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WO2022250386A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2022250386A1
WO2022250386A1 PCT/KR2022/007243 KR2022007243W WO2022250386A1 WO 2022250386 A1 WO2022250386 A1 WO 2022250386A1 KR 2022007243 W KR2022007243 W KR 2022007243W WO 2022250386 A1 WO2022250386 A1 WO 2022250386A1
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group
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organic light
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허동욱
홍성길
한미연
이재탁
윤정민
윤희경
박호윤
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LG Chem Ltd
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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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present invention relates to an organic light emitting device.
  • the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • Patent Document 0002 US Patent Publication No. 2007-0196692
  • Patent Document 0003 Korean Patent Publication No. 10-2017-0048159
  • Patent Document 0004 US Patent Registration No. 6821643
  • the present invention relates to an organic light emitting device.
  • the present invention provides the following organic light emitting device.
  • an electron transport layer an electron injection layer, or an electron transport and injection layer
  • the hole blocking layer includes a compound represented by Formula 1 below,
  • the electron transport layer, the electron injection layer, or the electron transport and injection layer comprises a compound represented by Formula 2 or 3 below,
  • X 1 to X 3 are each independently N or CH, but at least one or more of X 1 to X 3 is N;
  • L 1 to L 3 are each independently a direct bond; or a substituted or unsubstituted C 6-60 arylene;
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl;
  • Ar 3 is a substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,
  • R 1 to R 4 are each independently hydrogen or deuterium
  • n1 to n4 are integers from 1 to 4;
  • L 4 and L 5 are each independently a direct bond; or a substituted or unsubstituted C 6-60 arylene;
  • Ar 4 and Ar 5 are each independently a substituent represented by Formula 4 below;
  • X 4 to X 8 are each independently N or C (R 5 ), but at least two or more of X 4 to X 8 are N;
  • R 5 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-20 Alkyl; Substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S, or two adjacent R 5 of them bond to form a benzene ring.
  • the organic light emitting device by controlling the compounds included in the light emitting layer and the electron transport layer, the organic light emitting device may improve efficiency, low driving voltage, and/or lifespan characteristics.
  • FIG. 1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, a hole blocking layer 4, an electron transport and injection layer 5, and a cathode 6.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 8, an electron blocking layer 9, a light emitting layer 3, a hole blocking layer 4, and an electron transport and injection layer.
  • substituted or unsubstituted means deuterium; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy groups; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing at least one of N, O, and S atoms, or substituted or unsub
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group is specifically a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. but not limited to
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but is not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted, etc.
  • it is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing at least one of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms.
  • the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, and an acridyl group.
  • pyridazine group pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia A zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
  • an aralkyl group, an aralkenyl group, an alkylaryl group, and an aryl group among arylamine groups are the same as the examples of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the above-mentioned alkyl group.
  • the description of the heterocyclic group described above may be applied to the heteroaryl of the heteroarylamine.
  • the alkenyl group among the aralkenyl groups is the same as the examples of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of the heterocyclic group described above may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is formed by combining two substituents.
  • the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.
  • the present invention is a positive electrode; hole transport layer; light emitting layer; an electron transport layer, an electron injection layer, or an electron transport and injection layer; and a cathode, wherein the light emitting layer includes the compound represented by Formula 1, and the electron transport layer, the electron injection layer, or the electron transport and injection layer is selected from among the compound represented by Formula 2 and the compound represented by Formula 3. It provides an organic light-emitting device including any one or more.
  • the organic light emitting device adjusts the compound included in the light emitting layer and the electron transport layer, the electron injection layer, or the electron transport and injection layer to improve efficiency, lower driving voltage and/or lifetime in the organic light emitting device. characteristics can be improved.
  • the cathode material a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer.
  • the cathode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function so as to easily inject electrons into the organic material layer.
  • Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the organic light emitting device may include a hole injection layer between the anode and the hole transport layer, if necessary.
  • the hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer A compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer used in the present invention is a layer that receives holes from an anode or a hole injection layer formed on the anode and transports the holes to the light emitting layer, and can transport holes from the anode or the hole injection layer to the light emitting layer as a hole transport material.
