WO2020096286A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2020096286A1
WO2020096286A1 PCT/KR2019/014717 KR2019014717W WO2020096286A1 WO 2020096286 A1 WO2020096286 A1 WO 2020096286A1 KR 2019014717 W KR2019014717 W KR 2019014717W WO 2020096286 A1 WO2020096286 A1 WO 2020096286A1
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group
compound
light emitting
organic light
emitting device
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Korean (ko)
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허동욱
홍성길
허정오
한미연
이재탁
양정훈
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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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • H10K50/165—Electron transporting 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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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
    • H10K85/649—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

Definitions

  • the present invention relates to an organic light emitting device.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • the organic light emitting device using the 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 have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic material layer is often formed of a multi-layered structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to an organic light emitting device.
  • the present invention provides the following organic light emitting device:
  • anode Emitting layer; An electron-regulating layer comprising a first compound; An electron transport layer comprising a second compound; And a cathode,
  • cETL LUMO is LUMO of the first compound
  • ETL LUMO is the LUMO of the second compound.
  • the above-described organic light-emitting device may improve the efficiency, low driving voltage, and / or lifespan characteristics in the organic light-emitting device by controlling the compounds included in the electron control layer and the electron transport layer.
  • 1 is an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron regulating layer 5, an electron transport layer 6, and a cathode 7 It is shown.
  • Figure 2 shows the results of measuring the HOMO level in the experimental example of the present invention.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more
  • 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 oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, 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 trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, 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 carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. 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 a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. 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, styrenyl group, styrenyl group, and the like, but are 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 cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number 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 combine with each other to form a spiro structure.
  • the fluorenyl group When the fluorenyl group is substituted, It can be back. However, it is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazo
  • an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group described above.
  • the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described example of the alkyl group.
  • heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group.
  • 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 two substituents are formed by bonding.
  • the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.
  • the positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth.
  • the positive electrode 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); A combination of metal and oxide 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 to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
  • the organic light emitting device may include a hole injection layer on the anode, if necessary.
  • the hole injection layer is a layer for injecting holes from the anode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is produced in the light emitting layer.
  • a compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferred. It is preferred that the high occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer.
  • HOMO high occupied molecular orbital
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
  • Organic anthraquinone and polyaniline and polythiophene-based conductive polymers are not limited thereto.
  • the organic light emitting device according to the present invention may include a hole transport layer, if necessary.
  • the hole transport layer used in the present invention is a layer that transports holes from the hole injection layer formed on the anode or the anode to the hole, and transports holes to the light emitting layer.
  • a material a material having high mobility for holes is suitable.
  • arylamine-based organic materials include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the light-emitting material included in the light-emitting layer is a material capable of emitting light in the visible light region by transporting 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.
  • the light emitting layer may include a host material and a dopant material.
  • the host material may be a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound.
  • a compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted.
  • a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like but are not limited thereto.
  • examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.
  • the organic light emitting device includes an electron control layer adjacent to the light emitting layer and an electron transport layer adjacent to the electron control layer.
  • the electron regulating layer serves to prevent holes injected from the anode from being recombined in the light emitting layer and to pass to the electron transport layer, and the electron transport layer serves to receive electrons from the cathode or electron injection layer and transport electrons to the light emitting layer. do.
  • the material constituting the electron-controlling layer and the material constituting the electron-transporting layer satisfy specific conditions, thereby improving efficiency in the organic light-emitting device, and improving low driving voltage and / or life characteristics.
  • the electron regulating layer comprising the first compound and the electron transporting layer containing the second compound satisfy Equations 1 and 2 below:
  • cETL LUMO is LUMO of the first compound
  • ETL LUMO is the LUMO of the second compound.
  • the cETL LUMO and ETL LUMO mean the absolute value of each LUMO.
  • the LUMO value of the first compound is 2.0 eV or more.
  • the LUMO value of the compound constituting the electron-regulating layer is in an appropriate range, and at the same time, the LUMO value of the compound constituting the electron-transporting layer is in the same range as in Equation 2, so that it is electronically controlled. It is possible to improve the performance of the organic light emitting device by effectively controlling the movement of electrons due to the difference in LUMO between the layer layer and the electron transport layer.
  • the (cETL LUMO -ETL LUMO ) value of Equation 2 is greater than -0.69 eV, greater than 0.68 eV, or greater than 0.67 eV, less than -0.1 eV, less than -0.2 eV, less than -0.3 eV, -0.4 less than eV, or less than -0.5 eV.
  • the first compound is a compound represented by Formula 1 below:
