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  • H10K50/00—Organic light-emitting devices
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  • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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  • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
  • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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  • Y10S428/00—Stock material or miscellaneous articles
  • Y10S428/917—Electroluminescent

Definitions

• the present invention relates to an organic electroluminescent element (organic EL element) in which an organic layer having a light emitting region is provided between an anode and a cathode, and a light emitting or display device using the same, such as a display device.
• organic electroluminescent element organic EL element
• CTRs cathode ray tubes
• Liquid crystal displays such as active matrix drive have been commercialized as lightweight, high-efficiency flat panel displays.However, liquid crystal displays have a narrow viewing angle and do not emit light. There are problems such as the large power consumption of the backlight and the lack of sufficient response performance to high-definition high-speed video signals expected to be put to practical use in the future. In particular, it is difficult to manufacture a large screen display, and there are also problems such as high cost.
• organic electroluminescent element using an organic light emitting material has been attracting attention as a flat panel display that can solve these problems. That is, by using an organic compound as a light emitting material, realization of a flat panel display which is self-luminous, has a high response speed, and has no viewing angle dependence is expected.
• the structure of an organic electroluminescent device is a device in which an organic thin film containing a light emitting material that emits light by current injection is formed between a translucent positive electrode and a metal cathode.
• CW Tang SA VanSlyke et al., Applied Physics Letters 5 1 Vol. 12 No. 9 9 3 9 pp. 15 (19987)
• two types of organic thin films were used: thin films composed of hole transport materials and thin films composed of electron transport materials.
• As the layer structure we have developed a device structure that emits light by recombination of electrons and holes injected from each electrode into the organic thin film (organic EL device with Sindal hetero structure).
• either the hole transporting material or the electron transporting material also functions as the light emitting material, and light emission occurs in a wavelength band corresponding to the energy gap between the ground state and the excited state of the light emitting material.
• Adachi Adachi, S. Tokita, T. TsutsuK S. Saito, etc.
• the diversity of organic compounds used in light-emitting materials has the advantage that the emission color can be changed arbitrarily by changing the molecular structure theoretically. Therefore, by applying molecular design, the three colors of R (red), G (green), and B (blue) with good color purity required for a full-color display can be compared with thin-film EL devices using inorganic substances. It can be said that it is easy.
• Patent Document 1 described below proposes that a specific styryl compound be used as an organic electroluminescent material.
• Non-Patent Document 1 Chem. Func. Dyes, Proc. Int. Sy Immediately, 2nd P. 536 (1993)
• Non-patent document South Dog 2 T. Tsutsui, DU Kim, Inorganic and Organic electroluminescence conference (1996, Ber 1 in)
• Patent Document 1 Japanese Patent Application Laid-Open No. 7-188649 (claims, page 5, right column, line 8 to page 22, right column, line 5, FIG. 1 to FIG. 3)
• Non-Patent Document 2 BSB- BCN is realizes a 1 0 0 0 cd Zm 2 or more high brightness, and chromaticity as red corresponding to full-color ones complete I can't say.
• Patent Document 1 proposes that a specific styryl compound be used as an organic electroluminescent material.
• the objective emission color is blue, and it is intended to obtain another color wavelength such as red. It is not something.
• an organic electroluminescent device having a light-emitting region composed of a specific styryl compound and a material capable of efficiently transmitting energy thereto.
• the present inventors have found that if a device is manufactured, a light-emitting device having high luminance, high reliability, good thermal stability, and excellent color purity at a relatively long wavelength such as red can be provided, and the present invention has been achieved. Things. BRIEF DESCRIPTION OF THE FIGURES
• FIG. 1 is a schematic sectional view of a main part of an organic electroluminescent device according to the present invention.
• FIG. 2 is a schematic cross-sectional view of a main part of another example of the organic electroluminescent device.
• FIG. 3 is a schematic sectional view of a main part of another example of the organic electroluminescent device.
• FIG. 4 is a schematic cross-sectional view of a main part of another example of the organic electroluminescent device.
• FIG. 5 is a schematic sectional view of a main part of another example of the organic electroluminescent device.
• FIG. 6 is a schematic cross-sectional view of a main part of still another example of the organic electroluminescent device.
• FIG. 7 is a configuration diagram of a full-color flat display using the same organic electroluminescent device.
• the present invention provides an organic electroluminescent device including an organic layer having a light-emitting region provided between an anode and a cathode, and including, as a component, an organic substance that emits light by current injection. At least one layer comprises at least one styryl compound represented by the following general formula [I] (there may be at least one styryl compound, or at least two styryl compounds);
• An organic electroluminescent device (hereinafter referred to as a first organic EL device of the present invention having a power S) comprising a mixed layer containing a material having the following general formula [I]:
• X is a group represented by any of the following general formulas (1) to (13).
• R 1 to R 5 is a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, an alkyl group which may have a substituent, and a substituent. Selected from alkoxyl groups which may have Groups, which may be the same or different.
• R 6 to R 1119 represent a halogen atom such as a hydrogen atom, a fluorine atom, a chlorine atom or the like (the same applies hereinafter), a nitro group, a cyano group, and a trifluoro group.
• Y is a group represented by any of the following general formulas (14) to (16).
• Z 1 and Z 2 are each selected from a hydrogen atom, an alkyl group optionally having a substituent, and an aryl group optionally having a substituent.
• R 11 () to R 126 each represent a hydrogen atom or a substituent.
• the styryl compound represented by the general formula [I] includes a styryl compound having a molecular structure represented by the following structural formulas (17) to 1 to (17) _86. At least one of them can be used.
• the introduction position of the cyano group in the structural formulas (17) to 13 gives a relatively short emission wavelength as compared with the other introduction positions, but in the latter case, The molecular skeleton is stabilized, and the emission wavelength can be made longer.
• Examples of the material that can be used to form the mixed layer containing the compound of the present invention include, in addition to the compound of the present invention, a hole transporting material (for example, aromatic amines and the like), an electron transporting material (for example, a 1 q 3, pyrazolines, Okisaji ⁇ zone Ichiru acids, Toriazo Ichiru acids, phenylene, etc.), or in general a series of compounds for use as a red onset light de one dopant (D CM and analogs Compounds, porphyrins, phthalocyanines, perylene compounds, Nile Red, squarylium compounds, etc.) (hereinafter the same).
• a hole transporting material for example, aromatic amines and the like
• an electron transporting material for example, a 1 q 3, pyrazolines, Okisaji ⁇ zone Ichiru acids, Toriazo Ichiru acids, phenylene, etc.
• the organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and at least the electron transport layer of the organic laminated structure is It may be composed of the mixed layer containing at least one styryl compound represented by any one of the general formula [I] or the structural formula (17) -1 to (17) -86.
• the organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and at least the hole transport layer of the organic laminated structure has the general formula [I Or the mixed layer containing at least one styryl compound represented by any one of the structural formulas (17) to 1 to (17) to 86.
• the organic layer is an organic layer in which a hole transport layer and an electron transport layer are laminated. Having a layer structure, wherein the hole transport layer is formed of a styryl compound represented by any one of the general formula [I] or the structural formula (17) —1 to (17) -86.
• the electron transport layer comprises the mixed layer containing at least one kind, and is represented by any one of the general formula [I] or the structural formula (17) — 1 to (17) _86.
• the mixed layer containing at least one styryl compound.
• the organic layer has an organic laminated structure in which a hole transporting layer, a light emitting layer, and an electron transporting layer are laminated, and at least the light emitting layer of the organic laminated structure has the general formula [I Or a mixed layer containing at least one styryl compound represented by any one of the structural formulas (17) — 1 to (17) -86.
• At least one styryl compound represented by any one of the general formula [I] or the structural formula (17) —1 to (17) —86 is in the range of 5 to 90. It may be mixed with the above-mentioned material having charge transporting ability in a concentration range of weight%.
• the mixed layer may include at least one styryl compound represented by the general conductor [I] or any one of the structural formulas (17) to 1 to (17) -86, and It preferably contains a red or orange light-emitting dye having an emission maximum in the range of 700 nm.
• the “mixed layer” described above typically means a mixed layer of the styryl compound and another compound, but may also include two or more of the styryl compounds included in the styryl compound.
• a mixed layer of styryl compounds may also mean. With such a mixed layer, red light emission or the like having desired luminance or chromaticity can be generated by a combination of a plurality of compounds.
• the organic electroluminescent element of the present invention is used, for example, for at least a part of a pixel. Suitable for light-emitting or display devices configured as display devices (Hereinafter the same).
• FIGS. 1 to 6 show examples of the organic electroluminescent device (organic EL device) based on the present invention.
