KR20020084282A - Coumarin Derivative, Process for Producing the Same, and Luminescent Agent and Luminescent Element Each Containing the Same - Google Patents

Abstract

It is an object of the present invention to provide a functional organic material useful as a light absorbing agent and a light emitting agent and its use, and includes a coumarin derivative and a coumarin derivative having a specific structure and physical properties. Light-emitting devices and uses thereof, coumarin compounds having an aldehyde group and a hydrocarbon group in positions 3 and 4 respectively in the coumarin skeleton, and having a urolidine skeleton in positions other than positions 3 and 4, and adjacent carbon atoms The above object is solved by providing a method for producing a coumarin derivative via a step of reacting a hydrocarbon formed by combining an ethol group and a primary amino group.

Description

Coumarin derivatives, methods for manufacturing the same, light emitting agents and light emitting devices using the same {Coumarin Derivative, Process for Producing the Same, and Luminescent Agent and Luminescent Element Each Containing the Same}

With the advent of the multimedia age, organic EL devices are in the spotlight as the next generation display devices. Currently, CRTs are mainly used in relatively large information displays such as computer terminals and televisions. However, the CRT is large in volume and weight, and has a high operating voltage. Therefore, the CRT is not suitable for a consumer device or a small device that emphasizes portability. Smaller devices require thinner, lighter panel shapes with lower operating voltages and lower power consumption. Currently, liquid crystal devices have been used because of their low operating voltage and relatively low power consumption. However, since the contrast varies depending on the viewing angle of the information display apparatus using the liquid crystal element, a clear display is not obtained unless it is read in a range of angles, and since a backlight is usually required, power consumption is very low. There is a problem that it does not become small. Organic EL devices have emerged as display devices that solve these problems.

An organic EL device is usually formed by inserting a light emitting layer containing a light emitting compound between an anode and a cathode, and injecting holes and electrons into the light emitting layer by applying a DC voltage between the anode and the cathode, respectively, and recombining them. A light emitting device is used to generate an excited state of a light emitting compound and to use light emission such as fluorescence or phosphorescence emitted when the excited state returns to the ground state. The organic EL device is characterized in that the color of light emission can be appropriately changed by selecting a suitable compound as a host compound and changing a guest compound (dopant) to be combined with the host compound in forming the light emitting layer. have. In addition, depending on the combination of the host compound and the guest compound, there is a possibility that the luminance and lifetime of light emission can be greatly improved. In addition, since the organic EL element emits light by itself, the information display device using the organic EL element does not depend on the viewing angle and does not require a backlight, thereby reducing the power consumption. It is known.

However, most of the organic EL devices proposed so far have low durability and, for example, are mounted in a vehicle in which vibrations or high temperatures are inevitable, and thus there is a problem that the luminance decreases in a short time when used in a harsh environment.

In view of such a situation, it is an object of the present invention to provide a functional organic material useful as a light absorbing agent and a light emitting agent, particularly a luminescent organic compound useful in an organic EL device aiming at high durability and its use.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to novel coumarin derivatives, and more particularly, to coumarin derivatives useful for organic electroluminescent devices (hereinafter, abbreviated as "organic EL devices").

1 is a schematic diagram of an organic EL device according to the present invention;

2 is a schematic view of a display panel according to the present invention;

3 is a block diagram of an information display apparatus according to the present invention;

As a result of the present inventor's focus on coumarin derivatives, the present inventors have conducted intensive studies and studies. As a result, the hydrocarbon group is bonded to position 4 in the coumarin skeleton, and the urolidine skeleton and the benzothiazole skeleton are provided at positions other than the position 4. It has been found that the coumarin derivative having a light emits relatively long wavelengths of visible light, in particular, visible light of a green region to a red region in an organic EL device, and this light emission lasts for a long time and stably. Since these coumarin derivatives have an absorption maximum in the visible region and have a property of substantially absorbing visible light, they need to be added to the field of organic EL devices as light absorbers and light-emitting agents and require organic compounds having such properties. For example, photochemical polymerization, solar cells, dyeing, optical filters, dye lasers have been found to be useful in all fields.

This invention solves the said subject by providing the coumarin derivative which has a hydrocarbon group couple | bonded with the position 4 in a coumarin skeleton, and has a urolidine skeleton and a benzothiazole skeleton in a site other than position 4.

Moreover, this invention solves the said subject by providing the light absorbing agent containing such a coumarin derivative.

Moreover, this invention solves the said subject by providing the light emitting agent containing such a coumarin derivative.

Moreover, this invention solves the said subject by providing the organic electroluminescent element which uses such a coumarin derivative.

Moreover, this invention solves the said subject by providing the use for the display panel of organic electroluminescent element using such a coumarin derivative.

Moreover, this invention solves the said subject by providing the use of the organic electroluminescent element which uses such a coumarin derivative for the information display apparatus.

In addition, the present invention is a compound having an aldehyde group and a hydrocarbon group at positions 3 and 4 in the coumarin skeleton, respectively, and having a urolidine skeleton at sites other than positions 3 and 4, and adjacent carbon atoms. The above object is solved by providing a method for producing a coumarin derivative via a step of reacting an aromatic hydrocarbon formed by combining an thiool group and a primary amino group.

In addition, most of the coumarin derivatives of the present invention exhibit a glass transition point near 100 to 110 ° C. In recent studies on organic EL devices, it is said that in order to fabricate highly durable organic EL devices, it is necessary to use a luminescent compound having a high glass transition point. Considering the trend of this study, it was surprising that even a luminescent compound having a low glass transition point, such as a coumarin derivative according to the present invention, can be fabricated with an excellent organic EL device depending on the structure of the luminescent compound.

The present invention relates to a coumarin derivative having a hydrocarbon group bonded to position 4 in the coumarin skeleton and having a urolidine skeleton and a benzothiazole skeleton at a position other than position 4. In another aspect, the present invention relates to a coumarin derivative having a luminescence maximal band in the visible region and having a glass transition point in the range of 100 to 110 ° C. As described above, the coumarin derivative has an absorption maximum in the visible region, substantially absorbs visible light, and has a maximum emission region such as a fluorescent maximum in the visible region. It is based on the original knowledge of emitting visible light in the green to red region. Therefore, any coumarin derivative can be advantageously used according to the present invention as long as it has such a structure and / or physical properties. The maximal emission wavelength of the coumarin derivative is determined by measuring, for example, the fluorescence spectrum or the phosphorescence spectrum according to the usual usage, and the glass transition point is, for example, general-purpose differential scanning calorimetry (hereinafter referred to as "DSC analysis"). Can be determined).

As an example of such a coumarin derivative, what is represented by General formula (1) is mentioned, for example.

