WO2011081429A2 - Composé organique et dispositif électroluminescent organique l'utilisant - Google Patents

Composé organique et dispositif électroluminescent organique l'utilisant Download PDF

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WO2011081429A2
WO2011081429A2 PCT/KR2010/009474 KR2010009474W WO2011081429A2 WO 2011081429 A2 WO2011081429 A2 WO 2011081429A2 KR 2010009474 W KR2010009474 W KR 2010009474W WO 2011081429 A2 WO2011081429 A2 WO 2011081429A2
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substituted
unsubstituted
compound
organic
alkyl
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WO2011081429A3 (fr
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신창주
홍진석
김태형
김경수
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주식회사 두산
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    • 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
    • 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
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • 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
    • 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
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, a compound having one or more fluoranthene derivative moieties and having a symmetric or asymmetric molecular structure, and the compound Applied to an organic electroluminescent device, preferably applied as a hole injection layer material, a hole transport layer material, a host material of a fluorescent or phosphorescent layer, an electron injection layer material and / or an electron transport layer material, luminous efficiency, brightness, thermal stability, drive voltage
  • the present invention relates to an organic electroluminescent device having improved characteristics, such as lifespan.
  • organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material. That is, when the organic layer is positioned between the anode and the cathode and a voltage is applied between the two electrodes, holes are injected into the organic layer and electrons are injected into the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground, they shine.
  • Organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') are self-luminous display devices, and thus have excellent contrast ratio, wide viewing angle, and fast response time, which are suitable for high performance displays.
  • an organic EL device has a thin film multilayer structure in which an anode is formed on a substrate and a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially formed on the anode. It is.
  • the reason why the organic EL device is manufactured in a multi-layer is that the movement speeds of the holes and the electrons are different. Therefore, if the appropriate hole injection layer, the transport layer, the electron transport layer, and the injection layer are made, the holes and the electrons can be effectively transferred. This is because the light emission efficiency can be improved by balancing the electrons.
  • Electrons injected from the electron injection layer and holes transferred from the hole injection layer recombine in the emission layer to form excitons, and fall from the singlet excited state to the ground state and are called fluorescence, and fall from the triplet excited state to the ground state.
  • Luminescence is called phosphorescence. Theoretically, when the exciton is generated when the carrier is recombined in the emission layer, the ratio of singlet and triplet excitons is generated at a ratio of 1: 3, and when phosphorescence is used, the internal quantum efficiency may be 100%.
  • TPBI published by Kodak in 1996 and described in US Pat. No. 5,645,948, is known as a representative electron transporting material with imidazole groups, whose structure is three N-phenyl benzimides at the 1,3,5 position of benzene. It is reported that not only the ability to transfer the electrons and functionally block the holes coming from the light emitting layer that contains the sol, but has a low thermal stability to be applied to the actual device.
  • Carbazole ring compounds such as CBP (4,4-dicarbazolybiphenyl) are used as the phosphorescent host material, and metal complex compounds containing heavy atoms such as Ir and Pt are widely used as phosphorescent guest materials.
  • CBP which is currently used phosphorescent host material
  • Tg glass transition temperature
  • an object of the present invention is to apply the organic EL device as 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 to lower the driving voltage, and to reduce luminous efficiency, luminance and thermal properties. It is to provide a novel compound comprising a fluoranthene derivative structure that can improve the stability and device life.
  • Another object of the present invention is to provide an organic EL device using the compound.
  • 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 L is each independently selected from the group consisting of CA 1 A 2 , NA 3 , O, S and SiA 4 A 5 , and A 1 to A 5 are each 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 heteroatoms Alkyl, (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
  • 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, so that when adopted as a blue, green or red fluorescent or phosphorescent host material, low power, high efficiency, high brightness and improved durability And 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.
  • FIG. 1 is a schematic cross-sectional view of an organic EL device according to an embodiment of the present invention.
  • the compound represented by Formula 1 according to the present invention is a compound having one or more fluoranthene derivative moieties and having a symmetric or asymmetric molecular structure, and includes a phosphorescent host material, a fluorescent host material, a hole injection material, and a hole transporting material. It can be used in organic EL devices as materials, electron injection materials and / or electron transport materials.
