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WO2010114264A2 - 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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Publication number
WO2010114264A2
WO2010114264A2 PCT/KR2010/001897 KR2010001897W WO2010114264A2 WO 2010114264 A2 WO2010114264 A2 WO 2010114264A2 KR 2010001897 W KR2010001897 W KR 2010001897W WO 2010114264 A2 WO2010114264 A2 WO 2010114264A2
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substituent
alkyl
ring
aryl
fused
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PCT/KR2010/001897
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WO2010114264A3 (fr
Inventor
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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Publication of WO2010114264A2 publication Critical patent/WO2010114264A2/fr
Publication of WO2010114264A3 publication Critical patent/WO2010114264A3/fr

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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
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • 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
    • 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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • 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

Definitions

  • the present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices including the same.
  • the organic electroluminescent compounds according to the present invention are represented by Chemical Formula 1 :
  • ring A and ring B independently represent a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- or 6-membered heteroaromatic ring fused with an aromatic ring, a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring; excluding the case that both the ring A and the ring B are monocyclic aromatic rings.
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • 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].
  • an 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 luminescence 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.
  • host material is very important. Some requirements of the host material that acts as solid solvent and energy transferor include high purity and adequate molecular weight allowing vacuum deposition. Further, high glass transition temperature and pyrolysis temperature are required for good thermal stability and high electrochemical stability is required for long operation life. In addition, formation of an amorphous thin film should be easy and adhesivity with adjacent layers should be good, but with no interlay er migration.
  • CBP 4,4'-N,N'-dicarbazolebiphenyl
  • BAIq 4,4'-N,N'-dicarbazolebiphenyl
  • an object of the present invention is to provide an organic electroluminescent compound having luminescence 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 luminescence efficiency and excellent color purity and life property, it may be used to manufacture an OLED device having very superior operation life.
  • ring A and ring B independently represent a monocyclic or poly cyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- or 6-membered heteroaromatic ring fused with an aromatic ring, a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring; excluding the case that both the ring A and the ring B are monocyclic aromatic rings; and
  • the hydrogen atom of the ring A or the ring B may be further substituted by deuterium.
  • 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 " (C 1 -C30)alkyl, tri(C 1 -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 alkyl 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.
  • the phrase "with or without substituent(s)” means that the substituents of R 1 through R 3 and R 11 through R 18 may be independently substituted with one or more substituent(s) selected from a group consisting of deuterium, halogen, (Cl-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)aryl
  • the organic electroluminescent compound according to the present invention which is represented by Chemical Formula 1, includes the organic electroluminescent compounds represented by Chemical Formulas 2 to 6:
  • B 1 through B 6 independently represent CR 3 or N;
  • each R 3 may be linked via
  • the organic electroluminescent compound according to the present invention may be selected from the following compounds, but is not limited thereto: [47]
  • R 1 is the same as defined in Chemical Formula 1; [61] R 41 through R 44 are the same as defined in Chemical Formulas 2 to 6; and [62] R 45 through R 66 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 sub- stituent(s),(
  • 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 Schemes 1 to 3:
  • 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 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 Formula 7:
  • 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:
  • R2 0 1 through R2 0 3 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 204 through R 219 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), mono- or di-(Cl-C30)alkylamino with or without substituent(s), mono- or di-(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 220 through R 223 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 224 and R 225 independently represent hydrogen, (Cl-C30)alkyl with or without sub- stituent(s), (C6-C30)aryl with or without substituent(s), or halogen, or R 224 and R 225 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 226 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 227 through R 229 independently represent hydrogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen;
  • R 231 through R 242 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 an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring or linked to R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
  • the dopant compound represented by Chemical Formula 7 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.
  • reductive dopant examples 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 luminescence efficiency and excellent color purity and life property, it may be used to manufacture an OLED device having very good operation life.
  • 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 1O 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. Compound 13 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and (piq) 2 Ir(acac) was added in another cell as a dopant. 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 electroluminescent material used in the OLED device had been purified by vacuum sublimation at 10 6 torr.
  • a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding CBP as an electroluminescent host material in another cell of the vacuum deposition apparatus, and adding (piq) 2 Ir(acac) 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).
  • BAIq was deposited with a thickness of 5 nm on the electroluminescent layer as a hole blocking layer, and AIq was deposited with a thickness of 20 nm as an electron transport layer. Then, after depositing Liq with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
  • 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)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (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 dispositifss organiques électroluminescents les utilisant. Les composés selon l'invention ayant un rendement lumineux élevé ainsi qu'une pureté de couleurs et une durée de vie excellentes, on peut les utiliser pour la fabrication de diodes organiques électroluminescentes à excellente durée de vie de fonctionnement.
PCT/KR2010/001897 2009-03-31 2010-03-29 Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant WO2010114264A2 (fr)

Applications Claiming Priority (2)

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KR10-2009-0027256 2009-03-31
KR1020090027256A KR101603070B1 (ko) 2009-03-31 2009-03-31 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자

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Cited By (94)

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EP2292601A1 (fr) * 2009-09-04 2011-03-09 Samsung Mobile Display Co., Ltd. Phenanthro[2,3-b]pyrroles et Phenanthro[3,2-b]pyrroles pour dispositifs électroluminescents organiques
EP2308843A1 (fr) * 2009-10-09 2011-04-13 Samsung Mobile Display Co., Ltd. Composé cyclique condensé et diode électroluminescente organique dotée d'une couche organique l'incluant
WO2011068204A1 (fr) * 2009-12-03 2011-06-09 Jnc株式会社 Composé benzo[c]carbazole avec noyau pyridine portant un substituant et élément électroluminescent organique
US20120012826A1 (en) * 2010-07-13 2012-01-19 Samsung Mobile Display Co., Ltd. Organic light-emitting device
US20120097929A1 (en) * 2010-10-25 2012-04-26 Samsung Mobile Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
EP2447250A1 (fr) * 2010-10-26 2012-05-02 Samsung Mobile Display Co., Ltd. Dispositif électroluminescent organique
CN102452974A (zh) * 2010-10-26 2012-05-16 三星移动显示器株式会社 有机发光装置
JP2012092098A (ja) * 2010-10-26 2012-05-17 Samsung Mobile Display Co Ltd 有機発光素子
WO2012073541A1 (fr) * 2010-12-03 2012-06-07 Jnc株式会社 COMPOSÉ BENZO[c]CARBAZOLE AYANT UN SUBSTITUANT À TENEUR EN PYRIDINE ET ÉLÉMENT ÉLECTROLUMINESCENT ORGANIQUE
WO2012150826A1 (fr) * 2011-05-03 2012-11-08 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif électroluminescent organique les utilisant
WO2013015144A1 (fr) * 2011-07-22 2013-01-31 Semiconductor Energy Laboratory Co., Ltd. Composé dibenzo[c,g]carbazole, élément électroluminescent, dispositif électroluminescent, dispositif d'affichage, dispositif d'éclairage et dispositif électronique
US8384074B2 (en) 2010-04-06 2013-02-26 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
WO2013027565A1 (fr) * 2011-08-22 2013-02-28 ユーディーシー アイルランド リミテッド Élément électroluminescent organique, matériau pour cet élément, dispositif luminescent mettant en œuvre cet élément, dispositif d'affichage, et dispositif d'éclairage
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