Organic compound, light-emitting device, light-receiving device, light-emitting apparatus, light-emitting module, electronic device, and lighting device

Abstract

To provide an organic compound with high heat resistance and provide a light-emitting device that includes the organic compound and has high emission efficiency and high reliability.SOLUTION: An embodiment of an organic compound herein is a compound represented by N-[4''-(9H-carbazole-9-yl)-1,1':4',1''-terphenyl-4-yl]-N-(1,1'-biphenyl-2-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: oYGTBiF(2)).SELECTED DRAWING: None

Description

[Technical field]

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting device, a light-emitting apparatus, a light-emitting module, an electronic device, and a lighting device.

[0002] Note that one embodiment of the present invention is not limited to the above technical field. Examples of the technical field of one embodiment of the present invention include a semiconductor device, a display device, a light-emitting device, a power storage device, a memory device, an electronic device, a lighting device, an input device (e.g., a touch sensor), an input / output device (e.g., a touch panel), a driving method thereof, or a manufacturing method thereof. [Background technology]

[0003] Research and development of light-emitting devices (also called organic EL devices or organic EL elements) that utilize the organic electroluminescence (EL) phenomenon is being actively conducted. The basic structure of an organic EL device is a layer containing a light-emitting organic compound (hereinafter also referred to as the light-emitting layer) sandwiched between a pair of electrodes. By applying a voltage to this organic EL device, light can be emitted from the light-emitting organic compound.

[0004] Organic EL devices have characteristics such as the ease of being made thin and lightweight, the ability to respond quickly to input signals, and the ability to be driven by a low-voltage DC power supply, making them well suited for use as display devices.

[0005] In addition, since an organic EL device can be formed in a film shape, it is possible to obtain planar light emission. Therefore, a light-emitting device with a large area can be easily formed. This is a feature that is difficult to obtain with point light sources such as LEDs (light-emitting diodes) and linear light sources such as fluorescent lamps, so that an organic EL device is highly useful as a planar light source that can be applied to lighting devices and the like.

[0006] Patent Document 1 discloses an aromatic amine compound having high hole-transporting properties as a material that can be used in a light-emitting device. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] JP 2009-298779 A Summary of the Invention [Problem to be solved by the invention]

[0008] An object of one embodiment of the present invention is to provide a novel organic compound. Alternatively, an object of one embodiment of the present invention is to provide an organic compound having high heat resistance. Alternatively, an object of one embodiment of the present invention is to provide an organic compound having high sublimability. Alternatively, an object of one embodiment of the present invention is to provide a novel organic compound that can be used in a light-emitting device. Alternatively, an object of one embodiment of the present invention is to provide a novel organic compound that can be used as a hole-transporting material in a light-emitting device. Alternatively, an object of one embodiment of the present invention is to provide a novel organic compound that can be used as a host material in which a light-emitting substance is dispersed in a light-emitting device.

[0009] Another object of one embodiment of the present invention is to provide a light-emitting device with high emission efficiency.Another object of one embodiment of the present invention is to provide a light-emitting device with low driving voltage.Another object of one embodiment of the present invention is to provide a light-emitting device with a long lifetime.Another object of one embodiment of the present invention is to provide a light-emitting device with high heat resistance.

[0010] Note that the description of these problems does not preclude the existence of other problems. One embodiment of the present invention does not necessarily have to solve all of these problems. Problems other than these can be extracted from the description of the specification, drawings, and claims. [Means for solving the problem]

[0011] One embodiment of the present invention is an organic compound represented by general formula (G0).

[0012] [ka]

[0013] In general formula (G0), R 1 ~R 5 represents general formula (A), and the others each independently represent a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms; R 6 ~R 13 , R 21 ~R 29 , R 31 ~R 39 , and R 41 ~R 48 R each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms. 21 and R 22 may be bonded to each other to form a spiro ring.

[0014] One embodiment of the present invention is an organic compound represented by general formula (G1).

[0015] [ka]

[0016] In general formula (G1), R 2 ~R 13 , R 21 ~R 29 , R 31 ~R 39 , and R 41 ~R 48 R each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms. 21 and R 22may be bonded to each other to form a spiro ring.

[0017] In the general formula (G0) and the general formula (G1), R 35 ~R 39 It is preferable that any one of the following groups represents a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0018] In the general formula (G0) and the general formula (G1), R 21 and R 22 are preferably the same and represent an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

[0019] In the general formula (G0) and the general formula (G1), R 21 and R 22 Preferably, each of R represents a methyl group. 21 and R 22 Each of R preferably represents an unsubstituted phenyl group. 21 and R 22 are preferably bonded to each other to form a spiro ring. For example, R 21 and R 22 are each preferably a substituted or unsubstituted phenyl group, and the phenyl groups are preferably bonded to each other to form a spirobifluorene ring.

[0020] In the general formula (G0) and the general formula (G1), R 41 ~R 48 Preferably, each independently represents a hydrogen atom, a methyl group, a tert-butyl group, or a substituted or unsubstituted phenyl group.

[0021] One embodiment of the present invention is a light-emitting device, a light-receiving device, or a light-emitting and receiving device including an organic compound having any of the above structures.

[0022] One embodiment of the present invention is a light-emitting device, a light-receiving device, or a light-receiving and light-emitting device which has a layer containing an organic compound between a pair of electrodes, and the layer containing an organic compound has any of the above organic compounds.

[0023] One embodiment of the present invention is a light-emitting device that has a layer containing an organic compound between a pair of electrodes, the layer containing the organic compound has a light-emitting layer and a hole-transport layer, and at least one of the light-emitting layer and the hole-transport layer has any of the organic compounds having any of the above structures.

[0024] One embodiment of the present invention is a light-emitting device including a light-emitting device having any of the above structures and one or both of a transistor and a substrate.

[0025] One embodiment of the present invention is a light-emitting module having the above-described light-emitting device, such as a light-emitting module to which a connector such as a flexible printed circuit board (hereinafter, referred to as FPC) or a TCP (Tape Carrier Package) is attached, or a light-emitting module to which an integrated circuit (IC) is mounted by a COG (Chip On Glass) method or a COF (Chip On Film) method, etc. Note that the light-emitting module of one embodiment of the present invention may have only one of a connector and an IC, or may have both.

[0026] One embodiment of the present invention is an electronic device including the above-described light-emitting module and at least one of an antenna, a battery, a housing, a camera, a speaker, a microphone, and an operation button.

[0027] One embodiment of the present invention is a lighting device including a light-emitting device having any of the above structures and at least one of a housing, a cover, and a support base. Effect of the Invention

[0028] According to one embodiment of the present invention, a novel organic compound can be provided. According to one embodiment of the present invention, an organic compound having high heat resistance can be provided. According to one embodiment of the present invention, an organic compound having high sublimability can be provided. According to one embodiment of the present invention, a novel organic compound that can be used in a light-emitting device can be provided. According to one embodiment of the present invention, a novel organic compound that can be used as a hole-transporting material in a light-emitting device can be provided. According to one embodiment of the present invention, a novel organic compound that can be used as a host material in which a light-emitting substance is dispersed in a light-emitting device can be provided.

[0029] According to one embodiment of the present invention, a light-emitting device with high emission efficiency can be provided. According to one embodiment of the present invention, a light-emitting device with low driving voltage can be provided. According to one embodiment of the present invention, a light-emitting device with long lifetime can be provided. According to one embodiment of the present invention, a light-emitting device with high heat resistance can be provided.

[0030] Note that the description of these effects does not preclude the existence of other effects. One embodiment of the present invention does not necessarily have all of these effects. Effects other than these can be extracted from the description in the specification, drawings, and claims. [Brief description of the drawings]

[0031] [Figure 1] 1(A) to 1(D) are cross-sectional views showing an example of a light-emitting device. [Diagram 2] Fig. 2(A) is a top view showing an example of a light emitting device, and Fig. 2(B) and Fig. 2(C) are cross-sectional views showing an example of the light emitting device. [Diagram 3] 3A and 3C are cross-sectional views showing an example of a light emitting apparatus, and FIG 3B is a cross-sectional view showing an example of a light emitting device. [Figure 4] 4(A) and 4(B) are cross-sectional views showing an example of a light emitting device. [Diagram 5] Fig. 5(A) is a top view illustrating an example of a light emitting device, Fig. 5(B) is a cross-sectional view illustrating an example of a light emitting device, Fig. 5(C) and Fig. 5(D) are cross-sectional views illustrating an example of a transistor. [Figure 6] 6(A) to 6(D) are diagrams showing an example of an electronic device. [Figure 7] 7(A) to 7(F) are diagrams showing an example of an electronic device. [Figure 8] 8(A) to 8(C) are diagrams showing an example of an electronic device. [Figure 9] 9(A) to 9(E) are diagrams showing an example of an electronic device. [Figure 10] 10(A) and 10(B) are the ultraviolet-visible absorption spectrum and the emission spectrum of the organic compound represented by the structural formula (100). [Figure 11] FIG. 11 is a cross-sectional view showing a light-emitting device according to the embodiment. [Figure 12] FIG. 12 is a graph showing the luminance-current efficiency characteristics of the light-emitting device of Example 2. [Figure 13] FIG. 13 is a graph showing the voltage-luminance characteristics of the light-emitting device of Example 2. [Figure 14] FIG. 14 is a diagram showing the voltage-current characteristics of the light-emitting device of Example 2. As shown in FIG. [Figure 15] FIG. 15 is a graph showing the luminance-external quantum efficiency characteristics of the light-emitting device of Example 2. [Figure 16] FIG. 16 is a diagram showing an emission spectrum of the light-emitting device of Example 2. [Figure 17] 17(A) and 17(B) are diagrams showing the results of a reliability test of the light-emitting device of Example 2. FIG. [Figure 18] FIG. 18 is a graph showing the luminance-current efficiency characteristics of the light-emitting device of Example 3. [Figure 19] FIG. 19 is a graph showing the voltage-luminance characteristics of the light-emitting device of Example 3. [Figure 20] FIG. 20 is a diagram showing the voltage-current characteristics of the light-emitting device of Example 3. [Figure 21] FIG. 21 is a graph showing the luminance-external quantum efficiency characteristics of the light-emitting device of Example 3. [Figure 22] FIG. 22 is a diagram showing an emission spectrum of the light-emitting device of Example 3. [Diagram 23] 23(A) and 23(B) are diagrams showing the results of a reliability test of the light-emitting device of Example 3. FIG. [Figure 24] FIG. 24 is a graph showing the luminance-current efficiency characteristics of the light-emitting device of Example 4. [Diagram 25] FIG. 25 is a graph showing the voltage-luminance characteristics of the light-emitting device of Example 4. [Figure 26] FIG. 26 is a diagram showing the voltage-current characteristics of the light-emitting device of Example 4. [Figure 27] FIG. 27 is a graph showing the luminance-external quantum efficiency characteristics of the light-emitting device of Example 4. [Figure 28] FIG. 28 is a diagram showing the emission spectrum of the light-emitting device of Example 4. [Figure 29] 29(A) and 29(B) are diagrams showing the results of a reliability test of the light-emitting device of Example 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0032] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it will be easily understood by those skilled in the art that the modes and details of the present invention can be modified in various ways without departing from the spirit and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the description of the embodiments shown below.

[0033] In the configuration of the invention described below, the same parts or parts having similar functions are denoted by the same reference numerals in different drawings, and the repeated explanations are omitted. In addition, when referring to similar functions, the same hatch pattern may be used and no particular reference numeral may be used.

[0034] In addition, for ease of understanding, the position, size, range, etc. of each component shown in the drawings may not represent the actual position, size, range, etc. Therefore, the disclosed invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings.

[0035] In addition, the words "film" and "layer" can be interchanged depending on the case or situation. For example, the term "conductive layer" can be changed to the term "conductive film". Or, for example, the term "insulating film" can be changed to the term "insulating layer".

[0036] (Embodiment 1) In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0037] [Structure of an organic compound according to an embodiment of the present invention] The organic compound of one embodiment of the present invention is a tertiary amine, in which a nitrogen atom of the amine is bonded to an ortho position of a biphenyl skeleton, a fluorene skeleton, and a terphenylene skeleton, and a carbazole skeleton is bonded to the phenylene group of the terphenylene skeleton that is farthest from the nitrogen atom of the amine.

[0038] Light-emitting devices used in high-temperature environments, such as for in-vehicle use, are required to have high heat resistance. In addition, when high temperatures are applied during the manufacturing process of a product, such as a sealing process using glass frit, the light-emitting device is also required to have high heat resistance. For these reasons, materials used in light-emitting devices may be required to have a glass transition temperature (Tg) of 100° C. or higher, or even 120° C. or higher. In one embodiment of the present invention, the Tg of an organic compound can be set to 100° C. or higher, or even 120° C. or higher, so that a material suitable for a light-emitting device requiring high heat resistance can be provided. On the other hand, light-emitting devices are often manufactured by vacuum deposition. In that case, the material used in the light-emitting device needs to have both high heat resistance and high sublimation property, and the sublimation temperature is preferably 500° C. or lower, more preferably 400° C. or lower. In one embodiment of the present invention, a material having not only high heat resistance but also high sublimation property can be provided, so that a material having high productivity in terms of device manufacturing can be provided.

[0039] The organic compound of one embodiment of the present invention has high hole-transporting and electron-blocking properties. The organic compound of one embodiment of the present invention can be used as a hole-transporting material in a light-emitting device. Furthermore, the organic compound of one embodiment of the present invention can be used as a host material in which a light-emitting substance is dispersed in a light-emitting device. By using the organic compound of one embodiment of the present invention, the light-emitting efficiency and reliability of a light-emitting device can be improved.

[0040] The organic compound of one embodiment of the present invention can also be used as a carrier-transporting material (hole-transporting material) in a light-receiving device such as an organic photodiode or a light-receiving and light-receiving device that has both light-emitting and light-receiving functions.

[0041] Specifically, one embodiment of the present invention is an organic compound represented by the general formula (G0). In addition to the organic compounds having structures represented by the following general formulas, materials for light-emitting devices and materials for light-receiving devices having the same structures are also embodiments of the present invention.

[0042] [ka]

[0043] In general formula (G0), R 1 ~R 5 represents general formula (A), and the others each independently represent a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms; R 6 ~R 13 , R 21 ~R 29 , R 31 ~R 39 , and R 41 ~R 48 each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms; R 21 and R 22 may be bonded to each other to form a spiro ring.

[0044] Among the organic compounds represented by general formula (G0), the organic compounds represented by general formula (G1) are more preferable. By making the molecular structure in which a carbazolyl group is bonded to the para position of a terphenylene skeleton, the heat resistance of the organic compound can be improved compared to a molecular structure in which a carbazolyl group is bonded to the ortho position or meta position of a terphenylene skeleton.

[0045] [ka]

[0046] In general formula (G1), R 2 ~R 13 , R 21 ~R 29 , R 31 ~R 39 , and R 41 ~R 48 each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms; R 21 and R 22 may be bonded to each other to form a spiro ring.

[0047] R 35 ~R 39 It is preferable that any one of the following groups represents a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, which can enhance the heat resistance of the organic compound.

[0048] When the 9-position of the fluorenyl group is hydrogen, the acidity of the hydrogen increases, and there is a concern that the reliability of the light-emitting device may decrease. 21 and R 22 It is preferable that R represents a substituent rather than hydrogen. In consideration of the heat resistance and sublimation property of the organic compound represented by the general formula (G1), 21 and R 22Each of R preferably independently represents an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. 21 and R 22 are preferably the same and represent an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

[0049] In addition, from the viewpoint of synthesis cost, R 21 and R 22 are preferably the same.

[0050] R 21 and R 22 Each of R preferably represents a methyl group. This can enhance the sublimability of the organic compound. 21 and R 22 Each of the groups preferably represents an unsubstituted phenyl group, which can enhance the heat resistance of the organic compound.

[0051] Or, R 21 and R 22 are preferably bonded to each other to form a spiro ring in order to have high heat resistance or high reliability. For example, R 21 and R 22 are each preferably a substituted or unsubstituted phenyl group, and the phenyl groups are preferably bonded to each other to form a spirobifluorene ring.

[0052] R 41 ~R 48 In order to have high sublimability or high reliability, it is preferable that each independently represent a hydrogen atom, a methyl group, a tert-butyl group, or a substituted or unsubstituted phenyl group.

[0053] In general formulae (G0) and (G1), examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group, a 2,3-dimethylbutyl group, and an n-heptyl group.

[0054] In the general formulae (G0) and (G1), examples of the cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0055] In general formulae (G0) and (G1), examples of the substituted or unsubstituted aryl group having 6 to 13 carbon atoms include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9H-fluorenyl group, a 9,9-dimethyl-9H-fluorenyl group, and a 9,9'-spirobi[9H-fluorenyl]-yl group.

[0056] In the "substituted or unsubstituted X" (X is various rings, skeletons, groups, etc.) in the general formulae (G0) and (G1), when X has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group; a cycloalkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; and an aryl group having 6 to 13 carbon atoms, such as a phenyl group, a naphthyl group, and a biphenyl group.

