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WO2001090098A1 - Derive de coumarine et son utilisation - Google Patents

Derive de coumarine et son utilisation Download PDF

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Publication number
WO2001090098A1
WO2001090098A1 PCT/JP2001/004219 JP0104219W WO0190098A1 WO 2001090098 A1 WO2001090098 A1 WO 2001090098A1 JP 0104219 W JP0104219 W JP 0104219W WO 0190098 A1 WO0190098 A1 WO 0190098A1
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Prior art keywords
general formula
coumarin derivative
organic
light
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2001/004219
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English (en)
Japanese (ja)
Inventor
Makoto Satsuki
Yoshimi Takahashi
Chika Sasaki
Akira Shinpo
Sadaharu Suga
Hisayoshi Fujikawa
Atsushi Miura
Shizuo Tokito
Yasunori Taga
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hayashibara Seibutsu Kagaku Kenkyujo KK
Original Assignee
Hayashibara Seibutsu Kagaku Kenkyujo KK
Hayashibara Biochemical Laboratories Co Ltd
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Priority claimed from JP2000153408A external-priority patent/JP2001329257A/ja
Priority claimed from JP2001040690A external-priority patent/JP4982642B2/ja
Application filed by Hayashibara Seibutsu Kagaku Kenkyujo KK, Hayashibara Biochemical Laboratories Co Ltd filed Critical Hayashibara Seibutsu Kagaku Kenkyujo KK
Publication of WO2001090098A1 publication Critical patent/WO2001090098A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine

Definitions

  • the present invention relates to a coumarin derivative and its use, and more particularly, to a luminescent agent for an organic electroluminescent device.
  • CRTs are mainly used for relatively large information display devices such as computer terminals and television receivers.
  • CRTs are both large in volume and weight and have high operating voltages, making them unsuitable for consumer devices and small devices that emphasize portability.
  • Small devices need to be thinner, lighter, flat, have lower operating voltage, and consume less power.
  • liquid crystal devices are used in many fields because of their low operating voltage and relatively low power consumption.
  • a clear display cannot be obtained unless the image is read within a certain angle range, and a backlight is usually required.
  • An organic EL device has emerged as a display device that solves these problems.
  • Organic EL devices usually have a light-emitting layer containing a light-emitting compound interposed between an anode and a cathode, and apply a DC voltage between the anode and the cathode to apply holes and electrons to the light-emitting layer. Are injected into each other, and they are recombined with each other to create an excited state of the luminescent compound.
  • This is a light-emitting element that uses light emission such as fluorescence or phosphorescence emitted when returning to the device.
  • the organic EL device is capable of emitting light by forming a light emitting layer by selecting an appropriate organic compound as a host compound and changing a guest compound (dopant) to be combined with the host compound.
  • an organic EL element emits light by itself, so an information display device using it does not depend on the viewing angle and does not require a backlight. It is said to be an element.
  • organic EL devices that emit light in the green range
  • improvements in luminous efficiency and emission spectrum by the addition of a guest compound have been reported, but organic EL devices that emit light in the red range have not been reported.
  • an effective guest compound has not yet been found, not only the color purity and luminance but also the durability and the reliability are still insufficient.
  • the organic EL device disclosed in Japanese Patent Application Laid-Open No. 10-60427 and US Pat. No. 4,769,922 has a low luminance and a pure red light emission. Because of this, there is still a problem in achieving full color.
  • an object of the present invention is to provide an organic compound useful in various fields, such as an organic EL device, in which a compound having a light emission maximum in a visible region is required. Disclosure of the invention
  • a chalcone-like structure (1,3—dipyronyl-2-propene) was found in the molecule.
  • coumarin derivative has a light emission maximum in a target visible region, and when used in an organic EL device as a luminescent agent, It has been found that high-luminance red to orange light is emitted over a long period of time.
  • the present invention is based on the discovery of the industrially useful properties of certain coumarin derivatives.
  • FIG. 1 is a schematic diagram of an organic EL device according to the present invention.
  • FIG. 2 is a schematic diagram of a display panel according to the present invention.
  • FIG. 3 is a block diagram of the information display device according to the present invention.
  • 1 and 10 are substrates
  • 2, and 14 are anodes
  • 3, 16 are hole injection and transport layers
  • 4, 18 are light emitting layers
  • 5 is electron injection and transport layers
  • 6 20 is the cathode
  • 30 is the DC power supply
  • 32 34 is the booster circuit
  • 36 46 is the driver circuit
  • 38 is the microcomputer
  • 40 is the clock generation circuit
  • 42 and 44 indicate an oscillation circuit
  • 48 indicates a display panel.
  • the present invention solves the above-mentioned problems by providing a coumarin derivative having a chalcone-like structure in a molecule, and in particular, by providing a luminescent agent for an organic EL device comprising a coumarin derivative represented by the general formula 1. Is what you do.
  • R 1 to R 2 represent a hydrogen atom or an appropriate substituent.
  • the individual substituent include a methyl group, an ethyl group, a vinyl group, a propyl group, an isopropyl group, a 1-propyl group, a 2-propyl group, an isopropyl group, and a butyl group.
  • one or more of the hydrogen atoms are, for example, methyl, ethyl, propyl, isopropyl, butyl, isopropyl, sec-butyl, tert-butyl, pentyl Group, isopentyl group, neopentyl group, tert-pentyl group and other short-chain long-chain aliphatic hydrocarbon groups, methoxy group, trihalomethoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group Alkoxy groups such as tert-butoxy group, methoxycarbonyl group, trifluoromethoxycarbonyl group, ethoxycarbonyl group, etc., methylsulfonyl group, trimethylfluoromethylsulfonyl group, ethyl Alkylsulfonyl groups such as sulfonyl groups, halo such as chloro groups, chloro groups, promo groups and
  • the coumarin derivative referred to in the present invention is a coumarin derivative having a chalcone-like structure in the molecule, particularly a compound having a basic skeleton represented by the general formula 1, and
  • R 1 to R 12 in the general formula 1 are hydrogen atoms or an appropriate substituent. It does not matter.
  • the desirable group of coumarin derivatives used in the present invention depends on the type and amount of the host compound, the material for the hole injection / transport layer, the material for the electron injection Z transport layer, etc., which are used in combination in the organic EL device.