  • X One And X 2 are each independently NR One , O, or S, X One And X 2 At least one of the NR One ego,
  • R 1 is each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,
  • R 2 and R 3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.
  • R 1 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl.
  • R 2 and R 3 are hydrogen, dibenzofuranyl, or dibenzothiophenyl.
  • the compound represented by Formula 1 is any one selected from the group consisting of:
  • reaction is a Suzuki coupling reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the second compound is a compound represented by Formula 2 below:
  • X 3 are each independently N, or CH, and two or more of X 3 are N,
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl,
  • n 1 or 2
  • L is a direct bond; n + 1 monovalent substituted or unsubstituted C 6-60 aromatic ring; Or a C 2-60 heteroaromatic ring containing one or more of n + 1 monovalent substituted or unsubstituted O, N, Si and S, provided that when n is 2, L is not a direct bond,
  • Ar 3 is substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.
  • Ar 1 and Ar 2 are each independently phenyl or biphenylyl.
  • L is a single bond; Divalent benzene; Trivalent benzene; Or any one selected from the group consisting of:
  • Ar 3 is any one selected from the group consisting of:
  • the compound represented by Formula 2 is any one selected from the group consisting of:
  • reaction is a Suzuki coupling reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the electron injection layer when the electron injection layer is formed adjacent to the cathode, the electron injection layer may further include a metal complex compound or an organic compound.
  • the weight ratio of the second compound and the metal complex compound or organic compound is 1:99 to 99: 1, 10:90 to 90:10, 20:80 to 80:20, 30 : 70 to 70:30, or 40:60 to 60:40.
  • 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) (o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc. , But is not limited to this.
  • the organic light emitting device according to the present invention may include an electron injection layer, if necessary.
  • the electron injection layer is a layer that injects electrons from the cathode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • FIG. 1 is an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron regulating layer 5, an electron transport layer 6, and a cathode 7 It is shown.
  • the organic light emitting device can be manufactured by sequentially stacking the above-described configuration.
  • a positive electrode is formed by depositing metal or conductive metal oxides or alloys thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic material layer including a hole transport layer, a light emitting layer, an electron control layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the light emitting layer may be formed by a host and a dopant by a vacuum deposition method as well as a solution application method.
  • the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type or a double-sided emission type depending on the material used.
  • the cET-1-sm1 compound (10 g, 25.1 mmol) and the cET-1-sm2 compound (9.3 g, 25.1 mmol) were completely dissolved in THF (100 mL), followed by potassium carbonate (10.4 g, 75.3 mmol). It was dissolved in water (40 mL) and added. After adding tetrakis (triphenylphosphine) palladium (0) (0.87 g, 0.753 mmol), the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed to filter the white solid. The filtered white solid was washed twice each with THF and ethyl acetate to prepare the cET-1 compound (10.6 g, yield 75%).
  • the cET-2 compound was prepared in the same manner as in Preparation Example 1, except that each starting material was in the same manner as in the above scheme.
  • the ET-1 compound was prepared in the same manner as in Preparation Example 1-1, except that each starting material was as in the above reaction scheme.
  • the ET-2 compound was prepared in the same manner as in Preparation Example 1-1, except that each starting material was as in the above reaction scheme.
  • Each starting material is the same as the reaction scheme, and the same method as in Production Example 1-1, except that the equivalent amount of the ET-3-sm2 compound is twice the equivalent of the ET-3-sm1 compound.
  • a compound represented by Chemical Formula ET-3 was prepared.
  • the ET-4 compound was prepared by the same method as the production method of Preparation Example 1-1, except that each starting material was as in the above reaction scheme.
  • the HOMO level was measured using an atmospheric photoelectron spectroscopy device (manufactured by RIKEN KEIKI Co., Ltd .: AC3) (FIG. 2), and the LUMO level was calculated as a wavelength value measured through photoluminescence (PL). Did.
  • the measured results are shown in Table 1 below.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • Fischer Co. product was used as the detergent
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum-deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • the following HAT compound was sequentially vacuum deposited to a thickness of 50, and the following HT-A compound to a thickness of 60 ⁇ to form a hole transport layer.
  • the following BH compound and the following BD compound were vacuum deposited to a thickness of 200 Pa in a weight ratio of 25: 1 to form a light emitting layer.
  • the compound cET-1 prepared above was vacuum-deposited to a thickness of 50 ⁇ on the light emitting layer to form an electronic control layer.
  • the electron transport layer was formed by vacuum-depositing the compound ET-1 prepared above and the following LiQ compound on a thickness of 300 ⁇ in a weight ratio of 1: 1 on the electron control layer.
  • Lithium fluoride (LiF) was sequentially deposited on the electron transport layer to a thickness of 10, and aluminum to a thickness of 1000 ⁇ to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ / sec
  • the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 ⁇ / sec and aluminum at 2 2 / sec
  • the vacuum degree during deposition was 1 ⁇ 10.
  • An organic light-emitting device was manufactured by maintaining -7 to 5 x 10 -5 torr.
  • Example 2-1 an organic light emitting device was manufactured according to the same method as Example 2-1 except for using the compound of Table 2 below instead of the compounds cET-1 and / or ET-1.
  • Example 2-1 an organic light emitting device was manufactured according to the same method as Example 2-1 except for using the compound of Table 2 below instead of the compounds cET-1 and / or ET-1.
  • Table 2 the compound ET-A is as follows.
  • the driving voltage and luminous efficiency were measured at the current density of 10 mA / cm 2 for the organic light-emitting device manufactured in the above Examples and Comparative Examples, and the time to be 90% compared to the initial luminance at the current density of 20 mA / cm 2 ( T90). The results are shown in Table 2 below.
  • substrate 2 anode
  • hole transport layer 4 light emitting layer

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Abstract

Dans un dispositif électroluminescent organique selon la présente invention, en ajustant des composés inclus dans une couche de commande d'électrons et une couche de transport d'électrons, l'efficacité, la faible tension de commande et/ou les caractéristiques de durée de vie du dispositif électroluminescent organique peuvent être améliorées.
PCT/KR2019/014717 2018-11-09 2019-11-01 Dispositif électroluminescent organique Ceased WO2020096286A1 (fr)

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