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WO2018164545A1 - 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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WO2018164545A1
WO2018164545A1 PCT/KR2018/002853 KR2018002853W WO2018164545A1 WO 2018164545 A1 WO2018164545 A1 WO 2018164545A1 KR 2018002853 W KR2018002853 W KR 2018002853W WO 2018164545 A1 WO2018164545 A1 WO 2018164545A1
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compound
group
light emitting
layer
substituted
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Korean (ko)
Inventor
강민영
박태윤
조성미
문정욱
정민우
이정하
이동훈
채미영
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LG Chem Ltd
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LG Chem Ltd
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Priority to CN201880002742.4A priority Critical patent/CN109415351B/zh
Priority claimed from KR1020180027923A external-priority patent/KR102034196B1/ko
Publication of WO2018164545A1 publication Critical patent/WO2018164545A1/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
    • 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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Definitions

  • the present invention relates to a novel 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 and fast response time. Luminance. Many studies have been conducted because of excellent driving voltage and response speed characteristics.
  • An organic light emitting diode generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic layer is often composed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device.
  • the hole injection layer for example, the hole injection layer.
  • Hole transport layer Light emitting layer, electron transport insect. It may be made of an electron injection worm.
  • Patent Document 0001 Korean Patent Publication No. 10-2013— 073537
  • the present invention relates to a novel seven light-emitting device comprising a heterocyclic compound compound and.
  • Xi. And 3 ⁇ 4 are each independently N or "CR '. Provided that at least one of them is N,
  • Y is 0 or S.
  • L is C f no R 'is hydrogen or deuterium or substituted or unsubstituted alkyl.
  • R 5 . Re. 7 . And 3 ⁇ 4 are each independently hydrogen, deuterium.
  • k is an integer from 1 to 10.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layer provide an organic light emitting device including the compound of the present invention described above.
  • the example of the organic light emitting element which consists of the anode 2, the light emitting layer 3, and the cathode 4 is shown.
  • FIG. 2 is a substrate (1).
  • An example of an organic light emitting element composed of 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 is shown.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting device, and may improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device. Especially .
  • Compound represented by the formula (1) is hole injection. Hole transport. Hole injection and transportation. It can be used as a luminescence, electron transport, or electron injection material.
  • Xi, X 2 and 3 ⁇ 4 are each independently N or CR ′, provided that at least one of them is N.
  • Y is 0 or S
  • R ' is hydrogen.
  • R 2 . R 3 , R 4 . R 5 . R 6 . 7 . R 8 and 3 ⁇ 4 are each independently hydrogen, deuterium.
  • a substituted or unsubstituted d-60 alkyl, substituted or unsubstituted d-60 alkyl silyl group, a substituted or unsubstituted ring including a substituted or unsubstituted HM aryl or N, 0 and S increase one or more C 5 - 60 Heteroaryl,
  • k is an integer from 1 to 10. It means the bond connected to another substituent.
  • substituted or unsubstituted is deuterium halogen group; Nitrile group: Nitro group; Hydroxyl group; Carbonyl group; Ester group imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl group boron group; Alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine group; Heteroarylamine group arylamine group; Aryl phosphine group; Or N.
  • a substituent to which two or more substituents are linked may be a biphenyl group.
  • the biphenyl group may be an aryl group. It can be interpreted as a substituent in which two phenyl groups are linked.
  • Carbon number of the carbonyl group in the present specification is not particularly limited. It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • 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.
  • a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms Specifically, but may be a compound of the following structural formula. It is not limited to this.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25.
  • a compound of the following structure It is not limited to this.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group. Propyldimethylsilyl group. Triphenylsilyl group, but not limited to diphenylsilyl group, phenylsilyl group and the like.
  • the boron group is specifically trimethylboron group. Triethylboron group, t-butyldimethylboron group, triphenylboron 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, and the carbon number is particularly. Although it is not limited, it is preferable that it is 1-40. According to one embodiment. Carbon number of the said alkyl group is 1-20. 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. Specific examples of the alkyl group include methyl. ethyl. Profile, 11-profile. Isopropyl, butyl, n-butyl, isobutyl, ter t-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-methylnuclear chamber. Cyclopentylmethyl ⁇ cyclonucleotylmethyl ⁇ octyl. n-octyl, ter t-octyl.
