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

Abstract

Organic compound represented by a formula (G0): where one of R 1 to R 5 represents a formula (A), where the others of R 1 to R 5 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, where R 6 to R 13 , R 23 to R 29 , R 31 to R 39 and R 41 to R 48 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and where R 21 and R 22 each represent a methyl group.

Description

Background of the invention 1. Field of the invention

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

[0002] Note that an embodiment of the present invention is not limited to the above technical field. Examples of the technical field of an 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 screen), an operation method thereof, and a manufacturing method thereof. 2. Description of the state of the art

[0003] Research and development have been actively conducted on light-emitting devices that utilize organic electroluminescence (EL) phenomena (also referred to as organic EL devices or organic EL elements). In the basic structure of an organic EL device, a layer containing a light-emitting organic compound (hereinafter also referred to as a light-emitting layer) is sandwiched between a pair of electrodes. By applying a voltage to the organic EL device, light emission from the light-emitting organic compound can be obtained.

[0004] An organic EL device is suitable for a display device because it has the following features: they are easily reduced in thickness and weight, have a fast response to an input signal, and can be operated with a low-voltage DC source.

[0005] Furthermore, an organic EL device can be formed in the form of a film, and therefore can provide planar light emission. Accordingly, a large-area light-emitting device can be easily formed. This feature is difficult to achieve with a point light source such as a light-emitting diode (LED) or a linear light source such as a fluorescent lamp. Therefore, an organic EL device also has great potential as a planar light source that can be used for a lighting device and the like.

[0006] Patent Documents 1 to 3 each disclose an aromatic amine compound having a high hole transport property as a material that can be used for a light-emitting device. [Reference][Patent document] [Patent Document 1] Japanese Patent Laid-Open No. 2009-298779 [Patent Document 2] Korean Patent Application KR 10 2018 0 131 115 A [Patent Document 3] US Patent Application US 2013 / 0 076 237 A Summary of the invention

[0007] An object of one embodiment of the present invention is to provide a novel organic compound. Another object of one embodiment of the present invention is to provide an organic compound with high heat resistance. Another object of one embodiment of the present invention is to provide an organic compound with high sublimability. Another object of one embodiment of the present invention is to provide a novel organic compound that can be used for a light-emitting device. Another object of one embodiment of the present invention is to provide a novel organic compound that can be used as a hole-transport material in a light-emitting device.Another object of an 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.

[0008] Another object of an embodiment of the present invention is to provide a light-emitting device with high emission efficiency. Another object of an embodiment of the present invention is to provide a light-emitting device with a low operating voltage. Another object of an embodiment of the present invention is to provide a light-emitting device with a long lifetime. Another object of an embodiment of the present invention is to provide a light-emitting device with high heat resistance.

[0009] It should be noted that the description of these objects does not preclude the existence of further objects. An embodiment of the present invention does not necessarily have to fulfill all of the objects. Further objects may be derived from the explanation of the description, the drawings, and the claims.

[0010] One embodiment of the present invention is an organic compound represented by a general formula (G0).

[0011] In the general formula (G0), one of R 1 to R 5 represent a general formula (A); the others each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; and R 6 to R 13 , R 23 to R 29 , R31 to R 39 and R 41 to R 48 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 21 and R 22 each represent a methyl group.

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

[0013] In the general formula (G1), R 2 to R 13 , R 23 to R 29 , R 31 to R 39 and R 41 to R 48each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 21 and R 22 each represent a methyl group.

[0014] In the general formulas (G0) and (G1), one of R 35 to R 39 preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

[0015] In the general formulas (G0) and (G1) it is preferable that R 41 to R 48 each independently represents hydrogen, a methyl group, a tert-butyl group or a substituted or unsubstituted phenyl group.

[0016] One embodiment of the present invention is a light-emitting device, a light-receiving device, or a light-emitting and light-receiving device including any of the organic compounds described above.

[0017] One embodiment of the present invention is a light-emitting device, a light-receiving device, or a light-emitting and light-receiving device that includes a layer containing an organic compound between a pair of electrodes. The organic compound-containing layer includes any of the organic compounds described above.

[0018] One embodiment of the present invention is a light-emitting device including a layer containing an organic compound between a pair of electrodes. The layer containing an organic compound includes a light-emitting layer and a hole-transporting layer. The light-emitting layer and / or the hole-transporting layer include any of the organic compounds described above.

[0019] One embodiment of the present invention is a light-emitting device including any of the above-described light-emitting devices and a transistor and / or a substrate.

[0020] One embodiment of the present invention is a light-emitting module including the light-emitting device. The light-emitting module is provided with a flexible printed circuit (FPC) or a connector such as a tape carrier package (TCP), or is mounted with an integrated circuit (IC) by a chip-on-glass (COG) method, a chip-on-film (COF) method, or the like. Note that the light-emitting module of one embodiment of the present invention may include a connector and / or an IC.

[0021] An embodiment of the present invention is an electronic device including the above-mentioned light-emitting module and an antenna, a battery, a housing, a camera, a speaker, a microphone and / or a control button.

[0022] One embodiment of the present invention is a lighting device including any of the light-emitting devices described above and a housing, a cover, and / or a support base.

[0023] An embodiment of the present invention can provide a novel organic compound. An embodiment of the present invention can provide an organic compound with high heat resistance. An embodiment of the present invention can provide an organic compound with high sublimability. An embodiment of the present invention can provide a novel organic compound that can be used for a light-emitting device. An embodiment of the present invention can provide a novel organic compound that can be used as a hole-transport material in a light-emitting device. An embodiment of the present invention can 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.

[0024] An embodiment of the present invention can provide a light-emitting device with high emission efficiency. An embodiment of the present invention can provide a light-emitting device with a low operating voltage. An embodiment of the present invention can provide a light-emitting device with a long lifetime. An embodiment of the present invention can provide a light-emitting device with high heat resistance.

[0025] It should be noted that the description of these effects does not preclude the existence of further effects. An embodiment of the present invention does not necessarily have to exhibit all of these effects. Further effects can be derived from the explanation of the description, the drawings, and the claims. Short description of the drawings Fig. 1A to Fig. 1D are cross-sectional views illustrating examples of light-emitting devices. Fig. 2A is a plan view showing an example of a light-emitting device. Fig. 2B and Fig. 2C are cross-sectional views illustrating examples of light-emitting devices. Fig. 3A and Fig. 3C are cross-sectional views illustrating examples of light-emitting devices. Fig. 3B is a cross-sectional view illustrating examples of light-emitting devices. Fig. 4A and Fig. 4B are cross-sectional views illustrating examples of light-emitting devices. Fig. 5A and Fig. 5B are a plan view and a cross-sectional view showing an example of a light-emitting device, respectively. Fig. 5C and Fig. 5D are cross-sectional views showing examples of transistors. Fig. 6A to Fig. 6D show examples of electronic devices. Fig. 7A to Fig. 7F represent examples of electronic devices. Fig. 8A to Fig. 8C represent examples of electronic devices. Fig. 9A to Fig. 9E represent examples of electronic devices. Fig. 10A and Fig. 10B show a UV-VIS absorption spectrum and an emission spectrum of an organic compound represented by a structural formula (100), respectively. Fig. 11 is a cross-sectional view illustrating a light-emitting device of an example. Fig. 12 shows the luminance-power efficiency characteristics of light-emitting devices of Example 2. Fig. Figure 13 shows the voltage-luminance characteristics of light-emitting devices of Example 2. Fig. Figure 14 shows the voltage-current characteristics of light-emitting devices of Example 2. Fig. Figure 15 shows the luminance-external quantum efficiency characteristics of light-emitting devices of Example 2. Fig. Figure 16 shows the emission spectra of light-emitting devices of Example 2. Fig. 17A and Fig. 17B shows the results of reliability tests of light-emitting devices of Example 2. Fig. 18 shows the luminance-power efficiency characteristics of light-emitting devices of Example 3. Fig. Figure 19 shows the voltage-luminance characteristics of light-emitting devices of Example 3. Fig. Figure 20 shows the voltage-current characteristics of light-emitting devices of Example 3. Fig. Figure 21 shows the luminance-external quantum efficiency characteristics of light-emitting devices of Example 3. Fig. Figure 22 shows the emission spectra of light-emitting devices of Example 3. Fig. 23A and Fig. 23B shows the results of reliability tests of light-emitting devices of Example 3. Fig. 24 shows the luminance-power efficiency characteristics of light-emitting devices of Example 4. Fig. Figure 25 shows the voltage-luminance characteristics of light-emitting devices of Example 4. Fig. Figure 26 shows the voltage-current characteristics of light-emitting devices of Example 4. Fig. Figure 27 shows the luminance-external quantum efficiency characteristics of light-emitting devices of Example 4. Fig. Figure 28 shows the emission spectra of light-emitting devices of Example 4. Fig. 29A and Fig. 29B shows the results of reliability tests of light-emitting devices of Example 4. Detailed description of the invention

[0026] Embodiments will be described in detail with reference to the drawings. It should be noted that the present invention is not limited to the following description, and it will be readily apparent to one skilled in the art that 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 construed as limited to the description of the following embodiments.

[0027] It should be noted that in the structures of the invention described below, identical sections or sections with similar functions are designated by the same reference numerals in different drawings, and descriptions of such sections will not be repeated. The same hatching pattern is used for sections with similar functions, and in some cases, the sections are not designated by specific reference numerals.

[0028] In addition, the position, size, area, or the like of each structure shown in drawings may not accurately represent the position, size, area, or the like in some cases for easy understanding. Therefore, the disclosed invention is not necessarily limited to the position, size, area, or the like disclosed in the drawings.

[0029] It should be noted that the terms "film" and "layer" can be used interchangeably depending on the situation or circumstances. For example, the term "conductive layer" can be replaced with the term "conductive film." As another example, the term "insulating film" can be replaced with the term "insulating layer." (Embodiment 1)

[0030] In this embodiment, an organic compound of one embodiment of the present invention is described. [Structure of an organic compound of one embodiment of the present invention]

[0031] An organic compound of one embodiment of the present invention is a tertiary amine. The ortho position of a biphenyl skeleton, a fluorene skeleton, and a terphenylene skeleton are bonded to the nitrogen of the amine. A carbazole skeleton is bonded to a phenylene group that is furthest from the nitrogen of the amine of the terphenylene skeleton.

[0032] A light-emitting device used in a high-temperature environment, such as a car, is required to have high heat resistance. Even in the case where a high temperature is applied during a product manufacturing process, such as during a sealing step using a glass frit, the light-emitting device is required to have high heat resistance. For these reasons, a material used for the light-emitting device is required to have a glass transition temperature (Tg) of 100°C or higher, or even 120°C or higher, in some cases. In one embodiment of the present invention, the Tg of the organic compound may be 100°C or higher, or even 120°C or higher; accordingly, a material suitable for a light-emitting device requiring high heat resistance can be provided.In many cases, light-emitting devices are manufactured by vacuum evaporation. In this case, materials used for the light-emitting devices should have high heat resistance and high sublimability. The sublimation temperature is preferably 500°C or lower, more preferably 400°C or lower. In one embodiment of the present invention, a material that has not only high heat resistance but also high sublimability can be provided, that is, a material that has high productivity in terms of device manufacturing can be provided.

[0033] The organic compound of one embodiment of the present invention has a high hole-transport property and a high electron-blocking property. The organic compound of one embodiment of the present invention can be used as a hole-transport material in the light-emitting device. 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 the light-emitting device. The light-emitting device can have high emission efficiency and high reliability by containing the organic compound of one embodiment of the present invention.

[0034] The organic compound of one embodiment of the present invention can be used as a charge transport material (hole transport material) in a light-receiving device such as an organic photodiode or a light-receiving and light-emitting device having both a light-receiving and a light-emitting function.

[0035] Specifically, one embodiment of the present invention is an organic compound represented by the general formula (G0). Note that not only organic compounds having the structures represented by the following general formulas, but also materials for light-emitting devices having the structures and materials for light-receiving devices having the structures are each an embodiment of the present invention.

[0036] In the general formula (G0), one of R 1 to R 5 represent the general formula (A); the others each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; R 6 to R 13 , R 23 to R 29 , R 31 to R 39 and R 41 to R 48 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; R 21 and R 22 each represent a methyl group.

[0037] Among organic compounds represented by the general formula (G0), organic compounds represented by the general formula (G1) are more preferred. A molecular structure in which a carbazolyl group is bonded to the para position of a terphenylene skeleton can increase the heat resistance of an organic compound compared to a molecular structure in which a carbazolyl group is bonded to the ortho or meta position of a terphenylene skeleton.

[0038] In the general formula (G1), R 2 to R 13 , R 23 to R 29 , R 31 to R 39 and R 41 to R 48 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; R21 and R 22 each represent a methyl group.

[0039] One of R 35 to R 39 preferably represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group. This can increase the heat resistance of the organic compound.

[0040] In the case where the 9-position of a fluorenyl group is hydrogen, the acidity of the hydrogen is increased, which could reduce the reliability of a light-emitting device; therefore, R 21 and R 22 , each located in the 9-position of a fluorenyl group, does not represent hydrogen but rather a methyl group.

[0041] R 21 and R 22 each represent a methyl group. This can increase the sublimability of the organic compound.

[0042] It is preferable that R41 to R 48 each independently represents hydrogen, a methyl group, a tert-butyl group, or a substituted or unsubstituted phenyl group in order to achieve high sublimability or high reliability.

[0043] Examples of the alkyl group having 1 to 6 carbon atoms in the general formulas (G0) and (G1) 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.

[0044] Examples of the cycloalkyl group having 3 to 6 carbon atoms in the general formulas (G0) and (G1) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0045] Examples of the substituted or unsubstituted aryl group having 6 to 13 carbon atoms in the general formulas (G0) and (G1) 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-fluoren]-yl group.

[0046] With regard to a “substituted or unsubstituted X” (X denotes a ring, a skeleton, a group, or the like) in the general formulas (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, or a hexyl group; a cycloalkyl group having 3 to 6 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopenyl group, or a cyclohexyl group; and an aryl group having 6 to 13 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, or a hexyl group. E.g. a phenyl group, a naphthyl group or a biphenyl group.

[0047] Specific examples of the compound of one embodiment of the present invention include organic compounds represented by structural formulas (100) to (246). Note that the present invention is not limited to these examples. Embodiments that do not fall within the scope of the claims are for illustrative purposes only and do not form part of the present invention. [Synthesis method of an organic compound of one embodiment of the present invention]

[0048] Various reactions can be applied to a synthesis method of an organic compound of one embodiment of the present invention. As an example, a method for synthesizing the organic compound represented by general formula (G0) is shown below. An example of a method for synthesizing the organic compound represented by general formula (G1) is described below.

[0049] In the general formula (G1) and the synthesis schemes shown below, R 2 to R 13 , R 23 to R 29 , R 31 to R 39 and R 41 to R 48 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R 21 and R22 each represent a methyl group. < <Syntheseverfahren 1 der organischen Verbindung, die durch die allgemeine Formel (G1) dargestellt wird> >

[0050] The organic compound represented by the general formula (G1) can be synthesized by a synthesis scheme (a-1) or a synthesis scheme (a-2) and a synthesis scheme (a-3).

[0051] First, as shown in the synthesis scheme (a-1), a 9-biphenyl-9H-carbazole compound (compound 1) and a dihalogenated benzene (compound 2) are coupled to obtain a halogenated 9-terphenyl-9H-carbazole compound (compound 3).

[0052] In the synthesis scheme (a-1) X 1 to 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.

[0053] In the case where a Suzuki-Miyaura coupling reaction using a palladium catalyst is carried out in the synthesis scheme (a-1), X 1 represents a halogen, represents one of X 2 and X 3 a boronic acid group or an organoboron group and the other represents a halogen or a triflate group. Iodine, bromine or chlorine are preferred as the halogen.

[0054] A palladium compound such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, or tetrakis(triphenylphosphine)palladium(0), and a ligand such as tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, or tri(ortho-tolyl)phosphine can be used in the reaction. An organic base such as sodium tert-butoxide, an inorganic base such as potassium carbonate, cesium carbonate, or sodium carbonate, or the like can be used in the reaction.

[0055] The solvent used in the reaction can be toluene, xylene, benzene, tetrahydrofuran, dioxane, ethanol, methanol, water, diethylene glycol dimethyl ether, ethylene glycol monomethyl ether, or the like. Reagents that can be used for the reaction are not limited to these.

