WO2023096459A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2023096459A1
WO2023096459A1 PCT/KR2022/019072 KR2022019072W WO2023096459A1 WO 2023096459 A1 WO2023096459 A1 WO 2023096459A1 KR 2022019072 W KR2022019072 W KR 2022019072W WO 2023096459 A1 WO2023096459 A1 WO 2023096459A1
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김영석
김민준
이동훈
서상덕
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주식회사 엘지화학
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Definitions

  • 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.
  • the present invention provides a novel organic light emitting device material that can be used in an organic light emitting device and can be used in a solution process at the same time.
  • 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 4 is CR, and the others are each independently N or CR';
  • R is a substituent represented by Formula 2 below,
  • X 5 to X 10 are each independently N or CR';
  • one of X 1 to X 10 is N,
  • R' are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • L 1 is a direct bond; Substituted or unsubstituted C 6-60 arylene; Or a C 2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • L 2 is a direct bond; Substituted or unsubstituted C 6-60 arylene; Or a C 2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • L 3 is a direct bond; Substituted or unsubstituted C 6-60 arylene; Or a C 2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • Ar 1 is a substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • Ar 2 is a substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
  • the present invention is a first electrode; a second electrode provided to face the first electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes the compound represented by Chemical Formula 1.
  • the organic material layer including the compound may be a light emitting layer.
  • the compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device.
  • the compound represented by Chemical Formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, electron suppression, 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 is an example of an organic light emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron injection and transport layer (8) and a cathode (4). is shown.
  • substituted or unsubstituted means deuterium; halogen group; cyano 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 heteroaryl containing at least one of N, O, and S atoms, or substituted or unsubstituted
  • 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 or may be interpreted as a substituent in which two phenyl groups are connected.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group is specifically a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. but not limited to
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but is not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., 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.
  • heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms.
  • the heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group, indole group, carbazo
  • an aralkyl group, an aralkenyl group, an alkylaryl group, an arylamine group, and an aryl group among arylsilyl 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 above-described heteroaryl may be applied to the heteroaryl among heteroarylamines.
  • 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 heteroaryl 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 heteroaryl may be applied, except that it is formed by combining two substituents.
  • the present invention provides a compound represented by Formula 1 above.
  • One of X 1 to X 4 is CR, and the others are each independently N or CR', wherein R is a substituent represented by Formula 2 below, X 5 to X 10 are each independently N or CR', and , provided that one of X 1 to X 10 is N.
  • one of X 1 to X 4 is CR, the other is N, the others are each independently CR', and X 5 to X 10 are each independently CR';
  • one of X 1 to X 4 is CR, the others are each independently CR', one of X 5 to X 10 is N, and the others are each independently CR'.
  • R' are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S.
  • R' are all hydrogen; All may be deuterium.
  • L 1 is a direct bond; Substituted or unsubstituted C 6-60 arylene; Or a C 2-60 heteroarylene containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S.
  • L 1 is a direct bond; or phenylene.
  • L 1 is phenylene, it may be unsubstituted or substituted with one or more deuterium atoms.
  • L 2 is a direct bond; Substituted or unsubstituted C 6-60 arylene; Or a C 2-60 heteroarylene containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S.
  • L 2 is a direct bond; phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene.
  • L 2 is phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene, they may be unsubstituted or substituted with one or more deuterium atoms.
  • L 3 is a direct bond; Substituted or unsubstituted C 6-60 arylene; Or a C 2-60 heteroarylene containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S.
  • L 3 is a direct bond; phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene.
  • L 3 is phenylene; naphthylene; biphenylylene; 9,9-dimethyl-fluorenylene; or 9,9-diphenyl-fluorenylene, they may be unsubstituted or substituted with one or more deuterium atoms.
  • Ar 1 is a substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
  • Ar 1 is phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; 9,9-dimethyl-fluorenyl; 9,9-diphenyl-fluorenyl; dibenzofuranyl; dibenzothiophenyl; 9-phenyl-carbazolyl; or 9,9'-spirobi[9H-fluorene]yl.
  • Ar 1 may be unsubstituted or substituted with one or more deuterium atoms.
