Anthracene Compounds

Abstract

To provide a compound for a novel host material, or to improve the lifetime of a light-emitting device To provide a compound for a host material that can achieve the above, or to provide a light-emitting device with a long life. Alternatively, materials with high thermal properties such as glass transition points can be provided. The present invention provides an anthracene compound for a host, represented by the following general formula (G1): JPEG2026042816000045.jpg41167 (However, in the above general formula (G1), R1 to R7 are each independently hydrogen or carbon. represents an aryl group having a prime number of 1 to 25.

Description

[Technical Field]

[0001] One aspect of the present invention is an anthracene compound for a host material, a light-emitting element, a light-emitting device, a display Related to play modules, lighting modules, display devices, light-emitting devices, electronic devices and lighting devices Note that one embodiment of the present invention is not limited to the above technical fields. The technical field of one aspect of the present invention relates to an article, a method, or a manufacturing method. One aspect of the invention is a process, machine, manufacture, or composition of matter. Therefore, the present invention more specifically relates to the The technical field of one embodiment of the present invention is a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, a lighting device, a Lighting device, power storage device, storage device, imaging device, driving method thereof, or manufacturing method thereof can be cited as an example. [Background technology]

[0002] Electroluminescence (EL) using organic compounds Light-emitting devices (organic EL elements) that utilize these luminescence are being put to practical use. The basic structure of the device is a pair of electrodes sandwiching an organic compound layer (EL layer) containing a light-emitting material. When a voltage is applied to this element, carriers are injected and the recombination of these carriers occurs. By utilizing the energy, light can be emitted from the light-emitting material.

[0003] These light-emitting devices are self-luminous, so they have higher visibility than LCD displays. The light-emitting device is suitable for use as a pixel in a display. Another major advantage of the LCD is that it does not require a backlight and can be made thin and lightweight. Another feature is its extremely fast response time.

[0004] In addition, these light-emitting devices can be fabricated with a continuous two-dimensional light-emitting layer. This is a point light source, such as an incandescent bulb or LED, and This is a feature that is difficult to obtain with linear light sources such as fluorescent lamps, so it is used as a surface light source that can be applied to lighting, etc. It is also highly useful as a tool.

[0005] Displays and lighting devices using such light-emitting devices are suitable for use in a variety of electronic devices. However, research and development is being conducted to find light-emitting devices with better efficiency and life span. There are.

[0006] The properties of light-emitting devices have improved dramatically, but many other properties, including efficiency and durability, remain. It must be said that the technology is still insufficient to meet the high demands of EL. To solve the problem of burn-in, which is still cited as a problem, it is necessary to reduce the decrease in efficiency due to deterioration. The smaller the bottom, the better.

[0007] Deterioration is largely dependent on the luminescent center material and its surrounding materials, so it is difficult to determine good characteristics. The development of host materials with such properties has been actively pursued. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent Application Laid-Open No. 2004-59535 Summary of the Invention [Problem to be solved by the invention]

[0009] Therefore, one aspect of the present invention aims to provide a novel compound for use as a host material. In another aspect of the present invention, a host material capable of improving the lifetime of a light-emitting device is provided. Another object of the present invention is to provide a compound having a long life. Another object of the present invention is to provide a device that can be used in a wide range of applications, including a device that can be used in a wide range of applications. The object is to provide a material with high physical properties.

[0010] In another embodiment of the present invention, a light-emitting device, an electronic device, and a display device each having high reliability are provided. The purpose is to provide.

[0011] The present invention is intended to solve any one of the above problems. [Means for solving the problem]

[0012] One embodiment of the present invention is an anthracene compound for a host represented by the following general formula (G1).

[0013] [ka]

[0014] However, in general formula (G1), R 1 ~R 7 are each independently hydrogen or a group having one carbon atom. represents an aryl group having a substituent of 1 to 25;

[0015] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device according to the above-described embodiment, wherein R 1 ~R 7 1 of which has 1 or more carbon atoms The anthracene compound for host is an anthracene compound in which each of the aryl groups is 2 to 25, and the remaining groups are hydrogen atoms.

[0016] Alternatively, another embodiment of the present invention is an anthracene compound for a host material represented by the following general formula (G2): It is a compound.

[0017] [ka]

[0018] However, in the above general formula (G2), R 4 is hydrogen or an aryl having 1 to 25 carbon atoms Represents a group.

[0019] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the aryl group having 1 to 25 carbon atoms is a phenyl group.

[0020] Another embodiment of the present invention is an anthracene compound for a host represented by the following structural formula (100): It is a compound.

[0021] [ka]

[0022] Alternatively, another aspect of the present invention is a light-emitting diode (LED) comprising an anode, a cathode, and an EL element located between the anode and the cathode. the EL layer has a luminescent center substance and a host material, and the host material is The anthracene compound for host material has the above-described structure.

[0023] Alternatively, in another aspect of the present invention, in the above-described structure, the luminescent center substance emits blue fluorescence. It is a light-emitting device.

[0024] Another embodiment of the present invention is a light-emitting device having any of the above structures, a transistor, or and a substrate.

[0025] Another embodiment of the present invention is a light-emitting device having the above structure, a sensor, an operation button, a switch, and a light-emitting element. An electronic device that has a speaker or microphone.

[0026] Another embodiment of the present invention is a lighting device including a light-emitting device having the above structure and a housing. is.

[0027] In this specification, the term "light-emitting device" includes an image display device using a light-emitting device. In addition, a connector such as anisotropic conductive film or TCP (Tape) is attached to the light-emitting device. Module with Carrier Package attached, printed on TCP Modules with wiring boards or light-emitting devices with COG (Chip On Glass) s) method, a module in which an IC (integrated circuit) is directly mounted may also be included in the category of light-emitting device. Furthermore, lighting fixtures and the like may include a light-emitting device. [Effects of the Invention]

[0028] According to one embodiment of the present invention, a novel organic compound having a hole-transporting property can be provided. Alternatively, a novel hole transport material can be provided. Alternatively, a novel light-emitting device can be provided. Alternatively, a light-emitting device with a long life can be provided. It is possible to provide an optical device or a light-emitting device with good light-emitting efficiency. Alternatively, a light-emitting device with a low driving voltage can be provided. It is possible to provide an element in which the voltage change due to the accumulation of driving time is small.

[0029] In another embodiment of the present invention, a light-emitting device, an electronic device, and a display device each having high reliability are provided. In another embodiment of the present invention, a light-emitting device with low power consumption can be provided. An electronic device and a display device can each be provided.

[0030] The description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. , the specification, drawings, claims, etc., and It is possible to extract other effects from the claims and other descriptions. [Brief explanation of the drawings]

[0031] [Figure 1] 1A1, 1A2, 1B and 1C are schematic diagrams of light emitting devices. [Figure 2] 2A and 2B are conceptual diagrams of an active matrix light emitting device. [Figure 3] 3A and 3B are conceptual diagrams of an active matrix light emitting device. [Figure 4] FIG. 4 is a conceptual diagram of an active matrix light emitting device. [Figure 5] 5A and 5B are conceptual diagrams of a passive matrix light emitting device. [Figure 6] 6A and 6B are diagrams showing a lighting device. [Figure 7] 7A, 7B1, 7B2, and 7C are diagrams showing electronic devices. [Figure 8] 8A, 8B, and 8C are diagrams showing electronic devices. [Figure 9] FIG. 9 is a diagram showing a lighting device. [Figure 10] FIG. 10 is a diagram showing a lighting device. [Figure 11] FIG. 11 is a diagram showing an in-vehicle display device and a lighting device. [Figure 12] 12A and 12B are diagrams showing electronic devices. [Figure 13] 13A, 13B, and 13C are diagrams showing electronic devices. [Figure 14] Figures 14A and 14B are 1H-NMR charts of 2αN-αNPhA. [Figure 15] FIG. 15 shows the absorption and emission spectra of a toluene solution of 2αN-αNPhA. [Figure 16] Figure 16 shows the absorption and emission spectra of a thin film of 2αN-αNPhA. [Figure 17] Figures 17A and 17B are 1H-NMR charts of 2PαN-αNPhA. [Figure 18] FIG. 18 shows the absorption and emission spectra of a toluene solution of 2PαN-αNPhA. [Figure 19] Figure 19 shows the absorption and emission spectra of a thin film of 2PαN-αNPhA. [Figure 20] FIG. 20 shows the luminance-current density characteristics of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2. [Figure 21] FIG. 21 shows the current efficiency-luminance characteristics of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2. [Figure 22] FIG. 22 shows the luminance-voltage characteristics of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2. [Figure 23] FIG. 23 shows the current-voltage characteristics of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2. [Figure 24] FIG. 24 shows the external quantum efficiency-luminance characteristics of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2. [Figure 25] FIG. 25 shows the emission spectra of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2. [Figure 26] FIG. 26 shows the normalized luminance vs. time change characteristics of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2. [Figure 27]FIG. 27 shows the luminance-current density characteristics of light-emitting device 2, comparative light-emitting device 3, and comparative light-emitting device 4. [Figure 28] FIG. 28 shows the current efficiency-luminance characteristics of light-emitting device 2, comparative light-emitting device 3, and comparative light-emitting device 4. [Figure 29] FIG. 29 shows the luminance-voltage characteristics of the light-emitting device 2, the comparative light-emitting device 3, and the comparative light-emitting device 4. [Figure 30] FIG. 30 shows the current-voltage characteristics of the light-emitting device 2, the comparative light-emitting device 3, and the comparative light-emitting device 4. [Figure 31] FIG. 31 shows the external quantum efficiency-luminance characteristics of the light-emitting device 2, the comparative light-emitting device 3, and the comparative light-emitting device 4. [Figure 32] FIG. 32 shows the emission spectra of light-emitting device 2, comparative light-emitting device 3, and comparative light-emitting device 4. [Figure 33] FIG. 33 shows the normalized luminance vs. time change characteristics of the light-emitting device 2, the comparative light-emitting device 3, and the comparative light-emitting device 4. [Figure 34] FIG. 34 shows the luminance-current density characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting devices 5 to 10. [Figure 35] FIG. 35 shows the current efficiency-luminance characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting devices 5 to 10. [Figure 36] FIG. 36 shows the luminance-voltage characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting devices 5 to 10. [Figure 37] FIG. 37 shows the current-voltage characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting devices 5 to 10. [Figure 38] FIG. 38 shows the external quantum efficiency-luminance characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting devices 5 to 10. [Figure 39] FIG. 39 shows the emission spectra of light-emitting device 3, light-emitting device 4, and comparative light-emitting devices 5 to 10. [Figure 40] FIG. 40 shows the luminance-current density characteristics of light-emitting device 5, comparative light-emitting device 11, and comparative light-emitting device 12. [Figure 41] FIG. 41 shows the current efficiency-luminance characteristics of the light-emitting device 5, the comparative light-emitting device 11, and the comparative light-emitting device 12. [Figure 42] FIG. 42 shows the luminance-voltage characteristics of light-emitting device 5, comparative light-emitting device 11, and comparative light-emitting device 12. [Figure 43] FIG. 43 shows the current-voltage characteristics of the light-emitting device 5, the comparative light-emitting device 11, and the comparative light-emitting device 12. [Figure 44] FIG. 44 shows the external quantum efficiency-luminance characteristics of the light-emitting device 5, the comparative light-emitting device 11, and the comparative light-emitting device 12. [Figure 45] FIG. 45 shows the emission spectra of light-emitting device 5, comparative light-emitting device 11, and comparative light-emitting device 12. [Figure 46] FIG. 46 shows the normalized luminance vs. time change characteristics of the light-emitting device 5, the comparative light-emitting device 11, and the comparative light-emitting device 12. DETAILED DESCRIPTION OF THE INVENTION

[0032] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details thereof may be changed without departing from the spirit and scope of the present invention. It will be readily apparent to those skilled in the art that various modifications may be made to the present invention. It should not be construed as being limited to the description of the embodiments.

[0033] (Embodiment 1) The anthracene compound for a host material according to one embodiment of the present invention is a compound represented by the following general formula (G1): It is a mechanical compound.

[0034] [ka]

[0035] However, in the above general formula (G1), R 1 ~R 7 are each independently hydrogen or a group having 6 carbon atoms It represents an aryl group having a molecular weight of 1 to 25.

[0036] Examples of the aryl group having 6 to 25 carbon atoms include an anthryl group, a phenanthryl group, and a pyrenyl group. , triphenylenyl group, fluoranthenyl group, biphenyl group, terphenyl group, quaternyl group Examples include a phenyl group.

[0037] R 1 ~R 7 are all hydrogen atoms, or one is an aryl group having 6 to 25 carbon atoms; Preferably, one is an aryl group having 6 to 25 carbon atoms and the remaining is hydrogen. is hydrogen, as shown in the following general formula (G2), R 4 is more preferably an aryl group. I wish.

[0038] [ka]

[0039] The anthracene compound for a host material according to one embodiment of the present invention having the above-described structure can be used as an organic compound. By using the compound as a host material in the light-emitting layer of a light-emitting device, It is possible to provide a light-emitting device.

[0040] A light-emitting device using the compound represented by the general formula (G1) as a host material is In the compound represented by the above general formula (G1), A compound having a substituent on either the naphthyl group or the phenyl group is used as a host material. The light emitting device can have a better life span than the light emitting device used.

[0041] Similarly, a light-emitting device using the compound represented by the above general formula (G1) as a host material The anthracene skeleton of the compound represented by the general formula (G1) is preferably at the 9-position and the 2-position. A compound in which an alkyl group or an alkylsilyl group is bonded to either of the naphthyl groups bonded to the and a light-emitting device having a longer life than a light-emitting device using the compound as a host material. In addition, the anthracene skeleton of the compound represented by the general formula (G1) can be A compound in which an aryl group having 6 to 25 carbon atoms is bonded to a naphthyl group bonded to the 2-position is used as a host material. The light emitting device used as the material can be a light emitting device with a good life span.

[0042] Specific examples of organic compounds having the above structure are shown below.

[0043] [ka]

[0044] [ka]

[0045] The organic compounds described above can be synthesized according to the following synthesis scheme.

[0046] The anthracene compound (G1) for a host material according to one embodiment of the present invention can be prepared by the following synthetic scheme: That is, it can be synthesized by using a halogen compound of an anthracene derivative or The compound (a1) having a triflate group and a boronic acid of a naphthalene compound or an organic boron compound are By coupling with the element compound (a2) by Suzuki-Miyaura reaction, one embodiment of the present invention can be obtained. The anthracene compound (G1) can be obtained.

[0047] [ka]

[0048] In the above synthesis scheme, R 1 ~R 7 each independently represents hydrogen or a group having 6 to 25 carbon atoms In addition, R 8 , R 9 are each independently hydrogen or the number of carbon atoms R represents any one of the alkyl groups of 1 to 6; 8 and R 9 are bonded to each other to form a ring It's okay to be there.

[0049] Furthermore, X represents a halogen or a triflate group, and when X is a halogen, it is particularly preferred that chlorine, bromine, Dysine and iodine are preferred.

[0050] Palladium catalysts that can be used in the reactions represented by the above synthesis scheme include: Palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), biphenyl triphenylphosphine)palladium(II) dichloride and the like.

[0051] The ligand for the palladium catalyst is di(1-adamantyl)-n-butylphosphine. , tri(ortho-tolyl)phosphine, triphenylphosphine, tricyclohexyl Examples thereof include arylphosphine.

[0052] The base that can be used in the reaction represented by the above synthesis scheme is sodium Organic bases such as tert-butoxide, and inorganic bases such as potassium carbonate and sodium carbonate Examples include:

[0053] In the reaction represented by the above synthesis scheme, a solvent that can be used is toluene. and water mixed solvents, alcohol and water mixed solvents such as toluene and ethanol, xylene and water mixed solvents Mixed solvents, mixed solvents of alcohols such as xylene and ethanol and water, mixed solvents of benzene and water solvent, a mixed solvent of alcohol such as benzene and ethanol and water, ethylene glycol dimethyl Mixtures of ethers such as ether and water, ethylene glycol dimethyl ether, etc. Examples include mixed solvents of esters and alcohols such as ethanol. The solvents that can be used are not limited to these. Also, toluene and water, or toluene and ethanol Mixtures of alcohol and water, and mixtures of ethers such as ethylene glycol dimethyl ether and water Solvents, ethers such as ethylene glycol dimethyl ether and alcohols such as ethanol A mixed solvent of the above is more preferred.