  • the alkenyl group may be straight or branched chain. Although carbon number is not specifically limited, It is preferable that it is 2-40. 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 thereof include vinyl ⁇ 1-propenyl and isopropenyl.
  • the cycloalkyl group is not particularly limited. Preferably 3 to 60 carbon atoms. According to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment. Carbon number of the said cycloalkyl group is 3-20. According to another embodiment. Carbon number of the said cycloalkyl group is 3-6. Specifically Cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl. 2.3-Dimethylcyclopentyl, cyclonuclear chamber.
  • 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 this embodiment, the number of carbon atoms of the aryl group is according to this embodiment. Carbon number of the said aryl group is 6-20.
  • the aryl group is a phenyl group as the monocyclic aryl group. It may be a biphenyl group, a terphenyl group, and the like. It is not limited to this.
  • As said polycyclic aryl group a naphthyl group. Anthracenyl group phenanthryl group, pyrenyl group. Perylyl group. Crysenyl group.
  • a fluorenyl group may be used, but the present invention is not limited thereto. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Heterocyclic group is a heterocyclic group containing at least one of N. Si and S as a heterogeneous element, carbon number is not particularly limited. It is preferable that it is C2-C60.
  • heterocyclic groups are thiophene groups. Furangi. Blood. Imidazole. Thiazole group, oxazole group, oxadiazole group. Triazole. Pyridyl groups. Bipyridyl groups. Pyrimidyl groups, triazine groups. Triazole groups, acridil groups, pyridazine groups. Pyrazinyl groups. Quinolinyl and quinazoline groups.
  • the aryl group in the ⁇ aralkyl group, the aralkenyl group ⁇ alkylaryl group, and the arylamine group is the same as the example of the aryl group described above.
  • the alkyl group in the alkylamine group is the same as the example of the alkyl group mentioned above.
  • the heteroaryl of the ⁇ heteroaryl amine may be applied to the aforementioned heterocyclic group. In this specification.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In this specification.
  • the description of the above-described aryl group can be applied except that arylene is bivalent.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is divalent.
  • the description of the aforementioned aryl group or cycloalkyl group may be applied except that the “hydrocarbon ring” is not monovalent and is formed by combining two substituents.
  • the heterocyclic ring is not 1 group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • the compound represented by Formula 1 may have a weight average molecular weight (Mvv) of less than 750.
  • the compound represented by Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 1-1 to 1-7.
  • Y. Ri. R 2 . R 3 , 4 . 5 . Re. R 7 . 8 . R9 and k are as defined above.
  • ⁇ May be phenyl or biphenyl.
  • R 2 , R 3 , R 4 . Rs, e, 7 3 ⁇ 4 and R 9 are each independently deuterium. methyl. Ethyl propyl, phenyl, biphenyl or fluorenyl
  • k may be 1 or 2
  • the compound represented by Formula 1 is represented by Formula 1
  • Triazine pyridine. Pyrimidine
  • benzofuran group benzocyopene
  • phenylene or biphenylene of para bond phenylene or biphenylene of para bond
  • the substituent of triazine pyridine. Pyrimidine
  • pyridine is at least 4 aromatic ring chains
  • the organic light emitting device using the same has high efficiency. Low driving voltage. It may have high brightness and long life. Also.
  • the compound represented by Chemical Formula 1 may be prepared by a preparation method such as the following Schemes 1A to 1C. The manufacturing method may be more specific in the production examples to be described later.
  • the compound represented by Chemical Formula 1 is a starting material according to the structure of the compound to be prepared by referring to the contents of Schemes 1A to 1C.
  • the type of reactor and the type of catalyst can be replaced by a suitable one.
  • the present invention provides an organic light emitting device including the compound represented by Chemical Formula 1.
  • the present invention is a first electrode; The first electrode and A second electrode provided oppositely; And at least one organic material layer provided between the first electrode and the second electrode. At least one layer of the organic material layer includes a compound represented by Formula 1.
  • An organic light emitting device is provided.
  • 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 material 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 is a hole injection layer. Hole transport layer. Or a layer for simultaneously injecting and transporting holes, wherein the hole injection layer and the hole transport layer.
  • the layer for simultaneously injecting and transporting a hole may include the compound represented by Chemical Formula 1.
  • the organic material filling may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1. Also.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1. Also.
  • the electron transport layer, the electron injection layer, or a layer for simultaneously injecting and transporting electrons includes the compound represented by Formula 1.
  • the compound represented by the formula (1) according to the present invention is excellent in thermal stability. Deep HOMO level above 6.0 eV. High triplet energy (ET). And hole stability.