(Formula 1)

In General formula 1, R <_1> represents a hydrocarbon group, and this hydrocarbon group may have one or more substituents. As a hydrocarbon group in R <_1> , a methyl group, an ethyl group, a propyl group, isopropyl group, 1-propenyl group, 2-propenyl group, butyl group, isobutyl group, sec-butyl group, tert- butyl group, 2 -C5 or less carbon atoms, such as a butenyl group and a 1,3-butadienyl group, usually a C1-C4 aliphatic hydrocarbon group, a cychloropropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, cyclohexenyl Alicyclic hydrocarbon groups such as a group; Aromatic hydrocarbon groups, such as a phenyl group o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, m- cumenyl group, p-cumenyl group, and a diphenyl group, are mentioned. One or a plurality of hydrogen atoms in such a hydrocarbon group is, for example, a methoxy group, trifluoromethoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, ether groups such as tert-butoxy group, pentyloxy group, isopentyloxy group, phenoxy group and benzyloxy group; Ester groups such as acetoxy group, trifluoroacetoxy group, benzoyloxy group, methoxycarbonyl group, trifluoromethoxycarbonyl group, ethoxycarbonyl group and propoxycarbonyl group; Moreover, you may substitute by halogen groups, such as a fluorine group, a chloro group, a bromo group, and an iodine group.

R ₂ to R ₅ in General Formula 1 each independently represent a hydrogen atom or an aliphatic hydrocarbon group. The aliphatic hydrocarbon group in R ₂ to R ₅ is 5 or less carbon atoms, usually 1 to 4 carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group and tert-butyl groups. Depending on the application, the organic EL device is preferably a coumarin derivative in which all of R ₂ to R ₅ are aliphatic hydrocarbon groups, and coumarin derivatives in which R ₂ to R ₅ are all methyl groups are particularly excellent in physical properties and economy.

Z in General formula 1 represents the aromatic ring condensed to a thiazole ring. As an individual aromatic ring, Monocyclic hydrocarbons, such as benzene; Condensed polycyclic hydrocarbons such as naphthalene, anthracene, phenanthrene, naphthacene and chrysene; And ring-type hydrocarbons such as biphenyl, taphenyl, phenylnaphthalene and naphthyl naphthalene.

As a specific example of the coumarin derivative by this invention, what is shown, for example by Formula (1)-Formula (27) is mentioned. All of them have an absorption maximum in the visible region, and in addition to substantially absorbing visible light, they also have a maximal emission region such as a fluorescent maximum in the visible region. This is remarkable.

The coumarin derivative according to the present invention can be prepared by various methods, but if it is important to focus on economics, for example, the aldehyde group and the hydrocarbon group are bonded to the 3 and 4 positions in the coumarin skeleton, respectively, and the 3 position And a step of reacting a compound having a urolidine skeleton at a position other than position 4 with a monocyclic, condensed polycyclic, or cyclic hydrocarbon group formed by bonding a thiol group and a primary amino group to adjacent carbon atoms. The method of doing is preferable. In this method, for example, by reacting a compound represented by the general formula (2) having R ₁ to R ₅ corresponding to the general formula (1) with a compound represented by the general formula (3) having a Z corresponding to the general formula (1) The coumarin derivatives of the present invention are produced in the desired yields.

(Formula 2)

(Formula 3)

That is, an appropriate amount of the compounds represented by the formulas (2) and (3) in the reaction vessel (usually before and after equimolar) is dissolved in an appropriate solvent, if necessary, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, Basic compounds such as sodium bicarbonate, sodium carbonate, ammonia, triethylamine, piperidine, pyridine, pyrrolidine, aniline, N, N-dimethylaniline and N, N-diethylaniline; Acidic compounds such as hydrochloric acid, sulfuric acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoric acid, trifluoromethanesulfonic acid, acetic anhydride; After adding Lewis acid compounds such as aluminum chloride, zinc chloride, tin tetrachloride, titanium tetrachloride, and the like, the mixture is reacted at ambient temperature or above the ambient temperature while stirring by heating under reflux.

Examples of the solvent include hydrocarbons such as pentane, hexane, cyclohexane, octane, benzene, toluene and xylene; Halides such as carbon tetrachloride, chloroform, 1,2-dichloroethane, 1,2-dibromoethane, trichloroethylene, tetrachloroethylene, chlorobene, bromobenzene and α-dichlorobenzene; Methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutyl alcohol, isopentyl alcohol, cyclohexanol, ethylene glycol, propylene glycol, 2-methoxyethanol, 2-ethoxyethanol Alcohols and phenols such as phenol, benzyl alcohol, cresol, diethylene glycol, triethylene glycol and glycerin; Diethyl ether, diisopropyl ether, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, anisole, 1,2-dimethoxyethane, diethylene glycol, dimethyl ether, dicyclohexyl-18-crown- Ethers such as 6, methyl carbitol and ethyl carbitol; Acetic acid, acetic anhydride, trichloroacetic acid, trifluoroacetic acid, propionic anhydride, ethyl acetate, butyl carbonate, ethylene carbonate, propylene carbonate, formamide, N-methylformamide, N, N-dimethylformamide, N-methylacetamide Acids and acid derivatives such as N, N-dimethylacetamide and hexamethyl phosphate triamide; Nitriles such as acetonitrile, propionitrile, succinonitrile and benzonitrile; Nitro compounds such as nitromethane and nitrobenzene; Sulfur-containing compounds, such as dimethyl sulfoxide and sulfolane, water, etc. are mentioned, These are used combining suitably as needed.

In the case of using a solvent, in general, when the amount of the solvent increases, the reaction efficiency decreases. On the contrary, when the solvent decreases, it is difficult to uniformly heat and stir, and side reactions are likely to occur. Therefore, it is preferable that the amount of the solvent is usually 5 to 50 times up to 100 times the total raw material compound in weight ratio. Depending on the type of raw compound and the reaction conditions, the reaction is completed within 10 hours and usually within 0.5 to 5 hours. The progress of the reaction can be monitored by a general method such as thin layer chromatography, gas chromatography, high performance liquid chromatography, or the like. All of the coumarin derivatives represented by the formulas (1) to (27) can be produced in a desired amount by this method. For reference, all of the compounds represented by the general formulas (2) and (3) can be obtained by a general-purpose method for preparing a flexible compound, and may be used as it is if there is a commercially available product.