  • a material having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
  • the organic light emitting device may include an electron blocking layer between the hole transport layer and the light emitting layer, if necessary.
  • the electron blocking layer is formed on the hole transport layer, and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons to increase hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device.
  • the electron suppression layer includes an electron suppression material, and an example of such an electron suppression material may be an arylamine-based organic material, but is not limited thereto.
  • the light emitting material included in the light emitting layer is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material includes a condensed aromatic ring derivative or a compound containing a hetero ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc.
  • styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • the organic light emitting device includes a hole blocking layer between the light emitting layer, an electron transport layer, an electron injection layer, or an electron transport and injection layer, as necessary.
  • the hole blocking layer is in contact with the light emitting layer.
  • the hole blocking layer serves to improve the efficiency of the organic light emitting device by suppressing the transfer of holes injected from the anode to the cathode without recombination in the light emitting layer.
  • the compound represented by Formula 1 is used as a material constituting the hole blocking layer.
  • L 1 and L 2 are each independently a direct bond or phenylene;
  • L 3 is a direct key, phenylene, biphenyldiyl, or terphenyldiyl.
  • Ar 1 and Ar 2 are each independently phenyl, biphenylyl, or naphthyl.
  • Ar 3 is any one of substituents represented by Formulas 1-1 to 1-7 below:
  • R 6 and R 7 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-10 Alkyl; or a substituted or unsubstituted C 6-60 aryl; Z is each independently NR 9 , O, or S; R 8 and R 9 are each independently a substituted or unsubstituted C 6-60 aryl.
  • R 6 and R 7 are each independently hydrogen, deuterium, methyl, or substituted or unsubstituted phenyl; R 8 and R 9 are phenyl.
  • Ar 3 is any one selected from the group consisting of:
  • the present invention provides a method for preparing the compound represented by Formula 1, as shown in Reaction Scheme 1 below.
  • X 1 to X 3 , L 1 to L 3 , and Ar 1 to Ar 3 are as defined above, and Z is halogen, preferably bromo or chloro.
  • the manufacturing method may be more specific in Preparation Examples to be described later.
  • electron transport layer electron injection layer, or electron transport and injection layer
  • the organic light emitting device may include an electron transport layer, an electron injection layer, or an electron transport and injection layer between the light emitting layer and the cathode.
  • the electron transport layer is a layer that receives electrons from the cathode or an electron injection layer formed on the cathode, transports electrons to the light emitting layer, and suppresses the transfer of holes in the light emitting layer.
  • an electron transport material electrons are well injected from the cathode.
  • the present invention may include at least one of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, has an excellent electron injection effect from a cathode, a light emitting layer or a light emitting material, and has a hole of excitons generated in the light emitting layer.
  • the present invention may include at least one of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3.
  • the electron transport and injection layer is a layer that simultaneously transports and injects electrons, and may include the compound represented by Chemical Formula 2 or 3.
  • Formula 2 is represented by Formula 2-1 below;
  • Formula 3 is represented by Formula 3-1 below.
  • L 4 , L 5 , Ar 4 and Ar 5 are as defined above.
  • L 4 and L 5 are each independently a direct bond, phenylene, or biphenyldiyl.
  • Ar 4 and Ar 5 are each independently any one selected from the group consisting of:
  • R 5 is as defined above.
  • each R 5 is independently hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl, or two adjacent ones thereof R 5 is bonded to form a benzene ring;
  • the phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl are each independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.
  • Ar 4 and Ar 5 are each independently any one selected from the group consisting of:
  • the present invention provides a method for producing a compound represented by Formula 2 or 3, as shown in Schemes 2 to 5 below.
  • L 4 , L 5 , Ar 4 , Ar 5 , R 1 to R 4 , and n1 to n4 are as defined above, and Z is halogen, preferably bromo or chloro.
  • the electron transport layer may further include a metal complex compound.
  • the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.
  • the electron injection layer may further include a metal complex compound.
  • the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.
  • FIG. 1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, a hole blocking layer 4, an electron transport and injection layer 5 and a cathode 6 .
