Light-emitting element, light-emitting device, electronic appliance, and illumination device

Abstract

To provide a novel organic compound, a novel organic compound with a carrier transport property, a novel organic compound with a hole transport property, an organic compound with a low refractive index, an organic compound with a low refractive index and a carrier transport property, and an organic compound with a low refractive index and a hole transport property.SOLUTION: An organic compound represented by the following General Formula (G1) is provided.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] One aspect of the present invention is an organic compound, a light-emitting element, a display module, a lighting module, The present invention relates to a display device, a light-emitting device, an electronic device, a lighting device, and an electronic device. The present invention is not limited to the above-mentioned technical fields. The present invention relates to a product, a method, or a manufacturing method. Process, Machine, Manufacture, or Composition of Matter Therefore, the present invention relates to a technique according to one embodiment of the present invention disclosed in the present specification. Fields of application include semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, Examples of the memory device, the imaging device, the driving method thereof, or the manufacturing method thereof are given below. It is possible. [Background technology]

[0002] Electroluminescence (EL) using organic compounds The practical application of light-emitting elements (organic electroluminescence (EL) elements) that utilize the luminescence element is progressing. The basic structure of the device is a pair of electrodes sandwiching an organic compound layer (EL layer) containing a light-emitting material. A voltage is applied to this element to inject carriers, and the recombination energy of the carriers is By utilizing this, light can be emitted from the light-emitting material.

[0003] Since such light-emitting elements are self-emitting, when used as display pixels, they are much more efficient than liquid crystal displays. It has the advantages of being highly visible and not requiring a backlight, and is a flat panel display. In addition, displays using such light-emitting elements are thin and lightweight. Another major advantage is that it can be produced in large quantities. Another feature is its extremely fast response time. It is.

[0004] In addition, since the light-emitting layer of these light-emitting devices can be formed continuously in two dimensions, This can be achieved by using point light sources such as incandescent bulbs and LEDs, or This is a feature that is difficult to obtain with linear light sources such as fluorescent lamps, so it can be used as a surface light source for lighting, etc. It is also highly useful.

[0005] Displays and lighting devices using such light-emitting elements are suitable for use in a variety of electronic devices. However, research and development is ongoing to develop light-emitting devices with better characteristics.

[0006] One of the issues that often comes up when talking about organic EL elements is their low light extraction efficiency. In particular, attenuation due to reflection caused by differences in the refractive indices of adjacent layers reduces the efficiency of the device. In order to reduce this effect, a low refractive index material is used inside the EL layer. A structure has been proposed in which a layer having the following structure is formed (see, for example, Non-Patent Document 1).

[0007] A light emitting device having this configuration has a higher light extraction efficiency and, therefore, It is possible to make a light emitting device with high external quantum efficiency. It is easy to form inside the EL layer without adversely affecting other important properties of the light-emitting device. This is because the low refractive index and the high carrier transport properties are suitable for use in light-emitting devices. This is because there is a trade-off between the reliability and the amount of the organic compound. The carrier transport properties and reliability of the unsaturated bonds are largely due to their existence. This is because organic compounds that have a large amount of them tend to have a high refractive index. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent Application Publication No. 11-282181 [Patent Document 2] JP 2009-91304 A [Patent Document 3] U.S. Patent Application Publication No. 2010 / 104969 [Non-Patent Document 1] Jaeho Lee and 12 others, "Synergetic electrode architecture for efficient graphene-based flexible organic light-emitting diodes", Nature COMMUNICATIONS, June 2, 2016, DOI:10.1038 / ncomms11791 Summary of the Invention [Problem to be solved by the invention]

[0009] An object of one embodiment of the present invention is to provide a novel organic compound. In one embodiment, an object of the present invention is to provide a novel organic compound having carrier transport properties. In one embodiment of the present invention, an object of the present invention is to provide a novel organic compound having a hole transport property. An object of one embodiment of the present invention is to provide an organic compound having a small refractive index. In one embodiment of the present invention, an organic compound having a small refractive index and a carrier transport property is provided. Alternatively, in one embodiment of the present invention, a compound having a small refractive index and a hole transport property is provided. The present invention aims to provide an organic compound having the above structure.

[0010] Another object of the present invention is to provide a light-emitting element with high emission efficiency. In another embodiment of the present invention, a light-emitting element, a light-emitting device, an electronic device, a display, or the like that consumes low power is provided. The present invention aims to provide an apparatus and an electronic device, respectively.

[0011] The description of these effects does not preclude the existence of other effects. An embodiment does not necessarily have to have all of these effects. Effects other than these may also be included. The above is self-evident from the description, drawings, claims, etc. Other effects can be extracted from the claims and other descriptions.

[0012] It is sufficient for the present invention to solve any one of the above problems. [Means for solving the problem]

[0013] One embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0014] [ka]

[0015] In the above general formula (G1), Ar 1 ~Ar 4 are each independently a substitution or Unsubstituted phenylene group, substituted or unsubstituted biphenyldiyl group, and substituted or unsubstituted In addition, R 1 ~R 4 are each independently a carbon A saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. In addition, m, n, p and s each independently represent an integer of 0 to 3. Two or more of m, n, p and s each independently represent an integer of 1 to 3.

[0016] Alternatively, in another aspect of the present invention, in the above-mentioned configuration, the Ar 1 and Ar 4 is replaced is an organic compound which is an unsubstituted phenylene group.

[0017] Alternatively, in another aspect of the present invention, in the above-mentioned configuration, the Ar 2 and Ar 3 is replaced is an organic compound that is an unsubstituted biphenyldiyl group.

[0018] Alternatively, in another aspect of the present invention, in the above-mentioned configuration, the Ar 1 ~Ar 4 Replaced or It is an organic compound that is an unsubstituted phenylene group.

[0019] Alternatively, another aspect of the present invention is any one of the above configurations, wherein the m, n, p and s It is an organic compound with a molecular weight of 1.

[0020] Another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[0021] [ka]

[0022] In the above general formula (G2), R 1 ~R 4 At least one of the carbon atoms is 5 to 12. represents a saturated hydrocarbon group or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms; the remainder being independently hydrogen, a saturated hydrocarbon group having 5 to 12 carbon atoms, or a substituted or unsubstituted m, n, p and s each represent a cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. each independently represents an integer of 0 to 3, provided that any two or more of m, n, p, and s are each independently represents an integer from 1 to 3.

[0023] Another embodiment of the present invention is an organic compound represented by the following general formula (G4).

[0024] [ka]

[0025] In the above general formula (G4), R 1 ~R 4 At least one of the carbon atoms is 5 to 12. represents a saturated hydrocarbon group or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms; the remainder being independently hydrogen, a saturated hydrocarbon group having 5 to 12 carbon atoms, or a substituted or unsubstituted m, n, p and s each represent a cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. each independently represents an integer of 0 to 3, provided that any two or more of m, n, p, and s are each independently represents an integer from 1 to 3.

[0026] Another embodiment of the present invention is an organic compound represented by the following general formula (G5).

[0027] [ka]

[0028] In the above general formula (G5), R 1 ~R 4 At least one of the carbon atoms is 5 to 12. represents a saturated hydrocarbon group or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms; the remainder being independently hydrogen, a saturated hydrocarbon group having 5 to 12 carbon atoms, or a substituted or unsubstituted m, n, p and s each represent a cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. each independently represents an integer of 0 to 3, provided that any two or more of m, n, p, and s are each independently represents an integer from 1 to 3.

[0029] Another embodiment of the present invention is an organic compound represented by the following general formula (G3).

[0030] [ka]

[0031] In the above general formula (G3), R 1 ~R 4 each independently represents hydrogen, a group having 5 to 5 carbon atoms 12 saturated hydrocarbon groups or substituted or unsubstituted cyclic saturated hydrocarbon groups having 5 to 12 carbon atoms Represents.

[0032] Another embodiment of the present invention is an organic compound represented by the following general formula (G6).

[0033] [ka]

[0034] In the above general formula (G6), R 1 ~R 4 each independently represents hydrogen, a group having 5 to 5 carbon atoms 12 saturated hydrocarbon groups or substituted or unsubstituted cyclic saturated hydrocarbon groups having 5 to 12 carbon atoms Represents.

[0035] Alternatively, another aspect of the present invention is, in any one of the above configurations, 1 ~R 4 Sik It is an organic compound that is a dihexyl group.

[0036] Another embodiment of the present invention is an organic compound represented by the following structural formula:

[0037] [ka]

[0038] Another embodiment of the present invention is an organic compound represented by the following structural formula:

[0039] [ka]

[0040] Alternatively, another aspect of the present invention is a first electrode, a second electrode, and a first electrode and a second electrode. and an EL layer located between the second electrodes, the EL layer being any of the above-described A light-emitting device that includes an organic compound.

[0041] Alternatively, another aspect of the present invention is a first electrode, a second electrode, and a first electrode and a second electrode. and an EL layer located between the second electrode, the EL layer comprising at least an emissive layer and a hole a hole transport layer, the hole transport layer including any one of the organic compounds described above. be.

[0042] Alternatively, another aspect of the present invention is a first electrode, a second electrode, and a first electrode and a second electrode. and an EL layer located between the second electrode, the EL layer comprising at least an emissive layer and a hole a hole injection layer, the hole injection layer containing any one of the organic compounds described above. be.

[0043] Another aspect of the present invention is a semiconductor device comprising a first electrode, a second electrode, and a semiconductor device including the first electrode and the second electrode. an EL layer located between the second electrode, the EL layer comprising a light-emitting layer, a hole-transporting layer, and The hole transport layer and the hole injection layer are provided with any one of the organic EL devices described above. The light-emitting device includes a compound.

[0044] Another embodiment of the present invention is a light-emitting element including any one of the above light-emitting elements and a transistor or A light emitting device having a substrate and a light emitting element.

[0045] Another embodiment of the present invention is a light-emitting device including the above light-emitting device, a sensor, an operation button, a speaker, or a With a microphone, It is an electronic device having the following:

[0046] Another embodiment of the present invention is a lighting device including the above-described light-emitting device and a housing.

[0047] Another aspect of the present invention is an electronic device including any one of the organic compounds described above. be.

[0048] In this specification, the term "light-emitting device" includes an image display device using a light-emitting element. In addition, a connector, such as an anisotropic conductive film or TCP (Tape Carrier), is attached to the light emitting element. The module has a printed wiring board attached to the end of the TCP. The COG (Chip On Glass) method is used for the module or light emitting element. In some cases, a module on which an IC (integrated circuit) is directly mounted is also included in the light emitting (display) device. Furthermore, lighting fixtures and the like may include a light-emitting device. Effect of the Invention

[0049] According to one embodiment of the present invention, a novel organic compound can be provided. In the present invention, a novel organic compound having carrier transport properties can be provided. In one embodiment of the present invention, a novel organic compound having a hole transporting property can be provided. In one embodiment of the present invention, an organic compound having a small refractive index can be provided. In this manner, an organic compound having a small refractive index and carrier transportability can be provided. Alternatively, in one embodiment of the present invention, an organic compound having a low refractive index and a hole-transporting property is provided. It can be provided.

[0050] In another embodiment of the present invention, a light-emitting element with high emission efficiency can be provided. In another embodiment of the present invention, a light-emitting element, a light-emitting device, an electronic device, or a display device with low power consumption is provided. and an electronic device, respectively.

[0051] The description of these effects does not preclude the existence of other effects. An embodiment does not necessarily have to have all of these effects. Effects other than these may also be included. The above is self-evident from the description, drawings, claims, etc. Other effects can be extracted from the claims and other descriptions. [Brief description of the drawings]

[0052] [Figure 1] Schematic diagram of a light-emitting element. [Diagram 2] FIG. 1 is a conceptual diagram of an active matrix light-emitting device. [Diagram 3] FIG. 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 4] FIG. 1 is a conceptual diagram of an active matrix light-emitting device. [Diagram 5] FIG. 1 is a conceptual diagram of a passive matrix light-emitting device. [Figure 6] FIG. [Figure 7] FIG. [Figure 8]FIG. [Figure 9] FIG. [Figure 10] FIG. [Figure 11] 1 is a diagram illustrating an in-vehicle display device and a lighting device. [Figure 12] FIG. [Figure 13] FIG. [Figure 14] 1H NMR chart of TAPC-02. [Figure 15] Absorption and emission spectra of TAPC-02 in toluene solution. [Figure 16] Absorption and emission spectra of TAPC-02 in a thin film state. [Figure 17] MS spectrum of TAPC-02. [Figure 18] 1H NMR chart of 4,4'-(1,1-cyclohexanediyl)bis{N-(4-cyclohexylphenyl)aminobenzene}. [Figure 19] 1H NMR chart of TAPC-03. [Figure 20] luminance-current density characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 21] Current efficiency-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 22] Luminance-voltage characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 23] Current-voltage characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 24] 4 shows external quantum efficiency-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Diagram 25] 4 shows emission spectra of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 26] Luminance-current density characteristics of light-emitting element 2. [Figure 27] Current efficiency-luminance characteristics of light-emitting element 2. [Figure 28] Luminance-voltage characteristics of light-emitting element 2. [Figure 29] Current-voltage characteristics of light-emitting element 2. [Diagram 30] External quantum efficiency-luminance characteristics of light-emitting element 2. [Diagram 31] Emission spectrum of light-emitting element 2. [Diagram 32] Luminance-current density characteristics of light-emitting element 3. [Diagram 33] Current efficiency-luminance characteristics of light-emitting element 3. [Diagram 34] Luminance-voltage characteristics of light-emitting element 3. [Diagram 35] Current-voltage characteristics of light-emitting element 3. [Diagram 36] External quantum efficiency-luminance characteristics of light-emitting element 3. [Figure 37] Emission spectrum of light-emitting element 3. [Figure 38] Refractive index vs. wavelength for TAPC and TAPC-02. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0053] Hereinafter, the embodiment of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details are not limited thereto without departing from the spirit and scope of the present invention. It will be readily understood by those skilled in the art that various modifications may be made. It should not be construed as being limited to the description of the embodiment modes.

[0054] (Embodiment 1) Among organic compounds having carrier transport properties that can be used in organic EL devices, One of the materials with low molecular weight is 1,1-bis-(4-bis(4-methylphenyl)-amino -phenyl)-cyclohexane (abbreviation: TAPC) is known. By using this in the EL layer, it is possible to obtain a light-emitting element that exhibits high external quantum efficiency. It is expected that the use of TAPC will result in a light-emitting device with good external quantum efficiency. However, TAPC has the problem of low heat resistance and is disadvantageous in terms of reliability. I did.

[0055] One method to obtain a highly heat-resistant and reliable hole transport material is the unsaturated carbonization. It is possible to introduce a hydrogen group, particularly a cyclic unsaturated hydrocarbon group, into the molecule.

[0056] On the other hand, in order to obtain a material with a low refractive index, it is necessary to introduce a substituent with a low molecular refraction into the molecule. The substituent is preferably a saturated hydrocarbon group or a cyclic saturated hydrocarbon group. can.

[0057] In addition, the material used as the carrier transport material in the organic EL element has a backbone with high carrier transport properties. It is preferable that the compound has an aromatic amine skeleton.

[0058] Based on the above findings, the present inventors have realized the following by combining these substituents and skeletons: The compound has a small refractive index and can be suitably used as a hole transport material in an organic EL device. We discovered an organic compound.

[0059] That is, the organic compound of one embodiment of the present invention is an organic compound represented by the following general formula (G1): be.

