WO2023085835A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2023085835A1
WO2023085835A1 PCT/KR2022/017711 KR2022017711W WO2023085835A1 WO 2023085835 A1 WO2023085835 A1 WO 2023085835A1 KR 2022017711 W KR2022017711 W KR 2022017711W WO 2023085835 A1 WO2023085835 A1 WO 2023085835A1
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compound
water
organic layer
stirred
added
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김민준
이동훈
서상덕
김영석
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주식회사 엘지화학
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Priority claimed from KR1020220149170A external-priority patent/KR20230069848A/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202280031945.2A priority Critical patent/CN117222651A/zh
Publication of WO2023085835A1 publication Critical patent/WO2023085835A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass

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  • the present invention relates to a novel compound and an organic light emitting device including the same.
  • 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
  • the present invention relates to a novel compound and an organic light emitting device including the same.
  • the present invention provides a compound represented by Formula 1 below:
  • One of X 1 to X 10 is N, the other is C substituted with a substituent represented by Formula 2 below, and the others are CR 1 ;
  • R 1 is each independently hydrogen or deuterium
  • Y is each independently N or CR 2 , provided that at least one of Y is N;
  • R 2 are each independently hydrogen or deuterium
  • L is a single bond or a substituted or unsubstituted C 6-60 arylene
  • L 1 and L 2 are each independently a single 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, or a substituted or unsubstituted C 2-60 heteroaryl containing at least one selected from the group consisting of N, O and S; ego,
  • 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 of the organic material layers includes the compound represented by Chemical Formula 1. do.
  • the compound represented by Chemical Formula 1 may be used as a material for an organic layer of an organic light emitting diode, and may improve efficiency, low driving voltage, and/or lifespan characteristics of an organic light emitting diode.
  • the compound represented by Chemical Formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
  • FIG. 1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer ( 9) and an example of an organic light emitting element composed of a cathode 4 is shown.
  • 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 group; 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 substituent 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. Specifically, it may be a substituent 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 substituent 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
  • 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.
  • one or more hydrogens may be substituted with deuterium.
  • Y is all N.
  • Formula 1 is represented by any one of Formulas 1-1 to 1-10 below:
  • one of X 2 to X 10 is C substituted with a substituent of Formula 2, and the others are each independently CH or CD,
  • one of X 1 and X 3 to X 10 is C substituted with a substituent of Formula 2, and the others are each independently CH or CD,
  • one of X 1 , X 2 and X 4 to X 10 is C substituted with a substituent of Formula 2, and the others are each independently CH or CD,
  • one of X 1 to X 3 and X 5 to X 10 is C substituted with a substituent of Formula 2, and the others are each independently CH or CD,
  • one of X 1 to X 4 and X 7 to X 10 is C substituted with a substituent of Formula 2, the others are each independently CH or CD, X 6 is CH or CD,
  • one of X 1 to X 4 and X 7 to X 10 is C substituted with a substituent of Formula 2, the others are each independently CH or CD, X 5 is CH or CD,
  • one of X 1 to X 6 is C substituted with a substituent of Formula 2, the others are each independently CH or CD, and X 8 to X 10 are each independently CH or CD,
  • one of X 1 to X 6 is C substituted with a substituent of Formula 2, the others are each independently CH or CD, and X 7 , X 9 and X 10 are each independently CH or is a CD,
  • one of X 1 to X 6 is C substituted with a substituent of Formula 2, the others are each independently CH or CD, and X 7 , X 8 and X 10 are each independently CH or is a CD,
  • one of X 1 to X 6 is C substituted with a substituent of Formula 2, the others are each independently CH or CD, and X 7 to X 9 are each independently CH or CD.
  • L is a single bond, unsubstituted or substituted with one or more deuterium phenylene, or unsubstituted or substituted with one or more deuterium naphthylene. More preferably, L is a single bond, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,4-naphthylene, 1,3-naphthylene, 1,5-naphthylene ethylene, or 1,6-naphthylene, where L may be substituted with at least one deuterium.
  • L 1 and L 2 are each independently a single bond, unsubstituted or substituted with one or more deuterium phenylene, or unsubstituted or one or more deuterium substituted naphthylene. More preferably, L 1 and L 2 are each independently a single bond, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,4-naphthylene, 1,3-naphthylene ethylene, 1,5-naphthylene, or 1,6-naphthylene, wherein L may be substituted with at least one deuterium.
  • Ar 1 and Ar 2 are each independently selected from phenyl, biphenylyl, terphenylyl, naphthyl, (phenyl)naphthyl, (naphthyl)phenyl, phenanthrenyl, benzophenanthrenyl, dibenzofuran Ranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-carbazolyl, wherein Ar 1 and Ar 2 are each independently unsubstituted or substituted with at least one deuterium.
  • the benzophenanthrenyl includes benzo[a]phenanthrenyl, benzo[b]phenanthrenyl, or benzo[c]phenanthrenyl.
  • the reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the reaction can be changed as known in the art.
  • the manufacturing method may be more specific in Preparation Examples to be described later.
  • the present invention provides an organic light emitting device including the compound represented by Formula 1 above.
  • the present invention provides 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 of the organic material layers includes the compound represented by Chemical Formula 1. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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, and the like as organic layers.
  • the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.
  • the organic layer may include a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1.
  • the compound according to the present invention can be used as a dopant of the light emitting layer.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes the compound represented by Chemical Formula 1.
  • the electron transport layer, the electron injection layer, or the layer simultaneously transporting and injecting electrons includes the compound represented by Formula 1.
  • the organic material layer may include a light emitting layer and an electron transport layer
  • the electron transport layer may include the compound represented by Chemical Formula 1.
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • 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.
  • FIGS. 1 and 2 the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .
  • Chemical Formula 1 shows an example of an organic light emitting device composed of 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.
  • the compound represented by Formula 1 may be included in at least one layer of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
  • the organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Chemical Formula 1. Also, 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. 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 After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and depositing a material that can be used as a cathode thereon, it can be prepared. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • PVD physical vapor deposition
  • the compound represented by Chemical Formula 1 may be formed as 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 coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
  • 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 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. It is preferable that 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.
  • HOMO highest occupied molecular orbital