The coumarin derivatives thus obtained are usually dissolved, extracted, separated, decanted, filtered, concentrated, thin layer chromatography, column chromatography, gas chromatography, high performance liquid chromatography, distillation, sublimation, crystallization, etc. prior to use It is prepared by a general-purpose method for purifying analogue compounds, and if necessary, these methods are applied in combination. Although it also depends on the use of a coumarin derivative, when using it for an organic EL element or a dye laser, it is preferable to refine | purify highly by methods, such as distillation, crystallization, and / or sublimation, before use. Among them, the sublimation is particularly excellent because the crystal of high purity is easily obtained by one operation, and there is little loss of the coumarin derivative due to the operation, and no solvent is supplied during the crystal. The sublimation method to be applied may be an atmospheric sublimation method or a decompression sublimation method, but the latter decompression sublimation method is usually employed. In order to sublimate the coumarin derivative of the present invention under reduced pressure, for example, an appropriate amount of coumarin derivative is placed in a sublimation purification apparatus, and the coumarin derivative is kept at a reduced pressure of less than 10 ^-2 Torr, specifically, 10 ^-3 Torr or less. It is heated to a temperature as low as possible, preferably below the melting point, in order to prevent decomposition. If the purity of the coumarin derivatives provided to the sublimation tablets is relatively low, the sublimation rate is suppressed by decreasing the degree of decompression or heating so that impurities are not mixed, and if the coumarin derivatives are difficult to sublimate, rare gases, etc. Sublimation is accelerated by venting the inert gas. The size of the crystal obtained by sublimation can be controlled by adding or subtracting the temperature of the condensation surface in the sublimation purification apparatus. A relatively large crystal can be obtained by gradually crystallizing the condensation surface at a temperature slightly lower than the heating temperature.

Referring to the use of the coumarin derivative according to the present invention, as described above, the coumarin derivative of the present invention has an absorption maximum in the visible region and substantially absorbs visible light, and also has a maximum emission region in the visible region. Since it has the property of emitting light, it has various uses as a light absorbing agent and a light emitting agent in various fields which require an organic compound having such a property. One of the most important uses is as a functional organic material in organic electronics, especially as a light emitting layer material in organic EL devices.

First, the use of the coumarin derivative according to the present invention in the organic EL device will be described. In the present invention, the organic EL device refers to an electroluminescent device using the coumarin derivative as described above, and is particularly positive. A positive electrode for applying a voltage, a negative electrode for applying a negative voltage, a light emitting layer for recombining holes and electrons to extract light emission, and a hole injection / injecting and transporting holes from the anode, if necessary, Single layer and stacked organic EL devices comprising a transport layer, an electron injection / transport layer that injects and transports electrons from a cathode, and a hole block layer for preventing holes from moving from the light emitting layer to the electron injection / transport layer are important applications. Becomes

As is well known, the operation of an organic EL device is essentially a process of injecting electrons and holes from an electrode, a process of moving electrons and holes in a solid, and recombination of electrons and holes to generate singlet or triplet excitons. And the process of excitons emitting light, and these processes are no different in freezing of a single layer organic EL element and a stacked organic EL element. However, in the single-layered organic EL device, the characteristics of the above four steps can be improved only by changing the structure of the luminescent compound. In the stacked-type organic EL device, the functions required in each process are shared among a plurality of materials. At the same time, since each material can be optimized independently, it is easier to achieve the desired performance when it is configured in a lamination type than in a single layer type.

Thus, the organic EL device of the present invention will be described with reference to the stacked organic EL device as an example. FIG. 1 is a schematic diagram of the stacked organic EL device according to the present invention. In the drawings, 1 is a substrate, and soda glass, barium silicate glass, It is glass, such as an aluminosilicate glass, general-purpose board | substrates material, such as plastics, such as polyester, polycarbonate, polysulfone, polymethylmethacrylate, polypropylene, polyethylene, ceramics, such as quartz, ceramics, plate shape, a sheet It forms and uses in phase or film form, and these are used by laminating suitably as needed. Preferred substrate materials are transparent glass and plastic, and opaque ceramics such as silicon are used in combination with transparent electrodes. When it is necessary to adjust the chromaticity of light emission, chromaticity adjusting means, such as a filter film, a chromaticity conversion film, a dielectric reflection film, is provided in the place of the board | substrate 1, for example.

2 is an anode, an electrically low resistivity, and a metal or a conductive compound having a high light transmittance over all visible areas, for example, vacuum deposition, sputtering, chemical vapor deposition (CVD), electronic layer epitaxy ( ALE), coating, immersion or the like, to be in close contact with one side of the substrate 1, so that the resistivity of the anode 2 is 1 kΩ / □ or less, preferably from 5 to 50Ω / □, the thickness 10 ~ It is formed by forming into a single layer or a multilayer of 1000 nm, preferably 50 to 500 nm. Examples of the conductive material for the anode 2 include metals such as gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten and aluminum, zinc oxide, tin oxide, indium oxide, and tin oxide. And metal oxides such as a mixed system of indium oxide (hereinafter abbreviated as "ITO"), and conductive oligomers and conductive polymers made of repeating units such as aniline, thiophene and pyrrole. Among these, ITO is easily obtained with low resistivity, and has a feature of easily forming a fine pattern by etching with acid or the like.

3 is a hole injection / transport layer, and is formed by contact | adhering to the anode 2 normally by the method similar to the anode 2, and forming a hole injection / transport layer material into a film with a thickness of 1-1000 nm. As the hole injection / transport layer material, in order to facilitate hole injection and transport from the anode 2, the ionization potential is small and, for example, at least 10 ⁻⁶ cm 2 at an electric load of 10 ⁴ to 10 ⁶ V / cm. It is desirable to exhibit a hole mobility of / V · s. The individual hole injection / transport layer materials are commonly used in organic EL devices, for example, arylamine derivatives, imidazole derivatives, oxadiazole derivatives, oxazole derivatives, triazole derivatives, carcon derivatives, styryl anthracene derivatives, Stilbene derivatives, tetraarylethene derivatives, triarylamine derivatives, triarylethene derivatives, triarylmethane derivatives, phthalocyanine derivatives, fluorenone derivatives, hydrazone derivatives, N-vinylcarbazole derivatives, pyrazoline derivatives , Pyrazorone derivatives, phenylanthracene derivatives, phenylenediamine derivatives, polyarylarkan derivatives, polysilane derivatives, polyphenylenevinylene derivatives, and the like, and the like, and these may be appropriately used in combination.

4 is a light emitting layer, and is usually in close contact with the hole injection / transport layer 3 by the same method as that of the anode 2, to form one or more of the coumarin derivatives according to the present invention and, if necessary, a general-purpose host compound. It is formed by separating into a single layer or a multilayer and forming a film at a thickness of 10 to 1000 nm, preferably 10 to 200 nm, respectively. When used in combination with a host compound, 0.05-50% by weight, preferably 0.1-30% by weight of the coumarin derivative according to the present invention is used relative to the host compound.

