TW200840819A - Bis (3-arylamino) diphenyl metal compound and an origanic electroluminescence element containing such metal compound - Google Patents

Abstract

This invention provides a blue phosphoric light emitting element with enhanced brightness of the emitted light and efficiency f emission, and the material therefore. The blue phosphoric light emitting element uses a his (3-arylamino) diphenyl metal compound represented by the general formula (1): wherein M represents a silicon atom or a germanium atom, and Ar2 may be the same or different, and represent an aryl group or a complex aryl group, of which any hydrogen atom, an alkyl group, a cycloalkyl group, a alkenyl group, an aryl group, an ardkyl group, and adjoining Ar1 and Ar2 may be directly bonded, or ether bonded, thioether bonded, or bonded through an alkylene group, an oxaalkylene group, or a thiaalkylene group.

Description

200840819 u IX. Description of the invention: "Technical field to which the invention pertains" The present invention relates to an electroluminescent device (5), which is priced as a service (1). The organic electroluminescent device can be utilized, for example, for hanging television or • impressing A flat light-emitting body such as a flat-panel display of a telephone, a light source such as a photocopier, a printer, a backlight of a liquid crystal display, or a meter, a display panel, a signal light, etc. [Prior Art] In recent years, low-voltage and high-brightness light can be emitted. The organic electroluminescence element is being researched and developed as a display element of the next generation (for example, refer to Non-Patent Documents 1 and 2). However, the blue phosphorescent element required for a full-color display is luminous. Insufficient, and it is required to improve the brightness and efficiency of light emission. [Non-Patent Document 1] "2006 Advanced Material R& DRep〇rt", Fuji

Chimera Research Institute, 2006, Nana [Non-Patent Document 2], Mr. Jing Shi, "Organic EL Display", • Company, 2004 [Inventions] (Problems to be Solved by the Invention) The subject of the present invention is to solve the above problems. A blue phosphorescent light-emitting element having improved illuminance and efficiency, and a material of the light-emitting element 0 (Means for solving the problem) The subject of the present invention is a bis(3-aryl group) represented by the general formula (1) Amino) a base metal compound to solve... 319891 6 200840819

(wherein, the lanthanide indicates that the Si atom or G may be different, the table (4) group or the base group, and the aryl A, Ar#, may be the same or the following: a prime atom, a hospital base, a Weiji, a county: = (a) atom and also

Oxygen, or aryloxy substituted 'other additions adjacent Ar, = also; =, dazzle

It, sulfur - complete, = In addition, the subject of the present invention is to form a light-emitting member by a pair of layers or containing a hair 厣 夕 夕 士 士 士 # # 3 The right illuminating element of the metallized person is included in the luminescent layer to solve the problem. Organic of Sputum (Invention Effect) According to the present invention, it is possible to provide blue luminosity with improved illuminance and efficiency _ per optical element and material of the illuminating element. [Embodiment] The bis(3-arylamino)diphenyl metal compound of the present invention is represented by the above formula (1). In the above formula (1), Ar! A may, for example, be an aryl group having 6 to 14 carbon atoms such as a phenyl group, a naphthyl group, a phenanthryl group or a fluorenyl group, a fluorenyl group or a fluorenyl group ( Thiophenyl),. Ratio of 17 groups, imidaz, oxazolyl, π 唆 、, thiaz〇iyi, indolyl, quinolinyl 'isoquinolyl, quin a heteroaryl group having 4 to 10 carbon atoms such as quinazolyl or quinoxalyl. In addition, μ 7 319891 200840819