  • 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 is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • a hole transport material a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is a material having high hole mobility. This 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 light emitting material 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, respectively, 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 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 Al complexes 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 having a low work function followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by a layer of aluminum or silver.
  • the electron injection layer is a layer for injecting electrons from an electrode, has the ability to transport electrons, has an excellent electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer.
  • a compound that prevents migration to a layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, metals 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-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side 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 an organic light emitting device.
  • 3-bromopyridin-4-amine (15g, 86.7mmol) and (6-chloro-2-methoxynaphthalen-1-yl)boronic acid (21.3g, 91mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (35.9g, 260.1mmol) was dissolved in 100ml of water, and after sufficiently stirred, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.9mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated and the organic layer was distilled.
  • 4-bromopyridin-3-amine (15g, 86.7mmol) and (7-chloro-2-methoxynaphthalen-1-yl)boronic acid (21.3g, 91mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (35.9g, 260.1mmol) was dissolved in 100ml of water, and after sufficiently stirred, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.9mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated and the organic layer was distilled.
  • Compound A-2-7_P2 (15g, 59.1mmol) and bis(pinacolato)diboron (16.5g, 65mmol) were stirred while refluxing in 300ml of 1,4-dioxane. After that, potassium acetate (8.7g, 88.7mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (1g, 1.8mmol) and tricyclohexylphosphine (1g, 3.5mmol) were added. After reacting for 9 hours, cooling to room temperature and separating the organic layer using chloroform and water, the organic layer was distilled.
  • 3-bromo-5-chloropyridin-2-amine (15g, 73.7mmol) and (2-methoxynaphthalen-1-yl)boronic acid (15.6g, 77.4mmol) were added to 300ml of THF and stirred and refluxed. After that, potassium carbonate (30.6g, 221.2mmol) was dissolved in 100ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.7mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer.
  • 3-bromopyridin-2-amine (15g, 86.7mmol) and (5-chloro-2-methoxynaphthalen-1-yl)boronic acid (21.5g, 91mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (35.9g, 260.1mmol) was dissolved in 100ml of water, and after sufficiently stirred, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.9mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated and the organic layer was distilled.
  • 2-bromo-4-chloropyridin-3-amine (15g, 73.7mmol) and (2-methoxynaphthalen-1-yl)boronic acid (15.6g, 77.4mmol) were added to 300ml of THF and stirred and refluxed. After that, potassium carbonate (30.6g, 221.2mmol) was dissolved in 100ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.7mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated and the organic layer was distilled.
  • 2-bromo-6-chloroaniline (15g, 72.6mmol) and (3-methoxyisoquinolin-4-yl)boronic acid (15.5g, 76.3mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (30.1g, 217.9mmol) was dissolved in 100ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.7mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer.
  • 2-bromoaniline (15g, 87.2mmol) and (7-chloro-3-methoxyquinolin-4-yl)boronic acid (21.7g, 91.5mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (36.2g, 261.6mmol) was dissolved in 100ml of water, and after sufficiently stirred, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.9mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer.
  • 2-bromoaniline (15g, 87.2mmol) and (7-chloro-6-methoxyquinolin-5-yl)boronic acid (21.7g, 91.5mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (36.2g, 261.6mmol) was dissolved in 100ml of water, and after sufficiently stirred, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.9mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer.
  • Compound A-7-4_P2 (15g, 59.1mmol) and bis(pinacolato)diboron (16.5g, 65mmol) were stirred while refluxing in 300ml of 1,4-dioxane. After that, potassium acetate (8.7g, 88.7mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (1g, 1.8mmol) and tricyclohexylphosphine (1g, 3.5mmol) were added. After reacting for 8 hours, cooling to room temperature and separating the organic layer using chloroform and water, the organic layer was distilled.
  • 2-bromo-5-chloroaniline (15g, 72.6mmol) and (6-methoxyisoquinolin-5-yl)boronic acid (15.5g, 76.3mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (30.1g, 217.9mmol) was dissolved in 100ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.7mmol) was added. After reacting for 2 hours, it was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled.
  • Compound A-8-2_P2 (15g, 59.1mmol) and bis(pinacolato)diboron (16.5g, 65mmol) were stirred while refluxing in 300ml of 1,4-dioxane. After that, potassium acetate (8.7g, 88.7mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (1g, 1.8mmol) and tricyclohexylphosphine (1g, 3.5mmol) were added. After reacting for 6 hours, cooling to room temperature and separating the organic layer using chloroform and water, the organic layer was distilled.
  • 2-bromo-4-chloroaniline (15g, 72.6mmol) and (7-methoxyisoquinolin-8-yl)boronic acid (15.5g, 76.3mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (30.1g, 217.9mmol) was dissolved in 100ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.7mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer.
  • 2-bromoaniline (15g, 87.2mmol) and (5-chloro-7-methoxyquinolin-8-yl)boronic acid (21.7g, 91.5mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (36.2g, 261.6mmol) was dissolved in 100ml of water, and after sufficiently stirred, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.9mmol) was added. After reacting for 4 hours, it was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled.
  • a glass substrate coated with indium tin oxide (ITO) with 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 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
  • the following compound HI-1 was formed to a thickness of 1150 ⁇ as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited to form a hole transport layer having a film thickness of 800 ⁇ .
  • an electron blocking layer was formed on the hole transport layer by vacuum depositing the following EB-1 compound to a film thickness of 150 ⁇ .
  • Compound 1 as a host and Compound Dp-7 as a dopant were vacuum deposited at a weight ratio of 98:2 to form a red light emitting layer having a thickness of 400 ⁇ .
  • a hole blocking layer was formed on the light emitting layer by vacuum depositing the following HB-1 compound to a film thickness of 30 ⁇ . Subsequently, the following ET-1 compound and the following LiQ compound were vacuum deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • a negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
  • the deposition rate of lithium fluoride on the cathode was 0.3 ⁇ / sec
  • the deposition rate of aluminum was 2 ⁇ / sec
  • the vacuum level during deposition was 2x10 -7 ⁇ Maintaining 5x10 -6 torr, an organic light emitting device was manufactured.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except for using the compounds listed in Table 1 below in Example 1.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except for using the compounds listed in Table 1 below in Example 1.
  • Compounds B-1 to B-12 in Table 1 are as follows.
  • the lifetime T95 means the time required for the luminance to decrease from the initial luminance (6,000 nit) to 95%.
  • the red organic light emitting device of Example 1 used materials widely used in the prior art, and had a structure using compound [EB-1] as an electron blocking layer and Dp-7 as a red dopant.
  • the driving voltage decreased and the efficiency and lifespan increased compared to the comparative examples in Table 2. It was found that the energy transfer to the red dopant in the light emitting layer was well achieved. It can be determined that this is because electrons and holes combine to form excitons through a more stable balance in the light emitting layer compared to the comparative compound.
  • the driving voltage, luminous efficiency and lifetime characteristics of the organic light emitting device can be improved when the compound of the present invention is used as a host of the red light emitting layer.
  • substrate 2 anode

