WO2006065105A1 - Composes et dispositif d'affichage a electroluminescence organique comportant de tels composes - Google Patents

Composes et dispositif d'affichage a electroluminescence organique comportant de tels composes Download PDF

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WO2006065105A1
WO2006065105A1 PCT/KR2005/004354 KR2005004354W WO2006065105A1 WO 2006065105 A1 WO2006065105 A1 WO 2006065105A1 KR 2005004354 W KR2005004354 W KR 2005004354W WO 2006065105 A1 WO2006065105 A1 WO 2006065105A1
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Jong-Wook Park
Ji-Hoon Lee
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Doosan Corporation
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    • C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
    • H—ELECTRICITY
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • 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
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    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Definitions

  • the present invention relates to compounds for an electroluminescence light-emitting device and an organic electroluminescence display device including the same, and more particularly, to compounds applicable to any one of a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron transport layer (ETL) and an electron injection layer (EIL) of an organic electroluminescence display device and a highly efficient organic electroluminescence display device including the same.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emitting layer
  • ETL electron transport layer
  • EIL electron injection layer
  • Such display devices may be classified into luminescence types and non-luminescence types.
  • a Cathode Ray Tube CRT
  • ELD Electroluminescence Display
  • LED Light Emitting Diode
  • Plasma a plasma
  • Display Panel PDP
  • PDP Display Panel
  • a Liquid Crystal Display (LCD), etc.
  • the luminescence type and non-luminescence type display devices have the same basic characteristics such as working voltage, consumption power, brightness, contrast, response time, lifetime and color display, etc.
  • liquid crystal display devices which have largely been used up till now, have some problems in terms of response time, contrast, and viewing angle among the basic characteristics described above. Displays using a luminescence diode are anticipated as next generation display devices that can solve the problems of liquid crystal displays since they have a much shorter response time, do not require a backlight due to having self-luminescence properties, and they also have improved brightness, etc.
  • An electroluminescence diode has difficulties in application to a large area electroluminescence display device because an inorganic material with crystalline form is mainly used. Furthermore, in the case of an electroluminescence display device using an inorganic material, there are disadvantages that more than 200 V of driving voltage is required and that it is expensive. Active researches on electroluminescence display devices comprising organic materials have been undertaken since the Eastman Kodak Company firstly disclosed a device made from a material having a ⁇ -conjugated molecular structure in 1987. In the case of organic materials, there are advantages that a synthetic pathway is relatively simpler and various forms of materials can be synthesized and thus color tuning is easier. On the contrary, organic materials have disadvantages in that crystallization by heat occurs due to low mechanical strength.
  • Organic materials used in an electroluminescence display device are classified into low molecular organic materials and polymeric materials.
  • diamine diamine derivatives, such as N,N'-bis- (4- methylphenyl)-N,N'-bis(phenyl)benzidine (TPD), etc.
  • TPD N,N'-bis- (4- methylphenyl)-N,N'-bis(phenyl)benzidine
  • perylene tetracarboxylic acid derivatives oxadiazole derivatives, 1 ,1 ,4,4-tetraphenyl-1 ,3-butadiene (TPB), etc.
  • the aspect of the present invention is to provide compounds for an electroluminescence display device that can be applied to any one of a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) of an electroluminescence display device.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emitting layer
  • ETL electron transport layer
  • EIL electron injection layer
  • Another aspect of the present invention is to provide an electroluminescence display device having a low driving voltage, various color developments, and a short response time.
  • the present invention provides monomers represented by the following formulae 1 to 3, oligomers thereof, or polymers thereof for an electroluminescence display device:
  • X 1 to X 6 are independently N or CR' and at least one of Xi and X 2 , at least one of X 3 and X 4 , and at least one of X 5 and X 6 are N 1 where R' is selected from the group consisting of hydrogen, a substituted or unsubstituted linear or branched alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryl, and a substituted or unsubstituted heteroaryl,
  • R 1 to R 18 are independently selected from the group consisting of hydrogen, deuterium, halogen, -CN, -NO 2 , a substituted or unsubstituted linear or branched alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, substituted unsubstituted carbazole, substituted or unsubstituted phenothiazine, substituted or unsubstituted phenoxazine, substituted or unsubstituted phenoxathin, substituted or unsubstituted acridine, substituted or unsubstituted phenazasiline, substituted or unsubstituted 9-aza-IO-germa-anthracene, SiR 19
  • Rig to R 25 are independently selected from the group consisting of hydrogen, a substituted or unsubstituted linear or branched alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryl, and a substituted or unsubstituted heteroaryl.