[0057] Specific examples of the organic compound according to one embodiment of the present invention include the organic compounds represented by structural formulas (100) to (246). However, the present invention is not limited thereto.

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[0083] [Method for synthesizing an organic compound according to one embodiment of the present invention] Various reactions can be applied as a method for synthesizing an organic compound according to one embodiment of the present invention. A method for synthesizing an organic compound represented by General Formula (G0) is exemplified below. An example of a method for synthesizing an organic compound represented by General Formula (G1) is described below.

[0084] [ka]

[0085] In general formula (G1) and each of the subsequent synthetic schemes, R 2 ~R 13 , R 21 ~R 29 , R 31 ~R 39 , and R 41 ~R 48 R each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms. 21 and R 22may be bonded to each other to form a spiro ring.

[0086] <Synthesis method 1 of organic compound represented by general formula (G1)> The organic compound represented by the general formula (G1) can be synthesized according to the synthetic scheme (a-1) or the synthetic scheme (a-2), and the synthetic scheme (a-3).

[0087] First, as shown in the synthesis scheme (a-1), a halogenated 9-terphenyl-9H-carbazole compound (compound 3) is obtained by coupling a 9-biphenyl-9H-carbazole compound (compound 1) with a dihalogenated benzene (compound 2).

[0088] [ka]

[0089] In the synthetic scheme (a-1), X 1 ~X 3 each independently represents a halogen, a boronic acid group, an organoboron group, a triflate group, an organotin group, an organozinc group, or a magnesium halide group.

[0090] In the synthetic scheme (a-1), when the Suzuki-Miyaura coupling reaction is carried out using a palladium catalyst, X 1 represents halogen, and X 2 and X 3 One of the groups represents a boronic acid group or an organic boron group, and the other represents a halogen or a triflate group. The halogen is preferably iodine, bromine, or chlorine.

[0091] In this reaction, palladium compounds such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, and tetrakis(triphenylphosphine)palladium(0) can be used, and ligands such as tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, and tri(orthotolyl)phosphine can be used. In this reaction, organic bases such as sodium tert-butoxide, and inorganic bases such as potassium carbonate, cesium carbonate, and sodium carbonate can be used.

[0092] In the reaction, as a solvent, toluene, xylene, benzene, tetrahydrofuran, dioxane, ethanol, methanol, water, diethylene glycol dimethyl ether, ethylene glycol monomethyl ether, etc. can be used. Reagents that can be used in the reaction are not limited to these.

[0093] In the synthetic scheme (a-1), it is also possible to carry out the Migita-Kosugi-Stille coupling reaction using an organotin compound, the Kumada-Tamao-Corleau coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc.

[0094] When using the Migita-Kosugi-Stille coupling reaction, X 2 and X 3 One of the compounds represents an organotin group and the other represents a halogen. That is, one of Compound 1 and Compound 2 is an organotin compound and the other is a halide.

[0095] When using the Kumada-Tamao-Corleau coupling reaction, X 2 and X 3In the formula (I), one of the compounds 1 and 2 represents a magnesium halide group, and the other represents a halogen. That is, one of the compounds 1 and 2 is a Grignard reagent, and the other is a halide.

[0096] When using the Negishi coupling reaction, X 2 and X 3 One of the compounds represents an organozinc group and the other represents a halogen. That is, one of Compound 1 and Compound 2 is an organozinc compound and the other is a halide.

[0097] Alternatively, as shown in the synthesis scheme (a-2), a halogenated 9-terphenyl-9H-carbazole compound (compound 3) is obtained by coupling a 9-phenyl-9H-carbazole compound (compound 4) with a biphenyl compound (compound 5).

[0098] [ka]

[0099] In the synthetic scheme (a-2), X 1 , X 4 , and X 5 each independently represents a halogen, a boronic acid group, an organic boron group, a triflate group, an organic tin group, an organic zinc group, or a magnesium halide group. As the halogen, iodine, bromine, or chlorine is preferable.

[0100] In the synthetic scheme (a-2), the Suzuki-Miyaura coupling reaction using a palladium catalyst, the Migita-Kosugi-Still coupling reaction using an organotin compound, the Kumada-Tamao-Corleau coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc. can be carried out. For details on the use of these reactions, please refer to the explanation in the synthetic scheme (a-1).

[0101] Compound 3 can be used in coupling reactions in combination with various diarylamine compounds, and is an effective compound that will greatly contribute to the simplification and advancement of material development. In addition, since compound 3 contains a halogen, it can be used as a raw material not only for the amination reaction, but also for the Suzuki-Miyaura coupling reaction, Migita-Kosugi-Still coupling reaction, Kumada-Tamao-Corlew coupling reaction, Negishi coupling reaction, Ullmann reaction, etc., and can be widely applied to coupling reactions to form carbon-carbon bonds, making it an effective and useful compound.

[0102] Next, as shown in the synthetic scheme (a-3), the compound 3 obtained in the synthetic scheme (a-1) or (a-2) is coupled with a diarylamine compound (compound 6) to obtain an organic compound represented by the general formula (G1).

[0103] [ka]

[0104] In the synthetic scheme (a-3), X 1 represents a halogen. The halogen is preferably iodine, bromine or chlorine.

[0105] The synthesis scheme (a-3) can be carried out by a Buchwald-Hartwig amination reaction using a palladium catalyst. When carrying out the reaction, palladium compounds such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), and allylpalladium(II) chloride (dimer) can be used as the palladium catalyst. In addition, tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(orthotolyl)phosphine, and di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)) can be used as the ligand. In this reaction, an organic base such as sodium tert-butoxide, or an inorganic base such as potassium carbonate, cesium carbonate, or sodium carbonate can be used. In this reaction, a solvent such as toluene, xylene, benzene, tetrahydrofuran, or dioxane can be used. Note that the reagents that can be used in this reaction are not limited to these.

[0106] In addition, when the synthesis scheme (a-3) is carried out by the Ullmann reaction, the reagent that can be used includes copper or a copper compound, and the base includes an inorganic base such as potassium carbonate. In the reaction, the solvent that can be used includes 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, benzene, and the like. In the Ullmann reaction, it is preferable to use DMPU or xylene, which has a high boiling point, because the target product can be obtained in a shorter time and in a higher yield at a reaction temperature of 100°C or higher. In addition, it is more preferable to use DMPU because the reaction temperature is more preferably 150°C or higher. Note that the reagents that can be used in the reaction are not limited to these.

[0107] <Synthesis method 2 of organic compound represented by general formula (G1)> The organic compound represented by the general formula (G1) can be synthesized according to the synthesis scheme (b-1).

[0108] As shown in the synthesis scheme (b-1), an organic compound represented by the general formula (G1) can be obtained by coupling a 9-biphenyl-9H-carbazole compound (compound 7) with a triarylamine compound (compound 8).

[0109] [ka]

[0110] In the synthetic scheme (b-1), X 6 and X 7 each independently represents a halogen, a boronic acid group, an organic boron group, a triflate group, an organic tin group, an organic zinc group, or a magnesium halide group. As the halogen, chlorine, bromine, or iodine is preferable, bromine or iodine is more preferable in consideration of reactivity, and chlorine or bromine is more preferable in consideration of cost.

[0111] In the synthetic scheme (b-1), the Suzuki-Miyaura coupling reaction using a palladium catalyst, the Migita-Kosugi-Still coupling reaction using an organotin compound, the Kumada-Tamao-Corleau coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the reaction using copper or a copper compound, etc. For details on the use of these reactions, please refer to the explanation in the synthetic scheme (a-1).

[0112] <Synthesis method 3 of organic compound represented by general formula (G1)> The organic compound represented by the general formula (G1) can be synthesized according to the synthesis scheme (c-1).

[0113] As shown in the synthesis scheme (c-1), an organic compound represented by general formula (G1) can be obtained by coupling a 9-phenyl-9H-carbazole compound (compound 9) with a triarylamine compound (compound 10).

[0114] [ka]

[0115] In the synthetic scheme (c-1), X 8 and X 9 each independently represents a halogen, a boronic acid group, an organic boron group, a triflate group, an organic tin group, an organic zinc group, or a magnesium halide group. As the halogen, chlorine, bromine, or iodine is preferable, bromine or iodine is more preferable in consideration of reactivity, and chlorine or bromine is more preferable in consideration of cost.

[0116] In the synthetic scheme (c-1), the Suzuki-Miyaura coupling reaction using a palladium catalyst, the Migita-Kosugi-Still coupling reaction using an organotin compound, the Kumada-Tamao-Corleau coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the reaction using copper or a copper compound, etc. For details on the use of these reactions, please refer to the explanation in the synthetic scheme (a-1).

[0117] <Synthesis method 4 of organic compound represented by general formula (G1)> The organic compound represented by the general formula (G1) can be synthesized according to the synthesis scheme (d-1).

[0118] As shown in the synthesis scheme (d-1), a diarylamine compound (compound 13) can be obtained by coupling a 9-terphenyl-9H-carbazole compound (compound 11) with a biphenyl compound (compound 12), and then a fluorene compound (compound 14) with the compound 13 can be coupled to obtain an organic compound represented by the general formula (G1).

[0119] [ka]

[0120] In the synthetic scheme (d-1), X 10 and X 11 One of X represents an amino group, and the other represents a halogen or a triflate group. 12 represents a halogen or a triflate group. As the halogen, chlorine, bromine, or iodine is preferable, and in consideration of reactivity, bromine or iodine is more preferable, and in consideration of cost, chlorine or bromine is more preferable.

[0121] In the synthetic scheme (d-1), the Buchwald-Hartwig amination reaction using a palladium catalyst, the Ullmann reaction using copper or a copper compound, etc. can be carried out. For details on the use of these reactions, see the explanation in the synthetic scheme (a-3).

[0122] <Synthesis method 5 of organic compound represented by general formula (G1)> The organic compound represented by the general formula (G1) can be synthesized according to the synthesis scheme (e-1).

[0123] As shown in the synthesis scheme (e-1), a diarylamine compound (compound 17) can be obtained by coupling a 9-terphenyl-9H-carbazole compound (compound 15) with a fluorene compound (compound 16), and then a biphenyl compound (compound 18) with the diarylamine compound (compound 17) can be coupled to obtain an organic compound represented by general formula (G1).

[0124] [ka]

[0125] In the synthetic scheme (e-1), X 13and X 14 One of X represents an amino group, and the other represents a halogen or a triflate group. 15 represents a halogen or a triflate group. As the halogen, chlorine, bromine, or iodine is preferable, and in consideration of reactivity, bromine or iodine is more preferable, and in consideration of cost, chlorine or bromine is more preferable.

[0126] In the synthetic scheme (e-1), the Buchwald-Hartwig amination reaction using a palladium catalyst, the Ullmann reaction using copper or a copper compound, etc. can be carried out. For details on the use of these reactions, see the explanation in the synthetic scheme (a-3).

[0127] Although the synthesis method of the organic compound of one embodiment of the present invention has been described above, the present invention is not limited thereto, and the organic compound may be synthesized by another synthesis method.

[0128] The organic compound of one embodiment of the present invention has high heat resistance and sublimation property and is suitable as a material for a light-emitting device or a material for a light-receiving device. The organic compound of one embodiment of the present invention has high hole-transporting property and electron-blocking property and is suitable as a host material or a hole-transporting material in a light-emitting device. By using the organic compound of one embodiment of the present invention, the light-emitting efficiency of a light-emitting device can be increased. In addition, by using the organic compound of one embodiment of the present invention, the reliability of a light-emitting device can be increased.

[0129] This embodiment mode can be combined with other embodiment modes as appropriate. In addition, in the case where a plurality of configuration examples are shown in one embodiment mode in this specification, the configuration examples can be combined as appropriate.

[0130] (Embodiment 2) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described with reference to Fig. 1. In this embodiment, a light-emitting device that has a function of emitting visible light or near-infrared light will be described.

[0131] [Example of light-emitting device configuration] <Basic structure of light-emitting devices> 1(A) to 1(D) show an example of a light-emitting device having an EL layer between a pair of electrodes.

[0132] 1A has a structure (single structure) in which an EL layer 103 is sandwiched between a first electrode 101 and a second electrode 102. The EL layer 103 has at least a light-emitting layer.

[0133] 1B shows an example of a stacked structure of the EL layer 103. In this embodiment, a case where the first electrode 101 functions as an anode and the second electrode 102 functions as a cathode will be described as an example. The EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are stacked in this order on the first electrode 101. Each of the hole injection layer 111, the hole transport layer 112, the light-emitting layer 113, the electron transport layer 114, and the electron injection layer 115 may have a single-layer structure or a stacked structure. When the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order is reversed.

[0134] The light-emitting device may have multiple EL layers between a pair of electrodes. For example, the light-emitting device preferably has n EL layers (n is an integer of 2 or more) and has a charge generating layer 104 between the (n-1)th EL layer and the nth EL layer.

[0135] Fig. 1C shows a light-emitting device with a tandem structure having two EL layers (EL layers 103a and 103b) between a pair of electrodes, and Fig. 1D shows a light-emitting device with a tandem structure having three EL layers (EL layers 103a, 103b, and 103c).

[0136] Each of the EL layers 103a, 103b, and 103c has at least a light-emitting layer. Even when a plurality of EL layers are provided as in the tandem structure shown in Fig. 1(C) and Fig. 1(D), each EL layer can have a stacked structure similar to that of the EL layer 103 shown in Fig. 1(B). Each of the EL layers 103a, 103b, and 103c can have one or more layers selected from a hole injection layer 111, a hole transport layer 112, an electron transport layer 114, and an electron injection layer 115.

[0137] 1C has a function of injecting electrons into one of the EL layer 103a and the EL layer 103b and injecting holes into the other when a voltage is applied between the first electrode 101 and the second electrode 102. Therefore, in FIG. 1C, when a voltage is applied to the first electrode 101 so that the potential of the first electrode 101 is higher than that of the second electrode 102, electrons are injected from the charge generation layer 104 into the EL layer 103a and holes are injected into the EL layer 103b.

[0138] From the viewpoint of light extraction efficiency, the charge generation layer 104 preferably transmits visible light or near infrared light (specifically, the transmittance of the charge generation layer 104 for visible light or near infrared light is 40% or more). The charge generation layer 104 also functions even if it has a lower conductivity than the first electrode 101 and the second electrode 102.

[0139] In addition, when the EL layers are provided in contact with each other to form the same structure as the charge generation layer 104 between them, the EL layers can be provided in contact with each other without a charge generation layer therebetween. For example, when a charge generation region is formed on one surface of the EL layer, the EL layer can be provided in contact with that surface.

[0140] Tandem-structure light-emitting devices have higher current efficiency and require less current to emit light with the same brightness compared to single-structure devices, which results in a longer life for the light-emitting devices and improved reliability for light-emitting devices and electronic devices.

[0141] The light-emitting layer 113 may have a light-emitting material or a combination of a plurality of materials, and may have a structure capable of obtaining fluorescent light or phosphorescent light of a desired wavelength. The light-emitting layer 113 may have a stacked structure having different emission wavelengths. In this case, the light-emitting material and other materials used in each stacked light-emitting layer may be different materials. The EL layers 103a, 103b, and 103c shown in FIG. 1(C) and FIG. 1(D) may be configured to emit light of different wavelengths. In this case, the light-emitting material and other materials used in each light-emitting layer may be different materials. For example, in FIG. 1(C), the EL layer 103a is configured to emit red and green light, and the EL layer 103b is configured to emit blue light, so that a light-emitting device that emits white light as a whole can be obtained. One light-emitting device may have a plurality of light-emitting layers or EL layers that exhibit the same color. For example, in FIG. 1(D), the EL layer 103a is configured to emit a first blue light, the EL layer 103b is configured to emit yellow, yellow-green, or green light and red light, and the EL layer 103c is configured to emit a second blue light, whereby a light-emitting device that emits white light as a whole can be obtained.

[0142] In the light-emitting device according to one embodiment of the present invention, the light emission obtained from the EL layer may be resonated between a pair of electrodes to enhance the light emission obtained. For example, in FIG. 1B, the first electrode 101 is a reflective electrode and the second electrode 102 is a semi-transmissive and semi-reflective electrode to form a micro-optical resonator (microcavity) structure, which enhances the light emission obtained from the EL layer 103.

[0143] By applying a microcavity structure to a light-emitting device, it is possible to extract light of different wavelengths (monochromatic light) even if the device has the same EL layer. This eliminates the need to form different functional layers for each pixel (so-called separate coating) to obtain different luminescent colors. This makes it easy to achieve high definition. It can also be combined with a colored layer (color filter). Furthermore, it is possible to increase the luminescent intensity of a specific wavelength in the front direction, which can reduce power consumption.