  • R 1 to R 17 are each independently Where n and m are each independently an integer from 0 to 10, except that at the same time 0; At least one L is each independently selected from the group consisting of CA 1 A 2 , NA 3 , O, S and SiA 4 A 5 , and A 1 to A 5 are each 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 heteroatoms Alkyl, C1-C40 alkyl (substituted or unsubstituted with C6-C60 aryl), substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 arylamine,
  • 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, C1-C20 alkyl (substituted with substituted or unsubstituted C6-C20 aryl), substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 arylamine, substituted or unsubstituted C6-C20 diarylamine, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, substituted Or unsubstituted 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, C1-C20 alkyl, C6-C20 aryl, C6-C20 arylamine, C6-C20 diarylamine, heteroaryl having 5 to 30 nuclear atoms It may be substituted with one or more substituents selected from the group consisting of a condensed polycyclic aromatic hydrocarbon having 5 to 30 nuclear atoms, and a condensed polycyclic aromatic heterocycle having 5 to 30 nuclear atoms. These substituents may be further substituted with C6-C20 aryl, heteroaryl having 5 to 30 nuclear atoms, and the like
  • 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 one another. Site, and non-limiting examples thereof include indene, 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 20, 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 injection 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 is included in the organic EL device as a blue, green, and / or red phosphorescent host, fluorescent host, hole transport material, hole injection material, electron injection material and / or electron transport material. Can be.
  • the compound of formula 1 of the present invention may be 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, hole injection layer, At least one of the hole transport layer, the electron injection layer, and the electron transport layer may include a compound represented by Chemical Formula 1.
  • 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.
  • FIG. 1 A schematic structure of an organic EL device according to an embodiment of the present invention is shown in FIG. Referring to FIG. 1, the substrate 101, the anode 102, the hole injection layer 103, the hole transport layer 104, the light emitting layer 105, the electron transport layer 106, and the cathode 107 are sequentially stacked. .
  • the obtained solution was put into 500 ml of distilled water, and the resulting solid was washed several times with distilled water and then with 200 ml of Methanol to obtain the title compound (3 g, 64%).
  • reaction solution was poured into a 2 L beaker containing ice and hydrochloric acid was slowly added while stirring.
  • the precipitate formed was filtered, washed several times with distilled water and dried to give the title compound (3.5 g, 73%).
  • the compound 8H-indeno [2,1-b] fluoranthene (3 g, 10.32 mmol) synthesized in ⁇ Step 4> was added to a 250 ml round bottom flask, and dried in vacuo and charged with nitrogen gas. 100 ml THF was placed in the flask and cooled to -78 ° C. n-Butyllithium (1.6M in Hex.) (1.65 g, 25.8 mmol) was added slowly and stirred for 1 hour at the same temperature. Iodomethane (4.74 g, 25.8 mmol) was added and stirred for 3 hours.
  • the mixed solution was stirred at 80 ° C. for 12 hours, and then 200 ml of distilled water was added, and the resulting solid was filtered and dissolved in 100 ml of MC, followed by Silicagel Filter. The filtrate was concentrated and then recrystallized from Methanol / Methylene Chloride to give the title compound (5.3 g, 85%).
  • 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 cleaning 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 depositor.
  • ITO Indium tin oxide
  • NPB (40 nm) / each compound synthesized in Synthesis Examples 1-6 + 10% Ir (piq) 2 (acac) (20 nm) / BCP (10 nm) / Alq 3 (40 nm) / LiF ( An organic EL device was manufactured in the order of 1 nm) / Al (200 nm).
  • An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used as a light emitting host material, instead of the compound prepared in Synthesis Example, to form an emission layer.
  • Example 1-6 For each organic EL device manufactured in Example 1-6 and Comparative Example 1, the driving voltage, current efficiency, and luminance were measured, and the results are shown in Table 1 below.
  • the organic EL device (Example 1-6) using the compound according to the present invention exhibits superior performance in terms of voltage and efficiency than the organic EL device (Comparative Example 1) using the conventional CBP. Able to know.
  • DS-HIL Doosan Corporation, hereinafter referred to as DS-HIL
  • DS-HIL was thermally vacuum deposited to a thickness of 60 nm to form a hole injection layer.
  • N N -di (naphthalene-1-yl) -N and N -diphenylbenzidine
  • ADN di (naphthalen-2-yl) anthracene
  • DS-405 Doosan Corporation
  • the organic EL device (Example 7-9) using the compound according to the present invention showed superior performance in terms of voltage and efficiency than the organic EL device (Comparative Example 2) using the conventional Alq3. Able to know.
  • Example 2 On the ITO transparent electrode prepared in Example 1, the compound Inv-38 (40 nm) / CBP + 10% Ir (ppy) 2 (acac) (20 nm) / BCP (10 nm) / Alq 3 (40 nm) synthesized in Synthesis Example 7 ) / LiF (1 nm) / Al (200 nm) in order to produce an organic EL device.
  • An organic EL device was manufactured in the same manner as in Example 10, except that NPB was used instead of the compound prepared in the synthesis example in forming the hole injection and transport layer.
  • Example 10 For each organic EL device manufactured in Example 10 and Comparative Example 3, the driving voltage, current efficiency, and luminance were measured, and the results are shown in Table 3 below.

