WO2011108902A2 - Composé comprenant au moins deux composés comportant au moins deux hétérocycles à cinq chaînons, élément électrique organique utilisant ce composé, et borne fabriquée à partir de cet élément - Google Patents

Composé comprenant au moins deux composés comportant au moins deux hétérocycles à cinq chaînons, élément électrique organique utilisant ce composé, et borne fabriquée à partir de cet élément Download PDF

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WO2011108902A2
WO2011108902A2 PCT/KR2011/001539 KR2011001539W WO2011108902A2 WO 2011108902 A2 WO2011108902 A2 WO 2011108902A2 KR 2011001539 W KR2011001539 W KR 2011001539W WO 2011108902 A2 WO2011108902 A2 WO 2011108902A2
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substituted
organic
unsubstituted
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carbon atoms
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WO2011108902A9 (fr
WO2011108902A3 (fr
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박정환
김대성
김기원
박용욱
정화순
변지훈
박정근
최대혁
김동하
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덕산하이메탈(주)
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Publication of WO2011108902A3 publication Critical patent/WO2011108902A3/fr
Publication of WO2011108902A9 publication Critical patent/WO2011108902A9/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound comprising two or more compounds containing two or more five-membered heterocycles, an organic electric device using the same, and a terminal thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • a host / dopant system may be used. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
  • the present inventors have found a compound containing a five-membered heterocyclic ring having a novel structure, and also found that when the compound is applied to an organic electric device, the luminous efficiency, stability and lifetime of the device can be greatly improved.
  • an object of the present invention is to provide a compound containing a novel five-membered hetero ring, an organic electric device using the same, and a terminal thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides a hole injection material, a hole transport material, a light emitting device suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, white, etc., according to a compound including two or more five or more heteroatomic heterocycles. It is useful as a material and / or electron transport material, and as a host material for phosphorescent dopants of various colors.
  • the present invention also provides an organic electronic device using the compound having the above formula and a terminal including the organic electronic device.
  • Compounds containing two or more compounds containing two or more five-membered heterocycles may play various roles in organic electronic devices and terminals, and are suitable for fluorescent and phosphorescent devices of all colors such as red, green, blue, and white. It is useful as a hole injection material, a hole transport material, a light emitting material and / or an electron transport material, and is useful as a host material for phosphorescent dopants of various colors.
  • 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
  • the present invention provides a compound represented by the following formula (1).
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 1 ', R 2 ', R 3 ', R 4 ', R 5 ′, R 6 ′, R 7 ′, R 8 ′, R 9 ′, and R 10 ′ each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted carbon number 1
  • R 1 to R 10 and R 1 ′ to R 10 ′ may combine with adjacent groups to form a saturated or unsaturated ring.
  • neighboring R 1 and R 2 , R 2 and R 3 , ... R 8 and R 9 , R 9 and R 10 may combine to form a saturated or unsaturated ring.
  • neighboring R 1 'and R 2 ', R 2 'and R 3 ', ... R 8 'and R 9 ', R 9 'and R 10 ' may combine to form a saturated or unsaturated ring have.
  • (3) X may be carbon (C) or nitrogen (N).
  • Ar represents a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 To 60 arylene group, substituted or unsubstituted aryl group having 5 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus ( A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or at least one of P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si); Substituted or unsubstituted C 5 to 60 containing at least one or more
  • Heteroaryl group or substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms containing at least one or more sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si). .
  • the compound having the above structural formula can be used in a soluble process. That is, the organic material layer of the organic electric device, which will be described later, may be formed by the soluble process using the compound.
  • the organic material layer of the organic electronic device is made by using a variety of polymer materials, and less by a solvent process (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method) rather than deposition. It can be prepared in a number of layers.
  • the present invention provides a compound represented by the following formula (2).
  • the present invention provides a compound represented by the formula (3) below.
  • Substituents of ', R 5 ', R 6 ', R 7 ', R 8 ', R 9 ', and R 10 ' may be substituted or unsubstituted.
  • Specific examples of the compounds belonging to Chemical Formulas 1 to 3, which are compounds including two or more five-membered heterocyclic rings, according to one embodiment of the present invention include the compounds of Formula 4 below, but the present invention It is not limited only to.
