WO2010114262A2 - Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant - Google Patents

Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant Download PDF

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WO2010114262A2
WO2010114262A2 PCT/KR2010/001895 KR2010001895W WO2010114262A2 WO 2010114262 A2 WO2010114262 A2 WO 2010114262A2 KR 2010001895 W KR2010001895 W KR 2010001895W WO 2010114262 A2 WO2010114262 A2 WO 2010114262A2
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substituent
alkyl
aryl
organic electroluminescent
halogen
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WO2010114262A3 (fr
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Hyo Nim Shin
Chi Sik Kim
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Dow Advanced Display Materials,Ltd.
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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
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • C—CHEMISTRY; METALLURGY
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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
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    • C09K2211/1011—Condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic 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
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • 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
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Definitions

  • the present invention relates to a novel compound for organic electronic material and an organic electronic device including the same. More specifically, the organic electroluminescent compound according to the present invention is represented by Chemical Formula 1 :
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • EL electroluminescent
  • Eastman Kodak first developed an organic EL device using low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
  • organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired to form an exciton. As the exciton is deactivated, light is emitted by phosphorescence or fluorescence.
  • An organic EL device emits polarized light with high luminance of about 100-10,000 cd/m 2 at a voltage of about 10 V. It can emit light in the spectrum from blue to red by simply selecting different fluorescent materials.
  • the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power and provides excellent color.
  • electroluminescent material In an organic EL device, the most important factor that determines its performance including luminous efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • Organic electroluminescent materials may be roughly classified into high- molecular- weight materials and low-molecular- weight materials.
  • the low- molecular- weight materials may be classified into metal complexes and metal-free pure organic electroluminescent materials, depending on molecular structure.
  • Chelate complexes such as tris( 8 -quinolato) aluminum, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, or the like are known. It is reported that electroluminescence from blue to red light in the visible region can be obtained using these materials.
  • the electroluminescent materials may be divided into host materials and dopant materials.
  • an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property.
  • development of an organic EL device having high efficiency and long operation life is becoming an imminent task.
  • development of materials which are much superior to existing electroluminescent materials is urgently needed.
  • the inventors of the present invention invented novel electroluminescent compounds capable of realizing an organic electroluminescent device with excellent luminous efficiency and remarkably improved operation life.
  • an object of the present invention is to provide an organic electroluminescent compound having luminous efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates.
  • Another object of the present invention is to provide an organic electronic device with high efficiency and long operation life, employing the organic electroluminescent compound as an electroluminescent material.
  • the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electronic device including the same. Since the organic electroluminescent compound according to the present invention has superior luminous efficiency and excellent life property, it may be used to manufacture an OLED device having very superior operation life.
  • [24] L is selected from the following structures:
  • Ri through R 6 , R 3 i through R 44 , Ar 1 and Ar 2 independently represent hydrogen, deuterium, halogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without sub- stituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adam
  • Rn through R 13 are the same as defined in R 1 through R 6 ;
  • m represents an integer 1 or 2;
  • alkyl include both linear and branched species.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s).
  • Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1 -naphthyl and 2-naphthyl
  • the anthryl includes 1 -anthryl, 2-anthryl and 9-anthryl
  • the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isoben- zofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, ben- zoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quino
  • the alkyl moiety of "(Cl-C30)alkyl, tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (Cl-C30)alkyloxy, (C 1 -C30)alkylthio, (C 1 -C30)alkyloxycarbonyl, (C 1 -C30)alkylcarbonyl, (Cl-C30)alkyloxycarbonyloxy or (Cl-C30)alkylcarbonyloxy" may have 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the aryl moiety of "(C6-C30)aryl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C6-C30)arylcarbonyloxy or (C6-C30)aryloxycarbonyloxy" may have 6 to 30 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the "(C3-C30)heteroaryl” may have 3 to 30 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the "(C3-C30)cycloalkyl” may have 3 to 30 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the "(C2-C30)alkenyl or alkynyl” may have 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
  • [40] L may be selected from the following structures, but is not limited thereto:
  • R 1 through R 6 and R 31 through R 37 are independently the same as defined in Chemical Formula 1.
  • R 1 through R 6 and R 31 through R 37 are independently the same as defined in Chemical Formula 1.
  • R 31 through R 38 independently represent (Cl-C30)alkyl with or without sub- stituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring.
  • organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but the following compounds do not limit the present invention:
  • organic electroluminescent compound according to the present invention may be prepared by Scheme 1 :
  • the present invention provides an organic electroluminescent device including a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode.