• FIG. 1 shows a top-emission type organic electroluminescent element A through which emitted light 20 passes through the cathode 3, and the emitted light 20 can also be observed from the sealing layer 4 side.
• FIG. 2 shows a bottom emission type organic electroluminescent device B that also obtains reflected light from the cathode 3 as emitted light 20.
• reference numeral 1 denotes a substrate for forming an organic electroluminescent device. Glass, plastic and other suitable materials can be used. When the organic electroluminescent device is used in combination with another display device, the substrate can be shared.
• the anode 2 is a transparent, translucent or opaque electrodes, ITO (Ind i um t in ox i de), S n 0 2, A u, A g, A 1, C r may be used.
• Reference numeral 5 denotes an organic layer, which contains the above styryl compound as a light emitting material (provided that at least one styryl compound is mixed with another compound or a plurality of styryl compounds are used in combination) Content: the same applies hereinafter).
• the light emitting layer various conventionally known structures can be used as a layer structure for obtaining the organic electroluminescent light 20.
• the hole transporting layer and the electron transporting layer have a structure in which thin films of a plurality of types of materials are laminated, or It does not prevent the use of thin films composed of a mixture of these materials.
• At least one kind of fluorescent material is used, and this thin film is sandwiched between a hole transport layer and an electron transport layer.
• a structure in which at least one fluorescent material is included in the hole transport layer or the electron transport layer, or both of them may be used.
• a thin film for controlling the transport of holes (holes) or electrons can be included in the layer structure.
• the styryl compound represented by the above general formula [I] has both electron transporting performance and hole transporting performance, it can be used as a mixed light emitting layer with an electron transporting material in the device structure, or as a hole transporting material. Can also be used as a mixed light emitting layer.
• a structure in which a mixed layer containing the compound is interposed between an electron transporting layer and a hole transporting layer can be used as a light emitting material.
• a mixed layer containing two or more different styryl compounds represented by the above general formula [I] may be used as the light emitting layer. By selecting an appropriate combination of two or more compounds, it is possible to arbitrarily select the emission color without significantly changing the electrical characteristics of the device.
• any of R 6 to R 1 () 9 may have a halogen atom,
• a substituent such as a group, a cyano group, a trifluoromethyl group, an alkyl group which may have a substituent, or an alkoxyl group which may have a substituent, to form a crystal of a thin film forming a light emitting layer. It is possible to suppress the formation of the light emitting element and improve the amorphous property, and as a result, it is possible to improve the reliability (particularly, the half life) of the light emitting element.
• reference numeral 3 denotes a cathode.
• a metal such as Ag, Au, Al, Cr, In, or a combination of this metal and Li, Mg, Ca
• An alloy with an active metal such as, or a structure in which these are laminated can be used (hereinafter the same).
• the cathode is further alkali metal or alkaline earth metal oxides, lithium compound may have a structure in which a composite or laminated (L i F, L i 2 0 , etc.) or the like (hereinafter, the same).
• reference numeral 4 denotes a sealing layer, and the effect is improved by adopting a structure that covers the entire organic electroluminescent element. As long as airtightness is maintained, an appropriate material can be used.
• the organic layer has an organic laminated structure (single heterostructure) in which a hole transport layer and an electron transport layer are laminated, and the hole transport layer or the electron transport layer A mixture layer containing the styryl compound may be used as a material for forming the above.
• the organic layer has an organic laminated structure (double hetero structure) in which a hole transport layer, a light emitting layer, and an electron transport layer are sequentially laminated, and contains the styryl compound as a material for forming the light emitting layer. Layers may be used.
• the mixing ratio of the styryl compound in these mixed layers is desirably 5 to 90% by weight.
• FIG. 3 shows an example of an organic electroluminescent device having such an organic laminated structure.
• FIG. 3 shows that a light-transmissive anode 2, a hole transport layer 6, and an electron transport layer 7 are formed on a transparent substrate 1.
• a cathode 3 having a laminated structure in which the organic layer 5a is sequentially laminated, and the laminated structure is sealed by a sealing layer 4 to form a single-heterostructure bottom emission organic electroluminescence.
• a sealing layer 4 to form a single-heterostructure bottom emission organic electroluminescence.
• FIG. 4 shows that a light-transmitting anode 2, an organic layer 5 b composed of a hole transport layer 10, a light-emitting layer 11, and an electron transport layer 12 are formed on a light-transmitting substrate 1.
• Cathode 3 are sequentially laminated, and this laminated structure is sealed with a sealing layer 4 to provide a double-heterostructure bottom emission organic electroluminescent device D.
• the holes injected from the anode 2 pass through the hole transport layer 10 and the cathode 3
• the electrons injected from the GaN layer reach the light emitting layer 11 via the electron transport layer 12.
• the recombination of the electron Z holes occurs to generate excitons, and the excitons emit light of a predetermined wavelength.
• the materials usable as the hole transporting material having the charge transporting ability include benzidine or a derivative thereof, styrylamine or a derivative thereof, triphenylmethane or a derivative thereof. Porphyrin or a derivative thereof, triazole or a derivative thereof, imidazole or a derivative thereof, oxadiazole or a derivative thereof, polyarylalkane or a derivative thereof, phenylenediamine or a derivative thereof, arylamine or a derivative thereof, oxazole or a derivative thereof.
• Anthracene or a derivative thereof fluorenone or a derivative thereof, hydrazone or a derivative thereof, stilbene or a derivative thereof, or a polysilane compound, a vinylcarbazole compound, a thiophene compound, an aniline compound, or the like. Containing cyclic conjugated system of the monomers one, oligomers, polymers and the like can be mentioned up (hereinafter, the same).
• Examples of materials that can be used as the electron transporting material having a charge transporting property include quinoline or a derivative thereof, perylene or a derivative thereof, and bistilyl. And its derivatives, pyrazine and its derivatives (the same applies hereinafter).
• Specific examples thereof include 8-hydroxyquinoline aluminum (Alq 3 ), anthracene, naphthalene, phenanthrene, pyrene, chrysene, perylene, butadiene, coumarin, acridine, stilbene, and derivatives thereof.
• a light-transmitting material such as glass or plastic can be appropriately used. Further, this substrate may be shared when used in combination with another display element, or when the laminated structures shown in FIGS. 3 and 4 are arranged in a matrix.
• the anode 2 is a transparent electrode, can be used IT_ ⁇ or S N_ ⁇ 2, etc., between the anode 2 and the hole transport layer 6 (or the hole transport layer 1 0), charge injection inlet
• inorganic, organic or organometallic compounds such as 2-TNATA (4,4,, 4 "tris (2-naphthylphenylamino) triphenylamine) and US Pat. No. 4,720,044 32
• a thin film made of a ponorefilin compound or the like described in No. 2 (the same applies hereinafter) may be provided.
• the sealing layer 4 is formed of a conductive material such as a metal, it may be provided on the side surface of the anode 2.
• An insulating film may be provided.
• the organic layer 5a in the organic electroluminescent element C is an organic layer in which the hole transport layer 6 and the electron transport layer 7 are laminated, and one or both of them are provided.
• a mixed layer containing the above styryl compound a luminescent hole transporting layer 6 or an electron transporting layer 7 may be formed.
• the organic layer 5b in the organic electroluminescent device D is an organic layer in which the light emitting layer 11 and the electron transport layer 12 made of a mixture containing the hole transport layer 10 and the styryl compound described above are laminated.
• Various laminated structures can be adopted. For example, one or both of the hole transport layer and the electron transport layer may emit light.
• a hole transport layer in which a plurality of types of hole transport materials are stacked may be formed in order to improve hole transport performance.
• the light emitting layer may be the electron transporting light emitting layer 7, but depending on the voltage applied from the power supply 8, light may be emitted from the hole transporting layer 6 or its interface.
• the light emitting layer may be the electron transport layer 12 or the hole transport layer 10 other than the layer 11.
• the light emitting layer 11 using at least one kind of fluorescent material is sandwiched between the hole transport layer and the electron transport layer.
• a structure in which this fluorescent material is contained in the hole transporting layer or the electron transporting layer, or both of these layers may be formed.
• a thin film such as a hole blocking layer or an exciton generation layer for controlling the transport of holes or electrons can be included in the layer configuration.
• an alloy of an active metal such as Li, Mg, or Ca and a metal such as Ag, Al, or In can be used, and these metal layers are laminated. It may be a structure. Incidentally, by appropriately selecting the thickness and material of the cathode, an organic electroluminescent device suitable for the intended use can be produced.