The J system represents a germanium atom or a germanium atom. Any hydrogen atom on the early square or fluorene aryl group may also be a halogen atom, a cycloalkyl group, an alkenyl group, an aryl group, an aryl group, an alkoxy group, or an aryl group: The neighboring Ar can be directly or in combination with each other (Αι·1 and Ar2), and can be separated by a _ bond, a thioether bond, or a stretch bond. The alkyloxyalkyl group or the sulfur alkyl group is described. The halogen atom system may, for example, be a fluorine atom, a chlorine atom, a bromine atom or an insoluble atom. • Α is: = = carbon number 1 to 2 〇, especially in the case of carbon number 1 to 12 炫 2 = for example: methyl, ethyl, propyl, butyl, pentyl, hexaheptyl , octyl, sulfhydryl, sulfhydryl, eleven, and twelve bases. Further, such substituents also include isomers thereof. The cycloalkyl group is preferably a cycloalkyl group having 5 to 8 carbon atoms, and examples thereof include a pentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. The United States is a terpene, which is 2 to 2G, especially a olefin of the carbon number 2 to U, m, ethene, butyl, pentenyl, alkenyl, heptyl, octenyl, decene. Base, 癸 dilute, ten beautiful, and ten: thin (four). Further, these substituents also include the isomer/methine group, preferably an aryl group having 6 to 12 carbon atoms, and examples thereof include benzene: fluorene: hydrazine, hydrazine, and xylene. Base (and its different _, 兴, things), and dimethyl naphthyl (and its isomers). The aromatic base system is preferably an aromatic alkyl group having a carbon number of 7 to 2 G, and may be, for example, (d), naphthylmethyl, indenyi methyl, and biphenylmethylpyrene; The oxime number of 1 i 10 is preferably, for example, 319891 8 200840819 pentyloxy, hexyloxy, . Further, such substituents as methoxy, ethoxy, propoxy, butoxy, heptyloxy, octyloxy, decyloxy, and decyloxy groups also include isomers thereof. % The above aryloxy group is a aryl group having a carbon number of 6 or 4, such as a st. oxy group, a benzyloxy group, a dimethyloxy group, a hexyloxy group, and a decyloxy group. Further, such substituents also include isomers thereof. —Base group The above-mentioned stretching base is preferably a stretching group of Wei 1 to 6, and examples thereof include a methylene group, a propyl group, a butyl group, a pentyl group, and a hexamethylene group.

The oxygen (tetra)-based fine carbon number of 1 to 5 oxygen (tetra) group is preferred, for example, oxymethylene I, oxypropyl propyl, oxobutyl, oxopentyl, oxetyl, monomethylene, Dioxypropylidene, dioxetylene, dioxopentyl, 2-oxohexyl. Further, such substituents also include isomers thereof. Month's sulphur extension base is based on carbon number! The sulfur-extinguishing group to 5 is preferable, and examples thereof include a sulfur methylene group, a sulfur-extension propyl group, a sulfur-extension butyl group, a sulfur-extension pentyl group, a sulfur-extension hexyl group, a monothiomethylene group, and a dithio-propyl group. Disulfide butyl, dithiopentyl, and disulfide hexyl. Further, such substituents also include isomers thereof. - the above alkyl, cycloalkyl, alkenyl, aryl, aralkyl, alkoxy, and aryloxy groups, and an alkyl group, an oxygen group, and an extension of an adjacent Ari& Ar2: The k group is a hydrogen atom bonded to a carbon atom thereof, and may further be a halogen atom, an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, a nitro group, a cyano group or a dialkylamino group. Replace. These substituents may be the same as those defined above for Ar and Ar2. The compound used in the present invention is as shown in the following reaction step (1), and can be produced by reacting an aniline compound with a di-diphenyldiphenyl metal compound 319891 9 200840819 [Reaction step (1) j Ar2