[0056] As the reaction represented by the synthesis scheme (a-1), a Migita-Kosugi-Stille coupling reaction using an organotin compound, a Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, a Negishi coupling reaction using an organozinc compound, an Ullmann reaction using copper or a copper compound, or the like can also be carried out.

[0057] In the case where the Migita-Kosugi-Stille coupling reaction is used, one of X 2 and X 3 represents an organotin group and the other represents a halogen. This means that one of the compounds 1 and 2 is an organotin compound and the other is a halide.

[0058] In the case where the Kumada-Tamao-Corriu coupling reaction is used, one of X 2 and X 3represents a magnesium halide group and the other represents a halogen group. This means that one of the compounds 1 and 2 is a Grignard reagent and the other is a halide.

[0059] In the case where the Negishi coupling reaction is used, one of X 2 and X 3 represents an organozinc group and the other represents a halogen. This means that one of the compounds 1 and 2 is an organozinc compound and the other is a halide.

[0060] Alternatively, as shown in the synthesis scheme (a-2), a 9-phenyl-9H-carbazole compound (compound 4) and a biphenyl compound (compound 5) are coupled to obtain a halogenated 9-terphenyl-9H-carbazole compound (compound 3).

[0061] In the synthesis scheme (a-2) X 1 , X 4 and X 5each 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. Iodine, bromine or chlorine are preferred as the halogen.

[0062] As the reaction represented by the synthesis scheme (a-2), a Suzuki-Miyaura coupling reaction using a palladium catalyst, a Migita-Kosugi-Stille coupling reaction using an organotin compound, a Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, a Negishi coupling reaction using an organozinc compound, an Ullmann reaction using copper or a copper compound, or the like can be carried out. When these reactions are used, the description of the synthesis scheme (a-1) can be referred to for details.

[0063] Compound 3 can be used in combination with various diarylamine compounds for coupling reactions, thus making a significant contribution to facilitating and advancing material development. Furthermore, since compound 3 contains a halogen, compound 3 can be used as a source material not only for the amination reaction, but also for the Suzuki-Miyaura coupling reaction, the Migita-Kosugi-Stille coupling reaction, the Kumada-Tamao-Corriu coupling reaction, the Negishi coupling reaction, and the Ullmann reaction. This means that compound 3 can be widely used for coupling reactions to form a carbon-carbon bond, making it an effective and useful compound.

[0064] Next, as shown in the synthesis scheme (a-3), the compound 3 obtained in the synthesis scheme (a-1) or synthesis scheme (a-2) and a diarylamine compound (compound 6) are coupled, whereby the organic compound represented by the general formula (G1) can be obtained.

[0065] In the synthesis scheme (a-3) X 1 a halogen. Iodine, bromine or chlorine are preferred halogens.

[0066] As a reaction represented by synthesis scheme (a-3), a Buchwald-Hartwig amination reaction using a palladium catalyst can be carried out. A palladium compound such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), or allylpalladium(II) chloride (dimer) can be used as the palladium catalyst for the reaction. Tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)), or the like can be used as the ligand. An organic base such as sodium tert-butoxide, an inorganic base such as acetic acid, orPotassium carbonate, cesium carbonate, or sodium carbonate, or the like, can be used. Toluene, xylene, benzene, tetrahydrofuran, dioxane, or the like can be used as the solvent in the reaction. Note that the reagents that can be used in the reaction are not limited to these.

[0067] In the case where the Ullmann reaction is carried out in the synthesis scheme (a-3), copper or a copper compound can be used as a reagent, and an inorganic base such as potassium carbonate can be used as a base. Examples of the solvent that can be used in the reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, and benzene. In the Ullmann reaction, the target substance can be obtained in a shorter time and in a higher yield when the reaction temperature is 100°C or higher; therefore, DMPU or xylene, which have high boiling points, is preferably used. In addition, the reaction temperature is more preferably 150°C or higher; therefore, DMPU is more preferably used. Note that reagents that can be used in the reaction are not limited to this. < <Syntheseverfahren 2 der organischen Verbindung, die durch die allgemeine Formel (G1) dargestellt wird> >

[0068] The organic compound represented by the general formula (G1) can be synthesized by a synthesis scheme (b-1).

[0069] As shown in the synthesis scheme (b-1), a 9-biphenyl-9H-carbazole compound (compound 7) and a triarylamine compound (compound 8) are coupled, whereby the organic compound represented by the general formula (G1) can be obtained.

[0070] In the synthesis scheme (b-1) X 6 and X 7each 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. The halogen is preferably chlorine, bromine, or iodine; bromine or iodine is preferred in terms of reactivity, and chlorine or bromine is preferred in terms of cost.

[0071] As the reaction represented by the synthesis scheme (b-1), a Suzuki-Miyaura coupling reaction using a palladium catalyst, a Migita-Kosugi-Stille coupling reaction using an organotin compound, a Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, a Negishi coupling reaction using an organozinc compound, a reaction using copper or a copper compound, or the like can be carried out. When these reactions are used, the description of the synthesis scheme (a-1) can be referred to for details. < <Syntheseverfahren 3 der organischen Verbindung, die durch die allgemeine Formel (G1) dargestellt wird> >

[0072] The organic compound represented by the general formula (G1) can be synthesized by a synthesis scheme (c-1).

[0073] As shown in the synthesis scheme (c-1), a 9-phenyl-9H-carbazole compound (compound 9) and a triarylamine compound (compound 10) are coupled, whereby the organic compound represented by the general formula (G1) can be obtained.

[0074] In the synthesis scheme (c-1) X 8 and X 9 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. The halogen is preferably chlorine, bromine, or iodine; bromine or iodine is preferred in terms of reactivity, and chlorine or bromine is preferred in terms of cost.

[0075] As the reaction represented by the synthesis scheme (c-1), a Suzuki-Miyaura coupling reaction using a palladium catalyst, a Migita-Kosugi-Stille coupling reaction using an organotin compound, a Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, a Negishi coupling reaction using an organozinc compound, a reaction using copper or a copper compound, or the like can be carried out. When these reactions are used, the description of the synthesis scheme (a-1) can be referred to for details. < <Syntheseverfahren 4 der organischen Verbindung, die durch die allgemeine Formel (G1) dargestellt wird> >

[0076] The organic compound represented by the general formula (G1) can be synthesized by a synthesis scheme (d-1).

[0077] As shown in the synthesis scheme (d-1), a 9-terphenyl-9H-carbazole compound (Compound 11) and a biphenyl compound (Compound 12) are coupled to obtain a diarylamine compound (Compound 13). Subsequently, a fluorene compound (Compound 14) and Compound 13 are coupled to obtain the organic compound represented by the general formula (G1).

[0078] In the synthesis scheme (d-1), one of X 10 and X 11 represents an amino group and the other represents a halogen or a triflate group. X 12 represents a halogen or a triflate group. The halogen is preferably chlorine, bromine, or iodine; bromine or iodine is preferred in terms of reactivity, and chlorine or bromine is preferred in terms of cost.

[0079] As the reaction represented by the synthesis scheme (d-1), a Buchwald-Hartwig amination reaction using a palladium catalyst, an Ullmann reaction using copper or a copper compound, or the like can be carried out. When these reactions are used, reference can be made to the description of the synthesis scheme (a-3) for details. < <Syntheseverfahren 5 der organischen Verbindung, die durch die allgemeine Formel (G1) dargestellt wird> >

[0080] The organic compound represented by the general formula (G1) can be synthesized by a synthesis scheme (e-1).

[0081] As shown in the synthesis scheme (e-1), a 9-terphenyl-9H-carbazole compound (Compound 15) and a fluorene compound (Compound 16) are coupled to obtain a diarylamine compound (Compound 17). Subsequently, a biphenyl compound (Compound 18) and the diarylamine compound (Compound 17) are coupled to obtain an organic compound represented by the general formula (G1).

[0082] In the synthesis scheme (e-1), one of X 13 and X 14 represents an amino group and the other represents a halogen or a triflate group. X 15 represents a halogen or a triflate group. The halogen is preferably chlorine, bromine, or iodine; bromine or iodine is preferred in terms of reactivity, and chlorine or bromine is preferred in terms of cost.

[0083] As the reaction represented by the synthesis scheme (e-1), a Buchwald-Hartwig amination reaction using a palladium catalyst, an Ullmann reaction using copper or a copper compound, or the like can be carried out. When these reactions are used, reference can be made to the description of the synthesis scheme (a-3) for details.

[0084] The methods for synthesizing the organic compound of one embodiment of the present invention are described above; however, the present invention is not limited thereto, and another synthesis method may be employed.

[0085] The organic compound of one embodiment of the present invention has high heat resistance and high sublimability, and therefore, it is suitable for 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 a high hole-transport property and a high electron-blocking property and is suitable as a host material or a hole-transport material in a light-emitting device. A light-emitting device can have high emission efficiency by containing the organic compound of one embodiment of the present invention. The light-emitting device can have high reliability by containing the organic compound of one embodiment of the present invention.

[0086] This embodiment can be combined with the other embodiments as needed. In the case where a plurality of structural examples are shown in one embodiment in this specification, the structural examples can be combined as needed. (Embodiment 2)

[0087] In this embodiment, a light-emitting device of one embodiment of the present invention is described with reference to Fig. 1A to Fig. 1D. In this embodiment, a light-emitting device having a function of emitting visible light or near-infrared light is described. [Structural example of a light-emitting device]<<Grundlegende Struktur einer Licht emittierenden Vorrichtung> >

[0088] Fig. 1A to Fig. 1D illustrate examples of light-emitting devices that include an EL layer between a pair of electrodes.

[0089] The light-emitting device used in Fig. 1A has a structure in which an EL layer 103 is provided between a first electrode 101 and a second electrode 102 (a single structure). The EL layer 103 includes at least one light-emitting layer.

[0090] Fig. 1B illustrates an example of a multilayer structure of the EL layer 103. In this embodiment, an example is described in which the first electrode 101 serves as an anode and the second electrode 102 serves as a cathode. 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 arranged in this order above the first electrode 101. 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 each have a single-layer structure or a multilayer structure. In the case where the first electrode 101 serves as the cathode and the second electrode 102 serves as the anode, the arrangement order is reversed.

[0091] The light-emitting device may include a plurality of EL layers between the pair of electrodes. For example, it is preferable that the light-emitting device includes n EL layers (n is an integer greater than or equal to 2) and that a charge generation layer 104 is provided between an (n-1)th EL layer and an nth EL layer.

[0092] Fig. 1C illustrates a light-emitting device having a tandem structure in which two EL layers (103a and 103b) are provided between a pair of electrodes. Fig. Figure 1D illustrates a light-emitting device having a tandem structure in which three EL layers (103a, 103b, and 103c) are provided.

[0093] The EL layers 103a, 103b and 103c each include at least one light-emitting layer. In the case where a plurality of EL layers are formed as in the Fig. 1C or Fig. 1D, the EL layers may each have a multilayer structure similar to that of the tandem structure shown in Fig. 1B. EL layers 103a, 103b, and 103c may each include one or more of hole injection layer 111, hole transport layer 112, electron transport layer 114, and electron injection layer 115.

[0094] The charge generation layer 104 in Fig. 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 of the EL layers when a voltage is applied to the first electrode 101 and the second electrode 102. Therefore, the charge generation layer 104 injects electrons into the EL layer 103a and holes into the EL layer 103b when Fig. 1C, a voltage is applied to the first electrode 101 such that the potential of the first electrode 101 is higher than that of the second electrode 102.

[0095] Note that, in terms of light extraction efficiency, the charge generation layer 104 preferably transmits visible light or near-infrared light (specifically, the visible light or near-infrared light transmittance of the charge generation layer 104 is preferably 40% or higher). Furthermore, the charge generation layer 104 operates even if it has a lower conductivity than the first electrode 101 or the second electrode 102.

[0096] Note that the EL layers may be provided in contact with each other without providing the charge generation layer 104 therebetween if these EL layers allow the same structure as the charge generation layer 104 to be formed therebetween. For example, when a charge generation region is formed over a surface of an EL layer, another EL layer may be provided in contact with the surface.

[0097] A light-emitting device with a tandem structure has higher power efficiency than a light-emitting device with a single structure and requires less power when the devices emit light with the same luminance. Therefore, a light-emitting device with a tandem structure has a long lifetime, which can improve the reliability of a light-emitting device or electronic device.

[0098] The light-emitting layer 113 contains a light-emitting substance and a plurality of substances in a suitable combination so that fluorescence or phosphorescence with a desired wavelength can be obtained. The light-emitting layer 113 may have a multilayer structure composed of layers with different emission wavelengths. In this case, the light-emitting substances and other substances are different between the stacked light-emitting layers. Fig. 1C or Fig. The EL layers 103a, 103b, and 103c shown in Figure 1D can emit light at different wavelengths. In this case, too, the light-emitting substances and other substances between the stacked light-emitting layers are different. For example, in the structure shown in Fig. 1C, when the EL layer 103a emits red light and green light, and the EL layer 103b emits blue light, the light-emitting device emits white light as a whole. In a light-emitting device, a plurality of light-emitting layers or a plurality of EL layers may emit light of the same color. For example, in the structure in Fig. 1D, the light-emitting device can emit white light as a whole when the EL layer 103a emits first blue light, the EL layer 103b emits yellow light, yellow-green light, or green light and red light, and the EL layer 103c emits second blue light.

[0099] In the light-emitting device of one embodiment of the present invention, light emitted from the EL layer can be resonated between a pair of electrodes, so that the light is amplified. For example, an optical microresonator (microcavity) structure in which the first electrode 101 is a reflective electrode and the second electrode 102 is a transflective electrode is used. Fig. 1B is used, whereby light emitted from the EL layer 103 can be amplified.

[0100] By using the microcavity structure for the light-emitting device, light of different wavelengths (monochromatic light) can be extracted even when the same EL layer is used. Thus, forming functional layers for each pixel (so-called separate coloring) to obtain different emission colors is not necessary. Thus, high resolution can be easily achieved. Note that combination with color layers (color filters) is also possible. Furthermore, the emission intensity of light of a specific wavelength can be increased in the forward direction, thereby reducing power consumption.

[0101] Note that in the case where the first electrode 101 of the light-emitting device is a reflective electrode having a multilayer structure composed of a conductive film having a reflection property with respect to visible light or near-infrared light and a conductive film having a transmission property with respect to visible light or near-infrared light, optical matching can be performed by controlling the thickness of the conductive film having a transmission property. Specifically, when the wavelength of the light emitted from the light-emitting layer 113 is λ, the distance between the first electrode 101 and the second electrode 102 is preferably set to about mλ / 2 (m is a natural number).

[0102] In order to amplify desired light (wavelength: λ) emitted from the light-emitting layer 113, it is preferable to set the optical path length from the first electrode 101 to a region of the light-emitting layer 113 where the desired light is obtained (light-emitting region) and the optical path length from the second electrode 102 to the region of the light-emitting layer 113 where the desired light is obtained (light-emitting region) to approximately (2m'+1)λ / 4 (m' is a natural number), respectively. Here, the light-emitting region refers to a region of the light-emitting layer 113 where holes and electrons recombine.

[0103] By such optical adjustment, the spectrum of light emitted from the light-emitting layer 113 can be narrowed and light emission with high color purity can be obtained.

[0104] In this case, the optical path length between the first electrode 101 and the second electrode 102 is more specifically the total thickness from a reflection region in the first electrode 101 to a reflection region in the second electrode 102. However, it is difficult to accurately determine the reflection regions in the first electrode 101 and the second electrode 102; therefore, it is assumed that the above effect can be sufficiently achieved regardless of the location of the reflection regions in the first electrode 101 and the second electrode 102. Furthermore, the optical path length between the first electrode 101 and the light-emitting layer that emits the desired light is more specifically the optical path length between the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer that emits the desired light.However, it is difficult to accurately determine the reflection area in the first electrode 101 and the light-emitting area in the light-emitting layer that emits the desired light; therefore, it is assumed that the above effect can be sufficiently achieved no matter where the reflection area and the light-emitting area are located in the first electrode 101 and the light-emitting layer that emits the desired light, respectively.

[0105] The first electrode 101 and / or the second electrode 102 have / has a transmittance with respect to visible light or near-infrared light. The transmittance with respect to visible light or near-infrared light of the electrode with a transmittance with respect to visible light or near-infrared light is higher than or equal to 40%. In the case where the electrode with a transmittance with respect to visible light or near-infrared light is the transflective electrode described above, the reflectance with respect to visible light or near-infrared light of the electrode is higher than or equal to 20% and lower than or equal to 80%, preferably higher than or equal to 40% and lower than or equal to 70%. These electrodes preferably have a resistivity of 1 × 10 -2 Ωcm or lower.

