WO2011081403A2 - Composé luminescent organique et élément électroluminescent organique comprenant ce composé - Google Patents

Composé luminescent organique et élément électroluminescent organique comprenant ce composé Download PDF

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WO2011081403A2
WO2011081403A2 PCT/KR2010/009415 KR2010009415W WO2011081403A2 WO 2011081403 A2 WO2011081403 A2 WO 2011081403A2 KR 2010009415 W KR2010009415 W KR 2010009415W WO 2011081403 A2 WO2011081403 A2 WO 2011081403A2
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substituted
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aryl
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WO2011081403A3 (fr
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권수진
김태형
김경수
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Doosan Corp
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • 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
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • 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

Definitions

  • the present invention is applied to an organic light emitting compound and the organic electroluminescent device, and preferably applied as a hole injection layer material, a hole transport layer material, a host material of the fluorescent layer or phosphorescent layer, electron transport and injection material, luminous efficiency, brightness, thermal
  • the present invention relates to an organic EL device having improved stability, driving voltage, and lifespan.
  • Organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') have several advantages such as low voltage driving, self-luminous, light weight, wide viewing angle, and fast response time, which will replace LCDs. As one of the flat panel displays, research is being actively conducted in recent years.
  • Tang discloses a two-layered organic EL device in which an organic light emitting medium comprises two organic layers sandwiched between an anode and a cathode. That is, in the organic EL device, the hole transporting layer adjacent to the anode contains a hole transporting material so that only holes are mainly transmitted to the light emitting layer in the organic EL device, and the electron transporting layer adjacent to the cathode is an electron transporting material.
  • the high luminous efficiency was achieved to improve the technology of the organic EL device substantially. Therefore, in terms of light emission efficiency, unless a multilayer system including a hole injection layer, a hole transport layer, and a hole blocking layer is used, it is difficult to expect high efficiency and high luminance emission characteristics. It is true.
  • Tang et al. Use tris (8-hydroxyquinolinol aluminum) as a light emitting layer and a triphenyldiamine derivative as a hole transporting layer.
  • Advantages of the laminated structure include increasing the injection efficiency of holes into the light emitting layer, blocking the electrons injected from the cathode to increase the generation efficiency of excitons generated by recombination, and confining excitons generated in the light emitting layer.
  • the organic EL element of such an example the three-layer type of a hole transport (injection) layer, an electron transport light emitting layer, a hole transport (injection) layer, a light emitting layer, an electron transport (injection) layer, etc. are well known.
  • the device structure and the formation method have been devised.
  • light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. From these, it has been reported that light emission in the visible region from blue to red can be obtained, and thus, the realization of color display elements is expected.
  • chelate complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives
  • a device using a phenylanthracene derivative as a light emitting material is disclosed in Japanese Patent Laid-Open No. 1996-012600.
  • the anthracene derivative is used as a blue light emitting material, the stability of the thin film was required to increase the device life.
  • conventional monoanthrasene derivatives are often crystallized and the thin films are often destroyed, and improvement is required.
  • Japanese Patent Laid-Open No. 2002-154993 discloses a light emitting device using a compound in which anthracene ring and fluorene ring are directly bonded, but does not provide improved light emission uniformity at high temperature.
  • a light emitting material in which spirofluorene is substituted at positions 9 and 10 of anthracene is disclosed (Japanese Patent Laid-Open No. 2002-121547).
  • Japanese Patent Laid-Open No. 2002-121547 Japanese Patent Laid-Open No. 2002-121547.
  • a luminescent material is improved for crystallization, but since it has two spirofluorene skeletons having a large molecular weight, the deposition temperature is very high at 400 ° C.
  • the electric field concentrates on this part, leading to deterioration and destruction of the device.
  • the organic layer is usually used in an amorphous state, and the organic EL element is a current injection type element, if the material used has a low glass transition temperature (Tg), heat generated during use may cause deterioration of the organic EL element. It shortens the life of the device. Thus, materials having a high glass transition temperature are preferred.
  • an object of the present invention is to provide an organic light emitting compound which can be applied as an excellent hole injection layer material, a hole transport layer material, a host material of a fluorescent layer or a phosphorescent layer, an electron transport and injection material, and light emission efficiency, luminance, thermal stability, and driving thereof. It is to provide an organic EL device having improved characteristics such as voltage and lifetime.
  • the present invention to achieve the above object provides a compound represented by the following formula (1).
  • R 1 to R 17 are each independently This,
  • n and m are each independently an integer of 0 to 10, except that at the same time 0;
  • At least one Q is independently hydrogen, deuterium, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3- C40 cycloalkyl, substituted or unsubstituted heterocycloalkyl having 3 to 40 nuclear atoms, (substituted or unsubstituted C6-C60 aryl) C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C6-C60 diarylamine, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted nuclear atom 5 to 60 heteroaryl,
  • R 1 to R 12 may combine with adjacent groups to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring;
  • R 13 and R 14 , R 16 and R 17 may combine with each other to form a cyclic ring.
  • the present invention the anode; cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes the compound described above.
  • the compound of formula 1 according to the present invention may have both fluorescence and phosphorescence properties and has excellent thermal stability, and thus, when adopted as a blue, green, or red fluorescence or phosphorescent host material, low power, high efficiency, high brightness and improved durability Life can be secured.