Ph2MC!2 P\ , Ph Ar^ft逦 1 (wherein X represents Li or MgY (Y-based atom) 'Ar, Ar and secret lines are the same as the above). ', 法f: Γ "Real: Chlorine bismuth-based metal compounds, for example, according to the well-known genus of the second year of science, the fourth edition of the scientific lecture, 25 volumes, organic money", Pill's organic electroluminescent components An organic electroluminescent device which is a composite layer between a pair of electrodes, and is characterized in that: 4 each layer has a compound represented by the above formula (1). Further, here, there are: = a layer-based light-emitting layer, an electron injecting layer, or a hole transporting layer, and a compound which is not contained in the above (1) may be added to the light-emitting layer or may be contained in the electron injecting layer or the hole transporting layer. The single-layer type organic electroluminescent device has a light-emitting layer between the anode and the cathode. The light-emitting layer contains a light-emitting material, and may further contain a hole injecting material or an electron injecting material for transporting electrons from the anode or the terminal of the anode to the light-emitting material. The concentration of the compound shown in the formula (1) to the luminescent layer is 5 to 98% by weight. 319891 10 200840819 The organic electroluminescent device can also use a combination luminescent material, other materials, and doping materials. The hole injecting material or the electron injecting material, and the hole injecting layer, the light emitting layer, and the electron injecting layer may be formed by two or more layers. In this case, the hole is injected into the layer and injected from the electrode. The layer of the hole ▲ is called the hole injection layer, and the layer that receives the hole from the hole injection layer and transports the hole to the light-emitting layer is called a hole transport layer. Similarly, the case of the electron injection layer is the electrode. The layer in which electrons are injected is called an electron injecting layer, and the layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer is called an electron transport layer. These layers are based on the energy level, heat resistance, and organic compound layer of the material. or It is used in various factors such as the adhesion to the metal electrode. The material used in the light-emitting layer together with the compound represented by the above formula (1) is required to add various kinds of ruthenium, ruthenium, gold, A photo-alignment dye of a central metal such as ruthenium or osmium. In addition, a luminescent material or a host material which can be added to the luminescent layer is, for example, various carbazole derivatives and condensed polycyclic aromatic compounds. Family (蒽, • naphthalene, phenanthrene, pyrene, tetracene, pentacene, hexabenzone; coronene, chrysene, fluorescein, quinone (perylene), rubrene and its derivatives, phthaloperylene, naphthoquinone, peripurone (peri/2〇/3e), hydrazine and perhexanone, naphthacene ketone (napiitiiaJoperi/io/ie), diphenylbutadiene, tetraphenylbutadiene, coumarin, quinone, aldazine, pyrazine, cyclopentane Diene, ruthenium metal complex, amine ruthenium metal 11 319891 200840819 complex, benzoquinoline metal , quinolinyl acetylene metal complex, quinoxaiyi acetylene metal complex, quinazolyl acetylene metal complex, imine, diphenylethylene ", ethylene two • En, diaminocarbazole, pyran, thiopyran, polymethylene (P〇lymethlne), merocyanine (imocyanine), imidazole clamped oxides, antimony Ketones (qUjnacrid〇ne), red fluorescein, stilbene gas derivatives and fluorescent pigments. A well-known hole injecting material which can be used in the organic electroluminescent device of the present invention is a more effective hole injecting material which is an aromatic tertiary amine derivative or an indigo derivative. The specific state of the aromatic tertiary amine derivative is diphenylamine, tris(tolyl)amine, fluorenylphenyldiphenylamine, N,N,-diphenyl rhenium phenyl phenyl bromide 7: two Under the amine (3) "self contained: TPD", N, N, N, N, a (4-phenylene), Γ _ phenyl- 4, 4, monodiamine, hydrazine, hydrazine, hydrazine, Ν '-(4-tolyl)_;[,! , _biphenyl_4, 4, _diamine, & ν, diphenyl-anthracene, Ν'-dinaphthyl-anthracene, a biphenyl _4,4, _ diamine, hydrazine, hydrazine, _ (toluene, yl)-11^-(4-n-butylphenyl)-phenanthrene-9,1〇_diamine, bis-xyl dimethyl-f-amino)phenyl]cyclohexan, etc., or have this The aromatic polymer or polymer of the aromatic tertiary amine skeleton is not limited thereto. Specific examples of phthalocyanine (Pc) derivatives are H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, Mnpc, C1 Mpc, inpc, CISnPc, ChSiPc, (10)) A1Pc, (10) Gapc, ,