[0054] The coupling reaction that can be used in the above synthesis scheme is a reaction Instead of the Suzuki-Miyaura coupling reaction using organoboron compounds or boronic acids, Cross-coating using organoaluminum, organozirconium, organozinc, organotin compounds, etc. In addition, in the reaction shown in the above synthesis scheme, Organoboron compounds or boronic acids of benzene compounds and halides or trihalides of naphthalene compounds. The substituted riflate may be coupled via the Suzuki-Miyaura reaction.

[0055] The anthracene compound for host material according to one embodiment of the present invention can be synthesized as described above. be.

[0056] (Embodiment 2) FIG. 1A1 shows a diagram of a light-emitting device according to one embodiment of the present invention. The device has a first electrode 101, a second electrode 102, and an EL layer 103. The light-emitting layer 113 includes the host according to one embodiment of the present invention described in Embodiment 1. The material contains anthracene derivatives.

[0057] The EL layer 103 includes a light-emitting layer 113, a hole injection layer 111, a hole transport layer 112, an electron transport layer 113, and a hole transport layer 114. The layer 114 and the electron injection layer 115 may also be included. The hole transport layer 112 may have various layers such as a hole blocking layer and a charge generating layer. 1A2, the first hole transport layer 112-1, the second hole transport layer 112-2, etc. The second hole transport layer 112-2 may be formed by dividing it into two layers using different materials. also functions as an electron blocking layer.

[0058] The anthracene compound for host material is used as a host material contained in the light-emitting layer 113. The anthracene compound for a host material is used as a host material in the invention. The optical device may be a long-life light-emitting device.

[0059] The first electrode 101 is made of a metal, alloy, or conductive material having a large work function (specifically, 4.0 eV or more). It is preferable to form the film using a compound such as a carboxylic acid or a mixture thereof. For example, indium tin oxide (ITO), silicon Indium oxide-tin oxide and indium oxide-zinc oxide containing silicon or silicon oxide , indium oxide containing tungsten oxide and zinc oxide (IWZO), etc. These conductive metal oxide films are usually formed by sputtering, but they can also be formed by sol-gel deposition. It is also possible to fabricate it by applying a method such as a quartz crystal process. Zinc was produced using a target containing 1 to 20 wt% zinc oxide added to indium oxide. Also, tungsten oxide and zinc oxide are used. The indium oxide (IWZO) contains 0.5% tungsten oxide relative to the indium oxide. Sputtering was performed using a target containing 5-5 wt% of zinc oxide and 0.1-1 wt% of zinc oxide. It can also be formed by the method. In addition, gold (Au), platinum (Pt), nickel (Ni) , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Nitrides of metallic materials (e.g., titanium nitride), copper (Cu), palladium (Pd), or Graphene can also be used. By using it in the layer 103 that is in contact with the first electrode 101, the electric field can be controlled regardless of the work function. You will be able to select the pole material.

[0060] In this embodiment, the laminated structure of the EL layer 103 is a hole injection layer as shown in FIG. In addition to the injection layer 111, the hole transport layer 112, and the light emitting layer 113, an electron transport layer 114 and an electron injection layer 1B, a hole injection layer 111, a hole transport layer 112, and a layer 115. 2. Two types of structures having an electron transport layer 114 and a charge generation layer 116 in addition to the light emitting layer 113. The materials constituting each layer are specifically shown below.

[0061] The hole injection layer 111 is a layer containing a substance having acceptor properties. The substance can be a compound having an electron-withdrawing group (halogen group or cyano group). , 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation :F4-TCNQ), 3,6-difluoro-2,5,7,7,8,8-hexacyanoquino Dimethane, chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8, 9,12-Hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8 -Hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ) Compounds having electron-withdrawing groups can be used. In the case of HAT-CN, an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms. Compounds containing an electron-withdrawing group (especially a halogen group such as a fluoro group) are preferred because they are thermally stable. Radialene derivatives containing halogen or cyano groups have very high electron-accepting properties. Preferred is α,α',α''-1,2,3-cyclopropanetriylidenetri S[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α' ,α''-1,2,3-Cyclopropanetriylidenetris[2,6-dichloro-3,5 -difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α' '-1,2,3-Cyclopropanetriylidenetris[2,3,4,5,6-pentafluoro Examples of substances with acceptor properties include: In addition to the organic compounds mentioned above, molybdenum oxide, vanadium oxide, and ruthenium oxide are also Other examples include phthalocyanines, tungsten oxides, manganese oxides, etc. Complexation of phthalocyanines such as phthalocyanine (abbreviated as HPc) and copper phthalocyanine (CuPc) Compound, 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino] Biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)a amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diazo Aromatic amine compounds such as poly(3,4-ethylenediamine) (abbreviation: DNTPD) or poly(3,4-ethylenediamine) Polymers such as poly(hydroxythiophene) / poly(styrene sulfonate) (PEDOT / PSS) This also allows the formation of the hole injection layer 111. By applying an electric field, electrons can be extracted from the hole transport layer (or hole transport material) that can.

[0062] In addition, the hole-injecting layer 111 may be formed by adding an acceptor substance to a substance having a hole-transporting property. A composite material containing an acceptor substance can also be used. By using a composite material with this structure, it is possible to select a material for forming the electrode regardless of the work function. That is, the first electrode 101 can be made of not only a material with a large work function but also a material with a small work function. As the acceptor material, the above-mentioned acceptor It is possible to use materials with ceptor properties, but among them, molybdenum oxide is It is preferred because it is stable, has low hygroscopicity, and is easy to handle.

[0063] As hole transporting substances used in the composite material, aromatic amine compounds and carbazole derivatives are , aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.), etc. The following organic compounds can be used as hole transporting substances for the composite material: , 1×10 -6 cm 2It is preferable that the substance has a hole mobility of .gtoreq. / Vs. The organic compound of one embodiment of the present invention can also be suitably used. Specific examples of organic compounds that can be used as the hole transporting substance are listed below.

[0064] Aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl) )-N,N'-diphenyl-p-phenylenediamine (DTDPPA), 4,4' -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation Name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl }-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl Carbazole derivatives Specific examples of the compound include 3-[N-(9-phenylcarbazol-3-yl)-N-phenyl]carbazol-3-yl ... Nylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N -(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol PCzPCA2 (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenyl Carbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1 ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tri bis[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(1 0-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenyl Benzene and the like can be used. As the aromatic hydrocarbon, for example, 2-tert-butyl ether can be used. t-BuDNA, 2-te rt-Butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5- Diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,1 0-Bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10- Di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth ), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), 2 -tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl -9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,10' -Diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl) -9,9'-bianthryl, 10,10'-bis[(2,3,4,5,6-pentapheny [phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, peri and 2,5,8,11-tetra(tert-butyl)perylene. In addition, pentacene, coronene, etc. may also be used. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2-diphenyl ether) phenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)biphenyl] phenylvinyl)phenyl]anthracene (abbreviation: DPVPA), and the like.

[0065] In addition, poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenyl) PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine] N'-phenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( Polymer compounds such as [(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used. Cut.

[0066] By forming the hole injection layer 111, the hole injection property is improved, and the driving voltage is small. In addition, organic compounds with acceptor properties can be easily vapor-deposited. It is an easy-to-use material because it is easy to form a film.

[0067] The hole transport layer 112 is formed by containing a hole transport material. 0 -6 cm 2 It is preferable that the hole transport material has a hole mobility of 1 / Vs or more. As the hole transport material, the organic compound listed as the hole transport material usable for the composite material is used. It is possible to do so.

[0068] The light-emitting layer 113 is a layer containing a light-emitting material and a host material. The light-emitting material is a fluorescent material. Even if it is a phosphorescent material, it may be a material that exhibits thermally activated delayed fluorescence (TADF). It may be a single layer containing different light-emitting materials. In one embodiment of the present invention, the light-emitting layer 113 may be a fluorescent layer. This is more preferably applied to a layer that emits light, particularly a layer that emits blue fluorescent light. can.

[0069] In the light-emitting layer 113, materials that can be used as fluorescent materials include, for example: Examples include the following: Other fluorescent materials can also be used.

[0070] 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine PAP2BPy, 5,6-bis[4'-(10-phenyl-9-anthracene)- N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene 9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn ), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-di Phenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazo (4'-(10-phenyl-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation Name: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl N,9-diphenyl-2-anthryltriphenylamine (abbreviation: 2YGAPPA) N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole -3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-(tert -butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4' -(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCB APA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4 ,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine ] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl- 2-Anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA ), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N' -Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N' ,N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chloride Cen-2,7,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, N-(9 ,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3 -amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2- yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation Name: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9, 10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'- Triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-biphenyl Bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl) Phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N, N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 5 45T, N,N'-diphenylquinacridone, (abbreviation: DPQd), rubrene, 5,12 -Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl 2-(2-(4H-pyran-4-ylidene)propanedinitrile) (abbreviation: DCM1), Methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoline Lysin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation Name: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene 5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N', N'-Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3 ,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-( 1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanediyl tolyl (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7, 7-Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolin {4H-pyran-4-ylidene}propanedinitrile (abbreviated :DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl {4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCM), 2- {2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7 -tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H -pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJ™), N,N'- (pyren-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2- d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), 3,10-bis[ N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[ 2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV) -02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino] Naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf (IV)-02) In particular, 1,6FLPAPrn and 1,6mMemFL PAPrn, 1,6BnfAPrn-03, and other pyrene diamine compounds Synthetic aromatic diamine compounds have high hole trapping properties, and are excellent in luminous efficiency and reliability. This is preferable.

[0071] In the light-emitting layer 113, when a phosphorescent material is used as the light-emitting center material, Possible materials include, for example:

[0072] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III ) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl Iridium(III) (abbreviation: [Ir(Mpt z)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3 b) Organometallic iridium complexes with a 4H-triazole skeleton, such as 3), and tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazol- Zolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1 -methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium (III) (abbreviation: [Ir(PrptZ1-Me)3]) Organometallic iridium complexes with fac-tris[1-(2,6-diisopropyl phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimide Dazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmp and organometallic iridium complexes having an imidazole skeleton, such as impt-Me)3). Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium( III) Tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4' ,6'-difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) picolinate bis(2-[3',5'-bis(trifluoromethyl) fluoride] (abbreviation: FIrpic), Phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir( CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyri[ Ginat-N,C 2’ ]Iridium(III) acetylacetonate (abbreviation: FIr(ac Organometallic intermetallic compounds with phenylpyridine derivatives having electron-withdrawing groups such as ac)) as ligands These compounds exhibit blue phosphorescence, with an emission wavelength of 440 nm. It is a compound that has an emission peak at 520 nm.

[0073] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)yl Ir(tBuppm)3), (acetylacetonato)bis(Ir(tBuppm)3) (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(ac ac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpiperidinyl] [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II I) (abbreviation: [Ir(dppm)2(acac)]) Organic metal iridium complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl) Rupirazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyridine) Dinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) Organometallic iridium complexes with pyrazine skeletons such as tris(2-phenylpyridinium) Nat-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2- Phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzyl) Tribenzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris (2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq) 3]), bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylacetone Pyridine skeleton-containing compounds such as setonate (abbreviation: [Ir(pq)2(acac)]) In addition to organometallic iridium complexes, tris(acetylacetonato)(monophenanthroline)tetrahydrogen Rare earth metals such as rubium(III) (abbreviated as [Tb(acac)3(Phen)]) These are mainly compounds that exhibit green phosphorescence, with wavelengths ranging from 500 nm to 6 The emission peak is at 100 nm. The body is particularly preferred because it is remarkably excellent in reliability and luminous efficiency.

[0074] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] Nato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis [4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridine Ir(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organogold compounds with pyrimidine skeletons, such as [Ir(d1npm)2(dpm)] iridium complexes of the genus acetylacetonatobis(2,3,5-triphenylpyrazine) Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III)(abbreviation Name: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis (4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fd pq)2(acac)]), and organometallic iridium complexes with pyrazine skeletons such as Tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir (piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium (II I) Pyridyl acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with iridium skeletons, 2,3,7,8,12,13,17,18 -octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato) (monophenyl Anthroline) europium(III) (abbreviation: [Eu(DBM)3(Phen)]), Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthate) (Troline) europium(III) (abbreviation: [Eu(TTA)3(Phen)]) These are compounds that exhibit red phosphorescence and are The emission peak is between 0 nm and 700 nm. The rhodium complex emits red light with good chromaticity.

[0075] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting materials may be selected and used. stomach.

[0076] TADF materials include fullerene and its derivatives, acridine and its derivatives, and eosin. Derivatives of magnesium (Mg), zinc (Zn), cadmium, etc. can also be used. (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P d) and the like. Examples of the metal-containing porphyrin include: For example, the protoporphyrin-tin fluoride complex (SnF2(Pro to IX), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), Copropor Phyllin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4M e)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethiop Porphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin -platinum chloride complex (PtCl2OEP) and the like.

[0077] [ka]

[0078] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenyl)-4-phenyl-4-methyl-4-phenyl ... (phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine ( Abbreviation: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT zn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-yl] 4,6-diphenyl-1,3,5-triazine (abbreviated as '4,6-diphenyl-1,3,5-triazine- ...') Name: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl ]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4 -(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5- Diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-diphenyl Methyl-9H-acridin-10-yl)-9H-xanthen-9-one (Acr XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] Sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[a π electrons of clidin-9,9'-anthracen]-10'-one (abbreviation: ACRSA), etc. Heterocyclic compounds having either or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are also used. The heterocyclic compound may be a π-electron rich heteroaromatic ring or a π-electron deficient heteroaromatic ring. Since it has an aromatic ring, it has high electron transporting properties and hole transporting properties, which is preferable. Among the skeletons with a toe-shaped heteroaromatic ring, pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyridine skeleton) The arazine skeleton, pyridazine skeleton, and triazine skeleton are preferred because they are stable and reliable. In particular, benzofuropyrimidine skeleton, benzothienopyrimidine skeleton, benzofuropyrimidine skeleton, The benzothienopyrazine and benzothienopyrazine skeletons are preferred because they have high acceptor properties and good reliability. Among the skeletons having a π-electron-rich heteroaromatic ring, acridine skeletons, pheno The xanthazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are It is preferable that the compound has at least one of the above skeletons because it is stable and reliable. The furan skeleton is a dibenzofuran skeleton, and the thiophene skeleton is a dibenzothiophene skeleton. The pyrrole skeleton is preferably an indole skeleton, a carbazole skeleton, or a methylpyrrole skeleton. carbazole skeleton, indolocarbazole skeleton, bicarbazole skeleton, 3-(9-phenyl-9H- A carbazole-3-yl)-9H-carbazole skeleton is particularly preferred. A substance in which a π-type heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded is called a π-electron-rich heteroaromatic ring. The electron-donating property of the ring and the electron-accepting property of the π-electron-deficient heteroaromatic ring are both strong, and the S1 and T1 levels The energy difference between the levels is small, so thermally activated delayed fluorescence can be obtained efficiently. It is preferable that an electron-withdrawing group such as a cyano group is used instead of the π-electron-deficient heteroaromatic ring. In addition, the π-electron-rich skeleton may be an aromatic amine skeleton, a fluorine-containing skeleton, or the like. A phenazine skeleton or the like can be used. In addition, a xanthene skeleton can be used as a π-electron deficient skeleton. , thioxanthene dioxide skeleton, oxadiazole skeleton, triazole skeleton, imidazoline azole skeleton, anthraquinone skeleton, boron-containing skeletons such as phenylborane and boranthrene, Aromatic rings or heterocyclic rings containing nitrile or cyano groups such as benzonitrile or cyanobenzene Aromatic rings, carbonyl skeletons such as benzophenone, phosphine oxide skeletons, sulfone skeletons, etc. In this way, a π-electron deficient heteroaromatic ring and a π-electron rich heteroaromatic ring can be used. Using a π-electron deficient skeleton and a π-electron rich skeleton in place of at least one of the aromatic rings can be done.

[0079] [ka]

[0080] TADF materials have a small difference between the S1 and T1 levels, and triple intersystem crossing occurs due to reverse intersystem crossing. The function of converting energy from first excitation energy to singlet excitation energy Therefore, the triplet excitation energy can be converted to a single state by a small amount of thermal energy. It is possible to upconvert to doublet excited energy (reverse intersystem crossing), and efficiently convert the singlet excited state It is possible to generate triplet excitation energy and convert it into luminescence. .