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 8, an electron blocking layer 9, a light emitting layer 3, a hole blocking layer 4, electron transport and
  • An example of an organic light emitting device composed of an injection layer 5 and a cathode 6 is shown.
  • the organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described components. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode And, after forming each of the above-mentioned layers thereon, it can be manufactured by depositing a material that can be used as a cathode thereon.
  • PVD physical vapor deposition
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material on a substrate and an anode material in the reverse order of the above configuration (WO 2003/012890).
  • the light emitting layer may be formed by a solution coating method as well as a vacuum deposition method of a host and a dopant.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • the organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.
  • B1-A (20 g, 43.1 mmol) and B1-B (10.3 g, 43.1 mmol) were added to 400 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (17.9 g, 129.2 mmol) was dissolved in 18 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 3 hours, cooling to room temperature, separating the organic layer and the water layer, and distilling the organic layer.
  • Compound B2 was prepared in the same manner as in Preparation Example 1-1, except for using each starting material as in the reaction scheme.
  • Compound B3 was prepared in the same manner as in Preparation Example 1-1, except for using each starting material as in the above reaction scheme.
  • Compound B4 was prepared in the same manner as in Preparation Example 1-1, except for using each starting material as in the above reaction scheme.
  • Compound B5 was prepared in the same manner as in Preparation Example 1-1, except for using each starting material as in the above reaction scheme.
  • Compound B6 was prepared in the same manner as in Preparation Example 1-1, except for using each starting material as in the above reaction scheme.
  • Compound B7 was prepared in the same manner as in Preparation Example 1-1, except for using each starting material as in the above reaction scheme.
  • B8-A (20 g, 43.1 mmol) and B8-B (15.4 g, 43.1 mmol) were added to 400 ml of xylene, stirred and refluxed. Thereafter, sodium tert-butoxide (12.4 g, 129.2 mmol) was added, and after stirring sufficiently, bis(tri tert-butylphosphine)palladium (0.7 g, 1.3 mmol) was added. After reacting for 1 hour, cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled.
  • E1-A (20 g, 64.1 mmol) and E1-B (55.8 g, 128.2 mmol) were added to tetrahydrofuran (400 ml), stirred and refluxed. Thereafter, potassium carbonate (26.6 g, 192.3 mmol) was dissolved in water (27 ml), and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (2.2 g, 1.9 mmol) was added. After reacting for 1 hour, cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • Compound E2 was prepared in the same manner as in Preparation Example 2-1, except for using each starting material as in the above reaction scheme.
  • Compound E4 was prepared in the same manner as in Preparation Example 2-1, except for using each starting material as in the above reaction scheme.
  • Compound E5 was prepared in the same manner as in Preparation Example 2-1, except for using each starting material as in the above reaction scheme.
  • E8-A (20 g, 47.6 mmol) and E8-B (28 g, 47.6 mmol) were added to 1,4-Dioxane (400 ml), stirred and refluxed. Thereafter, potassium triphosphate (30.3 g, 142.9 mmol) was dissolved in water (30 ml), added, stirred sufficiently, dibenzylideneacetone palladium (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.9 g). mmol) was added. After reacting for 5 hours, the resulting solid was filtered after cooling to room temperature.
  • Compound E9 was prepared in the same manner as in Preparation Examples 2-8, except for using each starting material as in the above reaction scheme.
  • Compound E10 was prepared in the same manner as in Preparation Examples 2-8, except for using each starting material as in the reaction scheme.
  • Compound E12 was prepared in the same manner as in Preparation Example 2-1, except for using each starting material as in the reaction scheme.
  • Compound E15 was prepared in the same manner as in Preparation Example 2-1, except for using each starting material as in the above reaction scheme.
  • Compound E16 was prepared in the same manner as in Preparation Examples 2-8, except for using each starting material as in the reaction scheme.
  • Compound E17 was prepared in the same manner as in Preparation Examples 2-8, except for using each starting material as in the above reaction scheme.
  • Compound E18 was prepared in the same manner as in Preparation Examples 2-8, except for using each starting material as in the above reaction scheme.
  • Compound E19 was prepared in the same manner as in Preparation Example 2-1, except for using each starting material as in the reaction scheme.