The phthalocyanine derivative such as MoOPc or GaPc-〇-GaPc and the naphthylphthalocyanine derivative are not limited thereto. Among the various organic electroluminescent devices of the present invention, the well-known 319891 12 200840819 - the electron injecting material is a metal complex or a nitrogen-containing five-member ring street creature. The specific form of the metal complex is 8-hydroxyquinoline lithium [(8-hydr〇xyquinoiinato) Lithi (4)], double (8_base-based scare), double (8-transbasic (tetra)) copper, double ( 8 A glimpse of the bell, the ginseng (8_ by Ji Jilin). Aluminum (hereinafter, described as A1q3), ginseng ) gallium, double (1G-filament benzoate) material, bismuth, bis(1)-p-benzoquinone [h]啥咐) zinc, bis(2_methyl_8_啥琳) chlorogallium, bis (2-A) Base (2-methyl-8-噎琳) (2_naphthalene) gallium, etc., but is not limited thereto. In addition, the nitrogen-containing five-membered ring derivative is carbazole, thiazole, oxadiazole, and shy A azole or a derivative of a diazole is preferred. Specifically, for example, 2, bis(1-phenyl)-1,3,4-carbazole, dimethyl P〇p〇p (here, P〇p〇p represents 1,4-bis(5-phenylfluorenyl-2-yl)benzene as a double (1)phenyl), "-thiazole, 2,5-bis(1-phenyl) m,3,4_oxadiazole, 2_(4,-tertiary butylbenzene^-""-linked from oxadiazole^double...naphthyl)'---diazole, hydrazine, 4-double [2 -(5-phenyloxadiazolyl)]benzene, 1,4-bis[2-(5, phenylfluorene) Base)-4-tertiary butylphenyl], 2_(4,_tris-butylphenyl)-b (4,biphenyl)-1,3,4-quinonedifluorene, 2,5-bis(p-naphthyl) , 3, 4_嗟二坐, 1,4-bis[2-(5-phenylindenyl)benzene, 2_(4'-tris-butylphenyl)-5-(4"-biphenyl H,3,4_three saliva, 3_.(4_biphenyl)+phenyl_5_ tertiary butylphenyl-1,2,4-triazole, 2,5-bis(1-naphthyl)_丨, 3,4_triazole, 1,4-bis[2-(5-phenyltris)]benzene, etc., but is not limited thereto. The organic electroluminescent device of the present invention is used to increase the charge. Injecting steepness can also provide an inorganic compound layer between the light-emitting layer and the electrode. 319891 13 200840819 The inorganic compound layer can be, for example, a metal such as LiF, Li2, Ra, Sr, BaF, SrF2 or a soil of a soil tester. a gasification, an oxide, etc. The conductivity and material used in the anode of the organic electroluminescent device of the present invention are those having a work function (work f unct ion) of more than about 4 eV, for example, carbon atoms, inscriptions, Hunger, iron, Ming, nickel, tungsten, silver m and these mouths to I TO (substance containing tin oxide 5 to (10) in indium oxide) The tin oxide, indium oxide, etc. used in the board and the substrate are oxidized to the genus, and the organic conductive resin such as polyphenylene or poly-bieha is used in the step-by-step manner. However, the conductive material used for the anode is used. The working function is better than that of the conductive material used for the cathode of the component. The conductive material used in the cathode has a working function smaller than that of the research left=two tin, the wrong, the titanium m, In the alloy system, for example, the ratio of the town/silver and the alloy is limited by the temperature of the vapor deposition source and the ring shape (four). However, in order to entangle the anode and cathode of the cathode, the second layer is also the structure of the organic layer of the present invention. In the light wavelength region, the transparent electrode can be used at least in the surface of the device, and the conductive material can be used, or the method of sputtering or sputtering can be used to ensure the transparency of the pre-dip by vapor deposition. And get it. The electrode of the light-emitting surface is preferably such that the light transmittance is (10) or more. 319891 14 200840819 The substrate is not particularly limited as long as it has mechanical and thermal strength and transparency, and may be, for example, a glass substrate or a transparent resin film. Examples of the transparent resin film include polyethylene, ethylene-ethyl acetate, copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polyfluorenyl, methyl acrylate, polyvinyl chloride, polyethylene. Alcohol, polyvinyl butyral, lonsone, polyscaled ketone, polysul f one, polyether oxime, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene Copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, polyvinylidene fluoride (polyvinyl idene f luoride), polyester, polycarbonate, polyurethane, polyamine, polyether Amine, polyimine, and the like. In order to improve the stability to temperature, humidity, environment, and the like, the organic electroluminescent device of the present invention can also provide a protective layer on the surface of the element or protect the entire element by eucalyptus oil, resin, or the like. Further, the formation of each layer of the organic electroluminescence element can be performed by a dry film formation method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film formation such as a spin coating method, a dipping, or a shower coating. Any of the laws. The film thickness is not particularly limited, but the film thickness is usually in the range of 5 nm to 10/zm, and preferably in the range of 1 Onm to 0.2 m/z m. In the case of the wet film formation method, the compound represented by the above formula (1) can be dissolved or dispersed in each solvent to prepare a solvent such as ethanol, chloroform, tetrahydroethylene, or dioxane (ane). film. The dry film forming method is preferably a vacuum vapor deposition method, using a vacuum vapor deposition apparatus, having a vacuum degree of 2×10 −3 Pa or less, and adjusting the substrate temperature to room temperature, and then heating in a vapor deposition bath to have the above-described formula of the present invention ( 1) The aroma shown is 3 319891 200840819: The organic sulfonium compound of the base group can be adjusted by evaporating the material. At this time, in order to control the temperature of the vapor deposition source, it is preferable to use a contact base type sample or a non-made red temperature material. In order to control the inside and use, a vapor deposition film thickness gauge is used. ^Mineral thickness gauge is used: the crystal vibrating cover set in the face of the evaporation source. The oscillation frequency of the vibration (4) is measured. [Measurement of adhesion (4) The crystal vibration = the weight of the vapor on the surface, and the weight measured from the amine Thick form. ^