[0106] When the first electrode 101 or the second electrode 102 is an electrode with a reflectivity with respect to visible light or near-infrared light (reflective electrode), the visible light or near-infrared light reflectance of the reflective electrode is higher than or equal to 40% and lower than or equal to 100%, preferably higher than or equal to 70% and lower than or equal to 100%. This electrode preferably has a specific resistance of 1 × 10 -2 Ωcm or lower. <<Spezifische Struktur der Licht emittierenden Vorrichtung> >

[0107] Next, a specific structure of the light-emitting device is described. Here, a light-emitting device with the single structure in Fig. 1B. <Erste Elektrode und zweite Elektrode>

[0108] As materials used for the first electrode 101 and the second electrode 102, any of the following materials can be used in a suitable combination as long as the functions of the two electrodes described above can be fulfilled. For example, a metal, an alloy, an electrically conductive compound, a mixture of these, and the like can be suitably used. Specifically, an In-Sn oxide (also referred to as ITO), an In-Si-Sn oxide (also referred to as ITSO), an In-Zn oxide, and an In-W-Zn oxide can be cited. In addition, it is possible to use a metal such asAluminum (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), or neodymium (Nd), or an alloy containing a suitable combination of any of these metals. It is also possible to use a Group 1 or Group 2 element of the periodic table not described above (e.g., a rare earth metal such as lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr), europium (Eu), or ytterbium (Yb)), an alloy containing a suitable combination of any of these, graphene, or the like.

[0109] Note that when manufacturing a light-emitting device with a microcavity structure, the first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a transflective electrode. Therefore, a single-layer structure or a multi-layer structure can be formed using one or more types of desired conductive materials. Note that the second electrode 102 is formed after the formation of the EL layer 103, and a material is selected as described above. A sputtering method or a vacuum evaporation method can be used to manufacture these electrodes. <Lochinjektionsschicht und Lochtransportschicht>

[0110] The hole injection layer 111 injects holes from the first electrode 101, which is an anode, into the EL layer 103 and contains a material having a high hole injection property.

[0111] As a material with a high hole injection property, for example, a transition metal oxide such as a molybdenum oxide, a vanadium oxide, a ruthenium oxide, a tungsten oxide or a manganese oxide, or a phthalocyanine-based compound such as phthalocyanine (abbreviation: H2Pc) or copper(II) phthalocyanine (abbreviation: CuPc) can be used.

[0112] As a material with a high hole injection property, an aromatic amine compound such as 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-(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) or 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

[0113] 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), or poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used as materials with high hole-injection properties. Alternatively, a high-molecular-weight compound to which an acid has been added can be used, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (abbreviation: PAni / PSS).

[0114] Alternatively, as a material with a high hole-injection property, a composite material containing a hole-transport material and an acceptor material (an electron-acceptor material) can be used. In this case, the acceptor material extracts electrons from a hole-transport material, so that holes are generated in the hole-injection layer 111, and the holes are injected into the light-emitting layer 113 through the hole-transport layer 112. Note that the hole-injection layer 111 can be formed to have a single-layer structure of a composite material containing a hole-transport material and an acceptor material, or it can be formed by stacking the respective layers of a hole-transport material and an acceptor material.

[0115] The hole-transport layer 112 transports the holes injected from the first electrode 101 through the hole-injection layer 111 to the light-emitting layer 113. The hole-transport layer 112 contains a hole-transport material. It is particularly preferred that the highest occupied molecular orbital (HOMO) level of the hole-transport material contained in the hole-transport layer 112 be the same as or close to that of the hole-injection layer 111.

[0116] As an acceptor material used for the hole-injection layer 111, an oxide of a metal belonging to any of 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 these, molybdenum oxide is particularly preferred because it is stable in air, has low hygroscopicity, and is easy to handle. Alternatively, organic acceptors such as a quinodimethane derivative, a chloranil derivative, and a hexaazatriphenylene derivative can be used.Examples of a compound containing an electron-withdrawing group (a halogen group or a 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), and 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ). In particular, a compound in which electron-withdrawing groups are bonded to a condensed aromatic ring containing a plurality of heteroatoms, such as HAT-CN, is preferred because of its thermal stability. A [3]radialene derivative having an electron-withdrawing group (especially a cyano group or a halogen group such as a fluorine group) has a very high electron-accepting property and is thus preferred.Specific examples include α,α',α''-1,2,3-cyclopropanetriylidene tris[4-cyano-2,3,5,6-tetrafluorobenzene acetonitrile], α,α',α''-1,2,3-cyclopropanetriylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzene acetonitrile] and α,α',α''-1,2,3-cyclopropanetriylidene tris[2,3,4,5,6-pentafluorobenzene acetonitrile].

[0117] The hole transport materials used for the hole injection layer 111 and the hole transport layer 112 are preferably substances with a hole mobility of greater than or equal to 10 -6 cm 2 / Vs. It should be noted that other substances can be used as long as the substances have a hole transport property that is higher than an electron transport property.

[0118] 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-transport material used for the hole-injection layer 111 and / or the hole-transport layer 112. Since the organic compound of one embodiment of the present invention has a high electron-blocking property, using the organic compound for the hole-transport layer 112 can improve the emission efficiency of the light-emitting device.

[0119] As the hole-transporting material, materials with a high hole-transport property, such as a π-electron-rich heteroaromatic compound (e.g., a carbazole derivative, a thiophene derivative, and a furan derivative) and an aromatic amine (a compound with an aromatic amine skeleton), are preferred.

[0120] Examples of the carbazole derivative (a compound having a carbazole skeleton) include a bicarbazole derivative (e.g., a 3,3'-bicarbazole derivative) and an aromatic amine having a carbazolyl group.

[0121] Specific examples of the bicarbazole derivative (e.g., a 3,3'-bicarbazole derivative) 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).

[0122] Specific examples of the aromatic amine 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-amine (abbreviation: PCBBiF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-Naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 4-Phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), 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), 3,6-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).

[0123] In addition to the above-mentioned compounds, other 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).

[0124] Specific examples of the thiophene derivative (a compound having a thiophene skeleton) and the furan derivative (a compound having a furan skeleton) include a compound having a thiophene skeleton, such as: E.g. 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) or 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).

[0125] Specific examples of the aromatic amine 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)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), 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 and DPA3B.

[0126] A high-molecular compound such as PVK, PVTPA, PTPDMA or Poly-TPD can also be used as a hole-transport material.

[0127] It should be noted that the hole transport material is not limited to the above examples, and one or a combination of various known materials can be used as the hole transport material for the hole injection layer 111 and the hole transport layer 112. <Licht emittierende Schicht>

[0128] The light-emitting layer 113 contains a light-emitting substance. The light-emitting layer 113 may contain one or more types of light-emitting substances. As the light-emitting substance, a substance whose emission color is blue, violet, blue-violet, green, yellow-green, yellow, orange, red, or the like is suitably used. Alternatively, a substance that emits near-infrared light may be used as the light-emitting substance. If a plurality of light-emitting layers are formed using different light-emitting substances, different emission colors can be exhibited (for example, complementary emission colors are combined to obtain white light emission). Furthermore, one light-emitting layer may contain different light-emitting substances.

[0129] The light-emitting layer 113 preferably contains, in addition to the light-emitting substance (a guest material), one or more types of organic compounds (e.g., a host material and an auxiliary material). As one or more types of organic compounds, the hole-transport material and / or the electron-transport material described in this embodiment can be used. Alternatively, a bipolar material can be used as one or more types of organic compounds.

[0130] In the case where the hole transport material is used for the light-emitting layer 113, the hole transport material is preferably the organic compound of one embodiment of the present invention.

[0131] There is no particular limitation on the light-emitting substances that can be used for the light-emitting layer 113, 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.

[0132] As an example of a light-emitting substance that converts singlet excitation energy into light emission, a substance that emits fluorescence (fluorescent material) can be cited. Examples include pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, and naphthalene derivatives. Pyrene derivatives are particularly preferred because they have a high emission 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(dibenzothiophen-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) and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03).

[0133] It is also possible to use 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)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-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-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-Diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-Diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) or the like.

[0134] Examples of a light-emitting substance that converts triplet excitation energy into light emission include a substance that emits phosphorescence (phosphorescent material) and a thermally activated delayed fluorescence (TADF) material that emits thermally activated delayed fluorescence.

[0135] Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. These substances exhibit their respective emission colors (emission peaks), and any one of them is thus appropriately selected and used according to the needs.

[0136] As examples of a phosphorescent material that displays blue or green and whose emission spectrum has a peak wavelength greater than or equal to 450 nm and less than or equal to 570 nm, the following substances can be given.

[0137] For example, organometallic complexes with a 4H-triazole framework, such as Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-ĸN 2]phenyl-ĸC}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: [Ir(iPrptz-3b)3]) and tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz)3]); organometallic complexes with a 1H-triazole framework, such as B. Tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]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 framework, such asfac-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 organometallic complexes in which a phenylpyridine derivative with an electron-withdrawing group is a ligand, such as 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: Flrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2'}iridium(III)picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) and bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' ]iridium(III)acetylacetonate (abbreviation: Flr(acac)).

[0138] As examples of a phosphorescent material that displays green or yellow and whose emission spectrum has a peak wavelength greater than or equal to 495 nm and less than or equal to 590 nm, the following substances can be given.

[0139] Examples of the phosphorescent material include organometallic iridium complexes having a pyrimidine skeleton, such as: B. 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: [Ir(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 with a pyrazine framework, 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)]); organometallic iridium complexes with a pyridine framework, such as B. Tris(2-phenylpyridinato-N,C 2' )iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium(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')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)]) and bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]; organometallic complexes, such as 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)]) and bis(2-phenylbenzothiazolato-N,C 2' )iridium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac)]); and a rare earth metal complex, such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]).

[0140] As examples of a phosphorescent material that displays yellow or red and whose emission spectrum has a peak wavelength greater than or equal to 570 nm and less than or equal to 750 nm, the following substances can be given.

[0141] For example, organometallic complexes with a pyrimidine framework, such as (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)]) and tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]); organometallic complexes with a pyrazine framework, 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)]), bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionatoκ 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]phenylκC}(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)]) and bis{4,6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinylκN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-m5CP)2(dpm)]); organometallic complexes with a pyridine framework, such as 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)]) and bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenylκC](2,4-pentanedionato-κ 2 O,O')iridium(III); platinum complexes, such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(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)]).

[0142] As compounds (host material and auxiliary material) used in the light-emitting layer 113, one or more types of substances having a larger energy gap than the light-emitting substance can be used.

[0143] In the case where the light-emitting substance used in the light-emitting layer 113 is a fluorescent material, an organic compound used in combination with the light-emitting substance is preferably an organic compound having a high energy level in a singlet excited state and a low energy level in a triplet excited state.

[0144] Regarding a preferable combination with a light-emitting substance (a fluorescent material or a phosphorescent material), specific examples of the organic compounds are shown below, although some of them overlap with the specific examples shown above.

[0145] In the case where the light-emitting substance is a fluorescent material, examples of the organic compound that can be used in combination with the light-emitting substance include condensed polycyclic aromatic compounds such as an anthracene derivative, a tetracene derivative, a phenanthrene derivative, a pyrene derivative, a chrysene derivative, and a dibenzo[g,p]chrysene derivative.

[0146] Specific examples of the organic compound used in combination with the fluorescent material 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-carbazol-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-diphenyl-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]chrysen-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]-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 and 5,12-bis(biphenyl-2-yl)tetracene.

[0147] In the case where the light-emitting substance is a phosphorescent material, an organic compound having triplet excitation energy (an energy difference between a ground state and a triplet excited state) higher than that of the light-emitting substance is selected as the organic compound used in combination with the light-emitting substance.

[0148] In the case where a plurality of organic compounds (e.g., a first host material and a second host material (or an auxiliary material)) are used to form an exciplex in combination with a light-emitting substance, the plurality of organic compounds are preferably mixed with a phosphorescent material (particularly, an organometallic complex).

[0149] With such a structure, light emission can be efficiently achieved by exciplex-triplet energy transfer (ExTET), which is energy transfer from an exciplex to a light-emitting substance. Note that a combination of the plurality of organic compounds that easily forms an exciplex is preferably used, and it is particularly preferable to combine a compound that can easily accept holes (hole-transport material) and a compound that can easily accept electrons (electron-transport material). The organic compound of one embodiment of the present invention described in Embodiment 1 is suitable for the compound that can easily accept holes. Specifically, any of the materials described in this embodiment can be used as the hole-transport material and the electron-transport material.With the above structure, high efficiency, low voltage operation and long lifetime of a light-emitting device can be achieved simultaneously.

[0150] In the case where the light-emitting substance is a phosphorescent material, examples of the organic compound that can be used in combination with the light-emitting substance include an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, a dibenzofuran derivative, a zinc- or aluminum-based metal complex, an oxadiazole derivative, a triazole derivative, a benzimidazole derivative, a quinoxaline derivative, a dibenzoquinoxaline derivative, a pyrimidine derivative, a triazine derivative, a pyridine derivative, a bipyridine derivative, and a phenanthroline derivative.

[0151] Among the compounds described above, specific examples of the aromatic amine (a compound having an aromatic amine skeleton), the carbazole derivative, the dibenzothiophene derivative (a thiophene derivative), and the dibenzofuran derivative (a furan derivative), which are organic compounds having a high hole-transporting property, are the same as the compounds given above as specific examples of the hole-transporting material.

[0152] Specific examples of zinc and aluminum-based metal complexes, which are organic compounds with a high electron transport property, include metal complexes with 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).

[0153] Alternatively, a metal complex with an oxazole-based ligand or a thiazole-based ligand, such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) or bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), can be used.

[0154] Specific examples of an oxadiazole derivative, a triazole derivative, a benzimidazole derivative, a quinoxaline derivative, a dibenzoquinoxaline derivative, and a phenanthroline derivative, which are organic compounds with a high electron transport property, 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)phenyl]-9H-carbazole (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), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: 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: 2mDBTPDBq-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).

[0155] Specific examples of a heterocyclic compound having a diazine skeleton, a heterocyclic compound having a triazine skeleton, and a heterocyclic compound having a pyridine skeleton, which are organic compounds with a high electron transport property, 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: 4,6mCzP2Pm), 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-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: 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-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).

[0156] As an organic compound with a high electron transport property, a high molecular compound such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can also be used.

[0157] The TADF material is a material that can upconvert a triplet excited state to a singlet excited state (i.e., reverse intersystem crossing is possible) using low thermal energy and efficiently emits light (fluorescence) from the singlet excited state. Thermally activated delayed fluorescence is efficiently obtained under the following condition: the energy difference between the triplet excitation level and the singlet excitation level is greater than or equal to 0 eV and less than or equal to 0.2 eV, preferably greater than or equal to 0 eV and less than or equal to 0.1 eV. It should be noted that delayed fluorescence from the TADF material refers to light emission that has the same spectrum as normal fluorescence and a very long lifetime. The lifetime is 10 -6 seconds or longer, preferably 10 -3 seconds or longer.

[0158] Examples of the TADF material include fullerene, a derivative thereof, an acridine derivative such as proflavin, and eosin. Other examples include a metal-containing porphyrin, such as a porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of the metal-containing porphyrin include a protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)), a mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), a hematoporphyrin-tin fluoride complex (abbreviation: SnF2(Hemato IX)), a coproporphyrin-tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III-4Me)), an octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(OEP)), an etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)) and an octaethylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP).

[0159] It is also possible to prepare a heterocyclic compound with a π-electron-rich heteroaromatic ring and a π-electron-poor heteroaromatic ring, such as 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: PPZ-3TPT), 3-(9,9-Dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS) or 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA).It should be noted that a substance in which a π-electron-rich heteroaromatic ring is directly bonded to a π-electron-poor heteroaromatic ring is particularly preferred because both the donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-poor heteroaromatic ring are improved and the energy difference between the singlet excited state and the triplet excited state becomes small.

[0160] It should be noted that the TADF material can also be used in combination with another organic compound. In particular, the TADF material can be used in combination with the host material, the hole-transport material, or the electron-transport material described above.