[0081] In addition, exciplexes (exciplexes) that form excited states with two types of substances The difference between the S1 and T1 levels is extremely small, As a TADF material capable of converting triplet excitation energy into singlet excitation energy, It has all the functions.

[0082] As an index of the T1 level, the phosphorescence spectrum observed at low temperatures (for example, from 77 K to 10 K) As for TADF materials, the fluorescent light spectrum has a short wavelength tail. Draw a tangent line to the S1 level, and the energy of the wavelength of the extrapolated line is the S1 level. When a tangent line is drawn at the long side of the tail and the energy of the wavelength of the extrapolated line is taken as the T1 level, The difference between S1 and T1 is preferably 0.3 eV or less, and more preferably 0.2 eV or less. Even more preferable.

[0083] In addition, when a TADF material is used as the luminescent center material, the S1 level of the host material is It is preferable that the T1 level of the host material is higher than the T1 level of the TADF material. A level higher than 1 is preferred.

[0084] As the host material of the light-emitting layer, the host material agent according to one aspect of the present invention described in Embodiment 1 may be used. It is preferable to use an anthracene compound for the host material. This makes it possible to provide a light-emitting device with a long life.

[0085] In addition, the anthracene compound for a host material described in Embodiment 1 is not used as a host material. In this case, various carrier transport materials such as materials with electron transport properties and materials with hole transport properties are used. can be used.

[0086] As a material having hole transport properties, 4,4'-bis[N-(1-naphthyl)-N-phenyl] N,N'-bis(3-methylphenyl)-N, N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl]a 4-phenyl-4'-(9-phenylfluorene)biphenyl (abbreviation: BSPB), -9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9- (phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-fluoren-9-yl Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine ( PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-chlor PCBBi1BP, 4-(1-naphtho-3-yl)triphenylamine ethyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine( Abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H -carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl thyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]phenyl N-phenyl-N-[4-(9- (phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene Compounds with aromatic amine skeletons such as 1,3-2-amine (abbreviated as PCBASF) and -bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl) Biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9- Phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) Compounds with a carbazole skeleton, such as 4,4',4 ''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT 3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9 -yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-( 9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiof Compounds with a thiophene skeleton, such as 4,4', 4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3 P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl ]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) Among the above, compounds having an aromatic amine skeleton and carbazoline Compounds having a hole skeleton have good reliability, high hole transport properties, and low driving voltage. In addition, the organic compounds described in the first embodiment can also be preferably used. This can be done.

[0087] Examples of materials having electron transport properties include bis(10-hydroxybenzo[h]quinolinol). Nat)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato) )(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8- Quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) phenolato]zinc(II) (abbreviation: ZnBTZ) and other metal complexes, (4-tert-butylphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation :PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) phenyl)-1,2,4-triazole (abbreviation: TAZ), 2-[3'-(9,9-dimethyl

[0043] -4,6-difluoro-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl Phenyl-1,3,5-triazine (abbreviation: mFBPTzn), 1,3-bis[5-(p- tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation Name: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl] 2,2',2''-(1,3-phenyl)phenyl]-9H-carbazole (abbreviation: CO11), ,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole)(abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl- 1H-Benzimidazole (abbreviation: mDBTBIm-II), 2-{4-[9,10-di (Naphthalen-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzo Heterocyclic compounds with polyazole skeletons such as imidazole (abbreviation: ZADN) and 2- [3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline ( Abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl] phenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq- II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibene 2mCzBPDBq, 4,6-bis[3-(phenanthroline) 4,6-(4,6-benzothren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), Bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2 Heterocyclic compounds with diazine skeletons such as Pm-II) and 3,5-bis[3-(9H- carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5 -tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB) Among the above, heterocyclic compounds having a diazine skeleton are preferred. A heterocyclic compound having a pyridine skeleton and a heterocyclic compound having a pyridine skeleton are preferred because of their high reliability. Heterocyclic compounds with a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties and are suitable for It also contributes to reducing dynamic voltage.

[0088] When a fluorescent substance is used as the light-emitting material, the host material is a compound having an anthracene skeleton. A material having an anthracene skeleton is preferably used as a host material for a fluorescent material. When used in this way, it is possible to realize a light-emitting layer having good luminous efficiency and durability. Many materials having a Csene skeleton have a deep HOMO level, and therefore, one embodiment of the present invention is preferably applied to The substance having an anthracene skeleton used as the host material can be Substances with a phenylanthracene skeleton, especially a 9,10-diphenylanthracene skeleton, It is preferable because it is chemically stable. In addition, when the host material has a carbazole skeleton, This is preferable because it improves the hole injection and transport properties, but the benzene ring is further condensed to the carbazole. When the benzocarbazole skeleton is included, the HOMO is shallower than that of carbazole by about 0.1 eV. This is particularly preferable since the host material is dibenzocarbazoline. When a carbazole skeleton is included, the HOMO is shallower than that of carbazole by about 0.1 eV, and holes can enter. This is preferable because it makes it easier to attach the film, has excellent hole transport properties, and has high heat resistance. Further, preferred host materials include those having a 9,10-diphenylanthracene skeleton and Carbazole skeleton (or benzocarbazole skeleton or dibenzocarbazole skeleton) From the viewpoint of the hole injection and transport properties mentioned above, it is desirable to use a carbazole skeleton. Alternatively, a benzofluorene skeleton or a dibenzofluorene skeleton may be used. Examples of substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl] 3-[4-(1-naphthyl)-phenyl]-9H-carbazole (abbreviation: PCzPA), 9-[4-(10-phenyl)-9H-carbazole (abbreviation: PCPN), 7-[4-( ... -(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazo (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl )phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl -4'-yl}anthracene (abbreviation: FLPPA), etc. gDBCzPA, 2mBnfPPA, and PCzPA are preferred because they show very good properties. It is a good choice.

[0089] Note that the light-emitting device of one embodiment of the present invention is particularly suitable for a light-emitting device that emits blue fluorescent light. It is preferable to use

[0090] The host material may be a mixture of a plurality of substances. When used, a material having an electron transporting property and a material having a hole transporting property may be mixed. It is preferable to mix a material having an electron transport property with a material having a hole transport property. Therefore, the transport property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The ratio of the content of the material having hole transport properties to the content of the material having electron transport properties is The ratio of the material having electron transport properties to the material having electron transport properties may be 1:9 to 9:1.

[0091] Furthermore, these mixed materials may form an exciplex. The exciplex is formed to emit light that overlaps with the wavelength of the lowest energy absorption band of By selecting such a combination, energy transfer becomes smooth and light emission can be obtained efficiently. In addition, the use of this configuration is also preferable because the driving voltage is reduced.

[0092] The electron transport layer 114 is a layer containing a substance having an electron transport property. Examples of the electron-transporting material include those listed as the materials having an electron-transporting property that can be used as the host material. can be used.

[0093] Between the electron transport layer 114 and the second electrode 102, a lithium fluoride layer was formed as an electron injection layer 115. Lithium (LiF), 8-hydroxyquinolinato-lithium (abbreviated as Liq), Cesium fluoride Alkali metal or alkaline earth metals such as (CsF), calcium fluoride (CaF2), etc. The electron injection layer 115 may be a layer containing a metal or a compound thereof. The layer is made of a material containing an alkali metal or alkaline earth metal or a compound thereof. As the electride, for example, calcium carbonate may be used. Examples include a material in which a high concentration of electrons is added to a mixed oxide of silicon and aluminum.

[0094] Moreover, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1B). By applying a potential to the layer 116, holes are introduced to the layer in contact with the cathode side of the layer, and electrons are introduced to the layer in contact with the anode side of the layer. The charge generation layer 116 is a layer that can inject electrons into the adjacent layer. Both layers include a P-type layer 117. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form the P-type layer 117 using the composite material mentioned above as a material that can be used. The composite material is a film containing the above-mentioned acceptor material and a hole transport material. By applying a potential to the P-type layer 117, an electron transport Electrons are injected into layer 114 and holes are injected into the second electrode 102, which is the cathode, and the light-emitting device operates. do.

[0095] The charge generation layer 116 includes an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117. Preferably, one or both of layers 119 are provided.

[0096] The electron relay layer 118 contains at least a substance having electron transport properties, and the electron injection buffer layer 1 The electrons are transferred smoothly by preventing the interaction between the P-type layer 117 and the P-type layer 119. The LUMO level of the substance having electron transport properties contained in the relay layer 118 is The LUMO level of the acceptor material in the electron transport layer 114 and the charge generation layer 116 It is preferable that the LUMO level of the electron relay layer 11 is between the LUMO level of the material contained in the adjacent layer. Specific energy levels of the LUMO level in the electron transporting materials used in 8 is set to -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. The electron-transporting material used in the electron relay layer 118 is a phthalocyanine-based material. It is preferred to use materials or metal complexes having metal-oxygen bonds and aromatic ligands.

[0097] The electron injection buffer layer 119 contains an alkali metal, an alkaline earth metal, a rare earth metal, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, lithium carbonate) Alkaline earth metal compounds (including carbonates such as titanium and cesium carbonate), alkaline earth metal compounds (oxides, halogens compounds of rare earth metals (including oxides, halides, carbonates) or compounds of rare earth metals (including oxides, halides, carbonates) It is possible to use a material with high electron injection properties, such as SiO 2 .

[0098] The electron injection buffer layer 119 is formed by containing a substance having an electron transporting property and a donor substance. When the donor material is an alkali metal, an alkaline earth metal, or a rare earth metal, and their compounds (alkali metal compounds (oxides such as lithium oxide, halides , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, compounds of rare earth metals (including oxides, halides, carbonates) In addition to tetrathianaphthacene (abbreviated as TTN), nickelocene, decamethicone, An organic compound such as nickelocene can also be used. The electron transport layer 114 may be formed using the same material as that used for forming the electron transport layer 114 described above. This can be done.

[0099] The material forming the second electrode 102 is preferably one having a small work function (specifically, 3.8 eV or less). Bottom) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs). Lithium metals, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or 2 of the Periodic Table of Elements, and alloys containing these elements (MgAg, Rare earth metals such as AlLi), europium (Eu), ytterbium (Yb) and the like, However, when the second electrode 102 and the electron transport layer are connected to each other, By providing an electron injection layer, it is possible to use Al, Ag, ITO, silicon, etc., regardless of the magnitude of the work function. Various conductive materials such as indium oxide-tin oxide containing silicon oxide or silicon oxide are used as the second It can be used as the electrode 102. These conductive materials can be applied by dry methods such as vacuum deposition and sputtering, inkjet printing, It is possible to form the film using a spin coating method, etc. Also, it is possible to form the film using a wet sol-gel method. Alternatively, the metal layer may be formed by a wet method using a paste of a metal material.

[0100] The EL layer 103 can be formed by various methods, including dry and wet methods. For example, vacuum deposition, gravure printing, offset printing, screen printing, etc. A printing method, an ink jet method, a spin coating method, or the like may also be used.

[0101] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0102] The structure of the layer provided between the first electrode 101 and the second electrode 102 is the same as that described above. However, it is not limited to the above. The first electrode 101 and the second electrode 102 are arranged so as to suppress quenching caused by the A preferred configuration is one in which a light-emitting region where holes and electrons recombine is provided at a location away from O2.

[0103] Furthermore, recombination in the hole transport layer or electron transport layer in contact with the light-emitting layer 113, particularly in the light-emitting layer 113 The carrier transport layer close to the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is determined by the luminescent material that constitutes the luminescent layer or the luminescent material contained in the luminescent layer. It is preferable that the material be made of a substance having a band gap larger than the band gap of the material. I wish.

[0104] Next, we developed a light-emitting device (a stacked element, a tandem element) that has a structure in which multiple light-emitting units are stacked. An embodiment of the light-emitting device (also referred to as a "diode") will be described with reference to FIG. 1C. A light-emitting device has multiple light-emitting units between the cathode and the cathode. , has a configuration similar to that of the EL layer 103 shown in FIGS. 1A1, 1A2, and 1B. That is, the light-emitting device shown in FIG. 1C is a light-emitting device having a plurality of light-emitting units. The light-emitting devices shown in FIGS. 1A1, 1A2 and 1B are light-emitting devices having one light-emitting unit. It can be said to be an optical device.

[0105] In FIG. 1C, a first light-emitting unit 511 and a second light-emitting unit 512 are disposed between the anode 501 and the cathode 502. The first light-emitting unit 511 and the second light-emitting unit 512 are stacked. A charge generating layer 513 is provided between the anode 501 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in FIG. 1A1 and the like, and The same as described above can be applied. The second light-emitting units 512 may be of the same or different configuration.

[0106] When a voltage is applied between the anode 501 and the cathode 502, the charge generating layer 513 generates a light emitting The electron-injecting unit has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit. At 1C, when a voltage is applied so that the anode potential is higher than the cathode potential, The charge generation layer 513 injects electrons into the first light-emitting unit 511 and Any material capable of injecting holes into 12 may be used.

[0107] The charge generation layer 513 is formed to have the same structure as the charge generation layer 116 described in FIG. 1B. The composite material of an organic compound and a metal oxide has excellent carrier injection and carrier transport properties. Because of its excellent properties, it can be driven at low voltage and low current. When the anode side surface of the charge generating layer 513 is in contact with the charge generating layer 513, the charge generating layer 513 is in contact with the light emitting unit Since the EL layer can also function as a hole injection layer, the EL unit can be formed without providing a hole injection layer. good.

[0108] In addition, when the electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer Since the electron injection layer 119 plays the role of an electron injection layer in the light-emitting unit on the anode side, the light-emitting layer The unit does not necessarily need to have an electron injection layer.

[0109] Although the light-emitting device having two light-emitting units is described in FIG. 1C, a light-emitting device having three or more light-emitting units may be used. The present invention can be similarly applied to a light-emitting device in which light-emitting units are stacked. As in the light-emitting device according to the embodiment, a plurality of light-emitting units are formed between a pair of electrodes to generate electric charges. By separating the layers with the layer 513, high brightness light emission is possible while keeping the current density low. Furthermore, a light-emitting device that can be driven at a low voltage and consumes less power can be realized. This can be achieved.

[0110] In addition, by making the light color of each light-emitting unit different, the light-emitting device as a whole can be For example, a light-emitting device having two light-emitting units can be used to obtain light of a desired color. In this device, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. By obtaining a color, it is possible to obtain a light-emitting device that emits white light as a whole. In the case of a three-layer structure, the first light-emitting unit emits blue light, and the second light-emitting unit emits blue light. White light can be obtained by using a first light-emitting unit to obtain red and green light, and a third light-emitting unit to obtain blue light. .

[0111] In addition, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and Each layer such as the charge generating layer and the electrodes can be formed by, for example, a vapor deposition method (including a vacuum deposition method), a droplet discharge method (including an ink jet method), or the like. It can be formed by using methods such as ink jet printing, coating, and gravure printing. They can be used in low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), or polymeric material.

[0112] (Embodiment 3) In this embodiment, light emission using the light-emitting device described in the first and second embodiments is The device will now be described.

[0113] In this embodiment, a light-emitting device described in Embodiments 1 and 2 is used to manufacture a The light-emitting device will be described with reference to FIG. 2. FIG. 2A is a top view showing the light-emitting device. 2B is a cross-sectional view taken along lines AB and CD in FIG. 2A. The drive circuit (source line drive circuit) shown by the dotted line controls the light emission of the device. 601, a pixel portion 602, and a driving circuit portion (gate line driving circuit) 603. 604 is a sealing substrate, 605 is a sealing material, and the inside surrounded by the sealing material 605 is a space 60 It's now 7.

[0114] The lead wiring 608 is connected to the source line driver circuit 601 and the gate line driver circuit 603. The wiring is for transmitting signals, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal, etc. from the input circuit 609 Although only the FPC is shown here, this FPC has a printed wiring board. The light emitting device in this specification may be a light emitting device. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0115] Next, the cross-sectional structure will be described with reference to FIG. A pixel portion is formed, and here, a source line driver circuit 601 which is a driver circuit portion and a pixel One pixel in element portion 602 is shown.

[0116] The element substrate 610 may be a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl It is made using a plastic substrate made of, for example, fluoride, polyester, or acrylic. That's fine.

[0117] The structure of the transistors used in the pixels and driver circuits is not particularly limited. The transistor may be a top-type transistor or a staggered type transistor. The transistor may be a gate type transistor or a bottom gate type transistor. The semiconductor material is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and nitride. Gallium or the like can be used. Alternatively, in-type metal oxides such as In-Ga-Zn-based metal oxides can be used. An oxide semiconductor containing at least one of tungsten, gallium, and zinc may be used.