  • R 2 and / or R "in the general formula ⁇ is a substituent represented by the general formula 2, in its R 2 and or R n, is R u and Roh or R 1 4 in the general formula 2, A carbon atom adjacent to the carbon atom to which R 2 is bonded, or a carbon atom adjacent to the carbon atom to which R is bonded to form a cyclic structure Z, Z 2 , Z 3 and Z or Z 4 And those represented by general formulas 3 to 5.
  • R 13 and R each independently represent a hydrogen atom or an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or an ether group, and these aliphatic hydrocarbon groups, aromatic hydrocarbon groups And the ether group may have a substituent.
  • the aliphatic hydrocarbon group, aromatic hydrocarbon group and ether group in the general formula 2 and the substituents which they may have, the same groups as those in R 1 to R 12 in the general formula 1 are selected. Therefore, the cyclic structures Z and Z 4 are each a monocyclic or polycyclic five-membered heterocyclic group containing one or more nitrogen atoms in the ring and having one or more substituents. It is a ring or a six-membered heterocyclic ring.
  • R 1 , R 3 , and R 1 (1 or R 2 in the general formula 1) are apparently absent.
  • Specific examples of the coumarin derivative used in the present invention include, for example, those represented by Chemical Formulas 1 to 62. Each of these compounds has a light emission maximum such as a fluorescence maximum in a red or near red region and forms a stable thin film in a glassy state. Therefore, these may be used alone or in combination with another light emitting compound. Accordingly, it can be used very advantageously as a luminescent agent for an organic EL device.
  • Chemical formula 16 Chemical formula 17: Chemical formula 18: Chemical formula 19:
  • Chemical formula 41 Chemical formula 42: Formula 44: Chemical formula 45: Chemical formula 46: Chemical formula 47: Formula 4B:
  • Chemical Formula 49 Formula 50: Chemical Formula 51 Chemical Formula 52: Chemical Formula 53:
  • the coumarin derivative used in the present invention can be prepared by various methods, but if importance is placed on economy, for example, it is represented by the general formula 6 having R, to R 6 corresponding to the general formula 1.
  • a preferred method is to react a compound represented by the general formula 7 having R 8 to R 2 corresponding to the general formula 1 with a compound represented by the general formula 7.
  • the compound represented by the general formula 6 and the compound represented by the general formula 7 are respectively dissolved in a reaction vessel in an appropriate amount (usually equimolar) and, if necessary, appropriately in a solvent.
  • a reaction vessel in an appropriate amount (usually equimolar) and, if necessary, appropriately in a solvent.
  • solvent examples include pentane, hexane, cyclohexane, hydrocarbons such as hexane, benzene, toluene, and xylene, carbon tetrachloride, chloroform, 1,2-dichloroethane, 1,2-dibromoethane, and the like.
  • Trichloroethylene, tetrachloroethylene, cyclobenzene, promobenzene, ⁇ -halogen compounds such as cyclobenzene, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutyl alcohol , Isopentyl alcohol, cyclohexanol, ethylene glycol, propylene glycol, 2-methoxyethanol, 2-ethoxyethanol, phenol, benzyl alcohol, cresol, diethylene glycol, triethylene glycol Alcohols and phenols such as glycerol and glycerin, getyl ether, diisopropyl ether, tetrahydrofuran, tetrahydroviran, 1,4-dioxane, anisol, 1,2-dimethyloxetane, diethylene glycol dimethyl ether , Dicyclohexyl-18-chloro-6, ethers such as methyl carbitol
  • the amount of the solvent be 100 times, usually 5 to 50 times, the weight of the whole starting compound.
  • the reaction is completed within 10 hours, usually 0.5 to 5 hours, depending on the type of the starting compound and the reaction conditions.
  • the progress of the reaction can be monitored by general-purpose methods such as thin-layer chromatography, gas chromatography, and high-performance liquid chromatography. Any of the coumarin derivatives represented by Chemical Formulas 1 to 62 can be produced in a desired amount by this method.
  • the compound represented by the general formula 5 is, for example, supervised by Munio Kotake, “Daikaku Kagaku Kagaku”, 1959, published by Asakura Shoten Co., Ltd., Volume 14 (I), 241
  • a salicylaldehyde derivative represented by the general formula 8 having R, to R 4 corresponding to the general formula 1 and R 5 and R corresponding to the general formula 1 It can be prepared by reacting a 3-ethyl oxobutanoate derivative having 6 with.
  • the compound represented by the general formula 8 can be obtained, for example, according to the method described in the above-mentioned reference or according to the method described in Japanese Patent Publication No. 60-23336.
  • the coumarin derivative thus obtained may be used in the form of a reaction mixture depending on the application, but usually, prior to use, for example, dissolution, separation, gradient, filtration, extraction, concentration, and thin layer formation. Purified by general-purpose methods for purifying analogous compounds such as chromatography, column chromatography, gas chromatography, high-performance liquid chromatography, distillation, sublimation, crystallization, etc. Are applied in combination.
  • the coumarin derivative of the present invention is used in, for example, an organic EL device or a dye laser, it should be highly purified prior to use, for example, by a method such as distillation, crystallization and / or sublimation. Is desirable.
  • sublimation facilitates the production of high-purity crystals in a single operation, reduces the loss of the coumarin derivative during the operation, and does not incorporate any solvent into the crystals.
  • the sublimation method to be applied may be the normal pressure sublimation method or the reduced pressure sublimation method, but usually the latter reduced pressure sublimation method is applied.
  • To vacuum sublimation of Kumari down derivative of the present invention for example, charged Kumari down derivatives q.s. into the sublimation purification apparatus 1 0 in the apparatus - below 2 T orr reduced pressure, preferably, 1 0- 3 T Heat at a temperature as low as possible below the melting point while keeping the temperature below 0 rr so that the coumarin derivative does not decompose.
  • the sublimation rate is suppressed by adjusting the degree of vacuum or heating temperature so that no impurities are mixed, and when the coumarin derivative is difficult to sublimate.
  • Sublimation by passing an inert gas such as a rare gas into the sublimation purification equipment.
  • the size of the crystals obtained by sublimation can be adjusted by adjusting the temperature of the condensing surface in the sublimation purification equipment, keeping the condensing surface slightly lower than the heating temperature and gradually crystallizing. A relatively large crystal is obtained.
  • the coumarin derivative according to the present invention has an emission maximum in the visible region and emits red to orange fluorescent light when excited. By appropriately combining with a host compound, it can be used very advantageously as a luminescent agent for an organic EL device.