  • the electron and the hole substituents in the molecule even as a hole injection layer, a hole transport layer, an electron injection layer and / or an electron transport layer material of an organic EL device comprising at least one organic layer between the anode and the cathode Can be applied. Therefore, the organic EL device including the compound of the present invention can be greatly improved in terms of light emitting performance and lifetime, and thus can be effectively applied to a full color display panel and the like.
  • the compound represented by Formula 1 according to the present invention is a compound having at least one phenanthrene derivative moiety, which is a phosphorescent host material, a fluorescent host material, a hole injection material, a hole transport material, an electron injection material and / or an electron transport material It can be used in an organic EL device as a material.
  • a 1 to A 5 are each independently hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted Or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted heterocycloalkyl having 3 to 20 nuclear atoms, (substituted or unsubstituted C6-C30 aryl) C1-C20 alkyl, substituted or unsubstituted C1-C20 Alkoxy, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C6-C30 diarylamine, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted Ring heteroaryl
  • R 1 to R 12 may combine with adjacent groups to form, for example, a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring of 5 to 50 nuclear atoms, and R 13 and R 14 , R 16 and R 17 may be bonded to each other to form a cyclic ring, for example, a cyclic ring having 5 to 8 nuclear atoms.
  • R 1 to R 17 are each independently n is 0 and m is an integer of 1 to 10, preferably 1 to 5 Can be.
  • cyclic aromatic hydrocarbons and the condensed polycyclic aromatic heterocycles are each independently deuterium, halogen, nitrile, nitro, amine, C1-C20 alkyl, C1-C20 alkylamine, C1-C20 alkylsilyl, C6-C30 aryl, (C6 -C30 aryl) C1-C20 alkyl, C1-C20 alkoxy, C6-C30 aryloxy, C6-C30 arylthio, heteroaryl having 5 to 20 nuclear atoms, condensed polycyclic aromatic hydrocarbon having 5 to 20 nuclear atoms, And it may be substituted with
  • an "unsubstituted condensed polycyclic aromatic hydrocarbon” is an aromatic having 5 to 50, preferably 5 to 20, atoms formed by condensation of 5- to 8-membered aromatic rings with each other Moiety, non-limiting examples of which include fluorene, phenanthrene and the like.
  • Unsubstituted condensed polycyclic aromatic heterocycle refers to the condensation of 5- to 6-membered aromatic rings with each other to form an aromatic moiety of 5 to 50, preferably 5 to 20, atomic atoms.
  • an aromatic moiety wherein at least one carbon, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O or S.
  • Non-limiting examples thereof include carbazole and the like.
  • Unsubstituted heterocycloalkyl means a non-aromatic moiety having from 3 to 40, preferably from 3 to 30, nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O or Substituted with a hetero atom such as S.
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • Unsubstituted heteroaryl means a monoheterocyclic or polyheterocyclic aromatic moiety of 5 to 60, preferably 5 to 30, nuclear atoms, wherein at least one carbon, preferably 1 to 3 carbon atoms in the ring Carbon is substituted with a heteroatom such as N, O or S. It is understood that two or more rings may be attached in a simple or fused form to each other and further include a condensed form with an aryl group. In the present invention, heteroaryl and aromatic heterocycle may be used in an overlapping sense.
  • An organic EL device comprises: an anode; Cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer includes a compound represented by Chemical Formula 1.
  • the compound of Formula 1 may be included alone or in plurality.
  • the organic layer including the compound of Formula 1 of the present invention may be at least one of a hole injection layer, a hole transport layer, an electron transport layer, and a light emitting layer.
  • the light emitting layer may include a phosphorescent dopant material or a fluorescent dopant material.
  • the compound of formula 1 of the present invention may be included in the organic EL device as a blue, green, and / or red phosphorescent host, a fluorescent host, a hole transport material, a hole injection material and / or an electron transport material.
  • the compound of formula 1 of the present invention may be a phosphorescent guest material or a fluorescent guest material. More preferably, the compound of formula 1 of the present invention may be included in the organic EL device as a phosphorescent host or a fluorescent host, particularly preferably as a phosphorescent host.
  • the compound of the present invention has a high glass transition temperature of 150 °C or more, when the compound is used as an organic layer of the organic EL device, since the crystallization is minimized in the organic EL device, the driving voltage of the device can be lowered, luminous efficiency, luminance , Thermal stability, and lifetime characteristics can be improved.
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode may be sequentially stacked, wherein the light emitting layer, the hole injection layer, At least one of the hole transport layer and the electron transport layer may include a compound represented by Chemical Formula 1.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic EL device according to the present invention may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic layer.
  • the organic layer including the compound of Formula 1 may be formed by vacuum deposition or solution coating.
  • the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.
  • the organic EL device of the present invention forms an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers is formed to include the compound represented by the formula (1) of the present invention. can do.
  • a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
  • Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer, the electron transport layer and the electron injection layer are not particularly limited, and conventional materials known in the art may be used.
  • 9-bromophenanthrene (20g, 76mmol), o-tolylboronic acid (10.2g, 76mmol), Palladium (II) acetate (0.34g, 0.152mmol), Patassium carbonate (52.4g, 380mmol) and Tertrabutylammonium bromide (48.4g, 150 mmol ) was placed in a flask and dried in vacuo and charged with nitrogen. Distilled water was added thereto, heated to 70 °C and vigorously stirred for two hours.
  • a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After the washing of distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • An organic EL device was manufactured in the same manner as in Example 1, except that 9,10-di- (2-naphthyl) anthracene (ADN) was used as a light emitting host material in place of the compound prepared in the synthesis example when forming the light emitting layer.
  • ADN 9,10-di- (2-naphthyl) anthracene
  • Example 1-5 For each organic EL device manufactured in Example 1-5 and Comparative Example 1, the driving voltage, current efficiency, color coordinates, and luminance were measured, and the results are shown in Table 1 below.
  • the organic EL device using the compound according to the present invention shows superior performance in terms of luminous efficiency and driving voltage than the organic EL device using the conventional ADN.