[0118] The crystallinity of the semiconductor material used in the transistor is not particularly limited. A semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or a semiconductor having a partially crystalline region) When a semiconductor having crystallinity is used, the transistor This is preferable because it can suppress deterioration of the star characteristics.

[0119] Here, in addition to the transistors provided in the pixels and the driver circuits, It is preferable to use an oxide semiconductor for a semiconductor device such as a transistor. In particular, it is preferable to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than silicon, the off-state of the transistor can be This can reduce the current in the

[0120] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn). In addition, In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is preferable that the oxide semiconductor contains an oxide represented by the formula (metal such as La, Ce or Hf). More preferable.

[0121] Here, an oxide semiconductor that can be used in one embodiment of the present invention will be described below. .

[0122] Oxide semiconductors are divided into single-crystal oxide semiconductors and other non-single-crystal oxide semiconductors. As a non-single-crystal oxide semiconductor, for example, CAAC-OS (c-axis alignable oxide semiconductor) gned crystalline oxide semiconductor), polycrystalline nc-OS (nano crystalline oxide semiconductor) semiconductor), pseudo-amorphous oxide semiconductor (a-like OS) amorphous-like oxide semiconductor), and amorphous oxide semiconductor Conductors, etc.

[0123] CAAC-OS has a c-axis orientation and multiple nanocrystals are connected in the ab-plane direction. The crystal structure has distortion. The distortion is the area where multiple nanocrystals are connected. In the region, the lattice arrangement is changed between a region with a uniform lattice arrangement and another region with a uniform lattice arrangement. Indicates the point where the direction is changing.

[0124] Nanocrystals are basically hexagonal, but they are not limited to regular hexagonal shapes and may be non-regular hexagonal. The distortion may also have lattice arrangements such as pentagons and heptagons. In CAAC-OS, clear grain boundaries (grain boundaries) are observed even near the strain. It is difficult to confirm the presence of grains due to distortion of the lattice arrangement. This is because the CAAC-OS has a crystalline structure in the ab-plane direction. The oxygen atoms are not densely packed, and the bond distance between atoms is shortened by the substitution of metal elements. This is because distortion can be tolerated by changing the frequency.

[0125] In addition, the CAAC-OS has a layer containing indium and oxygen (hereinafter referred to as an In layer) and an element A layered crystal structure in which layers containing M, zinc, and oxygen (hereinafter referred to as (M, Zn) layers) are stacked. It is noted that indium and element M tend to have a layered structure. It is possible, and when the element M in the (M,Zn) layer is replaced with indium, (In,M,Zn) Also, when indium in the In layer is replaced with element M, (In,M ) layer.

[0126] CAAC-OS is an oxide semiconductor with high crystallinity. Since it is difficult to identify grain boundaries, the decrease in electron mobility caused by grain boundaries is unlikely to occur. In addition, the crystallinity of oxide semiconductors is degraded by the inclusion of impurities and the generation of defects. Therefore, CAAC-OS should be free from impurities and defects (oxygen vacancies (V O :oxygen Therefore, CAA Oxide semiconductors containing C-OS have stable physical properties. The oxide semiconductor has high heat resistance and high reliability.

[0127] nc-OS is a material that can be used in microscopic areas (e.g., areas between 1 nm and 10 nm, especially areas between 1 nm and 3 nm). The nc-OS has periodic atomic arrangement in the nanometer range (nm or less). There is no regularity in the crystal orientation between the crystals. Therefore, no orientation is observed throughout the film. Therefore, depending on the analysis method, nc-OS may be distinguished from a-like OS or amorphous oxide semiconductor. It may be difficult to distinguish between the two.

[0128] Note that indium, gallium, and zinc are oxide semiconductors. The IGZO nanocrystals mentioned above are stable. In particular, IGZO tends to have difficulty growing crystals in the atmosphere. , small crystals (e.g., crystals of several mm or several cm) are more likely to be formed than large crystals (here, crystals of several mm or several cm). For example, the nanocrystals mentioned above may be structurally more stable.

[0129] The a-like OS is an oxide semiconductor with a structure between the nc-OS and amorphous oxide semiconductor. Conductive. A-like OS has voids or low density regions. The ke-OS has lower crystallinity than the nc-OS and CAAC-OS.

[0130] Oxide semiconductors have a variety of structures, each of which has different characteristics. Oxide semiconductors include amorphous oxide semiconductors, polycrystalline oxide semiconductors, a-like OS, and nc The compound may have two or more of -OS and CAAC-OS.

[0131] In addition to the oxide semiconductors mentioned above, Cloud-Aligned Computing (CAC) osite)-OS may also be used.

[0132] CAC-OS is a material that has a conductive function in some parts and an insulating function in other parts. The material as a whole functions as a semiconductor. When used in the semiconductor layer of The insulating function is the function of preventing the flow of electrons, which act as carriers. The function of switching is achieved by making the insulating function and the switching function ( On / Off function) can be added to CAC-OS. By separating the functions of each, the functions of both can be maximized.

[0133] The CAC-OS also has a conductive region and an insulating region. The insulating region has the above-mentioned insulating function. In some cases, the conductive and insulating regions are separated at the nanoparticle level. The conductive and insulating regions may be unevenly distributed in the material. may be observed as a cloud-like cluster with the periphery blurred.

[0134] In addition, in CAC-OS, the conductive region and the insulating region are each 0.5 nm or more. When the particles are dispersed in the material in a size of 10 nm or less, preferably 0.5 nm to 3 nm, There is a match.

[0135] In addition, the CAC-OS is composed of components having different band gaps. For example, CAC-OS consists of a wide-gap component originating from the insulating region and a conductive component originating from the conductive region. In this configuration, the carrier is When the carriers flow, they mainly flow in the narrow gap component. The component with a gap acts complementary to the component with a wide gap, Carriers flow into the wide-gap component in conjunction with the wide-gap component. When the CAC-OS is used in a channel forming region of a transistor, In the on state, a high current driving force, i.e., a large on-current, and a high field-effect mobility are obtained. It is possible.

[0136] That is, CAC-OS is a matrix composite. , or metal matrix composite It can also be called.

[0137] By using the above-mentioned oxide semiconductor material for the semiconductor layer, fluctuations in electrical characteristics are suppressed and reliability is improved. This makes it possible to realize highly reliable transistors.

[0138] Furthermore, the transistor having the above-described semiconductor layer can be used as a transistor due to its low off-state current. It is possible to retain the charge stored in the capacitor for a long period of time through such a transistor. By applying a transistor to each pixel, the gradation of the image displayed in each display area can be maintained while driving It is also possible to shut down the circuit. As a result, electronic devices with extremely low power consumption can be realized. It can be realized.

[0139] For stabilizing the characteristics of the transistor, it is preferable to provide an underlayer film. Inorganic films such as silicon oxide film, silicon nitride film, silicon oxynitride film, and silicon nitride oxide film The insulating film can be formed as a single layer or a laminated layer. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), ALD ( Formed using Atomic Layer Deposition (ALD), coating, printing, etc. It should be noted that the undercoat film need not be provided if it is not necessary.

[0140] The FET 623 indicates one of the transistors formed in the driving circuit section 601. The drive circuit is made up of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment, a driver integrated type in which a driving circuit is formed on a substrate is shown. However, this is not necessarily required, and the drive circuit can be formed externally rather than on the substrate. .

[0141] The pixel section 602 includes a switching FET 611, a current control FET 612 and its driver. The pixel is formed by a plurality of pixels including a first electrode 613 electrically connected to the drain. However, the present invention is not limited to this, and a pixel unit that combines three or more FETs and a capacitance element may also be used. good.

[0142] An insulator 614 is formed to cover the end of the first electrode 613. It can be formed by using a photosensitive acrylic mold.

[0143] In order to improve the coverage of the EL layer and the like to be formed later, the insulating material 614 is For example, the material of the insulator 614 is When a positive photosensitive acrylic is used, the radius of curvature (0. It is preferable that the insulating material 614 has a curved surface with a thickness of 2 μm to 3 μm. Either a negative photosensitive resin or a positive photosensitive resin can be used.

[0144] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, the material used for the first electrode 613 has a large work function. For example, an ITO film or a silicon-containing indium tin oxide film, Indium oxide film containing up to 20 wt% zinc oxide, titanium nitride film, chromium film, tungsten film In addition to single layer films such as titanium nitride film, Zn film, and Pt film, films mainly composed of titanium nitride film and aluminum and a three-layer structure consisting of a titanium nitride film, a film mainly composed of aluminum, and a titanium nitride film. In addition, when a laminated structure is used, the resistance as a wiring is low and a good overcoat can be obtained. It can be made to have good contact with the electrode and can also function as an anode.

[0145] The EL layer 616 can be formed by a deposition method using a deposition mask, an inkjet method, or a spin coating method. The EL layer 616 is formed by various methods such as those described in the first and second embodiments. Other materials that make up the EL layer 616 include: It may be a low molecular weight compound or a high molecular weight compound (including an oligomer or dendrimer). .

[0146] Furthermore, the material used for the second electrode 617 formed on the EL layer 616 is selected from those having a work function Materials with low porosity (Al, Mg, Li, Ca) or their alloys and compounds (MgAg, Mg It is preferable to use In, AlLi, etc. When the first electrode 617 is to be transparent, a thin metal film having a small thickness is used as the second electrode 617. and a transparent conductive film (ITO, indium oxide containing 2-20 wt% zinc oxide, silicon It is preferable to use a laminate of indium tin oxide, zinc oxide (ZnO), or the like having such a structure.

[0147] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting device. The light-emitting device is the light-emitting device described in the first and second embodiments. The pixel portion is formed with a plurality of light-emitting devices. The light emitting device in the present invention comprises the light emitting device according to the first embodiment and the light emitting device according to the second embodiment. The light emitting device may include both a light emitting device having a configuration other than the above.

[0148] Furthermore, the sealing substrate 604 is bonded to the element substrate 610 with a sealing material 605. A light-emitting device is placed in a space 607 surrounded by a sub-substrate 610, a sealing substrate 604, and a sealing material 605. The space 607 is filled with a filler material. In some cases, the gas is filled with an inert gas (nitrogen, argon, etc.), and in other cases, it is filled with a sealing material. By forming a recess in the sealing substrate and providing a desiccant there, deterioration due to the influence of moisture can be prevented. This is a preferable configuration because it can suppress the degradation.

[0149] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is desirable that these materials be as impermeable to moisture and oxygen as possible. Materials used for the sealing substrate 604 include glass substrates, quartz substrates, and FRP (Fiber Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyethylene or acrylic can be used.

[0150] Although not shown in Figure 2, a protective film may be provided on the cathode. The insulating film may be formed. In addition, a protective film may be formed to cover the exposed portion of the sealing material 605. The protective film may be formed on the surfaces and sides of the pair of substrates, the sealing layer, the insulating layer, It can be provided to cover the exposed side surfaces of the above.

[0151] The protective film can be made of a material that is difficult for impurities such as water to permeate. It is possible to effectively prevent impurities such as these from diffusing from the outside to the inside.

[0152] The materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers and the like can be used, for example, aluminum oxide, hafnium oxide, hafnium Lanthanum silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide , titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide , cerium oxide, scandium oxide, erbium oxide, vanadium oxide or indium oxide Materials containing hafnium, aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride, etc. Materials, nitrides containing titanium and aluminum, oxides containing titanium and aluminum , oxides containing aluminum and zinc, sulfides containing manganese and zinc, cerium and sulfides containing erbium and strontium, oxides containing erbium and aluminum, yttrium Materials containing oxides containing lithium and zirconium can be used.

[0153] The protective film can be formed using a film formation method that provides good step coverage. One such method is atomic layer deposition (ALD). The ALD method can be used to form protective materials. It is preferable to use it for films. By using the ALD method, it is possible to eliminate cracks, pinholes, etc. It is possible to form a protective film with reduced defects or with a uniform thickness. Damage to the processed member when forming the protective film can be reduced.

[0154] For example, by forming a protective film using the ALD method, it is possible to fabricate a surface with complex irregularities or a surface with a touch panel. A uniform protective film with few defects can be formed on the top, sides and back of the panel. .

[0155] As described above, the light-emitting devices described in the first and second embodiments were used to manufacture the A light emitting device having such a structure can be obtained.

[0156] The light emitting device of the present embodiment is the same as the light emitting device of the first and second embodiments. Since the semiconductor device is used, it is possible to obtain a light emitting device with excellent characteristics. The light emitting devices described in the first and second embodiments are light emitting devices with long lifetimes. Therefore, a light emitting device with good reliability can be obtained. 2. A light-emitting device using the light-emitting device described in 2. has good luminous efficiency, and therefore consumes little power. It may be an optical device.

[0157] In FIG. 3, a light-emitting device that emits white light is formed, and a colored layer (color filter) is provided. 3A shows an example of a full-color light-emitting device. film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, first An interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driving The driving circuit part 1041, the anodes 1024W, 1024R, 1024G, and 1024 of the light-emitting device B, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting device, and a sealing substrate 10 31, sealing material 1032, etc. are shown.

[0158] In addition, in FIG. 3A, the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer The color layer 1034B is provided on a transparent substrate 1033. Also, the black matrix 103 A transparent substrate 103 on which a colored layer and a black matrix are provided may be further provided. 3 is aligned and fixed to the substrate 1001. The colored layer and the black matrix 1035 is covered with an overcoat layer 1036. Also, in FIG. The light-emitting layer emits light to the outside without passing through the colored layer, and the light-emitting layer emits light to the outside by passing through the colored layer of each color. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, green, or blue. This allows images to be expressed using four color pixels.

[0159] In FIG. 3B, the color layers (red color layer 1034R, green color layer 1034G, blue color layer 1034R) are 034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020. In this way, the colored layer may be provided between the substrate 1001 and the sealing substrate 1031. stomach.

[0160] In the light emitting device described above, light is taken in toward the substrate 1001 on which the FET is formed. The light emitting device has a bottom emission structure, but the light is taken in from the sealing substrate 1031 side. The light emitting device may have a top emission structure. A cross-sectional view of the light-emitting device is shown in FIG. 4. In this case, a substrate that does not transmit light is used as the substrate 1001. Until the connection electrode that connects the FET and the anode of the light-emitting device is fabricated, After that, a third interlayer insulating film 1037 is formed on the substrate 1031 in the same manner as in the case of the multi-emission light emitting device. The insulating film is formed to cover the electrode 1022. This insulating film may also serve as a planarizing layer. The interlayer insulating film 1037 may be formed using the same material as the second interlayer insulating film, or other known materials. It is possible.

[0161] The anodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device are the anodes here. However, it may be formed as a cathode. In the case of an optical device, it is preferable that the anode is a reflective electrode. The EL layer 103 has the same structure as that described in the first and second embodiments, and In addition, the device structure is designed to produce white light emission.

[0162] In the top emission structure shown in Figure 4, the colored layers (red colored layer 1034R, green colored layer The sealing is performed by a sealing substrate 1031 provided with a blue color layer 1034G and a blue color layer 1034B. The sealing substrate 1031 has a black matrix disposed between the pixels. A coloring layer (red coloring layer 1034R, green coloring layer 1034G, The blue colored layer (1034B) and the black matrix are covered with an overcoat layer. Note that a light-transmitting substrate is used as the sealing substrate 1031. In this example, a full-color display using four colors, red, green, blue, and white, is shown. However, the present invention is not limited to this. A full color display may be achieved using four colors, yellow, green, and blue, or three colors, red, green, and blue.

[0163] In a top-emission type light-emitting device, the microcavity structure can be suitably applied. The light-emitting device with a microcavity structure uses the anode as a reflective electrode and the cathode as a semi-transparent / semi-reflective electrode. At least one electrode is provided between the reflective electrode and the semi-transparent / semi-reflective electrode. It has an EL layer, and at least has a light-emitting layer that becomes a light-emitting region.

[0164] The reflectance of the reflective electrode for visible light is 40% to 100%, preferably 70% to 100%. %, and its resistivity is 1×10 -2 The film is assumed to be less than Ωcm. The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1×10 -2 It is assumed that the film has a resistance of Ωcm or less.

[0165] The light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transparent and semi-reflective electrode. The sound is reflected and resonates.

