Light-emitting element, light-emitting device, electronic device, and lighting 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 relates to an organic compound, a light-emitting element, a display module, a lighting module, a display device, a light-emitting device, an electronic device, a lighting device, and an electronic device. Note that one aspect of the present invention is not limited to the above technical field. The technical field of one aspect of the invention disclosed in this specification and the like relates to an article, a method, or a manufacturing method. Alternatively, one aspect of the present invention is a process, a machine, a manufacture, or a composition of matter related thereto. Therefore, more specifically, the technical field of one aspect of the present invention disclosed in this specification includes, as an example, a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, a lighting device, a power storage device, a storage device, an imaging device, their driving methods, or their manufacturing methods.

Background Art

[0002] The practical application of a light-emitting element (organic EL element) that utilizes electroluminescence (EL) using an organic compound is progressing. The basic configuration of these light-emitting elements is one in which an organic compound layer (EL layer) containing a light-emitting material is sandwiched between a pair of electrodes. When a voltage is applied to this element to inject carriers and utilize the recombination energy of the carriers, light emission from the light-emitting material can be obtained.

[0003] Since such a light-emitting element is self-emitting, when used as a pixel of a display, it has advantages such as higher visibility and no need for a backlight compared to liquid crystals, and is suitable as a flat panel display element. In addition, a display using such a light-emitting element is thin and light ​​ The ability to produce them in large quantities is a major advantage. Furthermore, their extremely fast response speed is another notable feature. That is the case.

[0004] Furthermore, since these light-emitting elements can form a light-emitting layer continuously in two dimensions, Light can be obtained in a specific shape. This is a point light source, such as an incandescent light bulb or an LED, or Because this characteristic is difficult to obtain with linear light sources such as fluorescent lamps, it can be used as a surface light source for lighting and other applications. It also has high utility value.

[0005] Displays and lighting devices using light-emitting elements in this manner are suitable for application in various electronic devices. However, research and development are underway to find light-emitting elements with even better characteristics.

[0006] One of the issues that often arises when discussing organic EL elements is their low light extraction efficiency. In particular, attenuation due to reflection caused by differences in refractive index between adjacent layers reduces the efficiency of the element. This is a major contributing factor. To mitigate this effect, a low refractive index material is used inside the EL layer. A configuration has been proposed that forms a layer (see, for example, Non-Patent Document 1).

[0007] A light-emitting element with this configuration has a higher light extraction efficiency than a light-emitting element with a conventional configuration, and therefore While it is possible to create a light-emitting element with high external quantum efficiency, such a low refractive index layer, It is easy to form it inside the EL layer without adversely affecting other important characteristics of the light-emitting element. That is not the case. Because a low refractive index and high carrier transport properties or light-emitting elements are used This is because reliability in such cases is in a trade-off relationship. This problem applies to organic compounds. The carrier transportability and reliability largely stem from the presence of unsaturated bonds, and the unsaturated bonds This is because many organic compounds have a high refractive index. [Prior art documents] [Patent Documents]

[0008] [Patent Document 1] Japanese Patent Application Publication No. 11-282181 [Patent Document 2] Japanese Patent Publication No. 2009-91304 [Patent Document 3] U.S. Patent Application Publication No. 2010 / 104969 [Non-Patent Document 1] Jaeho Lee, et al., "Synergetic electrode architecture for efficient graphene-based flexible organic light-emitting diodes," Nature Communications, June 2, 2016, DOI: 10.1038 / ncomms11791 [Overview of the project] [Problems that the invention aims to solve]

[0009] One aspect of the present invention aims to provide a novel organic compound. In this embodiment, the objective is to provide a novel organic compound having carrier transport properties. In one aspect of the present invention, the objective is to provide a novel organic compound having hole transport properties. In one aspect of the present invention, the objective is to provide an organic compound with a low refractive index. In one aspect of the present invention, an organic compound having a low refractive index and carrier transport properties is provided. The objective is to achieve the following: Alternatively, in one aspect of the present invention, the refractive index is small and the hole transport properties are The objective is to provide organic compounds that possess these properties.

[0010] Alternatively, in another aspect of the present invention, the objective is to provide a light-emitting element with high luminescence efficiency. Alternatively, in one aspect of the present invention, a light-emitting element, a light-emitting device, an electronic device, a display with low power consumption. The purpose is to provide equipment and electronic devices, respectively.

[0011] Furthermore, the description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. Furthermore, other effects are... This will become clear from the description in the specification, drawings, claims, etc., and the specification, drawings Furthermore, it is possible to extract other effects from the descriptions in the claims and other documents.

[0012] The present invention only needs to solve one of the above-mentioned problems. [Means for solving the problem]

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

[0014] [ka]

[0015] However, in the above general formula (G1), Ar 1 ~Ar 4 These can be substituted or Unsubstituted phenylene group, substituted or unsubstituted biphenyldiyl group and substituted or unsubstituted It represents any of the triphenyldiyl groups. Also, R 1 ~R 4 Each is independently of carbon Saturated hydrocarbon groups having 5 to 12 carbon atoms or substituted or unsubstituted cyclic saturated carbons having 5 to 12 carbon atoms It represents a hydrogenated group. Also, m, n, p, and s each independently represent an integer from 0 to 3, Any two or more of m, n, p, and s each independently represent an integer from 1 to 3.

[0016] Alternatively, another aspect of the present invention is that in the above configuration, the Ar 1 and Ar 4 is a substituted or unsubstituted phenylene group organic compound.

[0017] Alternatively, another aspect of the present invention is that in the above configuration, the Ar 2 and Ar 3 is a substituted or unsubstituted biphenyldiyl group organic compound.

[0018] Alternatively, another aspect of the present invention is that in the above configuration, the Ar 1 to Ar 4 is a substituted or unsubstituted phenylene group organic compound. <_{0000220}>

[0019] Alternatively, another aspect of the present invention is that in any of the above configurations, the m, n, p, and s is 1 organic compound.

[0020] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G2).

[0021]

Chemical formula

[0022] However, in the above general formula (G2), R 1 to R 4 at least one 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 and the rest each independently represent hydrogen, 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. Also, m, n, p, and s are each respectively. Each represents an integer between 0 and 3 independently, but any two or more of m, n, p, and s are independent. It represents an integer between 1 and 3.

[0023] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G4).

[0024] [ka]

[0025] However, in the above general formula (G4), R 1 ~R 4 at least one of them has 5 to 12 carbon atoms. This represents a saturated hydrocarbon group or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. The remaining atoms are, independently, hydrogen, saturated hydrocarbon groups having 5 to 12 carbon atoms, or substituted or absent atoms. It represents a cyclic saturated hydrocarbon group with 5 to 12 carbon atoms. Also, m, n, p, and s are respectively Each represents an integer between 0 and 3 independently, but any two or more of m, n, p, and s are independent. It represents an integer between 1 and 3.

[0026] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G5).

[0027] [ka]

[0028] However, in the above general formula (G5), R 1 ~R 4 at least one of them has 5 to 12 carbon atoms. This represents a saturated hydrocarbon group or a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. The remaining atoms are, independently, hydrogen, saturated hydrocarbon groups having 5 to 12 carbon atoms, or substituted or absent atoms. It represents a cyclic saturated hydrocarbon group with 5 to 12 carbon atoms. Also, m, n, p, and s are respectively Each represents an integer between 0 and 3 independently, but any two or more of m, n, p, and s are independent. It represents an integer between 1 and 3.

[0029] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G3).

[0030] [ka]

[0031] However, in the above general formula (G3), R 1 ~R 4 Each is independently hydrogen, carbon atoms with 5 or more 12 saturated hydrocarbon groups or substituted or unsubstituted cyclic saturated hydrocarbon groups having 5 to 12 carbon atoms It represents.

[0032] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G6).

[0033] [ka]

[0034] However, in the above general formula (G6), R 1 ~R 4 Each is independently hydrogen, carbon atoms with 5 or more 12 saturated hydrocarbon groups or substituted or unsubstituted cyclic saturated hydrocarbon groups having 5 to 12 carbon atoms It represents.

[0035] Alternatively, in another aspect of the present invention, in any of the above configurations, the R 1 ~R 4 Gashiku It is an organic compound containing a lohexyl group.

[0036] Alternatively, another aspect of the present invention is an organic compound represented by the following structural formula.

[0037] [ka]

[0038] Alternatively, another aspect of the present invention is an organic compound represented by the following structural formula.

[0039] [ka]

[0040] Alternatively, another aspect of the present invention comprises a first electrode, a second electrode, and the first electrode and the front The device has an EL layer located between the second electrodes, and the EL layer is one of the properties described above. This is a light-emitting element containing a chemical compound.

[0041] Alternatively, another aspect of the present invention comprises a first electrode, a second electrode, and the first electrode and the front The device has an EL layer located between the second electrodes, and the EL layer comprises at least an emissive layer and a hole A light-emitting element having a transport layer, wherein the hole transport layer contains any of the organic compounds described above. be.

[0042] Alternatively, another aspect of the present invention comprises a first electrode, a second electrode, and the first electrode and the front The device has an EL layer located between the second electrodes, and the EL layer comprises at least an emissive layer and a hole A light-emitting element having an injection layer, wherein the hole injection layer contains any of the organic compounds described above. be.

[0043] Alternatively, in another aspect of the present invention, a first electrode, a second electrode, the first electrode and the The device has an EL layer located between the second electrodes, and the EL layer comprises a light-emitting layer, a hole transport layer and The hole transport layer and the hole transport layer are provided with any of the above-mentioned organic materials. This is a light-emitting device containing a compound.

[0044] Alternatively, another aspect of the present invention is a light-emitting element described in any of the above, and a transistor, This is a light-emitting device having a substrate and a light-emitting device.

[0045] Alternatively, another aspect of the present invention includes the above-mentioned light-emitting device, a sensor, an operating button, a speaker, and , It is an electronic device that possesses [certain properties].

[0046] Alternatively, another aspect of the present invention is a lighting device having the above-mentioned light-emitting device and a housing.

[0047] Alternatively, another aspect of the present invention relates to an electronic device comprising the organic compound described in any of the above descriptions. be.

[0048] In this specification, the term "light-emitting device" includes image display devices that use light-emitting elements. Furthermore, a connector can be attached to the light-emitting element, for example, an anisotropic conductive film or TCP (Tape Carrier). A module with an aftermarket package attached, and a printed circuit board beyond the TCP. The installed module or light-emitting element uses the COG (Chip On Glass) method. Modules with directly mounted ICs (integrated circuits) may also be included in the category of light-emitting (display) devices. Furthermore, lighting fixtures and the like may have light-emitting devices. [Effects of the Invention]

[0049] In one aspect of the present invention, a novel organic compound can be provided. Or, in one aspect of the present invention Therefore, it is possible to provide novel organic compounds that have carrier transport properties. Or, this invention In one aspect of the present invention, a novel organic compound having hole transport properties can be provided. In one embodiment, an organic compound with a low refractive index can be provided. Or, an embodiment of the present invention This method provides an organic compound that has a low refractive index and carrier transport properties. Alternatively, in one aspect of the present invention, an organic compound having a low refractive index and hole transport properties is provided. It can be provided.

[0050] Alternatively, in another aspect of the present invention, a light-emitting element with high luminescence efficiency can be provided. Alternatively, in one aspect of the present invention, a light-emitting element, a light-emitting device, an electronic device, and a display device with low power consumption are provided. And electronic devices can be provided accordingly.

[0051] Furthermore, the description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. Furthermore, other effects are... This will become clear from the description in the specification, drawings, claims, etc., and the specification, drawings Furthermore, it is possible to extract other effects from the descriptions in the claims and other documents. [Brief explanation of the drawing]

[0052] [Figure 1] Schematic diagram of a light-emitting element. [Figure 2] Conceptual diagram of an active matrix light-emitting device. [Figure 3] Conceptual diagram of an active matrix light-emitting device. [Figure 4] Conceptual diagram of an active matrix light-emitting device. [Figure 5] Conceptual diagram of a passive matrix type light-emitting device. [Figure 6] A diagram representing a lighting device. [Figure 7] A diagram representing electronic devices. [Figure 8]A diagram representing electronic devices. [Figure 9] A diagram representing a lighting device. [Figure 10] A diagram representing a lighting device. [Figure 11] A diagram showing an in-vehicle display device and lighting system. [Figure 12] A diagram representing electronic devices. [Figure 13] A diagram representing electronic devices. [Figure 14] 1H NMR chart of TAPC-02. [Figure 15] Absorption and emission spectra of TAPC-02 in a 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-cyclohexane-diyl)bis{N-(4-cyclohexylphenyl)aminobenzene}. [Figure 19] 1H NMR chart of TAPC-03. [Figure 20] Brightness-current density characteristics of light-emitting element 1 and comparison light-emitting element 1. [Figure 21] Current efficiency-luminance characteristics of light-emitting element 1 and comparative light-emitting element 1. [Figure 22] Brightness-voltage characteristics of light-emitting element 1 and comparison light-emitting element 1. [Figure 23] Current-voltage characteristics of light-emitting element 1 and comparison light-emitting element 1. [Figure 24] External quantum efficiency-luminance characteristics of light-emitting element 1 and comparative light-emitting element 1. [Figure 25] Emission spectra of light-emitting element 1 and comparison light-emitting element 1. [Figure 26] Brightness-current density characteristics of light-emitting element 2. [Figure 27] Current efficiency-luminance characteristics of light-emitting element 2. [Figure 28] Brightness-voltage characteristics of light-emitting element 2. [Figure 29] Current-voltage characteristics of light-emitting element 2. [Figure 30] External quantum efficiency-luminance characteristics of light-emitting element 2. [Figure 31] Emission spectrum of light-emitting element 2. [Figure 32] Brightness-current density characteristics of light-emitting element 3. [Figure 33] Current efficiency-brightness characteristics of the light-emitting element 3. [Figure 34] Brightness-voltage characteristics of light-emitting element 3. [Figure 35] Current-voltage characteristics of light-emitting element 3. [Figure 36] External quantum efficiency-luminance characteristics of light-emitting element 3. [Figure 37] Emission spectrum of light-emitting element 3. [Figure 38] Refractive index of TAPC and TAPC-02 with respect to wavelength. [Modes for carrying out the invention]

[0053] The embodiments of the present invention will be described in detail below with reference to the drawings. However, the present invention is as follows Not limited to the description, the form and details thereof may be described without departing from the spirit and scope of the present invention. Those skilled in the art will readily understand that the invention can be modified in various ways. Therefore, the present invention is as follows: This should not be interpreted as being limited to the contents described in the embodiments.

[0054] (Embodiment 1) Among organic compounds with carrier transport properties that can be used in organic EL elements, One of the small materials is 1,1-bis-(4-bis(4-methylphenyl)-amino -phenyl)-cyclohexane (abbreviated as TAPC) is a known example. It is a material with a low refractive index. 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 by using TAPC, light-emitting devices with good external quantum efficiency can be obtained. However, TAPC has the problem of low heat resistance and being unreliable. .

[0055] One method for obtaining a highly heat-resistant and reliable hole transport material is unsaturated carbonization. One possibility is to introduce hydrogen groups, particularly cyclic unsaturated hydrocarbon groups, into the molecule.

[0056] On the other hand, obtaining a material with a low refractive index involves introducing substituents with low molecular refraction into the molecule. This is preferable. Examples of such substituents include saturated hydrocarbon groups and cyclic saturated hydrocarbon groups. can.