[0161] When the above materials are used in combination with a low-molecular material or a high-molecular material, they can be further used to form the light-emitting layer 113. For film formation, a known method (an evaporation method, a coating method, a printing method, or the like) can be appropriately used. <elektronentransportschicht>

[0162] The electron-transport layer 114 transports electrons injected through the electron-injection layer 115 from the second electrode 102 to the light-emitting layer 113. Note that the electron-transport layer 114 contains an electron-transport material. The electron-transport material contained in the electron-transport layer 114 is preferably a substance with an electron mobility greater than or equal to 1 × 10 -6 cm 2 / Vs. It should be noted that any other substance can be used as long as the substance transports electrons more easily than it transports holes.

[0163] As an electron transport material, for example, any of the following materials having a high electron transport property can be used: a metal complex having a quinoline skeleton, a metal complex having a benzoquinoline skeleton, a metal complex having an oxazole skeleton, a metal complex having a thiazole skeleton, an oxadiazole derivative, a triazole derivative, an imidazole derivative, an oxazole derivative, a thiazole derivative, a phenanthroline derivative, a quinoline derivative having a quinoline ligand, a benzoquinoline derivative, a quinoxaline derivative, a dibenzoquinoxaline derivative, a pyridine derivative, a bipyridine derivative, a pyrimidine derivative, and a π-electron-deficient heteroaromatic compound such as a nitrogen-containing heteroaromatic compound.

[0164] As specific examples of the electron transport material, the materials described above can be used. <elektroneninjektionsschicht>

[0165] The electron injection layer 115 is a layer containing a material with a high electron injection property. For the electron injection layer 115, an alkali metal, an alkaline earth metal, or a compound thereof, such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), or lithium oxide (LiO) may be used. x ), may be used. A rare earth metal compound such as erbium fluoride (ErF3) may also be used. Furthermore, an electride may be used for the electron injection layer 115. As an example of the electride, a substance in which electrons are added at a high concentration to calcium oxide-alumina is given. Any of the substances described above for forming the electron transport layer 114 may also be used.

[0166] Alternatively, a composite material containing an electron-transport material and a donor material (an electron-donor material) can be used for the electron-injection layer 115. Such a composite material has excellent electron-injection properties and electron-transport properties because electrons are generated in the organic compound by the electron donor. Here, the organic compound is preferably a material that can excellently transport the generated electrons; specifically, for example, the above-described electron-transport materials (e.g., a metal complex or a heteroaromatic compound) can be used for the electron-transport layer 114. As the electron donor, a substance that exhibits an electron-donor property with respect to an organic compound is used.In particular, an alkali metal, an alkaline earth metal, and a rare earth metal are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like are cited. Furthermore, an alkali metal oxide and an alkaline earth metal oxide are preferred, and lithium oxide, calcium oxide, barium oxide, and the like are cited. Alternatively, a Lewis base such as magnesium oxide may be used. As a further alternative, an organic compound such as tetrathiafulvalene (abbreviation: TTF) may be used. <ladungserzeugungsschicht>

[0167] In the light-emitting device in Fig. 1C, 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).

[0168] The charge generation layer 104 may contain a hole-transport material and an acceptor (electron-acceptor) material, or it may contain an electron-transport material and a donor material. The charge generation layer 104 with such components can suppress an increase in operating voltage caused by stacking the EL layers.

[0169] The materials described above can be used as hole transport material, acceptor material, electron transport material and donor material.

[0170] For manufacturing the light-emitting device described in this embodiment, a vacuum process such as an evaporation process or a solution process such as a spin coating process or an inkjet process can be used. When an evaporation process is used, a physical vapor deposition method (PVD method) such as a sputtering method, an ion plating method, an ion beam evaporation method, a molecular beam evaporation method, a vacuum evaporation method, a chemical vapor deposition method (CVD method), or the like can be used.Specifically, the functional layers (the hole injection layer, the hole transport layers, the light-emitting layer, the electron transport layers, and the electron injection layer) included in the EL layer and the charge generation layer can be formed by an evaporation method (e.g., a vacuum evaporation method), a coating method (e.g., a dip coating method, a die coating method, a bar coating method, a spin coating method, or a spray coating method), a printing method (e.g., an inkjet method, a screen printing (stencil printing), an offset printing (planographic printing), a flexographic printing (letter printing), a gravure printing, or a microcontact printing), or the like.

[0171] Materials of the functional layers and the charge generation layer included in the EL layer 103 are not limited to the respective materials described above. For example, a high-molecular compound (e.g., an oligomer, a dendrimer, and a polymer), a medium-molecular compound (a compound between a low-molecular compound and a high-molecular compound with a molecular weight of 400 to 4000), or an inorganic compound (e.g., a quantum dot material) can be used as the material of the functional layer. The quantum dot material can be a gelatinous quantum dot material, an alloyed quantum dot material, a core-shell quantum dot material, a core-quantum dot material, or the like.

[0172] This embodiment can be combined with the other embodiment as required. (Embodiment 3)

[0173] In this embodiment, light-emitting devices of embodiments of the present invention are described with reference to Fig. 2A to Fig. 2C, Fig. 3A to Fig. 3C, Fig. 4A and Fig. 4B and Fig. 5A to Fig. 5D described. [Structural Example 1 of a Light-Emitting Device]

[0174] Fig. 2A is a plan view of a light-emitting device, and Fig. 2B and Fig. 2C are cross-sectional views along the dashed lines X1-Y1 and X2-Y2 in Fig. 2A. The light-emitting device in Fig. 2A to Fig. 2C can be used, for example, as a lighting device. The light-emitting device can have a bottom-emission structure, a top-emission structure, or a dual-emission structure.

[0175] The Fig. The light-emitting device illustrated 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 may also be referred to as a light-emitting element, an organic EL element, a light-emitting device, or the like. The EL layer 402 preferably contains the organic compound of one embodiment of the present invention described in Embodiment 1. For example, the organic compound is preferably included as 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.

[0176] The organic EL device 450 includes the first electrode 401 over the substrate 490a, the EL layer 402 over the first electrode 401, and the second electrode 403 over the EL layer 402. The organic EL device 450 is sealed by the substrate 490a, the adhesive layer 407, and the substrate 490b.

[0177] End portions of the first electrode 401, the conductive layer 406, and the conductive layer 416 are covered with the 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, which is covered with the insulating layer 405 with the first electrode 401 interposed therebetween, serves as an auxiliary line and is electrically connected to the first electrode 401. The auxiliary line is preferably electrically connected to the electrode of the organic EL device 450, in which case, a voltage drop due to the resistance of the electrode can be prevented. The conductive layer 406 may be provided over the first electrode 401. Further, an auxiliary line electrically connected to the second electrode 403 may be provided, for example, over the insulating layer 405.

[0178] For the substrate 490a and the substrate 490b, glass, quartz, ceramic, sapphire, an organic resin, or the like can be used. If the substrate 490a and the substrate 490b are formed using a flexible material, the flexibility of the display device can be increased.

[0179] A light-emitting surface of the light-emitting device may be provided with a light extraction structure for increasing the light extraction efficiency, an antistatic film that prevents the adhesion of a foreign substance, a water-repellent film that suppresses the adhesion of contaminants, a hard film that suppresses generation of a scratch during use, a shock-absorbing layer, or the like.

[0180] Examples of insulating materials that can be used for the insulating layer 405 include a resin material such as an acrylic resin and an epoxy resin, and an inorganic insulating material such as silicon oxide, silicon oxynitride, silicon nitride oxide, silicon nitride, and aluminum oxide.

[0181] As the adhesive layer 407, various curing adhesives can be used, such as a reactive curing adhesive, a thermosetting adhesive, an anaerobic adhesive, and a light-curing adhesive such as a UV-curing adhesive. Examples of these adhesives include an epoxy resin, an acrylic resin, a silicone resin, a phenolic resin, a polyimide resin, an imide resin, a polyvinyl chloride (PVC) resin, a polyvinyl butyral (PVB) resin, and an ethylene-vinyl acetate (EVA) resin. In particular, a material with low moisture permeability, such as an epoxy resin, is preferred. A two-component resin may be used. An adhesive film or the like may be used.

[0182] The Fig. The light-emitting device shown in Fig. 2C includes a barrier layer 490c, the conductive layer 406, the conductive layer 416, the insulating layer 405, the organic EL device 450, the adhesive layer 407, the barrier layer 423, and the substrate 490b.

[0183] The Fig. The barrier layer 490c shown in Figure 2C includes a substrate 420, an adhesive layer 422, and an insulating layer 424 with a high barrier property.

[0184] At the Fig. In the light-emitting device shown in Fig. 2C, the organic EL device 450 is provided between the insulating layer 424 having a high barrier property and the barrier layer 423. Thus, even when resin films with relatively low water resistance or the like are used as the substrate 420 and the substrate 490b, contaminants such as water can be prevented from entering the organic EL device, that is, the lifetime can be prevented from being shortened.

[0185] For example, any of the following resins can be used for the substrate 420 and the substrate 490b: polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), a polyacrylonitrile resin, an acrylic resin, a polyimide resin, a polymethyl methacrylate resin, a polycarbonate (PC) resin, a polyethersulfone (PES) resin, polyamide resins (e.g., nylon and aramid), a polysiloxane resin, a cycloolefin resin, a polystyrene resin, a polyamideimide resin, a polyurethane resin, a polyvinyl chloride resin, a polyvinylidene chloride resin, a polypropylene resin, a polytetrafluoroethylene (PTFE) resin, an ABS resin, and cellulose nanofiber. Glass that is thin enough to exhibit flexibility can be used for the substrate 420 and the substrate 490b.

[0186] As the insulating layer 424 having a high barrier property, an inorganic insulating film is preferably used. For example, a silicon nitride film, a silicon oxynitride film, a silicon oxide film, a silicon nitride oxide film, an aluminum oxide film, or an aluminum nitride film can be used as the inorganic insulating film. Alternatively, 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 can be used. A stacked arrangement including two or more of the above insulating films can also be used.

[0187] The barrier layer 423 preferably includes at least a single-layer inorganic film. For example, the barrier layer 423 may have a single-layer structure of an inorganic film or a multi-layer structure of an inorganic film and an organic film. As the inorganic film, the above-described inorganic insulating film is preferably used. As the multi-layer structure, for example, a structure in which a silicon oxynitride film, a silicon oxide film, an organic film, a silicon oxide film, and a silicon nitride film are sequentially formed is given. When the barrier layer has a multi-layer structure of an inorganic film and an organic film, the intrusion of an impurity that might penetrate into the organic EL device 450 (typically hydrogen, water, or the like) can be suitably prevented.

[0188] The insulating layer 424 with a high barrier property and the organic EL device 450 can be formed directly on the substrate 420 with flexibility. In this case, the adhesive layer 422 is not necessary. Alternatively, the insulating layer 424 and the organic EL device 450 can be formed over a rigid substrate with a release layer interposed therebetween and then transferred to the substrate 420. For example, the insulating layer 424 and the organic EL device 450 can be transferred to the substrate 420 in the following manner: The insulating layer 424 and the organic EL device 450 are separated from the rigid substrate by applying heat, force, laser light, or the like to the release layer, and the insulating layer 424 and the organic EL device 450 are attached to the substrate 420 using the adhesive layer 422.For the separation layer, for example, a multilayer structure including inorganic films such as a tungsten film and a silicon oxide film, or an organic resin film made of polyimide or the like can be used. When a rigid substrate is used, the insulating layer 424 can be formed at a high temperature compared to the case where a resin substrate or the like is used, thus the insulating layer 424 can have a high density and excellent barrier properties. [Structural example 2 of a light-emitting device]

[0189] Fig. Figure 3A is a cross-sectional view of a light-emitting device. The Fig. The light-emitting device shown in Figure 3A is an active matrix light-emitting device in which a transistor is electrically connected to a light-emitting device.

[0190] The Fig. 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.

[0191] In Fig. 3A, the transistor 210 is provided over the substrate 201, the insulating layer 202 is provided over the transistor 210, and the light-emitting devices 203R, 203G, and 203B are provided over the insulating layer 202.

[0192] The transistor 210 and the light-emitting devices 203R, 203G, and 203B are sealed in a space 207 enclosed by the substrate 201, the substrate 205, and the adhesive layer 208. The space 207 can be filled with, for example, a reduced-pressure atmosphere, an inert atmosphere, or a resin.

[0193] In the Fig. In the light-emitting device shown in Figure 3A, a pixel includes a red subpixel (R), a green subpixel (G), and a blue subpixel (B).

[0194] The light-emitting device of one embodiment of the present invention includes a plurality of pixels arranged in a matrix. Each pixel includes at least one subpixel. A subpixel includes a light-emitting device. For example, a pixel may include three subpixels (e.g., three colors of R, G, and B, or three colors of yellow (Y), cyan (C), and magenta (M)) or four subpixels (e.g., four colors of R, G, B, and white (W), or four colors of R, G, B, and Y).

[0195] Fig. 3B illustrates specific structures 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 each include the same EL layer 213 and have microcavity structures in which the optical path length between electrodes of each light-emitting device is adjusted according to the emission color of the light-emitting device. The EL layer 213 preferably contains the organic compound of one embodiment of the present invention described in Embodiment 1. For example, the organic compound is preferably included as 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.

[0196] The first electrode 211 serves as a reflective electrode and the second electrode 215 serves as a transflective electrode.

[0197] In the light-emitting device 203R, the optical path length between the first electrode 211 and the second electrode 215 is set to an optical path length of 220R to increase the intensity of red light. Similarly, in the light-emitting device 203G, the optical path length between the first electrode 211 and the second electrode 215 is set to an optical path length of 220G to increase the intensity of green light. In the light-emitting device 203B, the optical path length between the first electrode 211 and the second electrode 215 is set to an optical path length of 220B to increase the intensity of blue light.

[0198] As in Fig. 3B, in the light-emitting device 203R, a conductive layer 212R is formed over the first electrode 211, and in the light-emitting device 203G, a conductive layer 212G is formed over the first electrode 211, whereby optical adjustment can be performed. Furthermore, in the light-emitting device 203B, the optical path length 220B can be adjusted by forming a conductive layer whose thickness differs from those of the conductive layer 212R and the conductive layer 212G over the first electrode 211. Note that, as shown in Fig. 3A, end portions of the first electrode 211, the conductive layer 212R and the conductive layer 212G are covered with an insulating layer 204.

[0199] The Fig. The light-emitting device shown in Figure 3A has a top-emission structure in which light received from the light-emitting devices is emitted through color filters formed on the substrate 205. The color filters each transmit visible light in a specific wavelength range and block visible light in a specific wavelength range.

[0200] In the red subpixel (R), light is emitted from the light-emitting device 203R via the red color filter 206R. As in Fig. 3A, the color filter 206R, which transmits only light in the red wavelength range, is provided at a position where it overlaps the light-emitting device 203R, whereby red light emission can be obtained from the light-emitting device 203R.

[0201] Similarly, in the green subpixel (G), light is emitted from the light-emitting device 203G via the green color filter 206G, and in the blue subpixel (B), light is emitted from the light-emitting device 203B via the blue color filter 206B.

[0202] Note that the substrate 205 may be provided with a black matrix 209 (also referred to as a black layer). In this case, the end portions of the color filters and the black matrix 209 preferably overlap each other. Furthermore, the color filters for the respective colors and the black matrix 209 may be covered with a covering layer that transmits visible light.

[0203] In the Fig. In the light-emitting device shown in Figure 3C, one pixel includes the red subpixel (R), the green subpixel (G), the blue subpixel (B), and a white subpixel (W). Fig. 3C, light is emitted from a light-emitting device 203W included in the white subpixel (W) to the outside of the light-emitting device without passing through a color filter.

[0204] It should be noted that the optical path length between the first electrode 211 and the second electrode 215 in the light-emitting device 203W may be the same as the optical path length in any of the light-emitting devices 203R, 203G, and 203B, or may be different from the optical path lengths in the light-emitting devices 203R, 203G, and 203B.

[0205] In the case where the intensity of blue light is to be enhanced, for example, in the case where light emitted from the light-emitting device 203W is white light with a low color temperature, the optical path length in the light-emitting device 203W is as shown in Fig. 3C, preferably equal to the optical path length 220B in the light-emitting device 203B. Therefore, light obtained from the light-emitting device 203W can be closer to white light with a desired color temperature.

[0206] Although Fig. 3A illustrates an example in which the same EL layer 213 is used for the light-emitting devices in the subpixels, as in Fig. 4A, different EL layers can be used for the light-emitting devices in the subpixels. The microcavity structure described above can also be applied to Fig. 4A should be applied.