[0144] In addition, when the first electrode 101 of the light-emitting device is a reflective electrode having a laminated structure of a conductive film having reflectivity to visible light or near infrared light and a conductive film having translucency to visible light or near infrared light, optical adjustment can be performed by controlling the film thickness of the translucent conductive film. Specifically, it is preferable to adjust the inter-electrode distance between the first electrode 101 and the second electrode 102 to be approximately mλ / 2 (where m is a natural number) for the wavelength λ of light obtained from the light-emitting layer 113.

[0145] In order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, it is preferable to adjust the optical distance from the first electrode 101 to the region (light-emitting region) in the light-emitting layer 113 where the desired light is obtained, and the optical distance from the second electrode 102 to the region (light-emitting region) in the light-emitting layer 113 where the desired light is obtained, to be approximately (2m'+1)λ / 4 (where m' is a natural number). Note that the light-emitting region here refers to the recombination region of holes and electrons in the light-emitting layer 113.

[0146] By carrying out such optical adjustment, the spectrum of the light obtained from the light emitting layer 113 can be narrowed, and light emission with good color purity can be obtained.

[0147] However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 can be strictly said to be the total thickness from the reflection area in the first electrode 101 to the reflection area in the second electrode 102. However, since it is difficult to strictly determine the reflection area in the first electrode 101 or the second electrode 102, it is assumed that the above-mentioned effect can be sufficiently obtained by assuming any position of the first electrode 101 or the second electrode 102 as the reflection area. Furthermore, the optical distance between the first electrode 101 and the light-emitting layer from which the desired light is obtained can be strictly said to be the optical distance between the reflection area in the first electrode 101 and the light-emitting area in the light-emitting layer from which the desired light is obtained. However, since it is difficult to strictly determine the reflection area in the first electrode 101 or the light-emitting area in the light-emitting layer from which the desired light is obtained, it is assumed that the above-mentioned effect can be sufficiently obtained by assuming any position of the first electrode 101 as the reflection area and any position of the light-emitting layer from which the desired light is obtained as the light-emitting area.

[0148] At least one of the first electrode 101 and the second electrode 102 is an electrode having transparency to visible light or near infrared light. The visible light or near infrared light transmittance of the electrode having transparency to visible light or near infrared light is 40% or more. When the electrode having transparency to visible light or near infrared light is the semi-transmissive / semi-reflective electrode, the visible light or near infrared light reflectance of the electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. The resistivity of these electrodes is 1×10 -2 Ωcm or less is preferable.

[0149] When the first electrode 101 or the second electrode 102 is an electrode (reflective electrode) having a reflectivity to visible light or near infrared light, the reflectance of the reflective electrode to visible light or near infrared light is set to 40% or more and 100% or less, preferably 70% or more and 100% or less. The resistivity of this electrode is 1×10 -2 Ωcm or less is preferable.

[0150] <Specific structure of light-emitting device> Next, a specific structure of the light-emitting device will be described below, using a light-emitting device having a single structure shown in FIG.

[0151] <First electrode and second electrode> As the material for forming the first electrode 101 and the second electrode 102, the following materials can be used in appropriate combination as long as the above-mentioned functions of both electrodes are satisfied. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used appropriately. Specific examples include In-Sn oxide (also called ITO), In-Si-Sn oxide (also called ITSO), In-Zn oxide, and In-W-Zn oxide. In addition, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), and neodymium (Nd), and alloys containing these in appropriate combinations can also be used. In addition, elements belonging to Group 1 or 2 of the periodic table not exemplified above (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), rare earth metals such as europium (Eu) and ytterbium (Yb), alloys containing appropriate combinations of these, graphene, etc. can be used.

[0152] When a light-emitting device having a microcavity structure is manufactured, the first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a semi-transmissive and semi-reflective electrode. Therefore, a single or multiple desired conductive materials can be used to form a single layer or a laminated layer. The second electrode 102 is formed by selecting a material in the same manner as above after the EL layer 103 is formed. These electrodes can be manufactured by sputtering or vacuum deposition.

[0153] <Hole injection layer and hole transport layer> The hole injection layer 111 is a layer that injects holes from the first electrode 101, which is an anode, to the EL layer 103, and is a layer that contains a material with high hole injection properties.

[0154] Examples of materials with high hole injection properties include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide, and phthalocyanine compounds such as phthalocyanine (abbreviation: HPc) and copper phthalocyanine (abbreviation: CuPc).

[0155] Materials with high hole injection properties include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N- Aromatic amine compounds such as (4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) can be used.

[0156] Examples of materials with high hole injection properties include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl) methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), etc. Alternatively, polymer compounds to which acids have been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), etc., can also be used.

[0157] A composite material containing a hole transport material and an acceptor material (electron accepting material) can also be used as a material with high hole injection properties. In this case, electrons are extracted from the hole transport material by the acceptor material, generating holes in the hole injection layer 111, and the holes are injected into the light emitting layer 113 via the hole transport layer 112. Note that the hole injection layer 111 may be formed as a single layer made of a composite material containing a hole transport material and an acceptor material, or may be formed by laminating the hole transport material and the acceptor material in separate layers.

[0158] The hole transport layer 112 is a layer that transports holes injected from the first electrode 101 by the hole injection layer 111 to the light emitting layer 113. The hole transport layer 112 is a layer containing a hole transport material. It is particularly preferable to use a hole transport material used for the hole transport layer 112 that has a highest occupied molecular orbital (HOMO) level that is the same as or close to the HOMO level of the hole injection layer 111.

[0159] As an acceptor material used for the hole injection layer 111, an oxide of a metal belonging to Groups 4 to 8 of the periodic table can be used. Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used. Examples of compounds having an electron-withdrawing group (halogen group or cyano group) include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), 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), etc. In particular, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, are thermally stable and preferable. In addition, radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group)[3] are preferred because they have very high electron-accepting properties. Specific examples include α,α',α''-1,2,3-cyclopropane triylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropane triylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropane triylidene tris[2,3,4,5,6-pentafluorobenzeneacetonitrile].

[0160] The hole transport material used in the hole injection layer 111 and the hole transport layer 112 is 10 -6 cm 2 A substance having a hole mobility of / Vs or more is preferable. Note that other substances can also be used as long as they have a higher hole transporting property than an electron transporting property.

[0161] The light-emitting device of one embodiment of the present invention preferably contains the organic compound of one embodiment of the present invention as a hole-transporting material used in one or both of the hole-injection layer 111 and the hole-transport layer 112. In addition, the organic compound of one embodiment of the present invention has high electron blocking properties; therefore, when used in the hole-transport layer 112, the light-emitting efficiency of the light-emitting device can be increased.

[0162] As the hole transporting material, a material having high hole transporting properties, such as a π-electron-rich heteroaromatic compound (eg, a carbazole derivative, a thiophene derivative, a furan derivative, etc.) or an aromatic amine (a compound having an aromatic amine skeleton), is preferable.

[0163] Examples of carbazole derivatives (compounds having a carbazole skeleton) include bicarbazole derivatives (for example, 3,3'-bicarbazole derivatives) and aromatic amines having a carbazolyl group.

[0164] Specific examples of bicarbazole derivatives (e.g., 3,3'-bicarbazole derivatives) include 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'-bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carbazole, 9,9'-bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole, 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), and 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: βNCCP).

[0165] Specific examples of aromatic amines having a carbazolyl group include 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-yl, and N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-yl]. PCBBiF, 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBBi1BP), N,N'-bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N',N''-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), PCzPCA1, PCzPCA2, PCzPCN1, 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,Examples of such compounds include 6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4-(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N'-bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), and 4,4',4''-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA).

[0166] In addition to the above, examples of the carbazole derivative include 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), and 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA).

[0167] Specific examples of thiophene derivatives (compounds having a thiophene skeleton) and furan derivatives (compounds having a furan skeleton) include compounds having a thiophene skeleton such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).

[0168] Specific examples of aromatic amines include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), 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-phenylamino]biphenyl (abbreviation: :BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl) N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 2,7-bis[N-(4-diphenylaminophenyl)- N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPA2SF), 4,4',4''-tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), TDATA, m-MTDATA, N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), DPAB, DNTPD, DPA3B, and the like.

[0169] As the hole transporting material, polymer compounds such as PVK, PVTPA, PTPDMA, and Poly-TPD can also be used.

[0170] The hole transporting material is not limited to the above, and various known materials can be used for the hole injection layer 111 and the hole transport layer 112 either alone or in combination.

[0171] <Light-emitting layer> The light-emitting layer 113 is a layer containing a light-emitting substance. The light-emitting layer 113 can have one or more types of light-emitting substances. As the light-emitting substance, a substance that emits light of a color such as blue, purple, blue-purple, green, yellow-green, yellow, orange, or red is appropriately used. In addition, a substance that emits near-infrared light can also be used as the light-emitting substance. By using different light-emitting substances in the multiple light-emitting layers, a configuration that emits different light colors (for example, white light emission obtained by combining light-emitting colors that are complementary to each other) can be obtained. Furthermore, one light-emitting layer may have different light-emitting substances.

[0172] The light-emitting layer 113 preferably contains one or more organic compounds (host materials, assist materials, etc.) in addition to a light-emitting substance (guest material). One or both of a hole-transporting material and an electron-transporting material described in this embodiment can be used as the one or more organic compounds. A bipolar material may be used as the one or more organic compounds.

[0173] In the case where a hole-transporting material is used for the light-emitting layer 113, the organic compound of one embodiment of the present invention is preferably used as the hole-transporting material.

[0174] The light-emitting substance that can be used for the light-emitting layer 113 is not particularly limited, and a light-emitting substance that converts singlet excitation energy into light emission in the visible light region or near-infrared light region, or a light-emitting substance that converts triplet excitation energy into light emission in the visible light region or near-infrared light region can be used.

[0175] Examples of luminescent substances that convert singlet excitation energy into luminescence include substances that emit fluorescence (fluorescent materials), such as pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives, etc. Pyrene derivatives are particularly preferred because of their high luminescence quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N, N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), etc.

[0176] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)phenyl]- N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4' -(9-Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenyl) N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), and the like can be used.

[0177] Examples of light-emitting substances that convert triplet excitation energy into light emission include substances that emit phosphorescence (phosphorescent materials) and thermally activated delayed fluorescence (TADF) materials that exhibit thermally activated delayed fluorescence.

[0178] Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), rare earth metal complexes, etc. Since each substance exhibits a different emission color (emission peak), an appropriate material is selected and used as needed.

[0179] Examples of phosphorescent materials that exhibit blue or green light and have an emission spectrum with a peak wavelength of 450 nm or more and 570 nm or less include the following substances.

[0180] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN 2 ]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [ Iridium(III) (abbreviation: Ir(iPr5btz)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: Ir(iPr5btz)3]), and other organometallic complexes with a 4H-triazole skeleton, such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: Ir(iPr5btz)3]). Organometallic complexes with a 1H-triazole skeleton, such as iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) and tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), organometallic complexes with an imidazole skeleton, such as fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]) and tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), and 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 (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ] Examples include organometallic complexes with phenylpyridine derivatives having electron-withdrawing groups as ligands, such as iridium(III) acetylacetonate (abbreviation: FIr(acac)).

[0181] Examples of phosphorescent materials that exhibit green or yellow color and have an emission spectrum with a peak wavelength of 495 nm or more and 590 nm or less include the following substances.

[0182] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [I r(tBuppm)2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN 3]phenyl-κC}iridium(III) (abbreviation: [Ir(dmppm-dmp)2(acac)]) and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]); organometallic iridium complexes having a pyrazine skeleton such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]); 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(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[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’ Organometallic iridium complexes with pyridine skeletons such as iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC], and bis(2,4-diphenyl-1,3-oxazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl]pyridinato-N,C 2’}Iridium(III) acetylacetonate (abbreviation: [Ir(p-PF-ph)2(acac)]), bis(2-phenylbenzothiazolato-N,C 2’ ) iridium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac)]), as well as rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]).

[0183] Examples of phosphorescent materials that exhibit yellow or red color and have an emission spectrum with a peak wavelength of 570 nm or more and 750 nm or less include the following substances.

[0184] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) Organometallic complexes with pyrimidine skeletons such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κN)phenyl-κC). 2O,O')iridium(III) (abbreviation: [Ir(dmdppr-P)2(dibm)]), bis{4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-dmCP)2(dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalinato-N,C 2’ ]Iridium(III) (abbreviation: [Ir(mpq)2(acac)]), (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C 2’ )iridium(III) (abbreviation: [Ir(dpq)2(acac)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), bis{4,6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 Organometallic complexes with pyrazine skeletons such as iridium(III) (abbreviation: [Ir(dmdppr-m5CP)2(dpm)]) and tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2Examples of such complexes include organometallic complexes with a pyridine skeleton, such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: [PtOEP]), and rare earth metal complexes, such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]) and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]).

[0185] As the organic compound (host material, assist material, etc.) used in the light-emitting layer 113, one or more substances having a larger energy gap than the energy gap of the light-emitting substance can be selected and used.

[0186] When the light-emitting substance used in the light-emitting layer 113 is a fluorescent material, an organic compound that has a high energy level in a singlet excited state and a low energy level in a triplet excited state is preferably used as the organic compound used in combination with the light-emitting substance.

[0187] Although some of the examples overlap with the above specific examples, specific examples of organic compounds are shown below from the viewpoint of preferable combinations with light-emitting substances (fluorescent materials, phosphorescent materials).

[0188] When the luminescent substance is a fluorescent material, examples of organic compounds that can be used in combination with the luminescent substance include condensed polycyclic aromatic compounds such as anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives.

[0189] Specific examples of organic compounds (host materials) used in combination with fluorescent materials include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), PCPN, 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA ), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-di phenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-diphenylchrysene, N,N,N',N',N'',N'',N''',N'''-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), CzPA, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl 1,2-diphenyl-4'-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), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), 5,12-diphenyltetracene, 5,12-bis(biphenyl-2-yl)tetracene, etc.

[0190] When the light-emitting substance is a phosphorescent material, an organic compound having a triplet excitation energy (energy difference between the ground state and the triplet excited state) larger than the triplet excitation energy of the light-emitting substance may be selected as the organic compound to be used in combination with the light-emitting substance.

[0191] When multiple organic compounds (e.g., a first host material and a second host material (or assist material)) are used in combination with a light-emitting substance to form an exciplex, it is preferable to use these multiple organic compounds in combination with a phosphorescent material (particularly an organometallic complex).

[0192] With such a structure, light emission using ExTET (Exciplex-Triplet Energy Transfer), which is an energy transfer from an exciplex to a light-emitting substance, can be efficiently obtained. Note that a combination of a plurality of organic compounds is preferably one that easily forms an exciplex, and it is particularly preferable to combine a compound that easily receives holes (hole-transporting material) with a compound that easily receives electrons (electron-transporting material). Note that the organic compound of one embodiment of the present invention described in Embodiment 1 is suitable as a compound that easily receives holes. Note that the materials described in this embodiment can be used as specific examples of the hole-transporting material and the electron-transporting material. With this structure, high efficiency, low-voltage operation, and a long life of a light-emitting device can be simultaneously achieved.

[0193] When the luminescent substance is a phosphorescent material, examples of organic compounds that can be used in combination with the luminescent substance include aromatic amines, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, zinc- or aluminum-based metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, and phenanthroline derivatives.

[0194] Among the above, specific examples of the aromatic amines (compounds having an aromatic amine skeleton), carbazole derivatives, dibenzothiophene derivatives (thiophene derivatives), and dibenzofuran derivatives (furan derivatives), which are organic compounds with high hole-transport properties, are the same as the specific examples of the hole-transport materials shown above.

[0195] Specific examples of zinc- or aluminum-based metal complexes, which are organic compounds with high electron transport properties, include metal complexes having a quinoline skeleton or a benzoquinoline skeleton, such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), and bis(8-quinolinolato)zinc(II) (abbreviation: Znq).

[0196] In addition, metal complexes having oxazole- or thiazole-based ligands, such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), can also be used.

[0197] Specific examples of organic compounds with high electron transport properties, such as oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, and phenanthroline derivatives, include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-8), and 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9). 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophene)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: CO11), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), mDBTBIm-II), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDB q-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II).

[0198] Specific examples of heterocyclic compounds having a diazine skeleton, a triazine skeleton, and a pyridine skeleton, which are organic compounds with high electron transport properties, include 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), and 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II). 4,6mCzP2Pm), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 2-[3'-(9,9-dimethyl mFBPTzn), 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobi(9H-fluoren)-2-yl]-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl- Examples of such compounds include 1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), and 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB).

[0199] As organic compounds with high electron transport properties, polymer compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can also be used.

[0200] A TADF material is a material that can upconvert a triplet excited state to a singlet excited state with a small amount of thermal energy (reverse intersystem crossing), and efficiently emits light (fluorescence) from the singlet excited state. Conditions for efficiently obtaining thermally activated delayed fluorescence include an energy difference between the triplet excited level and the singlet excited level of 0 eV or more and 0.2 eV or less, and preferably 0 eV or more and 0.1 eV or less. Delayed fluorescence in TADF materials refers to light emission that has a spectrum similar to that of normal fluorescence, but has a significantly long lifetime. The lifetime is approximately 10 -6 seconds or more, preferably 10 -3 More than seconds.