The co-steaming system of the compound represented by the above formula (1) and the luminescent material or other matrix material can be carried out by separately controlling the vapor deposition source and independently controlling the '/JIL degree. Here, in order to improve film formation, prevent pinhole formation of the film, etc., any organic film layer can be used: polyethylene, polycarbonate, polyacrylic acid vinegar, polyester, polyamine, polyamine vinegar, polyfluorene "Insulating resin such as methyl acetal, polyacrylic acid, S, cellulose, and these copolymers, poly-[------------ A resin such as a polymer or the like, or an antioxidant, an ultraviolet absorber, or a plasticizer-specific additive. (Examples) Hereinafter, the present invention will be specifically described by way of examples, but the scope of the present invention is not Restricted to this. (Bei] Example 1 (Synthesis of bis[3 - (N-carbazolyl)phenyl]diphenylnonane) ^ After replacing 25 ml of Schlenk tube with argon, add N-(3) Monobromo) oxazolidine · 68g (2·lmm〇l) and THF (8ml), and cooled to -78 C ° with a dry ice-methanol bath 319891 16 200840819 2. After stirring at the same temperature for 30 minutes, add diphenyldichlorodecane 210/z 1 (1.0 mmol) and stir at the same temperature for 1 59. After that, it is warmed to QC 'and stirred at the same temperature for 4 hours. The reaction mixture is added to water-1' and extracted with dichlorohydrazine (30m 1x1, 1 〇mlχ2), and then distilled under reduced pressure by an evaporator. The solvent was removed, and the crude product was purified by column chromatography (eluent: hexanes / ethyl acetate = 1 / / / / / / / / (Yield 80%) • 3H-NMR (300MHz, CDQ) δ: 8.12-8. 08(m, 4H), 7, 83-7. 82(m, 2 Η), 7· 71-7· 62(m,10H),7· 46-7· 39(m,6H), 7· 34-7· 20(m,12H) FAB-MS(M/e) : 666(M+) EA: observation C ···················································· -oxazolyl)phenyl]diphenylnonane) After substituting argon in 25 ml of Schlenk tube, n-(3-bromophenyl)carbazole oxime 68g (2.1 mmol) and THF (8 ml) were added. ), and cooled to -78 ° C in a dry ice-methanol bath. 2 59 ml (1·7 M, 4·4 mmol) of a tertiary butyl lithium/n-pentane solution was added dropwise, and after stirring at the same temperature for 30 minutes, two were added. Phenyldichloromethane 222 // 1 (1·Ommol After stirring at the same temperature, the mixture was upgraded to 〇 c ' and stirred at the same temperature for 2 hours. The reaction mixture was added to water (100 ml) and extracted with dichloromethane (3 〇 mixi, i 〇 mixture 2), and the solvent was distilled off under reduced pressure by evaporation. The crude reaction product was purified by column chromatography (hexane: ethyl acetate / ethyl acetate = 1 / / / / / / / / (Yield 81%) 319891 17 200840819 H-NMR (300MHz, CDCy δ: 8·12-8· 09(m, 4H), 7·80-7. 79(m, 2 'H), 7·67_7· 61(m,1〇H),7·44—7, 40(m,6H), 7· 36-7· 21(m, 12H) FAB-MS(M/e) : 712(M+) ▲ EA : Observed value C: 80·84, H: 4.87, N: 3.85 ▲ 4 value C: 81·04, H: 4·82, N: 3·94 (C3) (made in the luminescent layer with double [3 - (N-carbazolyl)phenyl] diphenyl decane blue phosphorescent organic electroluminescence device) EI glass with indium tin oxide (hereinafter referred to as IT 〇) film is used as a transparent film The electrode substrate was vacuum-forged with a ULVAC machine, and vacuum-deposited on the same substrate at 2x1 (vacuum below T3pa, sequentially: 1'1 and [4 (--4-toluamino)phenyl)] The hole transport layer 3 composed of cyclohexane (hereinafter abbreviated as TAPC) has a film thickness of 4 Å, and contains a known cyan luminescent light in the double "-(n-carbazolyl)phenyl]diphenyl zephyr (2). Material bis [(4, 6-difluorophenyl) pyridinyl (pyridinat〇)-N, c2^ picolinto) (hereinafter referred to as FIrpic) 5.3 weight The hair layer _ light layer 4 film thickness is 30, from 3-(4-biphenyl)-4-phenyl-5-tridecyl-1,2,4-triazole (sublimation refined products, below A hole composed of TAZ). The barrier layer (h〇leblocking hyer) 5 has a film thickness of 30 nm, and the electron transport layer 6 composed of lithium fluoride (hereinafter abbreviated as UF) is (a) a face, and the aluminum as the electrode 7 (A1) is an electron-exciting element produced by l〇〇nm. Further, vacuum evaporation is performed by charging a raw material in a crucible placed facing the substrate, and heating the raw materials of the crucibles. ΙΤ0 electrode 2 is used as the positive electrode, and A1 electrode 7 is used as the negative electrode for energization. If the voltage between the electrodes is gradually increased, the component emits blue light from the vicinity of +(10) 319891 18 200840819 1 with a clearly visible degree to the naked eye, and at + 2iv Light of 1880 cd/m2 is emitted, and the luminous current efficiency of the element is obtained by the following equation: Current efficiency = (luminous luminance per unit area) 八 electric current per unit area ▲ flow density) Current efficiency obtained by performing this Attached to + please be 3 9icd/A. Use the Precise Gauges organic EL evaluation device to evaluate this F member luminescent color. + _ Obtained from the spectrum of m, Norway 〇1 chromaticity coordinates value calculated by the electrode system between the claw square x =. 16, y = committed. (Inventive Example 4) (Preparation of a phosphorescent organic electroluminescent device having a bis[3 succinyl) phenyl] phenyl decane in a light-emitting layer) For the transparent electrode substrate, using ULVAC machined vacuum base depletion | LV ^ ^ ^ ^ ... plating, on the same substrate in 2xl 〇 _3Pa 3 film followed by vacuum evaporation: electric transport layer consisting of tapc In the double [3 one (N-sityl) phenyl] diphenyl mis-fired (3) 'J two coffee 4.9% by weight of the light-emitting layer 4 film thickness 3 〇, from the TAZ hole barrier layer 5 is 30nm, by LiF The component of the electron transport layer 6 is composed. And '(A1) is 100 yan' and electro-excitation light is produced. Further, the vacuum steaming system is carried out by placing the materials in the (4) facing the substrate, and heating the raw materials of each (4). The anode electrode 2 of the 7G piece is used as the positive electrode, and the Ai fish is energized. If i豕呶4m r is negative 4^, the voltage between the electrodes is gradually increased, and the component is emitted from the vicinity of +4V to the naked eye. , the main aunt 41 / attached