[0060] [ka]

[0061] In the above general formula (G1), Ar 1 ~Ar 4 are each independently substituted or unsubstituted. Substituted phenylene groups, substituted or unsubstituted biphenyldiyl groups, and substituted or unsubstituted triphenyldiyl group.

[0062] In addition, Ar 1 and Ar 4 is preferably a substituted or unsubstituted phenylene group, and The ylene group is more preferable in view of the synthesis cost.

[0063] Also, Ar 2 and Ar 3 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted The biphenyldiyl group is preferable, and a substituted or unsubstituted phenylene group improves sublimability. In addition, in consideration of the synthesis cost, an unsubstituted phenylene group is even more preferable. It is.

[0064] Ar 1 ~Ar 4 any one of the following is a phenylene group having a substituent, or a biphenyl group having a substituent: In the case of a diyl group or a substituted triphenyldiyl group, the substituent is, for example, Examples of the alkyl group having 1 to 4 carbon atoms include the alkyl group having 1 to 4 carbon atoms. Examples include methyl, ethyl, propyl, isopropyl, n-butyl, and sec-butyl groups. Examples of the alkyl group include a butyl group, an isobutyl group, and a tert-butyl group.

[0065] As mentioned above, Ar 1 ~Ar 4 is preferably an unsubstituted phenylene group, The organic compound can be represented by the following general formula (G2):

[0066] [ka]

[0067] In addition, in the above general formula (G1), as described above, Ar 2 and Ar 3 is an unsubstituted biphenyl. Ar 1 and Ar 4 is preferably an unsubstituted phenylene group. Such an organic compound can be represented by the following general formula (G4).

[0068] [ka]

[0069] In addition, in the above general formula (G1), Ar 2 and Ar 3 is an unsubstituted biphenyldiyl group and Ar 1 and Ar 4 is preferably an unsubstituted phenylene group, but Ar 2 oh And Ar 3 More preferably, is an unsubstituted 4,4'-biphenyldiyl group. Such an organic compound can be represented by the following general formula (G5).

[0070] [ka]

[0071] In the organic compounds represented by the above general formulas (G1), (G2), (G4), and (G5), m, n, p and s each independently represent an integer of 0 to 3; any two or more of the following independently represent an integer of 1 to 3.

[0072] From the viewpoint of ease of synthesis and stability, m, n, p and s are preferably 1. However, among the organic compounds represented by the above general formulas (G4) and (G5), such organic compounds The compounds can be represented by the following general formulas (G3) and (G6).

[0073] [ka]

[0074] [ka]

[0075] In the above general formulae (G1) to (G6), R 1 ~R 4 Each independently represents the number of carbon atoms. A saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. Represents a hydrogen atom.

[0076] Examples of the saturated hydrocarbon group having 5 to 12 carbon atoms include a pentyl group, an isopentyl group, a sec-pentyl group, pentyl, tert-pentyl, neopentyl, hexyl, isohexyl, se c-hexyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group, 2- Methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethyl Butyl group, octyl group, isooctyl group, 2,6-dimethylhexyl group, tert-octyl group 2,6-dimethyloctyl group, 3,3-dimethyloctyl group, 2-methyloctyl group, Examples of the alkyl group include a methylnonyl group, a 3-methylnonyl group, an undecyl group, and a dodecyl group. Examples of the cyclic saturated hydrocarbon group having 5 to 12 carbon atoms include a cyclopentyl group and a cyclohexyl group. , 1-methylcyclopentyl group, 2-methylcyclopentyl group, cycloheptyl group, bis(cyclopentyl) group, Chloro[2,2,1]heptyl, cyclooctyl, bicyclo[2,2,2]octyl , cyclononyl group, bicyclo[3,2,2]nonyl group, bicyclo[3,3,1]nonyl group , cyclodecyl group, cycloundecyl group, bicyclo[5,4,0]undecyl group, cyclo A dodecyl group and the like can be mentioned.

[0077] Also, R 1 ~R 4 any one of the above is a cyclic hydrocarbon group having 5 to 12 carbon atoms and having a substituent. In the case where the substituent is an alkyl group having 1 to 4 carbon atoms, the substituent can be an alkyl group having 1 to 4 carbon atoms. Examples of alkyl groups having 1 to 4 prime numbers include methyl, ethyl, propyl, and isopropyl groups. Examples of the butyl group include an n-butyl group, a sec-butyl group, an isobutyl group, and a tert-butyl group. can.

[0078] In addition, R 1 ~R 4 is a substituent that has the same number of carbon atoms from the viewpoint of atomic or molecular refraction. If so, it is effective to use a substituent having a cyclic structure in order to reduce the refractive index more significantly. and normal and medium-sized ring substituents having six or more members are more preferred. However, large ring substituents are also preferred. Introducing a substituent increases the molecular weight, which may reduce the sublimability. In some cases, this may lead to decomposition, so the cyclohexyl group is It is preferable.

[0079] The organic compound having the above-mentioned structure is an organic compound having a small refractive index and a hole transporting property. For this reason, a light-emitting element using the organic compound has good external quantum efficiency. It is possible to provide a light emitting element.

[0080] Specific examples of organic compounds having the above structure are shown below.

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] Next, a method for synthesizing an organic compound represented by the following general formula (G1), which is one embodiment of the present invention, will be described. An example will be described.

[0091] [ka]

[0092] In the above general formula (G1), Ar 1 ~Ar 4 are each independently substituted or unsubstituted phenylene group, substituted or unsubstituted biphenyldiyl group, and substituted or unsubstituted triphenyl group. R represents either a phenyldiyl group or a phenyldiyl group. 1 ~R 4 are each independently a carbon number of 5 or more Saturated hydrocarbon groups having 5 to 12 carbon atoms or substituted or unsubstituted cyclic saturated hydrocarbons having 5 to 12 carbon atoms In addition, m, n, p and s each independently represent an integer of 1 to 3.

[0093] The organic compound represented by the above general formula (G1) can be prepared by the synthesis of a 1,1- Bis(4-aminophenyl)cyclohexane and organic halides are reacted with gold in the presence of a base. They can be synthesized by coupling with metal catalysts, metals, or metal compounds. Cut.

[0094] [ka]

[0095] In the above synthesis scheme, Ar 1 ~Ar 4 are each independently a substituted or unsubstituted fluoro a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted triphenyl group; Also, R 1 ~R 4 each independently represents a group having 5 to 1 carbon atoms 2 saturated hydrocarbon group or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms In addition, m, n, p and s each independently represent an integer of 1 to 3.

[0096] When the above synthesis scheme is carried out as a Buchwald-Hartwig reaction, X is a halogen or It represents a triflate group. The halogen is preferably iodine, bromine or chlorine. In the reaction, bis(dibenzylideneacetone)palladium(0), allyl palladium dichloride, Palladium complexes or compounds such as palladium mer(II) and tri(tert-butyl) di-tert-butyl (1-methyl-2,2-diphenylcyclopropyl)phosphine ) Using palladium catalysts with ligands such as phosphine and tricyclohexylphosphine The base used is an organic base such as sodium tert-butoxide or potassium carbonate. In addition, when a solvent is used, toluene, xylene, 1,3 , 5-trimethylbenzene, and the like can be used.

[0097] When the above synthesis scheme is carried out as an Ullmann reaction, X represents a halogen. The catalyst is preferably iodine, bromine, or chlorine. Copper or a copper compound is used as the catalyst. It is preferable to use copper(I) iodide or copper(II) acetate. The base may be an inorganic base such as potassium carbonate. The solvent may be 1,3-dimethyl -3,4,5,6-Tetrahydro-2(1H)pyrimidinone (DMPU), N-methyl- 2-pyrrolidone (NMP), toluene, xylene, 1,3,5-trimethylbenzene, etc. However, the above solvents are not limited to these. In the Ullmann reaction, the reaction temperature is The higher the boiling point, the higher the yield and the shorter the time to obtain the desired product. It is preferable to use PU, NMP, and 1,3,5-trimethylbenzene. Since a higher temperature of 150°C or higher is more preferable, it is more preferable to use DMPU. It is decided.

[0098] As described above, the organic compound represented by general formula (G1) can be synthesized.

[0099] (Embodiment 2) FIG. 1 illustrates a light-emitting element according to one embodiment of the present invention. The device has a first electrode 101, a second electrode 102, and an EL layer 103, and the EL layer is The organic compounds shown are used.

[0100] The EL layer 103 has a light-emitting layer 113, a hole-injection layer 111 and / or a hole-transport The light-emitting layer 112 may include a light-emitting material. The light-emitting element emits light from the light-emitting material. The organic compound according to one embodiment of the present invention described in Embodiment 1 may include other materials. Whether it is contained in the light-emitting layer 113 or the hole transport layer 112, the hole injection layer 111 It does not matter whether it is included in one of them or not.

[0101] In addition to these, an electron transport layer 114 and an electron injection layer 115 are also shown in FIG. However, the configuration of the light emitting element is not limited to these.

[0102] The organic compound has a good hole transporting property, and therefore is effectively used for the hole transport layer 112. In addition, the organic compound according to one embodiment of the present invention is a compound obtained by mixing the organic compound with an acceptor substance. The film thus obtained can be used as the hole injection layer 111.

[0103] Furthermore, the organic compound according to one embodiment of the present invention can also be used as a host material. In addition, by co-evaporating an electron transport material, the electron transport material and the hole transport material are It is also possible to form an exciplex by forming an exciplex having an appropriate emission wavelength. This allows for efficient energy transfer to the light-emitting material, resulting in high efficiency and long life. It is possible to provide a light emitting element having the above structure.

[0104] Since the organic compound according to one embodiment of the present invention has a low refractive index, it is possible to form the organic compound in the EL layer. By using this as a part, a light emitting device with good external quantum efficiency can be obtained.

[0105] Next, examples of the detailed structure and materials of the light-emitting element of one embodiment of the present invention will be described. As described above, the optical element has a pair of electrodes, a first electrode 101 and a second electrode 102, and a plurality of layers between the pair of electrodes. The EL layer 103 is formed of the above-mentioned The organic compound disclosed in 1 is included.

[0106] The first electrode 101 is made of a metal, an alloy, or a conductive material having a large work function (specifically, 4.0 eV or more). It is preferable to form the film using a compound such as a carboxylic acid or a mixture thereof. For example, indium tin oxide (ITO), silicon Indium oxide-tin oxide and indium oxide-zinc oxide containing silicon oxide or silicon oxide , indium oxide containing tungsten oxide and zinc oxide (IWZO), etc. These conductive metal oxide films are usually formed by sputtering, but they can also be formed by sol-gel deposition. An example of the method for producing the indium oxide-oxide film is the indium oxide-oxide film. Zinc was sintered using a target containing 1 to 20 wt% zinc oxide in indium oxide. Also, tungsten oxide and zinc oxide are used. Indium oxide (IWZO) contains 0.5% tungsten oxide relative to indium oxide. Sputtering was performed using a target containing 5-5wt% of ZnO and 0.1-1wt% of Zinc Oxide. It can also be formed by the method. In addition, gold (Au), platinum (Pt), nickel (Ni) , Tungsten (W), Chromium (Cr), Molybdenum (Mo), Iron (Fe), Cobalt ( Co), copper (Cu), palladium (Pd), or nitrides of metallic materials (e.g., titanium nitride Graphene can also be used. By using this in the layer 103 that is in contact with the first electrode 101, the electric field can be reduced regardless of the work function. You will be able to choose the pole material.

[0107] The EL layer 103 preferably has a laminated structure, but there is no particular limitation on the laminated structure. There is no definition, and the layer may be a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier block layer, an excitation layer, Various layer structures such as a charge blocking layer and a charge generating layer can be applied. As shown in FIG. 1A, a hole injection layer 111, a hole transport layer 112, and a light emitting layer 113 are In addition, the structure having the electron transport layer 114 and the electron injection layer 115 and the structure shown in FIG. In addition to the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113, the electron transport layer 114 is and a structure having an electron injection layer 115 and a charge generation layer 116 will be described. The materials constituting each layer are specifically shown below.

[0108] The hole injection layer 111 is a layer containing a substance having an acceptor property. The substance may be either an organic compound or an inorganic compound.

[0109] Acceptor substances include compounds with electron-withdrawing groups (halogen groups and cyano groups). The compound can be used, such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethylene. Roquinodimethane (abbreviation: F4-TCNQ), 3,6-difluoro-2,5,7,7,8, 8-Hexacyanoquinodimethane, Chloranil, 2,3,6,7,10,11-Hexacyano No-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1 ,3,4,5,7,8-Hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6 Compounds having electron-withdrawing groups such as -TCNNQ can be used. As an organic compound having such a heteroatom, there is a compound having an electron transport mechanism in a condensed aromatic ring having multiple heteroatoms, such as HAT-CN. Compounds having an electron-withdrawing group bonded thereto are preferred because they are thermally stable. Radialene derivatives that have halogen groups such as fluoro groups or cyano groups are electron acceptors. It is preferred because it is highly tolerable, specifically, α,α',α''-1,2,3-cyclopropanediol. Pantriylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetate nitrile], α,α',α''-1,2,3-cyclopropanetriylidenetris[2, 6-Dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile α,α',α''-1,2,3-cyclopropanetriylidenetris[2,3,4 , 5,6-pentafluorobenzeneacetonitrile]. In addition to the organic compounds mentioned above, other substances that have this property include molybdenum oxide and vanadium oxide. Ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used. In addition, phthalocyanine (abbreviation: H 2 Pc) and copper phthalocyanine (CuPC) Cyanine complex compounds, 4,4'-bis[N-(4-diphenylaminophenyl)- N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3 -methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl Aromatic amine compounds such as diamine (DNTPD) and poly( 3,4-Ethylenedioxythiophene) / Poly(styrenesulfonic acid) (PEDOT / P The hole injection layer 111 can also be formed from a polymer such as SiO2. A substance having the above structure is capable of absorbing electrons from an adjacent hole transport layer (or hole transport material) by applying an electric field. Electrons can be extracted.

[0110] In addition, the hole-injecting layer 111 may be formed by adding an acceptor substance to a substance having a hole-transporting property. A composite material containing an acceptor substance can also be used. By using a composite material with this structure, it is possible to select a material for forming the electrode regardless of its work function. That is, not only a material with a large work function but also a material with a small work function can be used for the first electrode 101. The acceptor materials in question are 7,7,8 ,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TC NQ), Chloranil, 1,3,4,5,7,8-Hexafluorotetracyano-naphthyl Acceptor organic compounds such as dimethyl ether (F6-TCNNQ) and transition metals In addition, the oxides of metals belonging to groups 4 to 8 of the periodic table can be used. The oxides of metals belonging to groups 4 to 8 of the periodic table can also be used. The oxides include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, and molybdenum oxide. tungsten oxide, manganese oxide, rhenium oxide, etc. are preferred due to their high electron-accepting properties. Among them, molybdenum oxide is particularly suitable because it is stable in the air, has low hygroscopicity, and is easy to handle. This is preferable.

[0111] As hole transporting substances used in the composite material, aromatic amine compounds and carbazole derivatives are , aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.), etc. The following organic compounds can be used as hole transporting substances for the composite material: , 10 -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. The following organic compounds can be used as hole transporting substances in the composite material: Raise.