[0166] The light-emitting device is made by changing the thickness of the transparent conductive film, the composite material, the carrier transport material, etc. By doing so, the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode can be changed. This strengthens the light of the resonating wavelength between the reflective electrode and the semi-transparent and semi-reflective electrode, and It can attenuate light of wavelengths that are not

[0167] The light reflected by the reflective electrode and returned (first reflected light) is semi-transmitted from the light emitting layer. The light that directly enters the semi-reflective electrode (first incident light) interferes greatly with the reflective electrode. The optical distance of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the amplified It is preferable to adjust the optical distance to a wavelength of the first light. By matching the phase of the reflected light with the phase of the first incident light, the light emitted from the light-emitting layer can be further amplified. do.

[0168] In the above configuration, even if the EL layer has a plurality of light-emitting layers, a single light-emitting For example, it may be combined with the above-mentioned tandem light-emitting device configuration. In addition, multiple EL layers are provided in one light-emitting device with a charge generating layer sandwiched between them, and each EL The layer may be configured to have one or more light-emitting layers.

[0169] The microcavity structure makes it possible to enhance the front-direction emission intensity of specific wavelengths. This allows for lower power consumption. In the case of a light-emitting device that displays images using a single pixel, the yellow light emission not only improves brightness, but also Since a microcavity structure tailored to the wavelength of each color can be applied, it is possible to achieve light-emitting devices with excellent characteristics. It can be placed.

[0170] The light emitting device of the present embodiment is the same as the light emitting device of the first and second embodiments. Since the semiconductor device is used, it is possible to obtain a light emitting device with excellent characteristics. The light emitting devices described in the first and second embodiments are light emitting devices with long lifetimes. Therefore, a light emitting device with good reliability can be obtained. 2. A light-emitting device using the light-emitting device described in 2. has good luminous efficiency, and therefore consumes little power. It may be an optical device.

[0171] Up to this point, we have explained about active matrix light emitting devices, but from now on we will be talking about passive light emitting devices. A passive matrix light-emitting device will be described. 5A is a perspective view showing the light-emitting device, and FIG. 5B is a perspective view showing the light-emitting device. 5A is a cross-sectional view taken along the line XY. In FIG. 5, an electrode 952 and a An EL layer 955 is provided between the electrode 952 and the insulating layer 953. The insulating layer 953 is covered with a barrier layer 954. The side walls of 54 are spaced apart from one another as they approach the substrate surface. That is, the cross section of the partition layer 954 in the short side direction is trapezoidal, The bottom side (the side that faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) is the top side (the side that faces in the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953). In this way, by providing the partition layer 954, defects in the light-emitting device due to static electricity or the like can be prevented. In addition, the passive matrix light emitting device can also be manufactured in accordance with the method of the first embodiment. and a light emitting device or a consumer device having high reliability, which uses the light emitting device according to the second embodiment. A light emitting device with low power consumption can be obtained.

[0172] The light emitting device described above is composed of a large number of minute light emitting devices arranged in a matrix. Since it is possible to control each of these, it can be suitably used as a display device for displaying images. It is a light-emitting device.

[0173] This embodiment mode can be freely combined with other embodiment modes.

[0174] (Fourth embodiment) In this embodiment, the light-emitting device according to any one of the first and second embodiments is used as a lighting device. An example of using the lighting device as a lighting fixture will be described with reference to FIG. 6. FIG. 6B is a top view of the lighting device, and FIG. 6A is a top view of the lighting device. FIG. 5 is a cross-sectional view of the line ef in FIG.

[0175] The lighting device of this embodiment is a light-transmitting substrate 400 serving as a support, on which a first The first electrode 401 is formed on the substrate 10. The first electrode 401 is the same as the first electrode 10 in the second embodiment. When light is extracted from the first electrode 401 side, the first electrode 401 is made of a transparent material. The material is formed from a material having the following properties.

[0176] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0177] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is the same as that in the first embodiment. The configuration of the EL layer 103 in the second embodiment, or the light-emitting units 511 and 512 and the This corresponds to a configuration in which the charge generating layer 513 is combined. Please refer to.

[0178] The second electrode 404 is formed to cover the EL layer 403. When light is extracted from the first electrode 401 side, the second electrode 102 corresponds to the second electrode 102. The first electrode 404 is formed of a highly reflective material. The voltage is supplied by connecting

[0179] As described above, a light-emitting device having the first electrode 401, the EL layer 403, and the second electrode 404 is provided. The lighting device described in this embodiment has a high luminous efficiency. Therefore, the lighting device in this embodiment is a lighting device with low power consumption. can be done.

[0180] The substrate 400 on which the light emitting device having the above structure is formed is sealed with a sealing substrate 407. The lighting device is completed by fixing and sealing using sealing materials 405 and 406. Either one of 405 and 406 may be used. (not shown) can also be mixed with a desiccant, which can absorb moisture. This leads to improved reliability.

[0181] In addition, a part of the pad 412 and the first electrode 401 is extended outside the sealing materials 405 and 406. By providing this, it can be used as an external input terminal. An IC chip 420 equipped with the above may be provided.

[0182] As described above, the lighting device according to the present embodiment uses the EL element according to the first and second embodiments. The light-emitting device described above is used to provide a light-emitting device with good reliability even at high temperatures. In addition, a light-emitting device with low power consumption can be provided.

[0183] (Embodiment 5) In this embodiment, the light emitting device according to the first and second embodiments is used as a part thereof. An example of an electronic device including the light-emitting device according to the first embodiment and the second embodiment will be described. The device has a long life and is a light-emitting device with good reliability even at high temperatures. The electronic device described in this embodiment has an electronic device having a light emitting portion with good reliability at high temperatures. It is possible to make it into a device.

[0184] Examples of electronic devices to which the light-emitting device is applied include television sets (televisions, (also called television receivers), computer monitors, digital cameras, digital digital video cameras, digital photo frames, mobile phones (also known as mobile phones or mobile phone devices) (hereinafter referred to as "games"), portable game machines, personal digital assistants, sound reproduction devices, large game machines such as pachinko machines Specific examples of these electronic devices are listed below.

[0185] FIG. 7A shows an example of a television device. The television device is housed in a housing 7101. A display unit 7103 is built in. In this case, the housing 71 is supported by a stand 7105. The display unit 7103 can display images. The display portion 7103 is formed using the light-emitting device described in Embodiments 1 and 2. It is arranged in a risk-like pattern.

[0186] The television device can be operated using the operation switches on the housing 7101 or a separate remote control. This can be done by the remote control device 7110. This allows you to control the channel and volume, and the image displayed on the display unit 7103 In addition, the remote control operation device 7110 can be operated. A display portion 7107 for displaying information output from the

[0187] The television device is assumed to be equipped with a receiver, modem, etc. It can receive television broadcasts and can also communicate by wire or wireless via a modem. By connecting to a network, you can send and receive data in one direction (sender to receiver) or two directions (sender to receiver). It is also possible to communicate information between the recipient and the receiver, or between receivers themselves.

[0188] FIG. 7B1 shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, a keyboard, and The device includes a keyboard 7204, an external connection port 7205, a pointing device 7206, etc. The computer uses the light-emitting device according to the first and second embodiments as a matrix. The display unit 7203 is fabricated by arranging the components in a pixel-like manner. The computer may have a form as shown in FIG. 7B2. 7204, a second display unit 7210 is provided instead of the pointing device 7206. The second display portion 7210 is a touch panel type. Input can be made by operating the displayed input display with your finger or a special pen. The second display unit 7210 can display not only an input display but also other images. The display unit 7203 may also be a touch panel. The screen may be scratched or damaged when stored or transported. It is also possible to prevent trouble from occurring.

[0189] FIG. 7C shows an example of a mobile terminal. The mobile phone has a display built into a housing 7401. In addition to the display unit 7402, there are also operation buttons 7403, an external connection port 7404, a speaker 7405, The mobile phone is equipped with a microphone 7406 and the like. 7. A display portion 7402 is provided in which the light-emitting devices according to claim 2 are arranged in a matrix. do.

[0190] The mobile terminal shown in FIG. 7C allows information to be input by touching the display portion 7402 with a finger or the like. In this case, you can make a call or write an email. Any operation can be performed by touching the display portion 7402 with a finger or the like.

[0191] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines two modes: display mode and input mode.

[0192] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. I wish.

[0193] In addition, the mobile terminal may include a sensor for detecting tilt, such as a gyro or acceleration sensor. By providing a device, the orientation of the mobile terminal (portrait or landscape) can be determined and the screen display of the display portion 7402 can be displayed. The display can be switched automatically.

[0194] The screen mode can be switched by touching the display portion 7402 or by operating the housing 7401. This is done by operating the button 7403. Also, depending on the type of image displayed on the display unit 7402, For example, if the image signal to be displayed on the display unit is a video signal, If it is data, the display mode is switched to, and if it is text data, the input mode is switched to.

[0195] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays it. If there is no input by touch operation on the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0196] The display portion 7402 can also function as an image sensor. By touching the device with your palm or fingers and capturing an image of your palm print or fingerprint, you can authenticate your identity. In addition, a backlight that emits near-infrared light to the display unit or a sensing light that emits near-infrared light By using a source, it is also possible to image finger veins, palm veins, etc.

[0197] Note that the structure described in this embodiment mode may be obtained by appropriately combining the structures described in any of Embodiment Modes 1 to 4. They can be used in combination.

[0198] As described above, the light emitting device according to the first and second embodiments can be applied to the light emitting apparatus. The range of applications is extremely wide, and this light-emitting device can be applied to electronic devices in a wide range of fields. By using the light-emitting devices according to the first and second embodiments, Therefore, it is possible to obtain highly reliable electronic equipment.

[0199] FIG. 8A is a schematic diagram showing an example of a cleaning robot.

[0200] The cleaning robot 5100 has a display 5101 on the top surface and multiple The camera 5102, the brush 5103, and the operation button 5104 are also shown. However, the underside of the cleaning robot 5100 is provided with tires, a suction port, etc. The robot 5100 also has an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, It is equipped with various sensors such as a sensor, a light sensor, and a gyro sensor. 100 is equipped with wireless communication means.

[0201] The cleaning robot 5100 moves by itself, detects the dust 5120, and sucks it out from the suction port on the bottom. It can suck up dirt.

[0202] In addition, the cleaning robot 5100 analyzes the image captured by the camera 5102 and detects the wall, furniture, or It can detect obstacles such as steps. Image analysis can also detect obstacles such as wiring. If an object that may get tangled in the brush 5103 is detected, the rotation of the brush 5103 can be stopped. can.

[0203] The display 5101 can display the remaining battery level and the amount of dust sucked. The route traveled by the cleaning robot 5100 can be displayed on the display 5101. In addition, the display 5101 is a touch panel, and the operation button 5104 is It may be provided in the ray 5101.

[0204] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. The images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the Cleaning Robot 5100 can check the status of the room even when he is away from home. In addition, the display on the display 5101 can be displayed on a mobile electronic device such as a smartphone. You can also check it out at.

[0205] The light-emitting device according to one embodiment of the present invention can be used for the display 5101 .

[0206] The robot 2100 shown in FIG. 8B includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, upper camera 2103, speaker 2104, display 2105, lower camera It is equipped with a camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0207] The microphone 2102 has a function of detecting the user's voice and environmental sounds. The speaker 2104 has a function of emitting sound. The device 2102 and the speaker 2104 can be used to communicate with the user. It is possible.

[0208] The display 2105 has the function of displaying various information. Any information desired by the user can be displayed on the display 2105. The display 2105 may be equipped with a touch panel. It may be an information terminal that can be charged by placing it in a fixed position on the robot 2100. and enables data transfer.

[0209] The upper camera 2103 and the lower camera 2106 are used to capture images of the surroundings of the robot 2100. The obstacle sensor 2107 detects the obstacles in the robot 210 by using the moving mechanism 2108. When moving forward, the robot can sense whether there are any obstacles in its path. 00 uses an upper camera 2103, a lower camera 2106, and an obstacle sensor 2107. The light-emitting device according to one embodiment of the present invention can recognize the surrounding environment and move safely. It can be used for the display 2105.

[0210] FIG. 8C is a diagram showing an example of a goggle-type display. For example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, a connection Terminal 5006, sensor 5007 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance , light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage, power, radiation , flow rate, humidity, gradient, vibration, odor, or infrared measurement functions), micro The device includes a phone 5008, a display unit 5002, a support unit 5012, earphones 5013, and the like.

[0211] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the display portion 5002. .

[0212] FIG. 9 shows a configuration of the light-emitting device according to the first and second embodiments in an electric lighting device. This is an example of a desk lamp. The desk lamp shown in FIG. 9 is made up of a housing 2001 and a light source 2002. The lighting device described in Embodiment 3 may be used as the light source 2002.

[0213] FIG. 10 shows the light-emitting device according to the first and second embodiments installed in an indoor lighting device 3. 001. The light-emitting devices described in the first and second embodiments are Highly reliable light-emitting device at high temperatures, providing reliable lighting at high temperatures The light-emitting device according to the first and second embodiments can be a device. Since the area can be increased, it can be used as a large-area lighting device. The light emitting devices according to the first and second embodiments are thin, and therefore can be used for thin lighting. It can be used as a device.

[0214] The light emitting devices according to the first and second embodiments can be used for automobile windshields and windows. The present invention can also be implemented on a flash board. The light emitting device is used in an automobile windshield or dashboard. The display areas 5200 to 5203 are the light-emitting devices described in Embodiments 1 and 2. This is a display area provided using a device.

[0215] In this embodiment, the display area 5200 and the display area 5201 are provided on the windshield of a car. 1 and 2. In the light-emitting device described in the second embodiment, the anode and the cathode are made of light-transmitting electrodes. This allows the display device to be in a see-through state, where the other side can be seen through. Yes, if the display is see-through, it can be installed on the windshield of a car. It can be installed without obstructing the view. When a transistor is provided, an organic transistor made of an organic semiconductor material or a transistor made of an oxide semiconductor may be used. A light-transmitting transistor such as a transistor is preferably used.

[0216] The display area 5202 is the display device described in Embodiments 1 and 2 provided in the pillar portion. The display device is equipped with an optical device. The display area 5202 is equipped with an imaging device mounted on the vehicle body. By projecting images from the steps, it is possible to compensate for the view obstructed by the pillars. Similarly, the display area 5203 provided on the dashboard is not blocked by the vehicle body. By projecting images from an imaging device installed outside the vehicle, the driver can see the blind spots. By projecting images to complement the invisible parts, safety can be improved. This allows the driver to check for safety more naturally and without any discomfort.

[0217] The display area 5203 displays navigation information, speedometer, RPM, mileage, fuel gauge, and gear status. By displaying the air conditioning settings, various information can be provided to the user. You can change the display items and layout as needed to suit your preferences. Information can also be provided in display areas 5200 to 5202. The display areas 5200 to 5203 can also be used as lighting devices.

[0218] 12A and 12B show a foldable mobile information terminal 5150. The portable information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 5153. FIG. 12A shows the mobile information terminal 5150 in an unfolded state. The mobile information terminal 5150 is shown in a folded state. The mobile information terminal 5150 has a large display area 5152. Despite its size, it is compact and highly portable when folded.

[0219] The display area 5152 can be folded in half by the bend 5153. 3 is composed of an expandable member and multiple support members, and when folding, The bent portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more. It can be folded.

[0220] The display area 5152 is a touch panel (input / output) equipped with a touch sensor (input device). The light-emitting device of one embodiment of the present invention can be used in the display region 5152. Cut.

[0221] 13A to 13C show a foldable mobile information terminal 9310. 13B shows the portable information terminal 9310 in an unfolded state. 13C shows the mobile information terminal 9310 in a state in which it is changing from one of the states to the other. The portable information terminal 9310 is shown in a folded state. When unfolded, it is highly portable, and when unfolded, it has a seamless, large display area that allows you to see the entire display. Excellent visibility.

[0222] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). The display panel 9311 may be a display panel (input / output device). The two housings 9315 are bent to open the mobile information terminal 9310. The light-emitting device of one embodiment of the present invention can be reversibly transformed from a folded state to a folded state. It can be used for the display panel 9311. [Example]

[0223] In this example, 2,9-di(1,3-dimethyl-2,4-diphenyl-2,4-dimethyl-1,3-dimethyl ... Synthesis of 2αN-αNPhA The structural formula of 2αN-αNPhA is shown below.