[0057] Furthermore, the material used as the carrier transport material for organic EL elements has a highly carrier-transportable skeleton. It is preferable that it has an aromatic amine skeleton, and in particular it is preferable that it has an aromatic amine skeleton.

[0058] Based on the above findings, the inventors have found that by combining these substituents and skeletons as follows, It has a low refractive index and is suitable for use as a hole transport material in organic EL elements. We discovered a compound that acts as a mechanism.

[0059] In other words, an organic compound according to one aspect of the present invention is an organic compound represented by the following general formula (G1). be.

[0060] [ka]

[0061] However, in the above general formula (G1), Ar 1 ~Ar 4 Each can be replaced or omitted independently. Substituted phenylene group, substituted or unsubstituted biphenyldiyl group and substituted or unsubstituted Represents any of the triphenyldiyl groups.

[0062] Note that Ar 1 and Ar 4 The phenylene group is preferably substituted or unsubstituted, and unsubstituted phenylene is preferred. A nilen group is even more preferable considering the synthesis cost.

[0063] Also, Ar 2 and Ar 3 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted phenylene group. A biphenyldiyl group is preferred, and a substituted or unsubstituted phenylene group improves sublimation. Therefore, it is preferable. Also, considering the synthesis cost, an unsubstituted phenylene group is even more preferable. It's nice.

[0064] Ar 1 ~Ar 4 A phenylene group having a substituent, or a biphenyl group having a substituent. In the case of a diyl group and a triphenyldiyl group having a substituent, the substituent may be: Examples include alkyl groups having 1 to 4 carbon atoms. For example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-propyl group Examples include the tyl group, isobutyl group, and tert-butyl group.

[0065] As mentioned above, Ar 1 ~Ar 4 It is preferable that it is an unsubstituted phenylene group. The organic compound in question can be represented by the following general formula (G2).

[0066] [ka]

[0067] Furthermore, in the above general formula (G1), as described above, Ar 2 and Ar 3 is a non-substituted Bif It is an phenyldiyl group, Ar 1 and Ar 4 It is preferable that it be an unsubstituted phenylene group. Such organic compounds can be represented by the following general formula (G4).

[0068] [ka]

[0069] Furthermore, in the above general formula (G1), Ar 2 and Ar 3 is an unsubstituted biphenyldiyl group And Ar 1 and Ar 4 It is preferable that is an unsubstituted phenylene group, but Ar 2 oh Call Ar 3 It is more preferably an unsubstituted 4,4'-biphenyldiyl group. Such organic compounds can be represented by the following general formula (G5).

[0070] [ka]

[0071] Furthermore, the odor of organic compounds represented by the above general formulas (G1), (G2), (G4), and (G5) However, m, n, p, and s each independently represent integers from 0 to 3, but m, n, p, and s Any two or more of these terms shall independently represent an integer between 1 and 3.

[0072] Furthermore, from the viewpoint of ease of synthesis and stability, it is preferable that m, n, p, and s are 1. However, among the organic compounds represented by the above general formulas (G4) and (G5), such organic compounds Objects can be represented by the following general formulas (G3) and (G6).

[0073] [ka]

[0074] [ka]

[0075] In addition, in the above general formulas (G1) to (G6), R 1 ~R 4 Each of these independently determines the number of carbon atoms. 5 to 12 saturated hydrocarbon groups or substituted or unsubstituted cyclic saturated carbons with 5 to 12 carbon atoms It represents a hydrogenated group.

[0076] Examples of saturated hydrocarbon groups having 5 to 12 carbon atoms include pentyl group, isopentyl group, and sec-Penyl group. pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 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 dimethyloctyl group, decane group, 2,6-dimethyloctyl group, 3,3-dimethyloctyl group, 2-dimethyloctyl group Examples include the methylnonyl group, 3-methylnonyl group, undecyl group, and dodecyl group. Examples of cyclic saturated hydrocarbon groups having 5 to 12 carbon atoms include the cyclopentyl group and the cyclohexyl group. , 1-methylcyclopentyl group, 2-methylcyclopentyl group, cycloheptyl group, bicyl Chlo[2,2,1]heptyl group, cyclooctyl group, bicyclo[2,2,2]octyl group 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 Examples include the dodecyl group.

[0077] Also, R 1 ~R 4 Any of these is a cyclic hydrocarbon group having 5 to 12 carbon atoms and having substituents. In this case, examples of substituents include alkyl groups having 1 to 4 carbon atoms. Examples of alkyl groups with prime numbers 1 to 4 include methyl, ethyl, propyl, and isopropyl groups. Examples include n-butyl group, sec-butyl group, isobutyl group, and tert-butyl group. can.

[0078] Note, R 1 ~R 4 These substituents have the same number of carbon atoms in terms of atomic or molecular refraction. Therefore, a substituent with a cyclic structure is effective in further reducing the refractive index. Therefore, ring substituents with 6 or more members and medium-sized ring substituents are more preferred. However, large-ring substituents are preferred. Introducing a substitution group may increase the molecular weight, potentially reducing sublimation properties. Therefore, it is possible that this could lead to decomposition, and thus it is a cyclohexyl group. It is preferable.

[0079] Organic compounds having the above configuration have a low refractive index and possess hole transport properties. It is a compound. Therefore, a light-emitting device using this organic compound has good external quantum efficiency. It can be used as a light-emitting element.

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

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] Next, according to one aspect of the present invention, a method for synthesizing an organic compound represented by the following general formula (G1) Let me give you an example.

[0091] [ka]

[0092] In the above general formula (G1), Ar 1 ~Ar 4 These are, independently, substitution or non-substitution. Phenylene group, substituted or unsubstituted biphenyldiyl group and substituted or unsubstituted tri Represents any of the phenyldiyl groups. Also, R 1 ~R 4 Each of them independently has 5 carbon atoms. Saturated hydrocarbon groups of up to 12 carbon atoms or substituted or unsubstituted cyclic saturated hydrocarbons having 5 to 12 carbon atoms. It represents the base. Also, m, n, p, and s each independently represent an integer from 1 to 3.

[0093] The organic compound represented by the above general formula (G1) is synthesized as shown in the synthesis scheme below: 1,1- Bis(4-aminophenyl)cyclohexane and an organic halide are subjected to a gold reaction in the presence of a base. It can be synthesized by coupling with a metal catalyst, metal, or metal compound. Cut.

[0094] [ka]

[0095] In the above synthesis scheme, Ar 1 ~Ar 4 Each of these independently determines whether the substitution or non-substitution is true. phenylene group, substituted or unsubstituted biphenyldiyl group and substituted or unsubstituted triphen It represents one of the nyldiyl groups. Also, R 1 ~R 4 Each of them independently has 5 to 1 carbon atoms. Two saturated hydrocarbon groups or substituted or unsubstituted cyclic saturated hydrocarbon groups having 5 to 12 carbon atoms It represents a number. Also, m, n, p, and s each independently represent an integer between 1 and 3.

[0096] When the above synthesis scheme is carried out as a Buchwald-Hartwig reaction, X is a halogen or This represents a triflate group. Iodine, bromine, or chlorine are preferred halogens. In the reaction, bis(dibenzylideneacetone)palladium(0) and allyl palladium chloride are produced. Palladium complexes or compounds such as mer(II) and tri(tert-butyric) that coordinate thereto Phosphines and dimethyl-2,2-diphenylcyclopropyl Palladium catalysts using ligands such as phosphine or tricyclohexylphosphine are utilized. It is used as a base. Examples of bases include organic bases such as sodium tert-butoxide and potassium carbonate. Examples of inorganic bases include the following. Furthermore, when using solvents, toluene, xylene, 1,3 ,5-trimethylbenzenebenzene, etc., can be used.

[0097] Furthermore, when the above synthesis scheme is carried out as an Ullmann reaction, X represents a halogen. Iodine, bromine, or chlorine are preferred as catalysts. Copper or copper compounds are used as catalysts. It is preferable to use copper(I) iodide or copper(II) acetate. Examples of suitable bases include inorganic bases such as potassium carbonate. The solvent is 1,3-dimethyl -3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), N-methyl- 2-pyrrolidone (NMP), toluene, xylene, 1,3,5-trimethylbenzene, etc. Use. However, the solvents are not limited to these. In the Ullmann reaction, reaction temperature Since the target product can be obtained in a shorter time and with higher yield at temperatures above 100°C, DM with a high boiling point is used. It is preferable to use PU, NMP, and 1,3,5-trimethylbenzene. Also, the reaction temperature Since a higher temperature of 150°C or above is even more preferable, it is more preferable to use a DMPU. Let's do it this way.

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

[0099] (Embodiment 2) Figure 1 shows a diagram representing a light-emitting element according to one aspect of the present invention. The light-emitting element according to one aspect of the present invention is first It has an electrode 101, a second electrode 102, and an EL layer 103, and the EL layer is provided in the first embodiment The organic compounds shown are used.

[0100] The EL layer 103 has an emissive layer 113, a hole injection layer 111 and / or hole transport layer. It may also have layer 112. The light-emitting layer 113 contains a light-emitting material, which is one embodiment of the present invention. The light-emitting element obtains light from the light-emitting material. The light-emitting layer 113 contains a host material and its Other materials may be included. The organic compound of one embodiment of the present invention shown in Embodiment 1 is Whether included in the light-emitting layer 113, or included in the hole transport layer 112, or the hole injection layer 111 It doesn't matter if it's included in one of them, or in any of them.

[0101] In addition to these, Figure 1 also shows an electron transport layer 114 and an electron injection layer 115. However, the configuration of the light-emitting element is not limited to these.

[0102] Because this organic compound has good hole transport properties, it is effective to use it in the hole transport layer 112. Furthermore, in one embodiment of the present invention, an organic compound is mixed with an acceptor substance. The resulting film can be used as a hole injection layer 111.

[0103] Furthermore, an organic compound according to one embodiment of the present invention can also be used as a host material. Furthermore, by co-depositing with an electron transport material, the electron transport material and hole transport material The configuration may also be one that forms an excited complex. This enables effective energy transfer to the light-emitting material, resulting in high efficiency and a long lifespan. It becomes possible to provide a light-emitting element.

[0104] The organic compound in one aspect of the present invention is an organic compound with a low refractive index, and therefore it is placed within the EL layer By using this in the part, it is possible to obtain a light-emitting element with good external quantum efficiency.

[0105] Next, we will describe the detailed structure and material examples of the light-emitting element described above. As described above, the optical element has multiple layers between the pair of electrodes, the first electrode 101 and the second electrode 102. It has an EL layer 103 made of the following, and any part of the EL layer 103 is, It contains the organic compounds disclosed in 1.

[0106] The first electrode 101 is made of a metal, alloy, or conductive material with a large work function (specifically, 4.0 eV or more). It is preferable to form them using chemical compounds and mixtures thereof. Specifically, for example, For example, indium tin oxide (ITO), silica Indium oxide-tin oxide and indium oxide-zinc oxide containing silicon dioxide or silicon dioxide. Examples include indium oxide (IWZO) containing tungsten oxide and zinc oxide. These conductive metal oxide films are usually deposited by sputtering, but sol-ge It is also acceptable to use methods such as the Lu method for fabrication. An example of a fabrication method is indium oxide-oxide Zinc is used in a target where 1-20 wt% zinc oxide is added to indium oxide. Methods include forming by the puttering method. Additionally, tungsten oxide and zinc oxide are used. The contained indium oxide (IWZO) has a ratio of 0.5% to tungsten oxide relative to indium oxide. Sputtering is performed using a target containing 5-5 wt% zinc oxide and 0.1-1 wt% zinc oxide. It can also be formed by law. Other materials include gold (Au), platinum (Pt), and 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) Examples include (n). Graphene can also be used. Note that the composite material described later is EL By using it in the layer that is in contact with the first electrode 101 in layer 103, regardless of the work function, It will become possible to select the polar materials.

[0107] The EL layer 103 preferably has a laminated structure, but the laminated structure is not particularly limited. There is no fixed structure, and it consists of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier block layer, and an excitation layer. Various layer structures can be applied, such as a riser block layer and a charge generation layer. Then, as shown in Figure 1(A), the hole injection layer 111, hole transport layer 112, and light-emitting layer 113 In addition, a configuration having an electron transport layer 114 and an electron injection layer 115, as shown in Figure 1(B) In addition to the hole injection layer 111, hole transport layer 112, and light emission layer 113, there is also an electron transport layer 114 Two types of configurations will be described: one having an electron injection layer 115 and a charge generation layer 116. The materials that make up each layer are described below in detail.

[0108] The hole injection layer 111 is a layer containing a substance having acceptor properties. Both organic and inorganic compounds can be used as materials.

[0109] Substances that exhibit acceptor properties include compounds containing electron-withdrawing groups (halogen groups or cyano groups). It is possible to use the substance, 7,7,8,8-tetracyano-2,3,5,6-tetrafluor Roquinodimethane (abbreviation: F4-TCNQ), 3,6-difluoro-2,5,7,7,8, 8-Hexacyanoquinodimethane, chloranil, 2,3,6,7,10,11-Hexacyanoquinodimethane 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 for organic compounds that possess this, there are condensed aromatic rings with multiple heteroatoms, such as HAT-CN, and Compounds to which electron-withdrawing groups are attached are thermally stable and preferred. Also, electron-withdrawing groups (especially Radialene derivatives having halogen groups such as fluoro groups or cyano groups [3] are electron-receiving It is preferred because it has very high capacity, specifically α,α',α''-1,2,3-cyclopro Pantryiridentris[4-cyano-2,3,5,6-tetrafluorobenzeneaceto Nitrile], α,α',α''-1,2,3-cyclopropane triylidenates[2, 6-Dichloro-3,5-Difluoro-4-(trifluoromethyl)benzeneacetonite [Lu], α,α',α''-1,2,3-cyclopropanetriylidentris[2,3,4 Examples include [5,6-pentafluorobenzeneacetonitrile]. Acceptance In addition to the organic compounds mentioned above, other substances that possess these compounds include molybdenum oxide and vanadic acid. Can be used as oxides, ruthenium oxide, tungsten oxide, manganese oxide, etc. In addition, there are other types of phthalocyanines such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPC). Cyanine-based 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 (Lu)-4,4'-diamine (abbreviation: DNTPD), or poly( 3,4-Ethylenedioxythiophene) / Poly(styrenesulfonic acid)(PEDOT / P The hole injection layer 111 can also be formed by polymers such as SS. Acceptability A material having this property can be subjected to the application of an electric field from an adjacent hole transport layer (or hole transport material). It can extract electrons.

[0110] Furthermore, the hole injection layer 111 contains an acceptor substance in addition to a hole transport substance. Composite materials can also be used. Furthermore, a hole-transporting material can contain an acceptor material. By using composite materials, it is possible to select materials for forming electrodes regardless of the work function. In other words, the first electrode 101 can be made not only of materials with a large work function, but also of materials with a small work function. Other materials can also be used. Examples of such acceptable substances include 7, 7, and 8. ,8-Tetracyano-2,3,5,6-Tetrafluoroquinodimethane (abbreviation: F4-TC NQ), chloranil, 1,3,4,5,7,8-hexafluorotetracyano-naphthoxy Organic compounds with acceptor properties such as nodimethane (abbreviation: F6-TCNNQ), and transition gold Examples include group oxides. Also, metals belonging to groups 4 through 8 of the periodic table. Oxides of metals belonging to groups 4 through 8 of the periodic table can also be used. Examples of oxides include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, and molybdenum oxide. Compounds such as tungsten oxide, manganese oxide, and rhenium oxide are preferred due to their high electron-accepting properties. Among them, molybdenum oxide is particularly preferred because it is stable in the atmosphere, has low hygroscopicity, and is easy to handle.

