Light-emitting device, light-emitting apparatus, light-emitting module, electronic appliance, and illumination apparatus

Abstract

To provide a light-emitting device including an organic compound with high heat resistance and having high luminous efficiency and reliability.SOLUTION: An organic compound is represented by a particular general formula.SELECTED DRAWING: None

Description

Technical Field

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

[0002] Note that one aspect of the present invention is not limited to the above technical field. As the technical field of one aspect of the present invention, semiconductor devices, display devices, light-emitting devices, power storage devices, storage devices, electronic devices, lighting devices, input devices (e.g., touch sensors, etc.), input / output devices (e.g., touch panels, etc.), their driving methods, or their manufacturing methods can be given as an example.

Background Art

[0003] Research and development of light-emitting devices (also referred to as organic EL devices or organic EL elements) using the phenomenon of organic electroluminescence (EL) has been actively conducted. The basic configuration of an organic EL device is one in which a layer containing a light-emitting organic compound (hereinafter also referred to as a light-emitting layer) is sandwiched between a pair of electrodes. By applying a voltage to this organic EL device, light emission from the light-emitting organic compound can be obtained.

[0004]

[0005] An organic EL device has characteristics such as being easily thinned and lightened, being able to respond quickly to an input signal, and being drivable using a DC low-voltage power supply, and is suitable for a display device.

[0005] Moreover, since an organic EL device can be formed in a film shape, light emission in a planar shape can be obtained. Therefore, a large-area light-emitting device can be easily formed. This is a characteristic that is difficult to obtain with a point light source typified by an LED (light-emitting diode) and a line light source typified by a fluorescent lamp. Because of its color, an organic EL device also has utility value as a surface light source applicable to lighting devices and the like. Is high.

[0006] Patent Document 1 discloses an aromatic amine compound with high hole transportability as a material that can be used in a light-emitting device. Is disclosed.

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0008] One aspect of the present invention is to provide a novel organic compound. Or, one aspect of the present invention is to provide an organic compound with high heat resistance. Or, one aspect of the present invention is to provide an organic compound with high sublimability. Or, one aspect of the present invention is to provide a novel organic compound that can be used in a light-emitting device. Or, one aspect of the present invention is to provide a novel organic compound that can be used as a hole transport material in a light-emitting device. Or, one aspect of the present invention is to provide a novel organic compound that can be used as a host material for dispersing a light-emitting substance in a light-emitting device. Or, one aspect of the present invention is to provide a light-emitting device with high luminous efficiency. Or, one aspect of the present invention is to provide a light-emitting device with a low driving voltage. Or, one aspect of the present invention is to provide a light-emitting device with a low driving voltage. Or, one aspect of the present invention is to provide a novel organic compound that can be used in a light-emitting device. Or, one aspect of the present invention is to provide a novel organic compound that can be used as a hole transport material in a light-emitting device. Or, one aspect of the present invention is to provide a novel organic compound that can be used as a host material for dispersing a light-emitting substance in a light-emitting device. Or, one aspect of the present invention is to provide a novel organic compound that can be used as a host material for dispersing a light-emitting substance in a light-emitting device. Is one of the problems.

[0009] Or, one aspect of the present invention is to provide a light-emitting device with high luminous efficiency. Is one of the problems. Or, one aspect of the present invention is to provide a light-emitting device with a low driving voltage. Let it be so. Or, one aspect of the present invention is to provide a long - life light - emitting device as one of the problems. Or, one aspect of the present invention is to provide a light - emitting device with high heat resistance as one of the problems. Let it be so.

[0010] Note that the description of these problems does not prevent the existence of other problems. One aspect of the present invention is not necessarily required to solve all of these problems. It is possible to extract other problems from the description of the specification, drawings, and claims.

Means for Solving the Problems

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

[0012]

Chemical formula

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

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

[0015] [ka]

[0016] In general formula (G1), R 2 ~R 13 , R 21 ~R 29 , R 31 ~R 39 , and R 41 ~R 4 8 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a aryl group having 3 to 6 carbon atoms. A cycloalkyl group or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Represents. R 21 and R 22 may be bonded to each other to form a spiro ring.

[0017] In the general formula (G0) and the general formula (G1), R 35 ~R 39 Either one of , a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group. is preferred.

[0018] In the general formula (G0) and the general formula (G1), R 21 and R 22 are identical, And represents an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. It is preferable to do so.

[0019] In the general formula (G0) and the general formula (G1), R 21 and R 22 Both are methi Alternatively, R21 and R 22 both preferably represent an unsubstituted phenyl group. Alternatively, R and R 21 and R 22 preferably combine with each other to form a spiro ring. For example, R and R 21 and R 22 both preferably represent a substituted or unsubstituted phenyl group, and the phenyl groups are preferably bonded to each other to form a spirobifluorene ring. Preferably.

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

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

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

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

[0024] One aspect of the present invention is a light-emitting device having any of the above-configured light-emitting devices and one or both of a transistor and a substrate. ​​​​​​​​

[0025] One embodiment of the present invention is a flexible printed circuit board (FPC) having the above-mentioned light-emitting device. ble Printed Circuit, hereafter referred to as FPC) or TCP (Ta A light emitting module equipped with a connector such as a PE Carrier Package or COG (Chip On Glass) or COF (Chip On Light-emitting modules such as light-emitting modules in which integrated circuits (ICs) are mounted using the film method, etc. In addition, the light-emitting module according to one embodiment of the present invention includes only one of the connector and the IC. or both.

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

[0027] One aspect of the present invention is a light-emitting device having any of the above configurations, a housing, a cover, and a support stand. and at least one of the above. Effect of the Invention

[0028] According to one embodiment of the present invention, a novel organic compound can be provided. According to one embodiment of the present invention, an organic compound having high sublimability can be provided. According to one embodiment of the present invention, a novel organic compound that can be used in a light-emitting device can be provided. According to one embodiment of the present invention, a compound having a hole transporting property can be provided as a hole transporting material in a light-emitting device. According to one embodiment of the present invention, a novel organic compound capable of forming a light-emitting device can be provided. The present invention provides a novel organic compound that can be used as a host material for dispersing a light-emitting substance in the above-mentioned device. can be provided.

[0029] One aspect of the present invention can provide a light-emitting device with high luminous efficiency. According to one aspect of the present invention, a light-emitting device with a low driving voltage can be provided. According to one aspect of the present invention, a light-emitting device with a long lifespan can be provided. According to one aspect of the present invention, a light-emitting device with high heat resistance can be provided.

[0030] Note that the description of these effects does not preclude the existence of other effects. One aspect of the present invention does not necessarily have to have all of these effects. It is possible to extract other effects from the descriptions in the specification, drawings, and claims.

Brief Description of the Drawings

[0031]

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BEST MODE FOR CARRYING OUT THE INVENTION

[0032] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and those skilled in the art can easily understand that the form and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments shown below. Moreover, in the configuration of the invention described below, the same reference numerals are commonly used among different drawings for the same part or parts having the same or similar functions, and the repeated description thereof will be omitted. Also, when referring to similar functions, the hatching patterns may be the same, and there may be cases where no particular reference numerals are attached. In addition, the positions, sizes, ranges, etc. of the respective components shown in the drawings may not represent the actual positions, sizes, ranges, etc. for the sake of easy understanding. For this reason, the disclosed invention is not necessarily limited to the positions, sizes, ranges, etc. disclosed in the drawings. It should be noted that the terms "film" and "layer" may, in some cases or depending on the situation,

[0033]

[0034]

[0035]

[0035] Thus, they can be interchanged with each other. For example, the term "conductive layer" can be changed to the term "conductive film" . Or, for example, the term "insulating film" can be changed to the term "insulating layer".

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

[0037] [Structure of the organic compound of one aspect of the present invention] The organic compound of one aspect of the present invention is a tertiary amine, and to the nitrogen of the amine, a biphenyl ortho-position of the skeleton, a fluorene skeleton, and a terphenylene skeleton are bonded, and to the phenylene group farthest from the nitrogen of the amine of the terphenylene skeleton, a carbazole skeleton is bonded .

[0038] For light-emitting devices used in high-temperature environments such as in-vehicle applications, high heat resistance is required. Also, when high temperature is applied during the manufacturing process of the product, such as in the sealing process using glass frit, high heat resistance is required for the light-emitting device. From these facts, for the materials used in the light-emitting device, the glass transition temperature (Tg) is required to be 100 °C or higher, and further 120 °C or higher in some cases. In one aspect of the present invention, since the Tg of the organic compound can be 100 °C or higher, and further is 120 °C or higher, a material suitable for a light-emitting device that requires high heat resistance can be provided. On the other hand, the production of the light-emitting device is often performed by vacuum evaporation. In that case, the material used in the light-emitting device needs to have both high heat resistance and high sublimability, and the sublimation temperature is preferably 500 °C or lower, more preferably 400 °C or lower. This ​In one embodiment of the present invention, a material having not only high heat resistance but also high sublimation property can be provided, It is possible to provide materials that have high productivity in terms of device fabrication.

[0039] The organic compound of one embodiment of the present invention has high hole-transporting and electron-blocking properties. The organic compounds can be used as hole transport materials in light-emitting devices. In addition, the organic compound according to one embodiment of the present invention can be used as a host for dispersing a light-emitting substance in a light-emitting device. By using the organic compound of one embodiment of the present invention, a light-emitting device can be The light emitting efficiency and reliability of the device can be improved.

[0040] The organic compound according to one embodiment of the present invention can be used in light-receiving devices such as organic photodiodes and light-emitting devices. In light-receiving and light-receiving devices, the carrier transport material (hole It can be used as a transport material.

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

[0042] [ka]

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

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

[0045] [ka]

[0046] In general formula (G1), R 2 ~R 13 , R 21 ~R 29 , R 31 ~R 39 , and R 41 ~R 4 8 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a aryl group having 3 to 6 carbon atoms. A cycloalkyl group or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Represents R 21 and R 22 may be bonded to each other to form a spiro ring.

[0047] R 35 ~R 39 Any one of them preferably represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group. Thereby, the heat resistance of the organic compound can be enhanced.

[0048] When the 9-position of the fluorenyl group is hydrogen, the acidity of the hydrogen increases, and there is a concern that the reliability of the light-emitting device may decrease. Therefore, R at the 9-position of the fluorenyl group and R 21 22 preferably represent a substituent rather than hydrogen. Considering the heat resistance and sublimability of the organic compound represented by the general formula (G1), R and R preferably each independently represent an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group. Or 21 R 22 and R are preferably the same and represent an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group. Also, from the perspective of synthesis cost, R 21 and R 22 are preferably the same.

[0049] Also, from the perspective of synthesis cost, R 21 and R 22 are preferably the same.

[0050] R 21 and R 22 both preferably represent a methyl group. Thereby, the sublimability of the organic compound can be enhanced. Or, R and R 21 both preferably represent an unsubstituted phenyl group. 22 Thereby, the heat resistance of the organic compound can be enhanced.

[0051] Or, R 21 and R 22 ​​​​​In order to have high heat resistance or high reliability, it is preferably bonded to each other to form a spiro ring. For example, R 21 and R 22 are both substituted or unsubstituted phenyl groups, and it is preferable that the phenyl groups are bonded to each other to form a spirobifluorene ring.

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

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

[0054] Examples of the cycloalkyl group having 3 to 6 carbon atoms in the general formula (G0) and the general formula (G1) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.

[0055] Examples of the substituted or unsubstituted aryl group having 6 to 13 carbon atoms in the general formula (G0) and the general formula (G1) include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, and ​​​A t-butyl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, a 1-naphthyl group, 2 -naphthyl group, a 9H-fluorenyl group, a 9,9-dimethyl-9H-fluorenyl group, 9, 9'-spirobi[9H-fluorene]-yl group, etc. may be mentioned.

[0056] In the "substituted or unsubstituted X" (X is various rings, skeletons, groups, etc.) in the general formula (G0) and the general formula (G1), when X has a substituent, examples of the substituent include a methyl group, an e thyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, t ert-butyl group, a pentyl group, a hexyl group, etc., an alkyl group having 1 to 6 carbon atoms, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc., a cycloalkyl group having 3 to 6 carbon atoms, and a phenyl group, a naphthyl group, a biphenyl group, etc., an aryl group having 6 to 13 carbon atoms, such as this, may be mentioned. Examples of specific examples of the organic compound of one aspect of the present invention include the organic compounds shown in structural formulas (100) to (246). However, the present invention is not limited thereto.

[0057]

[0058]

Chemical formula

[0059]

Chemical formula

[0060]

Chemical formula

[0061] ​​​

[0062]

Chem.

[0063]

Chem.

[0064]

Chem.

[0065]

Chem.

[0066]

Chem.

[0067]

Chem.

[0068]

Chem.

[0069]

Chem.

[0070]

Chem.

[0071]

Chem.

[0072] [Chemistry]

[0073] [Chemistry]

[0074] [Chemistry]

[0075] [Chemistry]

[0076] [Chemistry]

[0077] [Chemistry]

[0078] [Chemistry]

[0079] [Chemistry]

[0080] [Chemistry]

[0081] [Chemistry]

[0082] [Chemistry]

[0083] [Synthesis method of an organic compound according to an aspect of the present invention] As the synthesis method of the organic compound according to an aspect of the present invention, various reactions can be applied. First The synthesis method of the organic compound represented by the general formula (G0) will be exemplified below. Hereinafter, an example of the synthesis method of the organic compound represented by the general formula (G 1) will be described.

[0084] [Chemical formula]

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

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

[0087] First, as shown in the synthesis scheme (a-1), a 9-biphenyl-9H-carbazole compound (compound 1) and a dihalogenated benzene (compound 2) are coupled with each other Next, a halogenated 9 - terphenyl - 9H - carbazole compound (Compound 3) is obtained.

[0088]

Chemical formula

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

[0090] In the synthetic scheme (a - 1), when performing the Suzuki - Miyaura coupling reaction using a palladium catalyst, X 1 represents a halogen, and one of X 2 and X 3 represents a boronic acid group or an organo boron group, and the other represents a halogen or a triflate group. As the halogen, iodine bromine, or chlorine is preferred.

[0091] In this reaction, palladium compounds such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate II), [1,1 - bis(diphenylphosphino)ferrocene]palladium(II) dichloro ride, tetrakis(triphenylphosphine)palladium(0), etc. can be used together with ligands such as tri(tert - butyl)phosphine, tri(n - hexyl)phosphine, tricyclo hexylphosphine, di(1 - adamantyl)-n - butylphosphine, 2 - dicyclohex xylphosphino - 2’,6’ - dimethoxybiphenyl, tri(ortho - tolyl)phosph ine. In this reaction, sodium tert - butoxide Organic bases such as amines, and inorganic bases such as potassium carbonate, cesium carbonate, and sodium carbonate can be used. It can be used.

[0092] In this reaction, as the solvent, toluene, xylene, benzene, tetrahydrofuran, dioxane, ethanol, methanol, water, diethylene glycol dimethyl ether, ethylene glycol monomethyl ether, etc. can be used. The reagents that can be used in this reaction are not limited to these. xane, ethanol, methanol, water, diethylene glycol dimethyl ether, ethylene glycol monomethyl ether, etc. can be used. The reagents that can be used in this reaction are not limited to these. In the synthetic scheme (a-1), the Utada-Kosugi-Stille coupling reaction using an organotin compound, the Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc. can also be carried out. The reagents that can be used in this reaction are not limited to these.

[0093] In the synthetic scheme (a-1), the Utada-Kosugi-Stille coupling reaction using an organotin compound, the Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc. can also be carried out. ring reaction, the Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc. can also be carried out. lead compound, the Negishi coupling reaction, the Ullmann reaction using copper or a copper compound, etc. can be carried out. It can also be carried out.

[0094] When using the Utada-Kosugi-Stille coupling reaction, among X 2 and X 3 one represents an organotin group and the other represents a halogen. That is, among compound 1 and compound 2, one is an organotin compound and the other is a halide. ring reaction, the Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc. can also be carried out. ring reaction, the Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc. can also be carried out.

[0095] When using the Kumada-Tamao-Corriu coupling reaction, among X 2 and X 3 one represents a magnesium halide group and the other represents a halogen. That is, among compound 1 and compound 2, one is a Grignard reagent and the other is a halide. ring reaction, the Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc. can also be carried out. ring reaction, the Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, the Negishi coupling reaction using an organozinc compound, the Ullmann reaction using copper or a copper compound, etc. can also be carried out.

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

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

[0098] [Chemical formula]

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

[0100] In the synthesis scheme (a-2), a Suzuki-Miyaura coupling reaction using a palladium catalyst, a Negishi coupling reaction using an organotin compound, a Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, a Sonogashira coupling reaction using an organozinc compound, a Ullmann reaction using copper or a copper compound, etc. can be carried out. Details of using these reactions can be referred to the description in the synthesis scheme (a-1). When using these reactions, the details can be referred to the description in the synthesis scheme (a-1).

[0101] Compound 3 can be used in a coupling reaction in combination with various diarylamine compounds, and it can be said to be an effective compound that greatly contributes to the simplification and development of material development. Also , since Compound 3 has a halogen, not only the amination reaction but also the Suzuki-Miyaura coupling reaction, the Migita-Kosugi-Stille coupling reaction, the Kumada-Tamao-Corriu coupling reaction, the Negishi coupling reaction, the Ullmann reaction, etc. can be used as raw materials, and it can be widely applied to coupling reactions for carbon -carbon bond formation, and it can be said to be an effective and useful compound.

