WO2018084423A2 - Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant Download PDF

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WO2018084423A2
WO2018084423A2 PCT/KR2017/010057 KR2017010057W WO2018084423A2 WO 2018084423 A2 WO2018084423 A2 WO 2018084423A2 KR 2017010057 W KR2017010057 W KR 2017010057W WO 2018084423 A2 WO2018084423 A2 WO 2018084423A2
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compound
group
layer
unsubstituted
substituted
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PCT/KR2017/010057
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WO2018084423A3 (fr
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정민우
이정하
이동훈
박태윤
장분재
조성미
허동욱
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주식회사 엘지화학
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Priority claimed from KR1020170116136A external-priority patent/KR101885899B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US16/079,962 priority Critical patent/US11208402B2/en
Priority to JP2018548024A priority patent/JP6638160B2/ja
Priority to CN202111310111.9A priority patent/CN114163421A/zh
Priority to EP17867330.7A priority patent/EP3415512B1/fr
Priority to CN201780017179.3A priority patent/CN109071513B/zh
Publication of WO2018084423A2 publication Critical patent/WO2018084423A2/fr
Publication of WO2018084423A3 publication Critical patent/WO2018084423A3/fr
Priority to US17/523,264 priority patent/US11802123B2/en

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    • 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]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting 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, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often formed of a multilayer structure composed of different materials, and 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. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • Each X is independently N or CH
  • An and Ar 2 are each independently substituted or unsubstituted C 6 -60 aryl; Or C 2 -60 heteroaryl including at least one hetero atom selected from the group consisting of substituted or unsubstituted N, 0, S and Si,
  • R are the same as each other, represented by -L 2 -Ar 3 ,
  • L 2 is a single bond; Substituted or unsubstituted C 6 — 60 arylene; Or N, 0, S and
  • Ar 3 is substituted or unsubstituted C 6 -60 aryl; Or at least one hetero selected from the group consisting of substituted or unsubstituted N, 0, S and Si C 2 -60 heteroaryl containing an atom,
  • R is not unsubstituted phenyl.
  • the present invention is a crab 1 electrode; A second electrode provided to face the first electrode; And an organic light emitting device comprising at least one organic material layer provided between the first and second crab electrodes, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. do.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compound represented by Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element consisting of 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.
  • the present invention provides a compound represented by Chemical Formula 1.
  • substituted or unsubstituted 1 is a 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; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, 0
  • the substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group, and can be interpreted as a substituent to which two phenyl groups are linked.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40.
  • the oxygen of the ester group may be substituted with a linear, 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.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t -butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, 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, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonactylmethyl, octyl, n-octyl, tert-octyl, 1 Methylheptyl, 2-ethyln
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary 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-part Tenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl— 1-yl, 2, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naph Yl-1-yl) vinyl— 1-yl, 2, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms. According to one 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.
  • 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.
  • the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl 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
  • the heterocyclic group is a heterocyclic group including one or more of 0, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include thiophene group, furan group, pil group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acri Dill 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, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthrol ine
  • the aralkyl group, aralkenyl group, alkylaryl group The aryl group in an arylamine group is the same as the example of the aryl group mentioned above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • Formula 1 is represented by the following Formula 1-1:
  • N Preferably all are N.
  • silver is a single bond; Or phenylene.
  • a and Ar 2 are each independently phenyl or biphenylyl.
  • L 2 is a single bond; Or phenylene.
  • Ar 3 is C 6 -60 aryl unsubstituted or substituted with one or more deuterium, or one or more cyano; Or C 2 -60 heteroaryl comprising at least one hetero atom selected from the group consisting of N, 0, S and Si, substituted with one or more dihydrogen, or one or more cyano.
  • Ar 3 is any one selected from the group consisting of:
  • nl is an integer of 0 to 4,
  • n2 is an integer of 0 to 5
  • n3 is an integer of 0-9.
  • R is phenyl unsubstituted with cyano or biphenylrin, naphthyl, unsubstituted or substituted with 1 to 5 deuterium, phenanthrenyl, unsubstituted with 1 to 5 deuterium.
  • Dimethylfluorenyl optionally substituted with 1 to 5 deuterium, benzofuranyl, benzothiophenyl, carbazolyl pyridinephenyl, 9, 9-dimethyl-xanthene, unsubstituted or substituted with 1 to 5 deuterium. Nil or 9, 9-dimethyl-thioxanthenyl.
  • the compound represented by Formula 1 may be selected from the group consisting of the following compounds.