[0111] As the hole-transporting material used in the composite material, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, and polymer compounds (oligomers, dendrimers, polymers, etc.) can be used. In addition, as the hole-transporting material used in the composite material, it is preferably a substance having a hole mobility of 10 cm -6 / Vs or more. Hereinafter, 2 organic compounds that can be used as the hole-transporting material in the composite material will be specifically listed.

[0112] Examples of the aromatic amine compound that can be used in the composite material include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 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)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl amino]benzene (abbreviation: DPA3B), 1,1-bis-(4-bis(4-methyl-f enyl)-amino-phenyl)-cyclohexane (abbreviation: TAPC), etc. Examples of the carbazole derivative include, specifically, 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPC) <00919>​​​​​ A1) 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenyl Mino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl [Lu)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: 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-phenylanthracene-9-yl)phenyl]-9H- Luvazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]- 2,3,5,6-tetraphenylbenzene and the like can be used. As aromatic hydrocarbons For example, 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated) Name: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthrate Sen, 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-butylant Spiral (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)an Transene (abbreviation: DMNA), 2-tert-butyl-9,10-bis[2-(1-naphthol [2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene Tracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene , 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9 '-biantryl,10,10'-diphenyl-9,9'-biantryl,10,10' -Bis(2-phenylphenyl)-9,9'-biantryl,10,10'-bis[(2 ,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthrace n, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl) Examples include perylene. In addition, pentacene, coronene, and the like can also be used. It may have a vinyl skeleton. Examples of aromatic hydrocarbons having a vinyl group include , 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9 ,10-Bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DP) Examples include VPA. Furthermore, an organic compound according to 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] Also, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenyl (Abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine) [Phenylamino(N'-phenylamino)phenyl(N'-phenylamino)phenyl(methacrylamide) (abbreviated) Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( High molecular weight compounds such as phenyl(benzidine) (abbreviated as Poly-TPD) can also be used. Cut.

[0114] Furthermore, the organic compound of one embodiment of the present invention disclosed in Embodiment 1 is also a material that has hole transport properties. Yes, it can be preferably used as a hole-transporting substance for the composite material. In the present invention By using the organic compound of one embodiment, a layer with a low refractive index can be formed inside the EL layer 103 and the external quantum efficiency of the light-emitting device can be improved.

[0115] In addition, by further mixing a fluoride of an alkali metal or an alkaline earth metal with the above composite material (preferably the atomic ratio of fluorine atoms in the layer is 20% or more), the refractive index of the layer can be reduced. Also by this, a layer with a low refractive index can be formed inside the EL layer 103, and the external quantum efficiency of the light-emitting device can be improved. By forming the hole injection layer 111, the hole injection property becomes good, and a light-emitting device with a small driving voltage can be obtained. Also, the organic compound having an acceptor property is easy to vaporize

[0116] and easy to form a film, so it is a material that is easy to use. The hole transport layer 112 is formed by including a material having hole transport properties. As the material having hole transport properties, it preferably has a hole mobility of 1×10 cm

[0117] / Vs or more. The hole transport layer 112 preferably contains the organic compound of one embodiment of the present invention. By including the organic compound described in Embodiment Form 1 in the hole transport layer 112, a layer with a low refractive index can be formed inside the EL layer 103, and it becomes possible to improve the external quantum efficiency of the light-emitting device. -6 cm 2 / Vs or more. The hole transport layer 112 preferably contains the organic compound of one embodiment of the present invention. By including the organic compound described in Embodiment Form 1 in the hole transport layer 112, a layer with a low refractive index can be formed inside the EL layer 103, and it becomes possible to improve the external quantum efficiency of the light-emitting device. The hole transport layer 112 preferably contains the organic compound of one embodiment of the present invention. By including the organic compound described in Embodiment Form 1 in the hole transport layer 112, a layer with a low refractive index can be formed inside the EL layer 103, and it becomes possible to improve the external quantum efficiency of the light-emitting device. possible.

[0118] Examples of the material having hole transport properties include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)- 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 [Luaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorine) Len-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-( 9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4 -phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (Abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H- Carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1- Naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)-triphenyl Mine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl -9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9 -dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl] )phenyl]-fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4 -(9-phenyl-9H-carbazole-3-yl)phenyl]-spiro-9,9'-bi Compounds having an aromatic amine skeleton, such as fluoren-2-amine (abbreviated as PCBASF) or, 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-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl- Compounds having a carbazole skeleton, such as 9H-carbazole (abbreviated as PCCP), and 4 ,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated) Name: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-full Oren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4 -[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldiphenyl Compounds containing a thiophene skeleton, such as nzzothiophene (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) and other furans Compounds having an aromatic amine skeleton are examples. Among those mentioned above, compounds having an aromatic amine skeleton are examples. Compounds with a carbazole skeleton are reliable and have high hole transport properties. This is preferable because it also contributes to reducing the driving voltage. Furthermore, it is used in the composite material of the hole injection layer 111. The materials listed as having hole transport properties are also suitable as materials for constituting the hole transport 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 substance. Even if it is a phosphorescent material, or a material that exhibits thermally activated delayed fluorescence (TADF) Other light-emitting materials are also acceptable. Furthermore, even if it is a single layer, it may contain different light-emitting materials. It may consist of multiple layers.

[0120] In the light-emitting layer 113, possible materials that can be used as fluorescent light-emitting materials include, for example, Examples include those listed below. Other fluorescent materials can also be used.

[0121] 5,6-Bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyri Zin (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-antri [Lu)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bi Su(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-carb Zole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine ( Abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diph Phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diph phenyl-N-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole ru-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert -Butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'- (9-phenyl-9H-carbazole-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-carbazole-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]Crystal N-2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N-(9, 10-Diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazole-3- Amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-i [Lu)-2-anthryl]-N,9-diphenyl-9H-carbazole-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'-to Riphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis (1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl) [phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N ,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), coumarin 54 5T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubren, 5,12-bi Su(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-meth Ru-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidi [-9-yl)ethenyl]-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]fluorantene-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 ]Quinolysin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitol Lu (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidine [-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 Trahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-p Lan-4-ylidene propanedinitrile (abbreviation: BisDCJ™), N,N'-diph Phenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naph [1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), etc. These include, in particular, 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6Bn Condensed aromatic diamine compounds, such as pyrendiamine compounds like fAPrn-03 This is preferable because it has high hole-trapping properties and excellent luminescence efficiency and reliability.

[0122] Examples of materials that can be used as phosphorescent materials in the light-emitting layer 113 include, for example, The following are some examples.

[0123] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazole-3-yl-κN2]phenyl-κC}iridium(III ) (abbreviation: [Ir(mpptz-dmp)3]), Tris(5-methyl-3,4-diphen) Iridium(III) (abbreviation: [Ir(Mpt) z)3]), Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-Triazolat] Iridium(III) (Abbreviation: [Ir(iPrptz-3 Organometallic iridium complexes having a 4H-triazole skeleton, such as b)3]), and Tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-tria Zolato] Iridium (III) (abbreviation: [Ir(Mptz1-mp)3]), Tris (1 -Methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium (III) (Abbreviation: [Ir(Prptz1-Me)3]) 1H-triazole bone iridium organometallic complexes with a specific classification, and fac-tris[(1-2,6-diisopropyl [Phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi)3]), Tris[3-(2,6-dimethylphenyl)-7-methylimi Dazo[1,2-f]phenantriginato]iridium(III) (abbreviation:[Ir(dmp Organometallic iridium complexes having an imidazole skeleton such as impt-Me)3]), Bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ ]iridium( III) Tetrakis(1-pyrazolyl)borate (abbreviation: Fir6), bis[2-(4' ,6'-Difluorophenyl)pyridinate-N,C 2’ Iridium(III) picolina Firpic (abbreviation: Firpic), bis{2-[3',5'-bis(trifluoromethyl) [enyl]pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: [Ir( CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyri Dinato-N,C 2’ Iridium(III) acetylacetonate (abbreviation: FIraca) organometallic iridium ligands having electron-withdrawing groups as shown in c) Examples include um complexes. These are compounds that exhibit blue phosphorescence, starting from 440 nm. This compound has an emission peak at 520 nm.

[0124] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato)yli Dium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp) pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidina) Iridium(III) (Abbreviation: [Ir(tBuppm)2(ac (ac)), (acetylacetonate)bis[6-(2-norbornyl)-4-phenylp Limiginato Iridium(III) (abbreviation: [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)]) has a pyrimidine skeleton iridium metal complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl Iridium(III) (abbreviation: Ir(mppr-Me)2(acac)) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyra) Dinato-iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) organometallic iridium complexes having a pyrazine skeleton, such as tris(2-phenylpyridium Nato-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]quinolinate) iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), Tris(be Iridium (III) (abbreviation: [Ir(bzq)3]), Tris (2-phenylquinolinato-N,C 2’ Iridium(III) (abbreviation: [Ir(pq) 3]), bis(2-phenylquinolinato-N,C 2’ Iridium(III) acetylated Setanate (abbreviation: [Ir(pq)2(acac)]) is a pyridine skeleton-containing substance In addition to iridium metal complexes, tris(acetylacetonate)(monophenanthroline) Rare earth metals such as rubium(III) (abbreviation: [Tb(acac)3(Phen)]) Examples include complexes. These are compounds that mainly exhibit green phosphorescence, starting from 500 nm. It has an emission peak at 600 nm. Note that it is an organometallic iridium with a pyrimidine skeleton. The complex is particularly preferred because it exhibits outstanding reliability and luminescence efficiency.

[0125] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimid Sodium iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis(Ir(5mdppm)2(dibm)]), [4,6-Bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridi Um(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalene-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organometallic gold with a pyrimidine skeleton, such as (abbreviation: [Ir(d1npm)2(dpm)]) Iridium complexes of the genus, and (acetylacetonato)bis(2,3,5-triphenylpyrazine Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-Triphenylpyrazinate)(dipivaloylmethanato) Iridium(III) (abbreviated) Name: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bi [Ir(4-fluorophenyl)quinoxalinato] Iridium(III) (abbreviation: [Ir(F Organometallic iridium complexes having a pyrazine skeleton such as dpq)2(acac)]), Tris(1-phenylisoquinolinato-N,C) 2’ ) Iridium(III) (abbreviation: [I r(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium (I II) Pyrrhizic acid like acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with a din skeleton, 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-propanedionato)(monof Phenanthroline Europium(III) (Abbreviation: [Eu(DBM)3(Phen)]) Tris[1-(2-tenoyl)-3,3,3-trifluoroacetonate](monofena (Eu(TTA)3(Phen)) Examples include rare earth metal complexes. These are compounds that exhibit red phosphorescence, and 6 It has an emission peak from 00 nm to 700 nm. It is also an organometallic compound with a pyrazine skeleton. Iridium complexes produce a red emission with good chromaticity.

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

[0127] TADF materials include fullerenes and their derivatives, acridines and their derivatives, and eosin. Derivatives can be used. Also, magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P Examples of metal-containing porphyrins include those described in d). For example, the protoporphyrin-tin fluoride complex (SnF2(Pro to IX), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), copropol Filinetetramethyl ester-tin fluoride complex (SnF2(Copro III-4M) e) Octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethiopropyl Rufirin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin - Examples include platinum chloride complexes (PtCl2OEP), etc.

[0128] [ka]

[0129] Furthermore, the following structural formula shows 2-(biphenyl-4-yl)-4,6-bis(12-) Enylindoro[2,3-a]carbazole-11-yl)-1,3,5-triazine( Abbreviations: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- Il)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT) Zn), 9-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl [Lu]-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzPT) Zn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diph Phenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl -5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1, 2,4-Triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-A Cryzin-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 (abbreviated as ACRSA) Heterocyclic compounds having both a π-electron-deficient heteroaromatic ring and a heterocyclic aromatic ring can also be used. The compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, therefore electron transport Both the properties and hole transport properties are high, which is preferable. Note that the π-electron-rich heteroaromatic ring and the π-electron-deficient type Substances directly bonded to a heteroaromatic ring exhibit characteristics of both π-electron-rich heteroaromatic ring donor and π-electron-deficient heteroaromatic rings. The acceptability of the complex aromatic rings is strengthened, and the energy difference between the S1 and T1 levels is reduced. Therefore, it is particularly preferable because thermally activated delayed fluorescence can be obtained efficiently. Instead of a foot-shaped heteroaromatic ring, an aromatic ring bonded with an electron-withdrawing group such as a cyano group may also be used. stomach.

[0130] [ka]

[0131] The host material for the light-emitting layer can be various materials such as electron-transporting materials or hole-transporting materials. Various carrier transport materials can be used.

[0132] As a material having hole transport properties, the material having hole transport properties included in the hole transport layer 112 The materials listed can be used suitably.

[0133] Examples of materials with electron transport properties include bis(10-hydroxybenzo[h]quinoli Sodium beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolate) )(4-phenylphenolate)aluminum(III) (abbreviation: BAlq), bis(8- Zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) [Phenolate]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) Metal complexes such as phenolate zinc(II) (abbreviation: ZnBTZ) and 2-(4-biphenyl Ryl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation) :PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butyl) Enyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-te rt-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl) Phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5 -Benzenetriyl)tris(1-phenyl-1H-benzoimidazole) (abbreviation: TP) BI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H -Polyazole skeletons such as benzimidazole (abbreviation: mDBTBIm-II) Heterocyclic compounds, and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f ,h]Quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothio [fen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2 mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl)bipheni [Lu-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 4,6 -Bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn) P2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation) Heterocyclic compounds having a diazine skeleton, such as 4,6 mDBTP2Pm-II, and 3,5 -Bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCz) PPy), 1,3,5-tri[3-(3-pyridyl)-phenyl]benzene (abbreviation: Tm Examples include heterocyclic compounds having a pyridine skeleton, such as PyPB. Among those mentioned above, Heterocyclic compounds with an azine skeleton or a pyridine skeleton are highly reliable. This is preferable. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton are preferable. It also has high electron transport properties and contributes to reducing the drive voltage.

[0134] When using fluorescent materials as light-emitting materials, the host material should have an anthracene skeleton. Materials that are suitable for this purpose are used as host materials for fluorescent materials. When used in this way, it is possible to realize a light-emitting layer with good luminous efficiency and durability. Since many materials having a sen skeleton have deep HOMO levels, one aspect of the present invention is suitably applied. It is possible. As for materials having an anthracene skeleton to be used as a host material, A substance having a phenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton It is preferable because it is chemically stable. Also, if the host material has a carbazole skeleton, This is preferable because it improves hole injection and transport, but the benzene ring is further condensed on the carbazole. When it contains a benzocarbazole skeleton, the HOMO is approximately 0.1 eV shallower than that of carbazole. This is preferable because it makes it easier for holes to enter. In particular, if the host material is dibenzocarbazo When a carbazole skeleton is present, the HOMO becomes about 0.1 eV shallower than that of carbazole, and holes are inserted. It is preferable because it becomes easier to transport holes, has excellent hole transport properties, and has high heat resistance. Furthermore, preferred host materials include a 9,10-diphenylanthracene skeleton and The carbazole skeleton (or benzocarbazole skeleton or dibenzocarbazole skeleton) It is a substance that sometimes possesses this property. Furthermore, from the viewpoint of the hole injection and transport properties mentioned above, the carbazole skeleton is Alternatively, a benzofluorene skeleton or a dibenzofluorene skeleton may be used. An example of quality is 9-phenyl-3-[4-(10-phenyl-9-antryl)phenyl [Lu]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)-pheny [L]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl] [nyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7- [4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]cal Bazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-ant) [Lyl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA) ), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)bife Examples include ny-4'-ylanthracene (abbreviated as FLPPA). In particular, CzPA cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good characteristics, therefore, That was a good choice.