  • Another aspect of the present invention is to provide an electroluminescence device that includes the above compounds in any one or all of a hole injection layer, a hole transport layer, an electroluminescent layer, an electron transport layer, and an electron injection layer (EIL).
  • EIL electron injection layer
  • FIG. 1 is a schematic view of an organic electroluminescence display device according to the present invention.
  • FIG. 2 shows a UV-Vis spectrum of the compounds of chemical formula 16 according to Example 3.
  • FIG. 3 shows a PL spectrum of the compounds of chemical formula 16 according to Example 3.
  • FIG. 4 shows an EL spectrum of the compounds of chemical formula 16 according to Example 3. DETAILED DESCRIPTION OF THE INVENTION
  • the compounds in accordance with the present invention can be applied to any one of a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and an electron injection layer of an electroluminescence (EL) device.
  • the compounds are monomers represented by the above formulae 1 to 3, oligomers thereof, or polymers thereof.
  • the compounds may be applied as host materials or dopants to a limiting layer due to improved light-emitting properties.
  • the compounds of the present invention for an electroluminescence device include a compound represented by the chemical formulae 1 to 3, or oligomers thereof, or homopolymers or copolymers thereof.
  • X 1 to X 6 are independently N or CR' wherein
  • R' is selected from the group consisting of hydrogen, a unsubstituted linear or branched alkyl, a cycloalkyl, an alkenyl, an alkynyl, an alkoxy, an aryl, and a heteroaryl, and at least one of X 1 and X 2 , at least one of X 3 and X 4 , and at least one of X 5 and X 6 are N.
  • X 1 to X 6 are all nitrogen.
  • Ri to R 18 are independently selected from the group consisting of hydrogen, deuterium, halogen, -CN, -NO 2 , a substituted or unsubstituted linear or branched alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, substituted or unsubstituted carbazole, substituted or unsubstituted phenothiazine, substituted or unsubstituted phenoxazine, substituted or unsubstituted phenoxathin, substituted or unsubstituted acridine, substituted or unsubstituted phenazasiline, substituted or unsubstituted 9-aza-10-germa-anthrac
  • R 26 is selected from the group consisting of hydrogen, a substitute
  • substituted or unsubstituted linear or branched alkyl, cycloalkyl, or alkoxy have C1 to C12 alkyl or alkoxy, and preferably C1 to C7 of a lower alkyl or alkoxy.
  • the cycloalkyl may be preferably a C3 to C12 cycloalkyl, and more preferably a C3 to C8 cycloalkyl.
  • the alkenyl may be preferably a C2 to C8 alkenyl, and more preferably a C2 to C4 alkenyl.
  • the alkynyl may be preferably a C2 to C8 alkynyl, and more preferably a C2 to C4 alkynyl.
  • the aryl may be preferably a C4 to C30 aryl, more preferably a C4 to C20 aryl, and more preferably a C4 to C12 aryl.
  • the heteroaryl may be preferably a C4 to C30 heteroaryl, more preferably a C4 to C20 heteroaryl, and still more preferably a C4 to C12 heteroaryl that includes 1 to 3 heteroatoms, such as N, S, P, or O 1 in an aromatic ring.
  • the substituted alkyl, alkoxy, cycloalkyl, alkenyl, alkynyl, aryl, and heteroaryl means that at least one hydrogen thereof is substituted with an alkyl, a cycloalkyl, an alkoxy, an alkenyl, an alkynyl, an aryl, a heteroaryl, a halogen such as F, Cl, Br or I, aliphatic amine, aromatic amine, or an aryloxy.
  • oligomers, homopolymers, or copolymers prepared from the monomers represented by the chemical formulae 1 to 3 may be used.