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

[0103] [Chemical formula]

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

[0105] The synthetic scheme (a-3) can be carried out by a backward Hartwig amination reaction using a palladium catalyst. When carrying out this reaction, as the palladium catalyst, bis (dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis (diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis( triphenylphosphine)palladium(0), allylpalladium(II) chloride (dimer), etc. palladium compounds can be used. Also, as the ligand, tri(te rt-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine fin, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, di-t ert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)), etc. can be used. In this reaction, organic bases such as sodium tert butoxide and inorganic bases such as potassium carbonate, cesium carbonate, and sodium carbonate can be used. In this reaction, solvents such as toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used. Note that the reagents that can be used in this reaction are not limited to these. rt-butoxide and the like, and inorganic bases such as potassium carbonate, cesium carbonate, and sodium carbonate can be used. In this reaction, solvents such as toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used. Note that the reagents that can be used in this reaction are not limited to these. In addition, when performing the synthesis scheme (a-3) by the Ullmann reaction, the reagents that can be used are copper or copper compounds, and as the base, inorganic bases such as potassium carbonate can be mentioned. In this reaction, the solvents that can be used are 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, benzene, etc. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU or xylene with a high boiling point. Also, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use DMPU. Note that the reagents that can be used in this reaction are not limited to these. In addition, when performing the synthesis scheme (a-3) by the Ullmann reaction, the reagents that can be used are copper or copper compounds, and as the base, inorganic bases such as potassium carbonate can be mentioned. In this reaction, the solvents that can be used are 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, benzene, etc.

[0106] Moreover, when carrying out the synthesis scheme (a-3) by the Ullmann reaction, the reagents that can be used are copper or copper compounds, and as the base, inorganic bases such as potassium carbonate can be mentioned. In this reaction, the solvents that can be used are 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, benzene, etc. In this reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU or xylene with a high boiling point. Also, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use DMPU. Note that the reagents that can be used in this reaction are not limited to these. In this reaction, the solvents that can be used are 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, benzene, etc. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU or xylene with a high boiling point. Also, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use DMPU. Note that the reagents that can be used in this reaction are not limited to these. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU or xylene with a high boiling point. Also, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use DMPU. Note that the reagents that can be used in this reaction are not limited to these. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU or xylene with a high boiling point. Also, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use DMPU. Note that the reagents that can be used in this reaction are not limited to these. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU or xylene with a high boiling point. Also, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use DMPU. Note that the reagents that can be used in this reaction are not limited to these. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU or xylene with a high boiling point. Also, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use DMPU. Note that the reagents that can be used in this reaction are not limited to these.

[0107] ≪Synthesis method 2 of the organic compound represented by the general formula (G1)≫ The organic compound represented by the general formula (G1) can be synthesized using the synthetic scheme (b-1). It can be done.

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

[0109]

Chemical formula

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

[0111] In the synthetic scheme (b-1), a Suzuki-Miyaura coupling reaction using a palladium catalyst, a Negishi coupling reaction using an organotin compound, a Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, a Hiyama coupling reaction using an organozinc compound, a reaction using copper or a copper compound, etc. can be carried out. Details of the cases where these reactions are used can be referred to the description in the synthetic scheme (a-1). reaction, a Negishi coupling reaction using an organotin compound, a Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, a Hiyama coupling reaction using an organozinc compound, a reaction using copper or a copper compound, etc. can be carried out. Details of the cases where these reactions are used can be referred to the description in the synthetic scheme (a-1). used, a Kumada-Tamao-Corriu coupling reaction using a Grignard reagent, a Hiyama coupling reaction using an organozinc compound, a reaction using copper or a copper compound, etc. can be carried out. Details of the cases where these reactions are used can be referred to the description in the synthetic scheme (a-1). g reaction, a reaction using an organozinc compound, a reaction using copper or a copper compound, etc. can be carried out. Details of the cases where these reactions are used can be referred to the description in the synthetic scheme (a-1). For details of these reaction application scenarios, refer to the description in the synthetic scheme (a-1).

[0112] ≪Synthesis method 3 of the organic compound represented by the general formula (G1)≫ The organic compound represented by the general formula (G1) can be synthesized using the synthetic scheme (c-1). It is possible to do so.

[0113] As shown in the synthetic scheme (c-1), by coupling a 9-phenyl-9H-carbazole compound (Compound 9) and a triarylamine compound (Compound 10), an organic compound represented by the general formula (G1) can be obtained. It is possible to do so. The organic compound represented by the general formula (G1) can be obtained.

[0114]

Chemical formula

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

[0116] In the synthetic scheme (c-1), it is possible to perform a Suzuki-Miyaura coupling reaction using a palladium catalyst, a Negishi coupling reaction using an organotin compound, a Kumada-Corriu coupling reaction using a Grignard reagent, a Heck coupling reaction using an organic zinc compound, a reaction using copper or a copper compound, etc. Details of the cases where these reactions are used can be referred to the description in the synthetic scheme (a-1). It is possible to do so. It is possible to do so. It is possible to do so. It is possible to do so.

[0117] ≪Synthesis method 4 of the organic compound represented by the general formula (G1)≫ The organic compound represented by the general formula (G1) can be synthesized using the synthetic scheme (d-1). It can be done.

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

[0119] [Chemical formula]

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

[0121] In the synthetic scheme (d-1), a backward Hartwig amination reaction using a palladium catalyst, an Ullmann reaction using copper or a copper compound, etc. can be carried out. The details when using these reactions can be referred to the description in the synthetic scheme (a-3).

[0122] <<Synthesis method 5 of the organic compound represented by the general formula (G1)>> ​​​The organic compound represented by the general formula (G1) can be synthesized using the synthetic scheme (e-1). This can be done.

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

[0124] [Chemical formula]

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

[0126] In the synthetic scheme (e-1), a backward Hartwig amination reaction using a palladium catalyst, a Ullmann reaction using copper or a copper compound, etc. can be carried out. For details when using these reactions, reference can be made to the description in the synthetic scheme (a-3). The details when using these reactions can be referred to the description in the synthetic scheme (a-3). Regarding the above, the synthesis method of the organic compound according to one aspect of the present invention has been described, but the present invention is not limited thereto.

[0127] The above has described the synthesis method of the organic compound according to one aspect of the present invention, but the present invention is not limited to this. It does not have to be synthesized, and it may be synthesized by other synthesis methods.

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

[0129] This embodiment can be appropriately combined with other embodiments. Also, in this specification, when a plurality of configuration examples are shown in one embodiment, the configuration examples can be appropriately combined.

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

[0131] [Configuration Example of Light-Emitting Device] ≪Basic Structure of Light-Emitting Device≫ FIGS. 1(A) to 1(D) show an example of a light-emitting device having an EL layer between a pair of electrodes.

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

[0133] Fig. 1(B) shows an example of the stacked structure of the EL layer 103. In the present embodiment, an example will be described in which the first electrode 1 01 functions as an anode and the second electrode 102 functions as a cathode. The EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked on the first electrode 101. The positive hole injection layer 111, the hole transport layer 112, the light-emitting layer 113, the electron transport layer 114, and the electron injection layer 115 may each have a single-layer structure or a stacked structure. When the first electrode 1 01 is a cathode and the second electrode 102 is an anode, the stacking order is reversed.

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

[0135] Fig. 1(C) shows a tandem structure light-emitting device having two EL layers (EL layers 103a, 103b) between a pair of electrodes. Fig. 1(D) shows a tandem structure light-emitting device having three EL layers (EL layers 103a , 103b, 103c). The EL layers 103a, 103b, 103c each have at least a light-emitting layer. Even when having a plurality of EL layers as in the tandem structures shown in Fig. 1(

[0136] C) and Fig. 1(D), the same stacked structure as the EL layer 103 shown in Fig. 1(B) can be applied to each EL layer. The EL layers 103a, 103b, 103c each have one or more of the hole injection layer 111, the hole transport layer 112 , the electron transport layer 114, and the electron injection layer 115. ​It is possible.

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

[0138] In addition, from the viewpoint of light extraction efficiency, the charge generation layer 104 preferably transmits visible light or near-infrared light (specifically, the transmittance of visible light or near-infrared light of the charge generation layer 104 is 40% or more). Also, the charge generation layer 104 can function even if its conductivity is lower than that of the first electrode 101 or the second electrode 102. In addition, from the viewpoint of light extraction efficiency, the charge generation layer 104 preferably transmits visible light or near-infrared light (specifically, the transmittance of visible light or near-infrared light of the charge generation layer 104 is 40% or more). Also, the charge generation layer 104 can function even if its conductivity is lower than that of the first electrode 101 or the second electrode 102. In addition, from the viewpoint of light extraction efficiency, the charge generation layer 104 preferably transmits visible light or near-infrared light (specifically, the transmittance of visible light or near-infrared light of the charge generation layer 104 is 40% or more). Also, the charge generation layer 104 can function even if its conductivity is lower than that of the first electrode 101 or the second electrode 102. In addition, from the viewpoint of light extraction efficiency, the charge generation layer 104 preferably transmits visible light or near-infrared light (specifically, the transmittance of visible light or near-infrared light of the charge generation layer 104 is 40% or more). Also, the charge generation layer 104 can function even if its conductivity is lower than that of the first electrode 101 or the second electrode 102.

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

[0140] Compared with a single-structure device, a tandem-structure light-emitting device has higher current efficiency and requires less current to emit light at the same luminance. Therefore, the life of the light-emitting device is long, and the reliability of the light-emitting device and electronic equipment can be improved. Compared with a single-structure device, a tandem-structure light-emitting device has higher current efficiency and requires less current to emit light at the same luminance. Therefore, the life of the light-emitting device is long, and the reliability of the light-emitting device and electronic equipment can be improved. Compared with a single-structure device, a tandem-structure light-emitting device has higher current efficiency and requires less current to emit light at the same luminance. Therefore, the life of the light-emitting device is long, and the reliability of the light-emitting device and electronic equipment can be improved.

[0141] The light-emitting layer 113 appropriately combines a light-emitting substance and a plurality of substances and has fluorescence of a desired wavelength. It can be configured to obtain photoluminescence or phosphorescence. Also, the light-emitting layer 113 may have a different laminated structure. In this case, different materials may be used for the light-emitting substances and other substances used in each of the laminated light-emitting layers. Also, the EL layers 103a, 103b, 103c shown in FIGS. 1(C) and 1(D) may be configured to emit light of different wavelengths. In this case as well, different materials may be used for the light-emitting substances and other substances used in each light-emitting layer. For example, in FIG. 1(C), by configuring the EL layer 103a to emit red and green light and the EL layer 103b to emit blue light, it is possible to obtain a light-emitting device that emits white light as a whole. Also, one light-emitting device may have a plurality of light-emitting layers or EL layers that exhibit the same color. For example, in FIG. 1(D), by configuring the EL layer 103a to emit first blue light, the EL layer 103b to emit yellow, yellow-green, or green light and red light, and the EL layer 103c to emit second blue light, it is possible to obtain a light-emitting device that emits white light as a whole. In the light-emitting device according to one aspect of the present invention, the light emitted from the EL layer may be resonated between a pair of electrodes to enhance the obtained light emission. For example, in FIG. 1(B), by using the first electrode 101 as a reflective electrode and the second electrode 102 as a semi-transmissive and semi-reflective electrode, a microcavity structure is formed, and the light emission obtained from the EL layer 103 can be enhanced.

[0142] By applying a microcavity structure to the light-emitting device, even if it has the same EL layer, different light emission characteristics can be obtained. For example, in FIG. 1(B), by using the first electrode 101 as a reflective electrode and the second electrode 102 as a semi-transmissive and semi-reflective electrode, a microcavity structure is formed, and the light emission obtained from the EL layer 103 can be enhanced. By applying a microcavity structure to the light-emitting device, even if it has the same EL layer, different

[0143] light emission characteristics can be obtained. Light of a specific wavelength (monochromatic light) can be extracted. Therefore, for obtaining different emission colors, it is not necessary to form different functional layers for each pixel (so-called painting). Thus, it is easy to achieve high definition. Also, it can be combined with a coloring layer (color filter). Furthermore, since it is possible to enhance the emission intensity in the forward direction of a specific wavelength, low power consumption can be achieved.

[0144] In addition, when the first electrode 101 of the light-emitting device is a reflective electrode composed of a laminated structure of a conductive film having reflectivity to visible light or near-infrared light and a conductive film having translucency to visible light or near-infrared light, optical adjustment can be performed by controlling the film thickness of the translucent conductive film. Specifically, with respect to the wavelength λ of the light obtained from the light-emitting layer 113, the electrode distance between the first electrode 101 and the second electrode 102 is preferably adjusted to be near mλ / 2

[0145] (where m is a natural number). Also, in order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, the optical distance from the first electrode 101 to the region (light-emitting region) where the desired light of the light-emitting layer 113 is obtained and the optical distance from the second electrode 102 to the region (light-emitting region) where the desired light of the light-emitting layer 113 is obtained are each preferably adjusted to be near (2m'+1)λ / 4 (where m' is a natural number). Here, the

[0146] light-emitting region refers to the recombination region of holes and electrons in the light-emitting layer 113.

[0147] However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 is strictly the total thickness from the reflection region in the first electrode 101 to the reflection region in the second electrode 102. This is possible. However, since it is difficult to accurately determine the reflection regions in the first electrode 101 and the second electrode 102, it is assumed that any position of the first electrode 101 and the second electrode 102 is the reflection region, and it is considered that the above-described effects can be sufficiently obtained. Also, the optical distance between the first electrode 101 and the light-emitting layer from which desired light can be obtained is strictly the optical distance between the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer from which desired light can be obtained. This is possible. However, since it is difficult to accurately determine the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer from which desired light can be obtained, any position of the first electrode 101 is assumed to be the reflection region, and any position of the light-emitting layer from which desired light can be obtained is assumed to be the light-emitting region, and it is considered that the above-described effects can be sufficiently obtained. At least one of the first electrode 101 and the second electrode 102 is an electrode having translucency with respect to visible light or near-infrared light. The transmittance of visible light or near-infrared light of the electrode having translucency with respect to visible light or near-infrared light is 40% or more. In addition, when the electrode having translucency with respect to visible light or near-infrared light is the above-described semi-transmissive / semi-reflective electrode, the reflectance of visible light or near-infrared light of the electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Also, the resistivity of these electrodes is preferably 1×10 Ωcm or less. If the first electrode 101 or the second electrode 102 has reflectivity with respect to visible light or near-infrared light,

[0148] At least one of the first electrode 101 and the second electrode 102 is an electrode having translucency with respect to visible light or near-infrared light. The transmittance of visible light or near-infrared light of the electrode having translucency with respect to visible light or near-infrared light is 40% or more. In addition, when the electrode having translucency with respect to visible light or near-infrared light is the above-described semi-transmissive / semi-reflective electrode, the reflectance of visible light or near-infrared light of the electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Also, the resistivity of these electrodes is preferably 1×10 Ωcm or less. When the electrode having translucency with respect to visible light or near-infrared light is the above-described semi-transmissive / semi-reflective electrode, the reflectance of visible light or near-infrared light of the electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Also, the resistivity of these electrodes is preferably 1×10 Ωcm or less. -2 Preferably, it is 1×10

[0149] If the first electrode 101 or the second electrode 102 has reflectivity with respect to visible light or near-infrared light, When it is the electrode to be formed (reflective electrode), the reflectance of visible light or near-infrared light of the reflective electrode is 40% or more and 100% or less, preferably 70% or more and 100% or less. Also, the resistivity of this electrode is preferably 1×10 -2 Ωcm or less.

[0150] ≪Specific Structure of Light-Emitting Device≫ Next, the specific structure of the light-emitting device will be described. Here, a light-emitting device having a structure shown in FIG. 1(B) will be used for the description.

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

[0152] In addition, when a light emitting device having a microcavity structure is to be manufactured, the first electrode 10 The first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a semi-transmissive and semi-reflective electrode. Therefore, the conductive material may be used singly or in a plurality of layers to form a single layer or a multilayer structure. The second electrode 102 can be formed by selecting a material in the same manner as described above after forming the EL layer 103. In addition, these electrodes are fabricated by sputtering or vacuum deposition. It is possible.

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

[0154] Materials with high hole injection properties include molybdenum oxide, vanadium oxide, and ruthenium oxide. transition metal oxides such as tungsten oxide and manganese oxide, phthalocyanine (abbreviation: Phthalocyanine compounds such as H2Pc and copper phthalocyanine (abbreviation: CuPc) are used. There can be.

[0155] As a material with high hole injection properties, 4,4',4''-tris(N,N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl) (N-phenylamino)triphenylamine (abbreviation: MTDATA), 4 ,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl Rue (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)- N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTP D), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino no]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl )-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3, 6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9- phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-( 9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: P CzPCN1), etc., aromatic amine compounds such as these can be used.

[0156] As materials with high hole injection properties, poly(N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'- [4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl ) methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphe nyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), etc. can be used . Or, poly(3,4-ethylenedioxythiophene) / poly(styrene sulfonic acid) (abbreviation: PEDOT / PSS), polyaniline / poly(styrenesulfone ic acid) (PAni / PSS), etc., polymer compounds with added acids, etc. can also be used.

[0157] As materials with high hole injection properties, hole transporting materials and acceptor materials (electron acceptor materials A composite material including the like can also be used. In this case, electrons are extracted from the hole transporting material by the acceptor material, and holes are generated in the hole injection layer 111, and the holes are injected into the light emitting layer 113 through the hole transport layer 112. Note that the hole injection layer 111 may be formed of a single layer made of a composite material including a hole transporting material and an acceptor material, or may be formed by laminating a hole transporting material and an acceptor material in separate layers. The hole injection layer 111 injects holes into the light emitting layer 113 through the hole transport layer 112 after electrons are extracted from the hole transporting material by the acceptor material, generating holes in the hole injection layer 111. Note that the hole injection layer 111 may be formed of a single layer made of a composite material including a hole transporting material and an acceptor material, or may be formed by laminating a hole transporting material and an acceptor material in separate layers. A composite material including the like can also be used. In this case, electrons are extracted from the hole transporting material by the acceptor material, and holes are generated in the hole injection layer 111, and the holes are injected into the light emitting layer 113 through the hole transport layer 112. Note that the hole injection layer 111 may be formed of a single layer made of a composite material including a hole transporting material and an acceptor material, or may be formed by laminating a hole transporting material and an acceptor material in separate layers.