[0135] Furthermore, the host material may be a mixture of multiple substances, and the mixed host material When used, a mixture of electron-transporting material and hole-transporting material is used. Preferably, by mixing an electron-transporting material with a hole-transporting material. Furthermore, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. This is possible. The ratio of the content of hole-transporting material to electron-transporting material is the ratio of hole-transporting material content. The ratio of electron-transporting material to electron-transporting material should be 1:9 to 9:1.

[0136] Furthermore, these mixed materials may form excited complexes. These excited complexes are luminescent materials. It forms an excited complex that emits light that overlaps with the wavelength of the lowest energy absorption band. By selecting the right combination, energy transfer becomes smoother, and luminescence is obtained more efficiently. This is preferable because it allows for a reduction in the drive voltage.

[0137] The electron transport layer 114 is a layer containing a substance that has electron transport properties. As examples, the above-mentioned materials are electron-transporting substances that can be used as host materials. You can use this.

[0138] Between the electron transport layer 114 and the second electrode 102, an electron injection layer 115 is provided, which is lithium fluoride. Aquatic compounds such as LiF (Lithium Fibre), Cesium fluoride (CsF), and Calcium fluoride (CaF2) A layer containing a lucid metal, an alkaline earth metal, or a compound thereof may be provided. Electron injection Layer 115 is a layer made of an electron-transporting material containing alkali metals or alkaline earth metals. Alternatively, a substance containing those compounds or an electride may be used. For example, a mixture of calcium and aluminum oxide with a high concentration of electrons added. Quality and other factors can be cited.

[0139] Furthermore, the electron injection layer 115 is made of a substance having electron transport properties (preferably a bipyridine skeleton). (An organic compound containing) the above alkali metal or alkaline earth metal fluoride in a microcrystalline state It is also possible to use a layer containing a concentration of 50 wt% or more. This layer is refraction Because it is a low-efficiency layer, it is possible to provide a light-emitting element with better external quantum efficiency. Yes.

[0140] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (Figure 1(B)). The charge generation layer 116 generates holes in the layer in contact with the cathode side of the layer when an electric potential is applied, and in the anode side. This refers to a layer that can inject electrons into the adjacent layer. The charge generation layer 116 has a small amount of At the very 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 it using the composite materials listed as materials that can be used. Also, the P-type layer 1 17 is a film containing the above-mentioned acceptor material and hole transport material as materials constituting the composite material. It may also be constructed by stacking films containing the P-type layer 117. By applying a potential to the P-type layer 117, electrons 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. Furthermore, since the organic compound of one aspect of the present invention is an organic compound with a low refractive index, P By using it in the mold layer 117, a light-emitting element with good external quantum efficiency can be obtained.

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

[0142] The electron relay layer 118 contains at least an electron-transporting material, and the electron injection buffer layer 1 It has the function of preventing interaction between 19 and the P-type layer 117, thereby enabling smooth electron transfer. The LUMO level of the electron-transporting material contained in the relay layer 118 is in the P-type layer 117. The LUMO level of the acceptor material and the charge generation layer 116 in the electron transport layer 114 It is preferable that the LUMO level is between the LUMO level of the material contained in the contacting layer. Electron relay layer 11 Specific energy levels of the LUMO level in electron-transporting materials used in 8 The voltage should be -5.0 eV or higher, preferably -5.0 eV to -3.0 eV. As for electron-transporting materials used in the electron relay layer 118, phthalocyanine-based materials are used. It is preferable to use a material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0143] The electron injection buffer layer 119 contains alkali metals, alkaline earth metals, rare earth metals, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, and carbonates) (including carbonates such as thium and cesium carbonate), alkaline earth metal compounds (oxides, halogens) Compounds of rare earth metals (including oxides, halides, and carbonates), or compounds of rare earth metals (including oxides, halides, and carbonates) It is possible to use materials with high electron injection capabilities, such as (m)).

[0144] Furthermore, the electron injection buffer layer 119 contains an electron transporting substance and a donor substance, and If performed, alkali metals, alkaline earth metals, and rare earth metals will be used as donor substances. , and these compounds (alkali metal compounds (oxides and halides such as lithium oxide) , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, (including halides and carbonates), or compounds of rare earth metals (oxides, halides, carbon In addition to salts, tetratianaphthacene (abbreviated as TTN), nickerosene, decametine Organic compounds such as runicerosene can also be used. Therefore, it is formed using the same material as the material that constitutes the electron transport layer 114 described earlier. It is possible.

[0145] The material forming the second electrode 102 has a small work function (specifically, 3.8 eV or less). (Below) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkaline materials such as lithium (Li) and cesium (Cs). Metallic compounds, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or Group 2 of the periodic table, and alloys containing these elements (MgAg, Rare earth metals such as AlLi, europium (Eu), ytterbium (Yb), and this Examples include alloys containing these. However, between the second electrode 102 and the electron transport layer, By providing an electron injection layer, regardless of the magnitude of the work function, Al, Ag, ITO, and silica can be used. Various conductive materials such as indium oxide-tin oxide containing silicon dioxide or silicon dioxide are used as the second... These conductive materials can be used as electrodes 102. It is possible to deposit films using dry methods such as the smear method, inkjet methods, spin coating methods, etc. It is possible to form it using a wet method with the sol-gel method, or by using a paste of a metal material. It may also be formed by a wet process.

[0146] Furthermore, various methods can be used to form the EL layer 103, regardless of whether they are dry or wet methods. This can be done using methods such as vacuum deposition, gravure printing, offset printing, and screen printing. You may use methods such as printing, inkjet printing, or spin coating.

[0147] Furthermore, each electrode or layer described above may be formed using different film deposition methods.

[0148] The configuration of the layer provided between the first electrode 101 and the second electrode 102 is as described above. It is not limited to this. However, if the light-emitting region and the metal used in the electrodes or carrier injection layer are in close proximity To suppress the quenching that occurs as a result, the first electrode 101 and the second electrode 1 A configuration is preferred in which a light-emitting region is provided at a location away from O2 where holes and electrons recombine.

[0149] Furthermore, the hole transport layer and electron transport layer in contact with the light-emitting layer 113, and especially the recombination in the light-emitting layer 113, The carrier transport layer near the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is the light-emitting material that makes up the light-emitting layer or the light contained in the light-emitting layer. It is preferable to use materials with a band gap larger than the band gap of the material itself. It seems so.

[0150] Next, a light-emitting element with a configuration in which multiple light-emitting units are stacked (stacked element, tandem element and The embodiment of (also known as) will be explained with reference to Figure 1(C). This light-emitting element has an anode and a cathode Between them is a light-emitting element having multiple light-emitting units. One light-emitting unit is shown in Figure 1( It has a configuration almost identical to the EL layer 103 shown in A). In other words, the light-emitting element shown in Figure 1(C) The child is a light-emitting element having multiple light-emitting units, as shown in Figure 1(A) or Figure 1(B). An optical element can be described as a light-emitting element having one light-emitting unit.

[0151] In Figure 1(C), a first light-emitting unit 511 and a cathode 502 are located between the anode 501 and the cathode 502. A second light-emitting unit 512 is stacked with the first light-emitting unit 511 and the second light-emitting unit A charge generation layer 513 is provided between the knit 512 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in Figure 1(A), respectively. The same thing described in the explanation can be applied. Also, the first light-emitting unit 51 The first and second light-emitting units 512 may have the same configuration or different configurations.

[0152] When a voltage is applied to the anode 501 and cathode 502, the charge generation layer 513 generates a light from one of the light-emitting units. It has the function of injecting electrons into one unit and holes into the other light-emitting unit. That is, Figure In 1(C), when a voltage is applied such that the potential of the anode is higher than the potential of the cathode... In addition, the charge generation layer 513 injects electrons into the first light-emitting unit 511 and the second light-emitting unit Any method that injects a hole into T512 will suffice.

[0153] The charge generation layer 513 is formed with the same configuration as the charge generation layer 116 described in Figure 1(B). Preferably, composite materials of organic compounds and metal oxides have good carrier implantation and carrier transport properties. Due to its superior performance, it can achieve low-voltage and low-current operation. If the anode side of the net is in contact with the charge generation layer 513, the charge generation layer 513 will light up the unit. Since it can also serve as the hole injection layer of the net, the light-emitting unit does not require a hole injection layer. That's fine.

[0154] Furthermore, if an electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer Since layer 119 plays the role of an electron injection layer in the anode-side light-emitting unit, the anode-side light emission The unit does not necessarily need to have an electron injection layer.

[0155] Figure 1(C) illustrates a light-emitting element having two light-emitting units, but there are three or more This method can also be applied to light-emitting devices formed by stacking light-emitting units. Like a light-emitting element in the form of a charge generation layer 513, multiple light-emitting units are placed between a pair of electrodes. By partitioning and arranging the elements, high-brightness light emission is possible while maintaining a low current density, and further This enables the creation of long-life elements. Furthermore, it allows for low-voltage operation and enables the realization of light-emitting devices with low power consumption. It is possible.

[0156] Furthermore, by making the light-emitting color of each light-emitting unit different, the entire light-emitting element... This allows you to obtain light emission of a desired color. For example, a light-emitting element having two light-emitting units In this configuration, the first light-emitting unit produces red and green light, and the second light-emitting unit produces blue light. This makes it possible to obtain a light-emitting element that emits white light as a whole.

[0157] Furthermore, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512 and Each layer, such as the charge generation layer, and the electrodes are, for example, deposited by methods such as vapor deposition (including vacuum deposition) and droplet ejection ( It can be formed using methods such as inkjet printing, coating, and gravure printing. They can be used. Also, they include low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), and Alternatively, it may contain polymer materials.

[0158] (Embodiment 3) This embodiment describes a light-emitting device using the light-emitting element described in Embodiment 2.

[0159] In this embodiment, regarding the light-emitting device fabricated using the light-emitting element described in Embodiment 2: Let's explain using Figure 2. Figure 2(A) is a top view showing the light-emitting device, and Figure 2(B) is a top view of Figure 2. This is a cross-sectional view obtained by cutting (A) at AB and CD. This light-emitting device emits light from a light-emitting element. Controlling these are the drive circuit section (source line drive circuit) 601, indicated by the dotted line, and the pixel section. 602 includes a drive circuit section (gate line drive circuit) 603. Also, 604 is a sealing substrate. 605 is a sealing material, and the area enclosed by the sealing material 605 is a space 607. .

[0160] The routing wire 608 is input to the source line drive circuit 601 and the gate line drive circuit 603. FPC (Flexible Printed Circuit) is a wiring system for transmitting signals and serves as an external input terminal. (Input circuit) 609 receives video signals, clock signals, start signals, reset signals, etc. Receive. Note that only the FPC is shown in the diagram here, but this FPC has a print distribution A wire substrate (PWB) may be attached. The light-emitting device in this specification is a light-emitting device This includes not only the main unit but also the state in which the FPC or PWB is attached to it. ru.

[0161] Next, the cross-sectional structure will be explained using Figure 2(B). The drive circuit section is located on the element substrate 610. And a pixel section is formed, but here, the source line drive circuit 601 which is the drive circuit section and One pixel in the pixel section 602 is shown.

[0162] The element substrate 610 is a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, etc. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fiber) Made using a plastic substrate made of fluoride, polyester, or acrylic resin. Just make it.

[0163] The structure of transistors used in pixels and driving circuits is not particularly limited. For example, inverse staggered It can be a type of transistor or a staggered transistor. Also, top Either a gate-type transistor or a bottom-gate transistor is acceptable. The semiconductor material is not particularly limited, and examples include silicon, germanium, silicon carbide, nitride Gallium can be used, or an In-Ga-Zn metal oxide can be used. An oxide semiconductor containing at least one of the elements, such as zinc, gallium, and zinc, may also be used.

[0164] The crystallinity of semiconductor materials used in transistors is not particularly limited; amorphous semiconductors, Semiconductors with crystalline properties (microcrystalline semiconductors, polycrystalline semiconductors, single-crystal semiconductors, or those with a crystalline region in part) Any semiconductor having the properties of [the semiconductor material] may be used. If a semiconductor having crystalline properties is used, transients may occur. This is preferable because it suppresses the deterioration of the stanic characteristics.

[0165] Here, in addition to the transistors provided in the pixels and driving circuits mentioned above, the touch sensors and the like described later are also included. It is preferable to use oxide semiconductors for semiconductor devices such as transistors. It is particularly preferable to use oxide semiconductors with a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than Ricon, the off state of the transistor can be controlled. The current in this state can be reduced.

[0166] The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). It is also In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is an oxide semiconductor containing an oxide (such as a metal like La, Ce, or Hf). It is preferable.

[0167] In particular, the semiconductor layer has multiple crystalline portions, and the c-axis of the crystalline portion is the surface on which the semiconductor layer is formed. Alternatively, an acid oriented perpendicular to the upper surface of the semiconductor layer and having no grain boundaries between adjacent crystalline regions. It is preferable to use a crystalline semiconductor film.

[0168] By using such materials as semiconductor layers, fluctuations in electrical properties are suppressed, resulting in high reliability. This makes it possible to create a transistor.

[0169] Furthermore, due to its low off-current, the transistor having the aforementioned semiconductor layer can be used to... This makes it possible to retain the charge stored in the capacity over a long period of time. By applying a generator to each pixel, the gradation of the image displayed in each display area is maintained while driving It also becomes possible to shut down the circuit. As a result, it is possible to realize electronic devices with extremely reduced power consumption. It can be expressed.

[0170] It is preferable to provide an undercoat to stabilize the characteristics of the transistor. The undercoat may be: Inorganic silicon oxide films, silicon nitride films, silicon oxide-nitride films, silicon nitride-oxide films, etc. It can be fabricated using an insulating film, either as a single layer or in a multilayer configuration. The underlayer is fabricated by sputtering. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, ALD ( Formed using methods such as Atomic Layer Deposition, coating, and printing. Yes, it is possible. However, a base coat does not need to be applied unless necessary.

[0171] Note that FET623 is one of the transistors formed in the drive circuit section 601. Furthermore, the drive circuit is formed using various CMOS, PMOS, or NMOS circuits. This is sufficient. Furthermore, this embodiment shows a driver-integrated type in which the drive circuit is formed on the substrate. However, this is not always necessary, and the drive circuit can be formed externally rather than on the circuit board. .

[0172] Furthermore, the pixel section 602 includes a switching FET 611 and a current control FET 612 and its drive It is formed by a plurality of pixels, each including a first electrode 613 electrically connected to the rain. However, it is not limited to this, and can also be used as a pixel unit combining three or more FETs and a capacitive element. good.

[0173] Furthermore, an insulator 614 is formed covering the end of the first electrode 613. Here, positive It can be formed by using a photosensitive acrylic resin film of a mold.

[0174] Furthermore, in order to ensure good coverage of the EL layer and other layers formed later, the upper end of the insulator 614 is Alternatively, a curved surface with curvature is formed at the lower end. For example, the material of the insulator 614 and When a positive-type photosensitive acrylic resin is used, the radius of curvature is only at the upper end of the insulator 614. It is preferable to have a curved surface having a thickness of 0.2 μm to 3 μm. Also, the insulating material 614 is used. Therefore, either a negative-type or positive-type photosensitive resin can be used.