  • the compound represented by Chemical Formula 1 may be prepared by the following method.
  • the present invention provides an organic light emitting device including the compound represented by Formula 1.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the crab electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1 to provide an organic light emitting device. do.
  • the organic material layer of the organic light emitting device of the present invention may be formed of a single layer structure, but may be formed of a multilayer 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 an organic layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole is represented by the formula (1) It includes a compound represented.
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic layer may include an electron transport layer, or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).
  • the electron transport layer, the electron injection layer, or a layer for the electron transport and electron injection at the same time includes a compound represented by the formula (1).
  • the organic material layer may include 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 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.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • FIG. 2 shows an example of an organic light emitting element consisting of 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.
  • the compound represented by Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.
  • the organic light-emitting device there is more than one layer of said organic material layer can be made of materials and methods that are known in the art, except that it comprises a compound of the formula (1).
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a crab 2 electrode on a substrate. At this time, the metal or conductive metal oxides or alloys thereof are formed on the substrate by using a physical vapor deposition deposition (PVD) method such as sputtering or e-beam evaporat ion.
  • PVD physical vapor deposition deposition
  • the deposition may be performed to form an anode, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited thereon.
  • 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 layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (W0 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 anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • 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 ( ⁇ ) and indium zinc oxide (IZ0); ⁇ 0: ⁇ 1 or SN0 2 : A combination of a metal and an oxide such as Sb; Poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PED0T), polypyrrole and Conductive polymers such as polyaniline, and the like, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide ( ⁇ ) and indium zinc oxide (IZ0); ⁇ 0: ⁇ 1 or SN0 2 : A combination of a metal and an oxide such as Sb; Poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy)
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material may include metals such as magnesium, carbon, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes.
  • the hole injection material has an excellent hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material.
  • the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. It is preferred that the HOMOC highest occupied molecul ar orbital of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer.
  • hole injection materials include metal porphyr, oligothiophene, arylamine-based organic matter, nucleonitrile-nucleated azatriphenylene-based organic material, quinacridone-based organic material, and perylene ) Organic materials, anthraquinone and 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 holes to the light emitting layer.
  • a hole transporting material is a material capable of transporting holes from an anode or a hole injection layer to a light emitting layer. This is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer 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 region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and preferably a material having good quantum efficiency with respect to fluorescence or phosphorescence.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimer i zed styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Polymers of the poly (P-phenylenevinylene) (PPV) family; Spi ro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimer i zed styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds Polymers of the poly (P-phenylenevinylene) (PPV) family
  • Spi ro compounds Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and perifolathene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the arylamine, and a substituent selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino groups is substituted or unsubstituted.
  • the transport material receives electrons from the electron injection layer
  • the electron transporting material is a layer that transports electrons to the light emitting layer.
  • a material capable of injecting electrons well from the cathode to the light emitting layer a material having high mobility to electrons is suitable.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, has an excellent electron injection effect for the light emitting layer or the light emitting material, hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and their derivatives, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, 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) ( 0-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2-naphlato) gallium, etc.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 3'A (32.7 g, 7) through a nucleic acid and an ethyl acetate column.
  • intermediate l ′ (15.0 g, 48 ⁇ l ol) and potassium acetate (14 g, 142 ⁇ l) were mixed, added to 150 ml of dioxane and heated with stirring.
  • the temperature was lowered to room temperature and filtered. Water was added to the filtrate, extraction was performed with chloroform, and the organic layer was dried over anhydrous magnesium sulfate.
  • Compound 1-1 (15.7 g, 91%) was prepared by recrystallization of ethane with distillation under reduced pressure.
  • intermediate 1-1 (15.7 g, 50 ⁇ l ol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (14.6 g, 55 ⁇ l ol) were added to 200 ml of tetrahydrofuran. Stir and reflux. Thereafter, potassium carbonate (20.6 g, 149 ⁇ l) was dissolved in 60 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.7 g, 1.5 ⁇ l ol) was added thereto. After 18 hours of reaction, the silver was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate.
  • intermediate 2-1 (14.0 g, 44 ⁇ ol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (13 g, 48 mmol) were added to 100 ml of tetrahydrofuran. Stir and reflux. Thereafter, Potassium carbonate (18.4 g, 132 ⁇ l) was dissolved in 50 ml of water, followed by stirring, followed by tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 ⁇ l). After 18 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate.
  • Example 2 (9.5 g, 61%).
