WO2019209031A1 - Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant - Google Patents

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

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WO2019209031A1
WO2019209031A1 PCT/KR2019/004969 KR2019004969W WO2019209031A1 WO 2019209031 A1 WO2019209031 A1 WO 2019209031A1 KR 2019004969 W KR2019004969 W KR 2019004969W WO 2019209031 A1 WO2019209031 A1 WO 2019209031A1
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substituted
unsubstituted
group
light emitting
layer
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PCT/KR2019/004969
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English (en)
Korean (ko)
Inventor
정민우
이동훈
장분재
이정하
한수진
박슬찬
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주식회사 엘지화학
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Priority claimed from KR1020190047557A external-priority patent/KR102206482B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US16/963,189 priority Critical patent/US11925113B2/en
Priority to CN201980009436.8A priority patent/CN111655683B/zh
Priority to EP19792248.7A priority patent/EP3730488B1/fr
Publication of WO2019209031A1 publication Critical patent/WO2019209031A1/fr

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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
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • 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, and an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826 [Contents of the Invention]
  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same. [Measures of problem]
  • the present invention provides a compound represented by the following formula (1).
  • Yo is substituted 0 6 -60 aryl; Or substituted or unsubstituted 0, and 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted 0 1-60 alkyl; Substituted or unsubstituted 0! -60 haloalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0 1-60 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • Haloalkoxy Substituted or unsubstituted 0 3 -60 cycloalkyl; Substituted or unsubstituted 02-60 alkenyl; Substituted or unsubstituted 0 6 -60 aryl; Substituted or unsubstituted 0 6 -60 aryloxy; Or 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted non 0 and
  • 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 second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. to provide.
  • 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.
  • 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.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9. And an example of an organic light emitting element composed of a cathode (4).
  • the present invention provides a compound represented by Chemical Formula 1.
  • the term ⁇ substituted or unsubstituted '' is deuterium; halogen; cyano; nitro; hydroxy; carbonyl; ester; imide; amino; phosphine oxide; alkoxy; aryloxy; Alkylthioxy group; arylthioxy group; alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkyl An amine group; heteroarylamine group; arylamine group; arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of 0 and heteroaryl containing one or more of the atoms, or It means a substituted or unsubstituted linked two or more substituent
  • the ester group may be substituted with oxygen of the ester group having a straight chain, branched or cyclic alkyl group having 6 to 25 carbon atoms or aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto. 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25.
  • it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, butylbutyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group.
  • the boron group is specifically trimethyl boron group, triethyl boron group, butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be 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. Another one 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, 11-propyl, isopropyl, butyl, -butyl, isobutyl, ratchet butyl, 1-Methyl-butyl, 1-ethyl-butyl, pentyl, 11_pentyl, isopentyl, neopentyl, ratchetpentyl, nuclear chamber, 11-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4 -methyl-2- Pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, 11-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuctylmethyl, octyl,
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, it 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.
  • the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl,
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and 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.
  • 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 an exemplary embodiment, 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 a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, or the like, but is not limited thereto.
  • heteroaryl is a heteroaryl containing one or more of 0, ⁇ , and £ as a heterologous element, carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group, Pyridazine, pyrazinyl, quinolinyl, quinazolin, quinoxalinyl, phthalazinyl, pyrido pyrimidinyl, pyrido pyrazinyl, pyrazino pyrazinyl, isoquinoline, indole, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group,
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the example 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 example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heteroaryl.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description about the aryl group described above may be applied except that the arylten is a divalent group. example 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the description of the aforementioned heteroaryl may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the heterocycle is not a monovalent group, and the description of the aforementioned heteroaryl may be applied except that two substituents are formed by bonding.
  • the show may be any one selected from the group consisting of:
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently, 3 , at least two of 3 ⁇ 4 to 3 ⁇ 4 are
  • ⁇ 2 and ⁇ are each independently 0, 3 or ⁇ ’
  • 2 to 5 each independently represent a substituted or unsubstituted 0 6-60 aryl; Or 0! -60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, ⁇ and £,
  • Seedlings are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the show may be any one selected from the group consisting of:
  • Hydrogen Deuterium; Cyano; Or substituted or unsubstituted 0 1-10 alkyl.
  • 3 ⁇ 4 to 3 ⁇ 4 may be hydrogen.
  • the compound may be selected from the group consisting of the following compounds:
  • the compound represented by the formula (1) can be prepared by the same method as in the following scheme 1, for example:
  • the description is as defined in the formula (1).
  • the reaction is a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art.
  • the manufacturing method may be more specific in the production examples to be described later.