[0201] Examples of TADF materials include fullerene and its derivatives, acridine derivatives such as proflavine, eosin, etc. Also included are metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), etc. Examples of metal-containing porphyrins include protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (abbreviation: SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(OEP)), etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), and octaethylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP).

[0202] Other examples include 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 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 Heterocyclic compounds having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, such as bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS) and 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), can be used. Note that a substance in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded is particularly preferred because the donor property of the π-electron rich heteroaromatic ring and the acceptor property of the π-electron deficient heteroaromatic ring are both strong, and the energy difference between the singlet excited state and the triplet excited state is small.

[0203] In addition, when a TADF material is used, it can be used in combination with other organic compounds, particularly with the host material, hole transport material, and electron transport material described above.

[0204] Moreover, the above-mentioned materials can be used in combination with low molecular weight materials or high molecular weight materials to form the light emitting layer 113. Moreover, for film formation, a known method (such as a vapor deposition method, a coating method, or a printing method) can be appropriately used.

[0205] <Electron transport layer> The electron transport layer 114 is a layer that transports electrons injected from the second electrode 102 by the electron injection layer 115 to the light-emitting layer 113. The electron transport layer 114 is a layer that contains an electron transport material. The electron transport material used for the electron transport layer 114 has a concentration of 1×10 -6 cm 2 A substance having an electron mobility of 1 / Vs or more is preferable. Note that other substances can also be used as long as they have a higher electron transporting property than a hole transporting property.

[0206] Examples of the electron-transporting material that can be used include metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, and metal complexes having a thiazole skeleton, as well as materials with high electron-transporting properties, such as oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline derivatives having a quinoline ligand, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, and other π-electron-deficient heteroaromatic compounds including nitrogen-containing heteroaromatic compounds.

[0207] As specific examples of the electron transporting material, the materials listed above can be used.

[0208] <Electron injection layer> The electron injection layer 115 is a layer containing a material with high electron injection properties. The electron injection layer 115 may contain any of a variety of materials, including lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiO x ) or an alkaline earth metal, or a compound thereof, can be used. Also, a rare earth metal compound, such as erbium fluoride (ErF3), can be used. Also, an electride can be used for the electron injection layer 115. For example, an electride can be a substance in which a high concentration of electrons is added to a mixed oxide of calcium and aluminum. Note that the above-mentioned substance constituting the electron transport layer 114 can also be used.

[0209] In addition, a composite material containing an electron transporting material and a donor material (electron donor material) may be used for the electron injection layer 115. Such a composite material has excellent electron injection and transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons, and specifically, for example, the above-mentioned electron transporting material (metal complex, heteroaromatic compound, etc.) used for the electron transport layer 114 can be used. As the electron donor, any substance that exhibits electron donating properties to the organic compound may be used. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, alkali metal oxides and alkaline earth metal oxides are preferable, and examples thereof include lithium oxide, calcium oxide, and barium oxide. In addition, a Lewis base such as magnesium oxide can also be used. In addition, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0210] <Charge generation layer> In the light-emitting device shown in FIG. 1(C), the charge generation layer 104 has a function of injecting electrons into the EL layer 103a and injecting holes into the EL layer 103b when a voltage is applied between the first electrode 101 (anode) and the second electrode 102 (cathode).

[0211] The charge generating layer 104 may be configured to contain a hole transport material and an acceptor material (electron accepting material), or may be configured to contain an electron transport material and a donor material. By forming the charge generating layer 104 with such a configuration, it is possible to suppress an increase in driving voltage when an EL layer is laminated.

[0212] The hole transporting material, the acceptor material, the electron transporting material, and the donor material may each be the materials described above.

[0213] In addition, a vacuum process such as a deposition method, or a solution process such as a spin coating method or an inkjet method can be used to manufacture the light-emitting device shown in this embodiment. When a deposition method is used, a physical deposition method (PVD method) such as a sputtering method, an ion plating method, an ion beam deposition method, a molecular beam deposition method, or a vacuum deposition method, or a chemical deposition method (CVD method) can be used. In particular, the functional layers (hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer) and the charge generation layer included in the EL layer can be formed by a deposition method (vacuum deposition method, etc.), a coating method (dip coating method, die coating method, bar coating method, spin coating method, spray coating method, etc.), a printing method (inkjet method, screen (screen printing) method, offset (lithographic printing) method, flexo (relief printing) method, gravure method, microcontact method, etc.), or the like.

[0214] The materials of the functional layer and the charge generating layer constituting the EL layer 103 are not limited to the above-mentioned materials. For example, the material of the functional layer may be a polymer compound (oligomer, dendrimer, polymer, etc.), a medium molecular compound (a compound in the intermediate range between a low molecular weight and a high molecular weight: molecular weight 400 to 4000), an inorganic compound (quantum dot material, etc.), etc. may be used. Note that the quantum dot material may be a colloidal quantum dot material, an alloy type quantum dot material, a core-shell type quantum dot material, a core type quantum dot material, etc.

[0215] This embodiment mode can be combined with other embodiment modes as appropriate.

[0216] (Embodiment 3) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described with reference to FIGS.

[0217] [Light emitting device configuration example 1] Fig. 2(A) shows a top view of the light emitting device, and Fig. 2(B) and Fig. 2(C) show cross-sectional views taken along dashed lines X1-Y1 and X2-Y2 in Fig. 2(A). The light emitting device shown in Fig. 2(A) to Fig. 2(C) can be used, for example, in a lighting device. The light emitting device may be any of bottom emission, top emission, and dual emission.

[0218] The light-emitting device shown in FIG. 2B includes a substrate 490a, a substrate 490b, a conductive layer 406, a conductive layer 416, an insulating layer 405, an organic EL device 450 (a first electrode 401, an EL layer 402, and a second electrode 403), and an adhesive layer 407. The organic EL device 450 can also be called a light-emitting element, an organic EL element, a light-emitting device, or the like. The EL layer 402 preferably includes the organic compound of one embodiment of the present invention described in Embodiment 1. For example, at least one of a material of a hole-injection layer, a material of a hole-transport layer, and a host material of a light-emitting layer preferably includes the organic compound.

[0219] Organic EL device 450 has a first electrode 401 on a substrate 490a, an EL layer 402 on the first electrode 401, and a second electrode 403 on the EL layer 402. Organic EL device 450 is encapsulated by substrate 490a, adhesive layer 407, and substrate 490b.

[0220] The ends of the first electrode 401, the conductive layer 406, and the conductive layer 416 are covered with an insulating layer 405. The conductive layer 406 is electrically connected to the first electrode 401, and the conductive layer 416 is electrically connected to the second electrode 403. The conductive layer 406 covered with the insulating layer 405 via the first electrode 401 functions as an auxiliary wiring and is electrically connected to the first electrode 401. Having an auxiliary wiring electrically connected to the electrode of the organic EL device 450 is preferable because it can suppress a voltage drop caused by the resistance of the electrode. The conductive layer 406 may be provided on the first electrode 401. Also, an auxiliary wiring electrically connected to the second electrode 403 may be provided on the insulating layer 405 or the like.

[0221] The substrate 490a and the substrate 490b can each be made of glass, quartz, ceramic, sapphire, organic resin, etc. When the substrate 490a and the substrate 490b are made of a flexible material, the flexibility of the display device can be increased.

[0222] The light-emitting surface of the light-emitting device may be provided with a light extraction structure to increase the light extraction efficiency, an antistatic film to suppress the adhesion of dust, a water-repellent film to prevent the adhesion of dirt, a hard coat film to suppress the occurrence of scratches during use, an impact absorbing layer, etc.

[0223] Examples of insulating materials that can be used for the insulating layer 405 include resins such as acrylic resin and epoxy resin, and inorganic insulating materials such as silicon oxide, silicon oxynitride, silicon nitride oxide, silicon nitride, and aluminum oxide.

[0224] For the adhesive layer 407, various curing adhesives such as a photo-curing adhesive such as an ultraviolet curing adhesive, a reaction curing adhesive, a heat curing adhesive, and an anaerobic adhesive can be used. Examples of such adhesives include epoxy resin, acrylic resin, silicone resin, phenolic resin, polyimide resin, imide resin, PVC (polyvinyl chloride) resin, PVB (polyvinyl butyral) resin, and EVA (ethylene vinyl acetate) resin. In particular, a material with low moisture permeability such as epoxy resin is preferable. A two-liquid mixed resin may also be used. An adhesive sheet or the like may also be used.

[0225] The light-emitting device shown in FIG. 2C includes a barrier layer 490c, a conductive layer 406, a conductive layer 416, an insulating layer 405, an organic EL device 450, an adhesive layer 407, a barrier layer 423, and a substrate 490b.

[0226] A barrier layer 490c shown in FIG. 2C includes a substrate 420, an adhesive layer 422, and an insulating layer 424 with high barrier properties.

[0227] 2(C), an organic EL device 450 is disposed between an insulating layer 424 with high barrier properties and a barrier layer 423. Therefore, even if a resin film with relatively low waterproof properties is used for the substrate 420 and the substrate 490b, it is possible to prevent impurities such as water from entering the organic EL device and shortening its lifespan.

[0228] For the substrate 420 and the substrate 490b, for example, polyester resin such as polyethylene terephthalate (PET) or polyethylene naphthalate (PEN), polyacrylonitrile resin, acrylic resin, polyimide resin, polymethyl methacrylate resin, polycarbonate (PC) resin, polyethersulfone (PES) resin, polyamide resin (nylon, aramid, etc.), polysiloxane resin, cycloolefin resin, polystyrene resin, polyamideimide resin, polyurethane resin, polyvinyl chloride resin, polyvinylidene chloride resin, polypropylene resin, polytetrafluoroethylene (PTFE) resin, ABS resin, cellulose nanofiber, etc. For the substrate 420 and the substrate 490b, glass having a thickness sufficient to provide flexibility may be used.

[0229] The insulating layer 424 having high barrier properties is preferably an inorganic insulating film. Examples of the inorganic insulating film that can be used include a silicon nitride film, a silicon oxynitride film, a silicon oxide film, a silicon nitride oxide film, an aluminum oxide film, and an aluminum nitride film. A hafnium oxide film, an yttrium oxide film, a zirconium oxide film, a gallium oxide film, a tantalum oxide film, a magnesium oxide film, a lanthanum oxide film, a cerium oxide film, and a neodymium oxide film may also be used. Two or more of the above insulating films may be stacked.

[0230] The barrier layer 423 preferably has at least one inorganic film. For example, the barrier layer 423 may have a single layer structure of an inorganic film or a laminated structure of an inorganic film and an organic film. The inorganic insulating film is suitable as the inorganic film. The laminated structure may be, for example, a silicon oxynitride film, a silicon oxide film, an organic film, a silicon oxide film, and a silicon nitride film formed in this order. By forming the barrier layer into a laminated structure of an inorganic film and an organic film, impurities (typically, hydrogen, water, etc.) that may enter the organic EL device 450 can be suitably suppressed.

[0231] The insulating layer 424 and the organic EL device 450 having high barrier properties can be formed directly on the substrate 420 having flexibility. In this case, the adhesive layer 422 is not necessary. The insulating layer 424 and the organic EL device 450 can be formed on a hard substrate via a peeling layer and then transferred to the substrate 420. For example, the insulating layer 424 and the organic EL device 450 may be peeled off from the hard substrate by applying heat, force, laser light, or the like to the peeling layer, and then transferred to the substrate 420 by bonding the substrate 420 using the adhesive layer 422. As the peeling layer, for example, a laminated structure of inorganic films including a tungsten film and a silicon oxide film, an organic resin film such as polyimide, or the like can be used. When a hard substrate is used, the insulating layer 424 can be formed at a high temperature compared to a resin substrate, and therefore the insulating layer 424 can be made into a dense insulating film having extremely high barrier properties.

[0232] [Light-emitting device configuration example 2] A cross-sectional view of a light-emitting device is shown in Fig. 3(A) The light-emitting device shown in Fig. 3(A) is an active matrix type light-emitting device in which a transistor and a light-emitting device are electrically connected to each other.

[0233] The light-emitting device shown in FIG. 3A includes a substrate 201, a transistor 210, a light-emitting device 203R, a light-emitting device 203G, a light-emitting device 203B, a color filter 206R, a color filter 206G, a color filter 206B, a substrate 205, and the like.

[0234] In FIG. 3A, a transistor 210 is provided over a substrate 201, an insulating layer 202 is provided over the transistor 210, and light-emitting devices 203R, 203G, and 203B are provided over the insulating layer 202. In FIG.

[0235] The transistor 210 and the light emitting devices 203R, 203G, and 203B are sealed in a space 207 surrounded by the substrate 201, the substrate 205, and the adhesive layer 208. The space 207 may be, for example, a reduced pressure atmosphere, an inert atmosphere, or filled with a resin.

[0236] The light emitting device shown in FIG. 3(A) has a configuration in which one pixel has a red sub-pixel (R), a green sub-pixel (G), and a blue sub-pixel (B).

[0237] A light-emitting device according to an embodiment of the present invention has a plurality of pixels arranged in a matrix. Each pixel has one or more sub-pixels. Each sub-pixel has one light-emitting device. For example, a pixel may have three sub-pixels (e.g., three colors of R, G, and B, or three colors of yellow (Y), cyan (C), and magenta (M)) or four sub-pixels (e.g., four colors of R, G, B, and white (W), or four colors of R, G, B, and Y).

[0238] 3B shows detailed configurations of the light-emitting device 203R, the light-emitting device 203G, and the light-emitting device 203B. The light-emitting devices 203R, 203G, and 203B have a common EL layer 213 and a microcavity structure in which the optical distance between the electrodes of each light-emitting device is adjusted according to the light-emitting color of each light-emitting device. The EL layer 213 preferably contains the organic compound according to one embodiment of the present invention described in Embodiment 1. For example, it is preferable that at least one of the material of the hole injection layer, the material of the hole transport layer, and the host material of the light-emitting layer contains the organic compound.

[0239] The first electrode 211 functions as a reflective electrode, and the second electrode 215 functions as a semi-transmissive and semi-reflective electrode.

[0240] The light emitting device 203R is adjusted so that the optical distance between the first electrode 211 and the second electrode 215 is 220R so that the intensity of red light is enhanced. Similarly, the light emitting device 203G is adjusted so that the optical distance between the first electrode 211 and the second electrode 215 is 220G so that the intensity of green light is enhanced, and the light emitting device 203B is adjusted so that the optical distance between the first electrode 211 and the second electrode 215 is 220B so that the intensity of blue light is enhanced.

[0241] As shown in Fig. 3(B), in the light-emitting device 203R, the conductive layer 212R is formed on the first electrode 211, and in the light-emitting device 203G, the conductive layer 212G is formed on the first electrode 211, thereby enabling optical adjustment. Furthermore, in the light-emitting device 203B, a conductive layer having a thickness different from that of the conductive layer 212R and the conductive layer 212G may be formed on the first electrode 211 to adjust the optical distance 220B. Note that, as shown in Fig. 3(A), the ends of the first electrode 211, the conductive layer 212R, and the conductive layer 212G are covered with the insulating layer 204.

[0242] 3(A) is a top-emission type light-emitting device in which light emitted from a light-emitting device is emitted through color filters of each color formed on a substrate 205. The color filters can pass specific wavelength ranges of visible light and block specific wavelength ranges.

[0243] In the red sub-pixel (R), light emitted from the light-emitting device 203R is outputted via a red color filter 206R. As shown in Fig. 3(A), by providing a color filter 206R that transmits only light in the red wavelength range at a position overlapping the light-emitting device 203R, red light can be obtained from the light-emitting device 203R.

[0244] Similarly, in the green sub-pixel (G), light emitted from the light emitting device 203G is emitted through a green color filter 206G, and in the blue sub-pixel (B), light emitted from the light emitting device 203B is emitted through a blue color filter 206B.

[0245] The substrate 205 may be provided with a black matrix 209 (which may also be called a black layer). In this case, it is preferable that the ends of the color filters overlap with the black matrix 209. Furthermore, the color filters of each color and the black matrix 209 may be covered with an overcoat layer that transmits visible light.

[0246] The light emitting device shown in Fig. 3(C) has a configuration in which one pixel has a red subpixel (R), a green subpixel (G), a blue subpixel (B), and a white subpixel (W). In Fig. 3(C), light from the light emitting device 203W of the white subpixel (W) is emitted to the outside of the light emitting device without passing through a color filter.

[0247] The optical distance between the first electrode 211 and the second electrode 215 in the light emitting device 203W may be the same as or different from any of the light emitting devices 203R, 203G, and 203B.

[0248] For example, when the light emitted from the light-emitting device 203W is white light with a low color temperature, and the intensity of blue light is to be increased, it is preferable to make the optical distance in the light-emitting device 203W equal to the optical distance 220B in the light-emitting device 203B, as shown in Fig. 3(C). This allows the light obtained from the light-emitting device 203W to approach white light with a desired color temperature.