[0224] [ka]

[0225] Place 2-chloro-9-(1-naphthyl)-10-phenylanthracene in a 200 mL three-neck flask. Sen 1.1g (2.7mmol), 1-naphthylboronic acid 0.93g (5.4mmol) , di(1-adamantyl)-n-butylphosphine 0.11 g (0.30 mmol), tripotassium phosphate 1.9g (9.0mmol), tert-butyl alcohol 0.67g ( 9.0 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. 14 mL of ethyl dimethyl ether was added and the mixture was degassed by stirring under reduced pressure. 34 mg (0.15 mmol) of palladium(II) acetate was added, and the mixture was heated at 130°C under a nitrogen stream for 1 The mixture was stirred for 2 hours.

[0226] After stirring, water was added to the mixture, and the solid obtained by suction filtration was dissolved in toluene and Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855 (same below) · Alumina · Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 540-00135 (same below)) The filtrate was concentrated and the resulting solid was analyzed by high performance liquid chromatography. The product was purified by HPLC and recrystallized from toluene to give the desired pale yellow solid. The compound was obtained in an amount of 1.0 g and a yield of 73%. The synthetic scheme of this synthesis method is shown below.

[0227] [ka]

[0228] The resulting pale yellow solid (1.0 g) was purified by train sublimation. The preparation was carried out by heating a pale yellow solid at 220°C under conditions of a pressure of 3.8 Pa and an argon flow rate of 5.0 mL / min. After purification by sublimation, 0.92 g of a pale yellow solid was obtained with a recovery rate of 92%.

[0229] Nuclear magnetic resonance spectroscopy ( 1 The results of analysis by H-NMR are shown below. Also, 1 The H-NMR charts are shown in Figures 14A and 14B. This is a chart showing an enlarged range of 7.0 ppm to 8.2 ppm. Therefore, in this example, the organic compound represented by the above structural formula (100) according to one embodiment of the present invention is It was found that the compound, 2αN-αNPhA, was obtained.

[0230] 1 H NMR(DMSO-d6,300MHz):δ=7.10(d,J=8.7Hz, 1H), 7.21(t,J=7.5Hz,1H), 7.30-7.91(m,22H), 8.05-8.10(m,2H).

[0231] Next, the absorption and emission spectra of the toluene solution of 2αN-αNPhA were measured. The results are shown in Figure 15. The absorption spectrum and emission spectrum of the thin film are shown in Figure 16. The solid thin film was prepared on a quartz substrate by vacuum deposition. was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) and the The absorption spectrum of the thin film was calculated by subtracting the spectrum measured by placing the thin film in a quartz cell. The spectra were measured using a spectrophotometer (Hitachi High-Technologies Corporation, Spectrophotometer U4100). The absorbance (-log 10 [%T / ( The emission spectrum was measured using a fluorometer (( A Hamamatsu Photonics FS920 was used.

[0232] For a toluene solution of 2αN-αNPhA, the wavelengths were 403 nm, 382 nm, 363 nm, and 310 nm. Absorption peaks are observed around 283 nm and 443 nm, and around 420 nm (excitation wavelength 3 In addition, in the solid thin film of 2αN-αNPhA, Absorption peaks were observed around 409 nm, 387 nm, 367 nm, 291 nm, and 266 nm. and emitted at around 536 nm, 498 nm, 466 nm, and 440 nm (excitation wavelength 370 nm). The peak of the light wavelength was observed.

[0233] It was confirmed that 2αN-αNPhA emitted blue light. It was also found that it can be used as a host for photoluminescent materials and fluorescent materials in the visible range. The thin film of 2αN-αNPhA is resistant to aggregation even in the atmosphere and has good morphology with little change. It was found that the film had good quality.

[0234] Next, the HOMO and LUMO levels of 2αN-αNPhA were measured by cyclic voltammetry. The calculation method is shown below. The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Corporation, 99.8%, Catalog No. 227 05-6) was used, and the supporting electrolyte was tetra-n-butylammonium perchlorate (nB u4NClO4) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target is dissolved in a solution to a concentration of 2 mmol / L. It was prepared by dissolving.

[0235] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.). The auxiliary electrode was a platinum electrode (manufactured by BAS Co., Ltd., a Pt counter electrode for VC-3 ( 5cm)) and Ag / Ag as the reference electrode. + Electrode (manufactured by BAS Co., Ltd., RE7 The measurements were carried out at room temperature (20 to 25°C). It was.

[0236] The scan rate during CV measurement was standardized to 0.1 V / sec, and the oxidation rate was measured against the reference electrode. The potential Ea [V] and reduction potential Ec [V] were measured. Ea is the midpoint potential of the oxidation-reduction wave and The potential Ec was the midpoint potential of the reduction-oxidation wave. The potential energy for the position is known to be -4.94 eV. Therefore, the HOMO level [eV] = -4.94-Ea, and the LUMO level [eV] = -4.94-E From the formula c, the HOMO level and LUMO level can be calculated.

[0237] As a result, in the measurement of the oxidation potential Ea [V] of 2αN-αNPhA, the HOMO level was - On the other hand, in the measurement of the reduction potential Ec [V], The O level was found to be -2.79 eV. [Example]

[0238] In this example, 9-(1-naphthalene)-2-methyl-2-propanol, which is an anthracene compound for a host material according to one embodiment of the present invention, was used. 2-(5-phenyl-1-naphthyl)-10-phenyl-2-anthracene (abbreviation: 2 The synthesis method of PαN-αNPhA is explained in detail. The formula is shown below.

[0239] [ka]

[0240] Place 2-chloro-9-(1-naphthyl)-10-phenylanthracene in a 200 mL three-neck flask. Sen 1.3g (3.0mmol), 2-(5-phenyl-1-naphthyl)-4,4,5, 5-tetramethyl-1,3,2-dioxaborolane 1.2 g (3.7 mmol), di(1 -adamantyl)-n-butylphosphine 0.13g (0.36mmol), tricalcium phosphate sodium 2.0 g (9.2 mmol), tert-butyl alcohol 0.68 g (9.1 mmol) mol), add 15 mL of diethylene glycol dimethyl ether, and stir under reduced pressure. To this mixture was added 37 mg (0.17 mmol) of palladium (II) acetate. The mixture was stirred at 130°C for 8 hours under a nitrogen atmosphere. After stirring, water was added to the mixture, and the precipitate The solid was collected by suction filtration. The obtained solid was purified by silica gel column chromatography ( The extract was purified by toluene:hexane = 1:4 and then further purified by high performance liquid chromatography (HPLC) The solid was recrystallized from toluene to give the desired white solid. The resulting powder was 0.95 g in a 54% yield. The synthesis scheme of this synthesis method is shown below.

[0241] [ka]

[0242] 0.95 g of the resulting white powder was purified by train sublimation. The production was carried out by heating a white powder at 275°C under the conditions of a pressure of 3.4 Pa and an argon flow rate of 10 mL / min. After heating for 18 hours, 0.72 g of pale yellow powder was obtained after purification by sublimation, with a recovery rate of 76%.

[0243] The obtained pale yellow powder was analyzed by nuclear magnetic resonance spectroscopy ( 1 The results of analysis by H-NMR are shown below. Also, 1 The H-NMR charts are shown in Figures 17A and 17B. This is a chart showing an enlarged range of 7.0 ppm to 8.5 ppm. In this example, 2PαN-αNPhA represented by the above structural formula (101) was obtained from It was found that

[0244] 1 H NMR(CD2Cl2,300MHz):δ=7.23-7.80(m, 27H) , 7.88(dd, J=9.0Hz, 0.9Hz, 1H), 7.97-8.02(m, 2 H).

[0245] Next, the absorption and emission spectra of the toluene solution of 2PαN-αNPhA were measured. The results are shown in Figures 18 and 19. The measurements were carried out in the same manner as in Example 1.

[0246] From Figure 18, absorption peaks are observed around 403 nm, 382 nm, 363 nm, and 316 nm. The emission wavelength peaks were observed around 421 nm and 443 nm (excitation wavelength 382 nm). In addition, from the results of Figure 19, the solid thin film of 2PαN-αNPhA has a peak of 405 nm and 386 Absorption peaks are observed around 430 nm, 4 An emission wavelength peak was observed around 53 nm (excitation wavelength 370 nm).

[0247] It was confirmed that 2PαN-αNPhA emitted blue light. The organic compound, 2PαN-αNPhA, can also be used as a host for luminescent materials and visible fluorescent materials. In addition, thin films of 2PαN-αNPhA are less likely to aggregate even in the atmosphere. It was found that the film had good quality with little change in morphology.

[0248] Next, the HOMO and LUMO levels of 2PαN-αNPhA were measured by cyclic voltammograms. The results are calculated based on the CV measurement. The calculation method is the same as in Example 1.

[0249] As a result, by measuring the oxidation potential Ea [V] of 2PαN-αNPhA, the HOMO level is On the other hand, the reduction potential Ec [V] was measured and found to be -5.86 eV. The MO level was found to be -2.80 eV. [Example]

[0250] In this example, the anthracene compound for a host material according to one embodiment of the present invention described in Embodiment 1 was A light-emitting device 1 using the compound as a host material will be described. An organic compound having a structure similar to the anthracene compound for the host material is used as the host material. Comparative light-emitting device 1 and comparative light-emitting device 2 are also shown. The structural formulas of the organic compounds used in 1, comparative light-emitting device 1, and comparative light-emitting device 2 are shown below. show.

[0251] [ka]

[0252] (Method for fabricating light-emitting device 1) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0253] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0254] Then, 10 -4The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0255] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N-(1,1'-biphenyl)-2-(2-methyl-2-phenyl-2-propanol)-2-one represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. -4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) and ALD -MP001Q (Breakdown Workshop Co., Ltd., Material serial number: 1S20170124) and The weight ratio was 1:0.1 (= PCBBiF:ALD-MP001Q), and the resulting mixture was 10 nm thick. A hole injection layer 111 was formed by co-evaporation.

[0256] Next, PCBBiF was deposited on the hole injection layer 111 to form a first hole transport layer 112-1. After that, a second hole transport layer 112-2 was formed by vapor deposition of a compound represented by the above structural formula (ii). N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino- p-Terphenyl (abbreviation: DBfBB1TP) was evaporated to a thickness of 10 nm to form a hole transport layer. The second hole transport layer 112-2 also functions as an electron blocking layer. do.

[0257] Next, 2,9-di(1-naphthyl)-10-phenyl represented by the above structural formula (100) Anthracene (abbreviation: 2αN-αNPhA) and the 3,10 -bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino] Naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf (IV)-02) in a weight ratio of 1:0.015 (=2αN-αNPhA:3,10PCA The light-emitting layer 113 was formed by co-evaporation to a thickness of 25 nm.

[0258] Then, on the light-emitting layer 113, 2-[3'-(dibenzothiophene)-2-(3-methyl-2-benzothiophene)-2-(2-methyl-2-benzothiophene)-2-(di ... [f,h]quinoxaline (abbreviated as 2-phenyl-4-yl)biphenyl-3-yl)dibenzo[f,h]quinoxaline mDBTBPDBq-II) was evaporated to a thickness of 15 nm, and then the 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0259] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The second electrode 102 was formed by vapor deposition, and the light-emitting device 1 of this example was fabricated.

[0260] (Method for producing comparative light-emitting device 1) Comparative light-emitting device 1 is a light-emitting device in which 2αN-αNPhA in light-emitting device 1 is replaced with a compound having the above structural formula (vi 2-(1-naphthyl)-9-(2-naphthyl)-10-phenylanthracene represented by The light-emitting device was fabricated in the same manner as in device 1, except that the ZnO (abbreviation: 2αN-βNPhA) was used instead.

[0261] (Method for producing comparative light-emitting device 2) Comparative light-emitting device 2 is a light-emitting device obtained by replacing 2αN-αNPhA in light-emitting device 1 with a compound represented by the above structural formula (v 2,10-di(1-naphthyl)-9-phenylanthracene (abbreviation: 3 The light-emitting device was fabricated in the same manner as in device 1, except that the αN-αNPhA was used instead.

[0262] The device structures of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2 are shown in the table below. To summarize.

[0263] [Table 1]

[0264] These light-emitting devices were placed in a glove box with a nitrogen atmosphere, and the light-emitting devices were placed in a large The process of sealing with a glass substrate to prevent exposure to air (applying a sealant around the element, After UV treatment during encapsulation and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The performance and reliability of the device were measured at room temperature.

[0265] The luminance-current density characteristics of light-emitting device 1, comparative light-emitting device 1, and comparative light-emitting device 2 are shown. Figure 20 shows the current efficiency vs. luminance characteristics, Figure 21 shows the luminance vs. voltage characteristics, and Figure 22 shows the current vs. voltage characteristics. The external quantum efficiency vs. luminance characteristics are shown in FIG. 23, the external quantum efficiency vs. luminance characteristics are shown in FIG. 24, and the emission spectrum is shown in FIG. 25. , 1000 cd / m for Light-Emitting Device 1, Comparative Light-Emitting Device 1, and Comparative Light-Emitting Device 2 2 The main characteristics of the area are shown in Table 2.

[0266] [Table 2]

[0267] 20 to 25 and Table 2, the light-emitting device 1 and the comparative light-emitting device 2 are Optical Device 2 was found to be a blue light-emitting device with good characteristics.

[0268] In addition, the current density is 50mA / cm 2 A graph showing the change in brightness over time when The light-emitting device 1 according to one embodiment of the present invention is a light-emitting device having a naphthyl group substituted at the β-position. Comparative light-emitting device 1 using an anthracene compound as a host material, and Anthracene having α-naphthyl groups attached to the 2nd and 10th positions and a phenyl group attached to the 9th position This light-emitting device exhibits a longer life than comparative light-emitting device 2, which uses an ethylenediamine compound as a host material. It turned out to be a chair. [Example]

[0269] In this example, the anthracene compound for a host material according to one embodiment of the present invention described in Embodiment 1 was A light-emitting device 2 using the anthracene compound according to one embodiment of the present invention will be described. Comparative light-emitting device 3, which uses an organic compound with a structure similar to that of the compound as a host material, and The same is true for the comparative light-emitting device 4. The structural formulae of the organic compounds used in Comparative Light-Emitting Device 4 are shown below.

[0270] [ka]

[0271] (Method for fabricating light-emitting device 2) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0272] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0273] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0274] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-bis) represented by the above structural formula (viii) was obtained by a vapor deposition method using resistance heating. phenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation :BBABnf) and ALD-MP001Q (Bunseki Kobo Co., Ltd., material serial number: 1 S20170124) at a weight ratio of 1:0.1 (=BBABnf:ALD-MP001 Q), a hole injection layer 111 was formed to a thickness of 10 nm by co-evaporation.

[0275] Next, BBABnf was deposited on the hole injection layer 111 to form a first hole transport layer 112-1. After that, a second hole transport layer 112-2 having a thickness of 100 nm was deposited by vapor deposition. 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbamoyl) PCzN2) was evaporated to a thickness of 10 nm to form a hole transport layer 112. The second hole transport layer 112-2 also functions as an electron blocking layer.

[0276] Next, 2,9-di(1-naphthyl)-10-phenyl represented by the above structural formula (100) Anthracene (abbreviation: 2αN-αNPhA) and the 3,10 -bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino] Naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf (IV)-02) in a weight ratio of 1:0.015 (=2αN-αNPhA:3,10PCA The light-emitting layer 113 was formed by co-evaporation to a thickness of 25 nm.

[0277] Then, on the light-emitting layer 113, 2-[3'-(dibenzothiophene)-2-(3-methyl-2-benzothiophene)-2-(2-methyl-2-benzothiophene)-2-(di ... [f,h]quinoxaline (abbreviated as 2-phenyl-4-yl)biphenyl-3-yl)dibenzo[f,h]quinoxaline mDBTBPDBq-II) was evaporated to a thickness of 15 nm, and then the 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0278] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The second electrode 102 was formed by vapor deposition, and the light-emitting device 2 of this example was fabricated.

[0279] (Method for producing comparative light-emitting device 3) Comparative light-emitting device 3 is a light-emitting device in which 2αN-αNPhA in light-emitting device 2 is replaced with a compound having the above structural formula (vi i) 2-(1-naphthyl)-9-(2-naphthyl)-10-phenylanthracene The light-emitting device was fabricated in the same manner as light-emitting device 2, except that the ZnSe was changed to ZnSe (abbreviation: 2αN-βNPhA).

[0280] (Method for producing comparative light-emitting device 4) Comparative light-emitting device 4 is a light-emitting device obtained by replacing 2αN-αNPhA in light-emitting device 2 with a compound represented by the above structural formula (x 9-(1-naphthyl)-2-(2-naphthyl)-10-phenylanthracene represented by The light-emitting device was fabricated in the same manner as light-emitting device 2, except that the NPhA was changed to 2βN-αNPhA.