[0158] The hole transport layer 112 is a layer that transports holes injected from the first electrode 101 by the hole injection layer 111 to the light emitting layer 113. The hole transport layer 112 is a layer including a hole transporting material. As the hole transporting material used for the hole transport layer 112, it is preferable to use a material having a highest occupied molecular orbital level (HOMO level) that is the same as or close to the HOMO level of the hole injection layer 111. The hole transport layer 112 is a layer that transports holes injected from the first electrode 101 by the hole injection layer 111 to the light emitting layer 113. The hole transport layer 112 is a layer including a hole transporting material. As the hole transporting material used for the hole transport layer 112, it is preferable to use a material having a highest occupied molecular orbital level (HOMO level) that is the same as or close to the HOMO level of the hole injection layer 111. Note that the hole injection layer 111 may be formed of a single layer made of a composite material including a hole transporting material and an acceptor material, or may be formed by laminating a hole transporting material and an acceptor material in separate layers. The hole injection layer 111 injects holes into the light emitting layer 113 through the hole transport layer 112 after electrons are extracted from the hole transporting material by the acceptor material, generating holes in the hole injection layer 111.

[0159] As the acceptor material used for the hole injection layer 111, metal oxides belonging to Groups 4 to 8 in the periodic table can be used. Specifically, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, rhenium oxide can be mentioned. Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives can be used. As compounds having an electron withdrawing group (halogen group or cyano group), 7,7,8,8 - tetracyano - 2,3,5,6 - tetrafluoroquinodimethane (abbreviation: F4 - TCNQ), chloranil, 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaaza As the acceptor material used for the hole injection layer 111, metal oxides belonging to Groups 4 to 8 in the periodic table can be used. Specifically, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, rhenium oxide can be mentioned. Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives can be used. As compounds having an electron withdrawing group (halogen group or cyano group), 7,7,8,8 - tetracyano - 2,3,5,6 - tetrafluoroquinodimethane (abbreviation: F4 - TCNQ), chloranil, 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaaza Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives can be used. As compounds having an electron withdrawing group (halogen group or cyano group), 7,7,8,8 - tetracyano - 2,3,5,6 - tetrafluoroquinodimethane (abbreviation: F4 - TCNQ), chloranil, 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaaza Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives can be used. As compounds having an electron withdrawing group (halogen group or cyano group), 7,7,8,8 - tetracyano - 2,3,5,6 - tetrafluoroquinodimethane (abbreviation: F4 - TCNQ), chloranil, 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaaza Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives can be used. As compounds having an electron withdrawing group (halogen group or cyano group), 7,7,8,8 - tetracyano - 2,3,5,6 - tetrafluoroquinodimethane (abbreviation: F4 - TCNQ), chloranil, 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaaza Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives can be used. As compounds having an electron withdrawing group (halogen group or cyano group), 7,7,8,8 - tetracyano - 2,3,5,6 - tetrafluoroquinodimethane (abbreviation: F4 - TCNQ), chloranil, 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaaza Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives can be used. As compounds having an electron withdrawing group (halogen group or cyano group), 7,7,8,8 - tetracyano - 2,3,5,6 - tetrafluoroquinodimethane (abbreviation: F4 - TCNQ), chloranil, 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaaza Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives can be used. As compounds having an electron withdrawing group (halogen group or cyano group), 7,7,8,8 - tetracyano - 2,3,5,6 - tetrafluoroquinodimethane (abbreviation: F4 - TCNQ), chloranil, 2,3,6,7,10,11 - hexacyano - 1,4,5,8,9,12 - hexaaza Zatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetra cyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), etc. can be mentioned. In particular, a compound in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of heteroatoms like HAT-CN is thermally stable and preferable. Also, a [3]radialene derivative having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) has a very high electron-accepting property, so it is preferable. Specifically, α,α’,α’’-1,2,3-cyclopropanetriylidene tris [4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α’ ,α’’-1,2,3-cyclopropanetriylidene tris[2,6-dichloro-3,5 -difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α’,α’ ’-1,2,3-cyclopropanetriylidene tris[2,3,4,5,6-pentafluoro benzeneacetonitrile], etc. can be mentioned.

[0160] As the hole-transporting material used for the hole injection layer 111 and the hole transport layer 112, a substance having a hole mobility of 10 -6 cm 2 / Vs or more is preferable. In addition, as long as it is a substance having higher hole transportability than electrons, other substances can also be used.

[0161] The light-emitting device of one aspect of the present invention preferably has an organic compound of one aspect of the present invention as the hole-transporting material used for one or both of the hole injection layer 111 and the hole transport layer 112. Also, since the organic compound of one aspect of the present invention has high electron blocking property, by using it for the hole transport layer 112, the light emission efficiency of the light-emitting device can be increased.

[0162] As the hole transporting material, π-electron excessive heteroaromatic compounds (such as carbazole derivatives, thiophene derivatives, furan derivatives, etc.) or aromatic amines (compounds having an aromatic amine skeleton) and other materials with high hole transporting properties are preferred.

[0163] As the carbazole derivative (compound having a carbazole skeleton), bicarbolyl derivatives (such as 3,3'-bicarbolyl derivatives), aromatic amines having a carbazolyl group, etc. can be mentioned. etc. can be mentioned.

[0164] As the bicarbolyl derivative (such as 3,3'-bicarbolyl derivative), specifically, 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9 '-bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carbazole, 9 ,9'-bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole , 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4-yl )-9H,9'H-3,3'-bicarbolyl (abbreviation: mBPCCBP), 9-(2-naph thyl)-9'-phenyl-9H,9'H-3,3'-bicarbolyl (abbreviation: βNCC P), etc. can be mentioned.

[0165] As the aromatic amine having a carbazolyl group, specifically, 4-phenyl-4'-(9 -phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBA1B P), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl )-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1, (1'-Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBB iF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-( 9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAN B), 4,4'-bis(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9 -phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N,N' -bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene-1, 3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N',N' '-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl- 9H-carbazol-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBAF ), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl spiro-9,9'-bifluorene-2-amine (abbreviation: PCBASF), PCzPC A1, PCzPCA2, PCzPCN1, 3-[N-(4-diphenylaminophenyl) -N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6 -bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenyl carbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylaminof , 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenyl carbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenyl carbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenyl -N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzT PN2), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino] Spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4-(9H-carbazol yl-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1B P), N,N'-bis[4-(carbazol-9-yl)phenyl]-N,N'-diphe nyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), 4,4' ,4''-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA) and so on can be mentioned.

[0166] As the carbazole derivatives, in addition to the above, 3-[4-(9-phenanthryl)-phe nyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3-[4-(1-na phthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 1,3 -bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl lu)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9- phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazolyl lu)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anth racenyl)phenyl]-9H-carbazole (abbreviation: CzPA) and so on can be mentioned.

[0167] As for the thiophene derivatives (compounds having a thiophene skeleton) and furan derivatives (compounds having a furan skeleton), specifically, 4,4',4''-(benzene-1,3,5-tri yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1B Iru) tri (dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl- 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene ne (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9 -yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), etc. Any compound having a thiophene skeleton, 4,4',4''-(benzene-1,3,5-tri yl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-f enyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: m mDBFFLBi-II), etc. can be mentioned.

[0168] Specific examples of the aromatic amine include 4,4'-bis[N-(1-naphthyl)-N-phe nylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-meth ylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl )-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9- phenylfluorene-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phe nyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: mBP AFLP), N-(9,9-dimethyl-9H-fluorene-2-yl)-N-{9,9- dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluorene-2- yl)amino]-9H-fluorene-7-yl}phenylamine (abbreviation: DFLADFL )、N-(9,9-dimethyl-2-diphenylamino-9H-fluorene-7-yl)di Phenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N -phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 2,7-bis [N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'- bifluorene (abbreviation: DPA2SF), 4,4',4''-tris[N-(1-naphthyl )-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), TDATA , m-MTDATA, N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenyl enediamine (abbreviation: DTDPPA), DPAB, DNTPD, DPA3B, etc. are exemplified.

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

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

[0171] <Light-emitting layer> The light-emitting layer 113 is a layer containing a light-emitting substance. The light-emitting layer 113 can have one or more kinds of light-emitting substances. As the light-emitting substance, substances exhibiting light-emitting colors such as blue, purple, blue-violet, green, yellow-green, yellow, orange, and red can be appropriately used. Also, as the light-emitting substance, a substance emitting near-infrared light can be used. Further, by using different light-emitting substances in a plurality of light-emitting layers, a configuration exhibiting different light-emitting colors (for example, white light obtained by combining light-emitting colors in a complementary color relationship) can be obtained. Furthermore, one light-emitting layer may have different light-emitting substances. ​​​​​​​​

[0172] In addition to the light-emitting substance (guest material), the light-emitting layer 113 preferably contains one or more organic compounds (host materials, assist materials, etc.). One or more organic compounds may be used to include one or both of the hole-transporting material and the electron-transporting material described in this embodiment. Further, a bipolar material may be used as the one or more organic compounds. When a hole-transporting material is used in the light-emitting layer 113, it is preferable to use an organic compound of a type similar to that of the present invention as the hole-transporting material. There is no particular limitation on the light-emitting substance that can be used in the light-emitting layer 113, and a light-emitting substance that converts singlet excitation energy into light emission in the visible light region or near-infrared light region, or a light-emitting substance that converts triplet excitation energy into light emission in the visible light region or near-infrared light region can be used. Examples of the light-emitting substance that converts singlet excitation energy into light emission include substances that emit fluorescence (fluorescent materials), such as pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives, etc. In particular, pyrene derivatives are preferable because of their high photoluminescence quantum yield. Specific examples of the pyrene derivative include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,

[0173] When a hole-transporting material is used in the light-emitting layer 113, it is preferable to use an organic compound of a type similar to that of the present invention as the hole-transporting material.

[0174] There is no particular limitation on the light-emitting substance that can be used in the light-emitting layer 113, and a light-emitting substance that converts singlet excitation energy into light emission in the visible light region or near-infrared light region, or a light-emitting substance that converts triplet excitation energy into light emission in the visible light region or near-infrared light region can be used. Examples of the light-emitting substance that converts singlet excitation energy into light emission include substances that emit fluorescence (fluorescent materials), such as pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives, etc. In particular, pyrene derivatives are preferable because of their high photoluminescence quantum yield. Specific examples of the pyrene derivative include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,

[0175] Examples of the light-emitting substance that converts singlet excitation energy into light emission include substances that emit fluorescence (fluorescent materials), such as pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives, etc. In particular, pyrene derivatives are preferable because of their high photoluminescence quantum yield. Specific examples of the pyrene derivative include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N, ​ N'-Diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bi s(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbre viation: 1,6FrAPrn), N,N'-bis(dibenzothiophen-2-yl)-N,N '-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-( pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]fura n)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-di yl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis (6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbre viation: 1,6BnfAPrn-03), etc. can be mentioned.

[0176] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2, 2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl- 9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2B Py), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N' -diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carb azole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-di (Phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-di phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbaz -ol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4 ’-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4’-(9- phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA ), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP ), N,N’’-(2-tert-butylanthracene-9,10-diyl-di-4,1- phenylene)bis[N,N’,N’-triphenyl-1,4-phenylenediamine](abbre viation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-a ntryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N -[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N’,N’-tri phenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), etc. can be used .

[0177] In addition, as a luminescent substance that converts triplet excitation energy into luminescence, for example, substances that emit phosphorescence (phosphorescent materials) and thermally activated delayed fluorescence (Thermally Ac tivated Delayed Fluorescence: TADF) materials can be mentioned . Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), rare earth metal complexes, etc.

[0178] ​They exhibit different emission colors (emission peaks) for each substance, and are appropriately selected and used as needed. Select and use as appropriate.

[0179] Examples of the phosphorescent material that exhibits blue or green and has a peak wavelength of the emission spectrum in the range of 450 nm or more and 570 nm or less include the following substances. Examples of the phosphorescent material that exhibits blue or green and has a peak wavelength of the emission spectrum in the range of 450 nm or more and 570 nm or less include the following substances.

[0180] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl) )-4H-1,2,4-triazol-3-yl-κN 2 phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl yl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrp tz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl yl-4H-1,2,4-triazolato]iridium(III) (abbreviation: Ir(iPr5b tz)3]), and other organometallic complexes having a 4H-triazole skeleton, tris[3-meth yl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato] 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]) and other organometallic complexes having a 1H-triazole skeleton, fac-tris[1-(2,6-diisopropylphenyl)-2-phen yl-2H-benzimidazolato]iridium(III) (abbreviation: [Ir(dipi [Ir(iPrpmi)3] ), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]furan [Phenanthridine]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3] Organometallic complexes with imidazole skeletons such as bis[2-(4',6'-difluoro (phenyl)pyridinato-N,C 2’ ]Iridium(III) tetrakis(1-pyrazolyl) FIr6, bis[2-(4',6'-difluorophenyl)pyridine Ginat-N,C 2’ ]Iridium(III) picolinate (abbreviation: FIrpic), bis {2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’} Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium( III) Acetylacetonate (abbreviation: FIr(acac)) has an electron-withdrawing group Examples of such a complex include an organometallic complex having a phenylpyridine derivative as a ligand.

[0181] It has a green or yellow color and the peak wavelength of the emission spectrum is between 495 nm and 590 nm. Some phosphorescent materials include the following:

[0182] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)i Lithium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bi Tris(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(m ppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(a cac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl pyrimidinato]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-dimethyl-2-[6-(2,6-dimethyl phenyl)-4-pyrimidinyl-κN 3 phenyl-κC}iridium(III) (abbreviation : [Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2( acac)]), organometallic iridium complexes having a pyrimidine skeleton such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III)( abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5 -isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), organometallic iridium complexes having a pyrazine skeleton such as tris(2-phenylpyridinato-N,C )iridium(III) 2’ (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2’ )iridi U(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), vi S(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [I r(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(II I)(abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato- N,C 2’ ) iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(a cac)]), [2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]bis 2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir( ppy)2(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC] [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC] such as Organometallic iridium complexes having a pyridine skeleton, bis(2,4-diphenyl-1,3-o xazolato-N,C 2’ ) iridium(III) acetylacetonate (abbreviation: [Ir( dpo)2(acac)]), bis{2-[4’-(perfluorophenyl)phenyl] pyridinato-N,C 2’} iridium(III) acetylacetonate (abbreviation: [Ir( p-PF-ph)2(acac)]), bis(2-phenylbenzothiazolato-N,C 2 ’ ) iridium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac) ) and other organometallic complexes, tris(acetylacetonato)(monophenanthroline) Rare earth metal complexes such as terbium(III) (abbreviation: [Tb(acac)3(Phen)]) are included.

[0183] Phosphorescent materials that exhibit yellow or red and have a peak wavelength of the emission spectrum in the range of 570 nm or more and 750 nm or less include the following substances.

[0184] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis [4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di (naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III )(abbreviation: [Ir(d1npm)2(dpm)]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]) and other organometallic complexes having a pyrimidine skeleton, (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac )]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), bis{4,6-dimethyl -2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ O,O’)iridium(III) (abbreviation: [Ir(dmdppr-P)2(dibm)]), bis{4,6 2 ​​​​​​​​​​-Dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-di methylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetra methyl-3,5-heptanedionato-κ 2 O,O’)iridium(III)(abbreviation:[I r(dmdppr-dmCP)2(dpm)]), (acetylacetonato)bis[2-me thyl-3-phenylquinoxalinato-N,C 2’ iridium(III)(abbreviation:[Ir (mpq)2(acac)]), (acetylacetonato)bis(2,3-diphenylquin oxalinato-N,C 2’ )iridium(III)(abbreviation:[Ir(dpq)2(acac )]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxa linato]iridium(III)(abbreviation:[Ir(Fdpq)2(acac)]), bis{ 4,6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-di methylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetra methyl-3,5-heptanedionato-κ 2 O,O’)iridium(III)(abbreviation:[I r(dmdppr-m5CP)2(dpm)]) and other organometallic complexes having a pyrazine skeleton, tris(1-phenylisoquinolinato-N,C 2’ )iridium(III)(abbre viation:[Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ )irid ium(III)acetylacetonate(abbreviation:[Ir(piq)2(acac)]), bi s[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pen tanedionato-κ 2Organic compounds having a pyridine skeleton such as iridium(III) (O,O’) metal complexes, platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H- porphyrin platinum(II) (abbreviation: [PtOEP]), tris(1,3 -diphenyl-1,3-propanedionato)(monophenanthroline)europium(III (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-thenoyl)- 3,3,3-trifluoroacetonato](monophenanthroline)europium(III )(abbreviation: [Eu(TTA)3(Phen)]) and other rare earth metal complexes.

[0185] As the organic compound (host material, assist material, etc.) used in the light-emitting layer 113, a substance having an energy gap larger than the energy gap of the light-emitting substance can be selected and used alone or in combination of two or more. When the light-emitting substance used in the light-emitting layer 113 is a fluorescent material, it is preferable to use an organic compound having a large energy level of the singlet excited state and a small energy level of the triplet excited state as the organic compound used in combination with the light-emitting substance. Although some overlap with the above specific examples, specific examples of the organic compound are shown below from the viewpoint of a preferable combination with the light-emitting substance (fluorescent material, phosphorescent material).

[0186] When the light-emitting substance is a fluorescent material, examples of the organic compound that can be used in combination with the light-emitting substance include condensed polycyclic aromatic compounds such as anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives. When the light-emitting substance is a fluorescent material, examples of the organic compound that can be used in combination with the light-emitting substance include condensed polycyclic aromatic compounds such as anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives. When the light-emitting substance is a fluorescent material, examples of the organic compound that can be used in combination with the light-emitting substance include condensed polycyclic aromatic compounds such as anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives.

[0187] Although some overlap with the above specific examples, specific examples of the organic compound are shown below from the viewpoint of a preferable combination with the light-emitting substance (fluorescent material, phosphorescent material). Although some overlap with the above specific examples, specific examples of the organic compound are shown below from the viewpoint of a preferable combination with the light-emitting substance (fluorescent material, phosphorescent material).