  • the compounds of Formula 4 below are represented by R 1 to R 10 and R 1 'to R 10 ' are hydrogen atoms, but may be other functional groups described in Formulas 1 to 3.
  • the compounds represented by Formulas 1 to 3 may be represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 1 ', R 2 ', Substituted or unsubstituted substituents of the substituents of R 3 ′, R 4 ′, R 5 ′, R 6 ′, R 7 ′, R 8 ′, R 9 ′, and R 10 ′ exemplify all compounds in a broad context. Since it is difficult to realistically describe exemplary compounds by way of example, the compounds represented by Chemical Formulas 1 to 3 not described in Chemical Formula 4 may also form part of the present specification.
  • organic electroluminescent devices in which compounds including two or more compounds including two or more five-membered heterocycles described with reference to Chemical Formulas 1 to 4 are used as the organic material layer.
  • organic electroluminescent devices in which compounds including two or more compounds including two or more five-membered heterocycles described with reference to Chemical Formulas 1 and 4 may be used include, for example, an organic light emitting diode (OLED), an organic solar cell, Organophotoreceptor (OPC) drums, organic transistors (organic TFTs), photodiodes, organic lasers, laser diodes, and the like.
  • organic electroluminescent device to which compounds including two or more five-membered heterocyclic rings described with reference to Chemical Formulas 1 to 4 may be applied is described below.
  • the present invention is not limited thereto, and a compound including two or more compounds including two or more five-membered heterocycles described above may be applied to various organic electric devices.
  • Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between these electrodes, at least one of the organic material layer of the organic electric field comprising the compounds of the formula (1) Provided is a light emitting device.
  • 1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
  • At least one layer of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer is formed to include the compounds of Formulas 1 to 6 above. Except for the above, it may be manufactured in a structure known in the art using conventional manufacturing methods and materials in the art.
  • FIGS. 1 to 6 The structure of the organic light emitting display device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited thereto.
  • reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode.
  • the organic light emitting diode may further include a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for preventing the movement of electrons, and a protective layer.
  • the protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.
  • the compound including two or more compounds containing two or more five-membered heterocyclic ring described with reference to Formulas 1 to 4 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer.
  • the compound including two or more compounds containing two or more five-membered heterocyclic ring described with reference to Formulas 1 to 4 is a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, It may be used in place of one or more of the electronic blocking layer, the protective layer, or may be used by forming a layer with them.
  • the organic layer may be used not only in one layer but also in two or more layers.
  • Compounds including two or more compounds containing two or more five-membered heterocycles described with reference to Formulas 1 to 4 may play various roles in the organic electronic device and the terminal, and all of red, green, blue, white, etc. It is useful as a hole injection material, a hole transport material, a light emitting material and / or an electron transport material suitable for color fluorescence and phosphorescent devices, and can be used as a host material for phosphorescent dopants of various colors.
  • the organic light emitting device is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • PVD physical vapor deposition
  • An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
  • PVD physical vapor deposition
  • an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer may be formed by using a variety of polymer materials, and by using a process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • An organic light emitting display device forms an organic material layer, for example, a light emitting layer, by a soluble process of a compound containing two or more compounds including two or more five-membered heterocycles described above. You may.
  • the substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.
  • An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the hole injection layer is located on the anode.
  • the conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.
  • the hole injection material is a material capable of well injecting holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is positioned on the hole injection layer.
  • the hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons.
  • applications for vehicle body display require heat resistance to the device, and materials having a glass transition temperature (Tg) of 70 or higher are preferred.
  • Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium oxide Compound, a silicon-based arylamine compound, and the like.
  • the organic light emitting layer is positioned on the hole transport layer.
  • the organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 ') to increase blue light emission efficiency.
  • an organic light emitting layer is formed of a polymer of polyphenylene vinylene (PPV) or a polymer such as poly fluorene.
  • PPV polyphenylene vinylene
  • a polymer such as poly fluorene can be used for
  • the electron transport layer is positioned on the organic light emitting layer.
  • the electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron injection layer is stacked on the electron transport layer.
  • the electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like.
  • the electron injection layer may be formed in a thickness range of 100 ⁇ 300.
  • the cathode is positioned on the electron injection layer. This cathode serves to inject electrons.