  • intermediate 3-1 (15.7 g, 50 ⁇ l ol) and 2-chloro-4,6_diphenyl-1,3,5-triazine (14.4 g, 54 ⁇ l ol) were added to 200 ml of tetrahydrofuran.
  • potassium carbonate (20.3 g, 147 mmol) was dissolved in 60 ml of water, followed by sufficient stirring, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 1.5 Pa) was added thereto.
  • the silver was lowered and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate.
  • intermediate 4-1 (14.5 g, 46 ⁇ l ol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (13.5 g, 50 ⁇ l ol) were added to 200 ml of tetrahydrofuran. Stir and reflux. Thereafter, potassium carbonate (19.0 g, 138 ⁇ l) was dissolved in 60 ml of water, followed by stirring. Then, tetrakistriphenyl-phosphinopalladium (1.6 g, 1.4 ⁇ l) was added thereto. After 18 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate.
  • Example 4 (9.5 g, 61%).
  • Example 6 (12.6 g, 81%).
  • Example 8 (12 g, 77%) was prepared in the same manner as in Example 7, except for changing the intermediate 1-2 from the material to react with the reaction.
  • Example 9 (10 g, 68%) was prepared in the same manner as in Example 7, except that the material reacting with Intermediate 1-2 was changed as described above.
  • Example 10 (11 g, 703 ⁇ 4>) was prepared in the same manner as in Example 7, except that the material reacting with Intermediate 1-2 was changed as in the reaction method.
  • Example 11 (12 g, 74 «) was prepared in the same manner as in Example 7, except that the material reacted with the intermediate 1-2 as in the reaction method.
  • Example 12 (11 g, 68%) was prepared in the same manner as in Example 2, except that the intermediate 2-2 and the reacting material were different from each other.
  • Example 13 (7 g, 41%) was prepared in the same manner as in Example 3, except that the material reacting with the Intermediate 3-2, as in the reaction method, was prepared.
  • Example 14 (10 g, 63%) was prepared.
  • Example 15 (13 g, 78%) was prepared in the same manner as in Example 7, except for changing the intermediate 1-2 from the material to react with the reaction.
  • Example 16 (11 g, 70%) was prepared in the same manner as in Example 7, except that the material reacted with Intermediate 1-2.
  • Example 17 (9g, 53%) was prepared in the same manner as in Example 7, except for changing the material reacting with Intermediate 1-2, as in Banungsik.
  • Example 18 (10 g, 60%) was prepared in the same manner as in Example 7, except that the material reacting with the intermediate 1-2 was repeated as in the reaction.
  • Example 19 (11 g, 71%) was prepared in the same manner as in Example 7, except for changing the reaction material with Intermediate 1-2 as in the above Scheme.
  • Example 20 (11 g, 65%) was prepared in the same manner as in Example 7, except for changing the reaction material with Intermediate 1-2 as in the above Scheme.
  • Example 21 (11 g, 68%) was prepared in the same manner as in Example 7, except for changing the intermediate 1-2 from the material to react with the reaction.
  • Example 22 (8g, 51%) was prepared in the same manner as in Example 7, except for changing the materials reacting with the intermediates 1 and 2, as in the reaction.
  • Example 23 (13g, 80%) was prepared in the same manner as in Example 7, except for changing the material reacting with Intermediate 1-2, as in Banungsik.
  • Example 24 (11 g, 69%) was prepared in the same manner as in Example 7, except that the material reacting with Intermediate 1-2 was changed as in the reaction method.
  • Example 25 As in the reaction method, Example 25 (5 g, 31%) was prepared in the same manner as in Example 7, except that the material reacted with the intermediate 1-2.
  • Example 27 (9.5 g, 61%).
  • intermediate l ′ (15 g, 48 ⁇ l ol) and compound 28-1 (22/7 g, 52 mmol) were added to 200 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (20 g, 142 ⁇ ol) was dissolved in 60 ml of water, followed by sufficient stirring, and then tetrakistriphenyl-phosphinopalladium (1.6 g, 1.4 mmol) was added thereto. After 16 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. The organic layer was then ' crystallized after distillation under reduced pressure using ethyl acetate. The resulting solid was filtered and then dried to prepare compound 27-2 (16 g, 6W).
