured by creating an 80 nm thin film on a silicon substrate and using a spectrometer (F10-RT-UV, Filmetrics).
  • the phenanthroline compound represented by the general formula (A) of the present invention has (1) a high refractive index in the wavelength range of 450 nm to 750 nm, and (2) a low extinction coefficient.
  • the phenanthroline compound represented by the general formula (A) of the present invention is (3) vapor-depositable, (4) has a high glass transition temperature and is stable in a thin film state, and (5) has high heat resistance. Therefore, the phenanthroline compound represented by the general formula (A) is useful as a material for a capping layer of an organic EL element.
  • capping layer in this specification means a layer disposed on the opposite side (outside) of at least one of a pair of electrodes to the light-emitting layer in an organic EL element having a light-emitting layer disposed between the pair of electrodes.
  • the capping layer containing the compound represented by general formula (A) may be disposed only on the outside of one of the pair of electrodes, or may be disposed on the outside of both electrodes. Note that an organic layer such as a charge transport layer may be disposed between the light-emitting layer and each electrode of the organic EL element to which the capping layer is applied.
  • the organic electroluminescence device (organic EL device) of the present invention has at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and a capping layer in this order, and is characterized in that the capping layer contains a phenanthroline compound represented by general formula (A).
  • a phenanthroline compound represented by general formula (A) please refer to the description in the above section "Phenanthroline compound represented by general formula (A)".
  • an organic EL element for example, in the case of a light-emitting element with a top emission structure, an anode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode and a capping layer are sequentially arranged on a substrate made of glass or the like.
  • an organic EL element having a hole injection layer between the anode and the hole transport layer, an electron blocking layer between the hole transport layer and the light-emitting layer, a hole blocking layer between the light-emitting layer and the electron transport layer, and an electron injection layer between the electron transport layer and the cathode are also included.
  • one organic layer can serve multiple roles, for example, a structure that serves both as a hole injection layer and a hole transport layer, a structure that serves both as a hole transport layer and an electron blocking layer, a structure that serves both as a hole blocking layer and an electron transport layer, and a structure that serves both as an electron transport layer and an electron injection layer can also be used. It is also possible to have a configuration in which two or more organic layers having the same function are laminated, such as a configuration in which two hole transport layers are laminated, a configuration in which two light-emitting layers are laminated, a configuration in which two electron transport layers are laminated, or a configuration in which two capping layers are laminated.
  • the total thickness of each layer of the organic EL element is preferably 200 nm to 750 nm, more preferably 350 nm to 600 nm.
  • the thickness of the capping layer is, for example, preferably 30 nm to 120 nm, more preferably 40 nm to 80 nm. In this case, good light extraction efficiency can be obtained.
  • the thickness of the capping layer can be appropriately changed depending on the type of light emitting material used in the light emitting element, the thickness of the organic EL element other than the capping layer, etc. Each member and each layer constituting the organic EL element will be described below.
  • an electrode material having a large work function such as ITO (indium tin oxide) or gold, is used.
  • arylamine compound having three or more triphenylamine structures in a molecule, and having a structure in which these triphenylamine structures are linked by a single bond or a divalent group not containing a heteroatom, can be mentioned.
  • an arylamine compound for example, a starburst type triphenylamine derivative, various triphenylamine tetramers, and other materials can be mentioned.
  • a porphyrin compound represented by copper phthalocyanine, an acceptor heterocyclic compound such as hexacyanoazatriphenylene, and a coating type polymer material can also be used.
  • the hole injection layer may be composed of a single layer formed by solely depositing one of these hole injection materials, or may be composed of a mixed layer formed by mixing two or more materials.
  • the hole injection layer may have a single layer structure, a laminated structure of layers formed by solely depositing layers or layers formed by mixing layers, or a laminated structure of layers formed by solely depositing layers and layers formed by mixing layers. These materials can be formed into a thin film by known methods such as vapor deposition, spin coating, and ink jet method.
  • benzidine derivatives such as N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (hereinafter abbreviated as TPD), N,N'-diphenyl-N,N'-di( ⁇ -naphthyl)benzidine and N,N,N',N'-tetrabiphenylylbenzidine, as well as 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane, etc.
  • TPD N,N'-diphenyl-N,N'-di(m-tolyl)benzidine
  • TPD N,N'-diphenyl-N,N'-di( ⁇ -naphthyl)benzidine
  • N,N,N',N'-tetrabiphenylylbenzidine N,N,N',N'-tetrabiphenylylbenzidine
  • an arylamine compound having two triphenylamine structures in the molecule it is preferable to use an arylamine compound having two triphenylamine structures in the molecule, and these triphenylamine structures are linked by a single bond or a divalent group not containing a hetero atom, such as N,N,N',N'-tetrabiphenylylbenzidine. It is also preferable to use an arylamine compound having three or more triphenylamine structures in the molecule, and these triphenylamine structures are linked by a single bond or a divalent group not containing a hetero atom, such as various triphenylamine trimers and tetramers.