  • the material used as the cathode it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection.
  • a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used.
  • an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 or less can also be used.
  • holes suitable for fluorescence and phosphorescent devices of all colors such as red, green, blue, and white, depending on the compound including two or more compounds including two or more five-membered heterocycles described with reference to Chemical Formulas 1 to 12 It can be used as an injection material, a hole transport material, a light emitting material, an electron transport material and an electron injection material, and can be used as a host material for phosphorescent dopants of various colors.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device.
  • This terminal means a current or future wired or wireless communication terminal.
  • the terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.
  • step 1 The intermediate A obtained in step 1) was dissolved in anhydrous THF, the temperature of the reaction was lowered to 8, n-BuLi (1.6 M in hexane) was slowly added dropwise, and the reaction was stirred at 0 to 1 hour. The temperature of the reaction was lowered to -78, Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added dropwise and stirred at room temperature for 12 hours. After completion of the reaction, the mixture was extracted with CH 2 Cl 2 , water was removed from the reaction with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated to give the resulting product as methyl alcohol.
  • n-BuLi 1.6 M in hexane
  • the intermediate A, 9-Anthraceneboronic acid, Pd (PPh 3 ) 4 and K 2 CO 3 synthesized in step 1) were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated and the resulting product was recrystallized using a toluene solvent to give the desired compound 10 (yield: 71%).
  • the compounds represented by Formulas 1 to 3 are R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 1 ', R 2 ', R 3
  • Substituted or unsubstituted substituents of the substituents of ', R 4 ', R 5 ', R 6 ', R 7 ', R 8 ', R 9 ', and R 10 ' are compounds represented by the general formula (4) in a broad relationship. Synthesis examples of some of the above, but the compounds represented by the formula (1) to 4 not illustratively described as a synthesis example may also form part of the present specification.
  • a copper phthalocyanine (hereinafter abbreviated as CuPc) film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a thickness of 10 nm.
  • a-NPD 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • compounds 10, 26, 38, and 56 were deposited on the hole transport layer as phosphorescent host materials to form a light emitting layer.
  • tris (2-phenylpyridine) iridium (abbreviated as I r (ppy) 3 hereinafter) was added as a phosphorescent Ir metal complex dopant.
  • concentration of I r (ppy) 3 in the light emitting layer was 5% by weight.
  • (1,1-bisphenyl) -4-oleato) bis (2-methyl-8-quinolinoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, followed by electrons.
  • Tris (8-quinolinol) aluminum (hereinafter abbreviated to Alq 3 ) was formed into an injection layer to a thickness of 40 nm.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.
  • an organic electroluminescent device having the same structure as the test example was manufactured using a compound represented by Chemical Formula 13 (hereinafter abbreviated as CBP) as a light emitting host material instead of the compound of the present invention.
  • CBP Chemical Formula 13
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention is not only excellent in the luminous efficiency compared to the CBP used as a comparative example, Since green light emission is obtained in which color purity is remarkably improved, it is used as a phosphorescent host material of an organic light emitting display device, and thus light emission efficiency and color purity may be remarkably improved.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, the host material of the light emitting layer, as well as the electron injection layer, the electron transport layer, the hole injection layer and the hole transport layer.
  • the compounds represented by Formulas 1 to 4 are R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 1 ', R 2 ', R 3
  • Substituted or unsubstituted substituents of ', R 4 ', R 5 ', R 6 ', R 7 ', R 8 ', R 9 ', and R 10 ' are some of the compounds represented by the formula (4) in a broad relationship.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne un composé comprenant au moins deux composés comportant au moins deux hétérocycles à cinq chaînons, un élément électrique organique utilisant ce composé, et une borne fabriquée à partir de cet élément.