  • Ar 2 is a substituted or unsubstituted C 6-60 aryl; Or a C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
  • Ar 2 is phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; 9,9-dimethyl-fluorenyl; 9,9-diphenyl-fluorenyl; dibenzofuranyl; dibenzothiophenyl; 9-phenyl-carbazolyl; or 9,9'-spirobi[9H-fluorene]yl.
  • Ar 2 may be unsubstituted or substituted with one or more deuterium.
  • the compound is represented by any one of Formulas 1-1 to 1-4,
  • One of X 2 to X 10 is N and the other is CR';
  • L 1 to L 3 , Ar 1 , Ar 2 and R' are as defined in Formula 1 above;
  • One of X 1 and X 3 to X 10 is N and the other is CR';
  • L 1 to L 3 , Ar 1 and Ar 2 and R' are as defined in Formula 1 above;
  • One of X 1 , X 2 and X 4 to X 10 is N and the other is CR';
  • L 1 to L 3 , Ar 1 and Ar 2 and R' are as defined in Formula 1 above;
  • One of X 1 to X 3 and X 5 to X 10 is N and the other is CR';
  • L 1 to L 3 , Ar 1 and Ar 2 , and R' are as defined in Formula 1 above.
  • the compound may contain no deuterium or one or more deuterium atoms.
  • the present invention provides a method for producing a compound represented by Formula 1, such as the following Reaction Schemes 1 and 2, for example:
  • X 1 to X 10 , L 1 to L 3 , and Ar 1 and Ar 2 are defined as in Chemical Formulas 1 and 2, respectively.
  • Z is halogen, preferably chloro.
  • Reaction Scheme 1 is a reaction for preparing the core structure of Chemical Formula 1 through a Suzuki coupling reaction.
  • Scheme 2 is also a Suzuki coupling reaction, and it is preferable to carry out in the presence of a palladium catalyst, and the reactor for the Suzuki coupling reaction can be changed as known in the art.
  • the preparation method may be more specific in Preparation Examples and Synthesis 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. .
  • 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, a hole blocking 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 material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. may contain the indicated compounds.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1.
  • the organic material layer may include a hole blocking layer, an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons, and the hole blocking layer, the electron transport layer, the electron injection layer, or the electron transport and electron injection layer.
  • the layer to be simultaneously injected may include the compound represented by Chemical Formula 1 above.
  • the organic material layer may include a light emitting layer and an electron injection and transport layer
  • the electron injection and 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 .
  • 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 is an example of an organic light emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron injection and transport layer (8) and a cathode (4). is shown.
  • the compound represented by Chemical Formula 1 may be included in the light emitting 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 an anode, an organic material layer, and a cathode on a substrate.
  • 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
  • PVD physical vapor deposition
  • depositing a metal or a metal oxide having conductivity or an alloy thereof depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode
  • 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.
  • 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.
  • 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 material 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 compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, 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 matter, anthraquinone, and polyaniline and polythiophene-based conductive compounds, 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.
  • the hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer, and has high hole mobility. material is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive compounds, 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 electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from passing to the hole transport layer without recombination in the light emitting layer, and is also called an electron blocking layer.
  • a material having a smaller electron affinity than the electron transport layer is preferable for the electron blocking layer.
  • the compound represented by Chemical Formula 1 may be included as a material of the electron blocking layer.
  • the light emitting layer may include a host material and a dopant material.
  • the host material the compound represented by Chemical Formula 1 may be used.
  • a condensed aromatic ring derivative or a compound containing a heterocyclic ring can be used as a host material that can be further used.
  • 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 containing 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 "electron injection and transport layer” is a layer that performs both the roles of the electron injection layer and the electron transport layer, and materials that play the role of each layer may be used alone or in combination, but are limited thereto. It doesn't work.
  • the compound represented by Formula 1 may be included as a material for the electron injection and transport layer.
  • the organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.
  • the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
  • 3-Bromo-2-chloropyridine (15g, 77.9 mmol) and (2-(methylthio)naphthalen-1-yl)boronic acid (17.8g, 81.8 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (32.3g, 233.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.8 mmol) 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.