[0249] In Fig. 3(A), a common EL layer 213 is used for the light-emitting devices of the sub-pixels of each color, but as shown in Fig. 4(A), different EL layers may be used for the light-emitting devices of the sub-pixels of each color. The above-mentioned microcavity structure can be applied to Fig. 4(A) as well.

[0250] 4(A) shows an example in which light-emitting device 203R has EL layer 213R, light-emitting device 203G has EL layer 213G, and light-emitting device 203B has EL layer 213B. EL layers 213R, 213G, and 213B may have a common layer. For example, EL layers 213R, 213G, and 213B may have different light-emitting layer configurations, and other layers may be common layers. In FIG. 4(A), light emitted by light-emitting devices 203R, 203G, and 203B may be extracted through a color filter or may be extracted without passing through a color filter.

[0251] Although a top-emission light-emitting device is shown in FIG. 3A, a light-emitting device having a structure in which light is extracted to the substrate 201 side on which the transistor 210 is formed (bottom-emission light-emitting device) as shown in FIG. 4B is also one embodiment of the present invention.

[0252] In a bottom emission type light emitting device, it is preferable to provide color filters of each color between the substrate 201 and the light emitting device. Fig. 4(B) shows an example in which a transistor 210 is formed on the substrate 201, an insulating layer 202a is formed on the transistor 210, color filters 206R, 206G, and 206B are formed on the insulating layer 202a, an insulating layer 202b is formed on the color filters 206R, 206G, and 206B, and light emitting devices 203R, 203G, and 203B are formed on the insulating layer 202b.

[0253] In the case of a top-emission type light-emitting device, the substrate 201 can be a light-shielding substrate or a light-transmitting substrate, and the substrate 205 can be a light-transmitting substrate.

[0254] In the case of a bottom emission type light emitting device, the substrate 205 can be a light-shielding substrate or a light-transmitting substrate, and the substrate 201 can be a light-transmitting substrate.

[0255] [Light-emitting device configuration example 3] The light-emitting device of one embodiment of the present invention can be a passive matrix type or an active matrix type. An active matrix type light-emitting device will be described with reference to FIG.

[0256] Fig. 5(A) shows a top view of the light emitting device, and Fig. 5(B) shows a cross-sectional view taken along dashed line A-A' shown in Fig. 5(A).

[0257] The active matrix light emitting device shown in FIG. 5A and FIG. 5B includes a pixel portion 302, a circuit portion 303, a circuit portion 304a, and a circuit portion 304b.

[0258] Each of the circuit portion 303, the circuit portion 304a, and the circuit portion 304b can function as a scanning line driver circuit (gate driver) or a signal line driver circuit (source driver), or may be a circuit that electrically connects an external gate driver or source driver to the pixel portion 302.

[0259] A lead wiring 307 is provided on the first substrate 301. The lead wiring 307 is electrically connected to an FPC 308 that is an external input terminal. The FPC 308 transmits signals (e.g., video signals, clock signals, start signals, reset signals, etc.) and potentials from the outside to the circuit portion 303, the circuit portion 304a, and the circuit portion 304b. A printed wiring board (PWB) may be attached to the FPC 308. The configuration shown in FIGS. 5(A) and 5(B) can also be called a light-emitting module having a light-emitting device (or a light-emitting apparatus) and an FPC.

[0260] The pixel portion 302 has a plurality of pixels each having an organic EL device 317, a transistor 311, and a transistor 312. The transistor 312 is electrically connected to a first electrode 313 of the organic EL device 317. The transistor 311 functions as a switching transistor. The transistor 312 functions as a current control transistor. Note that the number of transistors included in each pixel is not particularly limited and can be appropriately provided as necessary.

[0261] The circuit portion 303 has a plurality of transistors including a transistor 309 and a transistor 310. The circuit portion 303 may be formed of a circuit including transistors of the same polarity (either N-type or P-type), or may be formed of a CMOS circuit including an N-type transistor and a P-type transistor. The circuit portion 303 may also be configured to have an external driver circuit.

[0262] The structure of the transistor included in the light-emitting device of this embodiment is not particularly limited. For example, a planar transistor, a staggered transistor, an inverted staggered transistor, or the like can be used. In addition, either a top-gate type or a bottom-gate type transistor structure may be used. Alternatively, gates may be provided above and below a semiconductor layer in which a channel is formed.

[0263] The crystallinity of a semiconductor material used in a transistor is not particularly limited, and any of an amorphous semiconductor and a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor partially having a crystalline region) may be used. The use of a crystalline semiconductor is preferable because it can suppress deterioration of transistor characteristics.

[0264] The semiconductor layer of the transistor preferably contains a metal oxide (also referred to as an oxide semiconductor). Alternatively, the semiconductor layer of the transistor may contain silicon. Examples of silicon include amorphous silicon and crystalline silicon (such as low-temperature polysilicon and single crystal silicon).

[0265] The semiconductor layer preferably contains, for example, indium, M (M is one or more selected from gallium, aluminum, silicon, boron, yttrium, tin, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium), and zinc. In particular, M is preferably one or more selected from aluminum, gallium, yttrium, and tin.

[0266] In particular, it is preferable to use an oxide containing indium (In), gallium (Ga), and zinc (Zn) (also referred to as IGZO) as the semiconductor layer.

[0267] When the semiconductor layer is an In-M-Zn oxide, the sputtering target used to deposit the In-M-Zn oxide preferably has an atomic ratio of In equal to or greater than the atomic ratio of M. Examples of atomic ratios of metal elements in such sputtering targets include In:M:Zn=1:1:1, In:M:Zn=1:1:1.2, In:M:Zn=2:1:3, In:M:Zn=3:1:2, In:M:Zn=4:2:3, In:M:Zn=4:2:4.1, In:M:Zn=5:1:6, In:M:Zn=5:1:7, In:M:Zn=5:1:8, In:M:Zn=6:1:6, In:M:Zn=5:2:5, and the like.

[0268] The transistors included in the circuit portion 303, the circuit portion 304a, and the circuit portion 304b may have the same structure or may have different structures from the transistors included in the pixel portion 302. The transistors included in the circuit portion 303, the circuit portion 304a, and the circuit portion 304b may all have the same structure or may have two or more types. Similarly, the transistors included in the pixel portion 302 may all have the same structure or may have two or more types.

[0269] An end of the first electrode 313 is covered with an insulating layer 314. For the insulating layer 314, an organic compound such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin) or an inorganic compound such as silicon oxide, silicon oxynitride, or silicon nitride can be used. The upper end or lower end of the insulating layer 314 preferably has a curved surface having a curvature. This can improve the coverage of the film formed on the insulating layer 314.

[0270] An EL layer 315 is provided over the first electrode 313, and a second electrode 316 is provided over the EL layer 315. The EL layer 315 includes a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-transport layer, an electron-injection layer, a charge-generation layer, and the like. The EL layer 315 preferably includes the organic compound of one embodiment of the present invention described in Embodiment 1. For example, at least one of a material for the hole-injection layer, a material for the hole-transport layer, and a host material for the light-emitting layer preferably includes the organic compound.

[0271] The plurality of transistors and the plurality of organic EL devices 317 are sealed by the first substrate 301, the second substrate 306, and the sealant 305. A space 318 surrounded by the first substrate 301, the second substrate 306, and the sealant 305 may be filled with an inert gas (nitrogen, argon, etc.) or an organic substance (including the sealant 305).

[0272] An epoxy resin or glass frit can be used for the sealant 305. Note that it is preferable to use a material that is as impermeable to moisture and oxygen as possible for the sealant 305. When glass frit is used as the sealant, it is preferable that the first substrate 301 and the second substrate 306 are glass substrates in terms of adhesiveness.

[0273] 5C and 5D show examples of transistors that can be used in a light-emitting device.

[0274] A transistor 320 shown in FIG. 5C includes a conductive layer 321 functioning as a gate, an insulating layer 328 functioning as a gate insulating layer, a semiconductor layer 327 having a channel formation region 327i and a pair of low-resistance regions 327n, a conductive layer 322a connected to one of the pair of low-resistance regions 327n, a conductive layer 322b connected to the other of the pair of low-resistance regions 327n, an insulating layer 325 functioning as a gate insulating layer, a conductive layer 323 functioning as a gate, and an insulating layer 324 covering the conductive layer 323. The insulating layer 328 is located between the conductive layer 321 and the channel formation region 327i. The insulating layer 325 is located between the conductive layer 323 and the channel formation region 327i. The transistor 320 is preferably covered with an insulating layer 326. The insulating layer 326 may be included as a component of the transistor 320.

[0275] The conductive layer 322a and the conductive layer 322b are each connected to the low-resistance region 327n through an opening provided in the insulating layer 324. One of the conductive layer 322a and the conductive layer 322b functions as a source, and the other functions as a drain.

[0276] The insulating layer 325 is provided to overlap at least the channel formation region 327i of the semiconductor layer 327. The insulating layer 325 may cover the top surfaces and side surfaces of the pair of low-resistance regions 327n.

[0277] 5D includes a conductive layer 331 functioning as a gate, an insulating layer 338 functioning as a gate insulating layer, a conductive layer 332a and a conductive layer 332b functioning as a source and a drain, a semiconductor layer 337, an insulating layer 335 functioning as a gate insulating layer, and a conductive layer 333 functioning as a gate. The insulating layer 338 is located between the conductive layer 331 and the semiconductor layer 337. The insulating layer 335 is located between the conductive layer 333 and the semiconductor layer 337. The transistor 330 is preferably covered with an insulating layer 334. The insulating layer 334 may be included as a component of the transistor 330.

[0278] The transistor 320 and the transistor 330 have a structure in which a semiconductor layer in which a channel is formed is sandwiched between two gates. The two gates may be connected and the same signal may be supplied to drive the transistor. Alternatively, the threshold voltage of the transistor may be controlled by supplying a potential for controlling the threshold voltage to one of the two gates and a potential for driving to the other.

[0279] It is preferable to use a material that is difficult for impurities such as water and hydrogen to diffuse into at least one insulating layer that covers the transistor. This allows the insulating layer to function as a barrier layer. With this configuration, it is possible to effectively prevent impurities from diffusing into the transistor from the outside, and to improve the reliability of the light-emitting device.

[0280] It is preferable to use an inorganic insulating film for each of the insulating layers 325, 326, 328, 334, 335, and 338. As the inorganic insulating film, for example, a silicon nitride film, a silicon oxynitride film, a silicon oxide film, a silicon nitride oxide film, an aluminum oxide film, an aluminum nitride film, or the like can be used. A hafnium oxide film, an yttrium oxide film, a zirconium oxide film, a gallium oxide film, a tantalum oxide film, a magnesium oxide film, a lanthanum oxide film, a cerium oxide film, a neodymium oxide film, or the like may also be used. Two or more of the above insulating films may also be stacked.

[0281] Materials that can be used for various conductive layers constituting the light-emitting device include metals such as aluminum, titanium, chromium, nickel, copper, yttrium, zirconium, molybdenum, silver, tantalum, and tungsten, or alloys containing these as main components. Films containing these materials can be used as a single layer or a laminated structure. For example, there are a single layer structure of an aluminum film containing silicon, a two-layer structure in which an aluminum film is laminated on a titanium film, a two-layer structure in which an aluminum film is laminated on a tungsten film, a two-layer structure in which a copper film is laminated on a copper-magnesium-aluminum alloy film, a two-layer structure in which a copper film is laminated on a titanium film, a two-layer structure in which a copper film is laminated on a tungsten film, a three-layer structure in which a titanium film or titanium nitride film is laminated on the aluminum film or copper film, and a titanium film or titanium nitride film is further formed on the aluminum film or copper film, and a three-layer structure in which a molybdenum film or molybdenum nitride film is laminated on the aluminum film or copper film, and a molybdenum film or molybdenum nitride film is further formed on the aluminum film or copper film. Alternatively, oxides such as indium oxide, tin oxide, zinc oxide, etc. may be used. Furthermore, copper containing manganese is preferably used because it enhances the controllability of the shape by etching.

[0282] This embodiment mode can be combined with other embodiment modes as appropriate.

[0283] (Embodiment 4) In this embodiment, electronic devices of one embodiment of the present invention will be described with reference to drawings.

[0284] Examples of electronic devices include television sets, computer monitors, digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), portable game machines, personal digital assistants, audio playback devices, large game machines such as pachinko machines, biometric authentication devices, and testing equipment.

[0285] The electronic device of one embodiment of the present invention has a light-emitting device of one embodiment of the present invention in a display portion, and therefore has high emission efficiency and high reliability.

[0286] The display unit of the electronic device of this embodiment can display images having a resolution of, for example, full high definition, 4K2K, 8K4K, 16K8K, or higher. The screen size of the display unit can be 20 inches or more diagonally, 30 inches or more diagonally, 50 inches or more diagonally, 60 inches or more diagonally, or 70 inches or more diagonally.

[0287] Since an electronic device according to one embodiment of the present invention has flexibility, it can be installed along a curved surface of an inner or outer wall of a house or building, or the interior or exterior of an automobile.

[0288] Further, the electronic device of one embodiment of the present invention may include a secondary battery, and it is preferable that the secondary battery be charged by using contactless power transmission.

[0289] Examples of secondary batteries include lithium ion secondary batteries such as lithium polymer batteries (lithium ion polymer batteries) that use a gel electrolyte, nickel-metal hydride batteries, nickel-cadmium batteries, organic radical batteries, lead-acid batteries, air secondary batteries, nickel-zinc batteries, and silver-zinc batteries.

[0290] The electronic device of one embodiment of the present invention may have an antenna. By receiving a signal through the antenna, images, information, or the like can be displayed on a display portion. In addition, when the electronic device has an antenna and a secondary battery, the antenna may be used for contactless power transmission.

[0291] The electronic device of this embodiment may have a sensor (including a function to measure force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays).

[0292] The electronic device of the present embodiment can have various functions, such as a function of displaying various information (still images, videos, text images, etc.) on a display unit, a touch panel function, a function of displaying a calendar, date, time, etc., a function of executing various software (programs), a wireless communication function, a function of reading out a program or data recorded on a recording medium, etc.

[0293] 6A shows an example of a television set. In a television set 7100, a display portion 7000 is incorporated in a housing 7101. Here, the housing 7101 is supported by a stand 7103.

[0294] The light-emitting device of one embodiment of the present invention can be applied to the display portion 7000.

[0295] 6A can be operated using an operation switch provided on the housing 7101 or a separate remote control 7111. Alternatively, the display portion 7000 may be provided with a touch sensor, and the television set 7100 may be operated by touching the display portion 7000 with a finger or the like. The remote control 7111 may have a display portion that displays information output from the remote control 7111. Using an operation key or a touch panel provided on the remote control 7111, the channel and volume can be operated, and an image displayed on the display portion 7000 can be controlled.

[0296] The television device 7100 includes a receiver and a modem. The receiver can receive general television broadcasts. By connecting to a wired or wireless communication network via the modem, one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers) information communication can be performed.

[0297] 6B shows an example of a laptop personal computer 7200. The laptop personal computer 7200 includes a housing 7211, a keyboard 7212, a pointing device 7213, an external connection port 7214, and the like. A display portion 7000 is incorporated in the housing 7211.

[0298] The light-emitting device of one embodiment of the present invention can be applied to the display portion 7000.

[0299] FIG. 6(C) and FIG. 6(D) show an example of digital signage.

[0300] 6C includes a housing 7301, a display portion 7000, and a speaker 7303. The digital signage 7300 may further include an LED lamp, an operation key (including a power switch or an operation switch), a connection terminal, various sensors, a microphone, and the like.

[0301] 6D shows a digital signage 7400 attached to a cylindrical pillar 7401. The digital signage 7400 has a display unit 7000 provided along the curved surface of the pillar 7401.

[0302] In FIG. 6C and FIG. 6D, the light-emitting device of one embodiment of the present invention can be applied to the display portion 7000.

[0303] The larger the display unit 7000, the more information can be provided at one time. Also, the larger the display unit 7000, the more easily it catches people's attention, which can increase the advertising effect of, for example, advertisements.

[0304] Applying a touch panel to the display unit 7000 is preferable because it not only displays images or videos on the display unit 7000 but also allows the user to intuitively operate it. Furthermore, when used for providing information such as route information or traffic information, the intuitive operation can improve usability.

[0305] 6(C) and 6(D), the digital signage 7300 or the digital signage 7400 is preferably capable of wirelessly linking with an information terminal 7311 or an information terminal 7411 such as a smartphone carried by a user. For example, advertising information displayed on the display unit 7000 can be displayed on the screen of the information terminal 7311 or the information terminal 7411. By operating the information terminal 7311 or the information terminal 7411, the display on the display unit 7000 can be switched.

[0306] In addition, a game can be executed on the digital signage 7300 or the digital signage 7400 using the screen of the information terminal 7311 or the information terminal 7411 as an operation means (controller). This allows an unspecified number of users to participate in and enjoy the game at the same time.