  • compound 27-2 (10 g, 21 ⁇ ol) and (4- (pyridin-2-yl) phenyl) boronic acid (8.0 g, 40 ⁇ ol) were added to 150 ml of tetrahydrofuran and stirred and refluxed. It was. Then, potassium phosphate (23.4 g, 110 ⁇ ol) was dissolved in 60 ml of water, and then stirred. After stirring, bis (dibenzylideneacetone) palladium (0.6 g, 1.1 mmol) and tricyclonuclear phosphine (0.6 g, 2.2 Xol) was added. After reaction for 24 hours, the temperature was lowered to room temperature and filtered.
  • Example 27 (6 g, 41%).
  • Example 29 (6 g, 54%) was prepared in the same manner as in Example 27, except that Compound 27-2 and the material reacting with Compound 27-2 were reacted.
  • Example 31 (8 g, 65%) was prepared in the same manner as in Example 27, except that Compound 27-2 and the material reacting with Compound 27-2 were reacted.
  • Example 32 (3.29%) was synthesized in the same manner as in Example 27, except that Compound 27-2 and the material reacting with Compound 26-2 were added.
  • Example 33 (7 g, 58%) was prepared in the same manner as in Example 28, except that the material reacting with Compound 28-2 was different.
  • Example 34 (6 g, 48%) was prepared in the same manner as in Example 28, except that the substance reacting with Compound 28-2 was changed.
  • Example 35 (3 g, 26%) was prepared in the same manner as in Example 28, except that Compound 28-2 and the material reacting with Compound 28-2 were changed.
  • Example 36 (9 g, 60%) was prepared in the same manner as in Example 28, except that the material reacted with Compound 28-2.
  • Example 37 (10 59%) was prepared in the same manner as in Example 28, except that Compound 28-2 and the material reacting with Compound 28-2 were changed.
  • Example 38 (14 g, 78%) was prepared in the same manner as in Example 28, except that Compound 28-2 and the material reacting with Compound 28-2 were changed.
  • Example 39 (8 g,%) was prepared in the same manner as in Example 28, except that the material reacting with Compound 28-2 was changed.
  • the following compound was used as a comparative example.
  • a glass substrate coated with a thin film of I0 (indium tin oxide) having a thickness of 1,300 A was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • I0 indium tin oxide
  • Fischer Co. product was used as the detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water. After washing ITO for 30 minutes, repeat ultrasonic cleaning with distilled water for 2 minutes.
  • the hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 50 A on the ⁇ transparent electrode prepared as described above.
  • a hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound at a thickness of 250 A on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the following HT-2 compound at a thickness of 50 A on the HT-1 deposition film.
  • Example 1 The compound of Example 1 and the phosphorescent dopant YGD-1 were co-deposited on the HT-2 deposited film at a weight ratio of 88:12 to form a light emitting layer having a thickness of 400A.
  • the following ET-1 material was vacuum deposited to a thickness of 250 A on the light emitting layer, and the following ET-2 material was co-deposited with Li in a 2% weight ratio to a thickness of 100 A to form an electron transport layer and an electron injection layer.
  • Aluminum was deposited to a thickness of 1000 A on the electron injection layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 A / sec
  • the aluminum was maintained at the deposition rate of 2 A / sec
  • the vacuum degree during deposition was maintained at 1 ⁇ 1 ( ⁇ 7 ⁇ 5X 10 "8 torr). It was.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-27, except for using the compound shown in Table 2 below instead of the compound of Example 1 in Experimental Example 1-27.
  • the driving voltage and the luminous efficiency of the organic light emitting diodes manufactured in Experimental Examples 1-1 to 1-52 and Comparative Experimental Examples 1-1 to 1-36 were measured at a current density of 10 mA / cm 2 , and 50 mA / cm
  • the time (LT95) to become 95% of initial luminance at the current density of 2 was measured. The results are shown in Tables 1 and 2 below.
  • Example 7 3.6 60 0.46, 0.53 80 1-8
  • Example 8 3.7 74 0.46, 0.54 85
  • Example 23 3.9 74 0.46, 0.53. 218 1-50
  • Example 24 3.7 66 0.46, 0.52 175
  • the compounds of the present invention When used as a light emitting layer, the effect was excellent in terms of voltage, efficiency and lifetime.
  • the compound of the present invention is used with the YGH1 compound (Experimental Examples 1-27 to 1-52), it was confirmed that the life is significantly improved.
  • the life difference appears depending on the substitution position of the dibenzofuran of the compounds of Example 1 and Examples 2 to 4, it was confirmed that the life is improved at a specific position. This tendency was also confirmed in the compounds of Examples 12-16.