When the coumarin derivative according to the present invention is used as a guest compound, other luminescent compounds combined with the coumarin derivative according to the present invention, that is, a host compound, are quinolinol metal complexes commonly used in organic EL devices, such as anthracene, Condensed polycyclic aromatic hydrocarbons such as chrysene, coronene, triphenylene, naphthalene, phenanthrene, pysene, pyrene, fluorene, perylene, benzopyrene and derivatives thereof, quarterphenyl, 1,4-diphenylbutadiene, and other Cyclic hydrocarbons such as phenyl, stilbene, tetraphenylbutadiene, biphenyl, derivatives thereof, heterocyclic compounds such as carbazole and derivatives thereof, quinacridone, ruble, and styryl polymethine pigments; Can be mentioned.

Preferred host compounds are quinolinol metal complexes, and the quinolinol metal complexes referred to in the present invention include ligands such as 8-quinolinols and benzoquinolin-10-ols having a pyridine residue and a hydroxyl group in a molecule thereof. As a central atom, for example, lithium, beryllium, magnesium, calcium, zinc, aluminum, gallium, indium, which form a coordinating bond with a ligand by receiving an electron pair from a nitrogen atom in the pyridine residue, The complex generally consists of a metal belonging to the group 1, 2, 12, or 13 of the periodic table, or an oxide thereof. When the ligand is one of 8-quinolinols or benzoquinolin-10-ols, they may have one or more substituents, for example on carbon other than carbon at position 8 or position 10 to which the hydroxy group is bound, for example Halogen groups such as fluorine group, chloro group, bromo group and iodine group; Aliphatic groups such as methyl group, trifluoromethyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group and tert-pentyl group Hydrocarbon group; Methoxy, trifluoromethoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, phenoxy, benzyl Ether groups such as oxy group; Ester groups such as an acetoxy group, a trifluoroacetoxy group, a benzoyloxy group, a methoxycarbonyl group, a trifluoromethoxycarbonyl group, an ethoxycarbonyl group, and a propoxycarbonyl group; Moreover, one or more substituents, such as a cyano group, a nitro group, and a sulfo group, may be sufficient. When the quinolinol metal complexes have two or more ligands in the molecule, these ligands may be the same or different from each other.

As individual quinolinol metal complexes, for example, tris (8-quinolinolite) aluminum, tris (3,4-dimethyl-8-quinolinolite) aluminum, tris (4-methyl-8-quinolinolite ) Aluminum, tris (4-methoxy-8-quinolinolite) aluminum, tris (4,5-dimethyl-8-quinolinolite) aluminum, tris (4,6-dimethyl-8-quinolinolite) aluminum, Tris (5-chloro-8-quinolinolight) aluminum, tris (5-bromo-8-quinolinolite) aluminum, tris (5,7-dichloro-8-quinolinolite) aluminum, tris (5-sia No-8-quinolinolite) aluminum, tris (5-sulfonyl-8-quinolinolite) aluminum, tris (5-propyl-8-quinolinolite) aluminum, bis (2-methyl-8-quinolinolite Aluminum complexes such as aluminum oxide; Bis (8-quinolinolight) zinc, bis (2-methyl-8-quinolinolight) zinc, bis (2,4-dimethyl-8-quinolinolite) zinc, bis (2-methyl-5-chloro- 8-quinolinolite) zinc, bis (2-methyl-5-cyano-8-quinolinolite) zinc, bis (3,4-dimethyl-8-quinolinolite) zinc, bis (4,6-dimethyl Zinc complexes such as -8-quinolinolite) zinc, bis (5-chloro-8-quinolinolite) zinc and bis (5,7-dichloro-8-quinolinolite) zinc; Bis (8-quinolinolight) beryllium, bis (2-methyl-8-quinolinolight) beryllium, bis (2,4-dimethyl-8-quinolinolite) beryllium, bis (2-methyl-5-chloro- 8-quinolinolite) beryllium, bis (2-methyl-5-cyano-8-quinolinolite) beryllium, bis (3,4-dimethyl-8-quinolinolite) beryllium, bis (4,6-dimethyl -8-quinolinolite) beryllium, bis (5-chloro-8-quinolinolight) beryllium, bis (5, 7-dichloro-8-quinolinolite) beryllium, bis (10-hydroxybenzo [h] quinol Beryllium complexes such as linoleite) beryllium; Bis (8-quinolinolite) magnesium, bis (2-methyl-8-quinolinolite) magnesium, bis (2,4-dimethyl-8-quinolinolite) magnesium, bis (2-methyl-5-chloro- 8-quinolinolite) magnesium, bis (2-methyl-5-cyano-8-quinolinolite) magnesium, bis (3,4-dimethyl-8-quinolinolite) magnesium, bis (4,6-dimethyl Magnesium complexes such as -8-quinolinolite) magnesium, bis (5-chloro-8-quinolinolight) magnesium, and bis (5,7-dichloro-8-quinolinolite) magnesium, and tris (8-quinolinolite) Indium complexes such as indium; Gallium complexes such as tris (5-chloro-8-quinolinolight) gallium; Calcium complexes, such as a bis (5-chloro-8-quinolinolite) calcium, etc. are mentioned, These are used combining suitably as needed. In addition, the said host compound is a mere illustration, The host compound used by this invention is not limited to these at all.

5 is an electron injection / transport layer, and the organic compound having a high electron affinity or a cyclic ketone such as benzoquinone, anthraquinone, fluorenone, or the like is usually brought into close contact with the light emitting layer 4 by the same method as that of the anode 2. It is formed by forming one or a plurality of conductive oligomers or conductive polymers having a derivative, a sirazane derivative, aniline, thiophene, pyrrole and the like as a repeating unit with a thickness of 10 to 500 nm. When a plurality of electron injection / transport layer materials are used, the plurality of electron injection / transport layer materials may be uniformly mixed to form a single layer, or may be formed in a plurality of adjacent layers for each electron injection / transport layer material without mixing. Also good. In the case of providing the hole block layer, prior to the formation of the electron injection / transport layer 5, the light blocking layer 4 is brought into close contact with the light emitting layer 4 by the same method as in the anode 2, for example, 2-biphenyl-4-yl-5. -(4-tert-butyl-phenyl)-[1,3,4] oxadiazole, 2,2-bis [5- (4-biphenyl) -1,3,4-oxadiazol-2-yl Oxadias, such as -1,4-phenylene] hexafluoropropane, 1,3,5-tris- (2-naphthalen-1-yl- [1,3,4] oxadiazol-5-yl) benzene A thin film is formed by the hole block material including the sol compound. The thickness of the hole block layer is set in the range of 1 to 100 nm, usually 10 to 50 nm, in consideration of the thickness of the electron injection / transport layer 5 and the operating characteristics of the organic EL element.