  • electron injection and electron to the compound represented by the formula (1) When used for organic layer that can transport simultaneously. ⁇ -type dopants used in the art can be used in combination.
  • the organic material charge may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1. Also.
  • the organic light emitting device may have a structure in which one or more organic layers and a cathode are sequentially stacked. Also.
  • 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. 1 shows a substrate 1, an anode 2.
  • the example of the organic light-emitting element which consists of the light emitting layer 3 and the cathode 4 is shown.
  • the compound represented by Chemical Formula 1 may be included in the light emitting insect.
  • 2 is a substrate (1).
  • the example of the organic light emitting element which consists of the light emitting layer 7, the electron carrying layer 8, and the cathode 4 is shown.
  • the compound represented by Formula 1 is the hole injection layer.
  • Hole transport layer It may be included in one or more layers of 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 of the organic layers includes the compound represented by Chemical Formula 1.
  • the organic material insects may be formed of the same material or different materials.
  • An organic light emitting device according to the present invention is a first electrode on a substrate.
  • the organic material insect and the second electrode may be sequentially stacked. At this time.
  • PVD physical vapor deposition
  • a metal or conductive metal oxide or alloy thereof is deposited on a substrate to form an anode.
  • It may be prepared by forming an organic material layer including a hole injection filler, a hole transport layer, a light emitting bug and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • the organic material layer from the negative electrode material on the substrate.
  • An anode material may be sequentially deposited to make an organic light emitting device.
  • 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 manufacturing an organic light emitting device.
  • the solution coating method is spin coating. Deep coating. Doctor Blading, Inkjet Printing, Screen Printing. Spray method means roll coating etc., but it is not limited to these.
  • the organic material layer from the negative electrode on the substrate may be manufactured by sequentially depositing an anode material (W0 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode.
  • the second electrode is a cathode, or the first electrode is a cathode.
  • the second electrode is an anode.
  • As the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • Specific examples of the positive electrode material include bark crops. Copper zinc. Metals such as gold or alloys thereof; Zinc Oxide, Indium Oxide ⁇ Tin Oxide (IT0).
  • Metal oxides such as indium zinc oxide (IZ0); A combination of a metal and an oxide such as? ⁇ 0: A 1 or SN 0 2 : Sb; Poly (3-methylthiophene), poly [3,4- (ethylene ⁇ 1,2—deoxy) thiophene] £ 0 0, polypy and Conductive polymers such as polyaniline; It is not limited only to these. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material may include magnesium. calcium . Sodium, potassium. titanium . Indium, yttrium. Lithium. Gadolinium, aluminum. Metals such as 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.
  • IZ0 indium zinc oxide
  • a combination of a metal and an oxide such as? ⁇ 0: A 1 or SN 0 2
  • the hole injection worm is a layer for injecting holes from the electrode.
  • As the hole injection material it has the ability to transport holes. It has an excellent hole injection effect on the light emitting layer or the light emitting material, and prevents the excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material. Also. Compounds excellent in thin film formation ability are preferred. It is preferable that the H0M0 (highest occupied molecuorartal) of the hole injection material be between the work function of the positive electrode material and the HOMO of the surrounding organic matter pack.
  • the hole injection material include metals such as metal porphyr, oligothiophene, arylamine-based organic matter, nucleonitrile-nuclear azatriphenylene-based organic matter, and quinacridone-based organic matter.
  • Perylene-based organic materials include anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer for receiving holes from the hole injection layer to transport holes to the light emitting layer.
  • a material for transporting holes from the anode or the hole injection layer to the light emitting layer as a hole transporting material a material having high mobility to holes is suitable.
  • Specific examples include arylamine-based organics. Conductive polymers.
  • 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. Materials having good quantum efficiency with respect to fluorescence or phosphorescence are preferable. As a specific example, 8-he . Doxy-quinoline aluminum complex (A lq 3 ); Carbazole series compounds; Dimerized styryl compounds: BAl q; 10-hydroxybenzoquinoline-metal compound; Benzoxazole.
  • 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. Specifically, as the condensed aromatic ring derivative, an anthracene derivative. Pyrene derivatives. Naphthalene derivatives, pentacene derivatives. Phenanthrene compound.
  • Fluoranthene compounds and the like, and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds and pyrimidine derivatives. It is not limited to this.
  • Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, and boron complexes. Fluoranthene compound. Metal complexes; Specifically, the aromatic amine derivative may be a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group. Pyrene having an arylamino group.