  • the coumarin derivative represented by the general formula 1 has an emission maximum in the visible region, more specifically, in the red or near red region, and forms a stable thin film in a glassy state. Therefore, when used alone or in combination with another luminescent compound, it can be used very advantageously as a luminescent agent for an organic EL device.
  • the organic EL device according to the present invention means an electroluminescent device using such a luminescent agent in general, and in particular, an anode for applying a positive voltage, a cathode for applying a negative voltage, and a recombination of holes and electrons.
  • Single-layer and stacked organic EL devices are important applications.
  • an organic EL element essentially consists of a process of injecting electrons and holes from an electrode, a process of moving electrons and holes through a solid, and a recombination of electrons and holes. It consists of a process of generating a singlet exciton or a triplet exciton and a process of emitting light from the exciton, and these processes are essentially the same in both single-layer and stacked organic EL devices.
  • the characteristics of the above four processes can be improved only by changing the molecular structure of the light-emitting compound.
  • the functions required in each process are shared among multiple materials and each material can be optimized independently. Also, it is easier to achieve the desired performance if it is configured as a stacked type.
  • FIG. 1 is a schematic diagram of a stacked organic EL device according to the present invention, where 1 is a substrate.
  • glass such as soda glass, barium silicate glass, and aluminosilicate glass, or a substrate material such as plastic or ceramic is used.
  • substrate materials are transparent glass and plastic, and opaque ceramics such as silicon are used in combination with transparent electrodes.
  • Reference numeral 2 denotes an anode, which is made of a metal or a conductive compound which is electrically low-resistive and has a high light transmittance over the entire visible region, usually by vacuum evaporation, screen ring, or chemical vapor deposition. CVD), Atomic Layer Epitaxy (ALE), coating, dipping, etc., so that it is in close contact with one side of the substrate 1 so that the resistivity at the anode 2 is 1 kQZ or less. It is formed by forming a film having a thickness of 10 to 100 nm, preferably 50 to 500 nm.
  • Examples of such conductive materials include metals or alloys such as gold, platinum, aluminum, and nickel, tin oxide, indium oxide, and mixed systems of tin oxide and indium (hereinafter, abbreviated as ITO j).
  • ITO j tin oxide, indium oxide, and mixed systems of tin oxide and indium
  • a metal oxide or a conductive ligomer or polymer having repeating units of aniline, thiocyanphen, pyrrole, etc. is used, of which ITO having a low resistivity is easily used.
  • a fine pattern can be easily formed by etching using an acid.
  • Reference numeral 3 denotes a hole injecting / transporting layer, which is usually brought into close contact with the anode 2 by a method similar to that for the anode 2 so that the material for the hole injecting / transporting layer has a thickness of 1 to 1,0,0. It is formed by forming a film to a thickness of 100 nm.
  • a hole injection / transport layer timber in order makes it easier to transport and hole injection from the anode 2, low ionization potential, and, for example, Te field under the smell of 1 0 4 to 1 0 6 VZ cm , at a minimum, which exhibits a hole mobility of 1 0- 6 cm 2 V ⁇ s is desirable.
  • Individual hole injecting / transporting layer materials are commonly used in organic EL devices, for example, aromatic tertiary amines, styrylamines, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazolines Derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amine-substituted chalcone derivatives, genoxazole derivatives, styryllanthracene derivatives, fulgenrenon derivatives, hydrazone derivatives, stilbene derivatives, and the like. These are used in combination.
  • Reference numeral 4 denotes a light-emitting layer, which is usually attached to the hole injection / transport layer 3 in the same manner as that for the anode 2 so that one or a plurality of light-emitting compounds are separated into a single layer or two layers. It is formed by forming a film having a thickness of 1 to 1, OOO nm, and preferably a thickness of 0 to 200 nm.
  • a coumarin derivative represented by the general formula 1 may be used alone, or a coumarin derivative represented by the general formula 1 as a guest compound may be used in a thin film state as a host compound.
  • One or more other luminescent compounds that provide luminescence quantum efficiency are used.
  • Examples of the individual luminescent compounds that can be used in combination with the coumarin derivative of the present invention include, for example, oxathiazole, phenanthrene, triazole, quinacridone, luprene or a derivative thereof, a quinolinol metal complex, and distyrylaryl.
  • Examples include a monolen derivative or a spiro compound thereof, and a diphenylanthracene derivative.
  • distyryl arylene derivatives, their spiro compounds, and diphenylanthracene derivatives usually have wavelengths of from 330 to 5 It has an emission maximum such as a fluorescence maximum in the blue or green region of 10 nm, and its emission wavelength is substantially the same as the absorption maximum wavelength of the coumarin derivative according to the present invention (usually 470 to 510 nm). Overlap. Therefore, when these luminescent compounds having an emission maximum in the blue or green range are used in the light-emitting layer 4 in combination with the coumarin derivative of the present invention, the former excitation energy is more efficient than the coumarin derivative of the present invention. Therefore, it functions as an extremely effective host compound in an organic EL device that emits red to orange light or white light described below.
  • the most desirable host compound for emitting red to orange light is a quinolinol metal complex
  • the quinolinol metal complex referred to in the present invention is a compound having a quinolinol as a ligand and an organic EL element. It means all metal complexes that can be used as host compounds.
  • Preferred quinolinol metal complexes are metal complexes having 8-quinolinols as ligands, such as aluminum, zinc, beryllium, magnesium, indium, lithium, calcium, calcium, and the like. And those having a central atom of a metal of Group 1, Group 2, Group 12 or Group 13 or an oxide thereof in the periodic table.
  • 8-quinolinols as ligands may be located at a site other than the 8-position to which a hydroxy group is bonded, for example, a halogen group such as a chloro group, a chloro group or a bromo group. , Methyl, trifluoromethyl, ethyl, propyl, and other short-chain alkyl groups or haloalkyl groups, alkoxy groups, such as methoxy, ethoxy, and propoxy groups, and methoxycarbonyl groups. And an alkoxycarbonyl group such as an ethoxycarbonyl group, and one or more substituents such as a cyano group, a nitro group, a sulfonyl group and a hydroxy group.
  • a halogen group such as a chloro group, a chloro group or a bromo group.