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

[0189] Specific examples of the organic compound (host material) used in combination with the fluorescent material include 9-phenyl -3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole ( abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl phenyl]-9H-carbazole (abbreviation: DPCzPA), PCPN, 9,10-di phenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10 -phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: C zA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: D PhPA), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-a ntryl)triphenylamine (abbreviation: YGAPA), N,9-diphenyl-N-[4- (10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbre viation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anth ryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA ), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carb azole-3-amine (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-dif enylchrysene, N,N,N',N',N'',N'',N''',N''' - octaf enyl dibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC 1), CzPA, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-di benzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-di Phenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation : 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoro rene-9-yl)biphenyl-4'-yl}anthracene (abbreviation: FLPPA), 9,10 -bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di (2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation : BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation : DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), 5,1 2-diphenyltetracene, 5,12-bis(biphenyl-2-yl)tetracene, etc. are listed.

[0190] When the light-emitting substance is a phosphorescent material, as the organic compound used in combination with the light-emitting substance, an organic compound having a triplet excitation energy greater than the triplet excitation energy (energy difference between the ground state and the triplet excited state) of the light-emitting substance may be selected. When a plurality of organic compounds (for example, a first host material and a second host material (or assist material), etc.) are used in combination with the light-emitting substance to form an exciplex, it is preferable to mix these

[0191] plurality of organic compounds with a phosphorescent material (especially an organometallic complex). By adopting such a configuration, Ex which is energy transfer from the exciplex to the light-emitting substance can be achieved.

[0192] can be achieved. Using TET (Exciplex-Triplet Energy Transfer) efficient emission can be obtained. As for the combination of a plurality of organic compounds, those in which an exciplex is likely to be formed are preferable, and it is particularly preferable to combine a compound that easily receives holes (hole-transporting material) and a compound that easily receives electrons (electron-transporting material). Note that the organic compound of one aspect of the present invention shown in Embodiment 1 is suitable as a compound that easily receives holes. Regarding specific examples of the hole-transporting material and the electron-transporting material, the materials shown in this embodiment can be used. With this configuration, high efficiency, low-voltage driving, and long life of the light-emitting device can be realized simultaneously. When the light-emitting substance is a phosphorescent material, organic compounds that can be used in combination with the light-emitting substance include aromatic amines, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, zinc- and aluminum-based metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline derivatives, and the like. Among the above, specific examples of aromatic amines (compounds having an aromatic amine skeleton), carbazole derivatives, dibenzothiophene derivatives (thiophene derivatives), and dibenzofuran derivatives (furan derivatives), which are organic compounds with high hole-transporting properties, are the same as the specific examples of the hole-transporting materials shown above.

[0193]

[0194]

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

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

[0197] Specific examples of organic compounds with high electron-transporting properties, such as oxadiazole derivatives, triazole derivatives, ben zimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, phenan throline derivatives, include 2-(4-biphenylyl)-5-(4-tert-but ylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5- (p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole- 2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-biphenylyl (Ru)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl )-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ) , 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H- benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl )phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II ), 4,4’-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: B zOs, bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP ), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthro line (abbreviation: NBPhen), 2-[3-(dibenzothiophen-4-yl)phenyl dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3’ -(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxa line (abbreviation: 2mDBTBPDBq-II), 2-[3’-(9H-carbazol-9 -yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBP DBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(di benzo[b]thiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7m DBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl] dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II) etc. are mentioned .

[0198] Heterocyclic compounds having a diazine skeleton, heterocyclic compounds having a triazine skeleton, and heterocyclic compounds having a pyridine skeleton, which are organic compounds with high electron transporting properties. Specific examples include 4,6 -bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn P2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation : 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-f enyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl} -4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3 -(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phe nyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 2- 3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3 -yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 2 -[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobi (9H-fluorene)-2-yl]-1,3,5-triazine (abbreviation: BP-SFTzn ), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTz n), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPT ) zn-02), 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine ne (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]be nzene (abbreviation: TmPyPB), etc. can be mentioned.

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

[0200] A TADF material is a material that can undergo triplet-triplet annihilation upconversion (reverse intersystem crossing) from a triplet excited state to a singlet excited state by a small amount of thermal energy, and efficiently emit light (fluorescence) from the singlet excited state. Also, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to light emission that has a spectrum similar to that of normal fluorescence but has a significantly longer lifetime. The lifetime is 10 seconds or more, preferably 10 seconds or more. As TADF materials, for example, fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin can be mentioned. Also, magnesium (Mg), zinc (Zn), cadmium -6 seconds or more, preferably 10 -3 seconds or more.

[0201] As TADF materials, for example, fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin can be mentioned. Also, magnesium (Mg), zinc (Zn), cadmium Cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd), etc., and metal-containing porphyrins can be mentioned. As the metal-containing porphyrins, for example, protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)) , mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (abbreviation: SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III- 4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(OEP)) , etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), octaethylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP), etc. can be mentioned.

[0202] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo [2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ) , PCCzPTzn, 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3- 4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5 -diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9- dimethyl-9H-acridin-10-yl)-9H-xanthene-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'-anthracen]-10'-one (abbreviation: ACRSA), etc. of π electrons It is possible to use a heterocyclic compound having an electron-rich heterocyclic aromatic ring and an electron-deficient heterocyclic aromatic ring. In addition, a substance in which an electron-rich heterocyclic aromatic ring and an electron-deficient heterocyclic aromatic ring are directly bonded has both the donor property of the electron-rich heterocyclic aromatic ring and the acceptor property of the electron-deficient heterocyclic aromatic ring becomes stronger, and the energy difference between the singlet excited state and the triplet excited state becomes smaller, which is particularly preferable.

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

[0204] Also, the above materials can be used to form the light-emitting layer 113 by combining with a low-molecular material or a high-molecular material. For film formation, known methods (such as vapor deposition method, coating method, printing method, etc.) ) can be appropriately used.

[0205] <Electron transport layer> The electron transport layer 114 is a layer that transports electrons injected from the second electrode 102 to the light-emitting layer 113 by the electron injection layer 115. In addition, the electron transport layer 114 is a layer containing an electron transport material. The electron transport material used for the electron transport layer 114 is 1×10 -6 cm 2 / Vs or more Substances having an electron mobility are preferred. In addition, any substance having higher electron transportability than holes can also be used other than these.

[0206] Examples of the electron transport material include metal complexes having a quinoline skeleton and those having a benzoquinoline skeleton ​In addition to metal complexes, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, etc. , oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives , thiazole derivatives, phenanthroline derivatives, quinoline derivatives having a quinoline ligand , benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, and other nitrogen-containing heteroaromatic compounds including π-electron-deficient heteroaromatic compounds such as highly electron-transporting materials can be used.

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

[0208] <Electron injection layer> The electron injection layer 115 is a layer containing a material with high electron injection properties. In the electron injection layer 115, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiO x ) and other alkali metals, alkaline earth metals, or their compounds can be used. In addition, rare earth metal compounds such as erbium fluoride (ErF3) can be used. Also, electride may be used in the electron injection layer 115. As electride, for example, substances obtained by adding electrons to a mixed oxide of calcium and aluminum at a high concentration can be mentioned. Note that the substances constituting the above-described electron transport layer 114 can also be used.

[0209] In addition, a composite material containing an electron-transporting material and a donor material (electron-donating material) may be used for the electron injection layer 115. Such a composite material donates electrons to an organic compound by an electron donor ​Since it occurs, it is excellent in electron injection property and electron transport property. In this case, as the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, the electron transport material (such as a metal complex or a heteroaromatic compound) used for the electron transport layer 114 described above can be used. As the electron donor, any substance that shows electron-donating property to the organic compound is acceptable. Specifically, an alkali metal, an alkaline earth metal, or a rare earth metal is preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Further, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, barium oxide, etc. Also, a Lewis salt such as magnesium oxide can be used. Further, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

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

[0211] The charge generation layer 104 may be composed of a hole-transporting material and an acceptor material (electron-accepting material), or may be composed of an electron-transporting material and a donor material. By forming the charge generation layer 104 having such a configuration, an increase in the driving voltage when the EL layer is laminated can be suppressed.

[0212] The hole-transporting material, the acceptor material, the electron-transporting material, and the donor material are each The above materials can be used.

[0213] In addition, for the fabrication of the light-emitting device shown in this embodiment, vacuum processes such as vapor deposition and solution processes such as spin coating and inkjet printing can be used. When using the vapor deposition method, physical vapor deposition (PVD) methods such as sputtering, ion plating, ion beam vapor deposition, molecular beam vapor deposition, and vacuum vapor deposition, or chemical vapor deposition (CVD) methods can be used. In particular, for the functional layers (hole injection layer, hole transport layer, light-emitting layer, electron transport layer , electron injection layer) and charge generation layer included in the EL layer, they can be formed by methods such as vapor deposition (such as vacuum vapor deposition), coating (dip coating, die coating, bar coating, spin coating, spray coating, etc.), printing methods (inkjet printing, screen (stencil printing) method, offset (lithography) method, flexo (letterpress) method, gravure method, microcontact method, etc.).

[0214] The materials of the functional layers and charge generation layer constituting the EL layer 103 are not limited to the above materials respectively. For example, as the materials of the functional layers, polymer compounds (oligomers, dendrimers, polymers, etc.), medium molecular compounds (compounds in the intermediate region between low molecules and high molecules: molecular weight 400 to 400 0), inorganic compounds (quantum dot materials, etc.) can be used. As the quantum dot materials, colloidal quantum dot materials, alloy-type quantum dot materials, core-shell-type quantum dot materials , core-type quantum dot materials, etc. can be used.

[0215] This embodiment can be appropriately combined with other embodiments.

[0216] (Embodiment 3) In this embodiment, a light-emitting device according to one aspect of the present invention will be described with reference to FIGS. 2 to 5.

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

[0218] The light-emitting device shown in FIG. 2(B) includes a substrate 490a, a substrate 490b, a conductive layer 406, a conductive layer 41 6, an insulating layer 405, an organic EL device 450 (a first electrode 401, an EL layer 402, and a second electrode 403), and an adhesive layer 407. The organic EL device 450 can also be referred to as a light-emitting element, an organic EL element, a light-emitting device, etc. The EL layer 402 preferably has an organic compound according to one aspect of the present invention as shown in Embodiment 1. For example, among the materials for the hole injection layer , the hole transport layer, and the host material of the light-emitting layer, it is preferable to have the organic compound as at least one of them.

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

[0220] The ends of the first electrode 401, the conductive layer 406, and the conductive layer 416 are covered with the insulating layer 405. The conductive layer 406 is electrically connected to the first electrode 401, and the conductive layer 416 is electrically connected to the second electrode 403. ​​​​​Electrically connect. The conductive layer 406 covered by the insulating layer 405 via the first electrode 401 is Function as an auxiliary wiring and is electrically connected to the first electrode 401. When the organic EL device 450 has an auxiliary wiring that is electrically connected to the electrode of, it is possible to suppress the voltage drop caused by the resistance of the electrode, which is preferable. The conductive layer 406 may be provided on the first electrode 401. Also, it may have an auxiliary wiring that is electrically connected to the second electrode 403 on the insulating layer 405 or the like.

[0221] For the substrates 490a and 490b, glass, quartz, ceramic, sapphire , an organic resin, or the like can be used. Using a flexible material for the substrates 490a and 490b can enhance the flexibility of the display device.

[0222] On the light-emitting surface of the light-emitting device, a light extraction structure for enhancing the light extraction efficiency, an antistatic film for suppressing the adhesion of dust, a water-repellent film for making it difficult for dirt to adhere, a hard coat film for suppressing the generation of scratches during use, a shock-absorbing layer, or the like may be arranged.

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

[0224] As the adhesive layer 407, various curable adhesives such as photocurable adhesives such as ultraviolet curable type, reaction curable adhesives, thermosetting adhesives, and anaerobic adhesives can be used. These adhesives include epoxy resin, acrylic resin, silicone resin, phenolic resin, polyimide resin, ​​​​Imide resin, PVC (polyvinyl chloride) resin, PVB (polyvinyl butyral) resin , EVA (ethylene vinyl acetate) resin, etc. may be mentioned. In particular, materials with low moisture permeability such as epoxy resin are preferred. Also, a two-component mixed resin may be used. Also, an adhesive sheet etc. may be used.

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

[0226] The barrier layer 490c shown in Fig. 2(C) has a substrate 420, an adhesive layer 422, and a highly barrier insulating layer 424.

[0227] In the light-emitting device shown in Fig. 2(C), an organic EL device 450 is disposed between the highly barrier insulating layer 424 and the barrier layer 423. Therefore, even if a resin film with relatively low waterproofness is used for the substrates 420 and 490b, it is possible to suppress the ingress of impurities such as water into the organic EL device and the reduction of its lifespan.

[0228] The substrates 420 and 490b are each, for example, a polyester resin such as polyethylene terephthalate (P ET), polyethylene naphthalate (PEN), a polyacrylonitrile resin, an acrylic resin, a polyimide resin, a polymethyl methacrylate resin, a polycarbonate (PC) resin, a polyethersulfone (PES) resin, a polyamide resin (nylon , aramid, etc.), a polysiloxane resin, a cycloolefin resin, a polystyrene resin, a poly amideimide resin, a polyurethane resin, a polyvinyl chloride resin, a polyvinylidene chloride resin, ​​​​Polypropylene resin, polytetrafluoroethylene (PTFE) resin, ABS resin, cell ulose nanofibers, etc. can be used. For the substrates 420 and 490b, glass with a thickness that has flexibility may be used.

[0229] As the highly barrier insulating layer 424, it is preferable to use an inorganic insulating film. As the inorganic insulating film, for example, a silicon nitride film, a silicon oxynitride film, a silicon oxide film, a silicon nitride oxide film, an aluminum oxide film, an aluminum nitride film, etc. can be used. Also, a hafnium oxide film, a yttrium oxide film, a zirconium oxide film, a gallium oxide film, a tantalum oxide film, a magnesium oxide film, a lanthanum oxide film, a cerium oxide film, and a neodymium oxide film, etc. may be used. Also, the above insulating films may be laminated and used in two or more layers.

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

[0231] The highly barrier insulating layer 424 and the organic EL device 450 can be directly formed on the flexible substrate 420. In this case, the adhesive layer 422 is unnecessary. Also, the insulating layer 4 ​​​​​​​​​​​​After the 24 and the organic EL device 450 are formed on a rigid substrate via a release layer, they can be transferred to the substrate 42 0. For example, by applying heat, force, laser light, etc. to the release layer, after peeling the insulating layer 424 and the organic EL device 450 from the rigid substrate, the substrate 420 may be transferred by bonding the substrate 420 using the adhesive layer 422. As the release layer, for example, a laminated structure of an inorganic film including a tungsten film and a silicon oxide film, a polyimide organic resin film such as etc. can be used. When using a rigid substrate, compared with a resin substrate, etc., since the insulating layer 424 can be formed by applying a high temperature, the insulating layer 424 can be made into a dense and extremely high-barrier insulating film.

[0232] [Configuration Example 2 of Light Emitting Device] Fig. 3(A) shows a cross-sectional view of a light emitting device. The light emitting device shown in Fig. 3(A) is an active matrix type light emitting device in which a transistor and a light emitting device are electrically connected.

[0233] The light emitting device shown in Fig. 3(A) includes a substrate 201, a transistor 210, a light emitting device 203R , a light emitting device 203G, a light emitting device 203B, a color filter 206R, a color fil ter 206G, a color filter 206B, a substrate 205, etc.

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

[0235] The transistor 210 and the light emitting devices 203R, 203G, 203B are on the substrate 201 It is sealed in a space 207 surrounded by, for example, a substrate 205 and an adhesive layer 208. Space 2 07 can have, for example, a configuration filled with a reduced-pressure atmosphere, an inert atmosphere, or a resin .

[0236] In the light-emitting device shown in Fig. 3(A), one pixel has a red sub-pixel (R), a green sub-pixel (G) , and a blue sub-pixel (B).

[0237] The light-emitting device according to one aspect of the present invention has a plurality of pixels arranged in a matrix. One pixel has one or more sub-pixels. One sub-pixel has one light-emitting device. For example , a pixel can have a configuration with three sub-pixels (three colors of R, G, B, or three colors of yellow (Y), cyan (C) , and magenta (M), etc.), or a configuration with four sub-pixels (four colors of R, G , B, white (W), or four colors of R, G, B, Y, etc.).

[0238] Fig. 3(B) shows the detailed configuration of the light-emitting device 203R, the light-emitting device 203G, and the light-emitting device 20 3B. The light-emitting devices 203R, 203G, and 203B have a common EL layer 213, and have a microcavity structure in which the optical distance between the electrodes of each light-emitting device is adjusted according to the emission color of each light-emitting device. The EL layer 213 preferably has an organic compound according to one aspect of the present invention as shown in Embodiment 1. For example, among the material of the hole injection layer , the material of the hole transport layer, and the host material of the light-emitting layer, it is preferable to have the organic compound as at least one of them .

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

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

[0241] As shown in FIG. 3(B), in the light-emitting device 203R, the conductive layer 212R is formed on the first electrode 2 11, and in the light-emitting device 203G, the conductive layer 212G is formed on the first electrode 211, thereby enabling optical adjustment. Further, in the light-emitting device 203B, a conductive layer having a thickness different from those of the conductive layer 212R and the conductive layer 212G may be formed on the first electrode 211 to adjust the optical distance 220B. As shown in FIG. 3(A), the ends of the first electrode 211, the conductive layer 212R, and the conductive layer 212G are covered with the insulating layer 204.

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

[0243] In the red sub-pixel (R), light emitted from the light-emitting device 203R is emitted through the red color filter 2 06R. As shown in FIG. 3(A), the position overlapping the light-emitting device 203R By providing a color filter 206R that allows only the red wavelength range to pass through, red light emission can be obtained from the light emitting device 203R.

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

[0245] Note that a black matrix 209 (which can also be referred to as a black layer) may be provided on the substrate 205. At this time, it is preferable that the end portion of the color filter overlaps with the black matrix 209. Furthermore, the color filters of each color and the black matrix 209 may be covered with an overcoat layer that transmits visible light.

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

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

[0248] For example, when it is desired to increase the intensity of blue light, such as when the light emitted from the light emitting device 203W is white light with a low color temperature, as shown in Fig. 3(C), in the light emitting device 203W It is preferable that the optical distance is made equal to the optical distance 220B in the light-emitting device 203B. Thereby, the light obtained from the light-emitting device 203W can be made closer to white light having a desired color temperature.