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Abstract

La présente invention concerne un nouveau composé organique, et un dispositif électroluminescent organique l'utilisant, et plus spécifiquement, un composé ayant une ou plusieurs fractions dérivées du fluoranthène et ayant une structure moléculaire symétrique ou asymétrique, et un dispositif électroluminescent organique ayant des propriétés améliorées de rendement lumineux, luminance, stabilité thermique, tension de commande, durée de vie et similaires par l'application du composé, de préférence à un matériau de couche d'injection de trous, un matériau de couche de transport de trous, un matériau hôte d'une couche fluorescente ou d'une couche phosphorescente, et un matériau de transport et d'injection d'électrons.
PCT/KR2010/009474 2009-12-30 2010-12-29 Composé organique et dispositif électroluminescent organique l'utilisant WO2011081429A2 (fr)

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WO2014192950A1 (fr) * 2013-05-31 2014-12-04 出光興産株式会社 Composé de fluoranthène condensé, matériau d'élément électroluminescent organique comprenant ce composé, élément électroluminescent organique utilisant ce matériau et dispositif électronique
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003272863A (ja) * 2002-03-14 2003-09-26 Mitsui Chemicals Inc 有機電界発光素子
JP2008115131A (ja) * 2006-11-07 2008-05-22 Mitsubishi Chemicals Corp 有機化合物、電荷輸送材料、電荷輸送材料用組成物および有機電界発光素子
KR20080047210A (ko) * 2006-11-24 2008-05-28 삼성전자주식회사 유기 발광 화합물 및 이를 구비한 유기 발광 소자
KR20080047209A (ko) * 2006-11-24 2008-05-28 삼성전자주식회사 유기 발광 화합물 및 이를 구비한 유기 발광 소자

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003272863A (ja) * 2002-03-14 2003-09-26 Mitsui Chemicals Inc 有機電界発光素子
JP2008115131A (ja) * 2006-11-07 2008-05-22 Mitsubishi Chemicals Corp 有機化合物、電荷輸送材料、電荷輸送材料用組成物および有機電界発光素子
KR20080047210A (ko) * 2006-11-24 2008-05-28 삼성전자주식회사 유기 발광 화합물 및 이를 구비한 유기 발광 소자
KR20080047209A (ko) * 2006-11-24 2008-05-28 삼성전자주식회사 유기 발광 화합물 및 이를 구비한 유기 발광 소자

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WO2014157574A1 (fr) * 2013-03-27 2014-10-02 出光興産株式会社 Composé de fluoranthène condensé, matière pour un élément électroluminescent organique utilisant ce composé, élément électroluminescent organique utilisant cette matière et dispositif électronique
US9419226B2 (en) 2013-03-27 2016-08-16 Idemitsu Kosan Co., Ltd. Condensed fluoranthene compound, material for organic electroluminescent element using this compound, organic electroluminescent element using this material, and electronic device
KR20160092059A (ko) 2013-03-27 2016-08-03 이데미쓰 고산 가부시키가이샤 축합 플루오란텐 화합물, 이것을 이용한 유기 전기발광 소자용 재료, 및 이것을 이용한 유기 전기발광 소자 및 전자 기기
KR20150108813A (ko) 2013-03-27 2015-09-30 이데미쓰 고산 가부시키가이샤 축합 플루오란텐 화합물, 이것을 이용한 유기 전기발광 소자용 재료, 및 이것을 이용한 유기 전기발광 소자 및 전자 기기
JP2015180643A (ja) * 2013-03-27 2015-10-15 出光興産株式会社 縮合フルオランテン化合物、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器
JP5802862B2 (ja) * 2013-03-27 2015-11-04 出光興産株式会社 縮合フルオランテン化合物、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器
KR101838833B1 (ko) 2013-03-27 2018-04-26 이데미쓰 고산 가부시키가이샤 축합 플루오란텐 화합물, 이것을 이용한 유기 전기발광 소자용 재료, 및 이것을 이용한 유기 전기발광 소자 및 전자 기기
US9741943B2 (en) 2013-03-27 2017-08-22 Idemitsu Kosan Co., Ltd. Condensed fluoranthene compound, material for organic electroluminescent element using this compound, organic electroluminescent element using this material, and electronic device
JPWO2014157574A1 (ja) * 2013-03-27 2017-02-16 出光興産株式会社 縮合フルオランテン化合物、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器
WO2014192950A1 (fr) * 2013-05-31 2014-12-04 出光興産株式会社 Composé de fluoranthène condensé, matériau d'élément électroluminescent organique comprenant ce composé, élément électroluminescent organique utilisant ce matériau et dispositif électronique
JPWO2014192950A1 (ja) * 2013-05-31 2017-02-23 出光興産株式会社 縮合フルオランテン化合物、これを含む有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器
KR20160014613A (ko) 2013-05-31 2016-02-11 이데미쓰 고산 가부시키가이샤 축합 플루오란텐 화합물, 이것을 포함하는 유기 전기발광 소자용 재료, 및 이것을 이용한 유기 전기발광 소자 및 전자 기기
US10205099B2 (en) 2013-05-31 2019-02-12 Idemitsu Kosan Co., Ltd. Condensed fluoranthene compound, organic electroluminescence element material including same, organic electroluminescence element using same, and electronic device
CN104513246A (zh) * 2013-09-30 2015-04-15 北京鼎材科技有限公司 一种蒽并双咔唑衍生物及其应用
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CN104649956B (zh) * 2013-12-02 2016-04-27 固安鼎材科技有限公司 一种芴并咔唑衍生物及其在有机电致发光器件中的应用
US11618722B2 (en) 2016-11-09 2023-04-04 Idemitsu Kosan Co., Ltd. Compound, composition, organic electroluminescent element, and electronic appliance
CN108623479A (zh) * 2017-03-17 2018-10-09 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和应用
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