[0112] Aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl) )-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4' -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation Name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl }-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl 1,1-bis-(4-bis(4-methyl- Examples of suitable cyclohexane derivatives include cyclohexane (phenyl)-amino-phenyl)-cyclohexane (abbreviation: TAPC). Specific examples of carbazole derivatives include 3-[N-(9-phenylcarbazole) PCzPC A1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenyla Amino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl -N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazol PCzPCN1, 4,4'-di(N-carbazolyl)biphenyl (abbreviation: C BP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: T CPB), 9-[4-(10-phenylanthracen-9-yl)phenyl]-9H-ca Carbazolyl (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]- 2,3,5,6-tetraphenylbenzene, etc. can be used. For example, 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation Name: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA) , 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation : t-BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9 ,10-Diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene Helical (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene DMNA, 2-tert-butyl-9,10-bis[2-(1-naphthalene 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene , 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9 '-Bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10,10' -Bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bis[(2 ,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl) Perylene, etc. In addition, pentacene, coronene, etc. can also be used. The aromatic hydrocarbon having a vinyl group may have a vinyl skeleton. For example, 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9 ,10-Bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DP Note that the organic compound of one embodiment of the present invention can also be used. In this case, it is preferable to use F6-TCNNQ as the acceptor substance.

[0113] In addition, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenyl PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine N'-phenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( It is also possible to use polymer compounds such as poly(phenyl)benzidine (abbreviation: Poly-TPD). Cut.

[0114] Note that the organic compound of one embodiment of the present invention disclosed in Embodiment 1 is also a material having a hole-transport property. The compound can be suitably used as a hole transporting substance for the composite material. By using the organic compound according to one embodiment of the present invention, a layer having a low refractive index is formed inside the EL layer 103. This makes it possible to improve the external quantum efficiency of the light-emitting device.

[0115] In addition, the composite material may further contain a fluoride of an alkali metal or an alkaline earth metal. or the atomic ratio of fluorine atoms in the layer is 20% or more), thereby This also allows a layer with a low refractive index to be formed inside the EL layer 103. This makes it possible to improve the external quantum efficiency of the light-emitting device.

[0116] By forming the hole injection layer 111, the hole injection property is improved, and the driving voltage is small. In addition, organic compounds having acceptor properties can be easily evaporated. Since it is easy to form a film, it is an easy material to use.

[0117] The hole transport layer 112 is formed by including a material having a hole transport property. The materials are 1×10 -6 cm 2 It is preferable that the hole mobility is equal to or higher than / Vs. The hole transport layer 112 preferably contains an organic compound according to one embodiment of the present invention. By including the organic compound according to the first aspect in the hole transport layer 112, It is possible to form a layer with a low refractive index on the surface of the semiconductor substrate, thereby improving the external quantum efficiency of the light-emitting device. It becomes Noh.

[0118] As the material having the hole transport property, 4,4'-bis[N-(1-naphthyl)-N-phenyl] N,N'-bis(3-methylphenyl)- N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD ), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl 4-phenyl-4'-(9-phenylfluoro)biphenyl (abbreviation: BSPB), 4-phenyl-3'-(phenyl-9-yl)triphenylamine (abbreviation: BPAFLP), 9-Phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4 -Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine PCBA1BP, 4,4'-diphenyl-4''-(9-phenyl-9H- Carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1- naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)-triphenyl PCBANB, 4,4'-di(1-naphthyl)-4''-(9-phenyl -9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 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'-bi Compounds with an aromatic amine skeleton, such as fluorene-2-amine (PCBASF) 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N- Carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl) 3,3'-bis(9-phenyl- 9H-carbazole (abbreviation: PCCP) and other compounds with a carbazole skeleton, ,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene)(abbreviation Name: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-ful oren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4 -[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzyl Compounds with a thiophene skeleton, such as dibenzothiophene (abbreviation: DBTFLP-IV), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation :DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl )phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) Among the above, compounds having an aromatic amine skeleton are preferred. Compounds having a carbazole skeleton have good reliability and high hole transport properties. This is also preferable because it contributes to reducing the driving voltage. The substances listed as the materials having a hole transporting property are also preferably used as the materials for forming the hole transporting layer 112. It can be used appropriately.

[0119] The light-emitting layer 113 is a layer containing a host material and a light-emitting material. The light-emitting material is a fluorescent material. Whether it is a material that emits light, a phosphorescent material, or a material that exhibits thermally activated delayed fluorescence (TADF), In addition, even if the layer is a single layer, different light-emitting materials may be included. The insulating layer may be made of a plurality of layers.

[0120] In the light-emitting layer 113, examples of materials that can be used as the fluorescent material include the following: Examples include the following: Other fluorescent materials can also be used.

[0121] 5,6-Bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine PAP2BPy, 5,6-bis[4'-(10-phenyl-9-anthracene N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl Bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene 9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPr n), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'- Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carba 4'-(10-phenyl-9-anthryl)triphenylamine ( Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl N,9-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol Perylene, 2,5,8,11-tetra-tert-butylamine (abbreviation: PCAPA), -Butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'- (9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA PA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4, 1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (Abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2 -Anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA) , N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'- Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N', N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chryse N-(9, 10-Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3- Amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl) [2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation : 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N '-Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,1 0-Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-t Triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis (1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl] phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N ,9-Triphenylanthracene-9-amine (abbreviation: DPhAPhA), Coumarin 54 5T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bi Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BP T), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl- 4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl 6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidine] 4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5, 11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N' -Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,1 0-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1, 1,7,7-Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij ]Quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitri DCJTI, 2-{2-tert-butyl-6-[2-(1,1,7,7- Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine -9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl} -4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2 ,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetramethyl tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pi {N,N'-diphenyl}propanedinitrile (abbreviation: BisDCJTM), Phenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naphthalene 1,6BnfAPrn-03 In particular, 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6Bn Condensed aromatic diamine compounds, such as pyrene diamine compounds like fAPrn-03 is preferable since it has a high hole trapping property, and is excellent in luminous efficiency and reliability.

[0122] In the light-emitting layer 113, examples of materials that can be used as phosphorescent materials include Some examples include the following:

[0123] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III ) (Abbreviation: [Ir(mpptz-dmp) 3 ]), tris(5-methyl-3,4-diphenyl Nyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mpt z) 3 ]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrtz-3 b) 3 ]) and organometallic iridium complexes with a 4H-triazole skeleton, such as tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-trimethyl Zolato]iridium(III) (abbreviation: [Ir(Mptz1-mp) 3 ]), Triss (1 -Methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium (III) (abbreviation: [Ir(Prptz1-Me)3 ]) Organometallic iridium complexes with fac-tris[(1-2,6-diisopropyl phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi) 3 ]), tris[3-(2,6-dimethylphenyl)-7-methylimide Dazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmp impt-Me) 3 ]), and organometallic iridium complexes having an imidazole skeleton, 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) picolina Fluorocarbon (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)fluorene} Phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir( CF 3 ppy) 2 (pic)]), bis[2-(4',6'-difluorophenyl)pyridine Ginat-N,C 2’ ]Iridium(III) acetylacetonate (abbreviation: FIraca c) Organometallic iridates having phenylpyridine derivatives as ligands having electron-withdrawing groups such as These are compounds that exhibit blue phosphorescence, with wavelengths ranging from 440 nm to It is a compound that has an emission peak at 520 nm.

[0124] In addition, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3 ]), tris(4-t-butyl-6-phenylpyrimidinato)yl Ir(tBuppm) 3 ]), (acetylacetonato)bis (6-Methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp pm) 2 (acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm) 2 (ac ac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpiperidinyl [Ir(nbppm) 2 (acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm) 2 (acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II I) (abbreviation: [Ir(dppm) 2 (acac)] Metal-iridium complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl Rupyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me) 2 (acac) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyridine iridium(III) (abbreviation: [Ir(mppr-iPr) 2 (acac)]) Organometallic iridium complexes with pyrazine skeletons such as tris(2-phenylpyridinium) Nat-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy) 3]), Bis(2- Phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy) 2 (acac)]), bis(benzo[h]quinolinato)iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq) 2 (acac)]), Tris ( [Ir(bzq) 3 ]), Tris (2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq) 3 ]), bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylated Setanato (abbreviation: [Ir(pq) 2 (acac)] In addition to the organometallic iridium complexes, tris(acetylacetonato)(monophenanthroline)tetraacetate Rubium(III) (abbreviation: [Tb(acac) 3 Rare earth metals such as (Phen)] These are mainly compounds that exhibit green phosphorescence, with wavelengths from 500 nm to It has an emission peak at 600 nm. In addition, organometallic iridium with a pyrimidine skeleton The complex is particularly preferred because it has outstanding reliability and luminous efficiency.

[0125] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] Nat]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm)]), vis [4,6-Bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)irid Ir(III) (abbreviation: [Ir(5mdppm) 2(dpm)]), bis[4,6-di( Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (Abbreviation: [Ir(d1npm) 2 Organogold with pyrimidine skeleton such as (dpm)] iridium complexes of the genus acetylacetonato, bis(2,3,5-triphenylpyrazine) Iridium(III) (abbreviation: [Ir(tppr) 2 (acac)]), Bis(2, 3,5-Triphenylpyrazinato)(dipivaloylmethanato)iridium(III)(abbreviation Name:[Ir(tppr) 2 (dpm])]), (acetylacetonato)bis[2,3-bis(acetylacetonato) [Ir(F dpq) 2 and organometallic iridium complexes having a pyrazine skeleton, such as Tris(1-phenylisoquinolinato-N,C 2’ ) Iridium (III) (abbreviation: [I r(piq) 3 ]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium (I II) Acetylacetonate (abbreviation: [Ir(piq) 2 (acac)]) In addition to organometallic iridium complexes with diamine structures, 2,3,7,8,12,13,17,1 8-Octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedione)(monofumab) [Eu(DBM) 3 (Phen)] , Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonate](Monofena Europium(III) (abbreviation: [Eu(TTA) 3 (Phen)] These are compounds that exhibit red phosphorescence and have a 6 It has an emission peak at 00 nm to 700 nm. It is also an organometallic compound with a pyrazine skeleton. The iridium complex can emit red light with good chromaticity.

[0126] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting materials may be selected and used. stomach.

[0127] TADF materials include fullerene and its derivatives, acridine and its derivatives, and eosin. Derivatives of magnesium (Mg), zinc (Zn), cadmium (Cd) and other metals can also be used. (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P d) and the like. The metal-containing porphyrin includes, for example, For example, protoporphyrin-tin fluoride complex (SnF 2 (Pro to IX), mesoporphyrin-tin fluoride complex (SnF 2 (Meso IX) Hematoporphyrin-Tin Fluoride Complex (SnF 2 (Hemato IX), Copropor Phyllin tetramethyl ester-tin fluoride complex (SnF 2 (Copro III-4M e)), octaethylporphyrin-tin fluoride complex (SnF 2 (OEP)), Ethiopia Luphirin-Tin Fluoride Complex (SnF 2 (Etio I)), octaethylporphyrin -Platinum chloride complex (PtCl 2 OEP) etc.

[0128] [ka]

[0129] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenyl)-2-phenylpropanediol having the following structural formula is also available. phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine ( Abbreviation: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT zn), 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl PCCzPT zn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl 3-[4-(5-phenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), -5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1, 2,4-Triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-azide Clydin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[ 4-(9,9-Dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9 π-electron-rich heteroaromatic rings such as '-anthracene]-10'-one (abbreviation: ACRSA) A heterocyclic compound having both a π-electron-deficient heteroaromatic ring and a π-electron-deficient heteroaromatic ring can also be used. The compound has a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, and therefore has an electron transport function. In addition, the π-electron rich heteroaromatic ring and the π-electron deficient heteroaromatic ring are preferably Substances in which heteroaromatic rings are directly bonded exhibit the donor properties of the π-electron rich heteroaromatic ring and the π-electron deficient The acceptor properties of the heteroaromatic rings are both strong, and S 1 Level and T 1 The energy difference between the levels is small Therefore, it is particularly preferable since thermally activated delayed fluorescence can be efficiently obtained. Instead of the toe-shaped heteroaromatic ring, an aromatic ring to which an electron-withdrawing group such as a cyano group is attached may be used. stomach.

[0130] [ka]

[0131] As the host material for the light-emitting layer, various materials such as a material having an electron transport property and a material having a hole transport property can be used. A variety of carrier transport materials can be used.

[0132] The material having a hole transporting property is a material having a hole transporting property contained in the hole transport layer 112. The substances listed as the materials can be suitably used.

[0133] As an example of a material having electron transport properties, bis(10-hydroxybenzo[h]quinoli Natrium(II) (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato )(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8- Quinolinolato)zinc(II)(abbreviation:Znq), bis[2-(2-benzoxazolyl) phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) Metal complexes such as phenolato zinc(II) (abbreviation: ZnBTZ) and 2-(4-biphenyl (aryl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation : PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) phenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butyl) rt-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), 2,2',2''-(1,3,5 -benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TP BI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H -benzimidazole (abbreviation: mDBTBIm-II) and other polyazole skeletons Heterocyclic compounds and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f ,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothio 2-phenyl-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl 2mCzBPDBq, 4,6 -Bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn P2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation Heterocyclic compounds with diazine skeletons such as 3,5 -Bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCz PPy), 1,3,5-tri[3-(3-pyridyl)-phenyl]benzene (abbreviation: Tm Among the above, heterocyclic compounds having a pyridine skeleton such as diphenyl ether (PyPB) are also suitable. Heterocyclic compounds with an azine skeleton and heterocyclic compounds with a pyridine skeleton have good reliability. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton are preferred. The electron transport property is high, and this contributes to reducing the driving voltage.

[0134] When a fluorescent substance is used as a light-emitting material, the host material is a material having an anthracene skeleton. A material having an anthracene skeleton is preferably used as a host material for a fluorescent material. When used in the form of an anthraquinone, it is possible to realize a light-emitting layer having excellent light-emitting efficiency and durability. Since many materials having a Cene skeleton have a deep HOMO level, one embodiment of the present invention is preferably applied to The host material may be a dianthracene skeleton material. Substances with a phenylanthracene skeleton, especially a 9,10-diphenylanthracene skeleton, It is preferable because it is chemically stable. In addition, when the host material has a carbazole skeleton, This is preferable because it enhances the hole injection and transport properties, but the benzene ring is further condensed to the carbazole. In the case of the benzocarbazole skeleton, the HOMO is shallower than that of carbazole by about 0.1 eV. In particular, the host material is preferably dibenzocarbazo When the carbazole skeleton is included, the HOMO is shallower by about 0.1 eV than that of carbazole, and holes can enter. This is preferable because it is easy to form the hole transport layer, has excellent hole transport properties, and has high heat resistance. Further, preferred host materials include those having a 9,10-diphenylanthracene skeleton and Carbazole skeleton (or benzocarbazole skeleton or dibenzocarbazole skeleton) From the viewpoint of the hole injection and transport properties, the carbazole skeleton is Alternatively, a benzofluorene skeleton or a dibenzofluorene skeleton may be used. An example of a substance is 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl] 3-[4-(1-naphthyl)-phenyl]-9H-carbazole (abbreviation: PCzPA), PCPN, 9-[4-(10-phenyl 7-(9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), [4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazide DBZOL (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthoxy) 2mBnfPPA ), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl nyl-4'-yl}anthracene (abbreviation: FLPPA), etc. In particular, CzPA , cgDBCzPA, 2mBnfPPA, and PCzPA are preferred because they show very good properties. This is a good choice.