• the sealing layer 4 functions as a sealing film, and the charge injection efficiency and the luminous efficiency can be improved by adopting a structure that covers the entire organic electroluminescent element. If the airtightness is maintained, aluminum, gold, chrome, etc. Materials such as single metals or alloys, silicon compounds such as silicon oxide and silicon nitride, and organic substances can be selected as appropriate.
• FIG. 5 shows a laminated structure in which an anode 2, an organic layer 5c composed of a hole transport layer 6 and an electron transport layer 7, and a transparent or translucent cathode 3 are sequentially laminated on a substrate 1.
• the stacked structure is sealed by a sealing layer 4 to form a top emission type organic electroluminescent element E having a single hetero structure.
• emission light 20 of a predetermined wavelength is generated from the interface between the hole transport layer 6 and the electron transport layer 7, and this emission is observed from the cathode 3 or the sealing layer 4 side.
• FIG. 6 shows an anode 2, an organic layer 5d composed of a hole injection layer 9, a hole transport layer 10, a light emitting layer 11, and an electron transport layer 12 on a substrate 1, and a transparent or translucent
• a top emission type organic electroluminescent device F having a laminated structure in which the cathode 3 is sequentially laminated, and the laminated structure is sealed by a sealing layer 4. Also in this organic electroluminescent device, as in the organic electroluminescent device shown in FIG. 4, recombination of the electron Z hole occurs in the light emitting layer 11 to generate an exciton, and the exciton is generated from the exciton. Light emission of a predetermined wavelength is generated.
• the substrate 1 is made of a light-reflective material such as, for example, Ag, Au, Al, Cr, In, or an alloy thereof as appropriate. This substrate may be shared when it can be used, when it is used in combination with another display element, or when the laminated structures shown in FIGS. 5 and 6 are arranged in a matrix.
• the anode 2 on the substrate 1 is a reflective electrode, and can be Ag, Au, A1, Cr, In, or an alloy thereof, or can be used by laminating ITO or the like.
• the thickness is preferably not less than 50 nm, and can be not more than 200 nm, in consideration of film formability and reflectivity.
• the substrate 1 is not limited to the light-reflective material described above, but may be a transparent or translucent material such as glass.
• a hole injection layer 9 made of an inorganic, organic, or organometallic compound is provided between the anode 2 and the hole transport layer 10 for the purpose of improving the charge injection efficiency. It may be provided.
• a hole injection layer 9 similar to the above may be provided between the anode 2 and the hole transport layer 6 in FIG.
• the sealing layer 4 is formed of a conductive material such as a metal
• an insulating film may be provided on the side surface of the anode 2 for insulation separation.
• the organic layer 5c in the organic electroluminescent element E is an organic layer in which a hole transport layer 6 and an electron transport layer 7 are laminated, and as a mixed layer containing the styryl compound described above in one or both of them.
• the luminescent hole transport layer 6 or the electron transport layer 7 may be formed.
• the organic layer 5 d in the organic electroluminescent element F is an organic layer in which the hole transport layer 10, the light emitting layer 11 composed of a mixture containing the above styryl compound, and the electron transport layer 12 are laminated.
• Various other laminated structures can be adopted. For example, one or both of the hole transport layer and the electron transport layer may emit light.
• a hole transport layer in which a plurality of types of hole transport materials are stacked may be formed in order to improve hole transport performance.
• the light emitting layer may be the electron transporting light emitting layer 7, but depending on the voltage applied from the power supply 8, light may be emitted from the hole transporting layer 6 or its interface.
• the light emitting layer may be the electron transport layer 12 or the hole transport layer 10 other than the layer 11.
• the light emitting layer 11 using at least one kind of fluorescent material is sandwiched between the hole transport layer and the electron transport layer.
• a structure in which this fluorescent material is contained in the hole transporting layer or the electron transporting layer, or both of these layers may be formed. In such cases, control of hole or electron transport is used to improve luminous efficiency.
• a thin film such as a hole blocking layer or an exciton generation layer for the layer structure.
• an alloy of an active metal such as Li, Mg, and Ca and a metal such as Ag, Al, and In can be used, and a structure in which these metal layers are laminated is used.
• An organic electroluminescent device suitable for the intended use can be manufactured by appropriately selecting the thickness and material of the cathode, but the thickness of the cathode is preferably 0.5 to 15 nm, and more preferably about 0.5 to 5 nm.
• the sealing layer 4 functions as a sealing film, and the charge injection efficiency and the luminous efficiency can be improved by adopting a structure that covers the entire organic electroluminescent element. If the airtightness is maintained, the material can be appropriately selected, such as a single metal such as aluminum, gold, chromium, silicon oxide, or silicon nitride, an alloy, or a compound.
• Each of the above-mentioned organic electroluminescent elements E and F has a structure in which the light emitting layer is sandwiched between the anode and the cathode, and the emitted light causes multiple interference between the anode and the cathode.
• the multiple interference effect can be positively utilized, and the element E can be used.
• F It is possible to control the emission wavelength extracted from F. As a result, the emission chromaticity can be improved.
• FIG. 7 shows a configuration example of a planar display using the organic electroluminescent device of the present invention. As shown, for example, in the case of a full color display, an organic layer 5 (organic layers 5a, 5b, 5c, 5d) capable of emitting three primary colors of red (R), green (G) and blue (B) is provided.
• organic layer 5 organic layers 5a, 5b, 5c, 5d
• the cathode 3 and the anode 2 can be provided in a stripe shape crossing each other, and are selected by the luminance signal circuit 14 and the control circuit 15 with a built-in shift register, and a signal voltage is applied to each of them.
• the organic layer at the position (pixel) where the selected cathode 3 and anode 2 intersect is configured to emit light.
• FIG. 7 is, for example, an 8 ⁇ 3 RGB simple matrix in which a hole transport layer and an organic layer 5 including at least one of a light emitting layer and an electron transport layer are provided between the cathode 3 and the anode 2.
• Figure 3 or Figure 4 see Figure 5 or Figure 6
• the cathode and anode are both patterned in stripes, are orthogonal to each other in a matrix, and are applied with signal voltages in a time series by the control circuit 15 and the luminance signal circuit 14 incorporated in the shift register. It is configured to emit light.
• the EL element having such a configuration can be used not only as a display for characters and symbols, but also as an image reproducing device.
• a 3 Omm ⁇ 30 mm glass substrate having an anode made of 100 nm thick ITO formed on one surface was set in a vacuum evaporation apparatus.
• a layer in which the styryl compound of 11 and ⁇ -NPD, which is a hole transport material, are mixed at a weight ratio of 1: 1 is formed as a hole transport layer (cum-emitting layer) to a thickness of, for example, 50 nm. Filmed.
• the deposition rates were each 0.1 nm / sec.
• a 1 q 3 Tris (8— Quinolinol) aluminum
• the film thickness also for instance 5 0 nm of the electron-transport layer composed of A lq 3, the evaporation rate was 0. 2 nm / sec.
• Alq 3 As a cathode material, a mixed film of Mg and Ag was adopted, which was also formed by vapor deposition, for example, with a mixture ratio of Mg and Ag of 1: 3 to a thickness of 200 nm, as shown in FIG. 3 according to Example 1. An organic electroluminescent device as described above was produced.
• Example 1 To the organic electroluminescent device of Example 1 thus manufactured, a forward bias DC voltage was applied in a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted red light. By spectral analysis, a spectrum having a light emission peak at about 620 nm was obtained. For spectrometry, a spectrometer using a photodiode array made by Otsuka Electronics Co., Ltd. as a detector was used. In addition, when the voltage-brightness measurement was performed, a luminance of 1500 cd / m 2 was obtained at 8 V.
• a 3 Omm ⁇ 30 mm glass substrate having an anode made of 100 nm thick ITO formed on one surface was set in a vacuum evaporation apparatus.
• a plurality of metal masks having a unit opening of 2.0 mm ⁇ 2.0 mm as a vapor deposition mask are arranged in close proximity to the substrate, and a vacuum vapor deposition method is used under the vacuum of 10 to 4 Pa or less to form the above structural formula.
• Hiichi NPD was deposited to a thickness of, for example, 50 nm.
• the deposition rate was 0.1 nmZ seconds.
• the structural formula (1-7) - 1 1 and the film thickness also for instance 50 nm of aminostyryl compound and the electron-transporting layer composed of A 1 q 3 Tokyo (and light emitting layer), deposited rates each 0. 2 nm / sec And
• a mixed film of Mg and Ag was employed, and this was also formed by vapor deposition to a thickness of 200 nm, for example, with a mixing ratio of Mg and Ag of 1: 3.