  • styrylamine Styryldiamine, styryltriamine, styryltetraamine and the like. It is not limited to this. Also. Iridium complexes as metal complexes.
  • the electron transport layer is from the electron injection layer .
  • electrons are well injected from a cathode and can be transferred to a light emitting layer.
  • Materials with high mobility for the electron are suitable. Specific examples include A 1 complex of 8—hydroxyquinoline; Complexes including A lq 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 in accordance with the prior art. Especially.
  • cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium. Ytterbium and samarium, followed by a layer of aluminum or silver in each case.
  • the electron injection layer is a layer for injecting electrons from the electrode. It has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting device or the light emitting material.
  • generated in the light emitting layer to the hole injection layer, and is excellent in thin film formation ability is preferable.
  • fluorenone anthracenodimethane, diphenoquinone, thiopyran dioxide, oxazole oxadiazole.
  • Triazole imidazole, perylenetetracarboxylic acid.
  • the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper and bis (8-hydroxyquinolinato) manganese.
  • 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. Also.
  • the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. 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. [Production example]
  • A1 A2 compound AK30 g, 88 mmol) bis (pinacolato) diboron (24.6 g. 97 mmol). Potassium acetate (25.9 g, 264 mmol). Bi (tritrinusilylphosphino) palladium biacetate (0) [Pd (OAc) 2 (PCy 3 ) 2 ] (2.1 g, 3 moH) was placed in dioxane (200 niL) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then distilled under reduced pressure to remove the solvent. This was dissolved in chloroform, washed three times with water, and then the organic layer was separated and dried over magnesium sulfate. This was distilled under reduced pressure to obtain 3.5 g of Compound A2C3. Yield 88%; MS: [M + H] + 433) was prepared.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1.300 A was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned. At this time. Fischer Co. product was used as a detergent, and distilled water filtered secondly was used as a filter of Millipore Co. product. After washing ⁇ for 30 minutes, the ultrasonic washing was performed for 10 minutes by repeating the dilution with 2 distilled water. After the distilled water wash. Isopropyl alcohol, acetone. Ultrasonic washing with a solvent of methanol, drying and transporting to a plasma cleaner. The substrate was cleaned for 5 minutes using an oxygen plasma and then transported to a vacuum evaporator.
  • ITO indium tin oxide
  • a hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 50 A on the IT0 transparent electrode prepared as described above. The vacuum injection of the following HT-1 compound to a thickness of 250A on the hole injection filling to form a hole transport layer. The HT-2 compound was vacuum deposited to a thickness of 50 A on the HT-1 deposited film to form an electron blocking layer. Compound 1 prepared in Synthesis Example 1 and the following YGD 1 compound, which is a phosphorescent dopant, 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 400 A.
  • ET-1 compound was vacuum deposited to a thickness of 250 A on the light emitting layer, and the following ET-2 compound 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.
  • Aluminum maintained a deposition rate of 2 A / sec.
  • the degree of vacuum was maintained at 1 ⁇ 10 ⁇ 7 to 5 10 ⁇ 3 torr.
  • the driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm 2 , and the time at which the organic light-emitting device became 95% of the initial luminance at a current density of 50 niA / cni 2 (LT95). was measured. The results are shown in the table below.
  • I0 Indium tin oxide
  • IT0 is a thin-coated glass substrate (corning 7059 glass) with a thickness of ⁇ , ⁇ .
  • the dispersant was put in dissolved distilled water and washed with ultrasonic waves. Fischer Co. products were 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. The ultrasonic washing was repeated 10 minutes with distilled water twice. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • a hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 500 A on the prepared ⁇ transparent electrode.
  • the host HI and the dopant D1 compound were vacuum deposited to a thickness of 300A at a weight ratio of 97.5: 2.5.
  • the following compound ET-A was vacuum deposited to a thickness of 50 A on the emission layer to form an electron transport layer.
  • Compound 1 and LiQ (Lithium Quinolate) prepared in Synthesis Example 1 were vacuum deposited on the electron transport layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 350A.
  • Lithium fluoride (LiF) and aluminum at a thickness of 2.000 A were sequentially deposited on the electron injection and transport layer to form a cathode.
  • CE3 CE4 In the above experimental examples and comparative examples, the driving voltage and the luminous efficiency of the organic light emitting diode were measured at a current density of 10 mA / cm 2 , and the time at which the initial luminance was 95% of the initial luminance at a current density of 50 mA / cm 2 (LT95) was measured. The results are shown in Table 2 below.
  • hole injection layer 6 hole transport insect 7: light emitting layer 8: electron transport layer