[0135] The host material may be a mixture of a plurality of substances. When used, a material having an electron transporting property and a material having a hole transporting property may be mixed. It is preferable to mix a material having an electron transporting property with a material having a hole transporting property. In this way, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The ratio of the content of the material having a hole transporting property to the content of the material having an electron transporting property is The ratio of the material having electron transport properties to the material having electron transport properties may be 1:9 to 9:1.

[0136] In addition, these mixed materials may form an exciplex. The exciplex is a light-emitting material. The luminescence of the exciplex is such that it overlaps with the wavelength of the lowest energy absorption band of the By selecting such a combination, energy transfer becomes smooth and light emission can be obtained efficiently. In addition, the use of this configuration is also preferable because the driving voltage can be reduced.

[0137] The electron transport layer 114 is a layer containing a substance having an electron transport property. The above-mentioned substances having an electron transporting property that can be used as the host material are also usable. can be used.

[0138] Between the electron transport layer 114 and the second electrode 102, a lithium fluoride layer is formed as an electron injection layer 115. LiF, CsF, Calcium Fluoride (CaF 2 ) etc. A layer containing an alkali metal or alkaline earth metal or a compound thereof may be provided. The layer 115 is a layer made of a substance having an electron transporting property, and is provided with an alkali metal or alkaline earth metal Alternatively, a material containing such a compound or an electride may be used. For example, a mixed oxide of calcium and aluminum with high electron doping is used. Quality etc.

[0139] Note that the electron-injecting layer 115 is formed using a substance having an electron-transporting property (preferably a substance having a bipyridine skeleton). The above-mentioned alkali metal or alkaline earth metal fluoride is in a microcrystalline state in the organic compound having the above-mentioned structure. It is also possible to use a layer containing a concentration of 50 wt % or more of the refractive index of the layer. Since the layer has a low refractive index, it is possible to provide a light-emitting device with better external quantum efficiency. become.

[0140] In addition, a charge generating layer 116 may be provided instead of the electron injection layer 115 (FIG. 1(B)). When a potential is applied to the charge generating layer 116, holes are generated in the layer in contact with the cathode side of the layer, and electrons are generated in the layer in contact with the anode side of the layer. The charge generating layer 116 is a layer that can inject electrons into the layer adjacent to the charge generating layer. At least a P-type layer 117 is included. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form the P-type layer 1 using the composite material mentioned above as a material that can be used. 17 is a film containing the above-mentioned acceptor material and a hole transport material as a material constituting a composite material. By applying a potential to the P-type layer 117, Electrons are injected into the transport layer 114 and holes are injected into the second electrode 102, which is the cathode, and the light-emitting element operates. In addition, since the organic compound according to one embodiment of the present invention has a low refractive index, P By using this for the mold layer 117, a light emitting device with good external quantum efficiency can be obtained.

[0141] In addition to the P-type layer 117, the charge generating layer 116 also includes an electron relay layer 118 and an electron injection buffer layer 119. Preferably, one or both of layers 119 are provided.

[0142] The electron relay layer 118 contains at least a substance having an electron transport property, and the electron injection buffer layer 1 The function of the junction is to prevent the interaction between the P-type layer 117 and the P-type layer 119 and to transfer electrons smoothly. The LUMO level of the substance having electron transport properties contained in the relay layer 118 is The LUMO level of the acceptor in the electron transport layer 114 and the charge generation layer 116 It is preferable that the LUMO level of the electron-relay layer 11 is between the LUMO level of the material contained in the adjacent layer. Specific energy levels of the LUMO levels of the electron transporting materials used in 8 is set to -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. The electron-transporting material used in the electron relay layer 118 is a phthalocyanine-based It is preferred to use materials or metal complexes having metal-oxygen bonds and aromatic ligands.

[0143] The electron injection buffer layer 119 may include an element selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, lithium carbonate, etc.) (including carbonates such as tium and cesium carbonate), alkaline earth metal compounds (oxides, halogens, etc.) compounds of rare earth metals (including oxides, halides, carbonates) or compounds of rare earth metals (including oxides, halides, carbonates) It is possible to use a material with high electron injection properties such as fluorine.

[0144] The electron injection buffer layer 119 is formed by containing a substance having an electron transporting property and a donor substance. In the case where the donor material is an alkali metal, an alkaline earth metal, or a rare earth metal, and their compounds (alkali metal compounds (oxides such as lithium oxide, halides , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, compounds of rare earth metals (including oxides, halides, carbonates, etc.) In addition to tetrathianaphthalene (TTN), nickelocene, decamethine, An organic compound such as nickelocene can also be used. The electron transport layer 114 is preferably formed of the same material as that of the electron transport layer 114 described above. This can be done.

[0145] The material for forming the second electrode 102 is preferably one having a small work function (specifically, 3.8 eV or less). Bottom) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs). Lithium metals, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or 2 of the Periodic Table of the Elements and alloys containing these elements (MgAg, Rare earth metals such as AlLi), europium (Eu), ytterbium (Yb) and the like However, when the second electrode 102 and the electron transport layer are provided with By providing an electron injection layer, the material can be used in a variety of applications, regardless of the magnitude of the work function. Various conductive materials such as indium oxide-tin oxide containing silicon oxide or silicon oxide are used as the second These conductive materials can be used as the electrode 102. It is possible to form the film using dry methods such as the inkjet method, spin coating method, etc. It may also be formed by a wet method using a sol-gel method, or by using a paste of a metal material. Alternatively, the layer may be formed by a wet method.

[0146] The EL layer 103 can be formed by a variety of methods, including dry and wet methods. For example, vacuum deposition, gravure printing, offset printing, screen printing, etc. A printing method, an ink jet method, a spin coating method or the like may also be used.

[0147] Moreover, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0148] The structure of the layers provided between the first electrode 101 and the second electrode 102 is the same as that described above. However, the light emitting region and the metal used in the electrode or carrier injection layer are not limited to the above. The first electrode 101 and the second electrode 102 are arranged so as to suppress quenching caused by the It is preferable to provide a light-emitting region where holes and electrons recombine at a location away from 02.

[0149] In addition, recombination in the hole transport layer or electron transport layer in contact with the light emitting layer 113, particularly in the light emitting layer 113 The carrier transport layer close to the region suppresses the energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is determined by the luminescent material constituting the luminescent layer or the luminescent material contained in the luminescent layer. It is preferable that the material is made of a substance having a larger band gap than the material. I wish.

[0150] Next, we developed a light-emitting device having a structure in which multiple light-emitting units are stacked (a stacked type device, a tandem type device, etc.). The embodiment of the light-emitting device (also referred to as a "light-emitting device") will be described with reference to FIG. 1(C). A light-emitting element having a plurality of light-emitting units between the light-emitting element and the light-emitting device. 1C). The device is a light-emitting element having a plurality of light-emitting units, and is the light-emitting element shown in FIG. 1(A) or FIG. 1(B). An optical element can be said to be a light-emitting element having one light-emitting unit.

[0151] In FIG. 1C, a first light-emitting unit 511 and a second light-emitting unit 512 are disposed between an anode 501 and a cathode 502. The second light-emitting unit 512 is laminated, and the first light-emitting unit 511 and the second light-emitting unit A charge generating layer 513 is provided between the anode 501 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in FIG. The same as described in the description of the first light-emitting unit 51 can be applied. The first and second light-emitting units 512 may have the same configuration or different configurations.

[0152] When a voltage is applied between the anode 501 and the cathode 502, the charge generating layer 513 emits light from one of the light emitting units. The luminescent unit has a function of injecting electrons into one luminescent unit and injecting holes into the other luminescent unit. In 1(C), when a voltage is applied so that the anode potential is higher than the cathode potential, In this case, the charge generating layer 513 injects electrons into the first light emitting unit 511 and Any material capable of injecting holes into the gate 512 may be used.

[0153] The charge generation layer 513 is formed to have the same structure as the charge generation layer 116 described in FIG. The composite material of an organic compound and a metal oxide has the following advantages: Since the light-emitting unit has excellent characteristics, it can be driven at low voltage and low current. When the anode side surface of the charge generating layer 513 contacts the charge generating layer 513, the charge generating layer 513 becomes the light emitting unit. Since the EL element can also function as a hole injection layer for the light-emitting unit, the light-emitting unit does not need to have a hole injection layer. Both are good.

[0154] In addition, when the charge generating layer 513 is provided with the electron injection buffer layer 119, the electron injection buffer Since the anode layer 119 plays the role of an electron injection layer in the light-emitting unit on the anode side, the light-emitting The unit does not necessarily need to have an electron injection layer.

[0155] Although the light emitting element having two light emitting units has been described in FIG. 1C, a light emitting element having three or more light emitting units may be used. The present invention can be similarly applied to a light-emitting element in which light-emitting units are stacked. In the case of the light-emitting element according to the embodiment of the present invention, a plurality of light-emitting units are disposed between a pair of electrodes, and a charge generating layer 513 is disposed between the pair of electrodes. By separating the layers, it is possible to achieve high brightness light emission while keeping the current density low. It is possible to realize a long-life element. It is also possible to realize a light-emitting device that can be driven at a low voltage and consumes low power. It is possible.

[0156] In addition, by making the emission color of each light-emitting unit different, For example, a light-emitting element having two light-emitting units can be In this case, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. In this way, it is possible to obtain a light-emitting element that emits white light as a whole.

[0157] In addition, the above-mentioned EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and Each layer such as the charge generating layer and the electrodes can be formed by, for example, a deposition method (including a vacuum deposition method), a droplet discharge method (including an inkjet method), etc. It can be formed by using methods such as ink jet printing, coating, and gravure printing. They can be used in a wide range of applications, including low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), and or a polymeric material.

[0158] (Embodiment 3) In this embodiment mode, a light-emitting device using the light-emitting element described in Embodiment 2 will be described.

[0159] In this embodiment, a light-emitting device manufactured using the light-emitting element described in Embodiment 2 will be described. The description will be given with reference to FIG. 2. FIG. 2(A) is a top view showing a light-emitting device, and FIG. 2(B) is a top view showing a light-emitting device. FIG. 1 is a cross-sectional view taken along the lines AB and CD in FIG. The driving circuit section (source line driving circuit) 601 shown by the dotted line controls the pixel section 602 includes a driving circuit section (gate line driving circuit) 603. Also, 604 is a sealing substrate. 605 is a seal material, and the inside surrounded by the seal material 605 is a space 607. .

[0160] The lead wiring 608 is connected to the source line driver circuit 601 and the gate line driver circuit 603. The wiring is for transmitting the signals to be input, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal, etc. from the 609 Although only the FPC is shown here, the FPC has a printed wiring board. The light emitting device in this specification may be a light emitting device. This includes not only the device itself, but also the state in which an FPC or PWB is attached to it. do.

[0161] Next, the cross-sectional structure will be described with reference to FIG. A source line driver circuit 601 and a pixel portion are formed. 6, one pixel in the pixel area 602 is shown.

[0162] The element substrate 610 may be made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl It is made using a plastic substrate made of resin such as fluoride, polyester or acrylic resin. It is sufficient to manufacture it.

[0163] The structure of the transistors used in the pixels and the driver circuits is not particularly limited. The transistor may be a top-type transistor or a staggered type transistor. The transistor may be a gate type transistor or a bottom gate type transistor. The semiconductor material is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and nitride. Gallium, etc., can be used. Alternatively, indium, such as In-Ga-Zn based metal oxides, Alternatively, an oxide semiconductor containing at least one of tungsten, gallium, and zinc may be used.

[0164] The crystallinity of the semiconductor material used in the transistor is not particularly limited. A semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a partially crystalline region If a semiconductor having crystallinity is used, the transistor This is preferable because it can suppress deterioration of the star characteristics.

[0165] Here, in addition to the transistors provided in the pixels and the driver circuits, It is preferable to use an oxide semiconductor for a semiconductor device such as a transistor. In particular, it is preferable to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than silicon, the off-state of the transistor can be improved. This can reduce the current in the negative-going state.

[0166] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn). In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is preferable that the oxide semiconductor contains an oxide represented by the formula (1) of La, Ce or Hf. This is more preferable.

[0167] In particular, the semiconductor layer has a plurality of crystal parts, and the c-axes of the crystal parts are aligned along the surface on which the semiconductor layer is formed, Or, the oxide is oriented perpendicular to the upper surface of the semiconductor layer and has no grain boundary between adjacent crystal portions. It is preferable to use a nitride semiconductor film.

[0168] By using such materials for the semiconductor layer, fluctuations in electrical characteristics are suppressed, leading to high reliability. This makes it possible to realize a high-speed transistor.

[0169] In addition, the transistor having the above-described semiconductor layer can be used as a transistor due to its low off-state current. It is possible to hold the charge stored in the capacitor for a long period of time through such a transistor. By applying a transistor to each pixel, the gradation of the image displayed in each display area can be maintained while driving It is also possible to shut down the circuit. As a result, electronic devices with extremely low power consumption can be realized. It can be realized.

[0170] In order to stabilize the characteristics of the transistor, it is preferable to provide an undercoat film. Inorganic films such as silicon oxide film, silicon nitride film, silicon oxynitride film, and silicon nitride oxide film The insulating film can be formed in a single layer or a multilayer structure. CVD (Chemical Vapor Deposition) method (Plasma CVD method , thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), ALD ( Formed using Atomic Layer Deposition (ALD), coating, printing, etc. It should be noted that the undercoat film does not have to be provided if it is not necessary.

[0171] The FET 623 indicates one of the transistors formed in the driver circuit section 601. The driving circuits are made up of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment, a driver integrated type in which a driver circuit is formed on a substrate is shown. However, this is not necessarily required, and the drive circuit can be formed externally instead of on the substrate. .

[0172] The pixel section 602 includes a switching FET 611, a current control FET 612 and its driver. The pixel is formed by a plurality of pixels including a first electrode 613 electrically connected to the drain. However, the present invention is not limited to this, and a pixel unit may be formed by combining three or more FETs and a capacitance element. good.

[0173] An insulator 614 is formed to cover the end of the first electrode 613. It can be formed by using a photosensitive acrylic resin film of a mold.

[0174] In order to improve the coverage of the EL layer and the like to be formed later, the upper end of the insulator 614 is For example, the material of the insulator 614 is When a positive photosensitive acrylic resin is used, the radius of curvature ( It is preferable that the insulating material 614 has a curved surface having a thickness of 0.2 μm to 3 μm. Either a negative photosensitive resin or a positive photosensitive resin can be used.

[0175] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, the material used for the first electrode 613 functioning as an anode is a material having a work function of It is desirable to use a material with a large capacitance. For example, an ITO film or an indium tin oxide film containing silicon. Indium tin oxide film, indium oxide film containing 2 to 20 wt% zinc oxide, titanium nitride film, In addition to single-layer films such as ROM film, tungsten film, Zn film, and Pt film, titanium nitride film and aluminum film are also available. A titanium nitride film and an aluminum-based film are laminated together. In addition, a three-layer structure with a silicon film can be used. The resistance is low, good ohmic contact can be achieved, and the material can also function as an anode. .

[0176] The EL layer 616 is formed by deposition using a deposition mask, inkjet printing, or spin coating. The EL layer 616 is formed by the structure described in the second embodiment. Other materials constituting the EL layer 616 include low molecular weight compounds, may be a polymer compound (including an oligomer or a dendrimer).