  • Examples of the individual quinolinol metal complexes include, for example, tris (8-quinolinolate) aluminum, tris (3,4-dimethyl-8-quinolinolate) Aluminum, tris (4-methyl-18-quinolinolate) aluminum, tris (4-methoxy8-quinolinolate) aluminum, tris (4,5-dimethyl-18-quinoline) Aluminum, tris (4,6-dimethyl-8-quinolinolate) aluminum, tris (5-chloro-8-quinolineolate) aluminum, tris (5-bromo-8-quinolineolate) aluminum, metal Squirrel (5,7-dichloro-8-quinolinolate) aluminum, tris (5-cyano-8-quinolinolate) aluminum, tris (5-sulfonyl-8-quinolinolate) aluminum), Tris (5-propyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolino) Aluminum complex such as aluminum oxide, bis (8-quinolinolate) zinc, bis
  • Um complex bis (8-quinolinolate) magnesium, bis (2-methyl-8-quinolinolate) magnesium, bis (2,4-dimethyl) — 8—Quinolinolate) Magnesium, bis (2-methyl-1-5-cyano-18—quinolinolate) magnesium, bis (3,4—dimethyl-18—quinolinolate) magnesium, bis (4, Magnesium complex such as magnesium, bis (5-chloro-8-quinolinolate) magnesium, bis (5,7-dichloro-8-quinolinolate) magnesium Indium complexes such as tris (8-quinolinol) indium; gallium complexes such as tris (5-chloro-8-quinoline) gallium; bis (5—quinoline 18—quino) Linolate) Calcium complexes such as calcium are exemplified, but these are merely examples, and the quinolinol metal complex referred to in the present invention is not limited.
  • the quinolinol metal complex has two or more ligands in the molecule, these ligands may be the same or different.
  • the coumarin derivative represented by the general formula 1 is used as a guest compound, it usually depends on the type of the host compound to be combined, but usually 0.01 mol% or more based on the host compound. Desirably, it is added in the range of 0.1 to 10 mol%.
  • Reference numeral 5 denotes an electron-injecting Z transport layer, which is usually an organic compound having a high electron affinity by being brought into close contact with the light-emitting layer 4 by the same method as that for the anode 2 to emit light in the red or near red region. It does not absorb, for example, the same compound as in the light-emitting layer 4, or a cyclic ketone or a derivative thereof such as benzoquinone, anthraquinone, or fullerenone, a silazane derivative, or an anily.
  • It is formed by forming one or more conductive oligomers or polymers having a repeating unit of thiophene, thiophene, pyrrole or the like to a thickness of 10 to 500 nm.
  • a plurality of materials for the electron injection / transport layer are used, even if the materials for the electron injection / transport layers are uniformly mixed to form a single layer, the materials for the electron injection / transport layer can be mixed without mixing. Adjacent to May be formed in a plurality of layers.
  • Reference numeral 6 denotes a cathode, which is usually in close contact with the electron injection / transport layer 5 and has a lower work function (typically 6 eV or less) than the compound used in the electron injection / transport layer 5, for example, lithium, magnesium, and calcium.
  • Metal, metal oxide such as silver, copper, aluminum, indium, or indium, or a conductive compound, alone or in combination, or a buffer layer such as copper lid cyanine and an ITO electrode. are combined to form a cathode.
  • the thickness of the cathode 6 is not particularly limited, and is usually 1 O nm or more so that the resistivity is 1 / port or less, while taking into account the conductivity, manufacturing cost, overall device thickness, light transmittance, and the like.
  • An interface layer containing an organic phosphorus compound or the like, or a thin film of an alkali metal or an alkaline earth metal may be provided to improve electron injection efficiency.
  • the organic EL device of the present invention comprises an anode 2, a light-emitting layer 4, and a cathode 6, a hole injection / transport layer 3, and an electron injection / transport layer 5, if necessary.
  • the host compound and the coumarin derivative of the present invention are mixed in advance at a predetermined ratio, or the heating rates of the two in vacuum deposition are made independent of each other.
  • the organic EL device thus constructed is designed to minimize degradation in the operating environment. It is desirable that a part or the whole be sealed with a sealing glass or a metal cap in an inert gas atmosphere, or covered with a protective layer of an ultraviolet curable resin or the like.
  • the organic EL device according to the present invention may be configured to intermittently apply a relatively high voltage pulse voltage or a relatively low voltage depending on the application.
  • the non-pulse voltage typically 2 to 50 V
  • the organic EL device of the present invention emits light only when the potential of the anode is higher than that of the cathode. Therefore, the voltage applied to the organic EL device of the present invention may be DC or AC, and the waveform and period of the applied voltage may be appropriate.
  • the organic EL device of the present invention in principle, increases or decreases in luminance or blinks repeatedly according to the waveform and cycle of the applied alternating current.
  • the organic EL device of the present invention usually has a wavelength of 550 nm or more, and more specifically, 550 to 650, although it depends on the light-emitting characteristics of the coumarin derivative and the type of host compound used in combination. It has an emission maximum in the red or near red range of nm.
  • the luminescence usually has X in the range of 0.4 to 0.7 and y in the range of 0.3 to 0.6 in the xy chromaticity coordinates.
  • the coumarin derivative used in the present invention emits red to orange light in the organic EL device, and therefore, in the light emitting layer 4, a blue region or green light capable of emitting complementary blue to green light is emitted.
  • Light emitting pole in the area By using another light emitting compound having a large size as described above in combination, white light can be emitted from the organic EL element.
  • the layer containing the coumarin derivative and the layer containing the coumarin derivative are adjusted with the color purity of white light as an index, for example, while adjusting the film thickness and / or the content of the luminescent compound.
  • a single-layer light-emitting layer 4 is formed by laminating a layer containing a light-emitting compound that emits green light, or by mixing a mixture of both with an appropriately adjusted mixing ratio. Although it depends on the kind of the luminescent compound to be combined, the white light thus obtained usually has X in the range of 0.25 to 0.4, and y in the xy chromaticity coordinates. It is in the range of 5 to 0.4.
  • the organic EL device of the present invention Since the organic EL device of the present invention is excellent in luminous efficiency and durability, it has various uses in luminous bodies and information display devices for visually displaying information.
  • the luminous body using the organic EL element of the present invention as a light source has low power consumption and can be configured in a lightweight panel shape. Therefore, in addition to a general illumination light source, for example, a liquid crystal element, a copying machine, Equipment, electrophotographic equipment, computers and their applied equipment, industrial control equipment, electronic measuring equipment, analytical equipment, general instruments, communication equipment, medical electronic measuring equipment, general consumer and commercial electronic equipment, and It is extremely useful as an energy-saving and space-saving light source and information display element in vehicles, ships, aircraft, spacecraft, and other general equipment, aircraft control equipment, interiors, signboards, and signs.