  • the organic layer includes one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
  • the organic electroluminescent compound is used as a host material of an electroluminescent layer.
  • the organic layer may include an electroluminescent layer which further includes one or more dopant(s) in addition to one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
  • the dopant used in the organic electronic device of the present invention is not particularly limited.
  • the dopant used in the organic electronic device of the present invention is selected from the compounds represented by Chemical Formulas 2 to 4:
  • each of Ri 0I through Ri 2 o may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;
  • Ri 2 i through R 125 independently represent hydrogen, deuterium, halogen,
  • (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without sub- stituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered hete- rocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adamantyl with or without substituent(s), (C7-C30)bicycloalkyl with or without substituent(s), cyano, NR 61 R 62 , BR 63 R 64 , PR 65 R 66 , P( O)R 67 R 68 [wherein R 61 through R
  • M 1 is selected from a group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals;
  • the ligands L 101 , L 102 and L 103 are independently selected from the following structures:
  • Ri 3 i through Ri 33 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (Cl-C30)alkyl substituent(s), or halogen;
  • R 134 through R 149 independently represent hydrogen, (Cl-C30)alkyl with or without substituent(s), (Cl-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (Cl-C30)alkylamino with or without sub- stituent(s), (C6-C30)arylamino with or without substituent(s), SF 5 , tri(Cl-C30)alkylsilyl with or without substituent(s), di(Cl-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
  • R 150 through R 153 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (Cl-C30)alkyl substituent(s);
  • R 154 and R 155 independently represent hydrogen, (Cl-C30)alkyl with or without sub- stituent(s), (C6-C30)aryl with or without substituent(s), or halogen, or R 154 and R 155 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or poly cyclic aromatic ring;
  • R 156 represents (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), or halogen;
  • R 157 through R 159 independently represent hydrogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen;
  • Ri 6 i through R 172 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s), (Cl-C30)alkoxy, halogen, (C6-C30)aryl with or without sub- stituent(s), cyano, or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to R 137 or R 138 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
  • the dopant compound represented by Chemical Formulas 2 to 4 may be exemplified by the following compounds, but is not limited thereto:
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) or complex(es) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d- transition elements.
  • the organic layer may include an electroluminescent layer and a charge generating layer.
  • the organic layer may include, in addition to the organic electroluminescent compound, one or more organic electroluminescent layer(s) emitting blue, red and green light at the same time, to provide a white light-emitting organic electroluminescent device.
  • the compounds emitting blue, red or green light are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
  • a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. A driving stability may be attained therefrom.
  • the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be placed on the inner surface of one or both electrode(s) among the pair of electrodes.
  • injection and transport of electrons from the mixed region to the electroluminescent medium becomes easier, because the electron transport compound is reduced to an anion.
  • injection and transport of holes from the mixed region to the electroluminescent medium becomes easier, because the hole transport compound is oxidized to a cation.
  • Preferred examples of the oxidative dopant include various Lewis acids and acceptor compounds.
  • Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
  • a white light-emitting organic electroluminescent device having two or more electroluminescent layers may be prepared by using a reductive dopant layer as the charge generating layer.
  • the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to man- ufacture an OLED device having very good operation life.
  • Example 1 Manufacture of OLED device using the organic electroluminescent compound according to the present invention
  • An OLED device was manufactured using the organic electroluminescent compound of the present invention.
  • a transparent electrode ITO film (15 ⁇ /D) prepared from a glass substrate for an OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
  • the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus.
  • a vacuum deposition apparatus After adding 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 10 ⁇ 6 torr. Then, 2-TNATA was evaporated by applying electrical current to the cell to form a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • NPB ⁇ f,./V-bis( ⁇ -naphthyl)-/V,./V '- diphenyl-4,4'-diamine
  • An electroluminescent layer was formed on the hole transport layer as follows.
  • the compound according to the present invention e.g., Compound 1
  • (piq) 2 Ir(acac) was added in another cell.
  • the two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 4 to 10 wt% based on (piq) 2 Ir(acac).
  • Each OLED electroluminescent used in the OLED device had been purified by vacuum sublimation at 10 6 torr.
  • [218] [219]
  • An OLED device was manufactured in the same manner as Example 1, except for adding CBP as an electroluminescent host material in another cell of the vacuum deposition apparatus instead of the electroluminescent compound according to the present invention.
  • the organic electroluminescent compounds according to the present invention exhibit superior electroluminescence properties as compared to the existing material. Further, the devices wherein the organic electroluminescent compounds according to the present invention are used as host material exhibit decreased driving voltage and power efficiency increased by 1.7-3.2 ImAV. Therefore, power consumption can be reduced.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouveaux composés organiques électroluminescents et des dispositifs organiques électroluminescents les utilisant. Compte tenu du bon rendement lumineux et de l'excellente durée de vie du matériau, les composés selon l'invention peuvent être utilisés dans la fabrication de diodes organiques électroluminescentes à excellente durée de vie de fonctionnement.
PCT/KR2010/001895 2009-03-31 2010-03-29 Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant WO2010114262A2 (fr)