[0177] Furthermore, a material for a second electrode 617 formed on the EL layer 616 and functioning as a cathode As the material, materials with a small work function (Al, Mg, Li, Ca, or alloys or compounds of these) It is preferable to use a material such as MgAg, MgIn, or AlLi. In the case where the light generated in 6 is transmitted through the second electrode 617, the second electrode 617 is The thin metal film and the transparent conductive film (ITO, an indium tin oxide film containing 2 to 20 wt% zinc oxide) It uses lamination of indium, silicon-containing indium tin oxide, zinc oxide (ZnO, etc.) It is better to do so.

[0178] Note that the first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting element. The light-emitting element is the light-emitting element described in Embodiment 2. Note that the pixel portion has a plurality of The light emitting device in this embodiment is formed with a light emitting element. The light-emitting element described above and light-emitting elements having other configurations may be mixed.

[0179] Furthermore, the sealing substrate 604 is bonded to the element substrate 610 with a sealant 605, A light emitting element is disposed in a space 607 surrounded by a child substrate 610, a sealing substrate 604, and a sealant 605. 618. The space 607 is filled with a filler. In addition to being filled with an inert gas (nitrogen, argon, etc.), it can also be filled with a sealing material. A recess is formed in the sealing substrate, and a desiccant is placed there to prevent deterioration due to moisture. This is a preferable configuration.

[0180] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is desirable that these materials are as impermeable to moisture and oxygen as possible. Materials used for the sealing substrate 604 include glass substrates, quartz substrates, and FRP (Fiber Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyester, acrylic resin, or the like can be used.

[0181] Although not shown in FIG. 2, a protective film may be provided on the second electrode. The protective film is an organic resin film. In addition, a protective film may be formed so as to cover the exposed portion of the sealant 605. A protective film may be formed on the front and side surfaces of the pair of substrates, the sealing layer, the insulating layer, etc. A border layer, etc. may be provided over the exposed sides.

[0182] The protective film can be made of a material that is difficult for impurities such as water to permeate. It is possible to effectively suppress the diffusion of impurities such as those mentioned above from the outside to the inside.

[0183] The materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers and the like can be used, for example, aluminum oxide, hafnium oxide, hafnium oxide, etc. Funium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide , titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide , cerium oxide, scandium oxide, erbium oxide, vanadium oxide or indium oxide Materials containing hafnium, aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride, etc. Materials, nitrides containing titanium and aluminum, oxides containing titanium and aluminum , oxides containing aluminum and zinc, sulfides containing manganese and zinc, cerium and and sulfides containing strontium, oxides containing erbium and aluminum, yttrium Materials including, for example, oxides containing lithium and zirconium can be used.

[0184] The protective film should be formed using a film formation method that provides good step coverage. One such technique is atomic layer deposition (ALD). The ALD method can be used to form a protective It is preferable to use the ALD method for films that are dense and free of cracks and pinholes. It is possible to form a protective film having reduced defects or a uniform thickness. Damage to the processed member when forming the protective film can be reduced.

[0185] For example, by forming a protective film using the ALD method, it is possible to fabricate a surface with complex unevenness or a touch panel. It is possible to form a uniform protective film with few defects on the top, sides and back of the panel. .

[0186] In the above manner, a light-emitting device manufactured using the light-emitting element described in Embodiment 2 can be obtained. This can be done.

[0187] The light-emitting device in this embodiment uses the light-emitting element described in Embodiment 2, and therefore has good Specifically, the light-emitting device according to the embodiment 2 can be obtained. Since the element has high light emission efficiency, it is possible to provide a light emitting device with low power consumption.

[0188] In FIG. 3, a light emitting element that emits white light is formed, and a colored layer (color filter) is provided. FIG. 3(A) shows a substrate 1001, a base insulating layer, and a light emitting device. film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, the first An interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driving The driving circuit section 1041, the first electrodes 1024W, 1024R, 1024G, 102 4B, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting element, and a sealing substrate 103 1, sealing material 1032, etc. are shown.

[0189] In addition, in FIG. 3(A), the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on a transparent substrate 1033. 035 may be further provided. A transparent substrate 1 on which a colored layer and a black matrix are provided. The colored layer and the black matrix are fixed to the substrate 1001. The substrate 1035 is covered with an overcoat layer 1036. The light-emitting layer is a layer where light does not pass through the colored layers and goes out to the outside, and the light passes through the colored layers of each color and goes out to the outside. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, green, or blue. This means that images can be expressed using four color pixels.

[0190] In FIG. 3B, the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer An example in which a layer (1034B) is formed between the gate insulating film (1003) and the first interlayer insulating film (1020) In this way, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. is also good.

[0191] In the light emitting device described above, the light is taken in toward the substrate 1001 on which the FET is formed. The light emitting device has a bottom emission structure, but the light is taken in from the sealing substrate 1031 side. The light emitting device may have a structure in which the light is emitted from the top (top emission type). A cross-sectional view of a light-emitting device is shown in FIG. 4. In this case, a substrate 1001 that does not transmit light is used. The bottom electrode is not connected to the anode of the FET and the light-emitting element until the connection electrode is fabricated. The third interlayer insulating film 1037 is then formed on the electrode 1. The third insulating film is formed to cover the 022. This insulating film may also serve as a flattening film. The insulating film 1037 may be formed using the same material as the second interlayer insulating film, or other known materials. This can be done.

[0192] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are anodes here. However, it may be a cathode. Also, in the case of a top emission type light emitting device as shown in FIG. In the case of the above-mentioned arrangement, it is preferable that the first electrode is a reflective electrode. The EL layer 103 has the same structure as that described in the second embodiment, and emits white light. The element structure is designed to obtain such a structure.

[0193] In the top emission structure shown in Figure 4, the colored layers (red colored layer 1034R, green colored layer The sealing is performed by using a sealing substrate 1031 provided with a blue color layer 1034G and a blue color layer 1034B. The sealing substrate 1031 has a black matrix disposed between the pixels. A coloring layer (a red coloring layer 1034R, a green coloring layer 1034G, The blue colored layer (1034B) and the black matrix are covered with an overcoat layer. Note that the sealing substrate 1031 is a substrate having a light-transmitting property. In this example, a full-color display using four colors, red, green, blue, and white, is shown. However, the present invention is not limited to this. A full color display may be achieved using four colors, yellow, green, and blue, or three colors, red, green, and blue.

[0194] In a top emission type light emitting device, a microcavity structure can be suitably applied. In the light-emitting device having a microcavity structure, the first electrode is a reflective electrode and the second electrode is a semi-transparent electrode. The semi-transparent and semi-reflective electrodes are separated by a small amount. It has at least an EL layer, and at least a light-emitting layer which serves as a light-emitting region.

[0195] The reflectance of the reflective electrode for visible light is 40% to 100%, preferably 70% to 100%. %, and its resistivity is 1×10 -2 The film is assumed to be less than Ωcm. The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1×10 -2 It is assumed that the film has a resistance of less than Ωcm.

[0196] The light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transparent and semi-reflective electrode. The light is reflected and resonates.

[0197] The light-emitting element can be formed by changing the thickness of the transparent conductive film, the composite material, the carrier transport material, etc. By changing the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode, Between the reflective electrode and the semi-transmissive / semi-reflective electrode, the light of the resonating wavelength is strengthened and the light of the non-resonating wavelength is strengthened. It is possible to attenuate light of wavelengths.

[0198] The light reflected by the reflective electrode and returned (first reflected light) is semi-transmitted from the light emitting layer. The light that is directly incident on the semi-reflective electrode (first incident light) interferes greatly with the reflective electrode. The optical path length of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the amplified It is preferable to adjust the optical distance to a wavelength that is suitable for the first emission. By matching the phase of the reflected light with that of the first incident light, the light emitted from the light-emitting layer can be amplified. do.

[0199] In the above configuration, even if the EL layer has a structure having a plurality of light-emitting layers, it is possible to use a single light-emitting layer. For example, the above-mentioned tandem light emitting device may be combined with the above-mentioned structure. A single light-emitting element is provided with a plurality of EL layers sandwiching a charge generating layer, and each EL layer is provided with a single Alternatively, the present invention may be applied to a configuration in which a plurality of light-emitting layers are formed.

[0200] The microcavity structure makes it possible to enhance the emission intensity of a specific wavelength in the forward direction. This allows for low power consumption. In the case of a light-emitting device that displays images using a single pixel, the yellow light emission not only improves brightness, but also Since a microcavity structure that matches the wavelength of each color can be applied, it is possible to produce light-emitting devices with excellent characteristics. It can be placed.

[0201] The light-emitting device in this embodiment uses the light-emitting element described in Embodiment 2, and therefore has good Specifically, the light-emitting device according to the embodiment 2 can be obtained. Since the element has high light emission efficiency, it is possible to provide a light emitting device with low power consumption.

[0202] So far, we have explained about active matrix type light emitting devices. From now on, we will discuss passive type light emitting devices. A passive matrix type light emitting device will be described. FIG. 5(A) is a perspective view showing the light-emitting device, and FIG. FIG. 5B is a cross-sectional view taken along the line XY of FIG. 5A. In FIG. 5, on a substrate 951, An EL layer 955 is provided between an electrode 952 and an electrode 956. The ends of the electrode 952 are insulated. The insulating layer 953 is covered with a border layer 953. A partition layer 954 is provided on the insulating layer 953. As the side walls of the partition layer 954 approach the substrate surface, the distance between one side wall and the other side wall decreases. In other words, the cross section of the partition layer 954 in the short side direction is a trapezoid. The bottom side (the side that faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) is higher than the upper side (the side that faces in the same direction as the surface direction of the insulating layer 953 and does not contact the insulating layer 953). In this way, by providing the partition layer 954, the defect of the light-emitting element caused by static electricity or the like can be prevented. In addition, the above-mentioned embodiment can be applied to a passive matrix type light emitting device. 1. A light emitting device having high reliability or a light emitting device having low power consumption, which uses the light emitting element described in 2. The present invention can be an apparatus.

[0203] The light emitting device described above has a large number of minute light emitting elements arranged in a matrix. Since it is possible to control the light emission, it can be suitably used as a display device for displaying images. It is a device.

[0204] This embodiment mode can be freely combined with other embodiment modes.

[0205] (Embodiment 4) In this embodiment, an example in which the light-emitting element described in Embodiment 2 is used as a lighting device will be described with reference to FIG. FIG. 6B is a top view of the lighting device, and FIG. 6A is a schematic diagram of the lighting device in FIG. ef cross-sectional view.

[0206] The lighting device in this embodiment is a first substrate 400 having a light-transmitting property and serving as a support. The first electrode 401 is formed on the substrate 100. The first electrode 401 is the same as the first electrode 10 in the second embodiment. In the case where light is extracted from the first electrode 401 side, the first electrode 401 is a light-transmitting The insulating film is formed from a material having the following properties.

[0207] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0208] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is the same as that described in the second embodiment. The configuration of the EL layer 103 in the above, or the combination of the light-emitting units 511, 512 and the charge generating layer 513 For details of these configurations, please refer to the relevant descriptions.

[0209] A second electrode 404 is formed to cover the EL layer 403. In the case where light is extracted from the first electrode 401 side, the second electrode The first electrode 404 is formed of a highly reflective material. A voltage is supplied by connecting

[0210] As described above, a light-emitting element having a first electrode 401, an EL layer 403, and a second electrode 404 is realized. The lighting device shown in the embodiment has the light-emitting element having high light-emitting efficiency. Therefore, the lighting device in this embodiment can be a lighting device with low power consumption.

[0211] The substrate 400 on which the light emitting element having the above-mentioned structure is formed and the sealing substrate 407 are sealed with a sealant 4. The lighting device is completed by fixing and sealing the components using the sealant 405 and 406. Either one of 5 and 406 may be used. Also, the inner seal material 406 (see FIG. 6(B)) (not shown) can also be mixed with a desiccant to absorb moisture. This leads to improved reliability.

[0212] In addition, the pad 412 and a part of the first electrode 401 are extended outside the sealing materials 405 and 406. By providing a 100mV output, it can be used as an external input terminal. An IC chip 420 incorporating such a function may also be provided.

[0213] As described above, the lighting device described in this embodiment uses the light-emitting element described in embodiment 2 as the EL element. Therefore, a light emitting device with low power consumption can be provided.

[0214] (Embodiment 5) In this embodiment mode, examples of electronic devices each including the light-emitting element described in Embodiment 2 will be described. The light-emitting element described in the second embodiment has high light emission efficiency and low power consumption. As a result, the electronic device described in this embodiment has a light-emitting element with low power consumption. The electronic device may include:

[0215] As an example of an electronic device to which the light-emitting element is applied, a television set (television, (also called revision receivers), computer monitors, digital cameras, digital Video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices) ), portable game machines, personal digital assistants, audio playback devices, pachinko machines and other large game machines, etc. Specific examples of these electronic devices are shown below.

[0216] FIG. 7A shows an example of a television device. The television device includes a housing 710. A display unit 7103 is built into the display unit 1. Also, in this embodiment, a stand 7105 is used to support the display unit 1. The display unit 7103 can display images. The display portion 7103 has the light-emitting elements described in Embodiment 2 arranged in a matrix. It is composed.

[0217] The television device can be operated using an operation switch provided on the housing 7101 or a separate remote control. The remote control device 7110 includes an operation key 7109. This allows you to control the channel and volume, and the image displayed on the display unit 7103 In addition, the remote control operation device 7110 can be operated. A display portion 7107 for displaying information output from the image forming apparatus may be provided.

[0218] The television set is assumed to be equipped with a receiver and a modem. It can receive television broadcasts and can also communicate by wire or wirelessly via a modem. By connecting to a network, communication can be one-way (sender to receiver) or two-way (sender to It is also possible to communicate information between the sender and the recipient, or between the recipients themselves.

[0219] FIG. 7(B1) shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, and a keyboard. keyboard 7204, external connection port 7205, pointing device 7206, etc. In addition, the computer has the light-emitting elements described in the second embodiment arranged in a matrix. The display portion 7203 is used for the computer shown in FIG. The computer shown in FIG. 7B2 may have a keyboard 720. 4. A second display unit 7210 is provided instead of the pointing device 7206. The second display unit 7210 is a touch panel type. Input can be made by operating the input display with a finger or a special pen. In addition, the second display unit 7210 can display not only input images but also other images. The display unit 7203 may also be a touch panel. Two screens are connected by a hinge. This can cause problems such as scratching or breaking the screen when storing or transporting the device. It is also possible to prevent the occurrence of holes.

[0220] FIG. 7C shows a mobile phone as an example of a mobile terminal. The mobile phone has a housing 74. In addition to the display unit 7402 incorporated in the 01, the operation buttons 7403 and the external connection port 7404 7405, a microphone 7406, and the like. The display unit 7402 has the light-emitting elements described in embodiment 2 arranged in a matrix. .

[0221] In the mobile terminal shown in FIG. 7C, information is input by touching the display portion 7402 with a finger or the like. In this case, the user can make a call or write an email. An operation such as pressing a key or the like can be performed by touching the display portion 7402 with a finger or the like.

[0222] The screen of the display unit 7402 has three main modes. The first is a display mode that is mainly used for displaying images. The first mode is a display mode, the second is an input mode for inputting information such as characters, and the third mode is a display mode. This is a display + input mode that combines the display mode and the input mode.

[0223] For example, when making a call or composing an e-mail, the display unit 7402 is used to input characters. The main character input mode is to input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. I wish.

[0224] In addition, the mobile terminal may include a sensor for detecting the inclination, such as a gyro or an acceleration sensor. By providing a device, the orientation of the mobile terminal (vertical or horizontal) can be determined and the screen display of the display portion 7402 can be displayed. The display can be switched automatically.