[0175] An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. Here, the material used for the first electrode 613 which functions as an anode is a material with a work function of It is desirable to use large materials. For example, ITO film or silicon-containing indigo Indium oxide film, indium oxide film containing 2-20 wt% zinc oxide, titanium nitride film, In addition to monolayer films such as chromium films, tungsten films, zinc films, and Pt films, titanium nitride films and aluminum films are also available. Lamination with a film mainly composed of aluminum, titanium nitride film and aluminum film and titanium nitride A three-layer structure with a film can be used. Furthermore, a laminated structure can be used as a wiring resistor. It has low noise levels, provides good ohmic contact, and can even function as an anode. .

[0176] Furthermore, the EL layer 616 was coated using a vapor deposition method with a vapor deposition mask, an inkjet method, and a spin coating method. It is formed by various methods such as those described in Embodiment 2. The EL layer 616 is formed by the structure described in Embodiment 2. It contains the following: In addition, other materials constituting the EL layer 616 include low molecular weight compounds, This may be a high-molecular-weight compound (including oligomers and dendrimers).

[0177] Furthermore, the material used for the second electrode 617, which is formed on the EL layer 616 and functions as a cathode. Examples include materials with a low work function (Al, Mg, Li, Ca, or alloys and compounds thereof) It is preferable to use materials (MgAg, MgIn, AlLi, etc.). Note that the EL layer 61 If the light generated in 6 passes through the second electrode 617, the second electrode 617 is defined as the film thickness. A thin metal film and a transparent conductive film (ITO, zinc oxide containing 2-20 wt%). Using a lamination process with indium tin oxide containing zinc and silicon (zinc oxide (ZnO), etc.) That would be good.

[0178] Furthermore, 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. The pixel section is a plurality Although light-emitting elements are formed, in the light-emitting device of this embodiment, Embodiment 2 Both the light-emitting element described above and light-emitting elements having other configurations may be mixed together.

[0179] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, A light-emitting element is placed in the space 607 surrounded by the sub-substrate 610, the sealing substrate 604, and the sealing material 605. The structure is equipped with 618. Furthermore, the space 607 is filled with a filler material. In addition to cases where inert gases (such as nitrogen or argon) are used for filling, this also applies when sealing materials are used for filling. Yes, it is. A recess is formed in the sealing substrate, and a desiccant is placed there to suppress deterioration due to moisture. It can be controlled, making it a desirable configuration.

[0180] Furthermore, it is preferable to use epoxy resin or glass frit for the sealing material 605. These materials should ideally be as impermeable to moisture and oxygen as possible. In addition to glass substrates and quartz substrates, other materials can be used for the encapsulating substrate 604, such as FRP (Fiber Reinforced Plastic). reinforced plastics, PVF (polyvinyl fluoride), polyester A plastic substrate made of tel or acrylic resin can be used.

[0181] Although not shown in Figure 2, a protective film may be provided on the second electrode. The protective film is an organic resin film. It can be formed with an inorganic insulating film. Also, the exposed portion of the sealing material 605 can be covered with A protective film may be formed. Furthermore, the protective film may be on the surface and sides of the pair of substrates, a sealing layer, and an insulating layer. It can be installed to cover exposed surfaces such as the margin layer.

[0182] The protective film can be made of a material that is impermeable to impurities such as water. This effectively suppresses the diffusion of impurities such as these from the outside to the inside.

[0183] Materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers can be used, for example, aluminum oxide, hafnium oxide, etc. Phenium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide Titanium dioxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide cerium oxide, scandium oxide, erbium oxide, vanadium oxide, or indi oxide Materials containing um, etc., as well as aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, nitrogen Includes titanium dioxide, 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 oxides Strontium-containing sulfides, erbium and aluminum-containing oxides, and Materials containing oxides, etc., including lium and zirconium can be used.

[0184] The protective film can be formed using a film deposition method that provides good step coverage. This is preferable. One such method is atomic layer deposition (ALD). There is a deposition method. Protecting materials that can be formed using the ALD method. It is preferable to use it for membranes. By using the ALD method, a dense membrane can be created with cracks and pinholes. A protective film can be formed with reduced defects or with a uniform thickness. Also, This reduces the damage inflicted on the processed material when forming a protective film.

[0185] For example, by forming a protective film using the ALD method, surfaces with complex uneven shapes, or taps can be formed. A uniform and low-defect protective film can be formed on the top, sides, and back surfaces of the panel. .

[0186] As described above, a light-emitting device fabricated using the light-emitting element described in Embodiment 2 can be obtained. It is possible.

[0187] Since the light-emitting device in this embodiment uses the light-emitting element described in Embodiment 2, A light-emitting device with desirable characteristics can be obtained. Specifically, the light-emitting device described in Embodiment 2 Because the element has good luminescence efficiency, it is possible to create a light-emitting device with low power consumption.

[0188] Figure 3 shows a light-emitting element that emits white light, with a colored layer (color filter) provided. An example of a light-emitting device that has been made full-color is shown. Figure 3(A) shows the substrate 1001 and the underlying insulation. Film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, first Interlayer insulating film 1020, second interlayer insulating film 1021, peripheral portion 1042, pixel portion 1040, drive Dynamic circuit section 1041, first electrodes 1024W, 1024R, 1024G, 102 4B, partition wall 1025, EL layer 1028, second electrode 1029 of light-emitting element, sealing substrate 103 1. The sealing material 1032 and other components are shown in the diagram.

[0189] Furthermore, Figure 3(A) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue). The colored layer 1034B is provided on a transparent substrate 1033. Also, the black matrix 1 A 035 layer may be further provided. Transparent substrate 1 provided with a colored layer and a black matrix. 033 is aligned and fixed to substrate 1001. Note that the colored layer and black matrix Kus 1035 is covered with an overcoat layer 1036. Also, in Figure 3(A) This consists of a light-emitting layer that allows light to escape to the outside without passing through the colored layers, and a layer that allows light to escape to the outside by passing through the colored layers of each color. There is a light-emitting layer, and light that does not pass through the colored layer is white, while light that passes through the colored layer is red, green, and blue. Therefore, images can be represented using four colored pixels.

[0190] Figure 3(B) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer Example of forming layer 1034B) between the gate insulating film 1003 and the first interlayer insulating film 1020. This was shown. Thus, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. That's good too.

[0191] Furthermore, in the light-emitting device described above, light is taken to the substrate 1001 side on which the FET is formed. Although a light-emitting device with a bottom-emission structure was used, the light emission was taken from the sealing substrate 1031 side. It can also be used as a light-emitting device with a projection structure (top emission type). A cross-sectional view of the light-emitting device is shown in Figure 4. In this case, the substrate 1001 is a substrate that does not transmit light. This can be done. Until the connecting electrode that connects the FET and the anode of the light-emitting element is fabricated, the bottom edge It is formed in the same way as a mission-type light-emitting device. Then, the third interlayer insulating film 1037 is attached to electrode 1 It is formed by covering 022. This insulating film may also play a planar role. Third interlayer insulating The border film 1037 can be formed using the same material as the second interlayer insulating film, as well as other known materials. It is possible.

[0192] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are the anodes here. However, it can also be a cathode. Also, a top-emission type light-emitting device as shown in Figure 4. In this case, it is preferable that the first electrode be a reflective electrode. The configuration of the EL layer 1028 is as follows: The configuration is as described in Embodiment 2 as the EL layer 103, and the white light emission is The device structure will be such that it can be obtained.

[0193] In the top emission structure shown in Figure 4, the colored layer (red colored layer 1034R, green colored layer) The sealing is performed using a sealing substrate 1031 having a color layer 1034G and a blue colored layer 1034B. This can be done. The encapsulation substrate 1031 has a black matrix positioned between the pixels. 1035 may be provided. Colored layer (red colored layer 1034R, green colored layer 1034G, The blue colored layer (1034B) and the black matrix are covered by an overcoat layer. It is acceptable to leave it there. Furthermore, the sealing substrate 1031 shall be a light-transmitting substrate. Here, we have shown an example of full-color display using four colors: red, green, blue, and white, but it is not particularly limited to red, Full-color display may be performed using four colors: yellow, green, and blue, or three colors: red, green, and blue.

[0194] In top-emission type light-emitting devices, a microcavity structure can be suitably applied. A light-emitting element having a microcavity structure has a first electrode as a reflective electrode and a second electrode as a semipermeable electrode. This is obtained by using hyper- and semi-reflective electrodes. There is a small gap between the reflective electrode and the semi-transparent / semi-reflective electrode. It has at least an EL layer and at least an emissive layer that forms an emissive region.

[0195] The reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%. It is %, and its resistivity is 1 × 10⁻⁶. -2 Assume the membrane is less than Ωcm in diameter. Also, semipermeable... The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1 × 10 -2 Assume the membrane is less than Ωcm in diameter.

[0196] The light emitted from the light-emitting layer contained in the EL layer is reflected by the reflective electrode and the semi-transmitting / semi-reflective electrode. It is reflected and resonates.

[0197] The light-emitting element can change the thickness of the transparent conductive film, the aforementioned composite material, the carrier transport material, etc. This allows us to change the optical distance between the reflective electrode and the semitransmissive / semi-reflective electrode. Between the reflective electrode and the semitransmissive / semi-reflective electrode, the light of the resonant wavelength is amplified, and the resonance is prevented. It can attenuate light of a specific wavelength.

[0198] Furthermore, the light reflected back by the reflective electrode (the first reflected light) is semi-transmitted from the light-emitting layer. • Because it causes significant interference with the light (first incident light) that directly enters the semi-reflecting electrode, the reflective electrode and The optical distance of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is amplified). It is preferable to adjust the wavelength of the emitted light. By adjusting the optical distance, the first By aligning the phase of the reflected light and the first incident light, the light emitted from the light-emitting layer can be further amplified. ru.

[0199] Furthermore, even if the EL layer in the above configuration has a structure with multiple light-emitting layers, it may still be a single light-emitting layer The structure may also have the above-described tandem light-emitting element configuration, for example, in combination with the above-described tandem light-emitting element configuration. Multiple EL layers are provided in a single light-emitting element, with a charge generation layer in between, and each EL layer also has a single charge generation layer. Alternatively, it may be applied to a configuration that forms multiple light-emitting layers.

[0200] Having a microcavity structure enhances the emission intensity in the front direction at specific wavelengths. This makes it possible to reduce power consumption. Furthermore, the four sub-colors red, yellow, green, and blue are used. In the case of a light-emitting device that displays images as is, in addition to the brightness enhancement effect of yellow light emission, all sub-pixels By applying a microcavity structure tailored to the wavelength of each color, a light-emitting device with excellent characteristics can be produced. It can be placed there.

[0201] Since the light-emitting device in this embodiment uses the light-emitting element described in Embodiment 2, A light-emitting device with desirable characteristics can be obtained. Specifically, the light-emitting device described in Embodiment 2 Because the element has good luminescence efficiency, it is possible to create a light-emitting device with low power consumption.

[0202] Up to this point, we have explained active-matrix light-emitting devices, but from here on we will discuss passive devices. A matrix-type light-emitting device will be described. Figure 5 shows a passive light-emitting device fabricated by applying the present invention. This shows a matrix-type light-emitting device. Note that Figure 5(A) is a perspective view showing the light-emitting device, Figure 5( B) is a cross-sectional view obtained by cutting Figure 5(A) along the XY line. In Figure 5, on the substrate 951, An EL layer 955 is provided between electrode 952 and electrode 956. The end of electrode 952 is an insulating layer. It is covered with an edge layer 953. A partition layer 954 is provided on top of the insulating layer 953. The side walls of the partition layer 954, as they approach the substrate surface, the distance between one side wall and the other side wall It has a slope that narrows as it goes. In other words, the cross-section of the partition layer 954 in the short-side direction is trapezoidal. It is shaped such that the bottom edge (which faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) The upper edge (the edge that faces the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953) is better. It is also shorter. In this way, by providing the partition layer 954, the light-emitting element is affected by static electricity, etc. This can prevent deterioration. Also, in the case of a passive matrix type light-emitting device, The light-emitting element described in 2 is used, and the light-emitting device is highly reliable or has low power consumption. It can be used as a device.

[0203] The light-emitting device described above uses a number of tiny light-emitting elements arranged in a matrix. Because it can be controlled, it is suitable for use as a display device for displaying images. It is a device.

[0204] Furthermore, this embodiment can be freely combined with other embodiments.

[0205] (Embodiment 4) In this embodiment, an example of using the light-emitting element described in Embodiment 2 as an illumination device is shown in Figure 6. I will explain while illuminating. Figure 6(B) is a top view of the lighting device, and Figure 6(A) is the same as in Figure 6(B). This is a cross-sectional view of ef.

[0206] The lighting device in this embodiment has a light-transmitting substrate 400 which is a support, and a first An electrode 401 is formed. The first electrode 401 is the first electrode 10 in Embodiment 2. This corresponds to 1. When light is extracted from the first electrode 401 side, the first electrode 401 is light-transmitting. It is formed from a material having [a certain characteristic].

[0207] A pad 412 for supplying 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 in Embodiment 2. The configuration of the EL layer 103 in the light-emitting units 511, 512 and the charge generation layer 513 This corresponds to a combined configuration, etc. Please refer to the relevant description for details on these configurations.

[0209] The EL layer 403 is covered to form the second electrode 404. The second electrode 404 is in Embodiment 2. This corresponds to the second electrode 102. When light emission is taken from the first electrode 401 side, the second The electrode 404 is formed of a highly reflective material. The second electrode 404 is pad 412 Voltage is supplied by connecting it to it.

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

[0211] A substrate 400 on which a light-emitting element having the above configuration is formed, and a sealing substrate 407 are sealed together with a sealing material 4 The lighting device is completed by fixing and sealing it using 05 and 406. Sealing material 40 5. Either 406 or 406 is acceptable. Also, the inner sealant 406 (Figure 6(B) A desiccant can also be mixed in (not shown), which allows it to absorb moisture. This will lead to improved reliability.

[0212] Furthermore, the pad 412 and a portion of the first electrode 401 are extended outside the sealing materials 405 and 406. By providing it, it can be used as an external input terminal. Also, a converter can be placed on top of it. An IC chip 420 or similar, which incorporates such features, 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. This allows for the creation of a light-emitting device with low power consumption.

[0214] (Embodiment 5) In this embodiment, an example of an electronic device that includes the light-emitting element described in Embodiment 2 as a part thereof... Let me explain. The light-emitting element described in Embodiment 2 has good luminous efficiency and low power consumption. It is a light-emitting element. As a result, the electronic device described in this embodiment has a light-emitting part with low power consumption. It is possible to create an electronic device that has [this feature].

[0215] Examples of electronic devices to which the above light-emitting element is applied include television equipment (television, or television). (also called a revision receiver), monitors for computers, digital cameras, digital Video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices) ), portable game consoles, personal digital assistants, sound playback devices, large game machines such as pachinko machines, etc. These include [examples of electronic devices]. Specific examples of these electronic devices are shown below.

[0216] Figure 7(A) shows an example of a television system. The television system is housed in a 710 enclosure. The display unit 7103 is incorporated into part 1. Also, the housing is connected by the stand 7105. This shows the configuration supporting 7101. The display unit 7103 can display video. The display unit 7103 is capable of arranging the light-emitting elements described in Embodiment 2 in a matrix. It is composed of.

[0217] The television equipment can be operated using the control switches on the housing 7101 or a separate remote control. This can be done using the device 7110. The remote control device 7110 has an operation key 7109. This allows you to control the channel and volume, and the video displayed on the display unit 7103 It can be operated. Also, the remote control unit 7110 A display unit 7107 that displays the information output from the unit may also be provided.