[0207] Fig. 4A illustrates an example in which the light-emitting device 203R includes an EL layer 213R, the light-emitting device 203G includes an EL layer 213G, and the light-emitting device 203B includes an EL layer 213B. The EL layers 213R, 213G, and 213B may include a common layer. For example, in the EL layers 213R, 213G, and 213B, the structures of the respective light-emitting layers may be different, and the structures of the other layers may be the same. Fig. 4A, light from the light-emitting devices 203R, 203G, and 203B may be emitted through a color filter, or it may be emitted without passing through a color filter.

[0208] Although Fig. 3A illustrates a top-emission light-emitting device, is a light-emitting device having a bottom-emission structure in which light is extracted to the side of the substrate 201 on which the transistor 210 is formed, as in Fig. 4B, also an embodiment of the present invention.

[0209] In the bottom-emission light-emitting device, color filters for the respective colors are preferably provided between the substrate 201 and the light-emitting devices. Fig. 4B, the transistor 210 is formed over the substrate 201, an insulating layer 202a is formed over the transistor 210, the color filters 206R, 206G, and 206B are formed over the insulating layer 202a, an insulating layer 202b is formed over the color filters 206R, 206G, and 206B, and the light-emitting devices 203R, 203G, and 203B are formed over the insulating layer 202b.

[0210] In the case of the top-emission light-emitting device, an opaque substrate or a translucent substrate may be used as the substrate 201, and a translucent substrate may be used as the substrate 205.

[0211] In the case of the bottom emission light-emitting device, an opaque substrate or a translucent substrate may be used as the substrate 205, and a translucent substrate may be used as the substrate 201. [Structural Example 3 of the Light-Emitting Device]

[0212] The light-emitting device of one embodiment of the present invention may be a passive matrix device or an active matrix device. An active matrix light-emitting device is described by Fig. 5A to Fig. 5D described.

[0213] Fig. 5A is a plan view of the light-emitting device. Fig. 5B is a cross-sectional view taken along a dashed line AA' in Fig. 5A.

[0214] The light-emitting active matrix device in Fig. 5A and Fig. 5B includes a pixel section 302, a circuit section 303, a circuit section 304a, and a circuit section 304b.

[0215] Each of circuit sections 303, 304a, and 304b serves as a scan line driver circuit (gate driver) or a signal line driver circuit (source driver). Alternatively, each of circuit sections 303, 304a, and 304b may be a circuit that electrically connects pixel section 302 to an external gate driver or an external source driver.

[0216] A connecting line 307 is provided above a first substrate 301. The connecting line 307 is electrically connected to an FPC 308, which is an external input terminal. The FPC 308 transmits a signal (e.g., a video signal, a clock signal, a start signal, or a reset signal) or a potential from the outside to the circuit section 303, the circuit section 304a, and the circuit section 304b. The FPC 308 may be provided with a printed wiring board (PWB). Fig. 5A and Fig. The structure shown in Fig. 5B may also be referred to as a light-emitting module including a light-emitting device (or a light-emitting means) and an FPC.

[0217] The pixel section 302 includes a plurality of pixels, each including an organic EL device 317, a transistor 311, and a transistor 312. The transistor 312 is electrically connected to a first electrode 313 included in the organic EL device 317. The transistor 311 serves as a switching transistor. The transistor 312 serves as a current control transistor. Note that the number of transistors included in each pixel is not particularly limited and can be appropriately set as needed.

[0218] Circuit section 303 includes a plurality of transistors, such as a transistor 309 and a transistor 310. Circuit section 303 may be formed with a circuit including transistors of the same conductivity type (either n-channel transistors or p-channel transistors) or with a CMOS circuit including an n-channel transistor and a p-channel transistor. Furthermore, a driver circuit may be provided externally.

[0219] There is no particular limitation on the structure of the transistors included in the light-emitting device of this embodiment. For example, a planar transistor, a staggered transistor, or an inverted staggered transistor may be used. A top-gate transistor or a bottom-gate transistor may be used. Alternatively, gates may be provided above and below a semiconductor layer in which a channel is formed.

[0220] There is no particular limitation on the crystallinity of a semiconductor material used in the transistor, and an amorphous semiconductor or a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single-crystal semiconductor, or a semiconductor partially comprising crystal regions) can be used. Preferably, a semiconductor having crystallinity is used, in which case, deterioration of the transistor characteristics can be suppressed.

[0221] 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 (e.g., low-temperature polysilicon and single-crystal silicon).

[0222] For example, the semiconductor layer preferably contains indium, M (M is one or more species 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. Specifically, M is preferably one or more species selected from aluminum, gallium, yttrium, and tin.

[0223] For the semiconductor layer, an oxide containing indium (In), gallium (Ga) and zinc (Ga) (also called IGZO) is particularly preferably used.

[0224] In the case where the semiconductor layer is an In-M-Zn oxide, regarding the atomic ratio of metal elements in a sputtering target used to form the In-M-Zn oxide, it is preferable that the atomic proportion of In is greater than or equal to that of M. Examples of the atomic ratio of metal elements in such a sputtering target are as follows: 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; and In:M:Zn = 5:2:5.

[0225] The transistors included in circuit sections 303, 304a, and 304b and the transistors included in pixel section 302 may have the same structure or different structures. The plurality of transistors included in circuit sections 303, 304a, and 304b may have the same structure or two or more types of structures. Similarly, a plurality of transistors included in pixel section 302 may have the same structure or two or more types of structures.

[0226] One end portion of the first electrode 313 is covered with an insulating layer 314. The insulating layer 314 can be formed using 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. The insulating layer 314 preferably has a curved surface with a curve at its upper end portion or lower end portion. In this case, favorable coverage can be achieved with a film formed over the insulating layer 314.

[0227] 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 contains the organic compound of one embodiment of the present invention described in Embodiment 1. For example, the organic compound is preferably included as 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.

[0228] The plurality of transistors and the plurality of organic EL devices 317 are sealed with the first substrate 301, the second substrate 306, and the sealant 305. A space 318 enclosed by the first substrate 301, the second substrate 306, and the sealant 305 can be filled with an inert gas (e.g., nitrogen or argon) or an organic substance (including the sealant 305).

[0229] An epoxy resin, a glass frit, or the like can be used for the sealant 305. A material that allows as little moisture and oxygen permeation as possible is preferably used for the sealant 305. In the case where a glass frit is used for the sealant, the first substrate 301 and the second substrate 306 are preferably glass substrates for adhesion.

[0230] Fig. 5C and Fig. 5D illustrate examples of transistors that can be used in a light-emitting device.

[0231] One in Fig. Transistor 320 shown in Figure 5C includes a conductive layer 321 serving as a gate, an insulating layer 328 serving as a gate insulating layer, a semiconductor layer 327 including 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 serving as a gate insulating layer, a conductive layer 323 serving as a gate, and an insulating layer 324 covering the conductive layer 323. The insulating layer 328 is positioned between the conductive layer 321 and the channel formation region 327i. The insulating layer 325 is positioned 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.

[0232] Conductive layer 322a and conductive layer 322b are individually connected to low-resistance region 327n via openings in insulating layer 324. One of conductive layers 322a and 322b serves as the source, and the other serves as the drain.

[0233] The insulating layer 325 overlaps at least with the channel formation region 327i of the semiconductor layer 327. The insulating layer 325 may cover surfaces and side surfaces of the pair of low-resistance regions 327n.

[0234] One in Fig. Transistor 330 shown in Figure 5D includes a conductive layer 331 serving as a gate, an insulating layer 338 serving as a gate insulating layer, a conductive layer 332a and a conductive layer 332b serving as a source and drain, a semiconductor layer 337, an insulating layer 335 serving as a gate insulating layer, and a conductive layer 333 serving as a gate. Insulating layer 338 is positioned between conductive layer 331 and semiconductor layer 337. Insulating layer 335 is positioned between conductive layer 333 and semiconductor layer 337. Transistor 330 is preferably covered with an insulating layer 334. Insulating layer 334 may be included as a component of transistor 330.

[0235] Transistors 320 and 330 employ a structure in which the semiconductor layer forming a channel is sandwiched between two gates. The two gates can be connected together and supplied with the same signal to drive the transistor. Alternatively, the threshold voltage of the transistor can be controlled by applying a threshold voltage control potential to one of the two gates and applying an operating potential to the other gate.

[0236] A material through which impurities such as water and hydrogen do not easily diffuse is preferably used for at least one of the insulating layers covering the transistors. This is because such an insulating layer can serve as a barrier film. Such a structure can effectively suppress the diffusion of impurities from the outside into the transistors, thus increasing the reliability of the light-emitting device.

[0237] As each of the insulating layers 325, 326, 328, 334, 335, and 338, an inorganic insulating film is preferably used. For example, a silicon nitride film, a silicon oxynitride film, a silicon oxide film, a silicon nitride oxide film, an aluminum oxide film, or an aluminum nitride film can be used as the inorganic insulating film. Alternatively, 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 can be used. A stacked arrangement including two or more of the above insulating films can also be used.

[0238] As materials that can be used for the conductive layers in the light-emitting device, any of the metals such as aluminum, titanium, chromium, nickel, copper, yttrium, zirconium, molybdenum, silver, tantalum, and tungsten, an alloy containing any of these metals as its main component, or the like can be used. A single-layer structure or a multi-layer structure including a film containing any of these materials can be used. For example, the following structures can be used: a single-layer structure of an aluminum film containing silicon, a two-layer structure in which an aluminum film is arranged over a titanium film, a two-layer structure in which an aluminum film is arranged over a tungsten film, a two-layer structure in which a copper film is arranged over a copper-magnesium-aluminum alloy film,a two-layer structure in which a copper film is arranged over a titanium film; a two-layer structure in which a copper film is arranged over a tungsten film; a three-layer structure in which a titanium film or a titanium nitride film, an aluminum film or a copper film, and a titanium film or a titanium nitride film are arranged one above the other in this order; and a three-layer structure in which a molybdenum film or a molybdenum nitride film, an aluminum film or a copper film, and a molybdenum film or a molybdenum nitride film are arranged one above the other in this order. Note that an oxide such as indium oxide, tin oxide, or zinc oxide may be used. Copper containing manganese is preferably used because it increases shape controllability during etching.

[0239] This embodiment can be combined with the other embodiment as required. (Embodiment 4)

[0240] In this embodiment, electronic devices of an embodiment of the present invention will be described with reference to drawings.

[0241] Examples of electronic devices include a television set, a monitor of a computer or the like, a digital camera, a digital video camera, a digital photo frame, a mobile phone (also called a cellular phone or mobile telephone device), a portable game console, a portable information terminal, an audio playback device, a large gaming machine such as a pinball machine, a biometric identification device, and a verification device.

[0242] The electronic devices of one embodiment of the present invention each include the light-emitting device of one embodiment of the present invention in the display section and therefore have high light-emitting efficiency and high reliability.

[0243] The display section of the electronic device of this embodiment can display a video with a resolution of, for example, Full HD, 4K2K, 8K4K, 16K8K, or higher. Furthermore, the screen size of the display section can be greater than or equal to 20 inches, greater than or equal to 30 inches, greater than or equal to 50 inches, greater than or equal to 60 inches, or greater than or equal to 70 inches.

[0244] The electronic device of one embodiment of the present invention has flexibility and can therefore be integrated along a curved surface of an interior / exterior wall of a house or a building or along a curved surface of an interior / exterior of a vehicle.

[0245] Furthermore, the electronic device of one embodiment of the present invention may include a secondary battery. Preferably, the secondary battery can be charged by contactless energy transfer.

[0246] Examples of the secondary battery include a lithium-ion secondary battery such as a lithium polymer battery (lithium-ion polymer battery) using a gel electrolyte, a nickel-hydride battery, a nickel-cadmium battery, an organic radical battery, a lead-acid battery, an air secondary battery, a nickel-zinc battery, and a silver-zinc battery.

[0247] The electronic device of one embodiment of the present invention may include an antenna. When a signal is received from the antenna, the electronic device can display a video, data, or the like on a display section. If the electronic device includes the antenna and a secondary battery, the antenna can be used for contactless power transmission.

[0248] The electronic device of this embodiment may include a sensor (a sensor having a function of measuring force, displacement, position, speed, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, a chemical substance, sound, time, hardness, electric field, current, voltage, electric power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays).

[0249] The electronic device of this embodiment may have various functions. For example, the electronic device of this embodiment may have a function for displaying various data (a still image, a moving image, a text image, and the like) on the display section, a touchscreen function, a function for displaying a calendar, the date, time, and the like, a function for executing various types of software (programs), a wireless communication function, and a function for reading a program or data stored in a storage medium.

[0250] Fig. 6A illustrates an example of a television set. In a television set 7100, a display section 7000 is installed in a case 7101. Here, a structure is shown in which the case 7101 is supported by a stand 7103.

[0251] The light-emitting device of one embodiment of the present invention can be used for the display section 7000.

[0252] An operation of the Fig. Operation of the television 7100 shown in Figure 6A can be performed using an operation switch provided in the cabinet 7101 or a separate remote control 7111. Alternatively, the display section 7000 may include a touch sensor, and the television 7100 may be operated by touching the display section 7000 with a finger or the like. The remote control 7111 may be provided with a display section for displaying data output from the remote control 7111. Through operation buttons or a touchscreen in the remote control 7111, the television channels and volume can be controlled, and videos displayed on the display section 7000 can be controlled.

[0253] Note that the television set 7100 has a structure including a receiver, a modem, and the like. The receiver can receive general television broadcasts. When the television set is connected to a communication network via the modem, either wirelessly or wirelessly, unidirectional (from a transmitter to a receiver) or bidirectional (e.g., between a transmitter and a receiver, or between receivers) data communication can be performed.

[0254] Fig. 6B illustrates an example of a laptop PC. A laptop PC 7200 includes a case 7211, a keyboard 7212, a pointing device 7213, an external connection port 7214, and the like. The display section 7000 is installed in the case 7211.

[0255] The light-emitting device of one embodiment of the present invention can be used for the display section 7000.

[0256] Fig. 6C and Fig. 6D represent examples of digital signage.

[0257] One in Fig. The digital signage 7300 shown in Figure 6C includes a housing 7301, the display section 7000, a speaker 7303, and the like. Further, the digital signage may include an LED lamp, operation buttons (including a power button or an operation switch), a connection port, various sensors, a microphone, and the like.

[0258] Fig. 6D is a digital signage 7400 mounted on a cylindrical column 7401. The digital signage 7400 includes the display section 7000 provided along a curved surface of the column 7401.

[0259] The light-emitting device of one embodiment of the present invention can be used for the display section 7000 in Fig. 6C and Fig. 6D can be used.

[0260] A larger area of ​​the display section 7000 can increase the amount of data that can be provided at once. The larger display section 7000 attracts more attention, so that, for example, the effectiveness of advertising can be increased.

[0261] The use of a touchscreen in the display section 7000 is preferred because, in addition to displaying a still image or moving image on the display section 7000, intuitive operation by a user is possible. Furthermore, for an application for providing information such as route information or traffic information, user-friendliness can be improved through intuitive operation.

[0262] In addition, as in Fig. 6C and Fig. 6D, it is preferable that the digital signage 7300 or the digital signage 7400 can interact with an information terminal 7311 or an information terminal 7411, such as a smartphone, possessed by a user through wireless communication. For example, information of an advertisement displayed on the display section 7000 can be displayed on a screen of the information terminal 7311 or the information terminal 7411. By operating the information terminal 7311 or the information terminal 7411, a display on the display section 7000 can be switched.

[0263] It is possible to have the Digital Signage 7300 or the Digital Signage 7400 run a game using the screen of the Information Terminal 7311 or the Information Terminal 7411 as the controller. This allows an unlimited number of users to participate and enjoy the game simultaneously.

[0264] Fig. 7A to Fig. 7F illustrate examples of a portable information terminal including a flexible display section 7001.

[0265] The display section 7001 is manufactured using the light-emitting device of one embodiment of the present invention. For example, a light-emitting device that can be bent with a radius of curvature greater than or equal to 0.01 mm and less than or equal to 150 mm can be used. The display section 7001 can include a touch sensor so that the portable information terminal can be operated by touching the display section 7001 with a finger or the like.

[0266] Fig. 7A to Fig. 7C illustrates an example of a foldable, portable information terminal. Fig. 7A represents an unfolded state, Fig. 7B illustrates a state during translation from one unfolded state or one folded state to the other, and Fig. 7C illustrates a folded state of the portable information terminal 7600. The portable information terminal 7600 is highly portable when folded, and highly searchable due to a seamless large display area when unfolded.