[0225] The screen mode can be changed by touching the display portion 7402 or by operating the housing 7401. This is done by operating the button 7403. Also, depending on the type of image displayed on the display unit 7402, For example, the image signal to be displayed on the display unit is a moving image. If it is data, the mode is switched to display mode, and if it is text data, the mode is switched to input mode.

[0226] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays If there is no input by touch operation of the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0227] The display portion 7402 can also function as an image sensor. By touching the palm or fingers of the user on the sensor 02 and capturing an image of the palm print or fingerprint, the user can be authenticated. In addition, a backlight that emits near-infrared light to the display unit or a sensing light that emits near-infrared light By using a source, it is also possible to image finger veins, palm veins, etc.

[0228] Note that the configuration shown in this embodiment mode is a combination of the configurations shown in Embodiment Modes 1 to 4. They can be used in combination.

[0229] As described above, the light-emitting device including the light-emitting element described in the second embodiment has a wide range of applications. The light emitting device described in the second embodiment can be applied to electronic devices in various fields. By using the light-emitting element, an electronic device with low power consumption can be obtained.

[0230] FIG. 8(A) is a schematic diagram showing an example of a cleaning robot.

[0231] The cleaning robot 5100 has a display 5101 arranged on the top surface and multiple The camera 5102, the brush 5103, and the operation button 5104 are also shown. However, the underside of the cleaning robot 5100 is provided with tires, a suction port, etc. The robot 5100 also has an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, It is equipped with various sensors such as a sensor, a light sensor, and a gyro sensor. 100 is equipped with wireless communication means.

[0232] The cleaning robot 5100 moves by itself, detects dirt 5120, and sucks it out from the suction port on its bottom. It can suck up dirt.

[0233] In addition, the cleaning robot 5100 analyzes the image captured by the camera 5102 and detects walls, furniture, or It can detect obstacles such as steps. It can also detect wiring and other obstacles by image analysis. If an object that is likely to get tangled in the brush 5103 is detected, the rotation of the brush 5103 can be stopped. can.

[0234] The display 5101 can display the remaining battery level, the amount of dirt sucked up, etc. The route traveled by the cleaning robot 5100 can be displayed on the display 5101. In addition, the display 5101 may be a touch panel, and the operation buttons 5104 may be a display. It may be provided in the ray 5101.

[0235] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. The images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the Cleaning Robot 5100 can check the state of the room even when he / she is away from home. In addition, the display on the display 5101 can be displayed on a mobile electronic device such as a smartphone. You can also check it out at.

[0236] The light-emitting device according to one embodiment of the present invention can be used for the display 5101 .

[0237] The robot 2100 shown in FIG. 8B includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, upper camera 2103, speaker 2104, display 2105, The vehicle is equipped with an internal camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0238] The microphone 2102 has a function of detecting the user's voice and environmental sounds. The speaker 2104 has a function of emitting sound. The user can communicate with the computer using the computer 2102 and the speaker 2104. It is possible.

[0239] The display 2105 has a function of displaying various information. It is possible for the user to display desired information on the display 2105. The display 2105 may be equipped with a touch panel. The information terminal may be a terminal that can be used for charging and discharging the battery. and enables data transfer.

[0240] The upper camera 2103 and the lower camera 2106 are used to capture images of the surroundings of the robot 2100. The obstacle sensor 2107 detects the obstacles of the robot 210 using the moving mechanism 2108. When the robot 21 moves forward, it can sense the presence or absence of obstacles in its path. 00 uses an upper camera 2103, a lower camera 2106, and an obstacle sensor 2107. The light-emitting device according to one embodiment of the present invention can recognize the surrounding environment and move safely. It can be used for the display 2105.

[0241] FIG. 8C is a diagram showing an example of a goggle-type display. For example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, Connection terminal 5006, sensor 5007 (force, displacement, position, speed, acceleration, angular velocity, rotation speed, Distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage, power, radiation (including functions to measure radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), The device has a microphone 5008, a display unit 5002, a support unit 5012, earphones 5013, etc.

[0242] The light-emitting device according to one embodiment of the present invention can be used for the display portion 5001 and the display portion 5002. .

[0243] FIG. 9 shows an example in which the light-emitting element described in the second embodiment is used in a desk lamp, which is a lighting device. The desk lamp shown in FIG. 9 has a housing 2001 and a light source 2002. For this purpose, the lighting device described in the fourth embodiment may be used.

[0244] FIG. 10 shows an example in which the light-emitting element described in the second embodiment is used as an indoor lighting device 3001. The light-emitting element described in the second embodiment has high light-emitting efficiency, and therefore, the power consumption is low. In addition, the light-emitting element described in Embodiment 2 can be made large in area. Therefore, it can be used as a large-area lighting device. The light emitting element is thin, and therefore can be used as a thin lighting device.

[0245] The light-emitting element described in the second embodiment can be mounted on the windshield or dashboard of an automobile. FIG. 11 shows a case where the light-emitting element described in the second embodiment is applied to a windshield or a door of an automobile. The display area 5200 to the display area 5203 are examples of the embodiment. 11 is a display provided using the light-emitting element according to embodiment 2.

[0246] In this embodiment, the display area 5200 and the display area 5201 are provided on the windshield of a car. The light-emitting element according to the embodiment 2 is a display device equipped with the light-emitting element according to the embodiment 2. By making the first electrode and the second electrode from transparent electrodes, the opposite side can be seen through. In this case, a display device in a so-called see-through state can be obtained. If the sensor is installed on the windshield of a car, it can be installed without obstructing the view. In addition, when a transistor for driving is provided, an organic semiconductor material Transistors that have light-transmitting properties, such as organic transistors using It is advisable to use a transistor.

[0247] The display region 5202 is a display having the light-emitting element described in the embodiment mode 2 provided in the pillar portion. The display area 5202 displays an image captured by an imaging means provided on the vehicle body. This can compensate for the visibility obstructed by the pillars. The display area 5203 provided on the board portion allows the view outside the car to be displayed without being blocked by the car body. By projecting images from an imaging device installed in the vehicle, blind spots are filled and safety is improved. By projecting images to complement the invisible parts, it becomes possible to create a more natural and unnatural appearance. This allows for easy safety checks.

[0248] The display area 5203 also displays navigation information, speedometer, tachometer, odometer, fuel gauge, gear By displaying the status, settings of the air conditioner, etc., various information can be provided. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in the display areas 5200 to 5202. The display areas 5200 to 5203 can also be used as lighting devices.

[0249] 12(A) and (B) show a foldable mobile information terminal 5150. The foldable mobile information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 515. 12(A) shows the portable information terminal 5150 in an unfolded state. Fig. 5B) shows the portable information terminal in a folded state. The portable information terminal 5150 has a large display area. Despite having a range of 5152, it folds up compactly and is highly portable.

[0250] The display area 5152 can be folded in half by the bend 5153. 3 is composed of an expandable member and multiple support members, and when folding, the expandable The member is stretched, and the bent portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more. It can be folded.

[0251] The display area 5152 is a touch panel (input / output) equipped with a touch sensor (input device). The light-emitting device according to one embodiment of the present invention can be used in the display region 5152. Cut.

[0252] 13(A) to 13(C) show a foldable portable information terminal 9310. FIG. 13A shows a portable information terminal 9310 in an unfolded state. FIG. 13B shows a portable information terminal 9310 in an unfolded state or A portable information terminal 9310 is shown in a folded state changing from one to the other. FIG. 13C shows the portable information terminal 9310 in a folded state. The foldable design is highly portable and unfolds for a seamless, large viewing area. This provides excellent visibility of the display.

[0253] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). The display panel 9311 may be a display panel (input / output device). The portable information terminal 9310 is in an unfolded state by bending the two housings 9315. The light-emitting device according to one embodiment of the present invention can be reversibly transformed from a folded state to a folded state. It can be used for the display panel 9311. EXAMPLES

[0254] <Synthesis Example 1> In this embodiment, an organic compound, 4,4'-(1,1-cyclohexane, -diyl)bis[N,N-bis(4-cyclohexylbenzene-1-yl)aminobenzene The synthesis method of TAPC-02 (abbreviation: TAPC-02) is explained below. The structure is shown below.

[0255] [ka]

[0256] <Step 1: 4,4'-(1,1-cyclohexanediyl)bis[N,N-bis(4 Synthesis of (cyclohexylbenzene-1-yl)aminobenzene Add 5.3 g (20 mm) of 1,1-bis(4-aminophenyl)cyclohexane to a three-neck flask. ol), 4-cyclohexyl-1-bromobenzene 21.0g (88mmol), sodium 25.4g (264mmol) of tert-butoxide, 400mL of xylene mixture After degassing under reduced pressure, the atmosphere in the flask was replaced with nitrogen. The mixture was heated and stirred until the temperature reached 100° C. Here, allyl palladium chloride dimer(II) (abbreviation: (Allyl PdCl) 2 ) 293mg (0.8mmol), di-tert-butyl(1-methyl-2 ,2-diphenylcyclopropyl)phosphine (trade name: cBRIDP (registered trademark)) 128 mg (3.2 mmol) was added and the mixture was heated to reflux for 6 hours. The temperature of the flask was returned to about 60°C, about 4 mL of water was added, the precipitated solid was filtered off, and the toluene was added. The filtrate was concentrated, and the resulting xylene solution was purified by silica gel column chromatography. The resulting solution was concentrated to obtain a concentrated toluene solution. The precipitate was filtered at about 0°C, and the resulting solid was heated to about 75°C. The product was dried under reduced pressure to obtain 16.5 g of a white solid in 92% yield. The synthesis scheme of compound 1 is shown below.

[0257] [ka]

[0258] The white solid obtained in step 1 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below and in Figure 14. From this, it can be seen that in step 1, 4,4'-(1 ,1-cyclohexane-diyl)bis[N,N-bis(4-cyclohexylbenzene-1 It was found that the compound [(-yl)aminobenzene] could be synthesized.

[0259] 1 H-NMR.δ(CDCl 3 ):7.02-7.11(m,12H),6.91-7. 00(m,12H),2.39-2.47(brm,4H),2.16-2.21(br m,4H),1.78-1.91(brm,16H),1.69-1.76(brm,4 H),1.51-1.57(brm,4H),1.45-1.51(brm,2H),1 .31-1.42(brm,16H),1.17-1.28(brm,4H).

[0260] Next, 6.0 g of the obtained solid was purified by train sublimation. The production was carried out at 355°C under the conditions of a pressure of 3.0 Pa and an argon flow rate of 12.3 mL / min. After purification by sublimation, 4.5 g of a slightly yellowish white solid was obtained with a recovery rate of 74%.

[0261] Next, the absorption and emission spectra of TAPC-02 in toluene and in solid thin films were The solid thin film was prepared on a quartz substrate by vacuum deposition. The samples were analyzed using an ultraviolet-visible spectrophotometer (solution: V-550 manufactured by JASCO Corporation, thin film: Hitachi Ltd. The absorption spectrum of the solution was measured using a quartz crystal. The absorption spectrum of the thin film was calculated by subtracting the absorption spectrum measured by adding only toluene to the filter. The vector is the absorbance (-log 10 [%T / (1 The calculation was made by subtracting the transmittance from the reflectance (%T-%R). Note that %T represents the transmittance and %R represents the reflectance. The spectra were measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.).

[0262] The absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorption and emission intensities. The measurement results of the emission spectrum are shown in FIG.

[0263] Next, the organic compound, TAPC-02, was analyzed by liquid chromatography-mass spectrometry (LC-MS). Chromatography Mass Spectrometry (LC / MS) Mass spectrometry (MS) was performed.

[0264] For LC / MS analysis, LC (liquid chromatography) separation was performed using Waters Acqui Mass spectrometry (MS) was performed using a Waters Xevo UPLC (registered trademark). The LC separation was performed using an Acquity UPL G2 Tof MS. C BEH C4 (2.1×100 mm 1.7 μm), column temperature was 40°C. The mobile phase A was acetonitrile and the mobile phase B was 0.1% formic acid aqueous solution. The pull was adjusted by dissolving TAPC-02 in toluene at a desired concentration and diluting it with acetonitrile. The injection volume was 5.0 μL.

[0265] In LC separation, the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement was Mobile Phase A: The mobile phase B was adjusted to 95:5.

[0266] For MS analysis, electrospray ionization was used. The capillary voltage was set at 3 The voltage was 0.0 kV, the sample cone voltage was 30 V, and detection was performed in positive mode. The component with m / z=899 ionized under the conditions was ionized with argon gas in the collision cell. The energy of the collision with argon ( The collision energy was set to 70 eV. The mass range to be measured was m / z (mass-to-charge ratio). The ratio of the flight time (T The results of detection using OF type MS are shown.

[0267] From the results in Figure 17, TAPC-02 mainly produces product ions around m / z=899. The results shown in Figure 17 indicate that the specific These results are characteristic of TAPC-02, and therefore are useful for identifying the TAPC-02 contained in the mixture. This is important data in the field.

[0268] In addition, the flag m / z=566 observed when measuring at a collision energy of 70 eV The cation ion is the 4,4'-(1, 1-Cyclohexanediyl) [N-bis(4-cyclohexylbenzene-1-yl)a aminobenzene][N'-(4-cyclohexylbenzene-1-yl)aminobenzene] and This is presumed to be one of the characteristics of TAPC-02.

[0269] The refractive index of the synthesized TAPC-02 and that of 1, which is known as an organic compound with a low refractive index. 1-Bis-(4-bis(4-methyl-phenyl)-amino-phenyl)-cyclohexane The refractive indexes of (abbreviated as TAPC) and are shown in Figure 38. Note that the refractive index n is the refractive index of ordinary light. n Ordinary and n Extra-ordinary y and n average, which is the average value of both. In this specification, it is simply referred to as "refractive index". If anisotropy analysis was not performed, n average is used, and n Ordinar You can also read it as y. Note that the value obtained by multiplying the value of n Ordinary by two and the value of n Ext The sum of the ra-ordinary values ​​divided by 3 is n average.

[0270] As shown in FIG. 38, TAPC-02, an organic compound according to one embodiment of the present invention, has a very high refractive index. It was found to be a low-content organic compound.

[0271] Next, the glass transition temperatures (Tg) of TAPC-02 and TAPC were measured by differential scanning calorimetry. The measurements were performed using a differential scanning calorimeter (DSC). The Tg of TAPC-02 was 119°C, and the TAP The Tg of C was 85°C. This shows that TAPC-02 has good heat resistance. I found out. EXAMPLES

[0272] <Synthesis Example 2> In this embodiment, an organic compound, 4,4'-(1,1-cyclohexane, -diyl)bis{N-(4-cyclohexylphenyl)N-[(4´-cyclohexyl) Synthesis of {1,1'-biphenyl-4-yl]aminobenzene} (abbreviation: TAPC-03) The method is explained below. The structure of TAPC-03 is shown below.