  • the oligomers or polymers may be represented by the following formulae 4 (Chemical Formula 4)
  • X 1 to X 6 , R 3 to R 6 , R 9 to R 12 , and R 15 to R 18 are the same as in the above formulae 1 to 3, and n, m, and I are respectively in the range from 1 to 10000, and preferably 1 to 1000. In the case of oligomers, n, m, and I are respectively in the range of 1 to 10, and in the case of polymers, n, m, and I are respectively in the range of 1 to 1000.
  • the oligomers or copolymers may be prepared through a solution polymerization of the monomers of the chemical formulae 1 to 3 using a metal catalyst such as Ni (O), Pd (O), etc.
  • the catalyst may be Ni(COD) 2 [Bis (1 ,5- cyclooctadiene)nickel (O)], Pd(Ph 3 J 4 (tetrakis(triphenylphosphine)palladium(O)),
  • PdCI 2 palladium (II) chloride
  • FeCI 3 iron (III) chloride
  • the compound may be polymerized with a compound of the following formulae 7 to 8.
  • the above polymerization reaction is generally carried out using a Yamamoto or Suzuki coupling reaction. (Chemical Formula 7)
  • X 7 and X 8 are a reactive functional group such as a halogen, borate, boronic acid (BOOH), and OTf.
  • X 7 and X 8 may be selected from the group consisting of hydrogen, an unsubstituted linear or branched alkyl, a cycloalkyl, an alkenyl, an alkynyl, an alkoxy, an aryl, and a heteroaryl. The carbon number thereof is defined as above.
  • an oxidant or a reducing agent may be added during the polymerization reaction.
  • the aromatic group may be a C4 to C30 aromatic group, and preferably a
  • the heteroaromatic group may be a C4 to C14 heteroaromatic group.
  • the aromatic or heteroaromatic group may have a substituent of a C1 to 12 alkyl, alkoxy, or amine.
  • the Ar may be as follows: wherein, in the above formulae, R is hydrogen, a C1 to C12 linear, branched, or cyclic alkyl or alkoxy, or a C4 to 20, preferably C4 to C14 aromatic group.
  • the aromatic group may have a substituent selected from the group consisting of a C1 to C12 alkyl, an alkoxy, or amine, and X 9 is selected from the group consisting of N, O, S 1 and Si.
  • At least one monomer of the chemical formulae 1 to 3 and a monomer of the chemical formula 7 or 8 may be used in a mole ratio of 1 : 0.01 to 100, and preferably 1 : 0.05 to 20.
  • the compounds according to the present invention are applied between an anode made from indium tin oxide (ITO) having a large work function, which injects holes, and a cathode made from metals having various work functions, such as aluminum, lithium fluoride/aluminum, copper, silver, calcium, gold, magnesium, etc., an alloy of magnesium and silver, and an alloy of aluminum and lithium, which injects electrons.
  • ITO indium tin oxide
  • a cathode made from metals having various work functions, such as aluminum, lithium fluoride/aluminum, copper, silver, calcium, gold, magnesium, etc., an alloy of magnesium and silver, and an alloy of aluminum and lithium, which injects electrons.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emitting layer
  • ETL electron transport layer
  • EIL electron injection layer
  • FIG. 1 shows the sectional structure of an electroluminescence display device, where an anode 2 is formed on a substrate 1 by coating an anode material.
  • the substrate 1 includes a material, such as a glass, a plastic, quartz, a ceramic, or silicon, which has transparency, a flat-surface, and water-repellency and is easy to handle, but is not limited thereto.
  • the anode material may include transparent and high conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and so on.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • SnO 2 tin oxide
  • ZnO zinc oxide
  • Materials used as the buffer are exemplified by high molecular materials such as doped polyaniline (PANI) and doped polyethylenedeoxythiopene (PEDOT) and low molecular materials such as alpha- CuPc.
  • a thin film having a thickness from 20 nm to 150 nm was formed by spin coating PANI and PEDOT.
  • a thin film having thickness from 20 nm to 100 nm might be formed by vacuum-deposition of alpha-CuPc.
  • a hole injection layer (HIL) 3 is formed on the anode or the buffer layer by coating a hole injection material using vacuum thermal deposition, or a spin coating method.