[0267] The display section 7001 is supported by three housings 7601 connected to each other by hinges 7602. By folding a space between two housings 7601 with the hinges 7602, the shape of the portable information terminal 7600 can be reversibly changed from an unfolded state to a folded state.

[0268] Fig. 7D and Fig. 7E illustrates an example of a foldable, portable information terminal. Fig. Fig. 7D illustrates a portable information terminal 7650 folded so that the display section 7001 is on the inside, and Fig. 7E illustrates the portable information terminal 7650 folded so that the display portion 7001 is located on the outside. The portable information terminal 7650 includes the display portion 7001 and a non-display portion 7651. When the portable information terminal 7650 is not used, the portable information terminal 7650 is folded so that the display portion 7001 is located on the inside, thereby suppressing contamination or damage to the display portion 7001.

[0269] Fig. 7F illustrates an example of a wristwatch-like wearable information terminal. A wearable information terminal 7800 includes a band 7801, the display section 7001, an input / output port 7802, operation buttons 7803, and the like. The band 7801 functions as a housing. A flexible battery 7805 can be mounted on the wearable information terminal 7800. The battery 7805 can overlap, for example, with the display section 7001 or the band 7801.

[0270] The band 7801, the display section 7001, and the battery 7805 are flexible. Therefore, the portable information terminal 7800 can be easily bent to have a desired shape.

[0271] The control button 7803 can provide various functions, such as setting the time, turning the power on / off, turning wireless communication on / off, enabling / disabling sleep mode, and enabling / disabling a power-saving mode. For example, the functions of the control button 7803 can be arbitrarily set by the control system built into the portable information terminal 7800.

[0272] By touching an icon 7804 displayed on the display section 7001 with a finger or the like, an application can be started.

[0273] The 7800 portable information terminal enables short-range communication according to a communication standard. For example, two-way communication with a headset compatible with wireless communication enables hands-free phone calls.

[0274] The portable information terminal 7800 may include the input / output port 7802. When the input / output port 7802 is included, data can be directly transmitted to and received from another information terminal via a connector. Charging is also possible via the input / output port 7802. Note that charging of the portable information terminal exemplified in this embodiment may be performed by contactless power transfer without using the input / output port.

[0275] Fig. 8A is an exterior view of a 9700 vehicle. Fig. 8B illustrates a driver's seat of the vehicle 9700. The vehicle 9700 includes a body 9701, wheels 9702, a windshield 9703, headlights 9704, fog lights 9705, and the like. The light-emitting device of an embodiment of the present invention can be used, for example, in a display portion of the vehicle 9700. For example, the light-emitting device or the like of an embodiment of the present invention can be used for display portions 9710 to 9715 shown in Fig. 8B. Alternatively, the light-emitting device or the like of one embodiment of the present invention may be used in the headlights 9704 or the fog lights 9705.

[0276] The display portion 9710 and the display portion 9711 are display devices provided in a car windshield. The light-emitting device of one embodiment of the present invention may be a transparent device through which the opposite side can be seen by using a light-transmitting conductive material to form its electrodes and leads. Such a display portion 9710 or 9711 in a transparent state does not obstruct the driver's view when driving the vehicle 9700. Accordingly, the light-emitting device of one embodiment of the present invention may be provided in the windshield of the vehicle 9700. In the case where a transistor is provided for driving the light-emitting device, a transistor having a light-transmitting property, such as a transistor with a light-transmitting property, is used.an organic transistor using an organic semiconductor material or a transistor using an oxide semiconductor is preferably used.

[0277] The display section 9712 is a display device provided on a pillar section. For example, the display section 9712 can compensate for the view obstructed by the pillar section by displaying an image captured by an imaging unit provided in the body. The display section 9713 is a display device provided on the instrument panel. For example, the display section 9713 can compensate for the view obstructed by the instrument panel by displaying an image captured by an imaging unit provided in the body. This means that blind spots can be eliminated and safety can be enhanced by displaying an image captured by an imaging unit provided on the exterior of the vehicle.By displaying an image to compensate for the area a driver cannot see, the driver can easily and conveniently check safety.

[0278] Fig. 8C illustrates the interior of a car in which a bench seat is used as a driver's seat and a passenger's seat. A display portion 9721 is a display device provided in a door portion. For example, the display portion 9721 can compensate for the view obstructed by the door by displaying an image captured by an imaging unit provided in the body. A display portion 9722 is a display device provided in a steering wheel. A display portion 9723 is a display device provided in the center of a seat surface of the bench seat. On the seat surface, the backrest, or the like, the display device can be used as a seat warmer by using the heat generation of the display device as a heat source.

[0279] The display section 9714, the display section 9715, and the display section 9722 can provide various types of information by displaying navigation data, a speedometer, a tachometer, a mileage indicator, a fuel gauge, a gearshift indicator, the air conditioning setting, and the like. The content, layout, or the like of the display on the display sections can be freely changed by a user as needed. The above information can also be displayed on the display sections 9710 to 9713, the display section 9721, and the display section 9723. The display sections 9710 to 9715 and the display sections 9721 to 9723 can also be used as lighting devices. The display sections 9710 to 9715 and the display sections 9721 to 9723 can also be used as heating devices.

[0280] An electronic device according to one embodiment of the present invention has high emission efficiency and high reliability because the electronic device includes the light-emitting device according to one embodiment of the present invention as a light source. For example, the light-emitting device according to one embodiment of the present invention can be used for 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 of a lighting device.

[0281] Fig. 9A illustrates a biometric identification device that detects a finger vein and includes a housing 911, a light source 912, a detection stand 913, and the like. By placing a finger on the detection stand 913, an image of a shape of the finger vein can be captured. The light source 912, which emits near-infrared light, is provided above the detection stand 913, and an imaging device 914 is provided below the detection stand 913. The detection stand 913 contains a material that transmits near-infrared light. An image of near-infrared light emitted by the light source 912 and passing through the finger can be captured by the imaging device 914. Note that an optical system may be provided between the detection stand 913 and the imaging device 914.The device structure described above can be applied to a biometric identification device that detects a palm vein.

[0282] 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 configured to have a curved shape and can emit light uniformly with respect to a target. In particular, the light-emitting device preferably emits near-infrared light with the maximum peak intensity at a wavelength of 700 nm to 1200 nm. Light passing through a finger or palm is received, and its image is captured, allowing the position of the vein to be detected. This effect can be utilized for biometric identification. Furthermore, when combined with a global shutter system, the light-emitting device enables highly accurate detection even while the target is moving.

[0283] The light source 912 may include a plurality of light-emitting sections, such as in Fig. 9B. Light emitted from the light-emitting sections 915, 916, and 917 may have different wavelengths. Furthermore, the timing at which the light-emitting sections emit light may differ from each other. By changing the wavelengths and angles of light, different images can be successively captured, and a plurality of images can be used for identification, achieving high security.

[0284] Fig. 9C illustrates a biometric identification device that detects a palm vein and includes a housing 921, operation buttons 922, a detection section 923, a light source 924 that emits near-infrared light, and the like. By placing a hand over the detection section 923, a shape of the palm vein can be perceived. Furthermore, a security code or the like can be input using the operation buttons. The light source 924 is provided so as to surround the detection section 923 and irradiates a target (hand) with light. Then, light reflected from the target enters the detection section 923. The light-emitting device of one embodiment of the present invention can be used for the light source 924. An imaging device 925 is provided directly below the detection section 923 and can capture an image of the target (an entire image of the hand).Note that an optical system may be provided between the detection section 923 and the imaging device 925. The device structure described above can be applied to a biometric identification device that detects a finger vein.

[0285] Fig. 9D illustrates a non-destructive testing apparatus including 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. The light-emitting device of one embodiment of the present invention can be used for the light source 938. Inspection elements 936 are transported by the transport mechanism 933 to the position directly below the detection unit 935. The inspection element 936 is irradiated with near-infrared light from the light source 938, and an image of the light passing therethrough is captured by an imaging device 937 provided in the detection unit 935. The captured image is displayed on the monitor 934. Thereafter, the inspection elements 936 are transported to an exit of the housing 931, and a defective element is collected separately.Imaging using near-infrared light enables non-destructive and rapid detection of defective components within the inspection element, such as defects and foreign matter.

[0286] Fig. 9E illustrates a mobile phone device including a housing 981, a display portion 982, operation buttons 983, an external connection terminal 984, a speaker 985, a microphone 986, a first camera 987, a second camera 988, and the like. The display portion 982 of the mobile phone device includes a touch sensor. The housing 981 and the display portion 982 have flexibility. All operations, including making a call and entering text, can be performed by touching the display portion 982 with a finger, a stylus, or the like. The first camera 987 can capture a visible light image, and the second camera 988 can capture an infrared light image (a near-infrared light image). The mobile phone device or the display portion 982 in Fig. 9E may include the light emitting device of an embodiment of the present invention.

[0287] This embodiment can be combined with the other embodiment as required. [Example 1](Synthesis Example 1)

[0288] This example describes a method for synthesizing an organic compound of 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) of Embodiment 1.

[0289] 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 added to a 200 mL three-necked flask equipped with a reflux tube. The air in 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. Degassing under reduced pressure and replacement of the air in the system with nitrogen were performed three times. 21 mg (37 µmol) of bis(dibenzylideneacetone)palladium(0) was added to the system, and the mixture was stirred at 150 °C for 10 hours. After stirring, an insoluble substance was removed from the mixture by suction filtration. Water was added to the resulting filtrate, so that an aqueous layer was subjected to extraction with toluene.The resulting organic layer was washed twice with water and then with a saturated saline solution. The organic layer was dried with magnesium sulfate. The resulting mixture was gravity filtered to remove the magnesium sulfate. The resulting filtrate was concentrated to obtain 2.6 g of a yellow viscous solid. The resulting solid was purified by silica gel chromatography (eluent containing toluene and hexane in a ratio of 1:2). The resulting pale yellow solid was recrystallized from toluene to afford 0.83 g of a pale yellow solid in a yield of 30%.

[0290] By a train sublimation method, 0.83 g of the obtained solid was purified. In the sublimation purification, the solid was heated at 320°C for 16 hours under a pressure of 3.8 Pa at an argon flow rate of 15 ml / min. After the sublimation purification, 0.55 g of a pale yellow target solid with a collection rate of 66% was obtained. In the sublimation purification, the material was sublimated by heating at 320°C, and the collection rate was as high as 66%, indicating that the organic compound of one embodiment of the present invention had high sublimability and no problem with the evaporation process. A synthesis scheme (A-1) is shown below.

[0291] Analysis results by nuclear magnetic resonance ( 1 H-NMR spectroscopy of the obtained pale yellow solid is shown below. The results indicate that oYGTBiF(2), represented by structural formula (100), was obtained in this example.

[0292] 1 H-NMR (dichloromethane-d2, 300 MHz): δ = 8.17 (d, J = 7.8 Hz, 2H), 7.91 (d, J = 8.7 Hz, 2H), 7.78 (d, J = 8.7 Hz, 2H), 7.71 (d, J = 8.7 Hz, 2H), 7.67 (d, J = 8.7 Hz, 2H), 7.57 (d, J = 7.2 Hz, 1H), 7.52-7.19 (m, 18H), 7.14-7.06 (m, 5H), 6.92 (d, J = 1.8 Hz, 1H), 6.79 (dd, J1 = 6.0 Hz, J2 = 2.1 Hz, 1H), 1.30 (s, 6H).

[0293] Next, UV-VIS absorption spectra (hereinafter referred to simply as "absorption spectra") and emission spectra of oYGTBiF(2) in a toluene solution and a solid thin film of oYGTBiF(2) were measured. The solid thin film was formed over a quartz substrate by a vacuum evaporation method.

[0294] The absorption spectra were measured using UV-VIS spectrophotometers (solution: V-550, manufactured by JASCO Corporation, thin film: U-4100, manufactured by Hitachi High-Technologies Corporation). To calculate the absorption spectrum of oYGTBiF(2) in a toluene solution, the absorption spectrum of toluene placed in a quartz cell was measured and then subtracted from the absorption spectrum of the toluene solution of oYGTBiF(2) placed in a quartz cell. The absorption spectrum of the thin film was calculated using an absorbance (-log 10 [%T / (100-%R)]), which was calculated from the transmittance and reflectance of the thin film including the substrate. Note that %T represents transmittance and %R represents reflectance. The emission spectra were measured using a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK). Note that absorption spectra and emission spectra were measured at room temperature.

[0295] Fig. Figure 10A shows the absorption and emission spectra obtained for the toluene solution. The horizontal axis represents the wavelength, and the vertical axes represent the absorption intensity and emission intensity.

[0296] As in Fig. As shown in Figure 10A, an absorption peak of oYGTBiF(2) in the toluene solution was observed at about 366 nm, and an emission peak thereof was observed at about 421 nm (excitation wavelength: 366 nm).

[0297] Fig. Figure 10B shows the absorption and emission spectra of the obtained solid thin film. The horizontal axis represents the wavelength, and the vertical axes represent the absorption intensity and emission intensity.

[0298] As in Fig. As shown in Figure 10B, absorption peaks of oYGTBiF(2) in a solid thin film were observed at about 294 nm, 350 nm, and 367 nm, and an emission peak thereof was observed at about 440 nm (excitation wavelength: 365 nm).

[0299] It has been found that the organic compound of one embodiment of the present invention, oYGTBiF(2), is a host material suitable for a fluorescent material that emits blue light or light with energy at a longer wavelength than blue light, and a phosphorescent material that emits green light or light with energy at a longer wavelength than green light. Furthermore, oYGTBiF(2) can be used as a host material used with a light-emitting substance in the visible or near-infrared region (e.g., a fluorescent material, a delayed fluorescent material, or a phosphorescent material), or as a light-emitting substance.

[0300] Next, the HOMO and LUMO levels of oYGTBiF(2) were obtained by cyclic voltammetry (CV) measurements. The calculation method is shown below.

[0301] An electrochemical analyzer (ALS Model 600A or 600C, manufactured by BAS Inc.) was used as the measurement device. A solution for CV measurement was prepared as follows: Tetra-n-butylammonium perchlorate (n-Bu4NClO4, manufactured by Tokyo Chemical Industry Co., Ltd., Catalog No. T0836) as the supporting electrolyte was dissolved in anhydrous dimethylformamide (DMF, manufactured by Sigma-Aldrich Co. LLC., 99.8%, Catalog No. 22705-6) as the solvent at a concentration of 100 mmol / L, and the object to be measured was dissolved therein at a concentration of 2 mmol / L.

[0302] A platinum electrode (PTE platinum electrode, manufactured by BAS Inc.) was used as the working electrode, another platinum electrode (Pt counter electrode for VC-3 (5 cm), manufactured by BAS Inc.) was used as the auxiliary electrode, and an Ag / Ag + An electrode (RE7 non-aqueous solvent reference electrode, manufactured by BAS Inc.) was used as the reference electrode. Note that the measurement was performed at room temperature (20 °C to 25 °C).

[0303] Additionally, the scanning speed during the CV measurement was set to 0.1 V / s, and an oxidation potential Ea [V] and a reduction potential Ec [V] with respect to the reference electrode were measured. The potential Ea is an intermediate potential of an oxidation-reduction wave, and the potential Ec is an intermediate potential of a reduction-oxidation wave. It was found that the potential energy of the reference electrode used in this example is -4.94 [eV] with respect to the vacuum level, and therefore the HOMO level and the LUMO level can be obtained by the following formula: HOMO level [eV] = -4.94 - Ea and LUMO level [eV] = -4.94 - Ec.

[0304] Furthermore, the CV measurement was repeated 100 times, and the oxidation-reduction wave after the hundredth cycle was compared with the oxidation-reduction wave after the first cycle to investigate the electrical stability of the compound.

[0305] As a result, when measuring the oxidation potential Ea [V] of oYGTBiF(2), the HOMO level was -5.42 eV. On the other hand, when measuring the reduction potential Ec [V], the LUMO level was -2.31 eV. Accordingly, it was found that oYGTBiF(2) exhibits a strong electron-blocking property. When the oxidation-reduction wave was repeatedly measured in the Ea measurement, the peak intensity of the oxidation-reduction wave after the 100th cycle remained at 88% of that of the oxidation-reduction wave in the first cycle; and in the Ec measurement, the peak intensity of the oxidation-reduction wave after the 100th cycle remained at 99% of that of the oxidation-reduction wave in the first cycle. Consequently, the resistance to oxidation and reduction of oYGTBiF(2) was found to be very high.