[0307] 7A to 7F show an example of a portable information terminal having a flexible display portion 7001. In FIG.

[0308] The display portion 7001 is manufactured using a light-emitting device according to one embodiment of the present invention. For example, a light-emitting device that can be bent with a radius of curvature of 0.01 mm to 150 mm can be used. The display portion 7001 may include a touch sensor, and a mobile information terminal can be operated by touching the display portion 7001 with a finger or the like.

[0309] An example of a foldable portable information terminal is shown in Figures 7(A) to 7(C). Figure 7(A) shows a portable information terminal 7600 in an unfolded state, Figure 7(B) shows a state in the process of changing from one of the unfolded state and the folded state to the other, and Figure 7(C) shows a folded state. The portable information terminal 7600 has excellent portability in the folded state, and has excellent viewability due to a seamless wide display area in the unfolded state.

[0310] The display unit 7001 is supported by three housings 7601 connected by hinges 7602. By bending the two housings 7601 via the hinges 7602, the portable information terminal 7600 can be reversibly transformed from an unfolded state to a folded state.

[0311] 7(D) and 7(E) show an example of a foldable portable information terminal. Fig. 7(D) shows a portable information terminal 7650 folded so that the display portion 7001 faces inward, and Fig. 7(E) shows a portable information terminal 7650 folded so that the display portion 7001 faces outward. The portable information terminal 7650 has a display portion 7001 and a non-display portion 7651. When the portable information terminal 7650 is not in use, the display portion 7001 can be prevented from becoming dirty or scratched by folding the portable information terminal 7650 so that the display portion 7001 faces inward.

[0312] 7F shows an example of a wristwatch-type portable information terminal. The portable information terminal 7800 has a band 7801, a display portion 7001, an input / output terminal 7802, operation buttons 7803, and the like. The band 7801 functions as a housing. The portable information terminal 7800 can be equipped with a flexible battery 7805. The battery 7805 may be disposed overlapping the display portion 7001 or the band 7801, for example.

[0313] The band 7801, the display portion 7001, and the battery 7805 are flexible, so that the portable information terminal 7800 can be easily curved into a desired shape.

[0314] The operation button 7803 can have various functions, such as time setting, power on / off operation, wireless communication on / off operation, silent mode activation / cancellation, power saving mode activation / cancellation, etc. For example, the function of the operation button 7803 can be freely set by an operating system built into the mobile information terminal 7800.

[0315] Moreover, by touching an icon 7804 displayed on the display unit 7001 with a finger or the like, an application can be started.

[0316] The portable information terminal 7800 is also capable of performing short-distance wireless communication according to a communication standard. For example, the portable information terminal 7800 can communicate with a wireless headset to enable hands-free calling.

[0317] The portable information terminal 7800 may also have an input / output terminal 7802. When the portable information terminal 7802 is provided, data can be directly exchanged with another information terminal through a connector. Charging can also be performed through the input / output terminal 7802. Note that the charging operation of the portable information terminal exemplified in this embodiment may be performed by non-contact power transmission without using an input / output terminal.

[0318] FIG. 8A shows the appearance of an automobile 9700. FIG. 8B shows a driver's seat of the automobile 9700. The automobile 9700 includes a body 9701, wheels 9702, a windshield 9703, a light 9704, a fog lamp 9705, and the like. The light-emitting device of one embodiment of the present invention can be used for a display portion of the automobile 9700. For example, the light-emitting device of one embodiment of the present invention can be provided for the display portions 9710 to 9715 shown in FIG. 8B. Alternatively, the light-emitting device of one embodiment of the present invention may be used for the light 9704 or the fog lamp 9705.

[0319] The display portion 9710 and the display portion 9711 are display devices provided on a windshield of an automobile. The light-emitting device of one embodiment of the present invention can be in a so-called see-through state, in which the other side can be seen through, by forming electrodes and wirings using a light-transmitting conductive material. If the display portion 9710 or the display portion 9711 is in a see-through state, the view is not obstructed even when the automobile 9700 is driven. Thus, the light-emitting device of one embodiment of the present invention can be installed on the windshield of the automobile 9700. Note that when a transistor or the like is provided to drive the light-emitting device, a light-transmitting transistor such as an organic transistor using an organic semiconductor material or a transistor using an oxide semiconductor is preferably used.

[0320] The display unit 9712 is a display device provided in the pillar portion. For example, by displaying an image from an imaging means provided in the vehicle body on the display unit 9712, the view blocked by the pillar can be complemented. The display unit 9713 is a display device provided in the dashboard portion. For example, by displaying an image from an imaging means provided in the vehicle body on the display unit 9713, the view blocked by the dashboard can be complemented. That is, by displaying an image from an imaging means provided outside the vehicle, blind spots can be complemented and safety can be improved. In addition, by displaying an image that complements the invisible parts, safety can be confirmed more naturally and without discomfort.

[0321] FIG. 8(C) shows the interior of a vehicle in which bench seats are used for the driver's seat and the passenger seat. The display unit 9721 is a display device provided in the door. For example, a view blocked by the door can be complemented by displaying an image from an imaging means provided in the vehicle body on the display unit 9721. The display unit 9722 is a display device provided in the steering wheel. The display unit 9723 is a display device provided in the center of the seat of the bench seat. Note that the display device can be installed on the seat or backrest and used as a seat heater using the heat generated by the display device as a heat source.

[0322] The display unit 9714, the display unit 9715, or the display unit 9722 can provide various information by displaying navigation information, a speedometer, a tachometer, a mileage, a fuel gauge, a gear state, air conditioning settings, and the like. In addition, the display items and layouts displayed on the display units can be changed as appropriate according to the user's preferences. Note that the above information can also be displayed on the display units 9710 to 9713, the display units 9721, and the display units 9723. In addition, the display units 9710 to 9715, and the display units 9721 to 9723 can also be used as lighting devices. In addition, the display units 9710 to 9715, and the display units 9721 to 9723 can also be used as heating devices.

[0323] Furthermore, since the electronic device according to one embodiment of the present invention has a light-emitting device according to one embodiment of the present invention as a light source, the electronic device has high emission efficiency and high reliability. For example, the light-emitting device according to one embodiment of the present invention can be used as a light source that emits visible light or near-infrared light. The light-emitting device according to one embodiment of the present invention can also be used as a light source for a lighting device.

[0324] FIG. 9(A) shows a biometric authentication device for finger veins, and includes a housing 911, a light source 912, a detection stage 913, and the like. By placing a finger on the detection stage 913, the shape of the veins can be imaged. A light source 912 that emits near-infrared light is provided on the upper part of the detection stage 913, and an imaging device 914 is provided on the lower part. The detection stage 913 is made of a material that transmits near-infrared light, and the near-infrared light that is irradiated from the light source 912 and passes through the finger can be imaged by the imaging device 914. Note that an optical system may be provided between the detection stage 913 and the imaging device 914. The above device configuration can also be used in a biometric authentication device for palm veins.

[0325] The light-emitting device of one embodiment of the present invention can be used for the light source 912. The light-emitting device of one embodiment of the present invention can be installed in a curved shape and can irradiate light uniformly to an object. In particular, the light-emitting device is preferably a light-emitting device that emits near-infrared light having the strongest peak intensity in a wavelength range of 700 nm to 1200 nm. The position of veins can be detected by receiving light that has passed through a finger, a palm, or the like and imaging it. This function can be used for biometric authentication. Furthermore, by combining with a global shutter system, highly accurate sensing is possible even if the object moves.

[0326] 9B. The light source 912 may have a plurality of light emitting units, such as light emitting units 915, 916, and 917. The light emitting units 915, 916, and 917 may emit light having different wavelengths. They may also emit light at different times. By changing the wavelength and angle of the emitted light, different images can be captured continuously, and multiple images can be used for authentication, achieving high security.

[0327] FIG. 9C shows a biometric authentication device for palm veins, which includes a housing 921, an operation button 922, a detection unit 923, a light source 924 that emits near-infrared light, and the like. The shape of the veins in the palm can be recognized by holding the hand over the detection unit 923. A personal identification number or the like can also be input using the operation button. A light source 924 is disposed around the detection unit 923 and irradiates an object (hand). Then, reflected light from the object is incident on the detection unit 923. A light-emitting device according to one embodiment of the present invention can be used for the light source 924. An imaging device 925 is disposed directly below the detection unit 923 and can capture an image of the object (the entire image of the hand). Note that an optical system may be provided between the detection unit 923 and the imaging device 925. The above-described device configuration can also be used for a biometric authentication device for finger veins.

[0328] FIG. 9D shows a nondestructive inspection device, which includes a housing 931, an operation panel 932, a transport mechanism 933, a monitor 934, a detection unit 935, a light source 938 that emits near-infrared light, and the like. A light-emitting device according to one embodiment of the present invention can be used for the light source 938. An inspected member 936 is transported by the transport mechanism 933 to a position directly below the detection unit 935. The inspected member 936 is irradiated with near-infrared light from the light source 938, and the transmitted light is captured by an imaging device 937 provided in the detection unit 935. The captured image is displayed on the monitor 934. The inspected member is then transported to the exit of the housing 931, where defective products are separated and collected. By capturing images using near-infrared light, defective elements such as defects and foreign matter inside the inspected member can be detected nondestructively and quickly.

[0329] FIG. 9E shows a mobile phone, which includes a housing 981, a display portion 982, operation buttons 983, an external connection port 984, a speaker 985, a microphone 986, a first camera 987, a second camera 988, and the like. The mobile phone includes a touch sensor in the display portion 982. The housing 981 and the display portion 982 are flexible. Any operation, such as making a call or inputting characters, can be performed by touching the display portion 982 with a finger, a stylus, or the like. The first camera 987 can acquire a visible light image, and the second camera 988 can acquire an infrared light image (near-infrared light image). The mobile phone or the display portion 982 shown in FIG. 9E may include a light-emitting device of one embodiment of the present invention.

[0330] This embodiment mode can be combined with other embodiment modes as appropriate. EXAMPLES

[0331] (Synthesis Example 1) Example 1 This example describes a method for synthesizing an organic compound according to one embodiment of the present invention. This example describes a method for synthesizing N-[4″-(9H-carbazol-9-yl)-1,1′:4′,1″-terphenyl-4-yl]-N-(1,1′-biphenyl-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: oYGTBiF(2)) represented by structural formula (100) in Embodiment 1.

[0332] [ka]

[0333] First, 1.3 g (3.7 mmol) of N-[1,1'-biphenyl]-2-yl-9,9-dimethyl-9H-fluoren-2-amine, 1.6 g (3.7 mmol) of 9-(4''-chloro[1,1':4',1''-terphenyl]-4-yl)-9H-carbazole, and 26 mg (74 μmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (registered trademark: cBRIDP) were placed in a 200 mL three-neck flask equipped with a reflux condenser, and the system was replaced with nitrogen. 0.71 g (7.4 mmol) of sodium tert-butoxide and 30 mL of xylene were added to the system, and reduced pressure degassing and nitrogen replacement were performed three times each. 21 mg (37 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the system, and the system was stirred at 150 °C for 10 hours. After stirring, insoluble matter was removed from the mixture by suction filtration. Water was added to the obtained filtrate, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water, and then washed with saturated saline. The organic layer was dried over magnesium sulfate. The obtained mixture was gravity filtered to remove magnesium sulfate. The obtained filtrate was concentrated to obtain 2.6 g of a yellow viscous solid. The obtained solid was purified by silica gel chromatography (developing solvent: toluene:hexane = 1:2), and the obtained pale yellow solid was further recrystallized with toluene to obtain 0.83 g of a pale yellow solid in a yield of 30%.

[0334] The obtained solid (0.83 g) was purified by train sublimation. The sublimation purification was performed by heating the solid at 320°C under a pressure of 3.8 Pa for 16 hours while flowing argon at 15 mL / min. After the sublimation purification, 0.55 g of the target pale yellow solid was obtained with a recovery rate of 66%. In the sublimation purification, the material was sublimated by heating at 320°C, and the recovery rate was also high at 66%, confirming that the organic compound of one embodiment of the present invention has good sublimability and no problems with the deposition process. The synthesis scheme is shown in (A-1).

[0335] [ka]

[0336] Nuclear magnetic resonance spectroscopy of the resulting pale yellow solid (1 The results of the analysis by H-NMR are shown below. From these results, it was found that oYGTBiF(2) represented by structural formula (100) was obtained in this example.

[0337] 1 H NMR (dichloromethane-d2,300MHz): δ=8.17(d, J=7.8Hz, 2H), 7.91(d, J=8.7Hz, 2H), 7.78(d, J=8.7Hz, 2H), 7.71(d, J=8.7Hz, 2H), 7.67(d, J=8.7Hz, 2H), 7.57(d, J=7.2Hz, 1H), 7.52-7.19(m, 18H), 7.14-7.06(m, 5H), 6.92(d, J=1.8Hz, 1H), 6.79(dd, J1=6.0Hz, J2=2.1Hz, 1H), 1.30(s, 6H).

[0338] Next, we measured the UV-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and emission spectrum of the toluene solution and solid thin film of oYGTBiF(2). The solid thin film was prepared on a quartz substrate by vacuum deposition.

[0339] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: V-550, manufactured by JASCO Corporation; thin film: U-4100, manufactured by Hitachi High-Technologies Corporation). The absorption spectrum of oYGTBiF(2) in toluene solution was calculated by subtracting the absorption spectrum obtained by placing toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution of oYGTBiF(2) in a quartz cell. The absorption spectrum of the thin film was calculated as the absorbance (-log 10 It was calculated from [%T / (100-%R)]. %T represents transmittance, and %R represents reflectance. A fluorometer (FS920, manufactured by Hamamatsu Photonics Co., Ltd.) was used to measure the emission spectrum. Both the absorption spectrum and the emission spectrum were measured at room temperature.

[0340] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 10(A), where the horizontal axis represents wavelength and the vertical axis represents absorption intensity and emission intensity.

[0341] As shown in FIG. 10(A), in the toluene solution of oYGTBiF(2), an absorption peak was observed near 366 nm and an emission peak was observed near 421 nm (excitation wavelength: 366 nm).

[0342] The measurement results of the absorption spectrum and emission spectrum of the obtained solid thin film are shown in Figure 10(B), where the horizontal axis represents the wavelength and the vertical axis represents the absorption intensity and emission intensity.

[0343] As shown in FIG. 10(B), the solid thin film of oYGTBiF(2) exhibited absorption peaks at around 294 nm, 350 nm, and 367 nm, and an emission peak at around 440 nm (excitation wavelength: 365 nm).

[0344] It has been found that oYGTBiF(2), an organic compound according to one embodiment of the present invention, is a suitable host material for fluorescent materials that emit light with energy on the blue or longer wavelength side, and for phosphorescent materials that emit light with energy on the green or longer wavelength side. oYGTBiF(2) can also be used as a host material or a light-emitting material used together with a material that emits light in the visible or near-infrared region (such as a fluorescent material, a delayed fluorescent material, or a phosphorescent material).

[0345] Next, the HOMO and LUMO levels of oYGTBiF(2) were calculated based on cyclic voltammetry (CV) measurements. The calculation method is shown below.

[0346] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C). The solution used for CV measurement was prepared by dissolving the supporting electrolyte tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) in dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) to a concentration of 100 mmol / L, and further dissolving the measurement target to a concentration of 2 mmol / L.

[0347] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.), the auxiliary electrode was a platinum electrode (Pt counter electrode (5 cm) for VC-3, manufactured by BAS Co., Ltd.), and the reference electrode was an Ag / Ag + An electrode (RE7 non-aqueous solvent reference electrode, manufactured by BAS Co., Ltd.) was used. The measurements were carried out at room temperature (20°C or higher and 25°C or lower).

[0348] The scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] relative to the reference electrode were measured. Ea was the midpoint potential of the oxidation-reduction wave, and Ec was the midpoint potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment relative to the vacuum level is known to be -4.94 [eV], the HOMO level and the LUMO level can be calculated from the formulas HOMO level [eV] = -4.94 - Ea and LUMO level [eV] = -4.94 - Ec, respectively.

[0349] In addition, the CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was compared with the oxidation-reduction wave in the 1st cycle to examine the electrical stability of the compound.

[0350] As a result, the HOMO level of oYGTBiF(2) was found to be -5.42 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of oYGTBiF(2) was found to be -2.31 eV in the measurement of the reduction potential Ec [V], revealing high electron blocking properties. In addition, when the waveforms after the 1st and 100th cycles were compared in the repeated measurement of the oxidation-reduction wave, 88% of the peak intensity was maintained in the Ea measurement, and 99% of the peak intensity was maintained in the Ec measurement, confirming that oYGTBiF(2) has very good resistance to oxidation and reduction.