[0249] In FIG. 3(A), an example is shown in which a common EL layer 213 is used for the light-emitting devices included in the sub-pixels of each color. However, as shown in FIG. 4(A), different EL layers may be used for the light-emitting devices included in the sub-pixels of each color. Also in FIG. 4(A), the above-described microcavity structure can be applied in the same manner.

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

[0251] In FIG. 3(A), a top emission type light-emitting device is shown. However, as shown in FIG. 4(B), a structure (bottom emission type) in which light is taken out to the side of the substrate 201 on which the transistor 210 is formed is also an aspect of the present invention.

[0252] In a bottom emission type light-emitting device, it is preferable to provide color filters of each color between the substrate 201 and the light-emitting device. In FIG. 4(B), on the substrate 201, a transistor 21 ​​​​​​​​Form 0, form an insulating layer 202a on the transistor 210, and form a color - filter 206R, 206G, 206B on the insulating layer 202a, and form an insulating layer 202b on the color filters 206R, 206G 206B, and form light-emitting devices 203R, 2 03G, 203B is shown as an example.

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

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

[0255] [Configuration Example 3 of Light-Emitting Device] The light-emitting device according to one aspect of the present invention can be a passive matrix type or an active matrix type. The active matrix type light-emitting device will be described with reference to FIG. 5.

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

[0257] The active matrix type light-emitting device shown in FIGS. 5(A) and 5(B) includes a pixel portion 302, a circuit portion 303, a circuit portion 304a, and a circuit portion 304b. The circuit portion 303, the circuit portion 304a, and the circuit portion 304b can each function as a scanning line driving circuit (gate driver) or a signal line driving circuit (source driver).

[0258] The circuit portion 303, the circuit portion 304a, and the circuit portion 304b can each function as a scanning line driving circuit (gate driver) or a signal line driving circuit (source driver). Alternatively, an external gate driver or source driver and the pixel portion 302 can be electrically connected. It may be a circuit to be connected.

[0259] On the first substrate 301, a routing wiring 307 is provided. The routing wiring 307 is electrically connected to an FPC 308 which is an external input terminal. The FPC 308 transmits an external signal (for example, a video signal, a clock signal, a start signal, a reset signal, etc.) and a potential to the circuit section 303, the circuit section 304a, and the circuit section 304b. Further, a printed wiring board (PWB) may be attached to the FPC 308. The configuration shown in FIGS. 5(A) and 5(B) can also be said to be a light-emitting module having a light-emitting device (or a light-emitting apparatus) and an FPC.

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

[0261] The circuit section 303 includes a plurality of transistors including a transistor 309, a transistor 310, etc. The circuit section 303 may be formed of a circuit including a unipolar (either N-type or P-type only) transistor, or may be formed of a CMOS circuit including an N-type transistor and a P-type transistor. Further, it may be configured to have a drive circuit externally.

[0262] The structure of the transistor included in the light-emitting device of this embodiment is not particularly limited. For example, a p-type transistor, a staggered transistor, an inverse staggered transistor, etc. can be used. Moreover, either a top gate type or a bottom gate type transistor structure may be used. Alternatively, gates may be provided above and below the semiconductor layer in which the channel is formed. There is also no particular limitation on the crystallinity of the semiconductor material used for the transistor, and any of an amorphous semiconductor, a semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or a semiconductor having a crystal region in part) may be used. Using a semiconductor having crystallinity is preferable because deterioration of transistor characteristics can be suppressed. The semiconductor layer of the transistor preferably has a metal oxide (also referred to as an oxide semiconductor). Alternatively, the semiconductor layer of the transistor may have silicon. Examples of silicon include amorphous silicon, crystalline silicon (such as low-temperature polysilicon, single crystal silicon, etc.).

[0263] The semiconductor layer preferably has indium, one or more kinds (M) selected from gallium, aluminum, silicon, boron, yttrium, tin, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium, and zinc. In particular, M is preferably one or more kinds selected from aluminum, gallium, yttrium, and tin.

[0264]

[0265]

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

[0267] When the semiconductor layer is an In-M-Zn oxide, the sputtering target used to form the In-M-Zn oxide preferably has an atomic ratio of In equal to or greater than the atomic ratio of M. As the atomic ratio of the metal elements of such a sputtering target, examples of In:M:Zn = 1:1:1, In:M:Zn = 1:1:1.2, In:M:Zn = 2:1:3, In:M :Zn = 3:1:2, In:M:Zn = 4:2:3, In:M:Zn = 4:2:4.1, In:M:Zn = 5:1:6, In:M:Zn = 5:1:7, In:M:Zn = 5:1: 8, In:M:Zn = 6:1:6, In:M:Zn = 5:2:5, etc. can be mentioned.

[0268] The transistors included in circuit unit 303, circuit units 304a and 304b, and pixel unit 302 may have the same structure or different structures. The structures of the multiple transistors included in circuit unit 303, circuit units 304a and 304b may all be the same or there may be two or more types. Similarly, the structures of the multiple transistors included in pixel unit 302 may all be the same or there may be two or more types.

[0269] The end portion of the first electrode 313 is covered by an insulating layer 314. Note that the insulating layer 314 can use organic compounds such as negative photosensitive resin and positive photosensitive resin (acrylic resin), and inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride. The insulating It is preferable that the upper end or the lower end of the layer 314 has a curved surface with a curvature. Thereby the covering property of the film formed on the upper layer of the insulating layer 314 can be made good.

[0270] An EL layer 315 is provided on the first electrode 313, and a second electrode 316 is provided on the EL layer 315. The EL layer 315 includes a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like. The EL layer 315 preferably has an organic compound of an aspect of the present invention shown in Embodiment 1. For example, among the material of the hole injection layer, the material of the hole transport layer, and the host material of the light-emitting layer, it is preferable to have the organic compound as at least one of them.

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

[0272] An epoxy resin or glass frit can be used for the sealing material 305. Note that it is preferable to use a material that hardly permeates moisture and oxygen for the sealing material 305. When glass frit is used as the sealing material, the first substrate 301 and the second substrate 306 are preferably glass substrates from the viewpoint of adhesiveness.

[0273] Examples of transistors that can be used in the light-emitting device are shown in FIGS. 5(C) and 5(D).

[0274] The transistor 320 shown in FIG. 5(C) includes a conductive layer 321 that functions as a gate, an insulating layer 328 that functions as a gate insulating layer, a semiconductor layer 327 having a channel formation region 327i and a pair of low-resistance regions 327n, a conductive layer 322a connected to one of the pair of low-resistance regions 327n, a conductive layer 322b connected to the other of the pair of low-resistance regions 327n, an insulating layer 325 that functions as a gate insulating layer, a conductive layer 323 that functions as a gate, and an insulating layer 324 that covers the conductive layer 323. The insulating layer 328 is located between the conductive layer 321 and the channel formation region 327i. The insulating layer 325 is located between the conductive layer 323 and the channel formation region 327i. The transistor 320 is preferably covered by an insulating layer 326. The insulating layer 326 may be included in the components of the transistor 320. The conductive layers 322a and 322b are connected to the low-resistance regions 327n through openings provided in the insulating layer 324, respectively. One of the conductive layers 322a and 322b functions as a source, and the other functions as a drain. The insulating layer 325 is provided so as to overlap at least the channel formation region 327i of the semiconductor layer 327. The insulating layer 325 may cover the upper surfaces and side surfaces of the pair of low-resistance regions 327n. The transistor 330 shown in FIG. 5(D) includes a conductive layer 331 that functions as a gate, an insulating layer 338 that functions as a gate insulating layer, conductive layers 332a and 332b that function as a source and a drain, a semiconductor layer 337, an insulating layer 335 that functions as a gate insulating layer, and a conductive layer 333 that functions as a gate. The insulating layer 338 is located between the conductive layer 331 and the semiconductor layer 337. The insulating layer 335 is located between the conductive layer 333 and the semiconductor layer 337. The transistor 330 is preferably covered by an insulating layer 336. The insulating layer 336 may be included in the components of the transistor 330. The conductive layers 332a and 332b are connected to the semiconductor layer 337 through openings provided in the insulating layer 334, respectively. One of the conductive layers 332a and 332b functions as a source, and the other functions as a drain. The insulating layer 335 is provided so as to overlap at least the channel formation region of the semiconductor layer 337. The insulating layer 335 may cover the upper surfaces and side surfaces of the semiconductor layer 337. The semiconductor layer 337 has a channel formation region and a pair of low-resistance regions. The pair of low-resistance regions are formed by implanting impurities into the semiconductor layer 337 at a higher concentration than the channel formation region. The semiconductor layer 337 has a channel formation region and a pair of low-resistance regions. The pair of low-resistance regions are formed by implanting impurities into the semiconductor layer 337 at a higher concentration than the channel formation region.

[0275] The conductive layers 322a and 322b are connected to the low-resistance regions 327n through openings provided in the insulating layer 324, respectively. One of the conductive layers 322a and 322b functions as a source, and the other functions as a drain. One of the conductive layers 322a and 322b functions as a source, and the other functions as a drain. The insulating layer 325 is provided so as to overlap at least the channel formation region 327i of the semiconductor layer 327. The insulating layer 325 may cover the upper surfaces and side surfaces of the pair of low-resistance regions 327n.

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

[0277] The transistor 330 shown in FIG. 5(D) includes a conductive layer 331 that functions as a gate, an insulating layer 338 that functions as a gate insulating layer, conductive layers 332a and 332b that function as a source and a drain, a semiconductor layer 337, an insulating layer 335 that functions as a gate insulating layer, and a conductive layer 333 that functions as a gate. The insulating layer 338 is located between the conductive layer 331 and the semiconductor layer 337. The insulating layer 335 is located between the conductive layer 333 and the semiconductor layer 337. The transistor 330 is preferably covered by an insulating layer 336. The insulating layer 336 may be included in the components of the transistor 330. The conductive layers 332a and 332b are connected to the semiconductor layer 337 through openings provided in the insulating layer 334, respectively. One of the conductive layers 332a and 332b functions as a source, and the other functions as a drain. The insulating layer 335 is provided so as to overlap at least the channel formation region of the semiconductor layer 337. The insulating layer 335 may cover the upper surfaces and side surfaces of the semiconductor layer 337. It is located between the layer 337. The insulating layer 335 is located between the conductive layer 333 and the semiconductor layer 337. The transistor 330 is preferably covered by the insulating layer 334. The insulating layer 334 may be included in the components of the transistor 330.

[0278] For the transistor 320 and the transistor 330, a configuration is applied in which a semiconductor layer in which a channel is formed is sandwiched by two gates. The two gates may be connected and the transistor may be driven by supplying the same signal to them. Alternatively, a potential for controlling the threshold voltage may be applied to one of the two gates, and a potential for driving may be applied to the other, thereby controlling the threshold voltage of the transistor.

[0279] It is preferable to use a material in which impurities such as water and hydrogen hardly diffuse in at least one of the insulating layers covering the transistor. Thereby, the insulating layer can function as a barrier layer. By adopting such a configuration, the diffusion of impurities from the outside into the transistor can be effectively suppressed, and the reliability of the light-emitting device can be improved.

[0280] As the insulating layers 325, 326, 328, 334, 335, and 338, it is preferable to use inorganic insulating films respectively. As the inorganic insulating film, for example, a silicon nitride film, a silicon oxynitride film, a silicon oxide film, a silicon nitride oxide film, an aluminum oxide film, an aluminum nitride film, etc. can be used. Further, a hafnium oxide film, a yttrium oxide film, a zirconium oxide film, a gallium oxide film, a tantalum oxide film, a magnesium oxide film, a lanthanum oxide film, a cerium oxide film, a neodymium oxide film, etc. can be used. This is also acceptable. Further, two or more of the above-described insulating films may be laminated and used.

[0281] Note that examples of materials that can be used for the various conductive layers constituting the light-emitting device include aluminum , titanium, chromium, nickel, copper, yttrium, zirconium, molybdenum, silver, tantalum , or tungsten and other metals, or alloys containing these as the main component. In addition, films containing these materials can be used as a single layer or in a laminated structure. For example, a single-layer structure of an aluminum film containing silicon, a two-layer structure in which an aluminum film is laminated on a titanium film , a two-layer structure in which an aluminum film is laminated on a tungsten film, a two-layer structure in which a copper film is laminated on a copper-magnesium-aluminum alloy film , a two-layer structure in which a copper film is laminated on a titanium film, a two-layer structure in which a copper film is laminated on a tungsten film , a three-layer structure in which a titanium film or a titanium nitride film and an aluminum film or a copper film are laminated thereon, and then a titanium film or a titanium nitride film is formed thereon , a three-layer structure in which a molybdenum film or a molybdenum nitride film and an aluminum film or a copper film are laminated thereon, and then a molybdenum film or a molybdenum nitride film is formed thereon There are various structures such as the above. Note that oxides such as indium oxide, tin oxide, or zinc oxide may be used. In addition, using copper containing manganese is preferable because it enhances the controllability of the shape by etching.

[0282]

[0283] This embodiment can be appropriately combined with other embodiments.

[0284] (Embodiment 4) In this embodiment, an electronic device according to one aspect of the present invention will be described with reference to the drawings.

[0284] Examples of electronic devices include television sets, monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (also referred to as mobile telephone devices), portable game machines, portable information terminals, audio playback devices, pachinko machines, large game machines, biometric authentication devices, and inspection devices.

[0285] Since the electronic device according to one aspect of the present invention has the light-emitting device according to one aspect of the present invention on the display unit, it has high luminous efficiency and high reliability.

[0286] On the display unit of the electronic device of the present embodiment, for example, videos having a resolution of full high vision, 4K2K, 8K4K, 16K8K, or higher can be displayed. Also, as the screen size of the display unit, it can be 20 inches or more in diagonal, 30 inches or more in diagonal, 50 inches or more in diagonal, 60 inches or more in diagonal, or 70 inches or more in diagonal.

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

[0288] Also, the electronic device according to one aspect of the present invention may have a secondary battery, and it is preferable that non-contact power transmission is used to charge the secondary battery.

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

[0290] An electronic device according to an aspect of the present invention may have an antenna. By receiving a signal with the antenna, it is possible to display video, information, etc. on the display unit. Further, when the electronic device has an antenna and a secondary battery, the antenna may be used for non-contact power transmission.

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

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

[0293] FIG. 6(A) shows an example of a television device. In the television device 7100, a display unit 7000 is incorporated in a housing 710 1. Here, a configuration in which the housing 710 1 is supported by a stand 7103 is shown.

[0294] The light-emitting device according to an aspect of the present invention can be applied to the display unit 7000.

[0295] The operation of the television device 7100 shown in FIG. 6(A) can be performed by operation switches provided in the housing 7101 or by a separate remote control operation unit 7111. Alternatively, the display unit 7000 ​It may be provided with a touch sensor and may be operated by touching the display unit 7000 with a finger or the like. The remote control operation unit 7111 may have a display unit that displays information output from the remote control operation unit 7111. The operation keys or touch panel provided in the remote control operation unit 7111 can be used to operate the channel and volume, and can also be used to operate the video displayed on the display unit 7000.

[0296] Note that the television device 7100 is configured to include a receiver and a modem, etc. The receiver can receive general television broadcasts. Also, by connecting to a wired or wireless communication network via the modem, it is possible to perform one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.

[0297] FIG. 6(B) shows an example of a notebook personal computer. The notebook personal computer 7200 has a housing 7211, a keyboard 7212, a pointing device 7213, an external connection port 7214, etc. The display unit 7000 is incorporated in the housing 7211.

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

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

[0300] The digital signage 7300 shown in FIG. 6(C) has a housing 7301, a display unit 7000, and a speaker 7303, etc. Further, it has an LED lamp, operation keys (power switch, or It can have an operation switch, connection terminals, various sensors, a microphone, etc. 。

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

[0302] In FIGS. 6(C) and 6(D), the light-emitting device according to an aspect of the present invention can be applied to the display unit 7000. can do.

[0303] The wider the display unit 7000 is, the more information can be provided at once. Also, the wider the display unit 7000 is, the easier it is to catch people's eyes, and for example, the advertising effect can be enhanced. The wider the display unit 7000 is, the easier it is to catch people's eyes, and for example, the advertising effect can be enhanced. possible.

[0304] By applying a touch panel to the display unit 7000, not only can an image or video be displayed on the display unit 7000, but also the user can operate it intuitively, which is preferable. Also, when used for providing information such as route information or traffic information, the usability can be enhanced by intuitive operation. shown, but also the user can operate it intuitively, which is preferable. Also, when used for providing information such as route information or traffic information, the usability can be enhanced by intuitive operation. or traffic information, the usability can be enhanced by intuitive operation. can enhance usability.

[0305] Also, as shown in FIGS. 6(C) and 6(D), the digital signage 7300 or the digital signage 7400 is preferably capable of wireless communication with an information terminal 7311 such as a smartphone held by the user or an information terminal 7411. For example, the information of the advertisement displayed on the display unit 7000 can be displayed on the screen of the information terminal 7311 or the information terminal 7411. Also, the information terminal 7311 or the information terminal 7411 can be operated. It is preferably possible to cooperate with an information terminal 7311 or an information terminal 7411 by wireless communication. For example, the information of the advertisement displayed on the display unit 7000 can be displayed on the screen of the information terminal 7311 or the information terminal 7411. Also, the information terminal 7311 or the information terminal 7411 can be operated. is preferably capable of wireless communication with an information terminal 7311 such as a smartphone held by the user or an information terminal 7411. For example, the information of the advertisement displayed on the display unit 7000 can be displayed on the screen of the information terminal 7311 or the information terminal 7411. Also, the information terminal 7311 or the information terminal 7411 can be operated. 7000 can be displayed on the screen of the information terminal 7311 or the information terminal 7411. Also, the information terminal 7311 or the information terminal 7411 can be operated. 7000 can be displayed on the screen of the information terminal 7311 or the information terminal 7411. Also, the information terminal 7311 or the information terminal 7411 can be operated. By operating the buttons, the display on the display unit 7000 can be switched.