  • a general illumination light source for example, a liquid crystal element, a copying machine, Equipment, electrophotographic equipment, computers and their applied equipment, industrial control equipment, electronic measuring equipment, analytical equipment, general instruments, communication equipment, medical
  • the organic EL device of the present invention is used, if necessary, in combination with a filter that blocks light having a wavelength of 585 nm or less, and usually formed into a panel shape according to the intended use.
  • the organic EL device of the present invention is used for lighting equipment, for example, dashboards for vehicles, ships, aircraft, spacecrafts, etc., computer terminals, television receivers, recorders, game machines, watches, telephones, and communication devices.
  • information display devices such as car navigation devices, oscilloscopes, radars, sonars, signboards, signs, etc.
  • the organic EL device of the present invention that emits white light alone or in combination with an organic EL device that emits blue or green light, as required, can be used as a general-purpose simple matrix method or active matrix. Drive by applying the trick method.
  • the coumarin derivative of the present invention in order to use the coumarin derivative of the present invention as a laser active substance, it is necessary to purify it in the same manner as in the case of constructing a known dye-based laser oscillator, dissolve it in an appropriate solvent, and if necessary, After adjusting the pH to an appropriate level, it is sealed in a dye cell in a laser oscillator.
  • the coumarin derivative of the present invention not only provides an amplification gain in an extremely wide wavelength range in the visible region, but also has high light resistance and is hardly deteriorated even when used for a long time, as compared with known coumarin derivatives. There is.
  • the coumarin derivative of the present invention has an absorption maximum in the visible region and substantially absorbs visible light
  • a material for polymerizing the polymerizable compound by exposing it to visible light and a solar cell are disclosed. It has a wide variety of uses as a material for sensitization, a chromaticity adjusting material for optical filters, and a material for dyeing various kinds of clothing.
  • most of the coumarin derivatives of the present invention have absorption maximum wavelengths such as gas lasers such as argon ion lasers and krypton ion lasers, semiconductor lasers such as CdS lasers, and distributed feedback.
  • solid-state lasers such as solid-state lasers, such as a solid-state or distributed Bragg reflection type Nd-YAG laser
  • a photosensitizer By blending it as a photosensitizer with a photopolymerizable composition using such a visible laser as an exposure light source, it can be used in the fields of information recording such as facsimile, copier, printer, etc., flexographic plate making, gravure plate making, etc. It can be used extremely advantageously in the field of printing, and in the field of printed circuits such as photo resists.
  • the coumarin derivative of the present invention may be used, if necessary, together with one or more other materials that absorb light in the ultraviolet, visible, and / or infrared regions.
  • the melting point of the coumarin derivative of this example was 250 to 255 ° C. Furthermore, when the visible absorption spectrum (methanol solution) and the fluorescence spectrum (methylene chloride solution) were measured according to a conventional method, the coumarin derivatives of this example showed wavelengths of 501 nm and 6 nm, respectively. It showed an absorption maximum and a fluorescence maximum at 49 nm.
  • the chemical shift 6 ( ⁇ ⁇ m, TMS) is 1.26 (6H, s), 1.47 (6H, s), 1.70 (2H, t), 1.76 (2H, t), 3.5 0 to 3.90 (4H, m), 6.78 (1H, d), 6.86 (1H, dd), 7.39 ( ⁇ , s), 7.60 (1H, d) .7.80 (1H, d), 8.02 (1H, d), 8.23 (1H, s), 8.31 (1H, s) And 8.6 1 (1 H, s) A peak was observed at the position.
  • the coumarin derivative of this example which has an absorption maximum and a fluorescence maximum in the visible region, has a wide variety of uses in various fields requiring organic compounds having such properties, including luminescent agents for organic EL devices. .
  • Example 2 Coumarin derivative
  • the melting point of the coumarin derivative of this example was 240 to 245 ° C. Furthermore, when the visible absorption spectrum (methylene chloride solution) and the fluorescence spectrum (methylene chloride solution) were measured according to a conventional method, the coumarin derivative of this example was found to have a wavelength of 479 nm. And the absorption maximum and the fluorescence maximum at 63 nm.
  • the coumarin derivative of this example having an absorption maximum and a fluorescence maximum in the visible region has a wide variety of uses in various fields requiring an organic compound having such properties, including a luminescent agent for an organic EL device. .
  • Example 3 Coumarin derivative
  • the reaction was carried out in the same manner as in Example 1 except that the compound represented by Chemical Formula 66 was used instead of the compound represented by Chemical Formula 64, and then the reaction mixture was purified. A bright red crystal of a coumarin derivative was obtained.
  • the melting point of the coumarin derivative of this example was 235 ° C. Furthermore, when the visible absorption spectrum (methylene chloride solution) and the fluorescence spectrum (methylene chloride solution) were measured according to the conventional methods, the coumarin derivative of this example had wavelengths of 505 nm and 675 nm, respectively. Shows the absorption maximum and the fluorescence maximum.
  • the coumarin derivative of this example having an absorption maximum and a fluorescence maximum in the visible region has a wide variety of uses in various fields requiring an organic compound having such properties, including a luminescent agent for an organic EL device. .
  • Example 4 Coumarin derivative
  • Reaction was performed in the same manner as in Example 2 except that the compound represented by Chemical Formula 64 was used instead of the compound represented by Chemical Formula 66, and then the reaction mixture was purified. Light orange crystals of the coumarin derivative were obtained.
  • the melting point of the coumarin derivative of this example was 278 ° C. as measured according to a conventional method. Further, when the visible absorption spectrum (methanol solution) and the fluorescence spectrum (methylene chloride solution) were measured according to the usual methods, the coumarin derivative of this example was found to have wavelengths of 474 nm and 606 ⁇ , respectively. m shows the absorption maximum and the fluorescence maximum. Further, when the 1 H-NMR spectrum of the dimethyl 0) 6 sulfoxide solution was measured, the chemical shift ⁇ ( ⁇ pm, TMS) was 1.31 (6 H, s) and 1. 5 6 (6 H, s), 1.7
  • the coumarin derivative of this example which has an absorption maximum and a fluorescence maximum in the visible region, has a wide variety of uses in various fields requiring an organic compound having such properties, such as a luminescent agent for an organic EL device. Having.