[0273] [ka]

[0274] <Step 1: 4,4'-(1,1-cyclohexanediyl)bis{N-(4-cyclo Synthesis of {hexylphenyl)aminobenzene} Add 5.3 g (20 mm) of 1,1-bis(4-aminophenyl)cyclohexane to a three-neck flask. ol), 4-cyclohexyl-1-bromobenzene 10.0g (42mmol), sodium 12.1g (126mmol) of tert-butoxide, 200mL of xylene mixture After degassing under reduced pressure, the atmosphere in the flask was replaced with nitrogen. The mixture was heated and stirred until the temperature reached 100° C. Here, allyl palladium chloride dimer(II) (abbreviation: (Allyl PdCl) 2 ) 150mg (0.4mmol), dicyclohexyl (2',6'-dimeth (xy-{1,1'-biphenyl}-2-yl)phosphine (abbreviation: SPhos) 660m g (1.6 mmol) was added and the mixture was heated to reflux for 6 hours. The temperature was returned to about 60°C, about 2 mL of water was added, and the precipitated solid was filtered and washed with toluene. The filtrate was concentrated, and the resulting xylene solution was purified by silica gel column chromatography. The resulting solution was concentrated to obtain a thick toluene solution. The precipitate was filtered at about 0°C, and the obtained solid was dried under reduced pressure at about 75°C. After drying, the target product, a white solid, was obtained in 9.5 g and a yield of 81%. The system is shown below.

[0275] [ka]

[0276] The white solid obtained in step 1 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 18. In step 1, the organic compound 4,4'-(1,1-cyclohexane-diyl)bis{N -(4-Cyclohexylphenyl)aminobenzene} was successfully synthesized.

[0277] 1 H-NMR.δ(CDCl 3 ):7.02-7.11(m,8H),6.91-6.9 9(m,8H),5.55(br,2H),2.39-2.47(brm,2H),2. 16-2.28(brm,4H),1.76-1.91(brm,8H),1.69-1 .76(brm,2H),1.52-1.60(brm,4H),1.44-1.52( brm,2H),1.31-1.44(brm,8H),1.18-1.28(brm, 4H).

[0278] <Step 2: 4,4'-(1,1-cyclohexanediyl)bis{N-(4-cyclo hexylphenyl)N-[(4'-cyclohexyl)-1,1'-biphenyl-4-yl Synthesis of ]aminobenzene} (abbreviation: TAPC-03)> A three-neck flask was placed in a flask containing 4,4'-(1,1-cyclohexanediyl)bis{N-(4-cyclo 5.8g (10mmol), 4'-cyclohexyl -(1,1'-biphenyl)-4-chlorobenzene 5.4g (20mmol), sodium Add 5.8 g (60 mmol) of tert-butoxide and 70 mL of xylene mixture. After degassing under reduced pressure, the atmosphere in the flask was replaced with nitrogen. The mixture was heated to about 50°C. The mixture was stirred. Here, allyl palladium chloride dimer (II) (abbreviation: (AllylPdCl ) 2 ) 73mg (0.2mmol), di-tert-butyl(1-methyl-2,2-difluoro C-phenylcyclopropylphosphine (abbreviation: cBRIDP) 280 mg (0.8 mmol) ) was added and the mixture was heated to reflux for 8 hours. After that, the temperature of the flask was increased to about 60°C. The mixture was reconstituted, about 2 mL of water was added, and the precipitated solid was filtered off and washed with toluene. The filtrate was concentrated, The obtained xylene solution was purified by silica gel column chromatography. The mixture was concentrated to obtain a concentrated toluene solution. This toluene solution was added dropwise to ethanol to cause reprecipitation. The precipitate was filtered at about 0°C, and the obtained solid was dried under reduced pressure at about 75°C to obtain the target product. The resulting white solid was 5.8 g in a yield of about 100%. The synthesis scheme for step 2 is shown below. As shown in.

[0279] [ka]

[0280] The white solid obtained in step 2 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 19. In step 2, the organic compound 4,4'-(1,1-cyclohexanediyl)bis{N -(4-cyclohexylphenyl)N-[(4'-cyclohexyl)-1,1'-biphenyl] It was found that the compound {4-yl-4-aminobenzene} (abbreviation: TAPC-03) was successfully synthesized. Ta.

[0281] 1 H-NMR.δ(CDCl 3 ):7.46-7.50(m,4H),7.40-7.4 5(m,4H),7.23-7.26(m,4H),6.99-7.17(brm,20 H),2.42-2.59(brm,4H),2.19-2.25(brm,2H),1 .79-1.95(brm,16H),1.70-1.79(brm,4H),1.32 -1.64(brm,24H),1.18-1.32(brm,4H). EXAMPLES

[0282] In this example, a light-emitting element 1 and a comparative light-emitting element 1 according to one embodiment of the present invention will be described. The structural formulae of the organic compounds used in the element 1 and the comparative light-emitting element 1 are shown below.

[0283] [ka]

[0284] (Method of manufacturing light-emitting element 1) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a deposition method. The area was set to 2mm x 2mm.

[0285] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and then dried for 200 After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0286] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0287] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: The 4,4'-bis(9-carbazone) represented by the above structural formula (i) was prepared by a vapor deposition method using resistance heating. 2,2'-dimethyl-biphenyl (abbreviation: dmCBP) and molybdenum oxide (V I) and MoOx were co-evaporated at a weight ratio of 2:0.5 (=dmCBP:MoOx) to a thickness of 10 nm. Thus, the hole injection layer 111 was formed.

[0288] Next, on the hole injection layer 111, 4,4'-(1,1-cyclohexyl) N,N-bis(4-cyclohexylbenzene-1-yl)a After depositing TAPC-02 (aminobenzene) to a thickness of 65 nm, N-(1,1'-biphenyl-4-yl)-9,9-dimethyl represented by structural formula (iii) -N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H- Luoren-2-amine (abbreviation: PCBBiF) was evaporated to a thickness of 5 nm to form a hole transport layer. A transfer layer 112 was formed.

[0289] Next, 2-[3'-(dibenzothiophene-4-yl) Biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq -II), PCBBiF, and (acetylacetonato)bis(phenylacetate) represented by the above structural formula (v). (4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm) 2 (acac)]) in a weight ratio of 0.7:0.3:0.06 (=2mDBTBPDBq -II: PCBBiF: [Ir(dppm) 2 (acac)]) After deposition, the ratio was 0.8:0.2:0.06 (=2mDBTBPDBq-II:PCBBiF :[Ir(dppm) 2 (acac)]) was co-evaporated to form a light-emitting layer 113 having a thickness of 20 nm. was formed.

[0290] Then, 2mDBTBPDBq-II was evaporated onto the light-emitting layer 113 to a thickness of 10 nm. After that, bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (vi) was The electron transport layer 114 was formed by deposition so as to have a film thickness of 5 nm.

[0291] After the electron transport layer 114 is formed, lithium fluoride (LiF) and BPhen are mixed in a volume ratio of 0.75:0.25 (=LiF:BPhen) was co-evaporated to 35 nm and electron injection was performed. Then, aluminum is evaporated to a thickness of 200 nm. The second electrode 102 was then formed, and the light-emitting element 1 of this example was completed.

[0292] (Method of manufacturing comparative light-emitting element 1) The comparative light-emitting element 1 has a hole-transporting layer 112 formed of TAPC-02. , 1,1-bis-(4-bis(4-methyl-phenyl)) represented by the above structural formula (vii) -amino-phenyl)-cyclohexane (abbreviation: TAPC), and the film thickness was set at 70 nm. The other steps were the same as in the fabrication of the light-emitting element 1.

[0293] The device structures of the light-emitting element 1 and the comparative light-emitting element 1 are summarized in the following table.

[0294] [Table 1]

[0295] The light-emitting element 1 and the comparative light-emitting element 1 were placed in a glove box with a nitrogen atmosphere. The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the element). After the encapsulation, UV treatment and heat treatment at 80°C for 1 hour were performed, The characteristics were measured. The glass substrate on which the light-emitting device was fabricated was coated with a No special measures have been taken.

[0296] FIG. 20 shows the luminance vs. current density characteristics of the light-emitting element 1 and the comparative light-emitting element 1, and FIG. The luminance-voltage characteristics are shown in Fig. 21, the current-voltage characteristics are shown in Fig. 22, and the external quantum efficiency-luminance characteristics are shown in Fig. 23. The luminance characteristics are shown in FIG. 24 and the emission spectrum is shown in FIG. 25. m 2 The main characteristics of the luminance and CIE chromaticity are shown in Table 2. A luminance meter (Topcon, BM-5A) was used to measure the emission spectrum. A spectrometer (PMA-11, manufactured by Hamamatsu Photonics) was used. The emission spectra of the comparative light-emitting element 1 overlap very well. It can be seen that the optical path length, which is the product of the film thickness and the refractive index, is almost the same for both. It can be said that the comparison light emitting element 1 and the light emitting element 1 can be compared strictly. The external quantum efficiency in the table below is based on the assumption that the material is Lambertian. The external quantum efficiency was measured by measuring the angular dependence of the emission spectrum and the deviation from the Lambertian distribution. The true value that has been corrected for this error is used.

[0297] [Table 2]

[0298] 20 to 25 and Table 2, it can be seen that the light-emitting element 1 of one embodiment of the present invention has a hole-transport layer having a refractive index A layer made of TAPC-02, an organic compound according to one embodiment of the present invention, having a refractive index lower than that of TAPC. It was found that by having the above structure, a light-emitting element having good luminous efficiency could be obtained. EXAMPLES

[0299] In this example, a light-emitting element 2 according to one embodiment of the present invention will be described. The structural formula of the compound is shown below.

[0300] [ka]

[0301] (Method of manufacturing light-emitting element 2) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a deposition method. The area was set to 2mm x 2mm.

[0302] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and then dried for 200 After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0303] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0304] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: The 4,4'-(1,1-cyclopentasiloxane) represented by the above structural formula (ii) was prepared by a vapor deposition method using resistance heating. N,N-bis(4-cyclohexylbenzene-1-yl)a TAPC-02) and molybdenum(VI) oxide in a weight ratio of 2:0. After co-evaporating 50 nm of TAPC-02 (= TAPC-02: molybdenum oxide) to obtain a thickness of 1.5, the above structure was 4,4'-bis(9-carbazole)-2,2'-dimethyl-biphenyl represented by formula (i) phenyl (abbreviation: dmCBP) and molybdenum (VI) oxide were mixed in a weight ratio of 2:0.5 (=d A hole injection layer 111 was formed by co-evaporation to a thickness of 5 nm so as to obtain a thickness of mCBP:MoOx).

[0305] Next, on the hole injection layer 111, 4-phenyl-4'- (9-Phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) A hole transport layer 112 was formed by vapor deposition of 100 nm.

[0306] Next, 2-[3'-(dibenzothiophene-4-yl) Biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq -II) and N-(1,1'-biphenyl-4-yl) represented by the above structural formula (iii) -9,9-Dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] nyl]-9H-fluoren-2-amine (abbreviation: PCBBiF) and the above structural formula (v) (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium ( III) (abbreviation: [Ir(dppm) 2 (acac)]) in a weight ratio of 0.7:0.3 :0.06(=2mDBTBPDBq-II:PCBBiF:[Ir(dppm) 2 (a After co-evaporation of 20 nm, the ratio was 0.8:0.2:0.06 (=2 mD BTBPDBq-II:PCBBiF:[Ir(dppm) 2 (acac)]) The light-emitting layer 113 was formed to a thickness of 20 nm by co-evaporation as shown in FIG.

[0307] After that, 2mDBTBPDBq-II was deposited to a thickness of 10 nm on the light-emitting layer 113, and then the above structure was Bathophenanthroline (abbreviation: BPhen) represented by formula (vi) was evaporated to a thickness of 5 nm and then electrochemically A transport layer 114 was formed.

[0308] After the electron transport layer 114 is formed, lithium fluoride (LiF) and BPhen are mixed in a volume ratio of 0.75:0.25 (=LiF:BPhen) was co-evaporated to 35 nm and electron injection was performed. Then, aluminum is evaporated to a thickness of 200 nm. The second electrode 102 was formed in the above manner, and the light-emitting element 2 of this example was fabricated.

[0309] The device structure of the light-emitting element 2 is summarized in the table below.

[0310] [Table 3]

[0311] The light emitting element 3 is placed in a glove box with a nitrogen atmosphere so that the light emitting element is not exposed to the atmosphere. The process of sealing the element with a glass substrate (applying a sealant around the element and applying UV light during sealing) After that, the initial characteristics of the light-emitting element 2 were measured. No special measures were taken to improve the extraction efficiency of the glass substrate on which the light-emitting device was fabricated. not present.

[0312] FIG. 26 shows the luminance vs. current density characteristics of the light-emitting element 2, FIG. 27 shows the current efficiency vs. luminance characteristics, and FIG. The voltage characteristics are shown in Fig. 28, the current-voltage characteristics in Fig. 29, the external quantum efficiency-luminance characteristics in Fig. 30, and the emission The optical spectrum is shown in FIG. 2 Major nearby The characteristics are shown in Table 4. The measurement method is the same as in Example 3. The external quantum efficiency shown in the table below is based on the assumption that the material is Lambertian. The quantum efficiency was calculated by measuring the angular dependence of the emission spectrum and calculating the deviation from the Lambertian distribution. The corrected true value is used.

[0313] [Table 4]

[0314] 26 to 31 and Table 4, the light-emitting element 2 of one embodiment of the present invention has high emission efficiency. It was found to be a yellow-orange light-emitting device. In particular, the external quantum efficiency exceeded 35%. The limit of the light extraction efficiency of the device is thought to be about 30%. The external quantum efficiency of the device is extremely high. This is because TAPC-02, which has a low refractive index, is used. This is due to the improvement in light extraction efficiency achieved by using EXAMPLES

[0315] In this example, a light-emitting element 3 according to one embodiment of the present invention will be described. The structural formula of the compound is shown below.

[0316] [ka]

[0317] (Method of Manufacturing Light-Emitting Element 3) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a deposition method. The area was set to 2mm x 2mm.

[0318] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and then dried for 200 After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0319] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0320] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: Calcium fluoride (CaF 2 ) and the above structural formula (vii) Represented by 1,1-bis-(4-bis(4-methyl-phenyl)-amino-phenyl)- Cyclohexane (abbreviation: TAPC) and molybdenum oxide (VI) were mixed in a weight ratio of 3:1:0. .5(=CaF 2 After co-evaporating 45 nm of TAPC and molybdenum oxide, 4,4'-bis(9-carbazole)-2,2'-dimethyl- Biphenyl (abbreviation: dmCBP) and molybdenum (VI) oxide were mixed in a weight ratio of 2:0.5 ( The hole injection layer 111 was formed by co-evaporation to a thickness of 5 nm so as to have a thickness of dmCBP:MoOx.

[0321] Next, on the hole injection layer 111, 4,4'-(1,1-cyclohexyl) N,N-bis(4-cyclohexylbenzene-1-yl)a After evaporating 15 nm of phenylaminobenzene (abbreviation: TAPC-02), the above structural formula (iii) was Represented by N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-( 9-Phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-a The hole transport layer 112 is formed by depositing PCBBiF (abbreviation: PCBBiF) to a thickness of 5 nm. did.

[0322] Next, 2-[3'-(dibenzothiophene-4-yl) Biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq -II), PCBBiF, and bis{2-[6-(4-cyclohexyl)phenyl]-(4-phenyl)-(2-phenyl) ... Ano-2,6-dimethylphenyl)-4-pyrimidinyl-κN 3 ]phenyl-κC}(2 ,4-pentanedionato-κO,O')iridium(III) (abbreviation: [Ir(ppm- dmCP) 2 (acac)]) in a weight ratio of 0.75:0.25:0.05 (=2mD BTBPDBq-II:PCBBiF:[Ir(ppm-dmCP) 2 (acac)]) The light emitting layer 113 was formed to a thickness of 40 nm by co-evaporation.