  • the hole transport layer may be composed of a single layer formed by depositing one of these hole transport materials alone, or may be composed of a mixed layer formed by mixing two or more materials.
  • the hole transport layer may have a single layer structure, a laminate structure in which layers formed by depositing alone or layers formed by mixing are laminated, or a laminate structure in which a layer formed by depositing alone and a layer formed by mixing are laminated.
  • a coating type polymer material such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonate) can be used as the hole injection/transport layer. These materials can be formed into a thin film by known methods such as vapor deposition, spin coating, and inkjet.
  • materials for the hole injection layer and the hole transport layer materials that are normally used for these layers and are doped with a p-type dopant such as trisbromophenylaminehexachloroantimony or a radialene derivative (see, for example, Patent Document 3), as well as polymer compounds that contain the structure of a benzidine derivative such as TPD as a partial structure, can be used.
  • a p-type dopant such as trisbromophenylaminehexachloroantimony or a radialene derivative
  • polymer compounds that contain the structure of a benzidine derivative such as TPD as a partial structure can be used.
  • the organic EL device of the present invention may have an electron blocking layer between the light emitting layer and the hole transport layer.
  • a compound having an electron blocking effect such as a carbazole derivative such as 4,4',4''-tri(N-carbazolyl)triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP) and 2,2-bis(4-carbazol-9-yl-phenyl)adamantane, and a compound having a triphenylsilyl group and a triarylamine structure, such as 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, can be used.
  • TCTA 4,4',4''-tri(N-car
  • the electron blocking layer may be formed as a single layer by forming a film of one of these electron blocking materials alone, or may be formed as a mixed layer by forming a film of a mixture of two or more materials.
  • the electron blocking layer may have a single layer structure, a laminate structure of layers formed independently or in a mixture, or a laminate structure of a layer formed independently and a layer formed in a mixture. These materials can be formed into a thin film by known methods such as vapor deposition, spin coating, and ink jet printing.
  • Light-emitting layer As the material of the light-emitting layer of the organic EL element, light-emitting materials such as metal complexes of quinolinol derivatives such as tris(8-quinolinolato)aluminum (Alq 3 ), various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, and polyparaphenylenevinylene derivatives can be used.
  • the light-emitting layer may be composed of a host material and a dopant material.
  • anthracene derivatives are preferably used, but other than that, the above-mentioned light-emitting materials, heterocyclic compounds having an indole ring as a partial structure of a condensed ring, heterocyclic compounds having a carbazole ring as a partial structure of a condensed ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, and polydialkylfluorene derivatives can be used.
  • quinacridone coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives, and aminostyryl derivatives can be used, and it is particularly preferable to use a green light-emitting material.
  • the light-emitting layer may be composed of a single layer formed by depositing one of the above light-emitting materials alone, or may be composed of a Kondo layer formed by mixing two or more materials (for example, two or more light-emitting materials, or one or more host materials and one or more dopant materials).
  • the light-emitting layer may have a single layer structure, a laminate structure in which layers formed by depositing alone or layers formed by depositing a mixture are laminated, or a laminate structure in which a layer formed by depositing alone and a layer formed by depositing a mixture are laminated.
  • a phosphorescent emitter As the phosphorescent emitter, a phosphorescent emitter of a metal complex such as iridium or platinum can be used.
  • a green phosphorescent emitter such as Ir(ppy) 3 (tris(2-phenylpyridinato)iridium(III)
  • a blue phosphorescent emitter such as FIrpic (bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III)) or FIr6 (bis(2,4-difluorophenylpyridinato)tetrakis(1-pyrazolyl)borateiridium(III))
  • a red phosphorescent emitter such as Btp 2 Ir(acac) (bis(2-benzo[b]thiophen-2-yl-pyridine)(acetylacetonato)irid
  • the light-emitting layer may be composed of only these phosphorescent emitters, or may be composed of a host material and a phosphorescent emitter (for example, a co-deposition film of a host material and a phosphorescent emitter).
  • a hole-injecting/transporting host material carbazole derivatives such as 4,4'-di(N-carbazolyl)biphenyl, TCTA, and mCP can be used, and as an electron-transporting host material, p-bis(triphenylsilyl)benzene and 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) can be used.
  • the amount of phosphorescent material doped into the host material is preferably in the range of 1 to 30 weight percent of the total amount of the light-emitting layer to avoid concentration quenching.