[0281] The device structures of light-emitting device 2, comparative light-emitting device 3, and comparative light-emitting device 4 are shown in the table below. To summarize.

[0282] [Table 3]

[0283] These light-emitting devices were placed in a glove box with a nitrogen atmosphere, and the light-emitting devices were placed in a large The process of sealing with a glass substrate to prevent exposure to air (applying a sealant around the element, After UV treatment during encapsulation and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The performance and reliability of the device were measured at room temperature.

[0284] The luminance-current density characteristics of light-emitting device 2, comparative light-emitting device 3, and comparative light-emitting device 4 are shown. Figure 27 shows the current efficiency vs. luminance characteristics, Figure 28 shows the luminance vs. voltage characteristics, and Figure 29 shows the current vs. voltage characteristics. The external quantum efficiency vs. luminance characteristics are shown in FIG. 31, and the emission spectrum is shown in FIG. 32. , 1000 cd / m for Light-Emitting Device 2, Comparative Light-Emitting Device 3, and Comparative Light-Emitting Device 4 2 The main characteristics of the area are shown in Table 4.

[0285] [Table 4]

[0286] 27 to 32 and Table 4, the light-emitting device 2 according to one embodiment of the present invention and the comparative light-emitting device It was found that Device 3 and Comparative Light-Emitting Device 4 were blue-emitting devices with good characteristics. .

[0287] In addition, the current density is 50mA / cm 2 A graph showing the change in brightness over time when The results are shown in Figure 33. The light-emitting device 2 used an anthracene compound with a naphthyl group bonded at the β-position as a host material. The light-emitting device exhibited better characteristics than comparative light-emitting device 3 and comparative light-emitting device 4 used as the light-emitting device. [Example]

[0288] In this example, the anthracene compound for a host material according to one embodiment of the present invention described in Embodiment 1 was The light-emitting device 3 and the light-emitting device 4 using the material will be described. Comparison of anthracene compounds and organic compounds with similar structures as host materials The same is true for light-emitting device 5 to comparative light-emitting device 10. Organic Compounds Used in Optical Device 4 and Comparative Light-Emitting Devices 5 to 10 The structural formula is shown below.

[0289] [ka]

[0290] [ka]

[0291] (Method for fabricating light-emitting device 3) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0292] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0293] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0294] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-bis) represented by the above structural formula (viii) was obtained by a vapor deposition method using resistance heating. phenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation :BBABnf) and ALD-MP001Q (Bunseki Kobo Co., Ltd., material serial number: 1 S20170124) at a weight ratio of 1:0.1 (=BBABnf:ALD-MP001 Q), a hole injection layer 111 was formed to a thickness of 10 nm by co-evaporation.

[0295] Next, BBABnf was deposited on the hole injection layer 111 to form a first hole transport layer 112-1. After that, a second hole transport layer 112-2 having a thickness of 100 nm was deposited by vapor deposition. 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbamoyl) PCzN2) was evaporated to a thickness of 10 nm to form a hole transport layer 112. The second hole transport layer 112-2 also functions as an electron blocking layer.

[0296] Next, 2,9-di(1-naphthyl)-10-phenyl represented by the above structural formula (100) Anthracene (abbreviation: 2αN-αNPhA) and the 3,10 -bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino] Naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf (IV)-02) in a weight ratio of 1:0.015 (=2αN-αNPhA:3,10PCA The light-emitting layer 113 was formed by co-evaporation to a thickness of 25 nm.

[0297] Then, on the light-emitting layer 113, 2-[3'-(dibenzothiophene)-2-(3-methyl-2-benzothiophene)-2-(2-methyl-2-benzothiophene)-2-(di ... [f,h]quinoxaline (abbreviated as 2-phenyl-4-yl)biphenyl-3-yl)dibenzo[f,h]quinoxaline mDBTBPDBq-II) was evaporated to a thickness of 15 nm, and then the 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0298] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The second electrode 102 was formed by vapor deposition, and the light-emitting device 3 of this example was fabricated.

[0299] (Method for fabricating light-emitting device 4) The light-emitting device 4 is a light-emitting device 3 in which 2αN-αNPhA is replaced with a compound represented by the above structural formula (101 ) represented by 9-(1-naphthyl)-10-phenyl-2-(5-phenyl-1-naphthyl) The same as for light-emitting device 3, except that the fluorine-containing anthracene (abbreviation: 2PαN-αNPhA) was used. It was made.

[0300] (Method for producing comparative light-emitting device 5) Comparative light-emitting device 5 is a light-emitting device in which 2αN-αNPhA in light-emitting device 3 is replaced with a compound having the above structural formula (xi ) represented by 2-(1-naphthyl)-10-phenyl-9-(5-phenyl-1-naphthyl) The same as light-emitting device 3 except that the α-anthracene was replaced by 2αN-PαNPhA. It was made in.

[0301] (Method for producing comparative light-emitting device 6) Comparative light-emitting device 6 is a light-emitting device obtained by replacing 2αN-αNPhA in light-emitting device 3 with a compound represented by the above structural formula (x ii) 2-(4-methyl-1-naphthyl)-9-(1-naphthyl)-10-phenyl The other components were changed to phenylanthracene (abbreviation: 2MeαN-αNPhA), and the other components were the same as those of light-emitting device 3. was prepared in the same manner.

[0302] (Method for producing comparative light-emitting device 7) The comparative light-emitting device 7 is a light-emitting device in which 2αN-αNPhA in the light-emitting device 3 is replaced with a compound having the above structural formula (xi ii) 9-(4-methyl-1-naphthyl)-2-(1-naphthyl)-10-phenyl The other components were changed to phenylanthracene (abbreviation: 2αN-MeαNPhA), and the other components were the same as those of light-emitting device 3. was prepared in the same manner.

[0303] (Method for producing comparative light-emitting device 8) Comparative light-emitting device 8 is a light-emitting device obtained by replacing 2αN-αNPhA in light-emitting device 3 with a compound represented by the above structural formula (x 10-(4-biphenyl)-2,9-di(1-naphthyl)anthracene represented by iv) (abbreviation: 2αN-αNBPhA) was used, the light-emitting device was fabricated in the same manner as in device 3.

[0304] (Method for producing comparative light-emitting device 9) Comparative light-emitting device 9 is a light-emitting device in which 2αN-αNPhA in light-emitting device 3 is replaced with a compound having the above structural formula (xv ) represented by 2-(1-naphthyl)-10-phenyl-9-(5-trimethylsilyl-1 -naphthyl)anthracene (abbreviation: 2αN-TMSαNPhA) was used, and the other components were the luminescent devices. It was made in the same way as Chair 3.

[0305] (Method for producing comparative light-emitting device 10) Comparative light-emitting device 10 is a light-emitting device in which 2αN-αNPhA in light-emitting device 3 is replaced with a compound represented by the above structural formula ( xvi) 9-(1-naphthyl)-10-phenyl-2-(5-trimethylsilyl) The other components were changed to 2TMSαN-αNPhA. It was fabricated in the same manner as optical device 3.

[0306] Light-emitting device 3, light-emitting device 4, and comparative light-emitting devices 5 to 10 The device structure is summarized in the table below.

[0307] [Table 5]

[0308] These light-emitting devices were placed in a glove box with a nitrogen atmosphere, and the light-emitting devices were placed in a large The process of sealing with a glass substrate to prevent exposure to air (applying a sealant around the element, After UV treatment during encapsulation and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The performance and reliability of the device were measured at room temperature.

[0309] Light-emitting device 3, light-emitting device 4, and comparative light-emitting devices 5 to 10 The luminance-current density characteristics are shown in Figure 34, the current efficiency-luminance characteristics are shown in Figure 35, and the luminance-voltage characteristics are shown in Figure 3 6, current-voltage characteristics are shown in Fig. 37, external quantum efficiency-luminance characteristics are shown in Fig. 38, and emission spectrum is shown in Fig. 39. The results are shown in FIG. 39. The results are shown in FIG. 39. Comparative light-emitting device 10: 1000 cd / m 2 The main characteristics of the area are shown in Table 6.

[0310] [Table 6]

[0311] 34 to 39 and Table 6, the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting device It was found that the light-emitting devices 5 to 10 were blue light-emitting devices with good characteristics. .

[0312] In addition, the current density is 50mA / cm 2 When LT95 (time until brightness deteriorates to 97%) and LT95 (time until brightness deteriorates to 95%) are summarized in the table below.

[0313] [Table 7]

[0314] As can be seen from the table, the compounds of the present invention for use as a host material are The optical device exhibited good characteristics.

[0315] Light-emitting device 3, comparative light-emitting device 6, comparative light-emitting device 7, comparative light-emitting device 9, and Comparative light-emitting device 10 shows that the anthracene compound for the host material according to one embodiment of the present invention The bond between alkyl and alkylsilyl groups has been found to affect reliability. The influence of alkylsilyl groups is large, but on the other hand, the influence of methyl groups, despite being small, It is clear that this has a relatively large impact. [Example]

[0316] In this example, the anthracene compound for a host material according to one embodiment of the present invention described in Embodiment 1 was A light-emitting device 5 using the anthracene compound according to one embodiment of the present invention will be described. Comparative light-emitting device 11 and 2, which use an organic compound having a structure similar to that of the compound as a host material. The same is true for light-emitting device 5 and comparative light-emitting device 12. The structural formulae of the organic compounds used in the light-emitting device 1 and the comparative light-emitting device 12 are shown below.

[0317] [ka]

[0318] (Method for fabricating light-emitting device 5) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0319] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0320] Then, 10-4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0321] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-bis) represented by the above structural formula (viii) was obtained by a vapor deposition method using resistance heating. phenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation :BBABnf) and ALD-MP001Q (Bunseki Kobo Co., Ltd., material serial number: 1 S20170124) at a weight ratio of 1:0.1 (=BBABnf:ALD-MP001 Q), a hole injection layer 111 was formed to a thickness of 10 nm by co-evaporation.

[0322] Next, BBABnf was deposited on the hole injection layer 111 to form a first hole transport layer 112-1. After that, a second hole transport layer 112-2 having a thickness of 100 nm was deposited by vapor deposition. 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbamoyl) PCzN2) was evaporated to a thickness of 10 nm to form a hole transport layer 112. The second hole transport layer 112-2 also functions as an electron blocking layer.

[0323] Next, 2,9-di(1-naphthyl)-10-phenyl represented by the above structural formula (100) Anthracene (abbreviation: 2αN-αNPhA) and the 3,10 -bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino] Naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf (IV)-02) in a weight ratio of 1:0.015 (=2αN-αNPhA:3,10PCA The light-emitting layer 113 was formed by co-evaporation to a thickness of 25 nm.

[0324] Then, on the light-emitting layer 113, 2-[3'-(dibenzothiophene)-2-(3-methyl-2-benzothiophene)-2-(2-methyl-2-benzothiophene)-2-(di ... [f,h]quinoxaline (abbreviated as 2-phenyl-4-yl)biphenyl-3-yl)dibenzo[f,h]quinoxaline mDBTBPDBq-II) was evaporated to a thickness of 15 nm, and then the 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0325] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The second electrode 102 was formed by vapor deposition, and the light-emitting device 5 of this example was fabricated.

[0326] (Method for producing comparative light-emitting device 11) Comparative light-emitting device 11 is a light-emitting device in which 2αN-αNPhA in light-emitting device 5 is replaced with a compound having the above structural formula (x i) 2-(1-naphthyl)-10-phenyl-9-(5-phenyl-1-naphthyl)- The same as for light-emitting device 5, except that the ZnO was replaced by 2αN-PαNPhA. It was made for you.

[0327] (Method for producing comparative light-emitting device 12) Comparative light-emitting device 12 is a light-emitting device in which 2αN-αNPhA in light-emitting device 5 is replaced with a compound represented by the above structural formula ( xvii) represented by 2,9,10-tri(1-naphthyl)anthracene (abbreviation: αTN A) was used, and the light-emitting device was fabricated in the same manner as in the light-emitting device 5.

[0328] The device structures of the light-emitting device 5, the comparative light-emitting device 11, and the comparative light-emitting device 12 are as follows: Summarize in a table.

[0329] [Table 8]

[0330] These light-emitting devices were placed in a glove box with a nitrogen atmosphere, and the light-emitting devices were placed in a large The process of sealing with a glass substrate to prevent exposure to air (applying a sealant around the element, After UV treatment during encapsulation and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The performance and reliability of the device were measured at room temperature.

[0331] Luminance-current density characteristics of light-emitting device 5, comparative light-emitting device 11, and comparative light-emitting device 12 Figure 40 shows the current efficiency vs. luminance characteristics, Figure 41 shows the luminance vs. voltage characteristics, and Figure 42 shows the current vs. voltage characteristics. The characteristics are shown in FIG. 43, the external quantum efficiency-luminance characteristics are shown in FIG. 44, and the emission spectrum is shown in FIG. Furthermore, the 1000c of the light-emitting device 5, the comparative light-emitting device 11, and the comparative light-emitting device 12 d / m 2 The main characteristics of the area are shown in Table 9.

[0332] [Table 9]

[0333] 40 to 45 and Table 9, the light-emitting device 5 according to one embodiment of the present invention and the comparative light-emitting device It was found that the light-emitting device 11 and the comparative light-emitting device 12 were blue light-emitting devices with good characteristics. It was.

[0334] In addition, the current density is 50mA / cm 2 A graph showing the change in brightness over time when The results are shown in Figure 46. The anthracene compound for host material according to one embodiment of the present invention was used as a host material. The light-emitting device 5 used has an anthracene structure in which a naphthyl group bonded to a phenyl group is bonded to the 9-position. Comparative light-emitting device 11 using a helical compound as a host material and a compound with three naphthyl groups than comparative light-emitting device 12 using a bound anthracene compound as a host material. Good characteristics were observed.

[0335] <Reference example 1> In this reference example, the organic compound 2-(4-methyl-1- naphthyl)-9-(1-naphthyl)-10-phenylanthracene (abbreviation: 2MeαN- The synthesis method of 2MeαN-αNPhA is explained in detail below. The structural formula of 2MeαN-αNPhA is as follows: Shown below.

[0336] [ka]

[0337] Place 2-chloro-9-(1-naphthyl)-10-phenylanthracene in a 200 mL three-neck flask. Sen 1.4g (3.4mmol), 4-methyl-1-naphthylboronic acid 0.77g (4. 1 mmol), di(1-adamantyl)-n-butylphosphine 0.13 g (0.36 m mol), tripotassium phosphate 2.2g (10mmol), tert-butyl alcohol 0 Add 0.79g (11mmol) and 17mL of diethylene glycol dimethyl ether, and reduce the The mixture was degassed by stirring under pressure. To this mixture was added 41 mg (0.1 8 mmol) was added, and the mixture was stirred at 130°C for 6 hours under a nitrogen stream. Water was added to the mixture, and the aqueous layer was extracted with toluene. The obtained organic layer was washed with saturated saline, and then The organic layer was dried over magnesium sulfate, the mixture was filtered, and the filtrate was concentrated. The product was purified by silica gel column chromatography (toluene:hexane=1:9) and further purified. Recrystallization with ethyl acetate gave the target substance as a white powder in an amount of 1.1 g and a yield of 64%. The synthesis scheme in this Reference Example is shown below.

[0338] [ka]

[0339] 1.1 g of the obtained white powder was purified by train sublimation. The test was carried out for 16 hours at a pressure of 3.4 Pa, an argon flow rate of 5.0 mL / min, and a heating temperature of 240°C. After purification by sublimation, 1.0 g of yellow powder was obtained with a recovery rate of 88%.

[0340] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by H-NMR are shown below. The results showed that 2MeαN-αNPhA was obtained.

[0341] 1 H NMR (CD2Cl2, 300MHz): δ=2.64(s, 3H), 7.17- 7.52(m, 12H), 7.57-7.70(m, 7H), 8.85(d, J=8.7 Hz, 2H), 7.84(dd, J=7.8Hz, 1.5Hz, 1H), 7.96-8. 01(m, 3H).

[0342] <Reference example 2> In this reference example, the organic compound 9-(4-methyl-1- naphthyl)-2-(1-naphthyl)-10-phenylanthracene (abbreviation: 2αN-Me The synthesis method of 2αN-MeαNPhA is explained in detail below. The structural formula of 2αN-MeαNPhA is as follows: Shown below.