[0306] Differential scanning calorimetry (DSC) was performed on oYGTBiF(2) using Pyris1DSC, manufactured by PerkinElmer, Inc. In the differential scanning calorimetry, after raising the temperature from -10 °C to 320 °C at a temperature increase rate of 40 °C / min, the temperature was maintained for 1 minute and then lowered to -10 °C at a temperature decrease rate of 100 °C / min. This process was repeated twice consecutively. From the second-cycle DSC measurement result, it was determined that the glass transition point of oYGTBiF(2) is 137 °C, indicating that oYGTBiF(2) is a substance with very high heat resistance.

[0307] Differential thermal analysis was performed on oYGTBiF(2). The measurement was carried out using a high-vacuum differential thermal balance (TG-DTA2410SA, manufactured by Bruker AXS KK). The measurement was carried out under atmospheric pressure at a temperature elevation rate of 10 °C / min under a nitrogen stream (flow rate: 200 mL / min). In the differential thermal analysis, the temperature at which the thermogravimetric weight decreased by 5% of the initial weight (decomposition temperature) was found to be 484 °C, indicating that oYGTBiF(2) is a substance with high thermal stability.

[0308] From the above results, it was found 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 (a light-emitting device and a light-receiving device) with high heat resistance and increase the productivity of device manufacturing. [Example 2]

[0309] In this example, a light-emitting device of one embodiment of the present invention is manufactured and evaluated, and the evaluation results are described.

[0310] In this example, a device 1 using oYGTBiF(2) (structural formula (100)) described in Example 1, a comparative device 2, a comparative device 3, and a comparative device 4 were fabricated and evaluated as light-emitting devices. The results are described.

[0311] Fig. Figure 11 shows the structures of the four light-emitting devices used in this example, and Table 1 shows specific structures. The chemical formulas of materials used in this example are shown below. [Table 1] ersteElektrode Lochinjektionsschicht Lochtransportschicht Licht emittierendeSchicht Elektronentransportschicht Elektroneninjektionsschicht zweiteElektrode 801 811 812 813 814 815 803 Vorrichtung1 ITSO(70 nm) oYGTBiF(2):ALD-MP001Q(1:0,1, 10 nm) oYGTBiF(2)(20 nm) DBfBB1TP(10 nm) cgDBCzPA:3,10PCA2Nbf(IV)-02(1:0,015,25 nm) cgDBCzPA(15 nm) NBPhen(10 nm) LiF(1 nm) Al(200 nm) Vergleichsvorrichtung 2 oYGBBiF:ALD-MP001Q(1:0.1, 10nm) oYGBBiF(20 nm) Comparison device 3 oYGTBi1BP:ALD-MP001Q(1:0.1, 10nm) oYGTBi1BP(20 nm) Comparison device 4 YGTBiF(2):ALD-MP001Q(1:0.1, 10nm) YGTBiF(2)(20 nm) <<Herstellung der Licht emittierenden Vorrichtungen> >

[0312] In each of the light-emitting devices described in this example, as in Fig. 11, a first electrode 801 is formed over a substrate 800; 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 constituting an EL layer 802 are disposed in this order over the first electrode 801; and a second electrode 803 is disposed over the electron injection layer 815.

[0313] First, the first electrode 801 was formed over the substrate 800. The electrode area was set to 4 mm 2 (2 mm × 2 mm). A glass substrate was used as the substrate 800. The first electrode 801 was formed by a sputtering method using indium tin oxide containing silicon oxide (ITSO) to a thickness of 70 nm. Note that in this example, the first electrode 801 serves as the anode.

[0314] For pretreatment, one surface of the substrate was washed with water, baked at 200 °C for one hour, and then UV ozone treatment was performed for 370 seconds. Afterward, the substrate was transferred to a vacuum evaporation device, where the pressure was reduced to approximately 10 -4 Pa, vacuum baking was performed at 170 °C for 30 minutes in a heating chamber of the vacuum evaporation device, and then the substrate was cooled for approximately 30 minutes.

[0315] Next, the hole injection layer 811 was formed over the first electrode 801. The hole injection layer 811 was formed such that the pressure in the vacuum evaporator was 10 -4 Pa, and then a material X and ALD-MP001Q (manufactured by Analysis Atelier Corporation, material serial number 1S20180314) were co-evaporated to a thickness of 10 nm at a weight ratio of material X:ALD-MP001Q = 1:0.1. Note that ALD-MP001Q is an acceptor material.

[0316] Next, the hole-transport layer 812 was formed over the hole-injection layer 811. The hole-transport layer 812 was formed by evaporating material X to a thickness of 20 nm and depositing N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-aminop-terphenyl (abbreviation: DBfBB1TP) to a thickness of 10 nm.

[0317] As material X in the hole injection layer 811 and the hole transport layer 812, 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 for device 1, 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: oYGBBiF) was used for the comparison device 2, 2,4'-Diphenyl-4''-[4'-(9H-carbazol-9-yl)-1,1'-biphenyl-4-yl]triphenylamine (abbreviation: oYGTBi1BP) was used for comparative device 3 and 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 for comparative device 4.

[0318] Next, the light-emitting layer 813 was formed over the hole-transport layer 812 as follows: 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 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)-O2), used as the guest material (fluorescent material), were deposited by co-evaporation in a weight ratio of cgDBCzPA:3,10PCA2Nbf(IV)-O2 = 1:0.015. The thickness was set to 25 nm.

[0319] Next, the electron-transport layer 814 was formed over the light-emitting layer 813. The electron-transport layer 814 was formed in the following manner: cgDBCzPA was deposited by evaporation to a thickness of 15 nm, and 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) was deposited by evaporation to a thickness of 10 nm.

[0320] Subsequently, the electron injection layer 815 was formed over the electron transport layer 814. Lithium fluoride (LiF) was deposited as the electron injection layer 815 by evaporation to a thickness of 1 nm.

[0321] Next, the second electrode 803 was formed over the electron injection layer 815. Aluminum was deposited as the second electrode 803 by evaporation to a thickness of 200 nm. In this example, the second electrode 803 serves as the cathode.

[0322] Through the above steps, the light-emitting device including the EL layer 802 between the pair of electrodes was formed over the 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 above are functional layers constituting the EL layer in the light-emitting device of one embodiment of the present invention. Furthermore, in all the evaporation steps of the above manufacturing method, evaporation was performed by a resistance heating method.

[0323] The light-emitting device manufactured as described above was sealed using another substrate (not shown) in the following manner. The substrate (not shown), to which a UV-curing sealant had been applied, was fixed to the substrate 800 in a glove box containing a nitrogen atmosphere, and the substrates were bonded together such that the sealant was applied to enclose the light-emitting device over the substrate 900. During the sealing process, the sealant was cured with 365 nm UV light at 6 J / cm 2 irradiated to solidify, and the sealant was heat treated at 80 °C for one hour to stabilize. <<Betriebseigenschaften der Licht emittierenden Vorrichtungen> >

[0324] The operating characteristics of the light-emitting devices fabricated in this example were measured. Note that the measurements were conducted at room temperature.

[0325] Fig. Figure 12 shows the luminance-power efficiency characteristics of the light-emitting devices. Fig. Figure 13 shows the voltage-luminance characteristics of the light-emitting devices. Fig. Figure 14 shows the voltage-current characteristics of the light-emitting devices. Fig. Figure 15 shows the luminance-external quantum efficiency characteristics of the light-emitting devices.

[0326] Table 2 lists the initial values ​​of main properties of the light-emitting devices at about 1000 cd / m 2 . [Table 2] Voltage (V) Current (mA) Current density (mA / cm 2 ) Chromaticity(x,y) Luminance (cd / m 2 ) Power efficiency (cd / A) Power efficiency (lm / W) external quantum efficiency (%) Energy efficiency (%) Device1 3,0 0,40 10,0 (0,14, 0,14) 1110 11,2 11,7 10,6 9,1 Comparison device 2 3,2 0,43 10,7 (0,14, 0,13) 1160 10,9 10,7 10,8 8,8 Comparison device 3 3,0 0,54 13,5 (0,14, 0,11) 1150 8,5 8,9 9,1 7,9 Comparison device 4 3,1 0,33 8,2 (0,14, 0,13) 940 11,4 11,5 11,0 9,2

[0327] As in Fig. 12 to Fig. As shown in Figure 15 and Table 2, Device 1, Comparative Device 2, and Comparative Device 4 exhibit high emission efficiency. Furthermore, Device 1 exhibits higher emission efficiency than Comparative Device 3.

[0328] Fig. Figure 16 shows the emission spectra at the time when the light-emitting devices were supplied with a current at a current density of 12.5 mA / cm 2 As in Fig. As shown in Figure 16, the emission spectrum of Device 1 has a maximum peak at about 459 nm, which originates from 3,10PCA2Nbf(IV)-O2 contained in the light-emitting layer 813. Similarly, the emission spectra of Comparative Device 2, Comparative Device 3, and Comparative Device 4 have maximum peaks at about 458 nm, 457 nm, and 459 nm, respectively.

[0329] Next, reliability tests were performed on the light-emitting devices. Fig. 17A and Fig. 17B shows the results of the reliability tests. In Fig. 17A, the vertical axis represents the normalized luminance (%) assuming that the initial luminance is 100%, and the horizontal axis represents the operating time (h). Fig. 17B, ​​the vertical axis represents the voltage change (ΔV) from the initial voltage (when the operating time is 0) and the horizontal axis represents the operating time (h). In the reliability tests, the light-emitting devices were operated at a current density of 50 mA / cm 2 operated.

[0330] 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.

[0331] Accordingly, it is determined that the device 1 has equivalent emission efficiency and high reliability compared to the comparison device 2 and the comparison device 4. Furthermore, the device 1 has high emission efficiency and equivalent reliability compared to the comparison device 3.

[0332] oYGTBiF(2) used for Device 1 is a tertiary amine. The ortho position of a biphenyl skeleton, a fluorene skeleton, and a terphenylene skeleton are bonded to the amine nitrogen. A carbazole skeleton is bonded to a phenylene group that is farthest from the amine nitrogen of the terphenylene skeleton. This means that the amine nitrogen is bonded to the carbazole nitrogen via the terphenylene skeleton. On the other hand, oYGBBiF used for Comparative Device 2 differs from oYGTBiF(2) used for Device 1 in that the carbazole nitrogen and the amine nitrogen are bonded via a biphenylene skeleton rather than via the terphenylene skeleton. Furthermore, oYGTBi1BP, used for comparison device 3, differs from oYGTBiF(2) in that not the fluorene skeleton but the para position of a biphenyl skeleton is bonded to nitrogen of the amine.YGTBiF(2), used for Comparative Device 4, differs from oYGTBiF(2) in that the para position of the biphenyl skeleton, rather than the ortho position of the biphenyl skeleton, is bonded to the nitrogen of the amine. Accordingly, the emission efficiency and reliability of the light-emitting device can be increased by using the organic compound that is a tertiary amine. In the tertiary amine, the ortho position of the biphenyl skeleton, a fluorene skeleton, and a terphenylene skeleton are bonded to the nitrogen of the amine; and a carbazole skeleton is bonded to a phenylene group of the terphenylene skeleton that is farthest from the nitrogen of the amine. [Example 3]

[0333] In this example, light-emitting devices of one embodiment of the present invention are manufactured and evaluated, and the evaluation results are described.

[0334] In this example, a device 5 and a device 6 using oYGTBiF(2) (structural formula (100)) described in Example 1 were fabricated and evaluated as light-emitting devices. The results are described.

[0335] Table 3 shows specific structures of the two light-emitting devices used in this example. Device 5 has a similar structure to that of device 1 ( Fig. 11), except for the light-emitting material of the light-emitting layer 813. The device 6 has a similar structure to that of the device 5, except that the thickness of the hole-transport layer 812 of the device 6 is greater than that of the device 5. Therefore, with regard to the methods for manufacturing components of the device 5 and the device 6 that are the same as the components of the device 1, reference can be made to Example 2. The chemical formula of a material used in this example is shown below. [Table 3] first electrode Hole injection layer Hole transport layer Light-emitting layer Electron transport layer Electron injection layer second electrode 801 811 812 813 814 815 803 Device5 ITSO(70 nm) oYGTBiF(2):ALD-MP001Q(1:0.1, 10nm) oYGTBiF(2)(20 nm) DBfBB1TP(10 nm) cgDBCzPA:1.6BnfAPrn-03(1:0.03, 25 nm) cgDBCzPA(15 nm) NBPhen(10 nm) LiF(1 nm) Al(200 nm) Device6 oYGTBiF(2)(120 nm)

[0336] As shown in Table 3, in the light-emitting layer 813 of the light-emitting devices of this example, cgDBCzPA was used as the host material, 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.

[0337] Furthermore, as shown in Table 3, the thicknesses of oYGTBiF(2) used for the hole transport layer 812 are different between the device 5 and the device 6. <<Betriebseigenschaften der Licht emittierenden Vorrichtungen> >

[0338] The operating characteristics of the light-emitting devices fabricated in this example were measured. Note that the measurements were conducted at room temperature.

[0339] Fig. Figure 18 shows the luminance-power efficiency characteristics of the light-emitting devices. Fig. Figure 19 shows the voltage-luminance characteristics of the light-emitting devices. Fig. Figure 20 shows the voltage-current characteristics of the light-emitting devices. Fig. Figure 21 shows the luminance-external quantum efficiency characteristics of the light-emitting devices.

[0340] Table 4 lists the initial values ​​of main properties of the light-emitting devices at about 1000 cd / m 2 . [Table 4] Voltage (V) Current (mA) Current density (mA / cm 2 ) Chromaticity(x,y) Luminance (cd / m 2 ) Power efficiency (cd / A) Power efficiency (lm / W) external quantum efficiency (%) Energy efficiency (%) Device5 3,0 0,40 10,1 (0,14, 0,14) 1040 10,3 10,8 9,5 8,2 Device6 3,6 0,52 13,1 (0,14, 0,09) 990 7,5 6,6 8,9 6,5

[0341] As in Fig. 18 to Fig. 21 and Table 4, device 5 and device 6 have high emission efficiency. Despite the fact that the thickness of the hole transport layer 812 of device 6 is 100 nm larger than that of device 5, the operating voltage is maintained at 1000 cd / m 2 increased by only 0.6 V. This means that the hole transport property of oYGTBiF(2) is excellent.

[0342] Fig. Figure 22 shows the emission spectra at the time when the light-emitting devices were supplied with a current at a current density of 12.5 mA / cm 2 As in Fig. As shown in Figure 22, the emission spectrum of device 5 has a maximum peak at about 458 nm, which originates from 1,6BnfAPrn-03 contained in the light-emitting layer 813. Similarly, the emission spectrum of device 6 has a maximum peak at about 456 nm. Note that between device 5 and device 6, the optical path length is slightly different, and the emission chromaticity is also different. This is because only the thickness of oYGTBiF(2) was changed, and the transport properties of this material were evaluated.

[0343] Next, reliability tests were performed on the light-emitting devices. Fig. 23A and Fig. 23B shows the results of the reliability tests. In Fig. 23A, the vertical axis represents the normalized luminance (%) assuming that the initial luminance is 100%, and the horizontal axis represents the operating time (h). Fig. 23B, the vertical axis represents the voltage change (ΔV) from the initial voltage (when the operating time is 0) and the horizontal axis represents the operating time (h). In the reliability tests, the light-emitting devices were operated at a current density of 50 mA / cm 2 operated.

[0344] The results of the reliability tests show that both device 5 and device 6 have high reliability.

[0345] In general, when the concentration of the electron acceptor material in the hole injection layer is high and a hole transport material with a deep HOMO level is used, the operating voltage of a light-emitting device is increased in some cases by increasing the thickness of the hole transport layer. As shown in Fig. As shown in Figure 23B, in Device 5 and Device 6, a difference between the voltage after 310 hours of operation and the initial voltage is 0.15 V or less. Therefore, it was found that even if the thickness of the hole-transport layer including the organic compound of one embodiment of the present invention is increased, the operating voltage of the light-emitting device is less likely to increase. [Example 4]

[0346] In this example, light-emitting devices of one embodiment of the present invention are manufactured and evaluated, and the evaluation results are described.

[0347] In this example, a device 7 and a device 8 using oYGTBiF(2) (structural formula (100)) described in Example 1 were fabricated and evaluated as light-emitting devices. The results are described.