[0323] After that, 2mDBTBPDBq-II was deposited at 5 nm on the light-emitting layer 113, and then the above structure was 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1, represented by formula (x): 10-phenanthroline (abbreviation: NBPhen) is evaporated to a thickness of 5 nm to form an electron transport layer 114. Successful.

[0324] After the electron transport layer 114 is formed, lithium fluoride (LiF) and BPhen are mixed in a volume ratio of 0.75:0.25 (=LiF:BPhen) was co-evaporated to 35 nm and electron injection was performed. Then, aluminum is evaporated to a thickness of 200 nm. The second electrode 102 was then formed, and the light-emitting element 3 of this example was fabricated.

[0325] The device structure of the light-emitting device 3 is summarized in the table below.

[0326] [Table 5]

[0327] The light emitting element 3 is placed in a glove box with a nitrogen atmosphere so that the light emitting element is not exposed to the atmosphere. The process of sealing the element with a glass substrate (applying a sealant around the element and applying UV light during sealing) After that, the initial characteristics of the light-emitting element 3 were measured. No special measures were taken to improve the extraction efficiency of the glass substrate on which the light-emitting device was fabricated. not present.

[0328] FIG. 32 shows the luminance vs. current density characteristics of the light-emitting element 3, FIG. 33 shows the current efficiency vs. luminance characteristics, and FIG. The voltage characteristics are shown in Fig. 34, the current-voltage characteristics in Fig. 35, the external quantum efficiency-luminance characteristics in Fig. 36, and the emission The optical spectrum is shown in FIG. 2 Major nearby The characteristics are shown in Table 6. The measurement method is the same as in Example 3. The external quantum efficiency shown in the table below is based on the assumption that the material is Lambertian. The quantum efficiency was calculated by measuring the angular dependence of the emission spectrum and calculating the deviation from the Lambertian distribution. The corrected true value is used.

[0329] [Table 6]

[0330] 32 to 37 and Table 4, the external quantum efficiency of the light-emitting element 3 of one embodiment of the present invention is 4 It was found that the light-emitting device exhibited a very high efficiency of 2.5%. It has been found that the use of the compound of one embodiment of the present invention makes it possible to obtain a light-emitting element with high emission efficiency. It was.

[0331] ≪Reference synthesis example≫ In this reference synthesis example, bis{2-[6-(4-cyano-2,6-dimethylphenyl)-4- Pyrimidinyl-κN 3 ]phenyl-κC}(2,4-pentanedionato-κO,O')i Iridium(III) (abbreviation: [Ir(ppm-dmCP) 2 Synthesis of (acac)] In addition, [Ir(ppm-dmCP) 2 The structure of (acac)] is shown below. show.

[0332] [ka]

[0333] <Step 1: 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2- Synthesis of dioxaborolan-2-yl)benzonitrile> 4-Bromo-3,5-dimethylbenzonitrile 10.06g, bis(pinacolato)diborate 18.35 g of tetrahydrofuran, 21.73 g of potassium acetate, and 240 mL of dimethyl sulfoxide were added to the reduced solution. The contents were placed in a three-neck flask equipped with a flow tube, and the inside of the flask was replaced with nitrogen. The contents of the flask were stirred under reduced pressure. After degassing by 1,1'-bis(diphenylphosphino)ferrocene, palladium (II) Dichloride dichloromethane adduct (abbreviation: Pd(dppf)Cl 2 ·CH 2 Cl 2 ) 0.59g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) 0.59 g was added and stirred at 100°C for 32.5 hours. After filtration, extraction was performed with toluene. Then, the mixture was eluted with hexane:ethyl acetate = 10:1. The product was purified by silica gel column chromatography using 1,000 ml of ethyl acetate as a solvent to obtain the desired product (white solid, yield The synthesis scheme of step 1 is shown in the following formula (a-1).

[0334] [ka]

[0335] Step 2: 4-(4-cyano-2,6-dimethylphenyl)-6-phenylpyrimidin Synthesis of Hppm-dmCP Next, 0.74 g of 4-chloro-6-phenylpyrimidine, the ,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane -2-yl)benzonitrile 1.28 g, tripotassium phosphate 3.23 g, toluene 43 m 4.3 mL of water was placed in a three-neck flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The contents of the container were stirred under reduced pressure to degas the contents, and then tris(dibenzylideneacetone)dipalladium ( 0) (Abbreviation: Pd 2(dba) 3 ) 0.094g, Tris(2,6-dimethoxyphenyl ) Phosphine (abbreviation: P(2,6-MeOPh) 3 ) was added and heated at 110°C for 23 After stirring for a certain time, extraction with toluene was performed. Then, hexane:acetic acid was added. Purify by silica gel column chromatography using ethyl acetate 5:1 as a developing solvent to obtain the desired product. The pyrimidine derivative, Hppm-dmCP, was obtained (white solid, yield 0.97 g, 88% yield). The synthetic scheme of step 2 is shown in the following formula (a-2).

[0336] [ka]

[0337] <Step 3: Di-μ-chloro-tetrakis{2-[6-(4-cyano-2,6-dimethyl phenyl)-4-pyrimidinyl-κN 3 ]phenyl-κC}diiridium(III)( Abbreviation: [Ir(ppm-dmCP) 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hppm-d mCP 1.60g, iridium chloride hydrate (IrCl 3 H 2 O) (Furuya Metals) 0 0.81g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. After that, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 3 hours to cause a reaction. After filtration, the residue was suction filtered and washed with methanol to obtain the binuclear complex [Ir(ppm-dmC P) 2 Cl] 2 (orange solid, yield 1.45 g, 67%). The scheme is shown in formula (a-3) below.

[0338] [ka]

[0339] <Step 4: [Ir(ppm-dmCP) 2 Synthesis of (acac)] 20 mL of 2-ethoxyethanol, the binuclear complex obtained in step 3 above, [Ir(ppm-d mCP) 2 Cl] 2 1.44g, acetylacetone (abbreviation: Hacac) 0.41g, Put 0.93 g of sodium carbonate into a recovery flask equipped with a reflux condenser, and heat the flask with argon. The mixture was then irradiated with microwaves (2.45 GHz, 100 W) for 4 hours. The residue was filtered with dichloromethane and the filtrate was concentrated. The mixture was subjected to silica gel column chromatography using a developing solvent of ethyl acetate = 2:1. After purification, the organic gold was obtained by recrystallization in a mixed solvent of dichloromethane and methanol. Group complexes, [Ir(ppm-dmCP) 2 (acac)] was obtained as a yellow-orange powder (yield 0 0.19 g of the resulting yellow-orange powder was subjected to train sublimation. The sublimation purification was carried out under the following conditions: pressure 2.7 Pa, argon gas flow rate 11 mL / The solid was heated at 355°C while flowing at 1000mℓ / min. After purification by sublimation, the desired yellow-orange solid was obtained. The amount was 0.092 g, and the yield was 48%. The synthesis scheme of step 4 is shown in the following formula (a-4). vinegar.

[0340] [ka]

[0341] Nuclear magnetic resonance spectroscopy of the yellow-orange solid obtained in step 4 above ( 1 H-NMR analysis results The results are shown below. From these results, in this synthesis example, [Ir(ppm-dmCP) 2 (a cac)] was obtained.

[0342] 1 H-NMR.δ(CDCl 3 ):1.86(s,6H),2.29(s,12H),5 .36(s,1H),6.44(d,2H),6.86(t,2H),6.91(t,2 H),7.52(s,4H),7.66(d,2H),7.68(s,2H),9.25 (s,2H). [Explanation of symbols]

[0343] 101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 11 2: hole transport layer, 113: light emitting layer, 114: electron transport layer, 115: electron injection layer, 116: Charge generation layer, 117: P-type layer, 118: electron relay layer, 119: electron injection buffer layer, 4 00: substrate, 401: first electrode, 403: EL layer, 404: second electrode, 405: sheet 406: sealing material, 407: sealing substrate, 412: pad, 420: IC chip, 5 01: anode, 502: cathode, 511: first light-emitting unit, 512: second light-emitting unit 513: charge generating layer, 601: driving circuit section (source line driving circuit), 602: pixel section, 6 03: driving circuit section (gate line driving circuit), 604: sealing substrate, 605: sealing material, 607 : Space, 608: Wiring, 609: FPC (Flexible Printed Circuit), 610: Element substrate, 611: switching FET, 612: current control FET, 613: first Electrode, 614: insulator, 616: EL layer, 617: second electrode, 618: light-emitting element, 95 1: substrate, 952: electrode, 953: insulating layer, 954: partition layer, 955: EL layer, 956: Electrode, 1001: substrate, 1002: undercoat insulating film, 1003: gate insulating film, 1006: gate a gate electrode, 1007: a gate electrode, 1008: a gate electrode, 1020: a first interlayer insulating film , 1021: second interlayer insulating film, 1022: electrode, 1024W: first electrode, 1024R : first electrode, 1024G: first electrode, 1024B: first electrode, 1025: partition wall, 1 028: EL layer, 1029: second electrode, 1031: sealing substrate, 1032: sealing material, 1 033: transparent substrate, 1034R: red colored layer, 1034G: green colored layer, 1034 B: blue colored layer, 1035: black matrix, 1037: third interlayer insulating film, 10 40: pixel section, 1041: driving circuit section, 1042: peripheral section, 2001: housing, 2002: Light source, 2100: robot, 2110: computing device, 2101: illuminance sensor, 2102: Microphone, 2103: upper camera, 2104: speaker, 2105: display, 2106: Lower camera, 2107: Obstacle sensor, 2108: Moving mechanism, 3001: Lighting Device, 5000: housing, 5001: display unit, 5002: display unit, 5003: speaker, 5 004: LED lamp, 5005: Operation key, 5006: Connection terminal, 5007: Sensor, 5008: Microphone, 5012: Support, 5013: Earphone, 5100: Cleaning unit Bot, 5101: Display, 5102: Camera, 5103: Brush, 5104: Control button, 5150: mobile information terminal, 5151: housing, 5152: display area, 5153: Bend, 5120: dust, 5200: display area, 5201: display area, 5202: display area area, 5203: display area, 7101: housing, 7103: display unit, 7105: stand, 7 107: display unit, 7109: operation keys, 7110: remote control unit, 7201: main unit, 7 202: Housing, 7203: Display unit, 7204: Keyboard, 7205: External connection port, 7206: pointing device, 7210: second display unit, 7401: housing, 740 2: display unit, 7403: operation buttons, 7404: external connection port, 7405: speaker, 7406: Microphone, 9310: Portable information terminal, 9311: Display panel, 9312: Display area area, 9313: hinge, 9315: housing

Claims

1. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element including a layer containing an organic compound represented by the following general formula (G1) on the first electrode side of the light-emitting layer: 【Chemistry 1】 (However, in the above general formula (G1), Ar １ ~Ar ４ R each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted triphenyldiyl group. １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. m, n, p, and s each independently represent an integer of 0 to 3, provided that any two or more of m, n, p, and s each independently represent an integer of 1 to 3.

2. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element having a layer including an organic compound represented by General Formula (G1) below, in contact with the first electrode. 【Chemistry 2】 (However, in the above general formula (G1), Ar １ ~Ar ４ R each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted triphenyldiyl group. １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. m, n, p, and s each independently represent an integer of 0 to 3, provided that any two or more of m, n, p, and s each independently represent an integer of 1 to 3.

3. In claim 1 or 2, Ar １ and Ar ４ each independently represents a substituted or unsubstituted phenylene group.

4. In any one of claims 1 to 3, Ar ２ and Ar ３ each independently represents a substituted or unsubstituted biphenyldiyl group.

5. In claim 1 or 2, Ar １ ~Ar ４ each independently represents a substituted or unsubstituted phenylene group.

6. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element including a layer containing an organic compound represented by the following general formula (G2) on the first electrode side of the light-emitting layer: 【Chemistry 3】 (However, in the above general formula (G2), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. m, n, p, and s each independently represent an integer of 0 to 3, provided that any two or more of m, n, p, and s each independently represent an integer of 1 to 3.

7. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element having a layer containing an organic compound represented by General Formula (G2) below, in contact with the first electrode. 【Chemistry 4】 (However, in the above general formula (G2), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. m, n, p, and s each independently represent an integer of 0 to 3, provided that any two or more of m, n, p, and s each independently represent an integer of 1 to 3.

8. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element including a layer containing an organic compound represented by the following general formula (G4) on the first electrode side of the light-emitting layer: 【Chemistry 5】 (However, in the above general formula (G4), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. m, n, p, and s each independently represent an integer of 0 to 3, provided that any two or more of m, n, p, and s each independently represent an integer of 1 to 3.

9. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element having a layer containing an organic compound represented by General Formula (G4) below, in contact with the first electrode. 【Chemistry 6】 (However, in the above general formula (G4), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. m, n, p, and s each independently represent an integer of 0 to 3, provided that any two or more of m, n, p, and s each independently represent an integer of 1 to 3.

10. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element including a layer containing an organic compound represented by General Formula (G5) below, on the first electrode side of the light-emitting layer: 【Chemistry 7】 (However, in the above general formula (G5), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. m, n, p, and s each independently represent an integer of 0 to 3, provided that any two or more of m, n, p, and s each independently represent an integer of 1 to 3.

11. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element having a layer including an organic compound represented by General Formula (G5) below, in contact with the first electrode. 【Chemistry 8】 (However, in the above general formula (G5), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. m, n, p, and s each independently represent an integer of 0 to 3, provided that any two or more of m, n, p, and s each independently represent an integer of 1 to 3.

12. In any one of claims 1 to 11, m, n, p and s each independently represent an integer of 1 to 3.

13. In any one of claims 1 to 12, A light-emitting element, wherein m, n, p and s are 1.

14. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element including a layer containing an organic compound represented by the following general formula (G3) on the first electrode side of the light-emitting layer: 【Chemistry 9】 (However, in the above general formula (G3), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms.

15. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element having a layer containing an organic compound represented by General Formula (G3) below, in contact with the first electrode. 【Chemistry 10】 (However, in the above general formula (G3), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms.

16. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element including a layer containing an organic compound represented by the following general formula (G6) on the first electrode side of the light-emitting layer: 【Chemistry 11】 (However, in the above general formula (G6), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms.

17. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element having a layer including an organic compound represented by General Formula (G6) below, in contact with the first electrode. 【Chemistry 12】 (However, in the above general formula (G6), R １ ~R ４ each independently represents a saturated hydrocarbon group having 5 to 12 carbon atoms or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms.

18. In any one of claims 1 to 17, R １ ~R ４ each independently is a cyclohexyl group.

19. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element comprising a layer containing an organic compound represented by the following structural formula, the layer being located closer to the first electrode than the light-emitting layer: 【Chemistry 13】

20. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element having a layer in contact with the first electrode and containing an organic compound represented by the following structural formula: 【Chemistry 14】

21. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element comprising a layer containing an organic compound represented by the following structural formula, the layer being located closer to the first electrode than the light-emitting layer: 【Chemistry 15】

22. a light-emitting layer between a first electrode and a second electrode having a light-transmitting property; A light-emitting element having a layer in contact with the first electrode and containing an organic compound represented by the following structural formula: 【Chemistry 16】

23. A light emitting device comprising: the light emitting element according to claim 1 ; and at least one of a transistor and a substrate.

24. A light emitting device according to claim 23, and at least one of a sensor, an operation button, a speaker, and a microphone; An electronic device having the

25. A lighting device comprising the light-emitting device according to claim 23 and a housing.

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