[0351] Differential scanning calorimetry (DSC) of oYGTBiF(2) was also performed using a Pyris1 DSC manufactured by PerkinElmer. Differential scanning calorimetry was performed by heating the material from -10°C to 320°C at a heating rate of 40°C / min, holding the material at the same temperature for 1 minute, and then cooling it to -10°C at a heating rate of 100°C / min twice in succession. The results of the second cycle of DSC measurement revealed that the glass transition point of oYGTBiF(2) was 137°C, indicating that it is a material with extremely high heat resistance.

[0352] Thermogravimetry-Differential Thermal Analysis of oYGTBiF(2) was also performed. A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurements. The measurements were performed at atmospheric pressure, with a heating rate of 10°C / min, and under a nitrogen gas flow (flow rate of 200mL / min). In the thermogravimetry-Differential Thermal Analysis, it was found that the temperature at which the weight determined by thermogravimetry was -5% of the weight at the start of the measurement (decomposition temperature) was 484°C, indicating that the substance has high heat resistance.

[0353] The above results demonstrate that the organic compound of one embodiment of the present invention has both high heat resistance and high sublimability, and can provide an organic optical device (light-emitting device and light-receiving device) with high heat resistance and can increase the productivity of device fabrication. EXAMPLES

[0354] In this example, a light-emitting device according to one embodiment of the present invention was manufactured and evaluated, and the results are described.

[0355] In this example, device 1 using oYGTBiF(2) (structural formula (100)) described in Example 1, and comparative devices 2, 3, and 4 for comparison were fabricated as light-emitting devices, and the results of their evaluation are described.

[0356] The structures of the four light-emitting devices used in this example are shown in Fig. 11, and their specific configurations are shown in Table 1. The chemical formulas of the materials used in this example are shown below.

[0357] [Table 1]

[0358] [ka]

[0359] <Fabrication of light-emitting devices> The light-emitting device shown in this embodiment has a structure in which a first electrode 801 is formed on a substrate 800 as shown in FIG. 11, a hole injection layer 811, a hole transport layer 812, a light-emitting layer 813, an electron transport layer 814, and an electron injection layer 815 are sequentially stacked on the first electrode 801 as an EL layer 802, and a second electrode 803 is stacked on the electron injection layer 815.

[0360] First, a first electrode 801 was formed on a substrate 800. The electrode area was 4 mm 2 The dimensions of the first electrode 801 were (2 mm×2 mm). A glass substrate was used as the substrate 800. The first electrode 801 was formed by depositing indium tin oxide containing silicon oxide (ITSO) to a thickness of 70 nm by a sputtering method. In this embodiment, the first electrode 801 functions as an anode.

[0361] As a pretreatment, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. -4 The substrate was introduced into a vacuum deposition apparatus whose inside had been reduced in pressure to about Pa, and vacuum baking was carried out at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0362] Next, a hole injection layer 811 was formed on the first electrode 801. The hole injection layer 811 was formed by evaporating the solution in a vacuum deposition apparatus for 10 -4After reducing the pressure to 10 Pa, material X and ALD-MP001Q (Bunseki Kobo Co., Ltd., material serial number: 1S20180314) were co-deposited in a ratio of material X:ALD-MP001Q=1:0.1 (weight ratio) to form a film with a thickness of 10 nm. Note that ALD-MP001Q is an acceptor material.

[0363] Next, a hole transport layer 812 was formed on the hole injection layer 811. The hole transport layer 812 was formed by evaporating material X to a thickness of 20 nm, and evaporating N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP) to a thickness of 10 nm.

[0364] As the material X in the hole injection layer 811 and the hole transport layer 812, in the device 1, N-[4″-(9H-carbazol-9-yl)-1,1′:4′,1″-terphenyl-4-yl]-N-(1,1′-biphenyl-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: oYGTBiF(2)) was used, and in the comparative device 2, N-[4′-(9H-carbazol-9-yl)-1,1′-biphenyl-4-yl]-N-(1,1′-biphenyl-2-yl)-9,9′-dimethyl-9H-fluoren-2-amine (abbreviation: oYGTBiF(2)) was used. In comparative device 1, 2,4'-diphenyl-4''-[4'-(9H-carbazol-9-yl)-1,1'-biphenyl-4-yl]triphenylamine (abbreviation: oYGTBi1BP) was used, and in comparative device 2, N-[4''-(9H-carbazol-9-yl)-1,1':4',1''-terphenyl-4-yl]-N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: YGTBiF(2)) was used.

[0365] Next, the light-emitting layer 813 was formed on the hole-transporting layer 812. 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) was used as the host material, and 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) was used as the guest material (fluorescent material), and they were co-evaporated so that the weight ratio was cgDBCzPA:3,10PCA2Nbf(IV)-02=1:0.015. The film thickness was 25 nm.

[0366] Next, the electron transport layer 814 was formed on the light emitting layer 813. The electron transport layer 814 was formed by evaporating cgDBCzPA to a thickness of 15 nm and evaporating 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) to a thickness of 10 nm.

[0367] Next, the electron injection layer 815 was formed on the electron transport layer 814. The electron injection layer 815 was formed by vapor deposition using lithium fluoride (LiF) so as to have a film thickness of 1 nm.

[0368] Next, a second electrode 803 was formed on the electron injection layer 815. The second electrode 803 was formed by vapor deposition of aluminum so as to have a film thickness of 200 nm. In this example, the second electrode 803 functions as a cathode.

[0369] Through the above steps, a light-emitting device including an EL layer 802 sandwiched between a pair of electrodes was formed over a substrate 800. Note that the hole-injection layer 811, the hole-transport layer 812, the light-emitting layer 813, the electron-transport layer 814, and the electron-injection layer 815 described in the above steps are functional layers that form the EL layer in the light-emitting device of one embodiment of the present invention. In addition, in all of the deposition steps in the above-described manufacturing method, deposition by resistance heating was used.

[0370] The light-emitting device fabricated as described above is sealed with another substrate (not shown). When sealing is performed using another substrate (not shown), another substrate (not shown) coated with an adhesive that is hardened by ultraviolet light is fixed on the substrate 800 in a glove box with a nitrogen atmosphere, and the substrates are bonded together so that the adhesive adheres to the periphery of the light-emitting device formed on the substrate 800. During sealing, 365 nm ultraviolet light is applied at 6 J / cm. 2 The adhesive was solidified by irradiation and then stabilized by heat treatment at 80°C for 1 hour.

[0371] <Operation characteristics of light-emitting devices> The operating characteristics of the light-emitting device fabricated in this example were measured at room temperature.

[0372] Fig. 12 shows the luminance-current efficiency characteristics of the light-emitting device. Fig. 13 shows the voltage-luminance characteristics of the light-emitting device. Fig. 14 shows the voltage-current characteristics of the light-emitting device. Fig. 15 shows the luminance-external quantum efficiency characteristics of the light-emitting device.

[0373] Table 2 shows 1000cd / m 2 The main initial characteristic values ​​of the light-emitting device in the vicinity are shown.

[0374] [Table 2]

[0375] 12 to 15 and Table 2, it was found that the luminous efficiency was high in Device 1, Comparative Device 2, and Comparative Device 4. It was also found that Device 1 had a higher luminous efficiency than Comparative Device 3.

[0376] In addition, the light-emitting device is supplied with 12.5mA / cm 216 shows the emission spectra when a current was passed at a current density of 1000 nm. As shown in Fig. 16, Device 1 exhibited an emission spectrum having a maximum peak near 459 nm, which is attributable to the emission of 3,10PCA2Nbf(IV)-02 contained in the light-emitting layer 813. Similarly, Comparative Device 2 exhibited an emission spectrum having a maximum peak near 458 nm, Comparative Device 3 exhibited an emission spectrum having a maximum peak near 457 nm, and Comparative Device 4 exhibited an emission spectrum having a maximum peak near 459 nm.

[0377] Next, a reliability test was carried out on the light-emitting device. The results of the reliability test are shown in Figure 17. In Figure 17(A), the vertical axis shows normalized luminance (%) when the initial luminance is taken as 100%, and the horizontal axis shows the driving time (h). In Figure 17(B), the vertical axis shows the voltage change (ΔV) from the initial voltage (when the driving time is 0 hours), and the horizontal axis shows the driving time (h). The reliability test was carried out at a current density of 50 mA / cm 2 The light-emitting device was driven by setting the

[0378] Comparing the luminance after 330 hours, Device 1 maintained 85% of the initial luminance, Comparative Device 2 maintained 80% of the initial luminance, Comparative Device 3 maintained 87% of the initial luminance, and Comparative Device 4 maintained 82% of the initial luminance.

[0379] This shows that Device 1 has the same luminous efficiency and higher reliability as Comparative Device 2 and Comparative Device 4. It is also shown that Device 1 has a higher luminous efficiency than Comparative Device 3 and has the same reliability.

[0380] oYGTBiF(2) used in device 1 is a tertiary amine, and the ortho position of the biphenyl skeleton, the fluorene skeleton, and the terphenylene skeleton are bonded to the nitrogen of the amine, and the carbazole skeleton is bonded to the phenylene group farthest from the nitrogen of the amine of the terphenylene skeleton. In other words, the nitrogen of the amine and the nitrogen of the carbazole are bonded via the terphenylene skeleton. On the other hand, oYGBBiF used in comparative device 2 is different from oYGTBiF(2) used in device 1 in that the nitrogen of the carbazole and the nitrogen of the amine are bonded via the biphenylene skeleton, not the terphenylene skeleton. In addition, oYGTBi1BP used in comparative device 3 is different from oYGTBiF(2) in that the para position of the biphenyl skeleton, not the fluorene skeleton, is bonded to the nitrogen of the amine. YGTBiF(2) used in comparative device 4 differs from oYGTBiF(2) in that the para position of the biphenyl skeleton is bonded to the nitrogen of the amine, rather than to the ortho biphenyl skeleton. From the above, it can be said that both the luminous efficiency and reliability of the light-emitting device can be improved by using an organic compound that is a tertiary amine, in which the nitrogen of the amine is bonded to the ortho position of the biphenyl skeleton, the fluorene skeleton, and the terphenylene skeleton, and the phenylene group of the terphenylene skeleton that is the furthest from the nitrogen of the amine is bonded to a carbazole skeleton. EXAMPLES

[0381] In this example, a light-emitting device according to one embodiment of the present invention was manufactured and evaluated, and the results are described.

[0382] In this example, Device 5 and Device 6 were fabricated using oYGTBiF(2) (structural formula (100)) described in Example 1 as light-emitting devices, and the results of their evaluation will be described.

[0383] Table 3 shows the specific configurations of the two light-emitting devices used in this example. The structure of device 5 is similar to that of device 1 (FIG. 11) except that the light-emitting material of the light-emitting layer 813 is changed, and the structure of device 6 is similar to that of device 5 except that the thickness of the hole transport layer 812 is increased. Therefore, with regard to the methods of fabricating device 5 and device 6, Example 2 can be referred to for the parts that are similar to those of device 1. The chemical formulas of the materials used in this example are shown below.

[0384] [Table 3]

[0385] [ka]

[0386] As shown in Table 3, in the light-emitting device of this embodiment, cgDBCzPA was used as the host material in the light-emitting layer 813, and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03) was used as the light-emitting material.

[0387] As shown in Table 3, the thickness of oYGTBiF(2) used in the hole transport layer 812 is different between device 5 and device 6.

[0388] <Operation characteristics of light-emitting devices> The operating characteristics of the light-emitting device fabricated in this example were measured at room temperature.

[0389] Fig. 18 shows the luminance-current efficiency characteristics of the light-emitting device. Fig. 19 shows the voltage-luminance characteristics of the light-emitting device. Fig. 20 shows the voltage-current characteristics of the light-emitting device. Fig. 21 shows the luminance-external quantum efficiency characteristics of the light-emitting device.

[0390] Table 4 shows 1000cd / m 2 The main initial characteristic values ​​of the light-emitting device in the vicinity are shown.

[0391] [Table 4]

[0392] 18 to 21 and Table 4, it was found that the device 5 and the device 6 had high luminous efficiency. In addition, although the thickness of the hole transport layer 812 of the device 6 was 100 nm thicker than that of the device 5, the luminous efficiency of the device 6 was 1000 cd / m 2 The driving voltage at 2000 Hz increased by only 0.6 V, indicating that the hole transport property of oYGTBiF(2) is excellent.

[0393] In addition, the light-emitting device is supplied with 12.5mA / cm 2 FIG. 22 shows the emission spectra when a current was passed at a current density of 1,6BnfAPrn-03. As shown in FIG. 22, device 5 exhibited an emission spectrum having a maximum peak near 458 nm, which is due to the emission of 1,6BnfAPrn-03 contained in the light-emitting layer 813. Similarly, device 6 exhibited an emission spectrum having a maximum peak near 456 nm. Note that the optical path related to the emission of devices 5 and 6 is slightly different from each other, and the emission chromaticity is different, but this is because only the film thickness of oYGTBiF(2) was changed to evaluate the transport property of this material.

[0394] Next, a reliability test was carried out on the light-emitting device. The results of the reliability test are shown in Figure 23. In Figure 23(A), the vertical axis shows normalized luminance (%) when the initial luminance is taken as 100%, and the horizontal axis shows the driving time (h). In Figure 23(B), the vertical axis shows the voltage change (ΔV) from the initial voltage (when the driving time is 0 hours), and the horizontal axis shows the driving time (h). The reliability test was carried out at a current density of 50 mA / cm 2 The light-emitting device was driven by setting the

[0395] The results of the reliability test showed that both Device 5 and Device 6 exhibited high reliability.

[0396] In general, when the concentration of an electron acceptor material in a hole injection layer is increased and a hole transport material with a deep HOMO level is used, the driving voltage of a light-emitting device may be increased by thickening the hole transport layer. As shown in FIG. 23B, the difference between the voltage after 310 hours and the initial voltage in both Device 5 and Device 6 was within 0.15 V, indicating that the voltage increase was small. From the above, it was found that the driving voltage of a light-emitting device is unlikely to increase even if the thickness of the hole transport layer using the organic compound of one embodiment of the present invention is increased. EXAMPLES

[0397] In this example, a light-emitting device according to one embodiment of the present invention was manufactured and evaluated, and the results are described.

[0398] In this example, Device 7 and Device 8 were fabricated using oYGTBiF(2) (structural formula (100)) described in Example 1 as light-emitting devices, and the results of their evaluation will be described.

[0399] Table 5 shows the specific configurations of the two light-emitting devices used in this example. The structure of device 7 is similar to that of device 1 (FIG. 11) except that the materials of the light-emitting layer 813 and the electron transport layer 814 are changed, and the structure of device 8 is similar to that of device 7 except that the thickness of the hole transport layer 812 is increased. Therefore, for the methods of manufacturing devices 7 and 8, refer to Example 2 for the parts that are similar to those of device 1. The structures of devices 7 and 8 are similar to those of device 1 (FIG. 11), and refer to Example 2 for the methods of manufacturing them. The chemical formulas of the materials used in this example are shown below.

[0400] [Table 5]

[0401] [ka]

[0402] As shown in Table 5, in the light-emitting device of this embodiment, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) was used as the host material and 1,6BnfAPrn-03 was used as the light-emitting material in the light-emitting layer 813. In addition, the electron transport layer 814 was formed by co-evaporation of 2-{4-[9,10-di(naphthalene-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN) and 8-hydroxyquinolinato-lithium (abbreviation: Liq) in a weight ratio of 1:1 (=ZADN:Liq) to a film thickness of 25 nm.

[0403] As shown in Table 5, the thickness of the oYGTBiF(2) used in the hole transport layer 812 is different between device 7 and device 8.

[0404] <Operation characteristics of light-emitting devices> The operating characteristics of the light-emitting device fabricated in this example were measured at room temperature.

[0405] Figure 24 shows the luminance-current efficiency characteristics of the light-emitting device. Figure 25 shows the voltage-luminance characteristics of the light-emitting device. Figure 26 shows the voltage-current characteristics of the light-emitting device. Figure 27 shows the luminance-external quantum efficiency characteristics of the light-emitting device.

[0406] Table 6 shows 1000cd / m 2 The main initial characteristic values ​​of the light-emitting device in the vicinity are shown.

[0407] [Table 6]

[0408] 24 to 27 and Table 6, it was found that Device 7 and Device 8 had high luminous efficiency. In addition, although Device 8 had a hole transport layer 812 100 nm thicker than Device 7, it had a luminous efficiency of 1000 cd / m 2The driving voltage at 2000 Hz increased by only 0.6 V, indicating that the hole transport property of oYGTBiF(2) is excellent.

[0409] In addition, the light-emitting device is supplied with 12.5mA / cm 2 FIG. 28 shows the emission spectra when a current was passed at a current density of 1,6BnfAPrn-03. As shown in FIG. 28, device 7 exhibited an emission spectrum having a maximum peak near 458 nm, which is due to the emission of 1,6BnfAPrn-03 contained in the light-emitting layer 813. Similarly, device 8 exhibited an emission spectrum having a maximum peak near 456 nm. Note that the optical path related to the emission of devices 7 and 8 is slightly different from each other, and the emission chromaticity is different. This is because only the film thickness of oYGTBiF(2) was changed to evaluate the transport property of this material.

