WO2020149656A1 - Nouveau composé et diode électroluminescente organique l'utilisant - Google Patents

Nouveau composé et diode électroluminescente organique l'utilisant Download PDF

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WO2020149656A1
WO2020149656A1 PCT/KR2020/000781 KR2020000781W WO2020149656A1 WO 2020149656 A1 WO2020149656 A1 WO 2020149656A1 KR 2020000781 W KR2020000781 W KR 2020000781W WO 2020149656 A1 WO2020149656 A1 WO 2020149656A1
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group
light emitting
layer
formula
compound
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Korean (ko)
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서상덕
최지영
김주호
이동훈
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주식회사 엘지화학
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Priority claimed from KR1020200005489A external-priority patent/KR102354501B1/ko
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Priority to CN202080005477.2A priority Critical patent/CN112789275B/zh
Publication of WO2020149656A1 publication Critical patent/WO2020149656A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • 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 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-layer structure composed of different materials, for example, may be formed of 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 0001 Korean Patent Publication No. 10-2013-073537
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by Formula 1:
  • X is O or S
  • Y 1 , Y 2 and Y 3 are each independently CH; Or N, provided that at least two of Y 1 , Y 2 and Y 3 are N,
  • Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,
  • the two * are 1 and 2, respectively; 2 and 3; Or 3 and 4,
  • R 1 is hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Or substituted or unsubstituted C 6-60 aryl,
  • R 2 is substituted or unsubstituted C 6-60 aryl
  • n is an integer from 0 to 6
  • n is an integer from 1 to 8.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer provides an organic light emitting device comprising the compound of the present invention described above.
  • the compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or life characteristics in the organic light emitting device.
  • the compound represented by Chemical Formula 1 may be used as a light emitting layer material.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 It is done.
  • substituted or unsubstituted in this specification is 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; An 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 substituents
  • 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-butyldimethyl 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, steelbenyl 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 example of the aryl group described above.
  • the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described alkyl group.
  • heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group among the alkenyl groups 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 a 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 compound represented by Formula 1 may be any one selected from compounds represented by Formulas 2 to 7 below:
  • X, Y 1 , Y 2 , Y 3 , Ar 1 , Ar 2 , R 1 , R 2 , n and m are as defined above.
  • Ar 1 and Ar 2 are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Dibenzofuranyl or dibenzothiophenyl.
  • Ar 1 and Ar 2 are each independently phenyl; Biphenylyl; Or dibenzofuranyl.
  • R 1 is hydrogen; Or deuterium.
  • R 2 is phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Or dimethylfluorenyl.
  • n 1 or 2.
  • the compound represented by the formula (1) according to the present invention has a structure in which the electron acceptor unit nitrogen-containing heterocycle centered around dibenzofuran or dibenzothiophene and the carbazole group, the electron donor unit, are bonded to the ortho position. Interaction with each other face-to-face generates an intra-charge transfer (ICT) state, resulting in a smaller bandgap and light emission at longer wavelengths, resulting in easy energy transfer to the dopant of the yellow-green light-emitting device.
  • ICT intra-charge transfer
  • the aryl group substituted with carbazole increases the electron donation ability of carbazole to help the ICT to be generated more effectively, and at the same time compensates for the glass transition temperature drop that may occur due to the ortho position, thereby showing high stability of the device even after heat treatment, high efficiency, It may have a low driving voltage, high luminance, and long life.
  • the compound represented by Chemical Formula 1 may be prepared by a manufacturing method according to Reaction Scheme 1 below.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • X 1 , X 2 and X 3 are each independently halogen, preferably bromo or chloro, and the description of the remaining substituents is as defined above.
  • the first and second reactions are preferably performed in the presence of a palladium catalyst and a base as a Suzuki coupling reaction.
  • the third reaction is an amination reaction.
  • Reactants and catalysts for the 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 present invention provides an organic light emitting device comprising the compound represented by the formula (1).
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and an organic light emitting device is provided. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer.
  • the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.
  • the organic material layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport may be represented by Formula 1 It includes the compound displayed.
  • the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.
  • the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron injection and electron transport includes the compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or higher, high triplet energy (ET), and hole stability.
  • an n-type dopant used in the art may be mixed and used.
  • the organic material layer includes a light emitting layer and an electron transport layer
  • the electron transport layer may include a compound represented by Chemical Formula 1.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Chemical Formula 1 may be included in the light emitting layer.
  • FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done.
  • the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
  • the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer, and preferably, the light emitting layer may further include a compound represented by Chemical Formula 8:
  • Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • R 3 and R 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • a and b are each independently an integer from 0 to 7.
  • Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.
  • R 3 and R 4 are hydrogen.
  • the compound represented by Formula 8 is any one specifically selected from the group consisting of:
  • the organic light emitting device by using a combination of the compound represented by the formula (1) and the compound represented by the formula (8) in the light emitting layer, these synergistic effects can significantly improve the characteristics of low voltage, high efficiency, long life.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. Further, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy 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 injection layer, a hole transport layer, a light emitting 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 compound represented by Chemical Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • 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 first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • 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 an 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;
  • a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer.
  • a compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the highest 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 material layer.
  • HOMO highest occupied molecular orbital
  • the 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.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples 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 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.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • 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.
  • metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on 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 and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • Examples of 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-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • 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 compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • ITO Indium Tin Oxide
  • distilled water filtered secondarily by a filter of Millipore Co.
  • ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • HAT-CN hexanitrile hexaazatriphenylene
  • ET-A was thermally vacuum-deposited to a thickness of 200 MPa as an electron transport layer, and then ET-B and lithium were vacuum-deposited to a thickness of 100 MPa at a weight ratio of 98:2.
  • magnesium and silver were sequentially deposited at a thickness of 220 ⁇ at a ratio of 10:1, and aluminum was deposited at a thickness of 1000 ⁇ to form a cathode, thereby manufacturing an organic light emitting device.
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.7 ⁇ /sec, and the deposition rate of silver and magnesium was maintained at 2 ⁇ /sec, and the vacuum degree during deposition was 2 ⁇ 10 -7 ⁇ 5 ⁇ 10 -6 torr. By maintaining the, an organic light emitting device was produced.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 below was used instead of Compound 1.
  • the organic light emitting device manufactured in the above Experimental Example and Comparative Experimental Example was stored in a 110° C. oven for 30 minutes and heat treated, and then applied with a current to measure voltage, efficiency, and lifetime (T95) and the results are shown in Table 1 below. . At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 50 mA/cm 2 .
  • the compound represented by Chemical Formula 1 has a structure in which a nitrogen-containing hetero ring, which is an electron acceptor unit, and a carbazole group, which is an electron donor unit, are bonded to an ortho position centering on dibenzofuran or dibenzothiophene.
  • the electron donor unit and the electron acceptor unit are combined with an ortho, the two substituents face each other and interact with each other to generate an intra-charge transfer (ICT) state.
  • ICT intra-charge transfer
  • the dopant of the light emitting device is advantageous for energy transfer.
  • the aryl group substituted with carbazole increases the electron donating ability of carbazole to make ICT more prominent, and at the same time, compensates for the glass transition temperature drop that may occur due to the ortho position, thereby showing high stability of the device even after heat treatment. It can be seen through comparison with the example and the comparative example 3.
  • substrate 2 anode