• An organic electroluminescent device as shown in FIG. 3 was produced.
• the organic electroluminescent device of Example 2 fabricated in this manner was evaluated for luminous characteristics by applying a forward bias DC voltage under a nitrogen atmosphere. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 60 nm. In addition, when voltage-luminance measurement was performed, a luminance of 260 cd / m 2 was obtained at 8 V.
• Example 3 This embodiment, of the styryl compound of the above general formula [I], the structural formula (1-7) - 1 1 of the styryl compound, mixed layer electron transport light-emitting of the A 1 q 3 of the structural formula This is an example in which a bottom emission type organic electroluminescent device having a double hetero structure was used as a layer.
• a 3 Omm ⁇ 30 mm glass substrate having an anode made of 100 nm thick ITO formed on one surface was set in a vacuum evaporation apparatus.
• a metal mask that having a plurality of 2. 0 mmX 2. unit openings 0mm as deposition mask arranged close to the substrate, under a vacuum of 10- 4 P a hereinafter by vacuum deposition of the structural formula at — NPD was deposited to a thickness of, for example, 30 nm.
• the deposition rate was 0.2 nmZ seconds.
• the structural formula (1 7) as the light emitting material - 1 1 styryl compound A lq 3 and the weight ratio of 1: was deposited in contact with the hole transport layer at 1.
• the structural formula (1-7) - 1 1 and the film thickness also for instance 30 nm light-emitting layer comprising a mixed layer of styryl compound and A 1 q 3, the deposition rate was at each 0. 2 NMZ seconds.
• a 1 d 3 of the above structural formula was deposited as an electron transporting material in contact with the light emitting layer.
• the thickness of A 1 q 3 is , for example, 30 nm, and the deposition rate is 0.
• a mixed film of Mg and Ag was adopted, and this was also formed by vapor deposition, for example, with a mixing ratio of Mg and Ag of 1: 3 to a thickness of 200 nm.
• the organic electroluminescent device as shown in was manufactured.
• the organic electroluminescent device of Example 3 thus manufactured was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted red light, which was found by spectrometry (as in Example 1) to have a peak at 60 nm. When voltage-brightness measurement was performed,
• a bottom emission type organic electroluminescent device having a double hetero structure is manufactured. This is an example.
• a 30 mm ⁇ 30 mm glass substrate on which an anode made of 100 nm thick ITO was formed on one surface was set in a vacuum evaporation apparatus.
• a plurality of metal masks each having a unit opening of 2.0 mm X 2.0 mm are placed in close proximity to the substrate as a vapor deposition mask, and the above-mentioned structural formula is formed by a vacuum vapor deposition method under a vacuum of 10 to 4 Pa or less.
• One NPD was formed to a thickness of, for example, 30 nm.
• the deposition rate was 0.2 nmZ seconds.
• a styryl compound of the above structural formula (17) -11 and a styryl compound of the above structural formula (17) -1 were co-evaporated in contact with the hole transport layer at a weight ratio of 1: 3. .
• the thickness of the light-emitting layer composed of a mixed layer of the styryl compound of the above structural formula (17) —11 and the styryl compound of the above structural formula (17) —1 is also set to, for example, 30 nm. 1 7) — 1 1
• the compound of formula (1) was 0.3 nm / sec
• the compound of formula (17) -1 was 0.3 nm / sec.
• a 1 d 3 of the above structural formula was deposited as an electron transporting material in contact with the light emitting layer.
• the film thickness of A 1 d 3 was , for example, 30 nm, and the deposition rate was 0.2 nm / sec.
• a cathode material As a cathode material, a mixture of Mg and Ag was adopted, and this was also formed by vapor deposition to a thickness of 200 nm, for example, with a mixture ratio of Mg and Ag of 1: 3.
• the organic electroluminescent device as shown in was manufactured.
• the organic electroluminescent device of Example 4 thus manufactured was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at 610 nm. A voltage-luminance measurement showed a luminance of 2200 cdZm 2 at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 5 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to improve the light emitting characteristics. evaluated.
• the luminescent color is orange.
• the luminescent peak is around 608 nm. Was obtained.
• voltage-luminance measurement was performed, a luminance of 1000 cd / m 2 was obtained at 8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. In addition, when a constant current was applied at an initial luminance of 300 cd / m 2 and continuous light emission was performed and forced deterioration was performed, it took 800 hours for the luminance to decrease to half.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 6 fabricated as described above was applied with a forward bias DC voltage in a nitrogen atmosphere to improve the luminescent characteristics. evaluated.
• the emitted light was orange, and the spectrum was measured in the same manner as in Example 1.
• Voltage-brightness measurement showed a luminance of 500 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method. ⁇ The organic EL device of Example 7 manufactured in this manner was subjected to a forward bias DC voltage in a nitrogen atmosphere under a nitrogen atmosphere to emit light. Was evaluated. The luminescent color was orange. As a result of spectral measurement in the same manner as in Example 1, a spectrum having a luminescent peak near 605 nm was obtained. When voltage-brightness measurement was performed, 8
• a luminance of 1200 cd dZm 2 was obtained at V.
• a mixed layer of the styryl compound of the following structural formula (17) 14 among the styryl compounds of the above general formula [I] and A 1 q 3 of the above structural formula was used.
• Example 8 the organic electroluminescent device of Example 8 in which both film forming method in conformity with Example 2 was prepared like this t fabricated organic electroluminescent device, the light emitting characteristics by applying a forward bias DC voltage in a nitrogen atmosphere was evaluated. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 600 nm. In addition, when voltage-luminance measurement was performed, a luminance of 1000 cdZm 2 was obtained at 8 V.
• Example 9 the organic electroluminescent device of Example 9 in which both film forming method in conformity with Example 2 was produced as the t fabricated organic electroluminescent device, light emission by adding Kawapeji bias dc voltage in a nitrogen atmosphere The properties were evaluated. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 615 nm. In addition, when voltage-luminance measurement was performed, a luminance of 900 cdZm 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• a forward bias DC voltage was applied to the organic electroluminescent device of Example 10 thus manufactured in a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 620 nm. Voltage-brightness measurement showed a luminance of 800 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 11 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light.
• spectrometry as in Example 1
• a luminance of 1100 cd / m 2 was obtained.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• a forward bias DC voltage was applied in a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 610 nm. Voltage-brightness measurement showed a luminance of 950 cd / m 2 at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 13 fabricated in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere.
• the emission color was orange, and the spectroscopic measurement was performed in the same manner as in Example 1.
• a spectrum having a light emission peak near 605 nm was obtained.
• a luminance of 850 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 15 thus manufactured was applied with a forward bias DC voltage under a nitrogen atmosphere to emit light.
• spectrometry as in Example 1
• a luminance of 1000 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 16 fabricated as described above was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated.
• the luminescent color was orange.
• the luminescent color was A spectrum having peaks was obtained.
• a luminance of 2000 cdZm 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method. ⁇ The organic electroluminescent device of Example 17 manufactured as described above was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. The luminescent color was clear, and the spectrum was measured in the same manner as in Example 1. As a result, a spectrum having a luminescent peak near 605 nm was obtained. Further, When a voltage was one luminance measurement, 1 8 0 0 luminance of c DZM 2 was obtained in 8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, it was left under a nitrogen atmosphere for one month, but no device degradation was observed. Further, by passing current value at an initial luminance 3 0 0 cd / m 2 at a constant and continuous light emission, when the forced deterioration, luminance half until 3300 hours.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 18 thus manufactured was applied with a forward bias DC voltage under a nitrogen atmosphere to emit light.
• spectrometry as in Example 1
• a luminance of 880 cdZm 2 was obtained at ⁇ 8 V.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 19 fabricated in this manner was applied with a forward bias DC voltage under a nitrogen atmosphere to improve the luminescent characteristics. evaluated. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 605 nm. Voltage-brightness measurement showed a luminance of 900 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• a light emitting characteristic was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to the organic electroluminescent device of Example 20 thus manufactured. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 700 nm.
• spectrometry as in Example 1
• a luminance of 250 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 21 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light. The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 690 nm.
• a voltage-brightness measurement was performed, a luminance of 180 cd / m 2 was obtained at .8 V.
• After fabrication of this organic electroluminescent device it was left under a nitrogen atmosphere for one month, but no device degradation was observed.
• a constant current was applied at an initial luminance of 300 cd / m 2 to continuously emit light, and the light was forcibly degraded, it took 450 hours until the luminance was reduced by half.