  • intermediate compound A-2-3 (15 g, 55.6 mmol), amine1 (19.6 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-3-4 15 g, 55.6 mmol
  • amine2 24 g, 58.4 mmol
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-4-8 15 g, 55.6 mmol
  • amine3 (20.5 g, 58.4 mmol)
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-3-7 (15 g, 55.6 mmol), amine4 (18.8 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-3-3 (15 g, 55.6 mmol), amine5 (18.8 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-4-3 15 g, 55.6 mmol
  • amine6 (23.2 g, 58.4 mmol)
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-4-1 (15 g, 55.6 mmol), amine7 (21.7 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-2-2 15 g, 55.6 mmol
  • amine8 (21.1 g, 58.4 mmol)
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-3-2 (15 g, 55.6 mmol), amine9 (28.2 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-3-5 15 g, 55.6 mmol
  • amine10 (20.4 g, 58.4 mmol)
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-4-8 15 g, 55.6 mmol
  • amine11 (21.3 g, 58.4 mmol)
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-3-7 (15 g, 55.6 mmol), amine12 (21.3 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-3-5 15 g, 55.6 mmol
  • amine13 28.4 g, 58.4 mmol
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-3-1 (15 g, 55.6 mmol), amine14 (28.4 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-3-8 (15 g, 55.6 mmol), amine15 (25.5 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-4-5 (15 g, 55.6 mmol), amine16 (17.2 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-2-3 (15 g, 55.6 mmol), amine17 (23.2 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-4-2 (15 g, 55.6 mmol), amine18 (23.2 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • compound A-3-3 (15 g, 55.6 mmol), amine19 (19.6 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere, stirred and Refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-2-2 15 g, 55.6 mmol
  • amine20 24 g, 58.4 mmol
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure.
  • intermediate compound A-4-1 (15 g, 55.6 mmol), amine21 (20.5 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to 150 ml of xylene in a nitrogen atmosphere and stirred. and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure.
  • intermediate compound A-2-2 15 g, 55.6 mmol
  • amine22 (19.6 g, 58.4 mmol)
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-2-7 15 g, 55.6 mmol
  • amine23 (24.6 g, 58.4 mmol)
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-3-9 15 g, 55.6 mmol
  • amine24 (18.8 g, 58.4 mmol)
  • sodium tert-butoxide 8 g, 83.4 mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.3 g, 0.6 mmol
  • intermediate compound A-4-4 (15g, 55.6 mmol) and amine25 (21.3g, 58.4 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1 g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) 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.
  • intermediate compound A-2-8 (15g, 55.6 mmol) and amine26 (23.1g, 58.4 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1 g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer.
  • intermediate compound A-2-3 (15g, 55.6 mmol) and amine27 (22.1g, 58.4 mmol) were added to 300 ml of THF, followed by stirring and reflux. Thereafter, potassium carbonate (23.1 g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) 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.
  • intermediate compound A-4-2 (15g, 55.6 mmol) and amine28 (23.1g, 58.4 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (23.1g, 166.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer.
  • a glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water.
  • ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner.
  • solvents such as isopropyl alcohol, acetone, and methanol
  • 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%.
  • a hole transport layer having a thickness of 800 ⁇ was formed by vacuum depositing the following HT-1 compound on the hole injection layer.
  • an electron blocking layer was formed by vacuum depositing the following EB-1 compound to a film thickness of 150 ⁇ on the hole transport layer.
  • the following RH-1 compound and the following Dp-39 compound were vacuum-deposited on the EB-1 deposited film in 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 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 to 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 2 ⁇ 10 - Maintaining 7 to 5 ⁇ 10 ⁇ 6 torr, an organic light emitting device was fabricated.
  • the organic light emitting device of the embodiment using the compound represented by Formula 1 as a red host material has a reduced driving voltage and improved efficiency and It can be seen that the lifetime characteristics are indicated.
  • substrate 2 anode

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant.
PCT/KR2022/019072 2021-11-29 2022-11-29 Nouveau composé et dispositif électroluminescent organique l'utilisant WO2023096459A1 (fr)

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KR20190140586A (ko) * 2018-06-12 2019-12-20 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
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KR100430549B1 (ko) 1999-01-27 2004-05-10 주식회사 엘지화학 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법

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KR20160001702A (ko) * 2014-06-27 2016-01-06 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
CN110317195A (zh) * 2018-03-29 2019-10-11 北京鼎材科技有限公司 有机化合物及其在有机电致发光器件中的应用
KR20190140586A (ko) * 2018-06-12 2019-12-20 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
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