  • the hole injection material are not particularly limited, but CuPc or a starburst-type amine such as TCTA, m-MTDATA, m-MTDAPB and so on, can be used.
  • a hole transport layer (HTL) 4 may be formed on the hole injection layer 3 using vacuum thermal deposition or spin coating.
  • the hole transport layer is formed using a material such as N,N'-bis (3-methylphenyl)-N,N'-diphenyl-[1 ,1- biphenyl]-4,4'-diamine (TPD), N,N'-bis(naphthalene-1-yl)-N,N'-diphenyl- benzidine
  • An emitting layer (EML) 5 is formed on the hole transport layer 4 using vacuum thermal deposition or spin coating of an electroluminescence material.
  • an electron transport layer (ETL) 6 is formed using vacuum deposition or spin coating.
  • the electron transport layer 6 may include a material such as AIq 3 or Bu-PBD.
  • An electron injection layer (EIL) 7 may optionally be formed on the electron transport layer 6, but is not limited to specific materials. Examples of a material suitable for the electron injection layer (EIL) 7 may include LiF, NaCI, CsF, Li 2 O, BaO and so on. Then, a cathode is formed on the electron injection layer (EIL) 7 by coating a cathode metal using vacuum thermal deposition to fabricate an organic EL device.
  • the cathode may include a metal such as lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In) 1 magnesium-silver (Mg-Ag), and so on.
  • a front light- emitting device may be obtained by using a light-permeable cathode which contains ITO, IZO, and so on.
  • the compounds are applicable to any one of the hole injection layer 3, the hole transport layer 4, the emitting layer 5, the electron transport layer 6 and the electron injection layer 7 of an EL display device
  • the compounds of the present invention can be used as a host material or as a dopant in an emitting layer.
  • the compound When the compound is used as a host material, it may be used with dopants such as organic compounds having conjugated double bonds.
  • the dopants are organic compounds having conjugated double bonds and materials which have a smaller energy gap than the doped material and thus a lower maximum wavelength value than the doped material, and good energy transfer and chromophore property.
  • At least one compound selected from the group consisting of dicarbazolyl azobenzene (DCAB), fluorenyl diacetylene (FDA), perylene, carbazole, carbazole derivatives, coumarine compounds, and 4-(dicyanomethylene)-2-methyl-6-(1 ,1 ,7,7-tetramethyljulodinyl-9- enyl)-4H-pyran (DCJT) may be used.
  • the dicarbazolyl azobenzene has the chemical formula 9. (Chemical Formula 9)
  • the fluorenyl diacetylene (FDA) has the chemical formula 10.
  • R 26 and R 27 are independently selected from the group consisting of hydrogen, an alkyl, an aryl, cycloalkyl, and acetyl.
  • the perylene has the chemical formula 11. (Chemical Formula 11)
  • coumarine 6 manufactured by EXCITON Corp.
  • chemical formula 13 may be preferably used.
  • the dopants may have more than one substituent to obtain desirable properties such as crystallization degree, thermal stability, solubility, etc.
  • Dicarbazolyl azobenzene (DCAB), fluorenyl diacetylene (FDA), perylene, carbazole, and carbazole derivatives serve as blue dopants, coumarines compounds as green dopants, and 4-(dicyanomethylene)-2-methyl-6- (1 ,1,7,7- tetramethyljulodinyl-9-enyl)-4H-pyran serves as red dopant.
  • a combination of more than one dopant may be used.
  • the conventional chromophore materials may be used.
  • the amount of said dopants is preferably 0.1 to 30 % by weight, more preferably 5 to 30 % by weight, and most preferably 5 to 10 % by weight, based on the amount of low molecular compounds.
  • Example 2 Synthesis of a compound represented by chemical formula 15 (6a).
  • a produced organic layer was washed using 500 ml. of a hydrochloric acid aqueous solution with 1N. After the organic solvent was removed under a reduced pressure, a resulting solid was purifed using train sublimation equipment. In this way, 1.25 g of a compound representd as the chemical formula 24 was gained. The yield of the resulting product was about 70%.
  • the structure of the compound was identified through a 1 H-NMR.