• Example 2 the organic electroluminescent element of the film formation method with Example 2 in compliance with the organic electroluminescent device was prepared t thus prepared was Example 2 2, light emission by applying a forward bias DC voltage in a nitrogen atmosphere The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 690 nm. Voltage-brightness measurement showed that a luminance of 330 cd / m 2 was obtained at 8 V.
• Example 2 3 This example shows that, among the styryl compounds of the general formula [I], the following structural formula (1)
• Example 23 the organic electroluminescent device of Example 23 with film forming method in conformity with Example 2 produced as the c fabricated organic electroluminescent device, the light emitting characteristics by applying a forward Iasu dc voltage in a nitrogen atmosphere was evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 680 nm. The voltage - was subjected to luminance measurement, the luminance of 280 c DZM 2 was obtained by 8V.
• Structural formula (17) — 21 An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method. A forward bias DC voltage was applied to the organic electroluminescent device of Example 24 thus manufactured in a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 680 nm. In addition, when a voltage-brightness measurement was performed, a luminance of 220 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 25 fabricated in this manner was placed under a nitrogen atmosphere. Then, a forward bias DC voltage was applied to evaluate the light emission characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 675 nm. In addition, voltage-brightness measurement showed a luminance of 240 cd / m at 8 V.
• Example 2 6 the organic electroluminescent element of the film formation method with Example 2 Example 2 6 produced as the t fabricated organic electroluminescent device in compliance with the light emission by applying a forward bias DC voltage in a nitrogen atmosphere The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 680 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 260 cdZm 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 27 fabricated in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere.
• the emission color was red, and the spectroscopic measurement was performed in the same manner as in Example 1.
• a spectrum having an emission peak near 680 nm was obtained.
• a luminance of 180 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 28 thus manufactured was applied with a forward bias DC voltage under a nitrogen atmosphere to emit light.
• the voltage - was subjected to luminance measurement, the luminance of 340 c DZM 2 was obtained in 8 V.
• Structural formula (17)-26 An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method. ⁇ The organic electroluminescent device of Example 29 fabricated in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 630 nm. Further, When a voltage was one luminance measurement, the luminance of 550 c DZM 2 was obtained in 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• a forward bias DC voltage was applied to the organic electroluminescent device of Example 30 thus manufactured in a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 64 nm.
• luminance of 700 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 31 fabricated in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 645 nm. Also, a voltage-brightness measurement was performed. A luminance of 720 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 32 manufactured in this manner was applied with a forward bias DC voltage under a nitrogen atmosphere.
• the emission color was red, and the spectrum was measured in the same manner as in Example 1.
• a spectrum having a light emission peak near 648 nm was obtained.
• the luminance of 7 50 c dZm 2 was obtained by 8V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 35 thus manufactured was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere.
• the emission color was red, and a spectrum having a luminescence peak at about 640 nm was obtained as a result of spectral measurement in the same manner as in Example 1.
• Voltage-luminance measurement was performed However, a luminance of 1150 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 36 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light.
• the properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 645 nm.
• a luminance of 118 cd / m 2 was obtained at .8 V.
• After fabrication of this organic electroluminescent device it was left under a nitrogen atmosphere for one month, but no device degradation was observed.
• the current value was kept constant at an initial luminance of 300 cd / m 2 to continuously emit light, and the light was forcibly degraded, it took 480 hours until the luminance was reduced to half.
• the organic electroluminescent device of Example 3 7 with film forming method in conformity with Example 2 was produced as the c fabricated organic electroluminescent device, light emission by applying a forward bias DC voltage in a nitrogen atmosphere The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 647 nm. Voltage-brightness measurement showed a luminance of 950 cd / m 2 at 8 V.
• Example 3 8 This embodiment, of the styryl compound of the general formula [I], the following structural formula (1 7) Single 3 and styryl compound of 5, mixed layer electron transport light-emitting layer between A 1 Q 3 of the structural formula This is an example in which a bottom emission type organic electroluminescent element having a single hetero structure was manufactured.
• the organic electroluminescent element of the film formation method with Example 2 in compliance with the organic electroluminescent device embodiment was fabricated c thus Preparation Example 3 8, emission by applying a forward bias DC voltage in a nitrogen atmosphere The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 62 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 890 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 39 thus manufactured was applied with a forward bias DC voltage under a nitrogen atmosphere to emit light.
• Voltage-brightness measurement showed that a luminance of 300 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 40 thus manufactured was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated.
• the emission color is orange
• a spectrum having an emission peak at around 580 nm was obtained as a result of the same spectroscopic measurement as in Example 1.
• Voltage-brightness measurement showed a luminance of 580 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 41 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light.
• the properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 600 nm.
• spectrometry as in Example 1
• a luminance of 6.2 cd / m 2 was obtained at .8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. Further, by passing current value at an initial luminance 3 0 0 cd / m 2 at a constant and continuous light emission, when the forced deterioration, luminance half until It was 1500 hours.
• the organic electroluminescent device of Example 42 with the film formation method in conformity with Example 2 was produced as the c fabricated organic electroluminescent device, the light emitting characteristics by applying a forward bias DC voltage in a nitrogen atmosphere was evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 600 nm. Further, When a voltage was one luminance measurement, 5 2 0 luminance of c DZM 2 was obtained in 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 43 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light.
• spectrometry as in Example 1
• a luminance of 750 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• a forward bias DC voltage was applied in a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 645 nm. Voltage-brightness measurement showed a luminance of 950 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method. ⁇ The organic electroluminescent device of Example 45 manufactured in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 600 nm. In addition, when voltage-luminance measurement was performed, luminance of 900 cd / m 2 was obtained at 8 V.
• this organic electroluminescent device After manufacturing this organic electroluminescent device, it was left under a nitrogen atmosphere for one month. No element deterioration was observed. In addition, when a constant current value was applied at an initial luminance of 300 cdZm 2 to continuously emit light, and the light was forcibly degraded, it took 150 hours until the luminance was reduced to half.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 46 thus manufactured was applied with a forward bias DC voltage under a nitrogen atmosphere to emit light.
• a luminance force S of 1000 cd / m 2 was obtained at ⁇ 8 V.
• This embodiment, of the styryl compound of the general formula [I], a styryl compound having the following structural formula (1 7) one 44, a mixed layer of A 1 Q 3 of the structural formula electrostatic This is an example of fabricating a bottom-emitting organic electroluminescent device of a zigzag type by using it as an electron transporting light emitting layer.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method: The organic electroluminescent device of Example 47 fabricated in this manner was subjected to a forward bias DC voltage in a nitrogen atmosphere to emit light. Was evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 655 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 110 cd / m 2 was obtained at 8 V.
• Structural formula (1 7)-45 An organic electroluminescent device was manufactured in accordance with Example 2 in both the layer structure and the film forming method. The organic electroluminescent device of Example 48 thus manufactured was applied with a forward bias DC voltage under a nitrogen atmosphere to improve the light emitting characteristics. evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 642 nm. Voltage-brightness measurement showed a luminance of 350 cdZm 2 at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 49 manufactured in this manner was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 64 nm. Voltage-brightness measurement showed a luminance of 250 cd / m 2 at 8 V.
• this organic electroluminescent device After the fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, and no deterioration of the fe: device was observed. In addition, when the current value was kept constant at an initial luminance of 300 cd / m 2 to continuously emit light and was forcibly degraded, it took 180 hours until the luminance was reduced to half.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 50 fabricated in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 65 nm. In addition, when voltage-brightness measurement was performed, a luminance of 280 cd / m 2 was obtained at 8 V. After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. In addition, when a constant current value was applied at an initial luminance of 300 cd dZm 2 to continuously emit light, and the light was forcibly deteriorated, it took 240 hours until the luminance was reduced to half.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device thus manufactured was applied to the organic electroluminescent device of Example 51 by applying a forward bias DC voltage under a nitrogen atmosphere.
• a forward bias DC voltage under a nitrogen atmosphere.
• It emitted a red light which was found by spectrometry (as in Example 1) to have a peak at about 635 nm.
• a luminance of 350 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.
• the luminescent characteristics were obtained by applying a forward bias DC voltage to the organic electroluminescent device thus fabricated in Example 52 under a nitrogen atmosphere.
• the luminescent color was red, and the spectrum was measured in the same manner as in Example 1.
• a spectrum having a luminescent peak at around 640 nm was obtained.
• a luminance of 300 cd / m 2 was obtained.
• the organic electroluminescent device of Example 5 3 with film forming method in conformity with Example 2 was produced as the t fabricated organic electroluminescent device, light emission by applying a forward bias DC voltage in a nitrogen atmosphere The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 600 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 400 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was produced according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 54 produced in this manner was placed under a nitrogen atmosphere. Then, a forward bias DC voltage was applied to evaluate the light emission characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 645 nm. In addition, when the pressure and the brightness were measured, a brightness of 5200 cd Zm 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 55 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light.