  • the efficiency characteristics are different depending on the substituent type and substitution position of R in Formula 1, efficiency and voltage , The excellent material in terms of lifespan could be examined.
  • Thin film coated glass with an indium t in oxide (IT0) thickness of 1,300 A The substrate was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly was used as a filter of a Millipore Co. product. After washing IT0 for 30 minutes, the ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. The following HI-1 compound was prepared on the ITO transparent electrode prepared as above.
  • HT-1 compound was vacuum-deposited to a thickness of 800 A on the hole injection layer
  • HT-3 compound was vacuum deposited to a thickness of 500 A in order to form a hole transport layer.
  • the compound of Example 1, GH1, and phosphorescent dopant GD-1 were co-deposited on the hole transport layer at a weight ratio of 47.5: 47.5: 5 to form a light emitting layer having a thickness of 400 A.
  • Vacuum depositing the following ET-3 compound to a thickness of 50 A on the light emitting layer to form a hole blocking layer, and vacuum deposition of the following ET-4 material and LiQ at a weight ratio of 1: 1 on the hole blocking layer to electrons of 250 A A transportworm was formed.
  • 10 A-thickness of Medium Pluride (LiF) was sequentially deposited on the electron transport layer, and aluminum was deposited to a thickness of 1000 A thereon to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at the deposition rate of 2 A / sec. — 7 to 5 X 10 torr was maintained.
  • a glass substrate (corning 7059 glass) coated with a thin film having an indium tin oxide (IT0) of ⁇ , ⁇ thickness was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. Fischer Co. was used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After washing IT0 for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, methanol, and dried. The following HI-1 compound was vacuum-deposited to a thickness of 500 A on the prepared IT0 transparent electrode to form a hole injection layer.
  • IT0 indium tin oxide
  • a hole transport layer was formed by vacuum depositing the following HT-1 compound to a thickness of 400 A on the hole injection layer, and a host HI and a dopant D1 compound (2.5 ⁇ %) were vacuum deposited to a thickness of 300 A as a light emitting layer.
  • the following compound ET-A was vacuum deposited to a thickness of 50 A on the emission layer to form an a-electron transport layer.
  • the compound of Example 1 and LiQCLithium Quinolate) were vacuum deposited on the a—electron transport layer at a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 350A.
  • the cathode was formed by sequentially depositing lithium fluoride (LiF) and aluminum at a thickness of 2,000 A on the electron injection and transport layer sequentially.
  • the deposition rate of the organic material in the above process 0.4 ⁇ 0.7 A / sec was maintained, the flow of lithium fluoride of the cathode was 0.3 A / sec, aluminum is vacuum was maintained during the deposition rate, the deposition of 2 A / sec is 2X10- 7 ⁇ 5X10 "6 torr
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 3-1, except that the compound shown in Table 7 was used instead of the compound of Example 1 in Experimental Example 3-1.
  • the organic light emitting diodes manufactured in Experimental Examples 3-1 to 3-16 and Comparative Experimental Examples 3-1 and 3-2 were measured for driving voltage and luminous efficiency at a current density of 10 mA / cm 2 , and 50 mA / cm
  • the time (LT95) to become 95% of initial luminance at the current density of 2 was measured. The results are shown in Tables 6 and 7 below.
  • Example 16 and the following CoH1 compounds were prepared in a 5: 5 weight ratio, and then physically mixed, and ground and loaded into an evaporation source.
  • the premixed composition was thermally co-evaporated at a rate of 2 A / sec in a vacuum chamber under a pressure of less than 10 Torr and deposited onto the glass substrate.
  • the substrates were continuously replaced after deposition of the 500 A film without interrupting deposition and source angles.
  • the composition of the film was analyzed by high performance liquid chromatography (HPLC) and the results are shown in Table 8 below.
  • Experimental Examples 4-2 to 4-4 Except for using the compound shown in Table 8 in place of the compound of Example 16 in Experimental Example 4-1, the experiment was carried out in the same manner as in Experimental Example 4-1.
  • the deposition rate of the composition during co-deposition by deuterium may vary.

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  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
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  • Electroluminescent Light Sources (AREA)
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Abstract

La présente invention concerne un nouveau composé hétérocyclique et un élément électroluminescent organique le comprenant.