  • Example 5 Coumarin derivative
  • the reaction was carried out in the same manner as in Example 1 except that the compound represented by Chemical Formula 67 was used instead of the compound represented by Chemical Formula 64, and then the reaction mixture was purified. A dark green crystal of the coumarin derivative was obtained.
  • the melting point of the coumarin derivative of this example was 278 to 284 ° C. Further, when the visible absorption spectrum (methylene chloride solution) and the fluorescence spectrum (methylene chloride solution) were measured according to a conventional method, the coumarin derivative of this example was found to have wavelengths of 504 nm and 6778, respectively. The absorption maximum and the fluorescence maximum were shown at nm.
  • the coumarin derivative of this example which has an absorption maximum and a fluorescence maximum in the visible region, can be used in a wide variety of applications in various fields that require organic compounds having such properties, including organic luminescent agents.
  • Have. Example 6 Coumarin derivative
  • the reaction was carried out in the same manner as in Example 2 except that the compound represented by Chemical Formula 68 was used instead of the compound represented by Chemical Formula 66, and then the reaction mixture was purified. A bright red-brown crystal of the coumarin derivative was obtained.
  • the melting point of the coumarin derivative of this example was 289 to 294 ° C. as measured according to a conventional method. Furthermore, when the visible absorption spectrum (methylene chloride solution) and the fluorescence spectrum (methylene chloride solution) were measured according to the usual methods, the coumarin derivatives of this example showed wavelengths of 484 nm and 649 nm, respectively. The absorption maximum and the fluorescence maximum were shown at nm.
  • the coumarin derivative of this example having an absorption maximum and a fluorescence maximum in the visible region is widely used in various fields that require an organic compound having such properties, including a luminescent agent for an organic E1 element. It has applications.
  • Example 7 Coumarin derivative
  • the reaction mixture was purified in the same manner as in Example 2 except that the compound represented by Chemical Formula 67 was used instead of the compound represented by Chemical Formula 66, and the reaction mixture was purified. An orange crystal of the coumarin derivative was obtained.
  • the melting point of the coumarin derivative of this example was 2443 to 251 ° C. Furthermore, when the visible absorption spectrum (methylene chloride solution) and the fluorescence spectrum (methylene chloride solution) were measured according to the usual methods, the coumarin derivative of this example was found to have wavelengths of 480 nm and 623, respectively. The absorption maximum and the fluorescence maximum were shown at nm.
  • the coumarin derivative of this example which has an absorption maximum and a fluorescence maximum in the visible region, can be used in a wide variety of applications in various fields that require organic compounds having such properties, including organic luminescent agents.
  • the reaction was carried out in the same manner as in Example 1 except that the compound represented by Chemical Formula 68 was used instead of the compound represented by Chemical Formula 64, and then the reaction mixture was purified. An orange crystal of the coumarin derivative was obtained.
  • the melting point of the coumarin derivative of this example was 248 to 251 ° C as measured according to a conventional method.
  • the visible absorption spectrum When the torr (methylene chloride solution) and the fluorescence spectrum (methylene chloride solution) were measured, the coumarin derivative of this example showed an absorption maximum and a fluorescence maximum at wavelengths of 509 nm and 582 nm, respectively.
  • the coumarin derivative of this example having an absorption maximum and a fluorescence maximum in the visible region has a wide variety of uses in various fields requiring an organic compound having such properties, including a luminescent agent for an organic EL device. .
  • Example 9 Coumarin derivative
  • the reaction was carried out in the same manner as in Example ⁇ except that the compound represented by Chemical Formula 69 was used instead of the compound represented by Chemical Formula 64, and then the reaction mixture was purified. Black crystals of the coumarin derivative were obtained.
  • the melting point of the coumarin derivative of this example was 2 55 to 260 ° C. Furthermore, when the visible absorption spectrum (methylene chloride solution) and the fluorescence spectrum (methylene chloride solution) were measured according to a conventional method, the coumarin derivative of this example showed wavelengths of 511 nm and 564 nm, respectively. The absorption maximum and the fluorescence maximum were shown at nm. Further, when the 1 H—NMR spectrum of the solution of the dye solution was measured, the chemical shift ⁇ 5 (ppm, TMS) was 1.31 (6H, s) and 1.56 (6H).
  • the coumarin derivative of this example having an absorption maximum and a fluorescence maximum in the visible region has a wide variety of uses in various fields requiring an organic compound having such properties, including a luminescent agent for an organic EL device. .
  • Example 10 Coumarin derivative
  • the reaction was carried out in the same manner as in Example 2 except that the compound represented by Chemical Formula 69 was used instead of the compound represented by Chemical Formula 66, and then the reaction mixture was purified. A dark brown crystal of the coumarin derivative was obtained.
  • the melting point of the coumarin derivative of this example was 2
  • the coumarin derivative of this example having an absorption maximum and a fluorescence maximum in the visible region has a wide variety of uses in various fields requiring an organic compound having such properties, including a luminescent agent for an organic EL device. .
  • the reaction was carried out in the same manner as in Example 2 except that the compound represented by Chemical Formula 70 was used instead of the compound represented by Chemical Formula 66, and then the reaction mixture was purified. A red crystal of the coumarin derivative was obtained.
  • the melting point of the coumarin derivative of this example was 288 to 292 ° C. Furthermore, when the visible absorption spectrum (methanol solution) and the fluorescence spectrum (methylene chloride solution) were measured according to a conventional method, the coumarin derivative of this example showed wavelengths of 476 nm and 60 nm, respectively. The absorption maximum and the fluorescence maximum were shown at 3 nm. In addition, the 1 H—NMR spectrum of a solution of porcine form 1d / trifluroacetic acid was measured.
  • the coumarin derivative of this example having an absorption maximum and a fluorescence maximum in the visible region has a wide variety of uses in various fields requiring an organic compound having such properties, including a luminescent agent for an organic EL device. .
  • Example 12 Coumarin derivative
  • coumarin derivative of the present invention has slightly different charging conditions and yields depending on the structure, for example, all of the examples including those represented by the chemical formulas 1 to 62 other than those described above were used in Examples. A desired amount can be produced by the methods of Examples 1 to 12 or according to those methods.