6 is a cathode, and is usually in close contact with the electron injection / transport layer 5 and has a lower work function (usually 5 eV or less) than the compound used in the electron injection / transport layer 5, for example lithium, magnesium, calcium Metal, metal oxides or conductive compounds such as sodium, silver, copper, aluminum, indium, or conductive compounds are formed by vapor deposition alone or in combination. There is no restriction | limiting in particular about the thickness of the cathode 6, In consideration of electroconductivity, manufacturing cost, the thickness of the whole element, light transmittance, etc., it is 10 nm or more in thickness, Preferably it is 50-500 nm so that resistivity may be 1 ㏀ / square or less. Is set. Moreover, in order to improve adhesiveness between the negative electrode 6 and the electron injection / transport layer 5 containing an organic compound, if necessary, for example, an aromatic diamine compound, a quinacridone compound, a naphthacene compound, an organosilicon You may form the interface layer which consists of a compound or an organophosphorus compound. In addition, in order to facilitate movement from the electron cathode 6 to the electron injection / transport layer 5, the electron injection / transport layer 5 adjacent to the electron injection / transport layer 5 on the cathode 6 is similar to the anode 2. On the side, a thin film having a thickness of, for example, an alkali metal compound such as lithium fluoride or lithium oxide or an alkaline earth metal compound may be formed.

As described above, the organic EL device of the present invention has an anode 2, a light emitting layer 4, a cathode 6, a hole injection / transport layer 3, and an electron injection / transport layer 5 on the substrate 1 as necessary. And / or forming the hole block layer integrally with the adjacent layers while being in close contact with each other. In forming each layer, in order to minimize the oxidation and decomposition of an organic compound, the adsorption | suction of oxygen, a moisture, etc. to the minimum, it is preferable to carry out the ring-work in high vacuum, in detail below ^10-5 Torr. In order to form the light emitting layer, a compounding ratio of both in the light emitting layer is controlled by mixing a host compound and a guest compound at a predetermined ratio in advance or by controlling the heating rates of both in vacuum deposition independently. Adjust The organic EL device thus constructed is partially or entirely encapsulated with, for example, an encapsulating glass or metal cap in an inert gas atmosphere, or a protective layer made of an ultraviolet curable resin so as to minimize deterioration in the use environment. It is preferable to cover with.

When the organic EL device of the present invention is described, the organic EL device of the present invention intermittently applies a relatively high voltage pulse voltage, or a non-pulse voltage of relatively low voltage (usually 3 to 3) depending on the application. 50V) is applied continuously to drive. 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 element of the present invention may be either direct current or alternating current, and the waveform and period of the applied voltage may also be appropriate. When alternating current is applied, the organic EL element of the present invention, in principle, increases or decreases the brightness or blinks in accordance with the waveform and period of alternating current applied. In the case of the organic EL device shown in FIG. 1, when a voltage is applied between the anode 2 and the cathode 6, holes injected from the anode 2 pass through the hole injection / transport layer 5 and the light emitting layer 4. ) And through the electron injection / transport layer 5 injected from the cathode 6 to reach the light emitting layer 4, respectively. As a result, in the light emitting layer 4, recombination of holes and electrons occurs, and the desired light emission is emitted through the anode 2 and the substrate 1 from the coumarin derivative in the excited state generated thereby. The organic EL device of the present invention also depends on the structure and compounding ratio of the host compound used in the coumarin derivative and the combination, but usually has a light emitting maximum such as a fluorescent maximum in the green to red region, particularly around 500 to 650 nm. The light emission is usually in the range of 0.33 to 0.63 and y in the range of 0.36 to 0.63 on the xy chromaticity diagram.

The organic EL device of the present invention has excellent durability, high luminous efficiency, and high luminance as a result, and therefore has various uses in information display apparatuses for visually displaying a light emitting body and information. Since the light emitting body using the organic EL element as a light source of the present invention has a low power consumption and can be configured in a lightweight panel shape, in addition to a general light source, for example, a liquid crystal device, a copying device, a printing device, an electrophotography Apparatus, computer and its application equipment, industrial control equipment, electronic measuring instruments, analyzers, general measuring instruments, communication equipment, medical electronic measuring instruments, vehicles including automobiles, ships, aircraft, spacecraft, etc. It saves energy in interiors, signs, signs, etc., and is useful as a space saving light source. The organic EL device of the present invention is, for example, a computer, a television, a video, a game. When used in information display devices such as clocks, telephones, car navigation systems, oscilloscopes, radars, sonars, etc., either alone or in combination with organic EL elements emitting light in the blue, green and / or red regions. If necessary, it operates by applying general simple matrix method or active matrix method.

In addition, as described above, the coumarin derivative of the present invention has an absorption maximum in the visible region and substantially absorbs the visible light, so that the polymerizable compound is exposed to visible light for polymerization, and the material for increasing or decreasing the solar cell. It has a variety of uses as a chromaticity adjusting material in optical filters and as a material for dyeing various clothes. In particular, most of the coumarin derivatives of the present invention have absorption maximum wavelengths, for example, gas lasers such as argon ion lasers and krypton ion lasers, semiconductor lasers such as CdS-based lasers, distributed feedback or distributed brack reflection type Cd-YAG. Since it is close to the oscillation line (wavelength 400-550 nm) in general-purpose lasers including solid lasers, such as a laser, it mixes this laser as a photosensitizer to the photopolymerizable composition which makes an exposure light source a facsimile and a copier. Can be used very advantageously in the field of information recording such as a freezer, printing field such as flexure plate and gravure plate, and printed circuit field such as photoresist.

In the case of using the coumarin derivative of the present invention as a laser action material, it is purified in the same manner as in the case of constituting a known dye laser oscillator, dissolved in an appropriate solvent, and the pH of the solution is adjusted to an appropriate level as necessary. It encloses in the dye cell in a laser oscillation apparatus. The coumarin derivatives of the present invention have not only amplified gain in a very wide wavelength range in the visible region, but also have high light resistance and are difficult to deteriorate even after long-term use compared with known flexible compounds.