[0306] In addition, the digital signage 7300 or the digital signage 7400 is provided with an information terminal 7 311 or the screen of the information terminal 7411 is used as a control means (controller) to play games. This allows an unspecified number of users to participate in the game at the same time and enjoy it. It is possible.

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

[0308] The display portion 7001 is manufactured using a light-emitting device according to one embodiment of the present invention. Light-emitting devices that can be bent from 0.01 mm to 150 mm can be applied. The display unit 7001 may be provided with a touch sensor, and the display unit 7001 may be turned on by touching the display unit 7001 with a finger or the like. It is possible to operate a portable information terminal.

[0309] 7(A) to 7(C) show an example of a foldable portable information terminal. In Fig. 7(B), the state is changed from either the unfolded or folded state to the other. In FIG. 7C, the mobile information terminal 7600 is in a folded state. The portable information terminal 7600 is highly portable when folded and is portable when unfolded. The large, seamless display area provides excellent visibility.

[0310] The display unit 7001 is supported by three housings 7601 connected by hinges 7602. The two housings 7601 are bent via the hinge 7602, so that the portable information terminal It can be reversibly deformed from the state in which the end 7600 is unfolded to the folded state.

[0311] Figures 7(D) and 7(E) show an example of a foldable portable information terminal. In Figure 7(D), it shows the state where the display unit 7001 is folded inward, and in Figure 7(E), it shows the portable information terminal 7650 in the state where the display unit 70 01 is folded outward. The portable information terminal 7650 has a display unit 7001 and a non-display unit 7651. When not using the portable information terminal 7650, by folding it so that the display unit 7001 is inside, it is possible to suppress dirt or damage to the display unit 7001.

[0312] Figure 7(F) shows an example of a wristwatch-type portable information terminal. The portable information terminal 7800 has a band 7 801, a display unit 7001, input / output terminals 7802, operation buttons 7803, etc. The band 7801 has the function of a housing. Also, the portable information terminal 7800 can be equipped with a flexible battery 7805. The battery 7805 can be arranged, for example, overlapping the display unit 7001 or the band 7801.

[0313] The band 7801, the display unit 7001, and the battery 7805 have flexibility. Therefore, it is easy to bend the portable information terminal 7800 into a desired shape.

[0314] In addition to time setting, the operation buttons 7803 can perform various functions such as turning on and off the power, turning on and off wireless communication, executing and canceling the silent mode, and executing and canceling the power-saving mode. For example, the functions of the operation buttons 7803 can also be freely set by the operating system embedded in the portable information terminal 7800. stem.

[0315] Also, by touching the icon 7804 displayed on the display unit 7001 with a finger or the like, an applica tion can be launched.

[0316] Also, the mobile information terminal 7800 can execute short-range wireless communication that complies with a communication standard and is capable of. For example, by communicating with a wireless headset, hands-free calls can also be made.

[0317] Also, the mobile information terminal 7800 may have an input / output terminal 7802. When having the input / output terminal 78 02, direct data exchange can be performed with other information terminals via a connector and is possible. Also, charging can be performed via the input / output terminal 7802. Note that the charging operation of the mobile information terminal exemplified in this embodiment may be performed by non-contact power transmission without passing through the input / output terminal.

[0318] FIG. 8(A) shows the appearance of the automobile 9700. FIG. 8(B) shows the driver's seat of the automobile 9700 . The automobile 9700 has a vehicle body 9701, wheels 9702, a front glass 9703, lights 9 704, fog lamps 9705, etc. The light-emitting device according to one aspect of the present invention can be used for the display unit of the automobile 970 0 and the like. For example, the light-emitting device according to one aspect of the present invention can be provided in the display units 9710 to 9715 shown in FIG. 8(B). Alternatively, the light-emitting device according to one aspect of the present invention may be used for the lights 970 4 or the fog lamps 9705.

[0319] The display unit 9710 and the display unit 9711 are display devices provided on the front glass of the automobile and are. The light-emitting device according to one aspect of the present invention is made of a conductive material having translucency for electrodes and wiring By doing so, a so-called see-through state in which the opposite side can be seen through can be achieved. If the display unit 9710 or the display unit 9711 is in a see-through state, it will not obstruct the view during the operation of the automobile 9700. Therefore, the light-emitting device according to one aspect of the present invention can be installed on the windshield of the automobile 9700. When providing a transistor or the like for driving the light-emitting device, an organic transistor using an organic semiconductor material or a transistor using an oxide semiconductor, etc., a light-transmissive transistor may be used. The display unit 9712 is a display device provided in the pillar portion. For example, by projecting the video from the imaging means provided on the vehicle body onto the display unit 9712, the view blocked by the pillar can be compensated. The display unit 9713 is a display device provided in the dashboard portion. For example, by projecting the video from the imaging means provided on the vehicle body onto the display unit 9713, the view blocked by the dashboard can be compensated. That is, by projecting the video from the imaging means provided outside the automobile, the blind spot can be compensated and the safety can be improved.

[0320] Also, by projecting a video that compensates for the invisible part, a safety check can be performed more naturally without a sense of discomfort. The display unit 9713 is a display device provided in the dashboard portion. For example, by projecting the video from the imaging means provided on the vehicle body onto the display unit 9713, the view blocked by the dashboard can be compensated. That is, by projecting the video from the imaging means provided outside the automobile, the blind spot can be compensated and the safety can be improved. Also, by projecting a video that compensates for the invisible part, a safety check can be performed more naturally without a sense of discomfort. For example, by projecting the video from the imaging means provided on the vehicle body onto the display unit 9713, the view blocked by the dashboard can be compensated. That is, by projecting the video from the imaging means provided outside the automobile, the blind spot can be compensated and the safety can be improved. Also, by projecting a video that compensates for the invisible part, a safety check can be performed more naturally without a sense of discomfort. That is, by projecting the video from the imaging means provided outside the automobile, the blind spot can be compensated and the safety can be improved. Also, by projecting a video that compensates for the invisible part, a safety check can be performed more naturally without a sense of discomfort. Also, by projecting a video that compensates for the invisible part, a safety check can be performed more naturally without a sense of discomfort.

[0321] Also, Fig. 8(C) shows the interior of an automobile adopting bench seats for the driver's seat and the passenger seat. The display unit 9721 is a display device provided in the door portion. For example, by projecting the video from the imaging means provided on the vehicle body onto the display unit 9721, the view blocked by the door can be compensated. Also, the display unit 9722 is a display device provided on the steering wheel. For example, by projecting the video from the imaging means provided on the vehicle body onto the display unit 9721, the view blocked by the door can be compensated. The display unit 9723 is a display device provided at the center of the seating surface of the bench seat. Note that the display device can also be installed on the seating surface or the backrest portion, etc., and the display device can be used as a seat heater using the heat generated by the display device as a heat source.

[0322] The display unit 9714, the display unit 9715, or the display unit 9722 can display navigation information, speedometer, tachometer, travel distance, fuel gauge, gear state, air conditioning settings, etc., and can provide various information in this way. Also, the display items and layout displayed on the display unit can be appropriately changed according to the user's preference. Note that the above information can also be displayed on the display units 9710 to 9713, the display unit 9721, and the display unit 9723. In addition, the display units 9710 to 9715 and the display units 9721 to 9723 can also be used as lighting devices. Also, the display units 9710 to 9715 and the display units 9721 to 9723 can also be used as heating devices.

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

[0324] FIG. 9(A) is a biometric authentication device for finger veins, and includes a housing 911, a light source 912, a detection stage 913, etc. By placing a finger on the detection stage 913, the shape of the vein can be imaged. A light source 912 that emits near-infrared light is installed above the detection stage 913. ​​​​​​​​​is provided, and an imaging device 914 is installed at the bottom. The detection stage 913 is made of a material that transmits near-infrared light and is irradiated by the light source 912. The near-infrared light that passes through the finger can be imaged by the imaging device 91 4. An optical system may be provided between the detection stage 913 and the imaging device 914. The configuration of the above equipment can also be used for a biometric authentication device targeting the veins on the palm.

[0325] The light-emitting device according to one aspect of the present invention can be used as the light source 912. The light-emitting device according to one aspect of the present invention can be installed in a curved shape and can irradiate an object with light uniformly. In particular, it is preferably a light-emitting device that emits near-infrared light having the strongest peak intensity at a wavelength of 700 nm or more and 1200 nm or less. By receiving the light that has passed through a finger or palm and imaging it, the position of the vein can be detected. This action can be used for biometric authentication. Also, by combining with the global shutter method, high-precision sensing is possible even if the subject moves.

[0326] Also, the light source 912 can have a plurality of light-emitting parts, such as the light-emitting parts 915, 916, and 917 shown in FIG. 9(B). Each of the light-emitting parts 915, 916, and 917 may have a different emission wavelength. Also, they can be irradiated at different timings. Therefore, by changing the wavelength and angle of the irradiated light, different images can be continuously imaged, so that a plurality of images can be used for authentication to achieve high security.

[0327] FIG. 9(C) shows a biometric authentication device targeting the veins on the palm, including a housing 921 and operation buttons ​​​​​​​​​​​​It includes a detection unit 923, a light source 924 that emits near-infrared light, etc. By holding a hand over the detection unit 923, the shape of the veins on the palm can be recognized. Also, a password or the like can be input using an operation button. A light source 924 is arranged around the detection unit 923 to irradiate an object (hand). Then, the reflected light from the object is incident on the detection unit 923. The light-emitting device according to one aspect of the present invention can be used as the light source 924. An imaging device 925 is arranged directly below the detection unit 923, and an image of the object (an overall image of the hand) can be captured. Note that an optical system may be provided between the detection unit 923 and the imaging device 925. The configuration of the above device can also be used for a biometric authentication device targeting finger veins. By holding a hand over the detection unit 923, the shape of the veins on the palm can be recognized. Also, a password or the like can be input using an operation button. A light source 924 is arranged around the detection unit 923 to irradiate an object (hand). Then, the reflected light from the object is incident on the detection unit 923. The light-emitting device according to one aspect of the present invention can be used as the light source 924. An imaging device 925 is arranged directly below the detection unit 923, and an image of the object (an overall image of the hand) can be captured. Note that an optical system may be provided between the detection unit 923 and the imaging device 925. The configuration of the above device can also be used for a biometric authentication device targeting finger veins. An imaging device 925 is arranged directly below the detection unit 923, and an image of the object (an overall image of the hand) can be captured. Note that an optical system may be provided between the detection unit 923 and the imaging device 925. The configuration of the above device can also be used for a biometric authentication device targeting finger veins. The configuration of the above device can also be used for a biometric authentication device targeting finger veins.

[0328] FIG. 9(D) is a non-destructive inspection device, which includes a housing 931, an operation panel 932, a transport mechanism 933, a monitor 934, a detection unit 935, a light source 938 that emits near-infrared light, etc. The light-emitting device according to one aspect of the present invention can be used as the light source 938. The member to be inspected 936 is transported directly below the detection unit 935 by the transport mechanism 933. The member to be inspected 936 is irradiated with near-infrared light from the light source 938, and the transmitted light is imaged by an imaging device 937 provided in the detection unit 935. The captured image is displayed on the monitor 934. Then, it is transported to the exit of the housing 931, and defective products are sorted and collected. By imaging using near-infrared light, defective elements such as defects and foreign objects inside the member to be inspected can be detected non-destructively and at high speed. The member to be inspected 936 is irradiated with near-infrared light from the light source 938, and the transmitted light is imaged by an imaging device 937 provided in the detection unit 935. The captured image is displayed on the monitor 934. Then, it is transported to the exit of the housing 931, and defective products are sorted and collected. By imaging using near-infrared light, defective elements such as defects and foreign objects inside the member to be inspected can be detected non-destructively and at high speed. The captured image is displayed on the monitor 934. Then, it is transported to the exit of the housing 931, and defective products are sorted and collected. By imaging using near-infrared light, defective elements such as defects and foreign objects inside the member to be inspected can be detected non-destructively and at high speed. By imaging using near-infrared light, defective elements such as defects and foreign objects inside the member to be inspected can be detected non-destructively and at high speed.

[0329] FIG. 9(E) is a mobile phone, which includes a housing 981, a display unit 982, operation buttons 983, an external connection port 984, a speaker 985, a microphone 986, a first camera 987, a second camera 9 88, etc. It has 88 etc. The mobile phone is provided with a touch sensor on the display unit 982. The housing 981 and the display unit 982 are flexible. Any operation such as making a call or inputting characters can be performed by touching the display unit 982 with a finger or a stylus. The first camera 987 can acquire a visible light image, and the second camera 988 can acquire an infrared light image (near-infrared light image). The mobile phone or the display unit 9 82 shown in Fig. 9(E) may have a light-emitting device according to an aspect of the present invention.

[0330] This embodiment can be appropriately combined with other embodiments.

Example

[0331] (Synthesis Example 1) In this example, a method for synthesizing an organic compound according to an aspect of the present invention will be described. In this example , the synthesis method of N-[4''-(9H-carbazol-9 -yl)-1,1':4',1''-terphenyl-4-yl]-N-(1,1'-bip henyl-2-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: oYG TBiF(2)) represented by the structural formula (100) of Embodiment 1 will be described.

[0332]

Chemical formula

[0333] First, 1.3 g (3.7 mmol) of N-[1,1'-biphenyl]-2-yl-9,9 -dimethyl-9H-fluorene-2-amine and 1.6 g (3.7 mmol) of 9-(4 ''-chloro[1,1':4',1''-terphenyl]-4-yl)-9H-carbazo -ol and 26 mg (74 μmol) of di-tert-butyl(1-methyl-2,2-dif enylcyclopropyl)phosphine (registered trademark: cBRIDP) were placed in a 20 0 mL three-necked flask equipped with a reflux tube, and the system was purged with nitrogen. 0.71 g (7.4 mmol) of sodium tert-butoxide and 30 mL of xylene were added to the system, and degassing under reduced pressure and nitrogen replacement were carried out three times each. 21 mg (37 μmol) of bis(dibenzylideneacetone )palladium(0) was added to the system, and the mixture was stirred at 150 °C for 10 hours. After stirring, insoluble materials were removed from the mixture by suction filtration. Water was added to the obtained filtrate, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water and then with saturated brine. The organic layer was dried over magnesium sulfate . The obtained mixture was filtered naturally to remove magnesium sulfate. The obtained filtrate was concentrated to obtain 2.6 g of a yellow viscous solid. The obtained solid was purified by silica gel chromatography (the developing solvent was toluene:hexane = 1:2), and the obtained pale yellow solid was recrystallized from toluene to obtain 0.83 g of a pale yellow solid with a yield of 30%. The obtained 0.83 g of solid was purified by sublimation using the train sublimation method. The sublimation purification was carried out by heating the solid at 320 °C for 16 hours while flowing argon at 15 mL / min under a pressure of 3.8 Pa. After sublimation purification, 0.55 g of the target pale yellow solid was obtained with a recovery rate of 66%. In the sublimation purification, the material sublimated due to heating at 320 °C, and the recovery rate was as high as 66%.

[0334] From this, it was confirmed that the organic compound of one aspect of the present invention has good sublimability and no problem in the vapor deposition process . The synthetic scheme is shown in (A-1). After sublimation purification, 0.55 g of the target pale yellow solid was obtained with a recovery rate of 66%. In the sublimation purification, the material sublimated due to heating at 320 °C, and the recovery rate was as high as 66%. From this, it was confirmed that the organic compound of one aspect of the present invention has good sublimability and no problem in the vapor deposition process . The synthetic scheme is shown in (A-1).

[0335]

Chemical formula

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

[0337] 1 H NMR (dichloromethane-d2, 300 MHz): δ = 8.17 (d, J = 7. 8 Hz, 2H), 7.91 (d, J = 8.7 Hz, 2H), 7.78 (d, J = 8.7 H z, 2H), 7.71 (d, J = 8.7 Hz, 2H), 7.67 (d, J = 8.7 Hz, 2H), 7.57 (d, J = 7.2 Hz, 1H), 7.52 - 7.19 (m, 18H), 7.14 - 7.06 (m, 5H), 6.92 (d, J = 1.8 Hz, 1H), 6.79 ( dd, J1 = 6.0 Hz, J2 = 2.1 Hz, 1H), 1.30 (s, 6H).

[0338] Next, the ultraviolet-visible absorption spectra (hereinafter simply referred to as "absorption spectra") and emission spectra of the toluene solution and solid thin film of oYGTBiF(2) were measured. The solid thin film was fabricated on a quartz substrate by vacuum evaporation.

[0339] An ultraviolet-visible spectrophotometer (solution: V-550 manufactured by JASCO Corporation, thin film: U-4100 manufactured by Hitachi High-Technologies Corporation) was used for the measurement of the absorption spectrum. The absorption spectrum of oYGTBiF(2) in the toluene solution was calculated by subtracting the absorption spectrum obtained by measuring toluene in a quartz cell from the absorption spectrum obtained by measuring the toluene solution of oYGTBiF(2) in a quartz cell. The absorption spectrum of the thin film was measured including the substrate. ​ Absorbance determined from the transmittance and reflectance (-log 10 calculated from [%T / (100-%R)]. Here, %T represents the transmittance and %R represents the reflectance. Also, a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics K.K.) was used for the measurement of the emission spectrum. For both the absorption spectrum and the emission spectrum, the measurement was performed at room temperature. The measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution are shown in Fig. 10(A). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity.

[0340] From Fig. 10(A), in the toluene solution of oYGTBiF(2), an absorption peak was observed around 366 nm, and an emission peak was observed around 421 nm (excitation wavelength: 366 nm). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity.

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

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

[0343] From Fig. 10(B), in the solid thin film of oYGTBiF(2), absorption peaks were observed around 294 nm, around 350 nm, and around 367 nm, and an emission peak was observed around 440 nm (excitation wavelength: 365 nm). From Fig. 10(B), in the solid thin film of oYGTBiF(2), absorption peaks were observed around 294 nm, around 350 nm, and around 367 nm, and an emission peak was observed around 440 nm (excitation wavelength: 365 nm). From Fig. 10(B), in the solid thin film of oYGTBiF(2), absorption peaks were observed around 294 nm, around 350 nm, and around 367 nm, and an emission peak was observed around 440 nm (excitation wavelength: 365 nm).