[0410] Next, a reliability test was conducted on the light-emitting device. The results of the reliability test are shown in Figure 29. In Figure 29(A), the vertical axis shows normalized luminance (%) when the initial luminance is taken as 100%, and the horizontal axis shows the drive time (h). In Figure 29(B), the vertical axis shows the voltage change (ΔV) from the initial voltage (when the drive time is 0 hours), and the horizontal axis shows the drive time (h). The reliability test was conducted at a current density of 50 mA / cm 2 The light-emitting device was driven by setting the

[0411] The results of the reliability test showed that both Device 7 and Device 8 exhibited high reliability.

[0412] 29B, the difference between the initial voltage and the voltage after 380 hours in both Device 7 and Device 8 was within 0.20 V, indicating that the voltage increase was small. From the above, it was found that the driving voltage of the light-emitting device is unlikely to increase even if the thickness of the hole-transport layer using the organic compound of one embodiment of the present invention is increased.

[0413] In addition, in Example 3 and Example 4, the materials used for the light-emitting layer and the electron transport layer of the light-emitting device are different. From these examples, it was shown that the organic compound of one aspect of the present invention can be combined with various materials to fabricate a light-emitting device with high luminous efficiency and reliability.

[0414] (Reference Example) Hereinafter, the synthesis methods of 2,4'-diphenyl-4''-[4'-(9H-carbazol-9-yl)-1,1'-biphenyl-4-yl]triphenylamine (abbreviation: oYGTBi1BP) and N-[4''-(9H-carbazol-9-yl)-1,1':4',1''-terphenyl-4-yl]-N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: YGTBiF(2)), which were used for the comparative device of Example 2, will be described.

[0415]

Chemical Formula

[0416] <Synthesis of oYGTBi1BP> 1.4g (4.2mmol) of N-(4-biphenylyl)-2-biphenylamine, 1.8g (4.2mmol) of 9-(4''-chloro[1,1':4',1''-terphenyl]-4-yl)-9H-carbazole, and 30mg (84μmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (registered trademark: cBRIDP) were placed in a 200mL three-neck flask equipped with a reflux condenser, and the system was purged with nitrogen. 0.81g (8.4mmol) of sodium tert-butoxide and 100mL of xylene were added to the system, and degassing under reduced pressure and nitrogen replacement were performed three times each. 24mg (42μmol) of bis(dibenzylideneacetone)palladium(0) was added to the system, and the mixture was stirred at 150°C for 11 hours. After stirring, insoluble matter was removed from the mixture by suction filtration. Water was added to the obtained filtrate, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water, and then washed with saturated saline. The organic layer was dried over magnesium sulfate. The obtained mixture was gravity filtered to remove magnesium sulfate. The obtained filtrate was purified by filtration through alumina-celite (Wako Pure Chemical Industries, Ltd., catalog number: 531-16855), and the obtained filtrate was concentrated to obtain 2.3 g of a pale yellow solid. The obtained solid was purified by recrystallization (solvent used: a mixed solvent of toluene and hexane), and 1.5 g of the target pale yellow solid was obtained in a yield of 50%.

[0417] The obtained solid (1.5 g) was purified by train sublimation. The purification was carried out by heating the solid at 345°C for 16 hours under a pressure of 3.8 Pa while flowing argon at 15 mL / min. After purification by sublimation, 1.0 g of the target pale yellow solid was obtained with a recovery rate of 66%. The synthesis scheme is shown in (X-1).

[0418] [ka]

[0419] The pale yellow solid obtained 1 The results of the H-NMR analysis are shown below. These results demonstrated that oYGTBi1BP was obtained.

[0420] 1 H NMR (dichloromethane-d2,300MHz): δ=8.16(d, J=8.1Hz, 2H), 7.90(dd, J1=4.5Hz, J2=1.8Hz, 2H), 7.77(dd, J1=4. 2Hz, J2=2.1Hz, 2H), 7.70-7.66(m, 4H), 7.55-7.14(m, 24H), 6.99(d, J=5.7Hz, 2H), 6.96(d, J=5.7Hz, 2H).

[0421] Next, the absorption spectrum and emission spectrum of the toluene solution and solid thin film of oYGTBi1BP were measured. The measurement conditions are the same as those in Example 1, so they are omitted.

[0422] As a result of the measurement, the toluene solution of oYGTBi1BP showed an absorption peak at around 365 nm and an emission peak at 411 nm (excitation wavelength 346 nm), while the solid thin film of oYGTBi1BP showed absorption peaks at around 296 nm, 347 nm, and 362 nm, and an emission peak at around 426 nm (excitation wavelength 360 nm).

[0423] Next, the HOMO level and the LUMO level of oYGTBi1BP were calculated based on the CV measurement. The calculation method is the same as that in Example 1, so it is omitted.

[0424] In addition, the CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was compared with the oxidation-reduction wave in the 1st cycle to examine the electrical stability of the compound.

[0425] As a result, the HOMO level of oYGTBi1BP was found to be -5.50 eV in the measurement of the oxidation potential Ea [V]. Meanwhile, the LUMO level of oYGTBi1BP was found to be -2.32 eV in the measurement of the reduction potential Ec [V]. In addition, when the waveforms after the first and 100th cycles were compared in the repeated measurement of the oxidation-reduction wave, the peak intensity was 85% in the Ea measurement and 94% in the Ec measurement, confirming that oYGTBi1BP has very good resistance to oxidation and reduction.

[0426] Also, the differential scanning calorimetry (DSC measurement) of oYGTBi1BP was measured using Pyris1 DSC manufactured by PerkinElmer. In the differential scanning calorimetry, after raising the temperature from -10°C to 380°C at a heating rate of 40°C / min, holding at the same temperature for 1 minute, and then cooling to -10°C at a cooling rate of 100°C / min, this operation was continuously performed twice. From the DSC measurement results of the second cycle, it became clear that the glass transition point of oYGTBi1BP is 122°C, indicating that it is a substance with very high heat resistance.

[0427] Also, differential thermal analysis of oYGTBi1BP was performed. Since the measurement method is the same as in Example 1, it is omitted. In thermogravimetric measurement - differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric measurement becomes -5% of the starting weight is 486°C, indicating that it is a substance with high heat resistance.

[0428] <Synthesis of <YGTBiF(2)>> 2.0 g (4.0 mmol) of 2 - amino - N - [(1,1'-biphenyl)-4 - yl]-N-(4 - bromophenyl)-9,9 - dimethylfluorene, 1.4 g (4.0 mmol) of [4'-(carbazol - 9 - yl)-4 - biphenylyl]boronic acid, 24 mg (76 μmol) of tri(ortho - tolyl)phosphine, 5 mL of 2M aqueous potassium carbonate solution, 30 mL of toluene, and 10 mL of ethanol were placed in a 200 mL three - necked flask equipped with a reflux condenser. After degassing the mixture under reduced pressure, the system was purged with nitrogen. This mixture was heated at 60°C, and 8.9 mg (40 μmol) of palladium(II) acetate was added to this mixture. This mixture was refluxed for 10 hours. The resulting mixture was suction - filtered. Water was added to the obtained filtrate, and the aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined, washed with water and saturated brine, and dried over magnesium sulfate. The filtrate obtained by natural filtration of this mixture was concentrated to obtain a light - brown solid. This solid was purified by high - performance liquid chromatography (HPLC) (mobile phase: chloroform), and 1.3 g of the desired pale - yellow solid was obtained in a yield of 43%.

[0429] The obtained solid (1.3 g) was purified by train sublimation. The purification was carried out by heating the solid at 350°C for 15 hours under a pressure of 3.1 Pa while flowing argon at 15 mL / min. After purification by sublimation, 1.1 g of the target pale yellow solid was obtained with a recovery rate of 85%. The synthesis scheme is shown in (Y-1).

[0430] [ka]

[0431] The pale yellow solid obtained 1 The results of the H-NMR analysis are shown below. These results demonstrated that YGTBiF(2) was obtained.

[0432] 1 H NMR (dichloromethane-d2,300MHz): δ=8.17(d, J=7.8Hz, 2H), 7.92(d, J=8.7Hz, 2H), 7.75(dd, J1=27.6Hz, J2=9.0Hz, 4H), 7.70-7. 61(m, 8H), 7.56(d, J=9.0Hz, 2H), 7.52-7.42(m, 7H), 7.36-7.24(m, 10H), 7.14(dd, J1=6.0Hz, J2=2.1Hz, 1H), 1.45(s, 6H).

[0433] Next, the absorption spectrum and emission spectrum of the toluene solution and solid thin film of YGTBiF(2) were measured. The measurement conditions are the same as those in Example 1, so they are omitted.

[0434] The measurement results showed that the toluene solution of YGTBiF(2) had an absorption peak at around 363 nm and an emission peak at 425 nm (excitation wavelength 363 nm).The solid thin film of YGTBiF(2) had absorption peaks at around 294 nm, 350 nm, and 365 nm, and an emission peak at around 442 nm (excitation wavelength 380 nm).

[0435] Next, the HOMO level and the LUMO level of YGTBiF(2) were calculated based on the CV measurement. The calculation method is the same as that in Example 1, so it is omitted.

[0436] In addition, the CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was compared with the oxidation-reduction wave in the 1st cycle to examine the electrical stability of the compound.

[0437] As a result, the HOMO level of YGTBiF(2) was found to be -5.41 eV in the measurement of the oxidation potential Ea [V]. Meanwhile, the LUMO level of YGTBiF(2) was found to be -2.34 eV in the measurement of the reduction potential Ec [V]. In addition, when the waveforms after the first and 100th cycles were compared in the repeated measurement of the oxidation-reduction wave, 90% of the peak intensity was maintained in the Ea measurement, and 96% of the peak intensity was maintained in the Ec measurement, confirming that YGTBiF(2) has very good resistance to oxidation and reduction.

[0438] Differential scanning calorimetry (DSC) of YGTBiF(2) was also performed using a Pyris1 DSC manufactured by PerkinElmer. Differential scanning calorimetry was performed by heating the material from -10°C to 330°C at a heating rate of 40°C / min, holding the material at the same temperature for 1 minute, and then cooling it to -10°C at a heating rate of 100°C / min, twice in succession. The results of the second cycle of DSC measurement revealed that the glass transition point of YGTBiF(2) was 145°C, indicating that the material has extremely high heat resistance.

[0439] In addition, differential thermal analysis of YGTBiF(2) was performed. The measurement method is omitted since it is the same as that in Example 1. In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight determined by thermogravimetry was -5% of the weight at the start of the measurement was 499°C, indicating that it is a substance with high heat resistance. [Explanation of symbols]

[0440] 101 First electrode 102 Second electrode 103 EL layer 103a EL layer 103b EL layer 103c EL layer 104 Charge generating layer 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 201 Substrate 202 Insulating layer 202a Insulating layer 202b Insulating layer 203B Light-emitting devices 203G Light Emitting Device 203R Light-emitting device 203W Light Emitting Device 204 Insulating layer 205 Substrate 206B Color Filter 206G Color Filter 206R Color Filter 207 Space 208 Adhesive layer 209 Black Matrix 210 Transistor 211 First electrode 212G conductive layer 212R conductive layer 213 EL layer 213B EL layer 213G EL layer 213R EL layer 215 Second Electrode 220B optical distance 220G optical distance 220R optical distance 301 First Substrate 302 Pixel section 303 Circuit section 304a circuit section 304b circuit section 305 Sealing material 306 Second Board 307 Wiring 308 FPC 309 Transistor 310 Transistor 311 Transistor 312 Transistor 313 First electrode 314 Insulating layer 315 EL layer 316 Second Electrode 317 Organic EL Devices 318 Space 320 Transistor 321 Conductive Layer 322a conductive layer 322b conductive layer 323 Conductive Layer 324 Insulating layer 325 Insulation Layer 326 Insulating Layer 327 Semiconductor Layer 327i Channel formation region 327n low resistance region 328 Insulating Layer 330 Transistor 331 Conductive Layer 332a conductive layer 332b Conductive layer 333 Conductive Layer 334 Insulating Layer 335 Insulating Layer 337 Semiconductor Layer 338 Insulating Layer 401 First electrode 402 EL layer 403 Second electrode 405 Insulation Layer 406 Conductive Layer 407 Adhesive layer 416 Conductive Layer 420 Substrate 422 Adhesive layer 423 Barrier Layer 424 Insulating layer 450 Organic Light Emitting Diode Device 490a Board 490b board 490c Barrier Layer 800 boards 801 First electrode 802 EL layer 803 Second electrode 811 Hole injection layer 812 Hole transport layer 813 Light-emitting layer 814 Electron transport layer 815 Electron injection layer 911 Case 912 light source 913 Detection Stage 914 Imaging device 915 Light emitting part 916 Light emitting part 917 Light emitting part 921 Case 922 Operation button 923 Detection Unit 924 light source 925 Imaging Device 931 Case 932 Operation Panel 933 Conveyor mechanism 934 Monitor 935 Detection Unit 936 Inspected parts 937 Imaging Device 938 light source 981 Case 982 Display section 983 Operation button 984 External connection port 985 Speaker 986 Mike 987 First Camera 988 Second Camera 7000 Display 7001 Display section 7100 Television equipment 7101 Case 7103 Stand 7111 Remote control device 7200 Notebook Personal Computer 7211 Case 7212 Keyboard 7213 Pointing Device 7214 External connection port 7300 Digital Signage 7301 Case 7303 Speaker 7311 Information terminal 7400 Digital Signage 7401 Pillar 7411 Information terminal 7600 Mobile Information Terminal 7601 Case 7602 Hinge 7650 Mobile Information Terminal 7651 Hidden part 7800 Mobile Information Terminal 7801 Band 7802 Input / output terminal 7803 Operation button 7804 Icons 7805 Battery 9700 Automobiles 9701 Body 9702 wheels 9703 Windshield 9704 Light 9705 Fog Lamp 9710 Display section 9711 Display section 9712 Display section 9713 Display section 9714 Display section 9715 Display section 9721 Display section 9722 Display section 9723 Display section

Claims

1. An organic compound represented by general formula (G1): 【Chemistry 1】 (In the formula, R ２ ~R １３ , R ２３ ~R ２９ , R ３１ ~R ３９ , and R ４１ ~R ４８ R each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms. ２１ and R ２２ each independently represents an alkyl group having 1 to 6 carbon atoms.

2. In claim 1, R ３５ ~R ３９ represents a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

3. In claim 1 or 2, R ２１ and R ２２ are identical, organic compounds.

4. In claim 3, R ２１ and R ２２ are organic compounds, each of which represents a methyl group.

5. In any one of claims 1 to 4, R ４１ ~R ４８ each independently represents a hydrogen atom, a methyl group, a tert-butyl group, or a substituted or unsubstituted phenyl group.

6. A light-emitting device comprising the organic compound according to claim 1 between a pair of electrodes.

7. A light-emitting layer and a hole transport layer are disposed between a pair of electrodes, At least one of the light-emitting layer and the hole-transporting layer comprises an organic compound represented by general formula (G1). 【Chemistry 2】 (In the formula, R ２ ~R １３ , R ２１ ~R ２９ , R ３１ ~R ３９ , and R ４１ ~R ４８ each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms.

8. A light-emitting layer is disposed between an anode and a cathode, The light-emitting device further comprises an organic compound represented by general formula (G1) between the anode and the light-emitting layer. 【Chemistry 3】 (In the formula, R ２ ~R １３ , R ２１ ~R ２９ , R ３１ ~R ３９ , and R ４１ ~R ４８ each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms.

9. A light-emitting layer is disposed between an anode and a cathode, a light-emitting device comprising an organic compound represented by general formula (G1) and an electron-accepting material between the anode and the light-emitting layer; 【Chemistry 4】 (In the formula, R ２ ~R １３ , R ２１ ~R ２９ , R ３１ ~R ３９ , and R ４１ ~R ４８ each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms.

10. In claim 9, A light-emitting device having a region in which the organic compound and the electron-accepting material are intermixed.

11. A light-emitting layer is disposed between a pair of electrodes, The light-emitting device, wherein the light-emitting layer comprises an organic compound represented by general formula (G1). 【Chemistry 5】 (In the formula, R ２ ~R １３ , R ２１ ~R ２９ , R ３１ ~R ３９ , and R ４１ ~R ４８ each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 13 carbon atoms.

12. A light emitting device according to any one of claims 6 to 11, A light emitting device comprising at least one of a transistor and a substrate.

13. A light emitting device according to claim 12; A light emitting module having at least one of a connector and an integrated circuit.

14. A light emitting device according to claim 12; An electronic device having at least one of an antenna, a battery, a housing, a camera, a speaker, a microphone, and an operation button.

15. A light emitting device according to any one of claims 6 to 11, A lighting device having at least one of a housing, a cover, and a support base.

16. A light-receiving device comprising the organic compound according to claim 1 between a pair of electrodes.

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