  • Example 13 Luminescent agent for organic EL device
  • the melting point of the coumarin derivative of this example was 263 ° C. as measured according to a conventional method. Furthermore, when the visible absorption spectrum (methanol solution) and the fluorescence spectrum (methylene chloride solution) were measured according to the conventional methods, the coumarin derivative of this example was found to have a wavelength of 505 nm and a wavelength of 613 ⁇ , respectively. m shows the absorption maximum and the fluorescence maximum.
  • Example 14 Luminescent Agent for Organic EL Device
  • the melting point of the coumarin derivative of this example was 285 ° C. as measured by a conventional method. Furthermore, when the visible absorption spectrum (methanol solution) and the fluorescence spectrum (methylene chloride solution) were measured according to the conventional methods, the coumarin derivative of this example was found to have a wavelength of 503 nm and a wavelength of 568 ⁇ , respectively. m shows the absorption maximum and the fluorescence maximum.
  • the coumarin derivative of this example was found to have wavelengths of 501 nm and 64 nm, respectively. It showed an absorption maximum and a fluorescence maximum at 9 nm.
  • Example 16 Organic EL Device Luminescent Agent
  • the melting point of the coumarin derivative of this example was 240 to 245 ° C.
  • the visible absorption spectrum Toluene (methanol solution) and fluorescence spectrum (methylene chloride solution) were measured, and the coumarin derivative of this example showed an absorption maximum and a fluorescence maximum at wavelengths of 479 nm and 623 nm, respectively. .
  • the melting point of the coumarin derivative of this example was 235 ° C. Further, when the visible absorption spectrum (methanol solution) and the fluorescence spectrum (methylene chloride solution) were measured according to a conventional method, the coumarin derivative of this example was found to have a wavelength of 505 nm and a wavelength of 675 ⁇ , respectively. m shows the absorption maximum and the fluorescence maximum.
  • Example 1 Luminescent agent for organic EL device
  • the melting point of the coumarin derivative of this example was 2
  • the coumarin derivative of this example showed wavelengths of 474 nm and 60 nm, respectively. 4 ⁇ m shows the absorption maximum and the fluorescence maximum.
  • Example 1 9 Luminescent agent for organic EL device
  • the melting point of the coumarin derivative of this example was 278 ° C. as measured according to a conventional method. Further, when the visible absorption spectrum (methanol solution) and the fluorescence spectrum (methylene chloride solution) were measured according to the usual methods, the coumarin derivative of this example was found to have wavelengths of 490 nm and 566 ⁇ , respectively. m shows the absorption maximum and the fluorescence maximum.
  • the coumarin derivative of this example having excellent luminescence characteristics is extremely useful as a luminescent agent for an organic EL device.
  • a glass substrate 1 having a transparent ITO electrode with a thickness of 100 nm as an anode 2 patterned with a water vapor is ultrasonically cleaned with a detergent, pure water, acetone and ethanol, dried, and irradiated with ultraviolet light. After treatment with ozone, And fixed to the vacuum evaporation apparatus was evacuated to 1 0- 7 T orr. Next, a tetramer of triphenylamine represented by the chemical formula 77 was deposited on the surface of the glass substrate 1 having the IT0 electrode to a thickness of 60 nm to form a hole injection / transport layer 2. .
  • one of the coumarin derivatives according to the present invention shown in Table 1 and tris (8-quinolinolate) aluminum were used as a light emitting agent at a weight ratio of 1: 100.
  • a light emitting layer 4 by co-evaporation to 20 nm, and further forming an electron injection / transport layer 5 by depositing tris (8-quinolinol) aluminum to a thickness of 40 nm
  • Lithium fluoride and aluminum were deposited in this order to a thickness of 0.5 nm and 160 nm, respectively, to form cathode 6.
  • the entire device was sealed using a glass plate and an ultraviolet curable resin to obtain four types of organic EL devices.
  • the emission spectrum of the organic EL device thus obtained was measured according to a conventional method, and the relationship between the emission luminance and the injection current density or the applied voltage was examined. Calculated. In addition, the relationship between the initial emission Brightness 3 0 0 cd emission brightness when set to Zm 2 and the driving time Investigation and calculation of the lifetime (driving time at which the initial emission luminance is halved).
  • a system was prepared using the compound represented by Formula 8 in place of the coumarin derivative, and this was treated in the same manner as above to serve as a control. Table 1 shows the results.
  • * 1 indicates a measured value when driven at a current density of 11 mA / cm 2 .
  • the emission luminance was about 370 to 520 cd / m 2 .
  • the emission quantum efficiency was as high as about 1.1 to 1.7%.
  • the luminescence continued stably, and no partial dark spot (dark spot) was observed even after the lapse of 1,000 hours from the start of the luminescence.
  • the half-life when driven at a constant current of 300 cd / m 2 which is a practical light emission luminance, was 1,000 hours or more in each case.
  • the lifetime of the organic EL device using the coumarin compounds represented by the chemical formulas 6, 7 and 12 was particularly long, from about 3,000 to 4,000 hours.
  • the organic EL device of the control showed slightly more reddish emission than the organic EL device of this example, but was significantly significant in terms of emission quantum efficiency and lifetime. Was inferior.
  • FIG. 2 schematically shows an example of a simple matrix type display panel (20 electrode rows in the horizontal direction and 30 electrode rows in the vertical direction) mainly comprising the organic EL element of the present invention.
  • a display panel can be manufactured as follows.
  • the anode 14 After forming the anode 14 using the 1 T O transparent electrode, the anode 14 is processed into a strip shape by a wet etching method. Next, a hole injection Z transport layer 16 and a light emitting layer 18 were sequentially formed according to the method of Example 20, and a cathode 20 was formed in a strip shape using a mechanical mask. (Not shown) and the organic EL element is sealed with an ultraviolet curable resin. In addition, in the display panel of this example, in order to suppress the temperature rise during use, the cathode
  • a heat sink or a cooling fan may be attached to the back side of the 20.
  • FIG. 3 shows a display panel manufactured according to the method of Example 21. 1 is an example of an information display device.
  • reference numeral 30 denotes a DC power supply having an output voltage of 4.5 V, and two booster circuits 32 and 34 are connected to its output terminal.
  • the booster circuit 32 can supply a DC voltage in the range of 5 to 12 V, and its output terminal is connected to the driver circuit 36.
  • the other booster circuit 34 is for supplying a constant voltage of 5 V to the microcomputer 38.