  • 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 between the first electrode and the second electrode. 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • An organic light emitting device including at least one organic material layer, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1, and provides an organic light emitting device.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have 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, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer 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 material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
  • the compound represented by Chemical Formula 1 may be used as a host material in the emission layer.
  • the light emitting layer may include two or more types of hosts.
  • one of the hosts may be 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 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 diode 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 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. 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the compound represented by Chemical 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 according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting diode according to the present invention may be fabricated by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time,
  • a conductive metal oxide or an alloy thereof is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is 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, roll coating, etc., but is not limited thereto.
  • the organic light emitting device may be manufactured by sequentially depositing materials.
  • 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 ((1), indium zinc oxide (10)); Combinations of metals and oxides, such as 3 ⁇ 40: hour or 3 ⁇ 2 : ⁇ ; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene], polypyrrole and polyaniline, and the like, but are not limited thereto. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 Ml, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the 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.
  • HOMOC of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic matter.
  • the hole injecting materials include metal porphyrin, oligothiophene, arylamine-based organic matter, nucleonitrile-nuclear azatriphenylene-based organic matter, 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • 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 and transferring the holes to the light emitting layer. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • 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 transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (C3 ⁇ 4); Carbazole series compounds; Dimerized styryl (11161 ⁇ root 1) compounds; 6 o'clock (1; 10 -hydroxybenzo quinoline metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (1) phenylene vinylene) 1) series polymer; Spiro vs. 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 compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative may be a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • styrylamine compound examples include a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, an aryl group, a silyl group, A substituent selected from the group consisting of an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like is not limited thereto.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • an electron transporting material a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include a complex of 8-hydroxyquinoline; Complexes containing show 13 ⁇ 4; 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 in accordance with the prior art.
  • cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum or silver layer in each case.
  • 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, excellent electron injection effect to the light emitting layer or the light emitting material, and 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.
  • said metal complex compound 8-hydroxyquinolinato lithium, bis (8- 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the organic light emitting device 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.
  • Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
  • 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.
  • Fischer Co. product was used as the detergent
  • distilled water filtered secondly as a filter of Mi 11 ipore Co. was used as the distilled water.
  • the ultrasonic cleaning was repeated 10 times with laminar flow twice.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone and methanol 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the substrate was washed with oxygen plasma for 5 minutes and then transported to a vacuum evaporator.
  • a hole injection layer was formed by thermal vacuum deposition of the following ⁇ 1 compound to a thickness of 50 particles on the 110 transparent electrode prepared as described above.
  • the following -1 compound was vacuum-deposited to a thickness of 250 particles on the hole injection layer to form a hole transport layer, and then on the hole transport certificate.
  • the compound was vacuum deposited to a thickness of 50 shows to form an electron blocking layer.
  • Compound 1, the following compound-1, and phosphorescent dopant ⁇ 01) -1 prepared in Example 1 as a light emitting layer on the electron blocking layer were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 particles. It was.
  • the following -1 compound was vacuum deposited to a thickness of 250 ⁇ on the light emitting layer to form an electron transport layer, and the following £ 1-2 compound and the needle were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to inject 100 nm thick electrons.
  • a layer was formed.
  • Aluminum was deposited on the electron injection layer to a thickness of 1000 particles to form a cathode.
  • An organic light-emitting device was manufactured in the same manner as in Experiment 1, except that the compound shown in Table 1 was used instead of the compound 1 prepared in Example 1.
  • CE1 CE12 and CE3 compounds of the following Table 1 are as follows.
  • the organic light emitting diodes of the Experimental Example and the Comparative Experimental Example were measured voltage and efficiency at a current density of 10— / 011 2 , and lifespan was measured at a current density of 50 ⁇ : #, and the results are shown in Table 1 below. At this time, 1 95 means the time to be 95% of the initial luminance.
  • Substrate 2 Anode

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un dispositif électroluminescent organique l'utilisant.
PCT/KR2019/004969 2018-04-24 2019-04-24 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant WO2019209031A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US16/963,189 US11925113B2 (en) 2018-04-24 2019-04-24 Heterocyclic compound and organic light emitting device comprising the same
CN201980009436.8A CN111655683B (zh) 2018-04-24 2019-04-24 新的杂环化合物和包含其的有机发光器件
EP19792248.7A EP3730488B1 (fr) 2018-04-24 2019-04-24 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant

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KR10-2018-0047306 2018-04-24
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