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  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le comprenant.
PCT/KR2018/002853 2017-03-10 2018-03-09 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant Ceased WO2018164545A1 (fr)

Priority Applications (1)

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CN201880002742.4A CN109415351B (zh) 2017-03-10 2018-03-09 新型杂环化合物及利用其的有机发光元件

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KR20170030565 2017-03-10
KR10-2017-0030565 2017-03-10
KR10-2018-0027923 2018-03-09
KR1020180027923A KR102034196B1 (ko) 2017-03-10 2018-03-09 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자

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WO2018164545A1 true WO2018164545A1 (fr) 2018-09-13

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160006633A (ko) * 2014-07-09 2016-01-19 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 소자
WO2016024745A2 (fr) * 2014-08-12 2016-02-18 삼성에스디아이 주식회사 Composé, diode optoélectronique organique comprenant ledit composé et dispositif d'affichage
CN105384759A (zh) * 2015-10-22 2016-03-09 北京拓彩光电科技有限公司 芳香杂环衍生物和使用该化合物的有机发光二极管器件
KR20160107975A (ko) * 2015-03-06 2016-09-19 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
US20170054087A1 (en) * 2015-08-17 2017-02-23 Universal Display Corporation Organic electroluminescent materials and devices

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160006633A (ko) * 2014-07-09 2016-01-19 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 소자
WO2016024745A2 (fr) * 2014-08-12 2016-02-18 삼성에스디아이 주식회사 Composé, diode optoélectronique organique comprenant ledit composé et dispositif d'affichage
KR20160107975A (ko) * 2015-03-06 2016-09-19 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
US20170054087A1 (en) * 2015-08-17 2017-02-23 Universal Display Corporation Organic electroluminescent materials and devices
CN105384759A (zh) * 2015-10-22 2016-03-09 北京拓彩光电科技有限公司 芳香杂环衍生物和使用该化合物的有机发光二极管器件

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