[0343] [ka]

[0344] In a 200 mL three-neck flask, add 2-chloro-9-(4-methyl-1-naphthyl)-10-phenyl 2.4 g (5.6 mmol) of anilanthracene, 1.7 g (10 mmol), di(1-adamantyl)-n-butylphosphine 0.20 g (0.56 mm ol), 3.6 g (17 mmol) of potassium phosphate tripotassium, 1. 2 g (17 mmol) of diethylene glycol was added to the mixture, and the atmosphere in the flask was replaced with nitrogen. 28 mL of ethanol dimethyl ether was added, and the mixture was degassed by stirring under reduced pressure. 63 mg (0.28 mmol) of palladium (II) acetate was added, and the mixture was heated at 130°C under a nitrogen stream. The mixture was stirred at room temperature for 3 hours.

[0345] After stirring, water was added to the mixture, and the mixture was filtered with suction. The solid obtained was dissolved in toluene and The filtrate was concentrated and the resulting solid was collected by high-pressure filtration. It was purified by high performance liquid chromatography (HPLC) and recrystallized from toluene. The target pale yellow solid was obtained in an amount of 2.2 g and a yield of 74%. The team is shown below.

[0346] [ka]

[0347] The resulting pale yellow solid (0.95 g) was purified by train sublimation. The purification was carried out at a pressure of 3.6 Pa, an argon flow rate of 5.0 mL / min, and a heating temperature of 230°C. After sublimation purification, 0.85 g of white powder was obtained with a recovery rate of 89%.

[0348] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by H-NMR are shown below. The results showed that 2αN-MeαNPhA was obtained.

[0349] 1 H NMR(DMSO-d6,300MHz):δ=2.76(s,3H),7.12 (d,J=7.5Hz,1H), 7.23(t,J=6.9Hz,1H), 7.29-7 .76(m,19H), 7.80(d,J=8.7Hz,1H), 7.86(d,J=8 .1Hz,1H), 7.91(d,J=8.1Hz,1H), 8.15(d,J=8.1 Hz,1H).

[0350] <Reference example 3> In this reference example, the organic compound 2-(1-naphthyl)- 10-phenyl-9-(5-phenyl-1-naphthyl)anthracene (abbreviation: 2αN-P The synthesis method of 2αN-PαNPhA is explained in detail below. The structural formula of 2αN-PαNPhA is as follows: Shown below.

[0351] [ka]

[0352] In a 50 mL three-neck flask, add 2-chloro-10-phenyl-9-(5-phenyl-1-naphthyl) anthracene 0.69 g (1.4 mmol), 1-naphthaleneboronic acid 0.48 g ( 2.8 mmol), di(1-adamantyl)-n-butylphosphine 50 mg (0.14 mmol), potassium phosphate tripotassium 0.89g (4.2mmol), tert-butyl alcohol 0.31 g (4.2 mmol) of diethanol was added, and the atmosphere in the flask was replaced with nitrogen. 7.0 mL of ethylene glycol dimethyl ether was added and the mixture was degassed by stirring under reduced pressure. To this mixture, 16 mg (0.070 mmol) of palladium(II) acetate was added and the mixture was heated under nitrogen. The mixture was stirred under an air stream at 130°C for 4 hours.

[0353] After stirring, water was added to the mixture, and the mixture was filtered with suction. The solid obtained was dissolved in toluene and The filtrate was concentrated and the resulting solid was collected by high-pressure filtration. It was purified by high performance liquid chromatography (HPLC) and recrystallized from toluene. The target pale yellow solid was obtained in an amount of 0.65 g and a yield of 79%. The scheme is shown below.

[0354] [ka]

[0355] The resulting pale yellow solid (0.65 g) was purified by train sublimation. The purification was carried out at a pressure of 3.6 Pa, an argon flow rate of 5.0 mL / min, and a heating temperature of 250°C. After purification by sublimation, 0.56 g of a pale yellow solid was obtained with a recovery rate of 86%.

[0356] Nuclear magnetic resonance spectroscopy ( 1The results of analysis by H-NMR are shown below. This result indicated that 2αN-PαNPhA was obtained.

[0357] 1 H NMR(DMSO-d6,300MHz):δ=7.10(d,J=7.5Hz, 1H), 7.25(t,J=7.5Hz,1H), 7.34-7.97(m,28H).

[0358] <Reference example 4> In this reference example, the organic compound 9-(1-naphthyl)- 10-phenyl-2-(5-trimethylsilyl-1-naphthyl)anthracene (abbreviation: 2 The synthesis method of TMSαN-αNPhA is explained in detail. The structural formula of A is shown below.

[0359] [ka]

[0360] Place 2-chloro-9-(1-naphthyl)-10-phenylanthracene in a 200 mL three-neck flask. Sen 1.2g (3.0mmol), 2-(5-trimethylsilyl-1-naphthyl)-4, 4,5,5-tetramethyl-1,3,2-dioxaborolane 1.2g (3.6mmol) , di(1-adamantyl)-n-butylphosphine 0.11 g (0.30 mmol), tripotassium phosphate 1.9g (9.1mmol), tert-butyl alcohol 0.71g ( 9.5 mmol) and 15 mL of diethylene glycol dimethyl ether were added and stirred under reduced pressure. The mixture was degassed by stirring. 38 mg (0.18 mmol) of palladium (II) acetate was added to the mixture. l) was added and stirred at 130°C for 4 hours under a nitrogen stream. After stirring, water was added to the resulting mixture. The aqueous layer was extracted with toluene. The resulting organic layer was washed with saturated saline, and then the organic layer was The mixture was filtered and the filtrate was concentrated. The product was purified by column chromatography (toluene:hexane=1:4) to give an oily product. The oily product was purified by high performance liquid chromatography (HPLC) to obtain an oily product. Methanol was added to the oily substance and the precipitated solid was collected, yielding the desired white powder. The synthesis scheme in this Reference Example is shown below.

[0361] [ka]

[0362] 0.73 g of the resulting white powder was purified by train sublimation. The manufacturing process was carried out at a pressure of 3.5 Pa, an argon flow rate of 5.0 mL / min, and a heating temperature of 230°C for 18 hours. After purification by sublimation, 0.60 g of a pale yellow powder was obtained with a recovery rate of 82%.

[0363] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by H-NMR are shown below. The results showed that 2TMSαN-αNPhA was obtained.

[0364] 1 H NMR (CD2Cl2, 300MHz): δ=0.42(s, 9H), 7.14- 7.52(m, 11H), 7.57-7.72(m, 8H), 7.78(d, J=8.7 Hz, 2H), 7.85(dd, J=8.7Hz, 1.2Hz, 1H), 7.95-8. 03(m, 3H).

[0365] <Reference example 5> In this reference example, the organic compound 2-(1-naphthyl)- 10-phenyl-9-(5-trimethylsilyl-1-naphthyl)anthracene (abbreviation: 2 The synthesis method of αN-TMSαNPhA is explained in detail. The structural formula of A is shown below.

[0366] [ka]

[0367] Place 2-chloro-9-(1-naphthyl)-10-phenylanthracene in a 300 mL recovery flask. 1.2 g (2.5 mmol) of phenylalanine, 0.86 g (5.0 mmol) of naphthalene-1-boronic acid l), di(1-adamantyl)-n-butylphosphine 90 mg (0.25 mmol), Potassium phosphate tripotassium phosphate 1.6g (7.5mmol), tert-butyl alcohol 0.56g (7.5 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. 12 mL of diethyl ether was added and the mixture was degassed by stirring under reduced pressure. Palladium (II) acetate (28 mg, 0.13 mmol) was added and the mixture was heated at 130°C under a nitrogen stream. The mixture was stirred for 6 hours.

[0368] After stirring, water was added to the mixture, and the aqueous layer of the mixture was extracted with toluene to obtain an extract solution. The organic layers were combined and washed with saturated saline. The organic layer was dried over magnesium sulfate. The mixture was gravity filtered. The filtrate was concentrated and the solid was purified by silica gel column chromatography. The residue was purified by chromatography (developing solvent: hexane:toluene=5:1) to obtain a solid. The resulting solid was purified by high performance liquid chromatography (HPLC) and further purified by hexachloroisothiazolinone. The target pale yellow solid was obtained in 1.2 g and 81% yield. The synthesis scheme in this Reference Example is shown below.

[0369] [ka]

[0370] The resulting pale yellow solid (1.2 g) was purified by train sublimation. The preparation was carried out at a pressure of 3.6 Pa, an argon flow rate of 5.0 mL / min, and a heating temperature of 240°C. After purification by sublimation, 1.1 g of a white solid was obtained with a recovery rate of 93%.

[0371] Nuclear magnetic resonance spectroscopy ( 1 The results of analysis by H-NMR are shown below. This result indicated that 2αN-TMSαNPhA was obtained.

[0372] 1 H NMR (DMSO-d6,300MHz): δ=0.48(s,9H), 7.12 -7.19(m,2H), 7.26-7.46(m,8H), 7.53-7.87(m, 14H), 8.23 ​​(d, J = 8.1 Hz, 1H).

[0373] <Reference example 6> In this reference example, the organic compound 2-(1-naphthyl)- Synthesis of 9-(2-naphthyl)-10-phenylanthracene (abbreviation: 2αN-βNPhA) The structural formula of 2αN-βNPhA is shown below.

[0374] [ka]

[0375] Place 2-chloro-9-(2-naphthyl)-10-phenylanthracene in a 200 mL recovery flask. Sen 2.1g (5.0mmol), 1-naphthylboronic acid 1.3g (7.3mmol), Di(1-adamantyl)-n-butylphosphine 0.36 g (1.0 mmol), phosphoric acid 3.2 g (15 mmol) of tripotassium chloride, 1.1 g (15 mmol) of tert-butyl alcohol ol) was added, and the atmosphere in the flask was replaced with nitrogen. 25 mL of ether was added and the mixture was degassed by stirring under reduced pressure. 0.11 g (0.50 mmol) of ammonium hydroxide was added, and the mixture was stirred at 130°C for 10 hours under a nitrogen stream. Stirred.

[0376] After stirring, toluene was added to the mixture, which was then subjected to suction filtration, and the obtained filtrate was concentrated. The solution was purified by silica gel column chromatography (eluent: hexane:toluene = 4:1). The oily product was purified by high performance liquid chromatography (HPLC). The product was purified by HCl and recrystallized from a mixed solvent of ethyl acetate and hexane. A yellow solid was obtained in an amount of 1.0 g and a yield of 40%.

[0377] [ka]

[0378] The resulting pale yellow solid (1.0 g) was purified by train sublimation. The preparation was carried out by heating a pale yellow solid at 230°C under conditions of a pressure of 3.6 Pa and an argon flow rate of 5.0 mL / min. After purification by sublimation, 0.84 g of a white solid was obtained with a recovery rate of 84%.

[0379] Nuclear magnetic resonance spectroscopy ( 1The results of the analysis by H-NMR are shown below. The results showed that 2αN-βNPhA was obtained.

[0380] 1 H NMR(DMSO-d6,300MHz):δ=7.39-7.78(m,19H ), 7.86-7.96(m,3H), 8.00-8.05(m,2H), 8.12-8 .15(m,2H).

[0381] <Reference example 7> In this reference example, the organic compound 9-(1-naphthyl)- Synthesis of 2-(2-naphthyl)-10-phenylanthracene (abbreviation: 2βN-αNPhA) The structural formula of 2βN-αNPhA is shown below.

[0382] [ka]

[0383] Place 2-chloro-9-(1-naphthyl)-10-phenylanthracene in a 200 mL recovery flask. Sen 1.4g (3.3mmol), 2-naphthylboronic acid 1.1g (6.6mmol), Di(1-adamantyl)-n-butylphosphine 0.12 g (0.34 mmol), phosphorus 2.1 g (10 mmol) of tripotassium phosphate, 0.74 g (10 mmol) of tert-butyl alcohol The mixture was then purged with nitrogen. 17 mL of ethyl ether was added and the mixture was degassed by stirring under reduced pressure. 37 mg (0.17 mmol) of sodium(II) was added, and the mixture was stirred at 130°C for 5 hours under a nitrogen stream. Stirred.

[0384] After stirring, toluene was added to the mixture, which was then subjected to suction filtration, and the obtained filtrate was concentrated. The solution was purified by silica gel column chromatography (eluent: hexane:toluene = 2:1). The product was purified by ethyl acetate / hexane and recrystallized to give the desired pale yellow solid. Obtained 1.3 g, 77% yield.

[0385] [ka]

[0386] The resulting pale yellow solid (1.3 g) was purified by train sublimation. The preparation was carried out by heating a pale yellow solid at 210°C under conditions of a pressure of 3.6 Pa and an argon flow rate of 5.0 mL / min. After purification by sublimation, 1.2 g of a pale yellow solid was obtained with a recovery rate of 93%.

[0387] Nuclear magnetic resonance spectroscopy ( 1 The results of analysis by H-NMR are shown below. This result indicated that 2βN-αNPhA was obtained.

[0388] 1 H NMR(DMSO-d6,300MHz):δ=7.04(d,J=8.4Hz, 1H), 7.29-7.94(m,22H), 7.97(s,1H), 8.15(d,J =8.1Hz,1H), 8.23(d,J=8.1Hz,1H). [Explanation of symbols]

[0389] 101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 11 2: hole transport layer, 112-1: first hole transport layer, 112-2: second hole transport layer, 11 3: light-emitting layer, 114: electron transport layer, 115: electron injection layer, 116: charge generation layer, 117: P-type layer, 118: electron relay layer, 119: electron injection buffer layer, 400: substrate, 401: First electrode, 403: EL layer, 404: second electrode, 405: sealing material, 406: seal material, 407: sealing substrate, 412: pad, 420: IC chip, 501: first electrode, 5 02: second electrode, 511: first light-emitting unit, 512: second light-emitting unit, 513 : charge generation layer, 601: drive circuit section (source line drive circuit), 602: pixel section, 603: drive driving circuit section (gate line driving circuit), 604: sealing substrate, 605: sealing material, 607: space, 608: Wiring, 609: FPC (flexible printed circuit), 610: Element substrate , 611: switching FET, 612: current control FET, 613: first electrode, 6 14: insulator, 616: EL layer, 617: second electrode, 618: light-emitting device, 951: Substrate, 952: electrode, 953: insulating layer, 954: partition layer, 955: EL layer, 956: electrode 1001: substrate, 1002: base insulating film, 1003: gate insulating film, 1006: gate electrode, 1007: gate electrode, 1008: gate electrode, 1020: first interlayer insulating film, 1 021: second interlayer insulating film, 1022: electrode, 1024W: anode, 1024R: anode, 1 024G: Anode, 1024B: Anode, 1025: Partition wall, 1028: EL layer, 1029: No. 2 electrode, 1031: sealing substrate, 1032: sealing material, 1033: transparent substrate, 1034 R: red color layer, 1034G: green color layer, 1034B: blue color layer, 1035: Black matrix, 1037: third interlayer insulating film, 1040: pixel section, 1041: drive Circuit section, 1042: Peripheral section, 2001: Housing, 2002: Light source, 2100: Robot, 2 110: arithmetic unit, 2101: illuminance sensor, 2102: microphone, 2103: upper part Camera, 2104: Speaker, 2105: Display, 2106: Lower camera, 210 7: Obstacle sensor, 2108: Moving mechanism, 3001: Lighting device, 5000: Housing, 500 1: Display unit, 5002: Display unit, 5003: Speaker, 5004: LED lamp, 500 6: Connection terminal, 5007: Sensor, 5008: Microphone, 5012: Support part, 50 13: Earphones, 5100: Cleaning robot, 5101: Display, 5102: Camera , 5103: Brush, 5104: Operation button, 5150: Mobile information terminal, 5151: Housing ,5152: Display area, 5153: Bend, 5120: Dust, 5200: Display area, 52 01: Display area, 5202: Display area, 5203: Display area, 7101: Housing, 7103 : Display unit, 7105: Stand, 7107: Display unit, 7109: Operation keys, 7110: Re Remote control unit, 7201: Main unit, 7202: Housing, 7203: Display unit, 7204: Keyboard 7205: External connection port, 7206: Pointing device, 7210: Secondary Display unit, 7401: housing, 7402: display unit, 7403: operation buttons, 7404: external Connection port, 7405: Speaker, 7406: Microphone, 9310: Portable information terminal, 931 1: Display panel, 9313: Hinge, 9315: Housing

Claims

[Claim 1] An anthracene compound represented by the following general formula (G1): [Chemical formula 1] (However, in the above general formula (G1), R １ ~R ７ each independently represents hydrogen or an aryl group having 6 to 25 carbon atoms.

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