In addition, the coumarin derivative of the present invention, together with one or more of other materials absorbing light in the ultraviolet region and / or the visible region, as necessary, in addition to general clothing, clothing, for example, drape, lace, Casement, Print, Venetian blind, Roll screen, Shutter, Shop curtain, Blanket, Futon, Futon, Futon cover, Futon cotton, Sheet, Cushion, Pillow, Pillow cover, Cushion, Mat, Rug, Sleeping bag, Building bedroom decorative articles such as tents, interior materials of vehicles including automobiles, window glass and window glass; Health supplies such as paper diapers, diaper covers, eyeglasses, monocles, eyeglasses with handles; Shoe insoles, shoelaces, bag leather, furnishings, umbrellas, parasols, stuffed toys, lighting devices, and information displays such as television sets or personal computers using, for example, CRT displays, electroluminescent displays, plasma displays, etc. Optical filters for devices; Panels and screens, sunglasses, sunroofs, PET bottles, storage rooms, plastic houses, cold-cooled yarns, fiber optics, prepaid cards, microwave ovens, viewing windows such as ovens, packaging materials for packaging, filling or storing these items, When used in a filling material, a container, or the like, it is possible not only to prevent or reduce obstacles or obstacles caused by environmental light such as natural light or artificial light in a living organism or article, but also to adjust the color, color, touch, etc. of the article, The advantage is that the reflected or transmitted light can be adjusted to the desired color balance.

EMBODIMENT OF THE INVENTION Hereinafter, embodiment of this invention is described according to an Example.

(Example)

Example 1: Coumarin Derivative

10 ml of N, N-dimethylformamide was added to the reaction vessel, and 3.3 g of the compound represented by the formula (28) and 1.8 g of the compound represented by the formula (29) were added, followed by heating to reflux for 4 hours. The reaction mixture was cooled to ambient temperature, the precipitated crystals were filtered off, purified by silica gel column chromatography using chloroform as a developing solvent, and then recrystallized with a chloroform / methanol mixture to obtain the coumarin derivative represented by the formula (2). 1.1 g of orange crystals were obtained.

Part of the crystals were taken, and the visible absorption spectrum and the fluorescence spectrum in the methylene chloride solution were measured according to a conventional method. As a result, absorption maximum and fluorescence maximum were observed at wavelengths of 450 nm and 515 nm, respectively. In addition, a 1.35 ¹ H- nuclear magnetic resonance spectrum (hereinafter abbreviated as ^"1 H-NMR spectrum.") Further, a chemical shift (δ, TMS) was measured in a chloroform solution by a conventional method -d (6H, s), 1.61 (6H, s), 1.79 (2H, t), 1.84 (2H, t), 2.95 (3H, s), 3.27 (2H, t), 3.35 (2H, t), 7.50 ( Positions of 1H, s), 7,53 (1H, t), 7.60 (1H, t), 7.85 (1H, d), 7.96 (1H, d), 8.09 (1H, d) and 8.14 (1H, d) Peaks were observed.

The glass transition point of the coumarin derivative of the present example was 109 ° C as a result of DSC analysis at a temperature rising rate of 10 ° C / min using a commercially available DSC analyzer (product name "DSC220U" manufactured by Seiko Instruments Co., Ltd.). Separately, the DSC of the flexible compound represented by the general formula (30) at which position 4 of the coumarin skeleton in the general formula (2) prepared by the general-purpose method was a hydrogen atom was similarly analyzed by DSC. As a result, the glass transition point was 133 占 폚.

The coumarin derivatives of this embodiment having absorption and fluorescent maximums in the violet and green regions, respectively, are used in various fields including photochemical polymerization, solar cells, dyeing, optical filters, organic EL devices, and dye lasers as light absorbers and light emitting agents. It is useful.

Example 2 Coumarin Derivative

10 ml of N, N-dimethylformamide was added to the reaction vessel, and 3.0 g of the compound represented by the formula (31) and 1.4 g of the compound represented by the formula (29) were added, followed by heating to reflux for 4 hours. The reaction mixture was cooled to ambient temperature, the precipitated crystals were filtered off, purified by silica gel column chromatography using chloroform as a developing solvent, and then recrystallized with a chloroform / methanol mixture to obtain the coumarin derivative represented by the formula (8). 0.8g of red crystals were obtained.

Part of the crystals were taken, and the visible absorption spectrum and the fluorescence spectrum in the methylene chloride solution were measured according to a conventional method. As a result, absorption maximum and fluorescent maximum were observed at wavelengths of 462 nm and 653 nm, respectively. In addition, as a result of measuring the ¹ H-NMR spectrum in the chloroform-d solution according to a conventional method, the chemical shifts (δ, TMS) were 1.32 (6H, s), 1.56 (6H, s), 1.78 (2H, t), 1.84 (2H, t), 3.30 (2H, t), 3.38 (2H, t), 7.49 (1H, s), 7.52 to 7.64 (2H, m), 7.88 (1H, d), 7.97 (1H) , d), peaks were observed at positions 8.04 (1H, d) and 8.11 (1H, d). Moreover, as a result of DSC analysis as in Example 1, the glass transition point of the coumarin derivative of the present Example was 100 degreeC.

The coumarin derivatives of this embodiment having absorption and fluorescent maximums in the violet and red regions, respectively, are light absorbers and light emitting agents in all fields including photochemical polymerization, solar cells, dyeing, optical filters, organic EL devices, and dye lasers. useful.

Example 3: Coumarin Derivative

5 ml of N, N-dimethylformamide was added to the reaction vessel, and 2.0 g of the compound represented by the formula (32) and 1.3 g of the compound represented by the formula (29) were added, followed by heating to reflux for 4 hours. The reaction mixture was cooled to ambient temperature, the precipitated crystals were filtered off, purified by silica gel column chromatography using chloroform as a developing solvent, and then recrystallized with a chloroform / methanol mixture to obtain the coumarin derivative represented by the formula (15). 1.0 g of orange crystals were obtained.

Part of the crystals were taken and the visible absorption spectrum and the fluorescence spectrum in the methylene chloride solution were measured according to a conventional method. As a result, absorption maximum and fluorescence maximum were observed at wavelengths of 450 nm and 509 nm, respectively. Moreover, as a result of measuring ¹ H-NMR spectra in a chloroform-d solution according to a conventional method, the chemical shifts (δ, TMS) were 1.36 (6H, s), 1.45 (3H, t), and 1.61 (6H, s). ), 1.78-1.86 (4H, m), 3.27 (2H, t), 3.35 (2H, t), 3.44 (2H, q), 7.52 (1H, s), 7,56 (1H, t), 7.60 ( Peaks were observed at the positions of 1H, t), 7.85 (1H, d), 7.96 (1H, d), 8.08 (1H, d) and 8.14 (1H, d).

The coumarin derivatives of the present embodiment having absorption and fluorescent peaks in the violet region and the green region, respectively, are light absorbers and light emitting agents in all fields including photochemical polymerization, solar cells, dyeing, optical filters, organic EL devices, and dye lasers. useful.

Example 4: Coumarin Derivative

Sublimation purification was carried out by putting three kinds of coumarin derivatives obtained by the methods of Examples 1 to 3 separately into a water-cooled sublimation purification apparatus and heating the same while maintaining the apparatus at a reduced pressure according to a conventional method.