• the properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 647 nm.
• spectrometry as in Example 1
• a luminance of 500 cd / m 2 was obtained at ⁇ 8 V.
• An organic electroluminescent device was fabricated in accordance with Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 56 fabricated in this manner was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light.
• the emission color was red, and a spectrum having a light emission peak at about 633 nm was obtained as a result of spectral measurement in the same manner as in Example 1.
• Voltage-brightness measurement was also performed. However, a luminance of 220 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method.c
• the organic electroluminescent device of Example 57 fabricated in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 595 nm. Voltage-brightness measurement showed a luminance of 380 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 58 fabricated in this way was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 590 nm. Voltage-brightness measurement showed that a luminance of 320 cd / m 2 was obtained at 8 V.
• Structural formula (17) — 56 An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method: The organic electroluminescent device of Example 59 thus manufactured was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. The luminescent color was orange, and the spectral measurement was performed in the same manner as in Example 1. As a result, the luminescent color was around 588 nm.
• this organic electroluminescent device After manufacturing this organic electroluminescent device, it was left under a nitrogen atmosphere for one month. No element deterioration was observed. In addition, when the current was constantly supplied at an initial luminance of 300 cd dZm 2 to continuously emit light, and forcedly degraded, it took 150 hours until the luminance was reduced by half.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 60 thus manufactured was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. It emitted an orange light, which was found by spectrometry in the same manner as in Example 1 to yield a spectrum having an emission peak near 605 nm. Voltage-brightness measurement showed a luminance of 100 cd / m 2 at 8 V.
• the organic electroluminescent element of the film formation method with Example 2 t produced an organic electroluminescent device in conformity with Example 6 1 produced in this manner, light emission by applying a forward bias DC voltage in a nitrogen atmosphere The properties were evaluated. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 600 nm. The voltage - was subjected to luminance measurement, 1 9 5 0 luminance of c DZM 2 was obtained by 8V.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.c
• the organic electroluminescent device of Example 62 fabricated in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 670 nm. In addition, when voltage-luminance measurement was performed, a luminance of 290 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 with respect to both the layer structure and the film forming method. ⁇ The organic electroluminescent device of Example 63 fabricated in this manner was placed under a nitrogen atmosphere. Then, a forward bias DC voltage was applied to evaluate the light emission characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 625 nm. Voltage-brightness measurement showed a luminance of 620 cd / m 2 at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.
• the luminescent characteristics were obtained by applying a forward bias DC voltage to the organic electroluminescent device thus fabricated in Example 64 under a nitrogen atmosphere.
• the luminescent color was red, and a spectrum having a luminescent peak at about 635 nm was obtained as a result of spectral measurement in the same manner as in Example 1.
• Voltage-luminance measurement was performed. At 8 V, a luminance of 1260 cd / m 2 was obtained.
• Example 6 5 the organic electroluminescent element of the film formation method with Example 2 in compliance with the organic electroluminescent device was prepared t Example 6 5 produced in this manner, light emission by applying a forward bias DC voltage in a nitrogen atmosphere The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 645 nm. In addition, a voltage-luminance measurement showed a luminance of 950 cd Zm 2 at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 66 thus manufactured was applied with a forward bias DC voltage under a nitrogen atmosphere to emit light.
• Voltage-brightness measurement showed a luminance of 550 cd / m 2 at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.
• the luminescent characteristics were obtained by applying a forward bias DC voltage to the organic electroluminescent device thus fabricated in Example 67 under a nitrogen atmosphere.
• the emission color was orange, and the spectroscopic measurement was performed in the same manner as in Example 1.
• a spectrum having a light emission peak near 587 nm was obtained.
• a luminance of 360 cd / m 2 was obtained.
• a mixed layer of the styryl compound of the above structural formula (17) and the styryl compound of the above structural formula (17) -20 was used to form an electron-transporting layer.
• a bottom emission type organic electroluminescent device having a single hetero structure was used as a light emitting layer.
• a 30 mm x 30 mm glass substrate having an anode made of 100 nm thick ITO formed on one surface was set in a vacuum evaporation apparatus.
• a metal mask to have a plurality of 2. 0 mmx 2. unit openings 0mm arranged close to the substrate, under a vacuum of less than 10- 4 P a by vacuum evaporation of the structural formula ⁇ - NPD was formed into a film having a thickness of, for example, 50 nm.
• the deposition rate was 0.1 nm / sec.
• a layer in which the styryl compound of the above structural formula (17) -4 and the styryl compound of the above structural formula (17) -20 were mixed was deposited in contact with the hole transport layer.
• the thickness of the mixed layer of the styryl compound is, for example, 50 nm.
• a mixed film of Mg and Ag was adopted as the cathode material, and this was also formed by vapor deposition, for example, at a mixing ratio of Mg and Ag of 1: 3, and was formed to a thickness of 200 nm to produce an organic electroluminescent device.
• Example 6 9 The organic electroluminescent device of Example 68 fabricated in this manner was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to evaluate the light emitting characteristics.
• the emission spectrum varied depending on the mixing ratio of the two styryl compounds, and an arbitrary wavelength could be selected within the emission peak range of 600 nm to 680 nm. At this time, electrical characteristics such as voltage-current characteristics of the device were not significantly changed.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method (
• the present Example relates to a styryl compound represented by the above structural formula (17) -32 and an aryl moiety (X in the above general formula [I]) in the styryl compound represented by the above structural formula (17) -32.
• This is an example in which element characteristics of an organic electroluminescent device manufactured using a styryl compound A-1 having the following structural formula in which a predetermined substituent has been removed from Comparative Example 1 are compared.
• Element 1 (Example 35): ⁇ —NPD (50 nm) Z stylyl compound of structural formula (17) -32 + A 1 q 3 (50 nm) ZMg: Ag (200 nm)
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 71 thus manufactured was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere.
• the emission color was orange, and a spectrum having a light emission peak at about 595 nm was obtained as a result of spectral measurement in the same manner as in Example 1.
• a luminance of 150 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.
• the organic EL device of Example 72 fabricated in this manner was subjected to a forward bias DC voltage in a nitrogen atmosphere under a nitrogen atmosphere to emit light.
• spectrometry as in Example 1
• a luminance of 110 cd / m 2 was obtained at 8 V.
• a bottom emission type organic electroluminescent device having a double hetero structure was manufactured by using a laminated film of a mixed layer of a styryl compound of (17) -32 and A 1 d 3 of the above structural formula as a light emitting layer. is there.
• a Hiichi NPD of the above structural formula was applied to a thickness of, for example, 25 nm. Then, a film was formed. Further, a styryl compound of the above structural formula (17) -32 and ⁇ -NPD as a light emitting material were deposited in contact with the hole transport layer at a weight ratio of 1: 1. The thickness of the light emitting layer composed of a mixed layer of the styryl compound of the above structural formula (17) -32 and ⁇ -NPD is also, for example, 2 It was 5 nm.
• the thickness of the light emitting layer composed of a mixed layer of the styryl compound of the above structural formula (17) -32 and A 1 Q 3 was also set to, for example, 25 nm.
• a 1 qi 3 of the above structural formula was deposited as an electron transporting material in contact with the light emitting layer.
• the film thickness of A 1 d 3 was , for example, 25 nm.
• a mixed film of Mg and Ag was adopted, and this was also formed by vapor deposition, for example, with a mixing ratio of Mg: Ag of 1: 3 to a thickness of 200 nm to produce an organic electroluminescent device. .
• a light emitting characteristic was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to the organic electroluminescent device of Example 73 manufactured as described above. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at 640 nm. Further, a voltage-brightness measurement was performed, and a luminance of 900 cdZm 2 was obtained at 8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. Further, when the forced deterioration continuous emission to by applying a constant current thereto with an initial luminance 3 00 c DZM 2, the luminance was 3 9 0 0 hour half until.
• one NPD of the above structural formula is for example 30 nm thick was formed.
• the styryl compound of the above structural formula (17) -32 and A 1 Q 3 and a-NPD were deposited in contact with the hole transport layer at a weight ratio of 2: 1: 1.
• the structural formula (1 7) - 3 was 2 styryl compound and A 1 q 3 and Q thickness also for instance 30 nm light-emitting layer composed of a mixed layer of NPD!.
• a 1 q 3 of the above structural formula was deposited in contact with the A 1 q 3 of the above structural formula to a light-emitting layer as an electron transporting material.