[0344] The organic compound, oYGTBiF(2), of one embodiment of the present invention was found to be a host material suitable for a fluorescent material that emits light with blue and longer wavelength energy, and a phosphorescent material that emits light with green and longer wavelength energy. oYGTBiF(2) can be used as a host material used together with a luminescent substance (such as a fluorescent material, a delayed fluorescence material, or a phosphorescent material) in the visible region or the near-infrared region, or as a luminescent substance. The organic compound, oYGTBiF(2), of one embodiment of the present invention was found to be a host material suitable for a fluorescent material that emits light with blue and longer wavelength energy, and a phosphorescent material that emits light with green and longer wavelength energy. oYGTBiF(2) can be used as a host material used together with a luminescent substance (such as a fluorescent material, a delayed fluorescence material, or a phosphorescent material) in the visible region or the near-infrared region, or as a luminescent substance. The organic compound, oYGTBiF(2), of one embodiment of the present invention was found to be a host material suitable for a fluorescent material that emits light with blue and longer wavelength energy, and a phosphorescent material that emits light with green and longer wavelength energy. oYGTBiF(2) can be used as a host material used together with a luminescent substance (such as a fluorescent material, a delayed fluorescence material, or a phosphorescent material) in the visible region or the near-infrared region, or as a luminescent substance. The organic compound, oYGTBiF(2), of one embodiment of the present invention was found to be a host material suitable for a fluorescent material that emits light with blue and longer wavelength energy, and a phosphorescent material that emits light with green and longer wavelength energy. oYGTBiF(2) can be used as a host material used together with a luminescent substance (such as a fluorescent material, a delayed fluorescence material, or a phosphorescent material) in the visible region or the near-infrared region, or as a luminescent substance. The organic compound, oYGTBiF(2), of one embodiment of the present invention was found to be a host material suitable for a fluorescent material that emits light with blue and longer wavelength energy, and a phosphorescent material that emits light with green and longer wavelength energy. oYGTBiF(2) can be used as a host material used together with a luminescent substance (such as a fluorescent material, a delayed fluorescence material, or a phosphorescent material) in the visible region or the near-infrared region, or as a luminescent substance.

[0345] Next, the HOMO and LUMO levels of oYGTBiF(2) were measured by cyclic voltammetry. The calculation method is shown below.

[0346] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Co., Ltd., 99.8%, Catalog No. 227 05-6) was used as the supporting electrolyte, tetra-n-butylammonium perchlorate (nB u4NClO4) (Tokyo Chemical Industry Co., Ltd., catalog number: T0836) was added at 100 mmol / The measurement target was then dissolved in water to a concentration of 2 mmol / L. The mixture was then dissolved and prepared.

[0347] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.). The auxiliary electrode was a platinum electrode (manufactured by BAS Co., Ltd., a Pt counter electrode for VC-3 ( 5cm)) as the reference electrode, and Ag / Ag + Electrode (B.A.S. Co., Ltd., RE7 The measurements were performed at room temperature (20°C to 25°C). went.

[0348] In addition, the scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation rate relative to the reference electrode was The potential Ea [V] and the reduction potential Ec [V] were measured. Ea is the midpoint potential of the oxidation-reduction wave. , Ec is the midpoint potential of the reduction-oxidation wave. Here, the vacuum level of the reference electrode used in this example Since the potential energy for is known to be -4.94 eV, , HOMO level [eV]=-4.94 - Ea, LUMO level [eV]=-4.94 - Ec From this equation, the HOMO level and the LUMO level can be obtained respectively.

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

[0350] As a result, in the measurement of the oxidation potential Ea [V] of oYGTBiF(2), the HOMO level was found to be -5.42 eV. On the other hand, in the measurement of the reduction potential Ec [V], the LU MO level was -2.31 eV, indicating that it has high electron blocking properties. Also, in the repeated measurement of the oxidation-reduction wave, when comparing the waveforms after the first cycle and the 100th cycle, it was found that in the Ea measurement, 88% of the peak intensity was maintained, and in the Ec measurement, 99% of the peak intensity was maintained. Therefore, it was confirmed that oYGTBiF(2) has very good resistance to oxidation and reduction.

[0351] Also, the differential scanning calorimetry (DSC measurement) of oYGTBiF(2) was measured using Pyris1DSC manufactured by PerkinElmer. The differential scanning calorimetry measurement was carried out by heating from -10°C to 320°C at a heating rate of 40°C / min, holding at the same temperature for 1 minute, and then cooling to -10°C at a cooling rate of 1 00°C / min twice continuously. From the DSC measurement results of the second cycle, it was revealed that the glass transition point of oYGTBiF(2) is 137°C, indicating that it is a substance with very high heat resistance.

[0352] Also, the thermogravimetric measurement-differential thermal analysis (Thermogravimet​​ Thermogravimetric-differential thermal analysis was performed. The measurement was carried out using a high-vacuum differential thermogravimetric balance (manufactured by Bruker AXS K.K., TG-DTA2 410SA). The measurement was performed at atmospheric pressure with a heating rate of 10 °C / min under a nitrogen gas flow (flow rate: 200 mL / min). In the thermogravimetric-differential thermal analysis, the temperature at which the weight obtained from the thermogravimetric measurement became -5% of that at the start of the measurement (decomposition temperature) was found to be 484 °C, indicating that it is a substance with high heat resistance.

[0353] From the above results, the organic compound of one aspect of the present invention has both high heat resistance and high sublimability, and can provide an organic optoelectronic device (light-emitting device and light-receiving device) with high heat resistance. Also, it was confirmed that the productivity of device fabrication can be increased.

Examples

[0354] In this example, a light-emitting device of one aspect of the present invention was fabricated, and the evaluation results will be described. .

[0355] In this example, as the light-emitting device, Device 1 using oYGTBiF(2) (structural formula (100)) described in Example 1, Comparative Device 2 for comparison, Comparative Device 3, and Comparative Device 4 were fabricated, and the evaluation results will be described.

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

[0357]

Table 1

[0358]

Chem.

[0359] ≪Fabrication of Light-Emitting Device≫ The light-emitting device shown in this example has a structure in which a first electrode 801 is formed on a substrate 800 as shown in Fig. 11, and a hole injection layer 811, a hole transport layer 8 12, a light-emitting layer 813, an electron transport layer 814, and an electron injection layer 815 are sequentially stacked as an EL layer 802 on the first electrode 801, and a second electrode 803 is stacked on the electron injection layer 815. First, a first electrode 801 was formed on the substrate 800. The electrode area was 4 mm (2 mm × 2

[0360] mm). A glass substrate was used for the substrate 800. The first electrode 801 was formed by sputtering indium tin oxide (ITSO) containing silicon oxide to a film thickness of 70 nm. 2 (2 mm × 2 mm). In this example, the first electrode 801 functions as an anode. Here, as a pretreatment, the surface of the substrate was washed with water, baked at 200 °C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. Then, the substrate was introduced into a vacuum evaporation apparatus whose internal pressure was reduced to about 10 Pa, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum evaporation apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0361] Next, a hole injection layer 811 was formed on the first electrode 801. After reducing the pressure in the vacuum evaporation apparatus to 10 Pa, material X and ALD-MP001Q (Analytical Works Co., Ltd., material serial number: 1S20180314) were used, with material X:ALD-MP001 -4 Pa, and then the substrate was introduced into a vacuum evaporation apparatus whose internal pressure was reduced to about 10 Pa, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum evaporation apparatus, and then the substrate was allowed to cool for about 30 minutes. Here, as a pretreatment, the surface of the substrate was washed with water, baked at 200 °C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. Then, the substrate was introduced into a vacuum evaporation apparatus whose internal pressure was reduced to about 10

[0362] Next, a hole injection layer 811 was formed on the first electrode 801. The hole injection layer 811 was formed by vacuum evaporation after reducing the pressure in the vacuum evaporation apparatus to 10 Pa, and then the substrate was introduced into a vacuum evaporation apparatus whose internal pressure was reduced to about 10 -4 Pa, and then material X and ALD-MP001Q (Analytical Works Co., Ltd., material serial number: 1S20180314) were used, with material X:ALD-MP001 Company, material serial number: 1S20180314), and, with material X:ALD-MP001 It was formed by co-evaporation with Q = 1:0.1 (weight ratio) so that the film thickness became 10 nm. Note that , ALD-MP001Q is an acceptor material.

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

[0364] As material X in the hole injection layer 811 and the hole transport layer 812, in device 1, N- 4’’-(9H-carbazol-9-yl)-1,1’:4’,1’’-terphenyl- 4-yl]-N-(1,1’-biphenyl-2-yl)-9,9-dimethyl-9H-flu orene-2-amine (abbreviation: oYGTBiF(2)) was used. In comparative device 2, N- [4’-(9H-carbazol-9-yl)-1,1’-biphenyl-4-yl]-N- (1,1’-biphenyl-2-yl)-9,9’-dimethyl-9H-fluorene-2-a mine (abbreviation: oYGBBiF) was used. In comparative device 3, 2,4’-diphenyl-4 ’’-[4’-(9H-carbazol-9-yl)-1,1’-biphenyl-4-yl] triphenylamine (abbreviation: oYGTBi1BP) was used. In comparative device 4, N- 4’’-(9H-carbazol-9-yl)-1,1’:4’,1’’-terphenyl- 4-yl]-N-(1,1’-biphenyl-4-yl)-9,9-dimethyl-9H-flu orene-2-amine (abbreviation: YGTBiF(2)) was used.

[0365] Next, a light-emitting layer 813 was formed on the hole transport layer 812. As the host material, 7-[4-( 10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) was used, and as the guest material (fluorescent material), 3,10-bis N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho [2,3-b;6,7-b’]bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV) -02) was used, and co-evaporation was performed such that the weight ratio was cgDBCzPA:3,10PCA2Nbf(IV)-02= 1:0.015. The film thickness was set to 25 nm.

[0366] Next, an electron transport layer 814 was formed on the light-emitting layer 813. The electron transport layer 814 was deposited such that the film thickness of cgDBC zPA was 15 nm, and 2,9-bis(naphthalen-2-yl)- 4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) was deposited such that the film thickness was 10 nm to form it.

[0367] Next, an electron injection layer 815 was formed on the electron transport layer 814. The electron injection layer 815 was formed by depositing lithium fluoride (LiF) such that the film thickness was 1 nm.

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

[0369] Through the above steps, a light-emitting device was formed on the substrate 800 with an EL layer 802 sandwiched between a pair of electrodes. Note that the hole injection layer 811, hole transport layer 812, and light-emitting layer described in the above steps ​ 813, the electron transport layer 814, and the electron injection layer 815 are functional layers that constitute the EL layer in the light-emitting device of one aspect of the present invention. Also, in the vapor deposition process in the manufacturing method described above, a vapor deposition method using a resistance heating method was used for all.

[0370] Further, the light-emitting device manufactured as described above is sealed with another substrate (not shown). When sealing with another substrate (not shown), in a glove box under a nitrogen atmosphere, another substrate (not shown) coated with an adhesive that cures by ultraviolet light is fixed on the substrate 800, and the substrates are adhered to each other so that the adhesive adheres to the periphery of the light-emitting device formed on the substrate 800. At the time of sealing, ultraviolet light of 365 nm was irradiated at 6 J / cm to cure the adhesive, and the adhesive was stabilized by heat treatment at 80°C for 1 hour. 2

[0371] ≪Operating Characteristics of Light-Emitting Device≫ The operating characteristics of the light-emitting device manufactured in this example were measured. The measurement was performed at room temperature.

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

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

[0374]

Table 2

[0375] As shown in FIGS. 12 to 15 and Table 2, the device 1, the comparative device 2, and the comparative device 4 were found to have high luminous efficiency. Also, the device 1 was found to have higher luminous efficiency than the comparative device 3.

[0376] Also, the emission spectrum when a current was passed through the light-emitting device at a current density of 12.5 mA / cm 2 is shown in FIG. 16. As shown in FIG. 16, the device 1 has a maximum peak at around 459 nm due to the emission of 3, 10PCA2Nbf(IV)-02 contained in the light-emitting layer 813, and shows an emission spectrum. Similarly, the comparative device 2 has a maximum peak at around 458 nm, the comparative device 3 has a maximum peak at around 457 nm, and the comparative device 4 has a maximum peak at around 459 nm, and each shows an emission spectrum. Next, a reliability test was conducted on the light-emitting device. The results of the reliability test are shown in FIG. 17. In FIG.

[0377] 17(A), the vertical axis represents the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis represents the driving time (h). In FIG. 17(B), the vertical axis represents the voltage change (ΔV) from the initial voltage (when the driving time is 0 h), and the horizontal axis represents the driving time (h). Note that the reliability test was performed by setting the current density to 50 mA / cm and driving the light-emitting device.

[0378] 2 When comparing the luminance after 330 hours, the device 1 maintained 85% of the initial luminance, the comparative device 2 maintained 80% of the initial luminance, the comparative device 3 maintained 87% of the initial luminance, and the comparative device 4 maintained 82% of the initial luminance.

[0379] From this, the device 1 has the same luminous efficiency as the comparative devices 2 and 4 ​​and was found to have higher reliability. Also, Device 1 was found to have higher luminous efficiency than Comparative Device 3 and equivalent reliability. and was found to have higher luminous efficiency and equivalent reliability.

[0380] oYGTBiF(2) used in Device 1 is a tertiary amine, and a biphenyl skeleton ortho-position, a fluorene skeleton, and a terphenylene skeleton are bonded to the nitrogen of the amine. and a carbazole skeleton is bonded to the phenylene group farthest from the nitrogen of the amine in the terphenylene skeleton. That is, the nitrogen of the amine and the nitrogen of the carbazole are bonded via the terphenylene skeleton. On the other hand, oYGBBiF used in Comparative Device 2 is different from oYGTBiF(2) used in Device 1 in that the nitrogen of the carbazole and the nitrogen of the amine are bonded via a biphenylene skeleton instead of a terphenylene skeleton. Further, oYGTBi1BP used in Comparative Device 3 is different from oYGTBiF(2) in that a para-position of a biphenyl skeleton, instead of a fluorene skeleton, is bonded to the nitrogen of the amine. YGTBiF(2) used in Comparative Device 4 is different from oYGTBiF(2) in that a para-position of a biphenyl skeleton, instead of an ortho-biphenyl skeleton, is bonded to the nitrogen of the amine. From the above, it can be said that by using an organic compound which is a tertiary amine and to the nitrogen of which a biphenyl skeleton ortho-position, a fluorene skeleton, and a terphenylene skeleton are bonded and a carbazole skeleton is bonded to the phenylene group farthest from the nitrogen of the amine in the terphenylene skeleton, both the luminous efficiency and the reliability of the light-emitting device can be enhanced.

Example

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

[0382] In this example, the light-emitting device is oYGTBiF(2) (structural formula: We fabricated and evaluated Device 5 and Device 6 using the (100) structure. do.

[0383] The specific configurations of the two light-emitting devices used in this example are shown in Table 3. The structure of device 5 is similar to that of device 1 (FIG. 11) except that the light-emitting material of light-emitting layer 813 is changed. The structure of device 6 is similar to that of device 5, except that the thickness of hole transport layer 812 is increased. Therefore, the fabrication method of Device 5 and Device 6 was the same as that of Device 1. For the part, see Example 2. The chemical formulas of the materials used in this example are shown below. vinegar.

[0384] [Table 3]

[0385] [ka]

[0386] As shown in Table 3, in the light-emitting device of this example, the light-emitting layer 813 contains, as a host material, Using cgDBCzPA, N,N'-(pyrene-1,6-diyl)bis(phenylene) was used as the luminescent material. [(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] The antibody used was 1,6BnfAPrn-03.

[0387] As shown in Table 3, the devices 5 and 6 were different in the number of oY films used in the hole transport layer 812. The film thicknesses of GTBiF(2) are different from each other.

[0388] ≪Operating characteristics of the light-emitting device≫ The operating characteristics of the light-emitting device fabricated in this example were measured. The measurement was performed at room temperature. done.

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

[0390] Table 4 shows the main initial characteristic values of the light-emitting device near 1000 cd / m². 2 near 1000 cd / m².

[0391]

Table 4

[0392] As shown in Figs. 18 to 21 and Table 4, it was found that Devices 5 and 6 have high luminous efficiency. Also, although the film thickness of the hole transport layer 812 of Device 6 was increased by 100 nm compared to Device 5, the driving voltage at 1000 cd / m² increased by only 0.6 V. This means that the hole transport property of oYGTBiF(2) is excellent. Also, although the film thickness of the hole transport layer 812 of Device 6 was increased by 100 nm compared to Device 5, the driving voltage at 1000 cd / m² increased by only 0.6 V. This means that the hole transport property of oYGTBiF(2) is excellent. m thick, the driving voltage at 1000 cd / m² increased by only 0.6 V. 2 at 1000 cd / m² increased by only 0.6 V. This means that the hole transport property of oYGTBiF(2) is excellent.

[0393] Also, the emission spectrum when a current was passed through the light-emitting device at a current density of 12.5 mA / cm² is shown in Fig. 22. As shown in Fig. 22, Device 5 showed an emission spectrum having a maximum peak at around 458 nm due to the emission of 1,6BnfAPrn-03 contained in the light-emitting layer 813. Similarly, Device 6 showed an emission spectrum having a maximum peak at around 456 nm. 2 of the light-emitting device when a current was passed through at a current density of 12.5 mA / cm² is shown in Fig. 22. Fig. 22 shows the emission spectrum of the light-emitting device when a current was passed through at a current density of 12.5 mA / cm². As shown in Fig. 22, Device 5 showed an emission spectrum having a maximum peak at around 458 nm due to the emission of 1,6BnfAPrn-03 contained in the light-emitting layer 813. 6BnfAPrn-03 contained in the light-emitting layer 813. emission spectrum having a maximum peak at around 458 nm due to the emission of 1,6BnfAPrn-03 contained in the light-emitting layer 813. Similarly, Device 6 showed an emission spectrum having a maximum peak at around 456 nm. The spectrum was shown. Note that the optical distances related to light emission of Device 5 and Device 6 are slightly deviated from each other, and the emission chromaticity is deviated. This is because only the film thickness of oYGTBiF(2) was changed to evaluate the transport property of this material.