The coumarin derivative of the present embodiment with high purity is very useful in the field of organic electronics including organic EL devices and dye lasers.

In addition, the coumarin derivative according to the present invention has a slight difference in supply conditions and yields depending on the structure, but for example, the method of Examples 1 to 4, including those represented by the above Chemical Formulas 1 to 27, The desired amount can be prepared by following or by their methods.

Example 5 Organic EL Device

Using the coumarin derivative according to the present invention, a laminated organic EL device having a structure shown in Fig. 1 was produced.

A glass substrate 1 having a transparent ITO electrode having a thickness of 150 nm as an anode 2 patterned by aqua regia vapor was ultrasonically washed with detergent, pure water, acetone and ethanol, dried and treated with ultraviolet ozone. It was then fixed in a vacuum deposition apparatus, and the pressure was reduced to 8 x 10 ^-7 Torr. Subsequently, a tetramer of triphenylamine represented by the formula (33) was deposited on the surface having the ITO electrode in the glass substrate 1 to a thickness of 60 nm to form the hole injection / transport layer 2. Thereafter, the coumarin derivative and tris (8-quinolinolite) aluminum of the present invention represented by the formula (2) were co-deposited to a thickness of 20 nm with a weight ratio of 1: 100 as a guest light emitting agent and a host light emitting agent, respectively, by monitoring with a film thickness sensor. The light emitting layer 4 was formed, and tris (8-quinolinolite) aluminum was further deposited to a thickness of 40 nm to form the electron injection / transport layer 5, followed by lithium fluoride and aluminum in the order of 0.5 nm in thickness, respectively. And 160 nm to form a cathode 6. Thereafter, under the nitrogen atmosphere, the entire device was sealed using a glass plate and an ultraviolet curable resin to obtain a green light emitting organic EL device.

The organic EL device thus obtained was measured in accordance with a conventional method, and the change in luminance over time when the constant current was driven at an initial emission luminance of 2,400 cd / m 2 at an ambient temperature of 85 ° C was investigated. , Life expectancy was estimated. Separately, in place of the coumarin derivative represented by the formula (2), a system using the flexible compound represented by the formula (30) was formed, and the treatment was performed in the same manner as above to prepare a control.

According to the emission spectrum, the organic EL device of the present example had a luminescence maximum in the green region having a wavelength of 528 nm, and the color coordinates of the light emission in the xy chromaticity diagram were 0.34 and y1 0.61. Light emission was stably maintained even at constant temperature driving at an initial luminance of 2,400 cd / m 2 at an environmental temperature of 85 ° C., and the lifetime (driving time at which the initial luminance was halved) was estimated to be about 65 hours under these conditions. On the other hand, the organic EL device of contrast had relatively good color purity, but the life time when the constant current was driven under the same conditions as above was about 25 hours, which was very short compared with the organic EL device according to the present invention. The compound represented by the formula (30) is particularly durable among the flexible compounds, and is a substance exhibiting durability close to N, N'-dimethylquinacridone, which is already practically used as a light emitting layer material in organic EL devices. Further, according to the conventional method, the current efficiency and the external quantum efficiency at 300 cd / m 2, which are practical luminance, were measured, respectively. As a result, the current efficiency and the external quantum efficiency of the organic EL device of this embodiment were 11.6 cd / A and 3.2, respectively. The current efficiency and the external quantum efficiency of the organic EL device produced in the same manner as above using N, N'-dimethylquinacridone instead of the coumarin derivative according to the present invention were 6.9 cd / A, respectively. And 1.8%, which was very inferior to that of the organic EL device of this embodiment. The fact is that the organic EL device according to the present invention is useful as a green light emitting device, and by using the coumarin derivative of the present invention, it is possible to realize an organic EL device having a long life, high brightness and high efficiency that can withstand harsh use environments. I'm telling you.

Example 6 Organic EL Device

An organic EL device for red light emission was manufactured in the same manner as in Example 5 except that the coumarin derivative represented by the formula (8) was used instead of the coumarin derivative represented by the formula (2).

The organic EL device of this example had a maximal emission peak in the red region with a wavelength of 614 nm, and the color coordinates of the emission in the xy chromaticity diagram were x2 at 0.52 and y at 0.45. Further, according to the conventional method, the current efficiency and the external quantum efficiency at 300 cd / m2, which are practical luminance, were measured, respectively. As a result, the current efficiency and the external quantum efficiency of the organic EL device of this embodiment were 3.4 cd / A and 1.7, respectively. In contrast to the%, 4- (dicyanomethylene) -2-tert-butyl-6- (1,1,7,7-tetramethyluroridyl has already been put into practical use as a light emitting layer material in place of the coumarin derivative according to the present invention. The current efficiency and the external quantum efficiency of the organic EL device fabricated in the same manner as above using -9-enyl) -4H-pyran are 1.7 cd / A and 1.3%, respectively, which are very high compared to the organic EL device of this embodiment. I was behind. This fact indicates that the organic EL device according to the present invention is very useful as a high luminance, high efficiency red light emitting device.

Example 7 Display Panel

2 schematically shows an example of a simple matrix display panel mainly composed of the organic EL device of the present invention (20 electrode rows in the horizontal direction and 30 electrode rows in the vertical direction). It can be produced in the same way.

That is, according to the method of any one of Example 5 or Example 6, the anode 14 by ITO transparent electrode is formed on one side of the glass substrate 10, and then the anode 14 is striped by wet etching. Process into a phase. Subsequently, in accordance with the method of Example 5, the hole injection / transport layer 16 and the light emitting layer 18 were sequentially formed, and the cathode 20 was formed in a stripe shape using a mechanical mask, followed by a glass plate (not shown). The organic EL element is sealed by ultraviolet curing resin. In the display panel of the present embodiment, a heat sink or a cooling fan may be attached to the back side of the cathode 20 as necessary to suppress the temperature rise during use.

Example 9 Information Display Device

3 shows one example of an information display apparatus using the display panel produced by the method of the seventh embodiment. In Fig. 3, 30 is a DC power supply having an output voltage of 4.5 V, and two boost circuits 32 and 34 are connected to the output terminal thereof. The booster circuit 32 can supply a DC power supply in the range of 5 to 12V, and its output terminal is connected to the driver circuit 36. Another boost circuit 34 is for supplying a constant voltage of 5V to the microcomputer 38.

The microcomputer 38 includes an I / O interface 38a for exchanging signals with the outside, a ROM 38b for recording programs, a RAM 38c for recording various data, and a CPU for executing various operations. And 38d. The microcomputer 38 is connected to a clock generating circuit 40 for supplying a clock signal of 8 MHz to the microcomputer 38, and two oscillating circuits 42 and 44, respectively. 44 is for supplying the microcomputer 38 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.