PCT/KR2017/010057 2016-11-07 2017-09-13 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant WO2018084423A2 (fr)

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US16/079,962 US11208402B2 (en) 2016-11-07 2017-09-13 Heterocyclic compound and organic light emitting device comprising the same
JP2018548024A JP6638160B2 (ja) 2016-11-07 2017-09-13 新規なヘテロ環化合物およびこれを利用した有機発光素子
CN202111310111.9A CN114163421A (zh) 2016-11-07 2017-09-13 新的杂环化合物和包含其的有机发光器件
EP17867330.7A EP3415512B1 (fr) 2016-11-07 2017-09-13 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant
CN201780017179.3A CN109071513B (zh) 2016-11-07 2017-09-13 新的杂环化合物和包含其的有机发光器件
US17/523,264 US11802123B2 (en) 2016-11-07 2021-11-10 Heterocyclic compound and organic light emitting device comprising the same

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019132374A1 (fr) * 2017-12-27 2019-07-04 삼성에스디아이 주식회사 Composé organique, composition, dispositif optoélectronique organique et appareil d'affichage
WO2020022779A1 (fr) * 2018-07-24 2020-01-30 주식회사 엘지화학 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant
CN111971281A (zh) * 2018-07-24 2020-11-20 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
CN112166112A (zh) * 2018-05-30 2021-01-01 默克专利有限公司 用于有机电子器件的组合物
JP2022503940A (ja) * 2018-10-02 2022-01-12 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物、これを含む有機発光素子、有機発光素子の有機物層用組成物および有機発光素子の製造方法
CN113950474A (zh) * 2019-11-05 2022-01-18 Lt素材株式会社 杂环化合物以及包括其的有机发光装置
WO2023008795A1 (fr) * 2021-07-26 2023-02-02 엘티소재주식회사 Composé hétérocyclique, dispositif électroluminescent organique le comprenant, et composition pour couche organique
US11588118B2 (en) 2018-10-30 2023-02-21 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11795161B2 (en) 2018-11-16 2023-10-24 Lg Chem, Ltd. Compound and organic light emitting device comprising same
US11807632B2 (en) 2018-10-22 2023-11-07 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000051826A (ko) 1999-01-27 2000-08-16 성재갑 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009053382A1 (de) * 2009-11-14 2011-05-19 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
CN105518103B (zh) * 2013-09-11 2018-12-21 默克专利有限公司 有机电致发光器件
CN114394958A (zh) * 2014-05-05 2022-04-26 默克专利有限公司 用于有机发光器件的材料
US10749113B2 (en) * 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US9406892B2 (en) * 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000051826A (ko) 1999-01-27 2000-08-16 성재갑 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200388765A1 (en) * 2017-12-27 2020-12-10 Samsung Sdi Co., Ltd. Organic compound, composition, organic optoelectronic device, and display apparatus
US11844271B2 (en) 2017-12-27 2023-12-12 Samsung Sdi Co., Ltd. Organic compound, composition, organic optoelectronic device, and display apparatus
WO2019132374A1 (fr) * 2017-12-27 2019-07-04 삼성에스디아이 주식회사 Composé organique, composition, dispositif optoélectronique organique et appareil d'affichage
CN112166112A (zh) * 2018-05-30 2021-01-01 默克专利有限公司 用于有机电子器件的组合物
WO2020022779A1 (fr) * 2018-07-24 2020-01-30 주식회사 엘지화학 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant
CN111971281A (zh) * 2018-07-24 2020-11-20 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
US12010912B2 (en) 2018-07-24 2024-06-11 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
CN111971281B (zh) * 2018-07-24 2023-09-19 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
JP2022503940A (ja) * 2018-10-02 2022-01-12 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物、これを含む有機発光素子、有機発光素子の有機物層用組成物および有機発光素子の製造方法
EP3862353A4 (fr) * 2018-10-02 2022-08-10 LT Materials Co., Ltd. Composé hétérocyclique, diode électroluminescente organique le comprenant, composition pour couche organique de diode électroluminescente organique, et procédé de fabrication de diode électroluminescente organique
US11807632B2 (en) 2018-10-22 2023-11-07 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
US11588118B2 (en) 2018-10-30 2023-02-21 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11795161B2 (en) 2018-11-16 2023-10-24 Lg Chem, Ltd. Compound and organic light emitting device comprising same
CN113950474A (zh) * 2019-11-05 2022-01-18 Lt素材株式会社 杂环化合物以及包括其的有机发光装置
WO2023008795A1 (fr) * 2021-07-26 2023-02-02 엘티소재주식회사 Composé hétérocyclique, dispositif électroluminescent organique le comprenant, et composition pour couche organique

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