[0348] Table 5 shows specific structures of the two light-emitting devices used in this example. Device 7 has a similar structure to that of device 1 ( Fig. 11), except for the materials of the light-emitting layer 813 and the electron-transport layer 814. The device 8 has a similar structure to that of the device 7, except that the thickness of the hole-transport layer 812 of the device 8 is greater than that of the device 7. Therefore, with regard to the methods for manufacturing components of the device 7 and the device 8 that are the same as the components of the device 1, reference can be made to Example 2. The device 7 and the device 8 each have a structure similar to that of the device 1 ( Fig. 11), and therefore, with regard to the methods of manufacturing the device 7 and the device 8, reference can be made to Example 2. The chemical formula of a material used in this example is shown below. [Table 5] first electrode Hole injection layer Hole transport layer Light-emitting layer Electron transport layer Electron injection layer second electrode 801 811 812 813 814 815 803 Device7 ITSO(70 nm) oYGTBiF(2):ALD-MP001Q(1:0.1, 10nm) oYGTBiF(2)(20 nm) DBfBB1TP(10 nm) αN-βNPAnth:1.6BnfAPrn-03(1:0.03, 25 nm) ZADN:Liq(1:1, 25 nm) Liq(1 nm) Al(200 nm) Device8 oYGTBiF(2)(120 nm)

[0349] As shown in Table 5, in the light-emitting layer 813 of each of the light-emitting devices of this example, 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. For the electron-transport layer 814, 2-{4-[9,10-di(naphthalen-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN) and 8-hydroxyquinolinatolithium (abbreviation: Liq) were co-evaporated in a weight ratio of ZADN:Liq = 1:1 to a thickness of 25 nm.

[0350] Furthermore, as shown in Table 5, the thicknesses of oYGTBiF(2) used for the hole transport layer 812 are different between the device 7 and the device 8. <<Betriebseigenschaften der Licht emittierenden Vorrichtungen> >

[0351] The operating characteristics of the light-emitting devices fabricated in this example were measured. Note that the measurements were conducted at room temperature.

[0352] Fig. Figure 24 shows the luminance-power efficiency characteristics of the light-emitting devices. Fig. Figure 25 shows the voltage-luminance characteristics of the light-emitting devices. Fig. Figure 26 shows the voltage-current characteristics of the light-emitting devices. Fig. Figure 27 shows the luminance-external quantum efficiency characteristics of the light-emitting devices.

[0353] Table 6 lists the initial values ​​of main properties of the light-emitting devices at about 1000 cd / m 2 . [Table 6] Voltage (V) Current (mA) Current density (mA / cm 2 ) Chromaticity(x,y) Luminance (cd / m 2 ) Power efficiency (cd / A) Power efficiency (lm / W) external quantum efficiency (%) Energy efficiency (%) Device7 4,0 0,40 9,9 (0,14, 0,14) 990 9,9 7,8 9,1 5,9 Device8 4,6 0,48 12,1 (0,14, 0,09) 880 7,3 5,0 8,6 4,9

[0354] As in Fig. 24 to Fig. 27 and Table 6, device 7 and device 8 have high emission efficiency. Despite the fact that the thickness of the hole transport layer 812 of device 8 is 100 nm larger than that of device 7, the operating voltage is maintained at 1000 cd / m 2 increased by only 0.6 V. This means that the hole transport property of oYGTBiF(2) is excellent.

[0355] Fig. Figure 28 shows the emission spectra at the time when the light-emitting devices were supplied with a current at a current density of 12.5 mA / cm 2 As in Fig. As shown in Figure 28, the emission spectrum of device 7 has a maximum peak at about 458 nm, which originates from 1,6BnfAPrn-03 contained in the light-emitting layer 813. Similarly, the emission spectrum of device 8 has a maximum peak at about 456 nm. Note that between device 7 and device 8, the optical path length is slightly different, and the emission chromaticity is also different. This is because only the thickness of oYGTBiF(2) was changed, and the transport properties of this material were evaluated.

[0356] Next, reliability tests were performed on the light-emitting devices. Fig. 29A and Fig. 29B shows the results of the reliability tests. In Fig. 29A, the vertical axis represents the normalized luminance (%) assuming that the initial luminance is 100%, and the horizontal axis represents the operating time (h). Fig. 29B, the vertical axis represents the voltage change (ΔV) from the initial voltage (when the operating time is 0) and the horizontal axis represents the operating time (h). In the reliability tests, the light-emitting devices were operated at a current density of 50 mA / cm 2 operated.

[0357] The results of the reliability tests show that both device 7 and device 8 have high reliability.

[0358] As in Fig. As shown in Fig. 29B, in Device 7 and Device 8, a difference between the voltage after 380 hours of operation and the initial voltage is 0.20 V or less. Therefore, it was found that even if the thickness of the hole-transport layer including the organic compound of one embodiment of the present invention is increased, the operating voltage of the light-emitting device is less likely to be increased.

[0359] The materials used for the light-emitting layers and the electron-transport layers of the light-emitting devices differ between Example 3 and Example 4. These examples demonstrate that the organic compound of one embodiment of the present invention, when combined with various materials, enables a light-emitting device with high emission efficiency and high reliability. (Reference example)

[0360] The following describe methods for synthesizing 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-fluoren-2-amine (abbreviation: YGTBiF(2)) used for the comparative devices of Example 2. <Synthese von oYGTBi1BP>

[0361] First, 1.4 g (4.2 mmol) of N-(4-biphenylyl)-2-biphenylamine, 1.8 g (4.2 mmol) of 9-(4''-chloro[1,1':4',1''-terphenyl]-4-yl)-9H-carbazole, and 30 mg (84 µmol) of ditert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (registered trademark: cBRIDP) were added to a 200 mL three-necked flask equipped with a reflux tube. The air in the system was replaced with nitrogen. 0.81 g (8.4 mmol) of sodium tert-butoxide and 100 mL of xylene were added to the system. Degassing under reduced pressure and replacement of the air in the system with nitrogen were performed three times. 24 mg (42 µmol) of bis(dibenzylideneacetone)palladium(0) was added to the system, and the mixture was stirred at 150 °C for 11 hours. After stirring, an insoluble substance was removed from the mixture by suction filtration. Water was added to the resulting filtrate, so that an aqueous layer was subjected to extraction with toluene.The resulting organic layer was washed twice with water and then with a saturated saline solution. The organic layer was dried with magnesium sulfate. The resulting mixture was gravity filtered to remove the magnesium sulfate. The resulting filtrate was purified by filtration through alumina and Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the resulting filtrate was concentrated to obtain 2.3 g of a pale yellow solid. The resulting solid was purified by recrystallization (using a mixed solvent of toluene and hexane) to obtain 1.5 g of a pale yellow target solid in a yield of 50%.

[0362] 1.5 g of the resulting solid was purified by a train sublimation process. During sublimation purification, the solid was heated at 345 °C for 16 hours under a pressure of 3.8 Pa at an argon flow rate of 15 ml / min. After sublimation purification, 1.0 g of a pale yellow target solid was obtained with a collection rate of 66%. A synthesis scheme (X-1) is shown below.

[0363] Analysis results by 1 H NMR spectroscopy of the resulting pale yellow solid is shown below. The results indicate that oYGTBi1BP was obtained.

[0364] 1 H-NMR (dichloromethane-d2, 300 MHz): δ = 8.16 (d, J = 8.1 Hz, 2H), 7.90 (dd, J1 = 4.5 Hz, J2 = 1.8 Hz, 2H), 7.77 (dd, J1 = 4.2 Hz, J2 = 2.1 Hz, 2H), 7.70-7.66 (m, 4H), 7.55-7.14 (m, 24H), 6.99 (d, J = 5.7 Hz, 2H), 6.96 (d, J = 5.7 Hz, 2H).

[0365] Next, absorption and emission spectra of oYGTBi1BP were measured in a toluene solution and a solid thin film of oYGTBi1BP. Note that the measurement conditions are similar to those of Example 1, so their description is omitted.

[0366] An absorption peak of oYGTBi1BP in the toluene solution was observed at approximately 365 nm, and an emission peak thereof was observed at approximately 411 nm (excitation wavelength: 346 nm). Absorption peaks of oYGTBi1BP in a solid thin film were observed at approximately 296 nm, 347 nm, and 362 nm, and an emission peak thereof was observed at approximately 426 nm (excitation wavelength: 360 nm).

[0367] Next, the HOMO and LUMO levels of oYGTBi1BP were calculated by CV measurement. The calculation method is similar to that of Example 1, and therefore its description is omitted.

[0368] Furthermore, the CV measurement was repeated 100 times, and the oxidation-reduction wave after the hundredth cycle was compared with the oxidation-reduction wave after the first cycle to investigate the electrical stability of the compound.

[0369] As a result, when measuring the oxidation potential Ea [V] of oYGTBi1BP, the HOMO level was -5.50 eV. On the other hand, when measuring the reduction potential Ec [V], the LUMO level was -2.32 eV. When the oxidation-reduction wave was repeatedly measured in the Ea measurement, the peak intensity of the oxidation-reduction wave after the 100th cycle remained at 85% of that of the oxidation-reduction wave in the first cycle; and in the Ec measurement, the peak intensity of the oxidation-reduction wave after the 100th cycle remained at 94% of that of the oxidation-reduction wave in the first cycle. Thus, the resistance to oxidation and reduction of oYGTBi1BP was found to be very high.

[0370] Differential scanning calorimetry (DSC) was performed on oYGTBi1BP using Pyris1DSC, manufactured by PerkinElmer, Inc. In the differential scanning calorimetry, after raising the temperature from -10°C to 380°C at a temperature increase rate of 40°C / min, the temperature was maintained for 1 minute and then lowered to -10°C at a temperature decrease rate of 100°C / min. This process was repeated twice consecutively. From the DSC measurement result of the second cycle, it was determined that the glass transition point of oYGTBi1BP is 122°C, which indicates that oYGTBi1BP is a substance with very high thermal stability.

[0371] Differential thermal analysis of oYGTBi1BP was performed. The measurement method is similar to that of Example 1, and therefore its description is omitted. The differential thermal analysis revealed that the temperature at which the thermogravimetric weight decreased by 5% of the initial weight (decomposition temperature) was 486 °C, indicating that oYGTBi1BP is a substance with high thermal stability. <Synthese von YGTBiF(2)>

[0372] In a 200 mL three-necked flask equipped with a reflux tube, 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 a 2M potassium carbonate solution, 30 mL of toluene, and 10 mL of ethanol were added. The mixture was degassed under reduced pressure, and the air in the system was replaced with nitrogen. This mixture was heated to 60 °C, and 8.9 mg (40 µmol) of palladium(II) acetate was added. This mixture was refluxed for 10 hours. The resulting mixture was subjected to suction filtration. Water was added to the resulting filtrate, and an aqueous layer was subjected to extraction with toluene. The extracted solution was combined with an organic layer, and the resulting mixture was washed with water and a saturated saline solution and dried with magnesium sulfate.This mixture was gravity filtered, and the resulting filtrate was concentrated to obtain a pale brown solid. The solid was purified by high-performance liquid chromatography (HPLC) to obtain 1.3 g of a light yellow target solid in 43% yield.

[0373] 1.3 g of the resulting solid was purified by a train sublimation process. During sublimation purification, the solid was heated at 350 °C for 15 hours under a pressure of 3.1 Pa at an argon flow rate of 15 ml / min. After sublimation purification, 1.1 g of a pale yellow target solid was obtained with a collection rate of 85%. A synthesis scheme (Y-1) is shown below.

[0374] Analysis results by 1 H NMR spectroscopy of the resulting pale yellow solid is shown below. The results indicate that YGTBiF(2) was obtained.

[0375] 1 H-NMR (dichloromethane-d2, 300 MHz): δ = 8.17 (d, J = 7.8 Hz, 2H), 7.92 (d, J = 8.7 Hz, 2H), 7.75 (dd, J1 = 27.6 Hz, J2 = 9.0 Hz, 4H), 7.70-7.61 (m, 8H), 7.56 (d, J = 9.0 Hz, 2H), 7.52-7.42 (m, 7H), 7.36-7.24 (m, 10H), 7.14 (dd, J1 = 6.0 Hz, J2 = 2.1 Hz, 1H), 1.45 (s, 6H).

[0376] Next, absorption and emission spectra of YGTBiF(2) in a toluene solution and a solid YGTBiF(2) thin film were measured. Note that the measurement conditions are similar to those of Example 1, so their description is omitted.

[0377] An absorption peak of oYGTBiF(2) in the toluene solution was observed at approximately 363 nm, and an emission peak thereof was observed at approximately 425 nm (excitation wavelength: 363 nm). Absorption peaks of YGTBiF(2) in a solid thin film were observed at approximately 294 nm, 350 nm, and 365 nm, and an emission peak thereof was observed at approximately 442 nm (excitation wavelength: 380 nm).

[0378] Next, the HOMO and LUMO levels of YGTBiF(2) were calculated by CV measurement. The calculation method is similar to that of Example 1, and therefore its description is omitted.

[0379] Furthermore, the CV measurement was repeated 100 times, and the oxidation-reduction wave after the hundredth cycle was compared with the oxidation-reduction wave after the first cycle to investigate the electrical stability of the compound.

[0380] As a result, when measuring the oxidation potential Ea [V] of YGTBiF(2), the HOMO level was -5.41 eV. On the other hand, when measuring the reduction potential Ec [V], the LUMO level was -2.34 eV. When the oxidation-reduction wave was repeatedly measured in the Ea measurement, the peak intensity of the oxidation-reduction wave after the 100th cycle was maintained at 90% of that of the oxidation-reduction wave in the first cycle; and in the Ec measurement, the peak intensity of the oxidation-reduction wave after the 100th cycle was maintained at 96% of that of the oxidation-reduction wave in the first cycle. Thus, it was found that the resistance to oxidation and reduction of YGTBiF(2) is very high.

[0381] Differential scanning calorimetry (DSC) was performed on YGTBiF(2) using Pyris1DSC, manufactured by PerkinElmer, Inc. In the differential scanning calorimetry, after raising the temperature from -10°C to 330°C at a temperature increase rate of 40°C / min, the temperature was maintained for 1 minute and then lowered to -10°C at a temperature decrease rate of 100°C / min. This process was repeated twice consecutively. From the second-cycle DSC measurement result, it was determined that the glass transition point of YGTBiF(2) is 145°C, which means that YGTBiF(2) is a substance with very high heat resistance.

[0382] Differential thermal analysis of YGTBiF(2) was performed. The measurement method is similar to that of Example 1, and therefore its description is omitted. The differential thermal analysis revealed that the temperature at which the thermogravimetric weight decreased by 5% of the initial weight (decomposition temperature) was 499 °C, indicating that YGTBiF(2) is a substance with high thermal stability.

[0383] This application is based on Japanese Patent Application Serial No. 2019-129980, filed with the Japan Patent Office on July 12, 2019, the entire contents of which are hereby incorporated by reference.< / ladungserzeugungsschicht> < / elektroneninjektionsschicht> < / elektronentransportschicht>

Claims

[1] Organic compound represented by a formula (G0): where one of R 1 to R 5 represents a formula (A), where the others of R 1 to R 5 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, where R 6 to R 13 , R 23 to R 29 , R 31 to R 39 and R 41 to R 48 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and where R 21 and R 22 each represent a methyl group. [2] Organic compound according to claim 1, where the organic compound is represented by a formula (G1): where R 2 to R 5 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. [3] An organic compound according to claim 1, wherein one of R 35 to R 39 a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group. [4] An organic compound according to claim 1, wherein R 41 to R 48 each independently represents hydrogen, a methyl group, a tert-butyl group or a substituted or unsubstituted phenyl group. [5] A light-emitting device comprising the organic compound according to claim 1. [6] Light-emitting device comprising: a pair of electrodes; and a layer between the pair of electrodes, the layer comprising the organic compound of claim 1. [7] Light-emitting device comprising: a first electrode; a hole transport layer over the first electrode; a light-emitting layer above the hole transport layer; and a second electrode above the light-emitting layer, wherein the light-emitting layer and / or the hole-transport layer comprise / comprises the organic compound according to claim 1. [8] Light-emitting device comprising: the light-emitting device according to claim 5; and a transistor and / or a substrate. [9] Light-emitting module comprising: the light-emitting device according to claim 8; and a connector and / or an integrated circuit. [10] Electronic device comprising: the light-emitting device according to claim 8; and an antenna, a battery, a housing, a camera, a speaker, a microphone and / or a control button. [11] Lighting device comprising: the light-emitting device according to claim 5; and a housing, a cover and / or a support base. [12] Light-receiving device comprising: a pair of electrodes; and a layer between the pair of electrodes, the layer comprising the organic compound of claim 1.

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