48 is a display panel mainly composed of the organic EL element of the present invention, and is connected to the microcomputer 38 via the driver circuits 36 and 48. The driver circuit 36 is a circuit for controlling the application of the direct current voltage from the booster circuit 32 to the display panel and includes a plurality of transistors individually connected to the vertical electrode lines in the display panel 48. . Therefore, when any one of the transistors in the driver circuit 36 is turned ON, the voltage from the boosting circuit 32 is applied to the vertical electrode array connected to the transistor. On the other hand, the driver circuit 46 includes a plurality of transistors which are individually connected to the horizontal electrode lines of the display panel 48. Therefore, when any one of the transistors in this driver circuit 36 is turned ON, the voltage from the booster circuit 32 is applied to the vertical electrode array connected to this transistor. On the other hand, the driver circuit 46 includes a plurality of transistors that are individually connected to the horizontal electrode lines of the display panel 48, and turns on any one of the transistors in the driver circuit 46. Then, the horizontal electrode array connected to this transistor is grounded.

Since the information display device of this embodiment is configured in this manner, when the transistors in the driver circuits 36 and 46 are turned on in accordance with the instruction of the microcomputer 38, the display panel 48 has a vertical direction and A predetermined voltage is applied between the corresponding electrode rows in the horizontal direction so that the organic EL elements located at their intersections emit light. Therefore, for example, one column is selected in the horizontal direction by appropriately controlling the driver circuit 46 and connected to the vertical electrode array by appropriately controlling the driver circuit 36 while grounding the electrode array. When the transistors are turned on one by one, the entire electrode array in the selected horizontal direction is scanned in the horizontal direction to display a given pixel. By repeating these scans in the vertical direction one by one, the entire screen can be displayed. In addition, since the driver circuit 36 in this embodiment has a data register for one row of electrodes, it is preferable to drive the transistor based on the data recorded therein.

The information to be displayed may be supplied from the outside in accordance with the speed and period of the display, or the pattern may be stored in the ROM 38b in advance for information having a certain pattern, such as, for example, character information. good. In addition, in the case of displaying a television broadcast by a normal NTSC system, the received signal is first divided into a horizontal synchronous signal and a vertical synchronous signal according to a horizontal frequency and a vertical frequency based on the broadcast standard, and a video signal is displayed. A digital signal corresponding to the number of pixels of the panel 48 is converted. By appropriately synchronizing these signals to the microcomputer 38, television broadcasting can be displayed on the display panel 48.

As described above, the coumarin derivative of the present invention has an absorption maximum in the visible region, substantially absorbs visible light, and has a maximal emission region in the visible region, and thus emits visible light. As a light emitting agent, it is useful in all fields including, for example, photochemical polymerization, solar cells, dyeing, optical filters, organic EL elements, and dye lasers, which require organic compounds having such properties.

In particular, the coumarin derivative of the present invention having a maximal emission region in the visible region and having a glass transition point in the range of 100 to 110 ° C. emits visible light in a relatively long wavelength region, particularly in a green region to a red region, in an organic EL device. Moreover, light emission lasts for a long time stably. The organic EL device according to the present invention has a high luminous efficiency, and as a result, has a high luminance, and thus is a light source in general lighting, for example, an image as a light source that emits visible light by forming in a suitable shape such as a panel shape. It can be used very advantageously in various information display apparatuses which visually display information such as information and text information.

The coumarin derivative is composed of an aldehyde group and a hydrocarbon group bonded to positions 3 and 4 in the coumarin skeleton, respectively, and also adjacent to a coumarin compound having a urolidine skeleton at sites other than positions 3 and 4, The desired amount can be obtained by the production method of the present invention via a process of reacting a hydrocarbon in which a thiol group and a primary amino group are bonded to a carbon atom.

The present invention exhibiting such a remarkable effect can be said to be a very meaningful invention that can greatly contribute to the industry.

Claims (20)

A coumarin derivative having a hydrocarbon group bonded to position 4 in the coumarin skeleton and having a urolidine skeleton and a benzothiazole skeleton at a position other than position 4. The coumarin derivative according to claim 1, having an absorption maximum in the visible region. The coumarin derivative according to claim 1 or 2, which has a luminescence maximum in the visible region. The coumarin derivative according to any one of claims 1 to 3, wherein the glass transition point is in the range of 100 to 110 ° C. The coumarin derivative according to any one of claims 1 to 4, represented by the general formula (1). (Formula 1) (In Formula 1, R ₁ represents a hydrocarbon group, and the hydrocarbon group may have a substituent. R ₂ to R ₅ each represent a hydrogen atom or an aliphatic hydrocarbon group. Z represents an aromatic ring condensed with a thiazole ring.) A coumarin derivative having a maximal emission region in the visible region and having a glass transition point of 100 to 110 ° C. The light absorbing agent containing the coumarin derivative as described in any one of Claims 1-6. 8. The light absorbing agent according to claim 7, as a photosensitizer. The light-emitting agent containing the coumarin derivative in any one of Claims 1-6. The light emitting agent according to claim 9, which is used as a light emitting layer material in an organic light emitting device. 10. The light emitting agent according to claim 9, as a laser acting material. An organic electroluminescent device using the coumarin derivative according to any one of claims 1 to 6. The method according to claim 12, wherein a hole injection / transport layer, an electron injection / transport layer, and / or a hole block layer are formed together with the anode, the light emitting layer, and the cathode as needed, and the light emitting layer is the light emitting layer. An organic electroluminescent device comprising the coumarin derivative according to any one of claims. The organic electroluminescent device according to claim 12 or 13, wherein a coumarin derivative is used in combination with another luminescent compound. The organic electroluminescent device according to any one of claims 12 to 14, comprising a quinolinol metal complex, together with the coumarin derivative according to any one of claims 1 to 6. The organic light emitting device of any one of claims 12 to 15, wherein the organic light emitting diode emits visible light in a green region to a red region. A display panel using the organic electroluminescent element according to any one of claims 12 to 16. An information display apparatus using the organic electroluminescent element according to any one of claims 12 to 16. A coumarin compound having an aldehyde group and a hydrocarbon group at positions 3 and 4 in the coumarin skeleton, respectively, having a urolidine skeleton at positions other than positions 3 and 4, and a thiol group and a primary amino group as adjacent carbon atoms The method for producing a coumarin derivative according to any one of claims 1 to 6 via a step of reacting an aromatic hydrocarbon group formed by admixing. The process according to claim 19, wherein the compound represented by the general formula (2) having R ₁ to R ₅ corresponding to the general formula (1) and the compound represented by the general formula (3) having the Z corresponding to the general formula (1) are reacted. Method for producing a coumarin derivative. (Formula 2) (Formula 3)