[0218] The television system shall consist of a receiver, modem, etc. It can receive television broadcasts, and also communicate via wired or wireless connection through a modem. By connecting to a network, one-way (sender to receiver) or two-way (sender to receiver) communication is possible. It is also possible to communicate information between recipients, or between recipients themselves.

[0219] Figure 7(B1) is a computer, consisting of the main unit 7201, the casing 7202, the display unit 7203, and a key - Includes board 7204, external connection port 7205, pointing device 7206, etc. Furthermore, this computer arranges the light-emitting elements described in Embodiment 2 in a matrix. It is manufactured by using it in the display unit 7203. The computer in Figure 7(B1) is in Figure 7( It may also be in a form like B2). The computer in Figure 7(B2) has 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, and the information displayed on the second display unit 7210 is Input can be performed by operating the displayed input screen with a finger or a special pen. Furthermore, the second display unit 7210 can display not only input information but also other images. The display unit 7203 may also be a touch panel. The two screens are connected by a hinge. This can lead to problems such as scratching or damaging the screen during storage or transport. This can also prevent the occurrence of negativity.

[0220] Figure 7(C) shows a mobile phone, which is an example of a portable terminal. The mobile phone has a housing 74 In addition to the display unit 7402 incorporated into 01, there are also operation buttons 7403 and an external connection port 7404. It is equipped with speaker 7405, microphone 7406, etc. Note that the mobile phone is in its actual form. The display unit 7402 is made by arranging the light-emitting elements described in state 2 in a matrix. .

[0221] The mobile terminal shown in Figure 7(C) allows users to input information by touching the display unit 7402 with their fingers or other objects. It can also be configured to allow for making phone calls or composing emails. Operations such as this can be performed by touching the display unit 7402 with a finger or the like.

[0222] The display unit 7402 has three main modes. The first is a display that primarily displays images. The first mode is display mode, the second is input mode which is mainly for inputting information such as characters. The third is display mode. This is a display + input mode, which is a combination of two modes: display mode and input mode.

[0223] For example, when making a phone call or composing an email, the display unit 7402 is used for text input. In this case, the primary text input mode should be used, and you should perform the input operation for the characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402. It seems so.

[0224] Furthermore, the mobile device has sensors inside that detect tilt, such as a gyroscope and an accelerometer. By installing the device, the orientation of the mobile terminal (portrait or landscape) is determined, and the screen display of the display unit 7402 is displayed accordingly. The display can be set to switch automatically.

[0225] Furthermore, screen modes can be switched by touching the display unit 7402 or by operating the housing 7401. This is done by operating button 7403. Also, the type of image displayed on display unit 7402 Therefore, it is also possible to switch between them. For example, the image signal displayed on the display unit is a video signal. Switch to display mode if it's data, or to input mode if it's text data.

[0226] Furthermore, in input mode, the signal detected by the optical sensor of the display unit 7402 is detected and displayed If there is no input via touch operation on unit 7402 for a certain period of time, the screen mode will be changed to input mode. You may also control the system to switch from that display mode to a different mode.

[0227] The display unit 7402 can also function as an image sensor. For example, the display unit 74 By touching device 02 with the palm or fingers, the user can be authenticated by capturing images of their palm print, fingerprints, etc. Furthermore, the display unit may have a backlight that emits near-infrared light or a sensing light that emits near-infrared light. Using the appropriate source, it is also possible to image finger veins, palmar veins, and other veins.

[0228] The configuration shown in this embodiment is a combination of the configurations shown in Embodiments 1 to 4 as appropriate. They can be used together.

[0229] As described above, the scope of application of the light-emitting device equipped with the light-emitting element described in Embodiment 2 is extremely broad. This light-emitting device can be applied to electronic devices in all fields. (Described in Embodiment 2) By using light-emitting elements, it is possible to obtain electronic devices with low power consumption.

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

[0231] The cleaning robot 5100 has a display 5101 located on the top and multiple displays located on the sides. It has several cameras 5102, brushes 5103, and operation buttons 5104. However, the underside of the 5100 cleaning robot is equipped with wheels, a suction port, etc. The 5100 robot also includes an infrared sensor, ultrasonic sensor, acceleration sensor, and piezo sensor. It is equipped with various sensors such as optical sensors and gyro sensors. Also, the cleaning robot 5 Unit 100 is equipped with wireless communication means.

[0232] The cleaning robot 5100 moves autonomously, detects the dirt 5120, and uses the suction port located on its underside to... It can then vacuum up the dust.

[0233] Furthermore, the cleaning robot 5100 analyzes images captured by the camera 5102, and detects walls, furniture, or It can determine the presence or absence of obstacles such as steps. Furthermore, image analysis can detect wiring and other obstacles. If an object that may become entangled in brush 5103 is detected, the rotation of brush 5103 will be stopped. can.

[0234] The display 5101 displays information such as the battery level and the amount of dust collected. This is possible. The path taken by the cleaning robot 5100 can be displayed on the display 5101. Good. Also, the display 5101 is a touch panel, and the operation buttons 5104 are on the display. It may also be provided at Ray 5101.

[0235] The cleaning robot 5100 can communicate with portable electronic devices 5140 such as smartphones. Yes, it is possible. Images captured by camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the 5100 cleaning robot can know what's happening in the room even when they're away from home. It is possible to display the information on the display 5101 on portable electronic devices such as smartphones. You can also check it there.

[0236] A light-emitting device according to one aspect of the present invention can be used in a display 5101.

[0237] The robot 2100 shown in Figure 8(B) consists of a computing unit 2110, an illuminance sensor 2101, and a microphone. Lophone 2102, upper camera 2103, speaker 2104, display 2105, bottom It is equipped with a camera 2106, an obstacle sensor 2107, and a moving mechanism 2108.

[0238] Microphone 2102 has the function of detecting the user's voice and ambient sounds, etc. Speaker 2104 has the function of emitting sound. Robot 2100 has a microphone Using the 2102 and speaker 2104, communication with the user is possible. It is possible.

[0239] The display 2105 has the function of displaying various information. The robot 2100 is The user can display the desired information on the display 2105. The 2105 may have a touch panel. Also, the display 2105 is removable. It can be any information terminal capable of charging, and by installing it in a fixed position on the robot 2100, And it enables the transfer of data.

[0240] The upper camera 2103 and lower camera 2106 are used to image the area around the robot 2100. It has the ability to detect obstacles. Furthermore, the obstacle sensor 2107 uses the moving mechanism 2108 to detect robot 210 Robot 21 can detect the presence or absence of obstacles in the direction of travel as it moves forward. 00 uses the upper camera 2103, the lower camera 2106 and the obstacle sensor 2107 The light-emitting device according to one aspect of the present invention can recognize its surroundings and move safely. It can be used in display 2105.

[0241] Figure 8(C) shows an example of a goggle-type display. For example, the housing 5000, the display unit 5001, the speaker 5003, the LED lamp 5004, Connection terminal 5006, sensor 5007 (force, displacement, position, velocity, acceleration, angular velocity, rotational speed, Distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, electric current, voltage, power, radiation (including functions for measuring radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), It includes a crossphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, and the like.

[0242] The light-emitting device according to one aspect of the present invention can be used in the display unit 5001 and the display unit 5002. .

[0243] Figure 9 shows an example in which the light-emitting element described in Embodiment 2 is used in a desk lamp, which is a lighting device. The desk lamp shown in Figure 9 has a housing 2001 and a light source 2002, and the light source 2002 and Alternatively, the lighting device described in Embodiment 4 may be used.

[0244] Figure 10 shows an example in which the light-emitting element described in Embodiment 2 is used as an indoor lighting device 3001. Yes. The light-emitting element described in Embodiment 2 is a light-emitting element with high luminous efficiency, therefore the power consumption is It can be made into a small lighting device. Also, the light-emitting element described in Embodiment 2 can be made to have a large area. Because this is possible, it can be used as a large-area lighting device. Also, as described in Embodiment 2 Because the light-emitting element is thin, it can be used in a miniaturized lighting device.

[0245] The light-emitting element described in Embodiment 2 can also be mounted on the windshield or dashboard of an automobile. This can be done. Figure 11 shows the light-emitting element described in Embodiment 2 on the windshield of an automobile or a dash One embodiment for use on a dashboard is shown. Display areas 5200 to 5203 are shown in the embodiment. This is a display provided using the light-emitting element described in Form 2.

[0246] Display area 5200 and display area 5201 are in an embodiment provided on the windshield of an automobile. This is a display device equipped with the light-emitting element described in 2. The light-emitting element described in Embodiment 2 is the first By fabricating the first electrode and the second electrode with translucent electrodes, the opposite side can be seen through. It can be used as a display device in a so-called see-through state. Therefore, even if it is installed on the windshield of a car, it can be installed without obstructing the view. This is possible. Furthermore, if transistors or other components for driving are provided, organic semiconductor materials may be used. Translucent transistors such as organic transistors and transistors using oxide semiconductors Using a Rangista would be a good idea.

[0247] Display area 5202 is a display equipped with the light-emitting element described in Embodiment 2, which is provided on the pillar portion. This is a display device. The display area 5202 displays images from an imaging device installed on the vehicle body. This allows for the correction of the view obstructed by the pillar. Similarly, the dash The display area 5203 on the board section provides a view of the outside of the car that is obstructed by the vehicle body. By displaying images from imaging devices installed in the area, blind spots are compensated for, and safety is enhanced. It is possible to project images in a way that complements the unseen parts, making the unnaturalness more natural. Safety checks can be performed without any sense of touch.

[0248] Display area 5203 also displays navigation information, speedometer, tachometer, odometer, fuel gauge, and gear. By displaying the status, air conditioner settings, and other information, various types of 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 display areas 5200 to 5202. Display areas 5200 to 5203 can also be used as lighting devices.

[0249] Figures 12(A) and (B) also show a foldable portable information terminal 5150. The portable information terminal 5150 consists of a housing 5151, a display area 5152, and a bendable portion 515 It has 3. Figure 12(A) shows the portable information terminal 5150 in its unfolded state. Figure 12( B) shows the portable information terminal in its folded state. The portable information terminal 5150 has a large display area Despite having a 5152mm field of view, it folds up compactly and is highly portable.

[0250] The display area 5152 can be folded in half by the bending portion 5153. Bending portion 515 3 consists of an expandable member and multiple support members, and when folded, the expandable The member stretches, and the bent portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more. It folds up.

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

[0252] Figures 13(A) to (C) also show a foldable portable information terminal 9310. Figure 13 (A) shows the portable information terminal 9310 in its unfolded state. Figure 13(B) shows the unfolded state or This shows the portable information terminal 9310 in an intermediate state, transitioning from one folded state to the other. Figure 13(C) shows the folded state of the personal digital assistant 9310. Personal digital assistant 9310 It offers excellent portability when folded and a seamless, wide display area when unfolded. This provides excellent readability in 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). It may also be an input / output device. In addition, the display panel 9311 is connected via the hinge 9313. By bending the two housings 9315, the mobile information terminal 9310 is unfolded. It can be reversibly transformed from a folded state. A light-emitting device according to one aspect of the present invention It can be used with the display panel 9311. [Examples]

[0254] <<Synthesis Example 1>> In this example, an organic compound, 4,4'-(1,1-cyclohexane), which is one aspect of the present invention, is used. -diyl)bis[N,N-bis(4-cyclohexylbenzene-1-yl)aminobenzene This explains the synthesis method of [n] (abbreviated as TAPC-02). Note that the composition of TAPC-02 The construction is shown below.

[0255] [ka]

[0256] <Step 1: 4,4'-(1,1-cyclohexane-diyl)bis[N,N-bis(4 Synthesis of [-cyclohexylbenzene-1-yl)aminobenzene] 5.3g (20mm) of 1,1-bis(4-aminophenyl)cyclohexane in a three-necked flask. ol), 4-cyclohexyl-1-bromobenzene 21.0g (88 mmol), sodium Um tert-butoxide 25.4g (264 mmol), xylene mixture 400mL After adding the mixture and degassing it under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred until it reached this point. Here, allyl palladium chloride dimer(II) (abbreviated as (Allyl PdCl)2) 293 mg (0.8 mmol), di-tert-butyl(1-methyl-2) ,2-diphenylcyclopropyl)phosphine (trade name: cBRIDP(registered trademark))1 128 mg (3.2 mmol) was added, and this mixture was heated under reflux for 6 hours. Then, Return the flask temperature to approximately 60°C, add approximately 4 mL of water, filter off the precipitated solid, and remove it with toluene. The filtrate was washed. The filtrate was concentrated, and the resulting xylene solution was subjected to silica gel column chromatography. - It was purified. The resulting solution was concentrated to obtain a concentrated toluene solution. The solution was added dropwise to ethanol and reprecipitation occurred. The precipitate was filtered at approximately 0°C, and the resulting solid was heated to approximately 75°C. The product was dried under reduced pressure to obtain 16.5 g of the target white solid in a yield of 92%. The synthesis scheme for P1 is shown below.

[0257] [ka]

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

[0259] 1 H-NMR.δ(CDCl3):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 sublimation using the train sublimation method. The manufacturing process was performed under conditions of a pressure of 3.0 Pa and an argon flow rate of 12.3 mL / min at 355°C. The process was carried out by heating. After sublimation purification, 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 a toluene solution and a solid thin film were obtained. The absorption spectrum was measured. The solid thin film was fabricated on a quartz substrate using vacuum deposition. This includes an ultraviolet-visible spectrophotometer (Solution: JASCO Corporation, V-550; Thin film: Hitachi, Ltd.) A U-4100 (manufactured by High Technologies) was used. The absorption spectrum of the solution was obtained using a quartz crystal. The absorption spectrum of the thin film was calculated by subtracting the absorption spectrum measured with only toluene added to the solution. The absorbance (-log) was determined from the transmittance and reflectance including the substrate. 10 [%T / (1 Calculated from (00-%R). Note that %T represents transmittance and %R represents reflectance. Also, the emission spectrum A fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the ketol.

[0262] Figure 15 shows the measurement results of the absorption and emission spectra of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Also, the absorption spectrum of a solid thin film is shown. The measurement results of the emission spectrum are shown in Figure 16.

[0263] Next, the organic compound, TAPC-02, was subjected to liquid chromatography-mass spectrometry (Liquid Ch). Mass spectrometry (LC / MS) Mass (MS) analysis was performed using [analysis method].

[0264] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C4 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. The pull was prepared by dissolving TAPC-02 of any concentration in toluene and diluting it with acetonitrile. The injection volume was set at 5.0 μL.

[0265] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0266] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the m / z=899 component is ionized in the collision cell using argon gas. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 70 eV. The mass range measured was m / z (mass charge). The ratio was set to 100 to 1000. Figure 17 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0267] From the results in Figure 17, TAPC-02 primarily produces product ions around m / z = 899. It was found that [specific substance] was detected. Furthermore, the results shown in Figure 17 are specific to TAPC-02. Since it shows characteristic results, it is useful for identifying TAPC-02 contained in the mixture. This can be considered important data.

[0268] The flag for m / z=566 was observed when measured at a collision energy of 70eV. The ment ion is generated when the CN bond of TAPC-02 is cleaved, resulting in 4,4'-(1, 1-Cyclohexane-diyl)[N-bis(4-cyclohexylbenzene-1-yl) Minobenzene [N'-(4-cyclohexylbenzene-1-yl)aminobenzene] and This is presumed to be one of the features of TAPC-02.