  • Examples 10 to 11 Synthesis of a polymer i) Synthesis of a dibromo monomer compound (5c and 6c in reaction scheme 1 ) substituted for a long alkyl group
  • a dibromo monomer compound (5c and 6c in reaction scheme 1 ) substituted for a long alkyl group
  • Compounds represented by chemical formulae 26 and 27 (5c and 6c in reaction scheme 1 ) were synthesized in the same method as in Examples 4 to 6 i) except that n-octyl bromide was used instead of an alkyl halide CH 3 .
  • the structure of the produced compound was identified through a 1 H-NMR.
  • polymers were synthesized in a generally-known Ni (O)-mediated Yamamoto Aryl coupling method.
  • a representative method of synthesizing the polymer I can be described as follows: a 50 ml-Schlenk flask was several times vacuumed and treated by using nitrogen to completely remove moisture. 305 mg (1.09 mmol) of Ni(COD) 2 and 172 mg (1.09 mmol) of 2,2'-bipyridyl were added in the flask, and thereafter, the flask was several times vacuumed and treated by using nitrogen.
  • FIGS. 2 and 3 illustrate the UV and PL spectra of a compound with the chemical formula 16. As shown in FIG. 2, the UV-vis spectrum shows an absorption band at 389nm. The band is regarded by a ⁇ ⁇ ⁇ * transition of a conjugated double bond. Referring to the PL spectrum, when the excitation wavelength was 338nm, a luminescent color had a maximum blue wavelength of 409nm.
  • ITO layer was formed as an anode on a glass substrate, thereon, MTDATA (4 ) 4',4"-tris ⁇ N-(methylphenyl)-N-phenylamino ⁇ triphenylamine) and NPB were vacuum-deposited, and thereon, compounds prepared according to
  • Examples 1 , 3, 4, and 8 were also vacuum-deposited. Then, AIq 3 was vacuum- deposited on the deposed composition, and thereon, 1 nm of LiF and 200 nm of an aluminum metal were also vacuum-deposited to fabricate a diode. The vacuum deposition was performed at a speed of 1 A/second under a 1 X 10 "6 torr vacuum condition to form a 9 mnf area. The thickness and growing speed of the layer during the depositions were regulated using a layer thickness monitor.
  • ITO indium-tin oxide
  • PEDOT poly(styrene sulfonate)-doped poly (3,4-ethylenedioxy thiophene : Batron P 4083 made by BAYER Co.
  • a composition for an electroluminescent layer which is prepared by dissolving a polymer I prepared according to Example 10 into chlorobenzene, was spin-coated on the hole injection layer, and thereafter, baked at 90 °C for 2 hours in a vacuum oven to completely remove moisture, forming a 800 A-thick electroluminescent layer.
  • Ca and Al in order were deposited to form a 2500- 3000 A-thick cathode while maintaining a vacuum degree of less than 4 X 10 "6 torr, and thereafter, the cathode was encapsulated to complete an organic electroluminescence device.
  • the thickness and growing speed of the Ca and Al layer during the depositions were regulated using a crystal sensor.
  • the organic electroluminescence device had a single layer and a 4 mm 2 light-emitting area.
  • Light-emitting diodes including compounds prepared according to Examples 13 and 14 were estimated about I-V and EL characteristics by applying an electric field thereto.
  • FIG. 4 shows the EL characteristics of light-emitting diodes including a compound of the chemical formula 16.
  • the I-V characteristics of the light-emitting diodes were measured using a Keithley SMU238 and a forward bias voltage as a direct current voltage. Brightness of devices and its efficiency were measured using a brightness meter, PR-650.
  • Table 1 shows the results of turn-on voltage, maximum brightness, Luminous efficiency, and color of the light-emitting diodes including compounds with chemical formulae 14, 16, 20, and 24 and polymers I and III.
  • devices including compounds according to the present invention turned out to have typical diode I -V characteristics and turn- on voltages ranging 3.3 to 4.5 V.
  • the polymers had somewhat lower luminous efficiency compared to that of a low molecular material, but the low luminous efficiency can be improved by copolymerizing the polymers with a monomer having excellent hole or electron transfer characteristics.
  • luminescent colors varied from deep blue to blue ranging 410 to 470 nm.
  • the devices including compounds according to the present invention turned out to have excellent brightness and luminous efficiency.