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  • Optics & Photonics (AREA)
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Abstract

Cette invention concerne un composé luminescent organique et un élément électroluminescent organique comprenant ce composé et, spécifiquement, un tel élément électroluminescent organique possédant des propriétés améliorées en termes de rendement lumineux, de luminance, de stabilité thermique, de tension de commande et de longévité, dans lequel le composé de l'invention est utilisé, de préférence comme matériau de couche d'injection de trous, comme matériau de couche de transport de trous, comme matériau hôte pour une couche fluorescente ou phosphorescente, et/ou comme matériau de transport et d'injection d'électrons.
PCT/KR2010/009415 2009-12-30 2010-12-28 Composé luminescent organique et élément électroluminescent organique comprenant ce composé Ceased WO2011081403A2 (fr)

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KR10-2009-0134543 2009-12-30
KR1020090134543A KR20110077871A (ko) 2009-12-30 2009-12-30 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자

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WO2015033559A1 (fr) * 2013-09-06 2015-03-12 出光興産株式会社 Dérivé d'anthracène et élément électroluminescent organique l'utilisant
WO2015041358A1 (fr) * 2013-09-20 2015-03-26 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
TWI564290B (zh) * 2014-12-30 2017-01-01 機光科技股份有限公司 有機材料及使用此材料之有機電激發光裝置
WO2017104767A1 (fr) * 2015-12-16 2017-06-22 Tdk株式会社 Composé pour élément électroluminescent organique et élément électroluminescent organique l'utilisant
CN111225904A (zh) * 2018-02-28 2020-06-02 株式会社Lg化学 杂环化合物及包含其的有机发光装置
WO2022191299A1 (fr) * 2021-03-10 2022-09-15 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
US11795185B2 (en) 2017-12-13 2023-10-24 Lg Display Co., Ltd. Compound for electron-transport material and organic light emitting diode including the same
KR20260004446A (ko) 2023-04-27 2026-01-08 이데미쓰 고산 가부시키가이샤 화합물, 유기 일렉트로루미네센스 소자, 및 전자 기기

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KR102013400B1 (ko) * 2012-03-29 2019-08-22 에스에프씨 주식회사 인데노페난트렌 유도체 및 이를 포함하는 유기전계발광소자
EP2924029B1 (fr) * 2013-03-15 2018-12-12 Idemitsu Kosan Co., Ltd Dérivé d'anthracène et élément électroluminescent organique l'utilisant
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