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KR10-2009-0027230 2009-03-31
KR1020090027230A KR20100108909A (ko) 2009-03-31 2009-03-31 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자

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* Cited by examiner, † Cited by third party
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EP2292604A3 (fr) * 2009-08-10 2011-03-30 Samsung Mobile Display Co., Ltd. Composés cycliques condensés et diode électroluminescente organique dotée d'une couche organique les incluant
CN106632446A (zh) * 2016-12-30 2017-05-10 上海升翕光电科技有限公司 一种苯并噻咯类衍生物及其制备方法和有机发光器件
US9748492B2 (en) 2012-11-02 2017-08-29 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2017174414A1 (fr) 2016-04-05 2017-10-12 Bayer Cropscience Aktiengesellschaft Dérivés de naphtaline utilisés comme agents de lutte contre les nuisibles
CN107936014A (zh) * 2017-12-17 2018-04-20 南京科技职业学院 有机发光材料4,6‑二苯基双茚并蒽唑啉的合成方法及应用
WO2018138050A1 (fr) 2017-01-26 2018-08-02 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
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JP2020026406A (ja) * 2018-08-10 2020-02-20 キヤノン株式会社 有機化合物、有機発光素子、表示装置、撮像装置、電子機器、照明装置及び移動体
WO2021057009A1 (fr) * 2019-09-27 2021-04-01 武汉华星光电半导体显示技术有限公司 Matériau de sortie de couplage optique planaire n-hétérocyclique et son procédé de préparation
CN114835699A (zh) * 2022-06-08 2022-08-02 阜阳欣奕华材料科技有限公司 一种蒽并呋喃类化合物、中间体、有机电致发光器件及显示装置

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US10388885B2 (en) 2012-11-02 2019-08-20 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2017174414A1 (fr) 2016-04-05 2017-10-12 Bayer Cropscience Aktiengesellschaft Dérivés de naphtaline utilisés comme agents de lutte contre les nuisibles
CN106632446A (zh) * 2016-12-30 2017-05-10 上海升翕光电科技有限公司 一种苯并噻咯类衍生物及其制备方法和有机发光器件
WO2018138050A1 (fr) 2017-01-26 2018-08-02 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
WO2018186462A1 (fr) * 2017-04-07 2018-10-11 コニカミノルタ株式会社 Composé fluorescent, composition de matériau organique, film électroluminescent, matériau d'élément électroluminescent organique et élément électroluminescent organique
JPWO2018186462A1 (ja) * 2017-04-07 2020-02-27 コニカミノルタ株式会社 蛍光発光性化合物、有機材料組成物、発光性膜、有機エレクトロルミネッセンス素子材料及び有機エレクトロルミネッセンス素子
CN107936014A (zh) * 2017-12-17 2018-04-20 南京科技职业学院 有机发光材料4,6‑二苯基双茚并蒽唑啉的合成方法及应用
JP2020026406A (ja) * 2018-08-10 2020-02-20 キヤノン株式会社 有機化合物、有機発光素子、表示装置、撮像装置、電子機器、照明装置及び移動体
JP7130491B2 (ja) 2018-08-10 2022-09-05 キヤノン株式会社 有機化合物、有機発光素子、表示装置、撮像装置、電子機器、照明装置及び移動体
WO2021057009A1 (fr) * 2019-09-27 2021-04-01 武汉华星光电半导体显示技术有限公司 Matériau de sortie de couplage optique planaire n-hétérocyclique et son procédé de préparation
CN114835699A (zh) * 2022-06-08 2022-08-02 阜阳欣奕华材料科技有限公司 一种蒽并呋喃类化合物、中间体、有机电致发光器件及显示装置

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