  • Compound E20 was prepared in the same manner as in Preparation Example 2-1, except for using each starting material as in the reaction scheme.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a Fischer Co. product was used as the detergent
  • distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water.
  • ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner.
  • solvents such as isopropyl alcohol, acetone, and methanol
  • a hole injection layer was formed by thermally vacuum depositing the following compound HI-A to a thickness of 600 ⁇ on the prepared ITO transparent electrode.
  • a hole transport layer was formed by sequentially vacuum depositing hexanitrile hexaazatriphenylene (HAT, 50 ⁇ ) and the compound HT-A (600 ⁇ ) of the following chemical formula on the hole injection layer.
  • the following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to a film thickness of 200 ⁇ on the hole transport layer to form a light emitting layer.
  • the compound B1 was thermally vacuum deposited on the light emitting layer to a thickness of 50 ⁇ to form a hole blocking layer.
  • the compound E1 and the following compound [LiQ] (Lithiumquinolate) were vacuum deposited in a weight ratio of 1:1 to form an electron transport and injection layer with a thickness of 300 ⁇ .
  • a negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron transport and injection layer.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride on the anode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum level during deposition was 1 ⁇ 10 Maintaining -7 to 5 ⁇ 10 -8 torr, an organic light emitting device was fabricated.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds of Table 1 were used instead of Compound B1 or Compound E1.
  • the compounds of ET-1 to ET-19 used in Table 1 are as follows.
  • the compound represented by Chemical Formula 1 of the present invention may be used in an organic material layer corresponding to a hole blocking layer of an organic light emitting device.
  • the compound represented by Chemical Formula 2 or Chemical Formula 3 of the present invention may be used in an organic material layer capable of simultaneously transporting and injecting electrons in an organic light emitting device.
  • the organic light emitting device including the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or 3 of the present invention is represented by Chemical Formula 2 , or 3, it was confirmed that the organic light emitting diode does not contain a heterocyclic compound, showing significantly better characteristics in terms of efficiency and lifespan.
  • substrate 2 anode
  • hole injection layer 8 hole transport layer

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique.
PCT/KR2022/007243 2021-05-25 2022-05-20 Dispositif électroluminescent organique Ceased WO2022250386A1 (fr)

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JP2012126718A (ja) * 2010-11-25 2012-07-05 Tosoh Corp ２，２’−置換ビフェニル誘導体とその製造方法、及びそれらを構成成分とする有機電界発光素子
KR20150055356A (ko) * 2013-11-13 2015-05-21 엘지디스플레이 주식회사 인광 호스트 화합물 및 이를 포함하는 유기전계발광소자
KR101884130B1 (ko) * 2017-08-29 2018-07-31 주식회사 두산 유기 전계 발광 소자
KR20200024725A (ko) * 2018-08-28 2020-03-09 주식회사 엘지화학 유기 발광 소자
KR20200024726A (ko) * 2018-08-28 2020-03-09 주식회사 엘지화학 유기 발광 소자

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KR100430549B1 (ko) 1999-01-27 2004-05-10 주식회사 엘지화학 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법
KR102208995B1 (ko) 2015-10-23 2021-01-28 삼성에스디아이 주식회사 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
EP3674299B1 (fr) * 2018-12-28 2021-11-24 cynora GmbH Molécules organiques pour dispositifs optoélectroniques

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JP2012126718A (ja) * 2010-11-25 2012-07-05 Tosoh Corp ２，２’−置換ビフェニル誘導体とその製造方法、及びそれらを構成成分とする有機電界発光素子
KR20150055356A (ko) * 2013-11-13 2015-05-21 엘지디스플레이 주식회사 인광 호스트 화합물 및 이를 포함하는 유기전계발광소자
KR101884130B1 (ko) * 2017-08-29 2018-07-31 주식회사 두산 유기 전계 발광 소자
KR20200024725A (ko) * 2018-08-28 2020-03-09 주식회사 엘지화학 유기 발광 소자
KR20200024726A (ko) * 2018-08-28 2020-03-09 주식회사 엘지화학 유기 발광 소자

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