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

Abstract

La présente invention concerne un nouveau composé et une diode électroluminescente organique l'utilisant.
PCT/KR2020/000781 2019-01-18 2020-01-16 Nouveau composé et diode électroluminescente organique l'utilisant WO2020149656A1 (fr)

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CN202080005477.2A CN112789275B (zh) 2019-01-18 2020-01-16 新型化合物及包含其的有机发光器件

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KR20190007096 2019-01-18
KR10-2019-0007096 2019-01-18
KR10-2020-0005489 2020-01-15
KR1020200005489A KR102354501B1 (ko) 2019-01-18 2020-01-15 신규한 화합물 및 이를 이용한 유기발광 소자

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4335846A1 (fr) 2022-06-30 2024-03-13 Beijing Summer Sprout Technology Co., Ltd. Matériau électroluminescent organique et dispositif associé

Citations (5)

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KR20150134248A (ko) * 2014-05-21 2015-12-01 삼성전자주식회사 카바졸계 화합물 및 이를 포함한 유기 발광 소자
KR20170102000A (ko) * 2015-02-13 2017-09-06 코니카 미놀타 가부시키가이샤 방향족 복소환 유도체, 그것을 사용한 유기 일렉트로루미네센스 소자, 조명 장치 및 표시 장치
KR20180068869A (ko) * 2016-12-14 2018-06-22 주식회사 엘지화학 유기 발광 소자
KR20180071621A (ko) * 2016-12-20 2018-06-28 희성소재 (주) 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
KR20180096444A (ko) * 2017-02-21 2018-08-29 희성소재 (주) 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150134248A (ko) * 2014-05-21 2015-12-01 삼성전자주식회사 카바졸계 화합물 및 이를 포함한 유기 발광 소자
KR20170102000A (ko) * 2015-02-13 2017-09-06 코니카 미놀타 가부시키가이샤 방향족 복소환 유도체, 그것을 사용한 유기 일렉트로루미네센스 소자, 조명 장치 및 표시 장치
KR20180068869A (ko) * 2016-12-14 2018-06-22 주식회사 엘지화학 유기 발광 소자
KR20180071621A (ko) * 2016-12-20 2018-06-28 희성소재 (주) 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
KR20180096444A (ko) * 2017-02-21 2018-08-29 희성소재 (주) 유기 발광 소자

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4335846A1 (fr) 2022-06-30 2024-03-13 Beijing Summer Sprout Technology Co., Ltd. Matériau électroluminescent organique et dispositif associé

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