[0394] Next, a reliability test was conducted on the light-emitting device. The results of the reliability test are shown in FIG. 23. In FIG. 23(A), the vertical axis represents the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis represents the driving time (h). In FIG. 23(B), the vertical axis represents the voltage change (ΔV) from the voltage at the initial stage (when the driving time is 0 hour), and the horizontal axis represents the driving time (h). Note that in the reliability test, the current density was set to 50 mA / cm 2 to drive the light-emitting device.

[0395] From the results of the reliability test, it was found that both Device 5 and Device 6 show high reliability.

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

Example

[0397] In this example, a light-emitting device of one aspect of the present invention was fabricated and the evaluation results will be described.

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

[0399] The specific configurations of the two light-emitting devices used in this example are shown in Table 5. Note that the structure of Device 7 is the same as that of Device 1 (Fig. 11) except that the materials of the light-emitting layer 813 and the electron transport layer 814 are changed, and the structure of Device 8 is the same as that of Device 7 except that the film thickness of the hole transport layer 812 is increased. Therefore, for the manufacturing methods of Devices 7 and 8, reference can be made to Example 2 for the same parts as those of Device 1. Note that the structures of Devices 7 and 8 are the same as those of Device 1 (Fig. 11), and reference can be made to Example 2 for the manufacturing methods. In addition, the chemical formulas of the materials used in this example are shown below. For the same parts as those of Device 1, reference can be made to Example 2. Note that the structures of Devices 7 and 8 are the same as those of Device 1 (Fig. 11), and reference can be made to Example 2 for the manufacturing methods. For the same parts as those of Device 1, reference can be made to Example 2. Note that the structures of Devices 7 and 8 are the same as those of Device 1 (Fig. 11), and reference can be made to Example 2 for the manufacturing methods. In addition, the chemical formulas of the materials used in this example are shown below.

[0400]

Table 5

[0401]

Chemical formula

[0402] As shown in Table 5, in the light-emitting device of this example, in the light-emitting layer 813, as the host material, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) was used, and as the light-emitting material, 1,6BnfAPrn-03 was used. In addition, the electron transport layer 814 is 2-{4-[9,10-di(naphthalen-2-yl)-2 -Anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN ) and 8-hydroxyquinolinato-lithium (abbreviation: Liq) were co-evaporated and formed so that the weight ratio was 1:1 (=Z ADN:Liq) and the film thickness was 25 nm.

[0403] Also, as shown in Table 5, for Device 7 and Device 8, the film thicknesses of oY GTBiF(2) used in the hole transport layer 812 are different from each other.

[0404] ≪Operating Characteristics of Light-Emitting Device≫ The operating characteristics of the light-emitting device fabricated in this example were measured. The measurement was carried out at room temperature .

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

[0406] Table 6 shows the main initial characteristic values of the light-emitting device near 1000 cd / m 2 .

[0407]

Table 6

[0408] As shown in Figs. 24 to 27 and Table 6, it was found that Devices 7 and 8 have high luminous efficiency. Also, although the film thickness of the hole transport layer 812 of Device 8 was made 100 nm thicker than that of Device 7, the driving voltage at 1000 cd / m 2 only increased by 0.6 V. This means that the hole transport property of oYGTBiF(2) is excellent.

[0409] Also, when a current is passed through the light-emitting device at a current density of 12.5 mA / cm 2 , the emission spectrum is shown in FIG. 28. As shown in FIG. 28, device 7 has a maximum peak at around 458 nm due to the emission of 1, 6BnfAPrn-03 contained in the light-emitting layer 813, and shows an emission spectrum. Similarly, device 8 shows an emission spectrum with a maximum peak at around 456 nm. Note that the optical distances related to emission of device 7 and device 8 are slightly deviated, and the emission chromaticity is deviated. This is because only the film thickness of oYGTBiF(2) was changed to evaluate the transport property of this material.

[0410] Next, a reliability test was performed on the light-emitting device. The results of the reliability test are shown in FIG. 29. In FIG. 29(A), the vertical axis indicates the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis indicates the driving time (h). In FIG. 29(B), the vertical axis indicates the voltage change (ΔV) from the initial voltage (when the driving time is 0 h), and the horizontal axis indicates the driving time (h). Note that in the reliability test, the current density was set to 50 mA / cm

[0411]

[0412] 2 and the light-emitting device was driven.

[0413] From the results of the reliability test, it was found that both device 7 and device 8 show high reliability.

[0412] As shown in FIG. 29(B), the differences between the voltages after 380 hours and the initial voltages in device 7 and device 8 are both within 0.20 V, indicating that the voltage increase is small. From the above, it was found that even when the thickness of the hole transport layer using the organic compound of one embodiment of the present invention is increased, the driving voltage of the light-emitting device is not likely to increase.

[0413]

[0413]

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

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

[0415] [Chemical Formula]

[0416] (Synthesis of oYGTBi1BP) 1.4 g (4.2 mmol) of N-(4-biphenylyl)-2-biphenylamine and 1.8 g (4.2 mmol) of 9-(4''-chloro[1,1':4',1''-ter enyl]-4-yl)-9H-carbazole and 30 mg (84 μmol) of di-ter t-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (registered trademark: cBRIDP) were placed in a 200 mL three-necked flask equipped with a reflux tube, and the inside of the system was purged with nitrogen. . 0.81 g (8.4 mmol) of sodium tert-butoxide and 100 Xylene in mL was added, and degassing under reduced pressure and nitrogen substitution were each performed three times. 24 mg (42 μ mol) of bis(dibenzylideneacetone)palladium(0) was added to the system, and the mixture was stirred at 150 °C for 11 hours . After stirring, the insoluble matter was removed from the mixture by suction filtration. Water was added to the obtained filtrate, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water and then with saturated brine . The organic layer was dried over magnesium sulfate. The obtained mixture was filtered naturally to remove magnesium sulfate . The obtained filtrate was purified by filtration through alumina·celite (Wako Pure Chemical Industries, Ltd., Catalog number: 531-16855), and the obtained filtrate was concentrated, resulting in 2.3 g of a pale yellow solid. The obtained solid was purified by recrystallization (solvent used: a mixed solvent of toluene and hexane ), and 1.5 g of the pale yellow solid of the target product was obtained in a yield of 50%.

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

[0418]

Chemical formula

[0419] The analysis results of the obtained pale yellow solid by 1 1H-NMR are shown below. From these results, it was found that oY GTBi1BP was obtained.

[0420] 1 1H NMR (dichloromethane-d2, 300 MHz): δ = 8.16 (d, J = 8. 1 Hz, 2H), 7.90 (dd, J1 = 4.5 Hz, J2 = 1.8 Hz, 2H), 7. 77 (dd, J1 = 4.2 Hz, J2 = 2.1 Hz, 2H), 7.70 - 7.66 (m, 4H), 7.55 - 7.14 (m, 24H), 6.99 (d, J = 5.7 Hz, 2H), 6.96 (d, J = 5.7 Hz, 2H).

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

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

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

[0424] Also, CV measurement was repeated 100 times, and the oxidation - reduction wave in the 100th cycle measurement was compared with the oxidation - reduction wave in the first cycle to examine the

[0425] electrical stability of the compound. As a result, in the measurement of the oxidation potential Ea [V] of oYGTBi1BP, it was found that the HOMO level was -5.50 eV. On the other hand, in the measurement of the reduction potential Ec When comparing the waveforms at the first cycle and after 100 cycles, in the Ea measurement, 85 %, and in the Ec measurement, 94% of the peak intensity was maintained. Therefore, it was confirmed that oYGTBi1BP has very good resistance to oxidation and reduction.

[0426] In addition, the differential scanning calorimetry (DSC measurement) of oYGTBi1BP was measured using Pyris1DSC manufactured by PerkinElmer. The differential scanning calorimetry was performed by heating from -10°C to 380°C at a heating rate of 40°C / min and then holding at the same temperature for 1 minute and then cooling to -10°C at a cooling rate of 10 0°C / min for two consecutive times. From the DSC measurement results of the second cycle, it was revealed that the glass transition temperature of oYGTBi1BP is 122°C and it was shown that it is a substance with very high heat resistance.

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

[0428] <Synthesis of <YGTBiF(2)>> 2.0 g (4.0 mmol) of 2-amino-N-[(1,1'-biphenyl)-4-yl -N-(4-bromophenyl)-9,9-dimethylfluorene, 1.4 g (4.0 m mol) of [4'-(carbazol-9-yl)-4-biphenylyl]boronic acid, 24 mg (76 μmol) of tri(ortho-tolyl)phosphine, 5 mL of 2M potassium carbonate aqueous solution, 30 mL of toluene, and 10 mL of ethanol L were placed in a 200 with a reflux tube attached. It was placed in a 100 mL three-necked flask. After degassing the mixture under reduced pressure, the system was purged with nitrogen. This mixture was heated at 60 °C, and 8.9 mg (40 μmol) of palladium(II) acetate was added to this mixture. The mixture was refluxed for 10 hours. The resulting mixture was suction filtered. The obtained filtrate was added with water, and the aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined and washed with saturated brine, and dried over magnesium sulfate. The filtrate obtained by natural filtration of this mixture was concentrated to obtain a light brown solid. This solid was purified by high performance liquid chromatography (HPLC)( mobile phase: chloroform), and 1.3 g of a pale yellow solid of the target product was obtained in a yield of 4 3%.

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

[0430]

Chemical formula

[0431] The analysis results of the obtained pale yellow solid by 1 1H-NMR are shown below. From these results, it was found that YG TBiF(2) was obtained.

[0432] 1 1H NMR (dichloromethane-d2, 300 MHz): δ = 8.17 (d, J = 7. 8 Hz, 2H), 7.92 (d, J = 8.7 Hz, 2H), 7.75 (dd, J1 = 27 .6Hz, J2=9.0Hz, 4H), 7.70-7.61(m, 8H), 7.56(d , J=9.0Hz, 2H), 7.52-7.42(m, 7H), 7.36-7.24(m , 10H), 7.14(dd, J1=6.0Hz, J2=2.1Hz, 1H), 1.45 (s, 6H).

[0433] Next, the absorption and emission spectra of the toluene solution and solid thin film of YGTBiF(2) were The measurement conditions were the same as in Example 1, and therefore will not be repeated.

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

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

[0436] In addition, the CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was The electrical stability of the compounds was examined by comparing the oxidation-reduction waves in the first cycle.

[0437] As a result, in the measurement of the oxidation potential Ea [V] of YGTBiF(2), the HOMO level was - On the other hand, in the measurement of the reduction potential Ec [V], LUM The O level was found to be -2.34 eV. In addition, the repeated measurement of the oxidation-reduction wave When comparing the waveforms after the first and 100th cycles, the Ea measurement showed %, Since it maintained 96% peak intensity in the Ec measurement, YGTBiF(2) was confirmed to have very good resistance to oxidation and reduction.

[0438] Also, the differential scanning calorimetry (DSC measurement) of YGTBiF(2) was measured using a Pyris1 DSC manufactured by PerkinElmer . The differential scanning calorimetry was heated from -10°C to 330°C at a heating rate of 40°C / min , held at the same temperature for 1 minute, and then cooled to -10°C at a cooling rate of 10 0°C / min for two consecutive cycles. From the DSC measurement results of the second cycle, it became clear that the glass transition point of YGTBiF(2) was 145°C , indicating that it is a substance with very high heat resistance.

[0439] Also, differential thermal analysis of YGTBiF(2) was performed. The measurement method was the same as in Example 1, so it is omitted . In thermogravimetric measurement - differential thermal analysis, the temperature at which the weight obtained from the thermogravimetric measurement becomes -5 % of the starting weight (decomposition temperature) was found to be 499°C, indicating that it is a substance with high heat resistance .

Description of Symbols

[0440] 101 First electrode 102 Second electrode 103 EL layer 103a EL layer 103b EL layer 103c EL layer 104 Charge generation layer 111 Hole injection layer 112 Hole transport layer 113 Light - emitting layer 114 Electron transport layer 115 Electron injection layer 201 Substrate 202 Insulating layer Insulating layer 202a Insulating layer 202b Light-emitting device 203B Light-emitting device 203G Light-emitting device 203R Light-emitting device 203W Insulating layer 204 Substrate 205 Color filter 206B Color filter 206G Color filter 206R Space 207 Adhesive layer 208 Black matrix 209 Transistor 210 First electrode 211 Conductive layer 212G Conductive layer 212R EL layer 213 EL layer 213B EL layer 213G EL layer 213R Second electrode 215 Optical distance 220B Optical distance 220G Optical distance 220R First substrate 301 Pixel portion 302 Circuit portion 303 Circuit portion 304a Circuit portion 304b Sealing material 305 Second substrate 306 Wiring 307 FPC 308 Transistor 309 Transistor 310 Transistor 311 Transistor 312 First electrode 313 Insulating layer 314 EL layer 315 Second electrode 316 Organic EL device 317 318 Space 320 Transistor 321 Conductive layer 322a Conductive layer 322b Conductive layer 323 Conductive layer 324 Insulating layer 325 Insulating layer 326 Insulating layer 327 Semiconductor layer 327i Channel formation region 327n Low resistance region 328 Insulating layer 330 Transistor 331 Conductive layer 332a Conductive layer 332b Conductive layer 333 Conductive layer 334 Insulating layer 335 Insulating layer 337 Semiconductor layer 338 Insulating layer 401 First electrode 402 EL layer 403 Second electrode 405 Insulating layer 406 Conductive layer 407 Adhesive layer 416 Conductive layer 420 Substrate 422 Adhesive layer 423 Barrier layer 424 Insulating layer 450 Organic EL device 490a Substrate 490b Substrate 490c Barrier layer 800 Substrate 801 First electrode 802 EL layer 803 Second electrode 811 Hole injection layer 812 Hole transport layer 813 Light emitting layer 814 Electron transport layer 815 Electron injection layer 911 Housing 912 Light source 913 Detection stage 914 Imaging device 915 Light emitting part 916 Light emitting part 917 Light emitting part 921 Housing 922 Operation button 923 Detection part 924 Light source 925 Imaging device 931 Housing 932 Operation panel 933 Conveyor mechanism 934 Monitor 935 Detection unit 936 Member to be inspected 937 Imaging device 938 Light source 981 Housing 982 Display part 983 Operation button 984 External connection port 985 Speaker 986 Microphone 987 First camera 988 Second camera 7000 Display part 7001 Display part 7100 Television device 7101 Housing 7103 Stand 7111 Remote control operation unit 7200 Notebook personal computer 7211 Housing 7212 Keyboard 7213 Pointing device 7214 External connection port 7300 Digital signage 7301 Housing 7303 Speaker 7311 Information terminal device 7400 Digital signage 7401 Column 7411 Information terminal device 7600 Portable information terminal 7601 Housing 7602 Hinge 7650 Portable Information Terminal 7651 Non-display Part 7800 Portable Information Terminal 7801 Band 7802 Input / Output Terminal 7803 Operation Button 7804 Icon 7805 Battery 9700 Automobile 9701 Vehicle Body 9702 Wheel 9703 Windshield 9704 Light 9705 Fog Lamp 9710 Display Part 9711 Display Part 9712 Display Part 9713 Display Part 9714 Display Part 9715 Display Part 9721 Display Part 9722 Display Part 9723 Display Part

Claims

1. A light-emitting device having a first layer containing an organic compound represented by the general formula (G0) and an acceptor material between a pair of electrodes. 【Chemical Formula 1】 (wherein, R １ ~R ５ represents any one of the general formula (A), and the others each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, R ６ ~R １３ , R ２１ ~R ２９ , R ３１ ~R ３９ , and R ４１ ~R ４８ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and R ２１ and R ２２ may be bonded to each other to form a spiro ring. )

2. A light-emitting device having a first layer containing an organic compound represented by the general formula (G1) and an acceptor material between a pair of electrodes. 【Chemical Formula 2】 (wherein, R ２ to R １３ , R ２１ to R ２９ , R ３１ to R ３９ , and R ４１ to R ４８ each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and R ２１ and R ２２ may be bonded to each other to form a spiro ring.)

3. In Claim 1 or 2, R ３５ ~R ３９ A light-emitting device, wherein any one of R to R represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

4. In any one of Claims 1 to 3, R ２１ and R ２２ are the same and represent an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group, a light-emitting device.

5. In Claim 4, R ２１ and R ２２ both represent a methyl group, a light-emitting device.

6. In Claim 4, R ２１ and R ２２ are both phenyl groups without substitution, a light-emitting device.

7. In any one of Claims 1 to 3, R ２１ and R ２２ are a light-emitting device that are combined with each other to form a spiro ring.

8. In Claim 7, R ２１ and R ２２ each represent a substituted or unsubstituted phenyl group, and a light-emitting device in which the phenyl groups are bonded to each other to form a spirobifluorene ring.

9. In any one of Claims 1 to 8, R ４１ to R ４８ each independently represents a hydrogen, methyl group, tert-butyl group, or substituted or unsubstituted phenyl group, a light-emitting device.

10. In any one of Claims 1 to 9, The acceptor material is an organic acceptor, the light-emitting device.

11. In any one of Claims 1 to 10, The acceptor material has at least one of a halogen group and a cyano group, the light-emitting device.

12. In any one of Claims 1 to 11, The first layer is a hole injection layer, the light-emitting device.

13. The light-emitting device according to any one of Claims 1 to 12, and At least one of a transistor and a substrate, a light-emitting device having.

14. The light-emitting device according to Claim 13, and At least one of a connector and an integrated circuit, a light-emitting module having.

15. The light-emitting device according to Claim 13, and At least one of an antenna, a battery, a housing, a camera, a speaker, a microphone, and an operation button, an electronic device having.

16. The light-emitting device according to any one of Claims 1 to 12, and At least one of a housing, a cover, and a support base, a lighting device having.

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