  • organic compounds for an electroluminescent device can be applied to at least one selected from the group consisting of a hole transport layer, a hole injection layer, an electroluminescent layer, an electron injection layer, and an electron transport layer, or all of them. Since the organic compounds of the present invention have excellent hole transport properties and hole injection properties, they can be preferably applied to a hole transport layer and a hole injection layer. In addition, when the compounds of the present invention were applied to an electroluminescent device, the electroluminescent display device emitting blue color can be driven at a low voltage. Furthermore, suitable host or doping materials that are organic compounds with conjugated double bonds may be used along with the compounds to form a good energy transfer device which makes various color realization at low energy possible, and improves the brightness and luminous efficiency.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention se rapporte à des composés qui incluent un monomère ayant une formule prédéterminée, à des oligomères de ce monomère, et à des polymères de ce monomère pouvant être appliqués sur une couche quelconque sélectionnée parmi une couche d'injection de trous (HIL), une couche de transport de trous (HTL), une couche d'émission (EML), une couche de transport d'électrons (ETL), et une couche d'injection d'électrons (EIL) d'un dispositif d'affichage à électroluminescence organique.
PCT/KR2005/004354 2004-12-17 2005-12-16 Composes et dispositif d'affichage a electroluminescence organique comportant de tels composes WO2006065105A1 (fr)

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WO2010114262A2 (fr) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
JP2011523943A (ja) * 2008-05-19 2011-08-25 メルク パテント ゲーエムベーハー 電子デバイスのための化合物
US8088901B2 (en) * 2007-11-30 2012-01-03 Idemitsu Kosan Co., Ltd. Azaindenofluorenedione derivative, material for organic electroluminescence device and organic electroluminescence device
JP2013161828A (ja) * 2012-02-01 2013-08-19 Konica Minolta Inc 有機光電変換素子
JP2014080421A (ja) * 2012-10-12 2014-05-08 Lab Servier ３−（２−ブロモ−４，５−ジメトキシフェニル）プロパンニトリルの新規合成方法、及びイバブラジン及び薬学的に許容される酸とのその付加塩の合成における適用
US20140306186A1 (en) * 2013-04-10 2014-10-16 Samsung Display Co., Ltd. Heteroaryl-based compound and organic light-emitting diode including the same
CN105440024A (zh) * 2016-01-04 2016-03-30 京东方科技集团股份有限公司 一种化合物及制备方法、有机电致发光器件
WO2017115649A1 (fr) * 2015-12-28 2017-07-06 富士フイルム株式会社 Composé, composition durcissable, article durci, élément optique et lentille
WO2017146022A1 (fr) * 2016-02-23 2017-08-31 富士フイルム株式会社 Résine de polycarbonate, corps moulé, élément optique et lentille
US9755157B2 (en) 2013-08-05 2017-09-05 Cheil Industries, Inc. Organic compound and organic optoelectric device and display device
JP2019069939A (ja) * 2017-10-10 2019-05-09 出光興産株式会社 新規化合物及び有機エレクトロルミネッセンス素子
CN110615783A (zh) * 2019-09-23 2019-12-27 大连理工大学 一类以吡嗪并茚酮为电子受体的电致发光材料及应用
US10604623B2 (en) 2016-02-24 2020-03-31 Fujifilm Corporation Polycarbonate resin, molded article, optical member, and lens
CN115850256A (zh) * 2022-11-25 2023-03-28 东莞伏安光电科技有限公司 一种二氮杂芴的化合物及用于有机电致发光器件的材料和有机电致发光器件

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KR101115760B1 (ko) 2008-05-14 2012-03-07 주식회사 두산 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