  • the microcomputer 38 has an IZO interface 38a for exchanging signals with the outside, a ROM 38b for storing programs, etc., a RAM 38c for storing various data, and various arithmetic operations. Comprising a CPU 38D.
  • the microcomputer 38 is connected to a clock generation circuit 40 for supplying a clock signal of 8 MHz to the microcomputer 38, and two oscillation circuits 42 and 44, respectively.
  • 4 2 and 4 4 are for supplying a microcomputer 38 with a signal of 5 to 50 Hz for controlling the display speed and a signal of 0.2 to 2 kHz for controlling the scanning frequency, respectively. Things.
  • Reference numeral 48 denotes a display panel mainly including the organic EL element of the present invention, which is connected to a microcomputer 38 via driver circuits 36 and 46.
  • the driver circuit 36 is a circuit that controls the application of the DC voltage from the booster circuit 32 to the display panel, and includes a plurality of transistors that are individually connected to the vertical electrode row of the display panel 48. Comprising. Therefore, when one of the transistors in the driver circuit 36 is turned on, the voltage from the booster circuit 32 is applied to the vertical electrode row connected to the transistor.
  • the driver circuit 46 includes a plurality of transistors individually connected to the horizontal electrode row of the display panel 48. When one of the transistors in the driver circuit 46 is turned on, the driver circuit 46 is turned on. Horizontal electrodes connected to transistors The column will be grounded.
  • the information display device of this example is configured as described above, when the transistors in the driver circuits 36 and 46 are turned on according to the instruction of the microcomputer 38, the display panel 48 in the vertical and horizontal directions is turned on. A predetermined voltage is applied between the corresponding electrode rows, and the organic EL element located at the intersection thereof emits light. Therefore, for example, one horizontal electrode row is selected by appropriately controlling the driver circuit 46, and the electrode row is connected to the vertical electrode row by appropriately controlling the driver circuit 36 while grounding that electrode row.
  • the selected transistors are sequentially turned on, the selected horizontal electrode row is scanned in the horizontal direction, and a given pixel is displayed. By repeating such scanning sequentially in the vertical direction, an entire screen can be displayed.
  • the driver circuit 36 in this example has data registers for the electrode rows, it is preferable to drive the transistors based on the stored data.
  • the information to be displayed is supplied from the outside in accordance with the display speed and cycle, or the information is stored in the ROM 38b in advance for information having a fixed pattern such as character information. This may be used as data.
  • a received signal is separated into a horizontal synchronization signal and a vertical synchronization signal according to a horizontal frequency and a vertical frequency based on a broadcasting standard, and a video signal is also displayed.
  • the signal is converted to a digital signal corresponding to the number of pixels on the display panel 48.
  • the present invention is based on the discovery of a novel industrially useful property of a coumarin derivative having a chalcone-like structure in a molecule.
  • the coumarin derivative used in the present invention has an emission maximum in the visible region, particularly in the red region or near-red region, and forms a stable thin film in a glassy state, and thus is extremely useful as a luminescent agent for organic EL devices. .
  • the organic EL device of the present invention using such a luminescent agent is excellent in luminous efficiency and durability, it can be used in combination with or without a filter for blocking light having a wavelength of 585 nm or less.
  • As a light source that emits orange light or white light it can be extremely advantageously used in a light-emitting body in general lighting and in a wide variety of information display devices that visually display information such as image information and character information.

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

Abstract

La présente invention concerne un dérivé de coumarine spécifique, qui présente une structure de type chalcone dans sa molécule, un matériau luminescent destiné à un élément d'électroluminescence organique, qui comprend ledit dérivé de coumarine spécifique, ainsi qu'un élément d'électroluminescence organique comprenant ledit matériau luminescent. La présente invention concerne également un dispositif d'affichage d'informations, qui utilise ledit élément d'électroluminescence organique. Le dérivé de coumarine spécifique selon cette invention présente une luminescence maximale dans une région rouge ou une région proche infrarouge.
PCT/JP2001/004219 2000-05-24 2001-05-21 Derive de coumarine et son utilisation Ceased WO2001090098A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2000153741 2000-05-24
JP2000-153408 2000-05-24
JP2000153408A JP2001329257A (ja) 2000-05-24 2000-05-24 有機電界発光素子用発光剤とその用途
JP2000-153741 2000-05-24
JP2001-40690 2001-02-16
JP2001040690A JP4982642B2 (ja) 2000-05-24 2001-02-16 クマリン誘導体

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007132948A1 (fr) * 2006-05-17 2007-11-22 Sumitomo Chemical Company, Limited Composé de cinnamoyle et leur utilisation
US7514158B2 (en) * 2001-12-13 2009-04-07 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Coumarin compound

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0032670A1 (fr) * 1980-01-19 1981-07-29 Bayer Ag Systèmes pour collection de lumière et utilisation de dérivés de coumarine comme convertisseurs d'énergie dans de tels systèmes
JPH07258566A (ja) * 1994-03-25 1995-10-09 Nippon Kanko Shikiso Kenkyusho:Kk クマリン誘導体及びホトポリマー用増感色素
JPH09208574A (ja) * 1996-02-08 1997-08-12 Mitsui Toatsu Chem Inc ビスクマリン化合物およびその用途
JPH09268185A (ja) * 1996-04-03 1997-10-14 Mitsui Toatsu Chem Inc クマリン化合物およびその用途

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0032670A1 (fr) * 1980-01-19 1981-07-29 Bayer Ag Systèmes pour collection de lumière et utilisation de dérivés de coumarine comme convertisseurs d'énergie dans de tels systèmes
JPH07258566A (ja) * 1994-03-25 1995-10-09 Nippon Kanko Shikiso Kenkyusho:Kk クマリン誘導体及びホトポリマー用増感色素
JPH09208574A (ja) * 1996-02-08 1997-08-12 Mitsui Toatsu Chem Inc ビスクマリン化合物およびその用途
JPH09268185A (ja) * 1996-04-03 1997-10-14 Mitsui Toatsu Chem Inc クマリン化合物およびその用途

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7514158B2 (en) * 2001-12-13 2009-04-07 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Coumarin compound
WO2007132948A1 (fr) * 2006-05-17 2007-11-22 Sumitomo Chemical Company, Limited Composé de cinnamoyle et leur utilisation
JP2007308402A (ja) * 2006-05-17 2007-11-29 Sumitomo Chemical Co Ltd シンナモイル化合物及びその用途

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