[0269] The refractive index of the synthesized TAPC-02 and 1, an organic compound known to have a low refractive index. 1-Bis-(4-bis(4-methylphenyl)-aminophenyl)-cyclohexane Figure 38 shows the refractive indices of (abbreviated as TAPC) and . Note that the refractive index n is the refractive index of ordinary light. n Ordinary and n Extra-ordinary, which are the refractive indices of the extraordinary rays. There is y and the mean n, which is the average of the two. In this specification, it is simply referred to as "refractive index". If anisotropy analysis is not performed, the n average will be used, and the n Ordinary You can substitute y. Also, the value of n Ordinary is doubled, and n Ext The n average is the sum of the ra-ordinary values ​​divided by 3.

[0270] As shown in Figure 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-level organic compound.

[0271] Next, regarding the glass transition temperature (Tg) of TAPC-02 and TAPC, differential scanning heat is used. The measurement was performed using an analytical instrument (DSC). The measurement results showed that the Tg of TAPC-02 was 119°C, TAP The Tg of C was 85°C. Therefore, TAPC-02 exhibits good heat resistance. I found out. [Examples]

[0272] ≪Synthesis Example 2≫ In this example, an organic compound, 4,4'-(1,1-cyclohexane), which is one aspect of the present invention, is used. -diyl)bis{N-(4-cyclohexylphenyl)N-[(4'-cyclohexyl) Synthesis of -1,1'-biphenyl-4-yl]aminobenzene (abbreviation: TAPC-03) The method will be explained below. The structure of TAPC-03 is shown below.

[0273] [ka]

[0274] <Step 1: 4,4'-(1,1-cyclohexane-diyl)bis{N-(4-cyclo Synthesis of hexylphenyl (aminobenzene) 5.3g (20mm) of 1,1-bis(4-aminophenyl)cyclohexane in a three-necked flask. ol), 4-cyclohexyl-1-bromobenzene 10.0g (42 mmol), sodium Um tert-butoxide 12.1g (126 mmol), xylene mixture 200mL After adding the mixture and degassing it under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred until it reached this point. Here, allyl palladium chloride dimer(II) (abbreviated as (Allyl PdCl)2) 150 mg (0.4 mmol), dicyclohexyl (2',6'-dimeth Xy-{1,1'-biphenyl}-2-yl)phosphine (abbreviation: SPhos) 660ml g (1.6 mmol) was added, and this mixture was heated under reflux for 6 hours. Then, the flask... Return the temperature to approximately 60°C, add approximately 2 mL of water, filter off the precipitated solid, and wash with toluene. The filtrate was concentrated, and the resulting xylene solution was purified by silica gel column chromatography. The obtained solution was concentrated to obtain a concentrated toluene solution. This toluene solution was then converted to an ethanol solution. The solution was added dropwise and re-precipitation occurred. The precipitate was filtered at approximately 0°C, and the resulting solid was dried under reduced pressure at approximately 75°C. The mixture was dried to obtain 9.5 g of the target white solid in a yield of 81%. Step 1 Synthetic Ski The following is an example of the term "Mu".

[0275] [ka]

[0276] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 1 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The H-NMR chart is shown in Figure 18. In step 1, the organic compound, 4,4'-(1,1-cyclohexane-diyl)bis{N It was found that {(4-cyclohexylphenyl)aminobenzene} could be synthesized.

[0277] 1 H-NMR.δ(CDCl3):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-cyclohexane-diyl)bis{N-(4-cyclo Hexylphenyl)N-[(4'-cyclohexyl)-1,1'-biphenyl-4-yl Synthesis of aminobenzene (abbreviation: TAPC-03) In a three-necked flask, add 4,4'-(1,1-cyclohexane-diyl)bis{N-(4-cyclo Hexylphenyl (aminobenzene) 5.8g (10 mmol), 4'-cyclohexyl -(1,1'-biphenyl)-4-chlorobenzene 5.4g (20 mmol), sodium Add 5.8g (60mmol) of tert-butoxide and 70mL of xylene mixture. After degassing under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. Stirring was performed. Here, allyl palladium chloride dimer(II) (abbreviation: (AllylPdCl) )2) 73 mg (0.2 mmol), di-tert-butyl (1-methyl-2,2-diph Phenylcyclopropyl(phosphop)phosphine (abbreviation: cBRIDP) 280 mg (0.8 mmol) ) was added, and the mixture was heated under reflux for 8 hours. After that, the temperature of the flask was reduced to approximately 60°C. Return the sample to the container, add approximately 2 mL of water, filter off the precipitated solid, and wash with toluene. The filtrate was concentrated, The obtained xylene solution was purified by silica gel column chromatography. The solution was concentrated to obtain a concentrated toluene solution. This toluene solution was added dropwise to ethanol and reprecipitation occurred. The precipitate was filtered at approximately 0°C, and the resulting solid was dried under reduced pressure at approximately 75°C to obtain the target product. A white solid of 5.8 g was obtained with a yield of approximately 100%. The synthesis scheme for Step 2 is as follows: This will be shown.

[0279] [ka]

[0280] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The H-NMR chart is shown in Figure 19. In step 2, the organic compound, 4,4'-(1,1-cyclohexane-diyl)bis{N -(4-cyclohexylphenyl)N-[(4'-cyclohexyl)-1,1'-bife It was found that 'ny-4-yl]aminobenzene' (abbreviated as TAPC-03) could be synthesized. Ta.

[0281] 1 H-NMR.δ(CDCl3):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 embodiment, an element-emitting element 1 and a comparative element-emitting element 1 according to one aspect of the present invention will be described. The structural formulas of the organic compounds used in element 1 and comparative light-emitting element 1 are shown below.

[0283] [ka]

[0284] (Method for fabricating light-emitting element 1) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. The first electrode 101 was formed by depositing a film using the 3D method. The film thickness was set to 70 nm, and the electrode surface The product was set to 2mm x 2mm.

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

[0286] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0287] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, By deposition using resistance heating, the 4,4'-bis(9-carba) represented by the above structural formula (i) is obtained. Zol)-2,2'-dimethyl-biphenyl (abbreviation: dmCBP) and molybdenum oxide (V I) Co-deposit 10 nm of the two materials in a weight ratio of 2:0.5 (=dmCBP:MoOx). Then, a hole injection layer 111 was formed.

[0288] Next, on the hole injection layer 111, the 4,4'-(1,1-cyan represented by the above structural formula (ii) is injected. (4-cyclohexylbenzene-1-yl)a After depositing minobenzene (abbreviation: TAPC-02) to a film thickness of 65 nm, the above The structural formula (iii) represents N-(1,1'-biphenyl-4-yl)-9,9-dimethyl Lu-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9H-F Luoren-2-amine (abbreviated as PCBBiF) is deposited to a thickness of 5 nm to create hole channels. A deposition layer 112 was formed.

[0289] Next, the 2-[3'-(dibenzothiophen-4-yl) represented by the above structural formula (iv) Biphenyl-3-yl[f,h]quinoxaline (abbreviation: 2mDBTBPDBq) -II), PCBBiF, and (acetylacetonato)bis represented by the above structural formula (v). (4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)] 2(acac)]) and in weight ratio 0.7:0.3:0.06 (=2mDBTBPDBq -II:PCBBiF:[Ir(dppm)2(acac)]) so that 20nm together After deposition, 0.8:0.2:0.06 (=2mDBTBPDBq-II:PCBBiF :[Ir(dppm)2(acac)]) is co-deposited at 20 nm to create the light-emitting layer 113 It formed.

[0290] Subsequently, 2mDBTBPDBq-II was vapor-deposited onto the light-emitting layer 113 to a thickness of 10 nm. After application, bathophenanthroline (abbreviation: BPhen), represented by the above structural formula (vi), An electron transport layer 114 was formed by depositing a film thickness of 5 nm.

[0291] After forming the electron transport layer 114, lithium fluoride (LiF) and BPhen are added in a volume ratio. To achieve a ratio of 0.75:0.25 (=LiF:BPhen), a 35nm co-deposit was performed, followed by electron injection. An underlayer 115 is formed, followed by the deposition of aluminum to a film thickness of 200 nm. The second electrode 102 was then formed to create the light-emitting element 1 of this embodiment.

[0292] (Method for fabricating comparative light-emitting element 1) The comparative light-emitting element 1 has a layer formed with TAPC-02 in the hole transport layer 112 of the light-emitting element 1. , represented by the above structural formula (vii) 1,1-bis-(4-bis(4-methylphenyl) (-amino-phenyl)-cyclohexane (abbreviation: TAPC) was used, and the film thickness was set to 70 nm. The other components were fabricated in the same manner as light-emitting element 1.

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

[0294] [Table 1]

[0295] The light-emitting element 1 and the comparative light-emitting element 1 are placed in a glove box under a nitrogen atmosphere, and the light-emitting element The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealing material around the element). After clothing, UV treatment during sealing, and heat treatment at 80°C for 1 hour, these light-emitting elements undergo initial processing. The characteristics were measured. Furthermore, the glass substrate on which the light-emitting element was fabricated was treated to improve extraction efficiency. No special measures have been taken for this purpose.

[0296] Figure 20 shows the luminance-current density characteristics of light-emitting element 1 and comparison light-emitting element 1, and the current efficiency-luminance characteristics. Figure 21 shows the luminance-voltage characteristics, Figure 22 shows the current-voltage characteristics, and Figure 23 shows the external quantum efficiency-luminance. The intensity characteristics are shown in Figure 24, and the emission spectra are shown in Figure 25. Furthermore, the 1000 cd / m³ values ​​for each light-emitting element are shown in Figure 25. m 2Table 2 shows the main characteristics of the vicinity. Note that color was used for measuring luminance and CIE chromaticity. A luminance meter (Topcon BM-5A) was used, and a multi-channel luminance meter was used to measure the emission spectrum. A spectrometer (Hamamatsu Photonics, PMA-11) was used. As shown in Figure 25, the light-emitting element 1 and the light-emitting element are compared. The emission spectra of comparison light-emitting element 1 overlap very well, and comparison light-emitting element 1 It can be seen that the optical distance, which is the product of the film thickness and refractive index, is almost the same. It can be said that a strict comparison between comparison light-emitting element 1 and light-emitting element 1 is possible. Note that in Figure 24 above... The external quantum efficiency shown is the value assuming a Lambertsian, as shown in the table below. External quantum efficiency measures the angular dependence of the emission spectrum and the difference from the Lambertsian distribution. The true value, after correction, is used.

[0297] [Table 2]

[0298] As shown in Figures 20 to 25 and Table 2, a light-emitting element 1, which is one embodiment of the present invention, has a hole transport layer that refracts A layer consisting of TAPC-02, an organic compound according to one embodiment of the present invention, which has a lower folding ratio than TAPC. It was found that by having this feature, it was possible to create a light-emitting element with good luminescence efficiency. [Examples]

[0299] In this embodiment, an element-emitting element 2 according to one aspect of the present invention will be described. The organic material used in the element-emitting element 2 The structural formula of the compound is shown below.

[0300] [ka]

[0301] (Method for fabricating light-emitting element 2) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. The first electrode 101 was formed by depositing a film using the 3D method. The film thickness was set to 70 nm, and the electrode surface The product was set to 2mm x 2mm.

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

[0303] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0304] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, By deposition using resistance heating, the above structural formula (ii) represents 4,4'-(1,1-cyanthide (4-cyclohexylbenzene-1-yl)a Minobenzene (abbreviation: TAPC-02) and molybdenum(VI) oxide in a weight ratio of 2:0 After co-depositing 50 nm to achieve a .5 (=TAPC-02: molybdenum oxide) structure, the above structure The 4,4'-bis(9-carbazole)-2,2'-dimethyl-bifu represented by formula (i) dmCBP (abbreviation: dmCBP) and molybdenum(VI) oxide are mixed in a weight ratio of 2:0.5 (=d A hole injection layer 111 was formed by co-depositing 5 nm of material (mCBP:MoOx) to create a hole injection layer.

[0305] Next, on the hole injection layer 111, 4-phenyl-4'- represented by the above structural formula (viii) is injected. (9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) 2 A hole transport layer 112 was formed by depositing 0 nm of material.

[0306] Next, the 2-[3'-(dibenzothiophen-4-yl) represented by the above structural formula (iv) Biphenyl-3-yl[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-carbazole-3-yl)phenyl [nyl]-9H-fluorene-2-amine (abbreviation: PCBBiF) and the above structural formula (v) Represented as (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium III) (abbreviation: [Ir(dppm)2(acac)]) and by weight ratio 0.7:0.3 :0.06(=2mDBTBPDBq-II:PCBBiF:[Ir(dppm)2(a After co-depositing 20nm so that the ratio is cac), 0.8:0.2:0.06 (=2mD It will be BTBPDBq-II:PCBBiF:[Ir(dppm)2(acac)]). A 20nm co-deposited layer was used to form the light-emitting layer 113.

[0307] Subsequently, 2mDBTBPDBq-II was deposited onto the light-emitting layer 113 at a 10 nm thickness, and then the above structure was constructed. Bathophenanthroline (abbreviated as BPhen), represented by formula (vi), is deposited at a 5 nm depth and then electrolyzed. A sub-transport layer 114 was formed.

[0308] After forming the electron transport layer 114, lithium fluoride (LiF) and BPhen are added in a volume ratio. To achieve a ratio of 0.75:0.25 (=LiF:BPhen), a 35nm co-deposit was performed, followed by electron injection. An underlayer 115 is formed, followed by the deposition of aluminum to a film thickness of 200 nm. The second electrode 102 was then formed to create the light-emitting element 2 of this embodiment.

[0309] The element structure of 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 under a nitrogen atmosphere, so that the light-emitting element is not exposed to the atmosphere. The process involves sealing with a glass substrate (applying a sealing material around the element and UV treatment during sealing). After heat treatment at 80°C for 1 hour, the initial characteristics of the light-emitting element 2 were measured. Furthermore, no special measures were taken to improve the extraction efficiency of the glass substrate on which the light-emitting element was fabricated. not present.

[0312] Figure 26 shows the brightness-current density characteristics of the light-emitting element 2, and Figure 27 shows the current efficiency-brightness characteristics. The pressure characteristics are shown in Figure 28, the current-voltage characteristics in Figure 29, and the external quantum efficiency-luminance characteristics in Figure 30. The light spectrum of the light-emitting element 2 is shown in Figure 31. 2 Major in the vicinity The characteristics are shown in Table 4. The measurement method is the same as in Example 3. Also, in Figure 30 above... The external quantum efficiency shown is the value assuming a Lambertsian, and is shown in the table below. Quantum efficiency is measured by the angular dependence of the emission spectrum and the deviation from the Lambertsian distribution. The corrected, true value is used.

[0313] [Table 4]

[0314] As shown in Figures 26 to 31 and Table 4, the light-emitting element 2, which is one embodiment of the present invention, has good luminous efficiency. It was found to be a yellow-orange light-emitting element. In particular, its external quantum efficiency exceeds 35%. EL Given that the limit of the device's light extraction efficiency is thought to be around 30%, this device It can be seen that Vice's external quantum efficiency is extremely high. This is because TAPC-02 with a low refractive index is used. This is due to the improved light extraction efficiency resulting from its use. [Examples]

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

[0316] [ka]

[0317] (Method for fabricating the light-emitting element 3) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. The first electrode 101 was formed by depositing a film using the 3D method. The film thickness was set to 70 nm, and the electrode surface The product was set to 2mm x 2mm.