PCT/KR2011/001539 2010-03-05 2011-03-07 Composé comprenant au moins deux composés comportant au moins deux hétérocycles à cinq chaînons, élément électrique organique utilisant ce composé, et borne fabriquée à partir de cet élément WO2011108902A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020100019950A KR101181280B1 (ko) 2010-03-05 2010-03-05 2개 이상의 오원자 헤테로고리를 포함하는 화합물이 2개 이상 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말
KR10-2010-0019950 2010-03-05

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WO2011108902A2 true WO2011108902A2 (fr) 2011-09-09
WO2011108902A3 WO2011108902A3 (fr) 2012-01-12
WO2011108902A9 WO2011108902A9 (fr) 2012-03-01

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WO2015190400A1 (fr) * 2014-06-11 2015-12-17 保土谷化学工業株式会社 Dérivé de pyrimidine et élément électroluminescent organique
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DE102017112435A1 (de) * 2017-06-06 2018-12-06 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
CN109071555A (zh) * 2016-04-29 2018-12-21 株式会社斗山 有机发光化合物及利用其的有机电致发光元件
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WO2012079678A1 (fr) * 2010-12-13 2012-06-21 Merck Patent Gmbh Tétraarylbenzènes substitués
US20130299794A1 (en) * 2010-12-31 2013-11-14 Ho-Kuk Jung Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
JP2014520882A (ja) * 2011-07-21 2014-08-25 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 新規有機エレクトロルミネセンス化合物およびこれを使用した有機エレクトロルミネセンス素子
WO2013012296A1 (fr) * 2011-07-21 2013-01-24 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique comprenant lesdits composés
WO2013012297A1 (fr) * 2011-07-21 2013-01-24 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
JP2014525910A (ja) * 2011-07-21 2014-10-02 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 新規有機エレクトロルミネセンス化合物およびこれを使用した有機エレクトロルミネセンス素子
CN103797014A (zh) * 2011-07-21 2014-05-14 罗门哈斯电子材料韩国有限公司 新有机电致发光化合物和使用该化合物的有机电致发光器件
CN103827119A (zh) * 2011-07-21 2014-05-28 罗门哈斯电子材料韩国有限公司 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件
JP2013046067A (ja) * 2011-08-26 2013-03-04 ▲いく▼▲雷▼光電科技股▲分▼有限公司 有機ｅｌ装置に用いられる化合物、及びそれを用いた有機ｅｌ装置
JP2013087090A (ja) * 2011-10-18 2013-05-13 Idemitsu Kosan Co Ltd 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子
CN103958642A (zh) * 2011-12-23 2014-07-30 第一毛织株式会社 用于有机光电子元件的化合物、包括该化合物的有机发光元件和包括该有机发光元件的显示装置
CN103958642B (zh) * 2011-12-23 2017-03-08 第一毛织株式会社 用于有机光电子元件的化合物、包括该化合物的有机发光元件和包括该有机发光元件的显示装置
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WO2013109045A1 (fr) * 2012-01-16 2013-07-25 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
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CN104245686A (zh) * 2012-02-17 2014-12-24 罗门哈斯电子材料韩国有限公司 新有机电致发光化合物和使用该化合物的有机电致发光器件
JP2015512875A (ja) * 2012-02-17 2015-04-30 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 新規有機エレクトロルミネセンス化合物およびそれを使用した有機エレクトロルミネセンス素子
WO2013122402A1 (fr) * 2012-02-17 2013-08-22 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
CN104271582A (zh) * 2012-05-02 2015-01-07 罗门哈斯电子材料韩国有限公司 新有机电致发光化合物和包含该化合物的有机电致发光器件
WO2014061961A1 (fr) * 2012-10-16 2014-04-24 Rohm And Haas Electronic Materials Korea Ltd. Composés à électroluminescence organique et dispositif à électroluminescence organique les comprenant
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JPWO2015190400A1 (ja) * 2014-06-11 2017-04-20 保土谷化学工業株式会社 ピリミジン誘導体および有機エレクトロルミネッセンス素子
WO2015190400A1 (fr) * 2014-06-11 2015-12-17 保土谷化学工業株式会社 Dérivé de pyrimidine et élément électroluminescent organique
US10418562B2 (en) 2015-02-06 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
JPWO2016129687A1 (ja) * 2015-02-13 2017-11-30 出光興産株式会社 化合物、組成物、有機エレクトロルミネッセンス素子、および電子機器
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CN106892901A (zh) * 2017-04-21 2017-06-27 瑞声光电科技(常州)有限公司 三嗪化合物及发光器件
DE102017112435A1 (de) * 2017-06-06 2018-12-06 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
DE102017112435B4 (de) * 2017-06-06 2019-01-17 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen

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