• the thickness of A 1 q 3 was , for example, 30 nm.
• a mixed film of Mg and Ag was used as the cathode material, and this was also formed by vapor deposition, for example, with a mixing ratio of Mg and Ag of 1: 3 to a thickness of 200 nm to fabricate an organic electroluminescent device.
• a light emitting characteristic was evaluated by applying a forward bias DC voltage to the organic electroluminescent device of Example 74 thus manufactured in a nitrogen atmosphere. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at 640 nm. In addition, when voltage-brightness measurement was performed, a luminance of 1000 cdZm 2 was obtained at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.
• the luminescent characteristics were obtained by applying a forward bias DC voltage to the organic electroluminescent device thus fabricated in Example 75 under a nitrogen atmosphere.
• the emission color was orange, and the spectroscopic measurement was performed in the same manner as in Example 1.
• a spectrum having a light emission peak at around 605 nm was obtained.
• a luminance of 900 cd / m 2 was obtained.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 76 fabricated in this manner was placed under a nitrogen atmosphere. Then, a forward bias DC voltage was applied to evaluate the light emission characteristics. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 600 nm. Voltage-brightness measurement showed a luminance of 1700 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film formation method.
• the organic electroluminescent device of Example 77 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light. The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 670 nm. Voltage-brightness measurement showed a luminance of 280 cd / m 2 at 8 V.
• a bottom emission type organic electroluminescent device having a single hetero structure was manufactured.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 78 manufactured in this manner was illuminated by applying a forward bias DC voltage under a nitrogen atmosphere. The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 625 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 630 cd / m 2 was obtained at .8 V.
• Embodiment or, among the styryl compound of the general formula [I], the following structural formula (1 7) - 77 and styryl compound of the mixed layer electron transport light-emitting layer between A 1 q 3 of the structural formula Used, single-hetero structure bottom emission organic This is an example of manufacturing a field emission device.
• the organic electroluminescent element of the film formation method with Example 2 Example was prepared as the c fabricated organic electroluminescent device compliant 7 9, light emission by applying a forward bias DC voltage in a nitrogen atmosphere The properties were evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 635 nm. Further, When a voltage was one luminance measurement, 1 22 0 luminance of c DZM 2 was obtained in 8 V.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• a light emitting characteristic was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to the organic electroluminescent device of Example 80 thus manufactured. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 645 nm.
• spectrometry as in Example 1
• a luminance of 100 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured according to Example 2 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 81 thus manufactured was applied with a forward bias DC voltage in a nitrogen atmosphere to emit light.
• the properties were evaluated. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 60 nm.
• a luminance of 950 cd / m 1 was obtained at 8 V when voltage-luminance measurement was performed.
• the device was left under a nitrogen atmosphere for one month, but no device degradation was observed.
• a constant current value was applied at an initial luminance of 300 cd / m 2 to continuously emit light, and the light was forcibly deteriorated, it took 750 hours until the luminance was reduced to half.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method: A forward bias DC voltage was applied to the organic electroluminescent device of Example 82 manufactured in Example 2 under a nitrogen atmosphere. To evaluate the light emission characteristics. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 610 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 2000 cd / m 2 was obtained at 8 V.
• the organic electroluminescent device of Example 83 with the film formation method in conformity with Example 2 was produced as the c fabricated organic electroluminescent device, the light emitting characteristics by applying a forward bias DC voltage in a nitrogen atmosphere was evaluated. It emitted an orange light, which was found by spectrometry (as in Example 1) to have a peak at about 595 nm. In addition, when voltage-luminance measurement was performed, a luminance of 1400 cdZm 2 was obtained at 8 V.
• Structural formula (1 7)-84 Layer structure, the organic electroluminescent device of Example 84 in which both film forming method in conformity with Example 2 was prepared like this t fabricated organic electroluminescent device, the light emitting characteristics by applying a forward bias DC voltage in a nitrogen atmosphere was evaluated. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 690 nm. Voltage-brightness measurement showed a luminance of 170 cd / m 2 at 8 V.
• An organic electroluminescent device was fabricated according to Example 2 in both the layer structure and the film forming method. ⁇ The organic electroluminescent device of Example 85 fabricated in this manner was placed under a nitrogen atmosphere. Then, a forward bias DC voltage was applied to evaluate the light emission characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 640 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 110 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 2 for both the layer structure and the film forming method.
• the organic electroluminescent device of Example 86 thus manufactured was applied with a forward bias DC voltage under a nitrogen atmosphere to emit light.
• a voltage-luminance measurement showed that a luminance of 900 cd / m 2 was obtained at ⁇ 8 V.
• This comparative example is the structural formula (1 7) - and device using a 8 mixture layer styryl compound and an A 1 d 3 of the above structural formula as the electron transport light-emitting layer
• the structural formula (1 7) - 8 is an example in which device characteristics of a device using a single film of only the styryl compound of No. 8 as an electron transporting light emitting layer are compared.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• Element 4 (Comparative Example 1): ITO / CK—NPD (50 nm) Compound (17) —8 (50 nm) / Mg: Ag (200 nm)
• the emission colors of the element 3 and the element 4 were both orange, and the same spectrum having a light emission peak at about 60 nm was obtained as a result of the same spectral measurement as in Example 1.
• This comparative example is the structural formula (1-7) - 1 4 styryl compound and device using a mixed layer of an A 1 q 3 of the structural formula as an electron transport luminescent layer, the above Symbol structural formula (1 7)
• This is an example comparing the device characteristics of devices using a single film of only the styryl compound of 14 as the electron-transporting light-emitting layer.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• Element 5 (Example 1 7): I TO / ⁇ -NPD (5 0 nm) / formula (1 7) - 14 styryl compound + A 1 q 3 (5 0 nm) ZMg: A g (2 0 0 nm)
• Element 6 (Comparative Example 2): I ⁇ / ⁇ -NPD (50 nm) Z styryl compound of structural formula (17) -14 (50 nm) ZMg: Ag (200 nm) Element 5 and element 6 The emission color of each was orange, and the same spectrum having a light emission peak near 605 nm was obtained as a result of spectroscopic measurement in the same manner as in Example 1.
• This comparative example is based on a device using a mixed layer of the styryl compound of the above structural formula (17) —20 and A 1 Q 3 of the above structural formula as an electron transporting light emitting layer. 7) This is an example comparing the device characteristics of devices using a single film of only styryl compound of No. 20 as the electron transporting light emitting layer.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• Element 7 (Example 23): I TO / a -NPD (50 nm) Z stylyl compound of structural formula (17)-20 + A 1 q 3 (50 nm) / Mg: Ag (200) nm)
• Element 8 (Comparative Example 3): I ⁇ / ⁇ -NPD (50 nm) Z structural formula (17) -styryl compound of 20 (50 nm) ZMg: Ag (200 nm)
• the emission colors of the device 7 and the device 8 were both red.
• a similar spectrum having a light emission peak near 680 nm was obtained.
• This comparative example is the structural formula (1 7) - and device using a 26 mixed layer of styryl compound and the structural formula A 1 q 3 as an electron transporting and light emitting layer, the structural formula (1 7) -
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• Element 9 (Example 2 9): I TO / ⁇ -NPD (5 0 nm) / formula (1 7) Single 2 6 styryl compound + A 1 q 3 (5 0 nm) ZMg: A g (20 0 nm)
• Element 10 (Comparative Example 4): I ⁇ / ⁇ -NPD (50 nm) No styryl compound of structural formula (17) -26 (50 nm) ZMg: Ag (200 ⁇ m)
• the emission colors of the element 9 and the element 10 were both red, and the same spectrum having a light emission peak at about 630 nm was obtained as a result of spectral measurement in the same manner as in Example 1.
• This comparative example includes a device using a mixed layer of the styryl compound of the above structural formula (17) _32 and A 1 Q 3 of the above structural formula as an electron-transporting light emitting layer; 7) This is an example comparing the device characteristics of devices using a single film of only the styryl compound of No. 32 as the electron transporting light emitting layer.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• Element 1 1 (Example 3 5): I TO / a -NPD (50 nm) Z Formula (1 7) - 3 2 styryl compound + A lq 3 (5 0 nm ) Mg: Ag (200 nm)
• Element 12 (Comparative Example 5): ITO / ⁇ -NPD (50 nm) / styryl compound of structural formula (17) -32 (50 nm) ZMg: Ag (200 ⁇ m)
• the emission colors of the element 11 and the element 12 were both red, and the same spectrum having a light emission peak at around 640 nm was obtained as a result of spectroscopic measurement in the same manner as in Example 1.