  • the light-emitting material it is also possible to use a material that emits delayed fluorescence, such as a carbazolyldicyanobenzene (CDCB) derivative such as PIC-TRZ, CC2TA, PXZ-TRZ, or 4CzIPN (see, for example, Non-Patent Document 5).
  • a material that emits delayed fluorescence such as a carbazolyldicyanobenzene (CDCB) derivative such as PIC-TRZ, CC2TA, PXZ-TRZ, or 4CzIPN
  • CDCB carbazolyldicyanobenzene
  • the organic EL element of the present invention may have a hole blocking layer between the light emitting layer and the electron transport layer.
  • a hole blocking layer compounds having a hole blocking effect, such as phenanthroline derivatives such as bathocuproine, metal complexes of quinolinol derivatives such as aluminum (III) bis(2-methyl-8-quinolinato)-4-phenylphenolate (hereinafter abbreviated as BAlq), various rare earth complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, and benzoazole derivatives, may be used. These materials may be used as the material of the electron transport layer.
  • the electron blocking layer may be composed of a single layer formed by depositing one of these electron blocking materials alone, or may be composed of a mixed layer formed by mixing two or more materials.
  • the hole blocking layer may have a single layer structure, a laminated structure formed by laminating layers formed by depositing ... These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and ink jet printing.
  • Electrode derivatives As materials for the electron transport layer of the organic EL element, metal complexes of quinolinol derivatives such as Alq3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, benzoazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, and silole derivatives can be used.
  • quinolinol derivatives such as Alq3 and BAlq
  • various metal complexes triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, benzoazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide
  • the electron transport layer may be composed of a single layer formed by depositing one of these electron transport materials alone, or may be composed of a mixed layer formed by mixing two or more materials.
  • the electron transport layer may be a single layer, or may be a laminated structure formed by laminating layers formed by depositing ...
  • Electrode Materials that can be used for the electron injection layer of the organic EL element include alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinol, metal oxides such as aluminum oxide, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs).
  • the electron injection layer can be omitted by suitable selection of the electron transport layer and the cathode.
  • materials that are typically used for the electron injection layer and electron transport layer can be doped with an n-type metal dopant such as cesium.
  • Electrode electrode Materials used for the cathode of an organic EL element include metals with low work functions such as aluminum, alloys with even lower work functions such as magnesium-silver alloys, magnesium-calcium alloys, magnesium-indium alloys, and aluminum-magnesium alloys, as well as conductive transparent materials such as ITO (indium tin oxide) and IZO (indium zinc oxide). Metals and alloys are formed to a thin thickness of about 10 to 200 nm to form a semitransparent cathode electrode.
  • the organic EL element of the present invention contains a phenanthroline compound represented by general formula (A) in the capping layer.
  • the capping layer may be composed of a single layer formed by solely forming a film of one phenanthroline compound selected from the group of compounds represented by general formula (A), or may be composed of a mixed layer formed by mixing two or more phenanthroline compounds selected from this group of compounds, or may be composed of a mixed layer formed by mixing a phenanthroline compound selected from this group of compounds with a material other than the phenanthroline compound represented by general formula (A).
  • the capping layer may have a single layer structure, a laminated structure formed by laminating layers formed by solely forming a film or layers formed by mixing and forming a film, or a laminated structure formed by laminating a layer formed by solely forming a film and a layer formed by mixing and forming a film. These materials can be formed into a thin film by known methods such as vapor deposition, spin coating, and inkjet.
  • the thickness of the capping layer is preferably in the range of 30 nm to 120 nm, and particularly preferably in the range of 40 nm to 80 nm.
  • the capping layer containing the phenanthroline compound represented by general formula (A) preferably has a refractive index for light with a wavelength of 450 nm to 700 nm of 1.70 or more, and particularly preferably 1.85 or more.
  • the organic EL element to which the present invention is applied is not limited to this, and may also be an organic EL element with a bottom emission structure or an organic EL element with a dual emission structure that emits light from both the top and bottom.
  • the above description of the organic EL element can be referred to.
  • the electrode in the direction in which light is extracted from the light-emitting element to the outside is transparent or semitransparent. That is, in a bottom emission structure, it is preferable that the electrode on the substrate side is transparent or semitransparent, and in a dual emission structure, it is preferable that the electrodes on both sides are transparent or semitransparent.
  • the electronic device and electronic element of the present invention have a pair of electrodes and at least one organic layer disposed between the pair of electrodes, and at least one of the organic layers contains a compound represented by general formula (I).
  • a compound represented by general formula (I) please refer to the description in the above column ⁇ Compound represented by general formula (I)>.