The doorman has a blue light of the degree of π疋 recognition, and finds that this is 7.65cd/« emitted 3530cd/m2 in the form of + 22V 319891 19 200840819. According to the luminous current efficiency of the parts described in the third embodiment, the current efficiency is evaluated by using the Precise Gauges organic EL 哗 # 取 ^ ^ ^ ^ ^ ^ 衣 讪 讪 ^ ^ ^ ^ ^ ^ First color. From the voltage between the electrodes + 22v Fengshan Qi ^ ^: production to scare the first sputum, according to JIS Z8701 water out of the color seat; f indication value x = 〇. 16, y = 34. (Comparative Example 1) (Production of a disc-light organic electroluminescence element having a light-emitting sound material 枓UA + f and (N-carbazolyl) benzene (now a light layer material) in the light-emitting layer was used. When making (10) the glass of the film is used as a transparent electrode substrate, :=1C: vacuum evaporation device, on the same substrate, in the 3 film, Γ 又 又 ^ ^ ^ ^ 真空 真空 真空 真空 真空 真空 真空 真空 真空 电 电 电 电 电 电 电3 is 4 〇 nm, in the material of the existing luminescent layer, the - (four) ten sitting phantom (below _ heart) contains Firpic 54% by weight of illuminating sound = 3W thick by TAZ hole blocking layer 5 is 3_, and the electron transport layer 6 is made up of 5.5nm, and is made of H, and an electroluminescent element is produced. The fortune of the package pole 7 (6) is the second steaming (four) via the face In the (4) where the substrate is placed, it is carried out by heating the raw materials of each of the hanging stalks. :: The 70 ΙΤ 0 electrode 2 is the positive electrode, and the A1 electrode 7 is the negative electrode. The component is degraded from +5V to a blue light of a degree that can be clearly recognized by the naked eye, and is at a light of +21. According to the formula described in the third embodiment, the efficiency of each of the cows is determined. The current efficiency is + 19 V ^ 2 85 cd/A. The luminescent color of this element 319891 20 200840819 is evaluated using an organic EL evaluation device made by Precise Gauges. The chromaticity coordinate value obtained by the voltage between electrodes + 21 θ is the known spectrum. According to JIS Ζ8701 广方妥 L ^ u· 0· 34. (Usage possibilities on wood production) The present invention relates to an electroluminescent device for use in, for example, a light-emitting device of a hanging television or a mobile phone 'Photocopying machine, printer 2 _: light source such as surface meter, etc. _ / Backlight of day and night, or meter r, especially / original cheek no panel, signal light, etc. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a current density_brightness curve of a light-emitting element of Examples 3 and 4 and Comparative Example i. Fig. 2 is a peak luminance of the light-emitting elements of Examples 3 and 4 and Comparative Example The EL spectrum of the electron-excited blue phosphorescent organic electro-optical IT 0 transparent electrode light-emitting layer electron transport layer 3 is the structure of the light-emitting elements of Examples 3 and 4 and the comparative example.