KR101121677B1 (ko) * 2009-06-22 2012-02-28 주식회사 두산 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
WO2015108301A1 (fr) 2014-01-14 2015-07-23 삼성에스디아이 주식회사 Composé à anneaux condensés et dispositif électroluminescent organique l'utilisant

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WO2005042176A1 (fr) * 2003-10-29 2005-05-12 E.I. Dupont De Nemours And Company Copolymeres electroluminescents et dispositifs electroniques utilisant de tels polymeres
KR20050056001A (ko) * 2003-12-09 2005-06-14 삼성에스디아이 주식회사 발광 고분자 및 이를 이용한 유기 전계 발광 소자

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JP2002326965A (ja) * 2001-05-02 2002-11-15 Sony Corp スピロフルオレン化合物及びその製造方法、並びにその合成中間体、及びそのスピロフルオレン化合物を用いた有機電界発光素子
WO2004095892A1 (fr) * 2003-04-24 2004-11-04 Idemitsu Kosan Co., Ltd. Dispositif electroluminescent organique et affichage
WO2005042176A1 (fr) * 2003-10-29 2005-05-12 E.I. Dupont De Nemours And Company Copolymeres electroluminescents et dispositifs electroniques utilisant de tels polymeres
KR20050056001A (ko) * 2003-12-09 2005-06-14 삼성에스디아이 주식회사 발광 고분자 및 이를 이용한 유기 전계 발광 소자

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8088901B2 (en) * 2007-11-30 2012-01-03 Idemitsu Kosan Co., Ltd. Azaindenofluorenedione derivative, material for organic electroluminescence device and organic electroluminescence device
JP2011523943A (ja) * 2008-05-19 2011-08-25 メルク パテント ゲーエムベーハー 電子デバイスのための化合物
WO2010114262A3 (fr) * 2009-03-31 2010-12-23 Dow Advanced Display Materials,Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
WO2010114262A2 (fr) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
JP2013161828A (ja) * 2012-02-01 2013-08-19 Konica Minolta Inc 有機光電変換素子
JP2014080421A (ja) * 2012-10-12 2014-05-08 Lab Servier ３−（２−ブロモ−４，５−ジメトキシフェニル）プロパンニトリルの新規合成方法、及びイバブラジン及び薬学的に許容される酸とのその付加塩の合成における適用
US20140306186A1 (en) * 2013-04-10 2014-10-16 Samsung Display Co., Ltd. Heteroaryl-based compound and organic light-emitting diode including the same
US9698356B2 (en) * 2013-04-10 2017-07-04 Samsung Display Co., Ltd. Heteroaryl-based compound and organic light-emitting diode including the same
US9755157B2 (en) 2013-08-05 2017-09-05 Cheil Industries, Inc. Organic compound and organic optoelectric device and display device
US10370473B2 (en) 2015-12-28 2019-08-06 Fujifilm Corporation Compound, curable composition, cured product, optical member, and lens
WO2017115649A1 (fr) * 2015-12-28 2017-07-06 富士フイルム株式会社 Composé, composition durcissable, article durci, élément optique et lentille
JPWO2017115649A1 (ja) * 2015-12-28 2018-09-20 富士フイルム株式会社 化合物、硬化性組成物、硬化物、光学部材及びレンズ
CN105440024A (zh) * 2016-01-04 2016-03-30 京东方科技集团股份有限公司 一种化合物及制备方法、有机电致发光器件
WO2017146022A1 (fr) * 2016-02-23 2017-08-31 富士フイルム株式会社 Résine de polycarbonate, corps moulé, élément optique et lentille
JPWO2017146022A1 (ja) * 2016-02-23 2018-12-13 富士フイルム株式会社 ポリカーボネート樹脂、成形体、光学部材及びレンズ
US10597489B2 (en) 2016-02-23 2020-03-24 Fujifilm Corporation Polycarbonate resin, molded article, optical member, and lens
US10604623B2 (en) 2016-02-24 2020-03-31 Fujifilm Corporation Polycarbonate resin, molded article, optical member, and lens
JP2019069939A (ja) * 2017-10-10 2019-05-09 出光興産株式会社 新規化合物及び有機エレクトロルミネッセンス素子
CN110615783A (zh) * 2019-09-23 2019-12-27 大连理工大学 一类以吡嗪并茚酮为电子受体的电致发光材料及应用
CN110615783B (zh) * 2019-09-23 2021-04-20 大连理工大学 一类以吡嗪并茚酮为电子受体的电致发光材料及应用
CN115850256A (zh) * 2022-11-25 2023-03-28 东莞伏安光电科技有限公司 一种二氮杂芴的化合物及用于有机电致发光器件的材料和有机电致发光器件

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