  • the electronic device include a display device or a light-emitting device equipped with an organic EL element, as well as an electrophotographic photoreceptor, an image sensor, a photoelectric conversion element, a solar cell, etc.
  • Examples of the display device include a display component such as an organic EL panel module, a television, a mobile phone, a tablet, a personal computer, etc.
  • the light-emitting device include lighting or a vehicle lamp, etc.
  • Example 5 The melting points and glass transition points (Tg) of the compounds obtained in Examples 1 to 4 were measured using a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS). The measurement results are shown in Table 1.
  • Example 6 Using the compounds obtained in Examples 1 to 4, a vapor-deposited film having a thickness of 80 nm was prepared on a silicon substrate, and the refractive index n and extinction coefficient k at wavelengths of 450 nm and 750 nm were measured using a spectrophotometer (F10-RT-UV, manufactured by Filmetrics). For comparison, measurements were also made on Alq3 and a comparative compound (CPL-1) having the following structural formula (see, for example, Patent Document 4). The measurement results are summarized in Table 2.
  • the phenanthroline compound of the present invention has a higher refractive index than Alq3 and the comparative compound (CPL-1) in the wavelength range of 450 nm to 750 nm. This result shows that the use of the phenanthroline compound of the present invention as a constituent material of the capping layer can be expected to improve the light extraction efficiency in an organic EL element.
  • Example 7 As shown in FIG. 1, a reflective ITO electrode was formed in advance as a transparent anode 2 on a glass substrate 1, and a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8, and a capping layer 9 were deposited in this order on the reflective ITO electrode as a transparent anode 2 to prepare an organic EL element.
  • a glass substrate 1 on which a 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film were successively formed was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 250°C for 10 minutes. After that, a UV ozone treatment was performed for 2 minutes, and then the glass substrate with ITO was attached to a vacuum deposition machine and the pressure was reduced to 0.001 Pa or less.
  • a compound (HTM-1) having the following structural formula was formed as a hole transport layer 4 to a thickness of 140 nm.
  • lithium fluoride was formed as an electron injection layer 7 to a thickness of 1 nm.
  • a magnesium silver alloy was formed as a cathode 8 to a thickness of 12 nm.
  • Example 3 the compound (30) of Example 1 was formed as a capping layer 9 to a thickness of 60 nm.
  • the characteristics of the fabricated organic EL element were measured in air at room temperature, and the measurement results of the light emission characteristics when a direct current voltage was applied are summarized in Table 3.
  • Example 8 to 10 Organic EL devices were prepared under the same conditions as in Example 7, except that the compounds obtained in Examples 2 to 4 were used as the capping layer 9 instead of the compound (30) in Example 1. The characteristics of the prepared organic EL devices were measured in the air at room temperature, and the measurement results of the luminescence characteristics when a direct current voltage was applied are summarized in Table 3.
  • Example 1 For comparison, an organic EL device was prepared under the same conditions as in Example 7, except that Alq3 was used as the capping layer 9 instead of the compound (30) in Example 1. The characteristics of the prepared organic EL device were measured in the air at room temperature, and the measurement results of the luminescence characteristics when a DC voltage was applied are summarized in Table 3.
  • Example 2 For comparison, an organic EL device was prepared under the same conditions as in Example 7, except that compound (CPL-1) was used instead of compound (30) in Example 1 as the capping layer 9. The characteristics of the prepared organic EL device were measured in the air at room temperature, and the measurement results of the luminescence characteristics when a direct current voltage was applied are summarized in Table 3.
  • the organic EL elements produced in the above Examples and Comparative Examples were used to measure the element characteristics and element lifetime, and the results are summarized in Table 3.
  • the element lifetime measured in the present invention was measured as the time it took for the initial luminance to decay to 95% when driven at a constant current of 10 mA/ cm2 .
  • the driving voltage at a current density of 10 mA/ cm2 was almost the same for the devices of Comparative Example 1 and Comparative Example 2 and the devices of Examples 7 to 10, whereas the devices of Examples showed significant improvements in luminance, luminous efficiency, power efficiency, and device life compared to the devices of Comparative Examples.
  • the phenanthroline compound represented by general formula (A) of the present invention is a material suitable for use in a capping layer, and that the light extraction efficiency of an organic EL device can be significantly improved by increasing the refractive index of the capping layer.
  • the phenanthroline compound of the present invention has a high refractive index, can significantly improve light extraction efficiency, and is stable in a thin film state, making it an excellent compound suitable for use in organic EL elements.
  • organic EL elements made using the phenanthroline compound of the present invention can achieve high efficiency.
  • using the compound of the present invention which has no absorption in the blue, green, and red wavelength regions, is particularly suitable for displaying clear, bright images with good color purity. For example, it is expected that the compound will be used in home appliances and lighting.

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