[Description of main components] Glass substrate; Hole transport layer f Hole barrier Cui Lu electrode 319^91 21

Claims (1)

200840819 X. Patent application scope: ‘system as general formula (1) 1. A bis(3-arylamino)diphenyl metal compound (wherein the lanthanoid atom represents a ruthenium atom or a ruthenium atom; and the Arl and Ar2 systems may be the same or different, and represent an aryl group or a heteroaryl group, Any of the chlorine atoms on the aryl group may also be substituted by a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an arylalkyl group, an alkoxy group, or an aryloxy group, in addition to the adjacent Arl, It can be directly or indirectly connected by lysine, sulphur, refractory base, oxygen extension base or sulfur extension base. 2. An organic electroluminescent device, which is an organic electroluminescent device in which a light-emitting layer or a thin layer of a plurality of organic compounds containing a light-emitting layer is formed between the opposite electrodes, wherein at least the light-emitting layer contains a patent application range. Metal compound of item L. 3. If you apply for a patent scope! a bis(3-arylamino)diphenyl metal compound in which a bis(3-arylamino)diphenyl metal compound is selected from the group consisting of bis[3-CN-carbazolyl)phenyl] At least a compound of the group consisting of phenyl decane and bis[3_(κ-saltyl)phenyl]diphenyl-synthesized. 4. An organic electroluminescence element which is an organic electroluminescence element which is formed by forming a light-emitting layer or a thin layer of a plurality of organic compound layers having a light layer or a light layer, and is characterized in that it is contained in at least the light-emitting layer. Patent application No. 319891 22 200840819 3 metal compounds.