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

[0319] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0320] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, Calcium fluoride (CaF2) and the above structural formula (vii) are obtained by a vapor deposition method using resistance heating. Represented as 1,1-bis-(4-bis(4-methylphenyl)-aminophenyl)- Cyclohexane (abbreviated as TAPC) and molybdenum(VI) oxide are mixed in a weight ratio of 3:1:0. After co-depositing at 45 nm to achieve a 0.5 (=CaF2:TAPC:molybdenum oxide) layer, The 4,4'-bis(9-carbazole)-2,2'-dimethyl- represented by structural formula (i) Biphenyl (abbreviation: dmCBP) and molybdenum(VI) oxide are mixed in a weight ratio of 2:0.5. A hole injection layer 111 was formed by co-depositing 5 nm of material so that the ratio was dmCBP:MoOx.

[0321] Next, on the hole injection layer 111, the 4,4'-(1,1-cyan represented by the above structural formula (ii) is injected. (4-cyclohexylbenzene-1-yl)a After depositing 15 nm of minobenzene (abbreviation: TAPC-02), the above structural formula (iii) Represented as N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-( 9-phenyl-9H-carbazole-3-yl)phenyl]-9H-fluoren-2-yl A hole transport layer 112 is formed by depositing MIN (abbreviated as PCBBiF) to a thickness of 5 nm. did.

[0322] Next, the 2-[3'-(dibenzothiophen-4-yl) represented by the above structural formula (iv) Biphenyl-3-yl[f,h]quinoxaline (abbreviation: 2mDBTBPDBq) -II) and PCBBiF and the screw {2-[6-(4-S) represented by the above structural formula (ix) Ano-2,6-dimethylphenyl)-4-pyrimidinyl-κN 3 ]phenyl-κC}(2 ,4-pentanedionato-κO,O') Iridium(III) (abbreviation: [Ir(ppm- dmCP)2(acac)]) and in weight ratio 0.75:0.25:0.05 (=2mD BTBPDBq-II:PCBBiF:[Ir(ppm-dmCP)2(acac)]) A light-emitting layer 113 was formed by co-depositing at a density of 40 nm in such a manner.

[0323] Subsequently, 2mDBTBPDBq-II was deposited onto the light-emitting layer 113 at a 5nm thickness, and then the above structure was constructed. The formula (x) represents 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1, 10-phenanthroline (abbreviated as NBPhen) is deposited at a 5nm layer to form the electron transport layer 114. I did it.

[0324] After forming the electron transport layer 114, lithium fluoride (LiF) and BPhen are added in a volume ratio. To achieve a ratio of 0.75:0.25 (=LiF:BPhen), a 35nm co-deposit was performed, followed by electron injection. An underlayer 115 is formed, followed by the deposition of aluminum to a film thickness of 200 nm. The second electrode 102 was then formed to create the light-emitting element 3 of this embodiment.

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

[0326] [Table 5]

[0327] The light-emitting element 3 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element is not exposed to the atmosphere. The process involves sealing with a glass substrate (applying a sealing material around the element and UV treatment during sealing). After heat treatment at 80°C for 1 hour, the initial characteristics of the light-emitting element 3 were measured. Furthermore, no special measures were taken to improve the extraction efficiency of the glass substrate on which the light-emitting element was fabricated. not present.

[0328] Figure 32 shows the brightness-current density characteristics of the light-emitting element 3, and Figure 33 shows the current efficiency-brightness characteristics. The pressure characteristics are shown in Figure 34, the current-voltage characteristics in Figure 35, and the external quantum efficiency-luminance characteristics in Figure 36. The light spectrum of the light-emitting element 3 is shown in Figure 37. 2 Major in the vicinity The characteristics are shown in Table 6. The measurement method is the same as in Example 3. Also, in Figure 36 above... The external quantum efficiency shown is the value assuming a Lambertsian, and is shown in the table below. Quantum efficiency is measured by the angular dependence of the emission spectrum and the deviation from the Lambertsian distribution. The corrected, true value is used.

[0329] [Table 6]

[0330] As shown in Figures 32 to 37 and Table 4, the light-emitting element 3, which is one embodiment of the present invention, has an external quantum efficiency of 4 It was found that the light-emitting element exhibits a very high efficiency of 2.5%. Therefore, the present invention It has been found that by using a compound according to one embodiment, a light-emitting element with high luminescence efficiency can be obtained. 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') Synthesis method of rhidium(III) (abbreviation: [Ir(ppm-dmCP)2(acac)]) This will be explained. The structure of [Ir(ppm-dmCP)2(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(pinacolate)dibo 18.35g of chlorine, 21.73g of potassium acetate, and 240mL of dimethyl sulfoxide are prepared in a solution. The contents were placed in a three-necked flask fitted with a flow tube, and the inside was purged with nitrogen. The contents of the flask were then stirred under reduced pressure. After degassing, [1,1'-bis(diphenylphosphino)ferrocene]palladium (II) Dichloride dichloromethane adduct (abbreviation: Pd(dppf)Cl2·CH2Cl 2) 0.59 g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Abbreviation: S-Phos) 0.59g was added and stirred at 100°C for 32.5 hours. Afterward, extraction was performed with toluene. Subsequently, hexane:ethyl acetate = 10:1 was used as the developing solution. The target product was obtained by purification using silica gel column chromatography (white solid, yield). 5.89 g, yield 48%). The synthesis scheme for Step 1 is shown in formula (a-1) below.

[0334] [ka]

[0335] <Step 2: Synthesis of 4-(4-cyano-2,6-dimethylphenyl)-6-phenylpyrimidine (abbreviation: Hppm-dmCP)> > Next, 0.74 g of 4-chloro-6-phenylpyrimidine, 1.28 g of 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile obtained in the above Step 1, 3.23 g of tripotassium phosphate, 43 mL of toluene, and 4.3 mL of water were placed in a three-necked flask equipped with a reflux tube, and the inside was purged with nitrogen. After stirring and degassing the inside of the flask under reduced pressure, 0.094 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) and 0.19 g of tris(2,6-dimethoxyphenyl)phosphine (abbreviation: P(2,6-MeOPh)3) were added, and the mixture was stirred at 110 °C for 23 hours. After a predetermined time had elapsed, extraction with toluene was performed. Then, purification was carried out by silica gel column chromatography using hexane:ethyl acetate = 5:1 as the developing solvent to obtain the target pyrimidine derivative, Hppm-dmCP (white solid, yield 0.97 g, yield 88%). The synthesis scheme of Step 2 is shown in the following formula (a-2). ,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl)benzonitrile 1.28 g, tripotassium phosphate 3.23 g, toluene 43 m L, water 4.3 mL were placed in a three-necked flask equipped with a reflux tube, and the inside was purged with nitrogen. The flask was stirred and degassed under reduced pressure, and then tris(dibenzylideneacetone)dipalladium( 0) (abbreviation: Pd2(dba)3) 0.094 g, tris(2,6-dimethoxyphenyl )phosphine (abbreviation: P(2,6-MeOPh)3) 0.19 g were added, and the mixture was stirred at 110 °C for 23 hours. After a predetermined time had elapsed, extraction with toluene was performed. Then, hexane:acetic ethyl = 5:1 was used as the developing solvent for silica gel column chromatography for purification, and the target pyrimidine derivative, Hppm-dmCP was obtained (white solid, yield 0.97 g, yield 88% ). The synthesis scheme of Step 2 is shown in the following formula (a-2).

[0336]

Chemical formula

[0337] <Step 3: Synthesis of di-μ-chloro-tetrakis{2-[6-(4-cyano-2,6-dimethyl phenyl)-4-pyrimidinyl-κN 3 phenyl-κC}diiridium(III)( abbreviation: [Ir(ppm-dmCP)2Cl]2)> Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and Hppm-d obtained in the above Step 2 mCP 1.60g, Iridium chloride hydrate (IrCl3·H2O) (manufactured by Furuya Metal Co., Ltd.) 0 0.81g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Next, microwaves (2.45 GHz, 100 W) were irradiated for 3 hours to induce a reaction. Afterward, the resulting residue was washed by suction filtration with methanol to obtain the dinuclear complex [Ir(ppm-dmC We obtained P)2Cl]2 (orange solid, yield 1.45g, yield 67%). Step 3 synthesis Chiem is shown in the following equation (a-3).

[0338] [ka]

[0339] <Step 4: Synthesis of [Ir(ppm-dmCP)2(acac)]> 20 mL of 2-ethoxyethanol, the dinuclear complex obtained in step 3 above, [Ir(ppm-d mCP)2Cl] 21.44g, Acetylacetone (abbreviation: Hacac) 0.41g, Place 0.93g of sodium carbonate into a round-bottom flask fitted with a reflux condenser, and rinse the inside of the flask with Algo The material was replaced. Then, microwaves (2.45 GHz, 100 W) were irradiated for 4 hours. The residue was filtered by suction with dichloromethane, and the filtrate was concentrated. The resulting solid was hexagonal. Silica gel column chromatography using a solvent ratio of 2:1 (san:ethyl acetate) After purification, recrystallization was performed using a mixed solvent of dichloromethane and methanol to obtain organic gold The genus complex, [Ir(ppm-dmCP)2(acac)], was obtained as a yellow-orange powder (yield 0 0.19 g, yield 7%. The obtained yellow-orange powder 0.19 g was subjected to the train sublimation method. The solution was purified by sublimation. The sublimation purification conditions were: pressure 2.7 Pa, argon gas flow rate 11 mL / The solid was heated to 355°C while flowing at min. After sublimation purification, the target yellow-orange solid was collected. It was obtained in an amount of 0.092 g with a yield of 48%. The synthesis scheme for 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 Analysis results by H-NMR The results are shown below. From these results, it can be seen that in this synthesis example, [Ir(ppm-dmCP)2(a It was found that (cac) was obtained.

[0342] 1 H-NMR.δ(CDCl3):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: 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: Sea 406: sealing material, 407: encapsulation substrate, 412: pad, 420: IC chip, 5 01: Anode, 502: Cathode, 511: First light-emitting unit, 512: Second light-emitting unit , 513: Charge generation layer, 601: Drive circuit section (source line drive circuit), 602: Pixel section, 6 03: Drive circuit section (gate wire drive circuit), 604: Encapsulation 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: Underlying insulating film, 1003: Gate insulating film, 1006: Gate 1007: gate electrode, 1008: gate electrode, 1020: first interlayer insulating film , 1021: second interlayer insulating film, 1022: electrode, 1024W: first electrode, 1024R : First electrode, 1024G: First electrode, 1024B: First electrode, 1025: Separation 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: Drive circuit section, 1042: Peripheral section, 2001: Housing, 2002: Light source, 2100: Robot, 2110: Processing unit, 2101: Illuminance sensor, 2102: Microphone, 2103: Top camera, 2104: Speaker, 2105: Display, 2106: Lower camera, 2107: Obstacle sensor, 2108: Movement 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 part, 5013: Earphone, 5100: Cleaning rod Bot, 5101: Display, 5102: Camera, 5103: Brush, 5104: Control 5150: Mobile information terminal, 5151: Casing, 5152: Display area, 5153: Bent section, 5120: debris, 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: Enclosure, 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: Personal digital assistant, 9311: Display panel, 9312: Display area Area, 9313: Hinge, 9315: Casing

Claims

1. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having 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), Ar1 and Ar ４ Each of these independently represents one of the following: a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted triphenyldiyl group. Ar2 and Ar3 each independently represent a substituted or unsubstituted biphenyldiyl group. １ ~R ４ Each of these 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. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

2. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G1), in contact with the first electrode. 【Chemistry 2】 (However, in the above general formula (G1), Ar1 and Ar ４ Each of these independently represents one of the following: a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted triphenyldiyl group. Ar2 and Ar3 each independently represent a substituted or unsubstituted biphenyldiyl group. １ ~R ４ Each of these 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. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

3. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G1) on the first electrode side of the light-emitting layer. 【Transformation 3】 (However, in the above general formula (G1), Ar １ to Ar ４ each independently represents any one of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, and a substituted or unsubstituted triphenyldiyl group. R １ to R ４ each independently represents 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.)

4. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G1), in contact with the first electrode. 【Chemistry 4】 (However, in the above general formula (G1), Ar １ ~Ar ４ Each of these independently represents one of the following: a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted triphenyldiyl group. １ ~R ４ Each of these independently represents a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

5. In claim 3 or claim 4, Ar ２ and Ar ３ A light-emitting element in which each of the elements is independently a substituted or unsubstituted biphenyldiyl group.

6. In claim 3 or claim 4, Ar １ ~Ar ４ A light-emitting element in which each of the elements is independently a substituted or unsubstituted phenylene group.

7. In any one of claims 1 to 4, Ar １ and Ar ４ A light-emitting element in which each of the elements is independently a substituted or unsubstituted phenylene group.

8. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G2) on the first electrode side of the light-emitting layer. 【Transformation 5】 (However, in the above general formula (G2), R １ ~R ４ Each of these independently represents a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

9. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G2) in contact with the first electrode. 【Transformation 6】 (However, in the above general formula (G2), R １ ~R ４ Each of these independently represents a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

10. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G4) on the first electrode side of the light-emitting layer. 【Transformation 7】 (However, in the above general formula (G4), R １ ~R ４ Each of these 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. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

11. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G4) in contact with the first electrode. 【Transformation 8】 (However, in the above general formula (G4), R １ ~R ４ Each of these 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. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

12. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G5) on the first electrode side of the light-emitting layer. 【Chemistry 9】 (However, in the above general formula (G5), R １ ~R ４ Each of these 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. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

13. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G5) in contact with the first electrode. 【Chemistry 10】 (However, in the above general formula (G5), R １ ~R ４ Each of these 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. Each of m, n, p, and s independently represents an integer from 0 to 3, while any two or more of m, n, p, and s independently represent an integer from 1 to 3.

14. In any one of claims 1 to 13, A light-emitting element in which m, n, p, and s each independently represent an integer between 1 and 3.

15. In any one of claims 1 to 14, A light-emitting element where m, n, p, and s are 1.

16. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G3) on the first electrode side of the light-emitting layer. 【Chemistry 11】 (However, in the above general formula (G3), R １ ~R ４ Each of these independently represents a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms.

17. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G3) in contact with the first electrode. 【Chemistry 12】 (However, in the above general formula (G3), R １ ~R ４ Each of these independently represents a substituted or unsubstituted cyclic saturated hydrocarbon group having 5 to 12 carbon atoms.

18. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G6) on the first electrode side of the light-emitting layer. 【Chemistry 13】 (However, in the above general formula (G6), R １ ~R ４ Each of these 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.

19. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following general formula (G6) in contact with the first electrode. 【Chemistry 14】 (However, in the above general formula (G6), R １ ~R ４ Each of these 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.

20. In any one of claims 1 to 19, R １ ~R ４ A light-emitting element in which each of the elements is independently a cyclohexyl group.

21. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following structural formula, located on the first electrode side of the light-emitting layer. 【Chemistry 15】

22. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following structural formula, in contact with the first electrode. 【Chemistry 16】

23. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following structural formula, located on the first electrode side of the light-emitting layer. 【Chemistry 17】

24. A first electrode that is translucent and a second electrode have a light-emitting layer between them. A light-emitting element having a layer containing an organic compound represented by the following structural formula, in contact with the first electrode. [Chemistry 18]

25. A light-emitting device comprising a light-emitting element according to any one of claims 1 to 24, a transistor, and at least one of a substrate.

26. A light-emitting device according to claim 25, and at least one of a sensor, an operation button, a speaker, and a microphone, A powerful electronic device.

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

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