• an element using a mixed layer of the styryl compound of the above structural formula (17) — 42 and the above structural formula A 1 Q 3 as an electron transporting light-emitting layer, and a device of the above structural formula (17) — 42 is an example in which device characteristics of a device using a single film of only a styryl compound as an electron-transporting light-emitting layer were compared.
• An organic electroluminescent device was fabricated according to Example 2 for both the layer structure and the film forming method.
• Element 13 (Example 45): I TOXa -NPD (50 nm) / Structural formula (17) A styryl compound of 42 + A 1 q 3 (50 nm) / Mg: Ag (2 O 0 nm)
• Element 14 (Comparative Example 6): I TOZo! — NPD (50 nm) Z structural formula (17) One-42 styryl compound (50 nm) / Mg: Ag (200 ⁇ m)
• the emission colors of the elements 13 and 14 were both red. As a result of the spectroscopic measurement in the same manner as in Example 1, a similar spectrum having an emission peak near 65500 nm was obtained.
• This comparative example is the structural formula (1 7) - and element using 5 1 of styryl compound and mixed layer of A ld 3 of the structural formula as an electron transport luminescent layer, the above Symbol structural formula (1 7 This is an example comparing the device characteristics of a device using a single film of only the styryl compound of 51 as the electron transporting light emitting layer.
• An organic electroluminescent device was manufactured according to Example 2 for both the layer structure and the film forming method.
• Element 1 5 (Example 54): I TO / a- NPD (5 0 nm) / formula (1 7) one 5 1 styryl compound + A 1 q 3 (5 0 nm) / Mg: A g (2 (O 0 nm)
• Element 16 (Comparative Example 7): I TOZa— NPD (50 nm) / Structural formula (17)-51 styryl compound (50 nm) / Mg: Ag (200 nm)
• the emission colors of the element 15 and the element 16 were both red. As a result of the spectroscopic measurement in the same manner as in Example 1, a similar spectrum having an emission peak near 645 nm was obtained.
• This comparative example is based on a device using a mixed layer of the styryl compound of the above structural formula (17) -55 and A 1 Q 3 of the above structural formula as an electron transporting light emitting layer. 7) -55 This is an example in which the device characteristics of a device using a single film of only the styryl compound as the electron transporting light emitting layer were compared.
• Element 17 (Example 58): I TO / a -NPD (50 nm) / Structural formula (17) —styryl compound of 55 + A 1 q 3 (50 nm) / Mg: Ag ( 200 nm)
• the emission color of each of the device 17 and the device 18 was orange, and the same spectrum having a light emission peak at around 590 nm was obtained as a result of spectroscopic measurement in the same manner as in Example 1.
• an anode consisting of a 100-nm-thick silver alloy and a 100-nm-thick ITO formed on the silver alloy was formed on one surface in a vacuum evaporation apparatus.
• An mm ⁇ 30 mm glass substrate was set.
• deposition mask a plurality of 2. 0 mmX 2. 0 to mm metal mask having a unit openings was placed close to the substrate, the following structural formula under 1 0- 4 P a following vacuum by a vacuum deposition method
• the 2-TNATA film was formed to a thickness of, for example, 20 nm, and then the NPD was formed thereon to a thickness of, for example, 43 nm.
• the deposition rates were each 0.1 nm / sec.
• Aminostyryl compound of the above structural formula (17) — 32 and A 1 q 3 The film thickness of the electron transport layer (also serving as the light emitting layer) was, for example, 30 nm, and the deposition rate was 0.2 nmZ seconds each.
• a mixed film of Mg and Ag is adopted, and this is also formed by vapor deposition to a thickness of 12 nm with a mixing ratio of Mg and Ag of 5: 1, for example, as shown in FIG.
• An organic electroluminescent device was manufactured.
• a light emitting characteristic was evaluated by applying a forward bias DC voltage to the organic electroluminescent device of Example 87 thus manufactured in a nitrogen atmosphere. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 640 nm. Voltage-brightness measurement showed a luminance of 850 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• a light emitting characteristic was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to the organic electroluminescent device of Example 88 thus manufactured. It emitted red light. By spectral analysis in the same way as in Example 1, the emitted light was near 640 nm. A spectrum was obtained with the Also, when voltage-brightness measurement was performed,
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• Example 89 To the organic electroluminescent device of Example 89 manufactured in this way, a forward bias DC voltage was applied in a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 643 nm. In addition, when a voltage-brightness measurement was performed, a luminance of 800 cd Zm 2 was obtained at 8 V.
• this organic electroluminescent device was fabricated, it was left under a nitrogen atmosphere for one month, but no device degradation was observed. Further, by passing current value at an initial luminance 3 0 0 cd Zm 2 constant continuous light emission, when it is forced degradation, the luminance was 6 0 0 0 hour half until.
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 90 thus produced was evaluated for luminous characteristics by applying a forward bias DC voltage under a nitrogen atmosphere. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 64 nm. Further, a voltage-brightness measurement was carried out, and as a result, a luminance of 650 cd Zm 2 was obtained at 8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. In addition, a constant current value was applied at an initial luminance of 300 cd Zm 2 to continuously emit light. When the luminance was forcibly deteriorated, it took 220 hours until the luminance was reduced by half.
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• a light emitting characteristic was evaluated by applying a forward bias DC voltage to the organic electroluminescent device of Example 91 thus manufactured in a nitrogen atmosphere. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 642 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 680 cd / m 2 was obtained at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• Example 92 The organic electroluminescent device of Example 92 fabricated in this way was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to evaluate the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 645 nm. Voltage-brightness measurement showed a luminance of 660 cd / m 2 at 8 V.
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method. .
• Example 93 The organic electroluminescent device of Example 93 fabricated in this manner was placed under a nitrogen atmosphere. Then, a forward bias DC voltage was applied to evaluate the light emission characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 600 nm. In addition, when voltage-luminance measurement was performed, luminance of 700 cd / m 2 was obtained at 8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. Further, by passing current value at an initial luminance 3 0 0 cd Zm 2 constant continuous light emission, when it is forced degradation, the luminance was 3 3 0 0 hour half until.
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• a light emitting characteristic was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to the organic electroluminescent device of Example 94 manufactured as described above. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 64 nm. In addition, when voltage-brightness measurement was performed, a luminance of 110 cd / m 2 was obtained at 8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. Further, by passing current value at an initial luminance 3 0 0 cd Zm 2 constant continuous light emission, when it is forced degradation, the luminance was 6 0 0 0 hour half until.
• This example shows that, among the styryl compounds of the general formula [I], the above structural formula (1) 7)
• a mixed layer of a styryl compound of No. 20 and A 1 Q 3 of the above structural formula was used as an electron transporting light emitting layer to produce a top emission type organic electroluminescent element.
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 95 manufactured in this manner was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 655 nm. In addition, when voltage-brightness measurement was performed, a luminance of 200 cd Zm 2 was obtained at 8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. In addition, continuous light emission was performed at a constant current value of 300 cd / m 2 at an initial luminance of 500 cd / m 2 , and it took 500 hours for the luminance to be reduced to half when forcedly deteriorated.
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• Example 96 The organic electroluminescent device of Example 96 fabricated as described above was evaluated by applying a forward bias DC voltage under a nitrogen atmosphere to the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 655 nm. Also, when the voltage-brightness measurement was performed,
• An organic electroluminescent device was manufactured in accordance with Example 87 in both the layer structure and the film forming method.
• the organic electroluminescent device of Example 97 manufactured in this manner was evaluated by applying a forward bias DC voltage in a nitrogen atmosphere to the light emitting characteristics. It emitted a red light, which was found by spectrometry (as in Example 1) to have a peak at about 63 nm. In addition, when the voltage-brightness measurement was performed, a luminance of 180 cd / m 2 was obtained at 8 V.
• this organic electroluminescent device After fabrication of this organic electroluminescent device, the device was left under a nitrogen atmosphere for one month, but no device degradation was observed. In addition, continuous light emission was performed with a constant current value at an initial luminance of 300 cd Zm 2 , and when forcedly deteriorated, it took 250 hours until the luminance was reduced by half.
• an organic electroluminescent element and the light emitting device of the present invention in an organic electroluminescent element in which an organic layer having a light emitting region is provided between an anode and a cathode, at least one of the constituent layers of the organic layer is Since it is composed of a mixed layer containing at least one styryl compound represented by the general formula [I] and a material having a charge transporting ability, it has high luminance, high reliability and good thermal stability. It is possible to arbitrarily select the emission color of a relatively long wavelength such as red, and the color purity is good.
• An organic electroluminescent device can be provided.

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