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique l'utilisant.
PCT/KR2022/017711 2021-11-12 2022-11-11 Nouveau composé et dispositif électroluminescent organique l'utilisant WO2023085835A1 (fr)

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KR10-2021-0155691 2021-11-12
KR20210155691 2021-11-12
KR1020220149170A KR20230069848A (ko) 2021-11-12 2022-11-10 신규한 화합물 및 이를 이용한 유기 발광 소자
KR10-2022-0149170 2022-11-10

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015199489A2 (fr) * 2014-06-27 2015-12-30 희성소재(주) Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
KR20160018458A (ko) * 2013-06-11 2016-02-17 이데미쓰 고산 가부시키가이샤 유기 전계발광소자용 재료, 이것을 이용한 유기 전계발광소자 및 전자 기기
CN107936031A (zh) * 2017-12-04 2018-04-20 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和有机发光器件
KR20200092633A (ko) * 2019-01-25 2020-08-04 엘티소재주식회사 화합물, 유기 광전자 소자 및 표시 장치
KR20210011164A (ko) * 2019-07-22 2021-02-01 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160018458A (ko) * 2013-06-11 2016-02-17 이데미쓰 고산 가부시키가이샤 유기 전계발광소자용 재료, 이것을 이용한 유기 전계발광소자 및 전자 기기
WO2015199489A2 (fr) * 2014-06-27 2015-12-30 희성소재(주) Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
CN107936031A (zh) * 2017-12-04 2018-04-20 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和有机发光器件
KR20200092633A (ko) * 2019-01-25 2020-08-04 엘티소재주식회사 화합물, 유기 광전자 소자 및 표시 장치
KR20210011164A (ko) * 2019-07-22 2021-02-01 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

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