JPWO2018178818A1 - Organic compounds, light-emitting elements, light-emitting devices, electronic devices, and lighting devices - Google Patents

Abstract

Provide a new organic compound. That is, the present invention provides a novel organic compound that is effective in improving device characteristics and reliability. An organic compound having a condensed ring structure in the carbazole skeleton and represented by the following general formula (G1). However, it includes those which form a ring in which the substituent of the dibenzocarbazole group is condensed with the carbazole skeleton.

Description

One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. Note that one embodiment of the present invention is not limited to the above technical field. That is, one embodiment of the present invention relates to an object, a method, a manufacturing method, or a driving method. Alternatively, one embodiment of the present invention relates to a process, a machine, a manufacture, or a composition (composition of matter). Specifically, a semiconductor device, a display device, a liquid crystal display device, and the like can be given as examples.

A light-emitting element (also referred to as an organic EL element) in which an EL layer is interposed between a pair of electrodes has characteristics such as thin and lightweight, high-speed response to an input signal, and low power consumption. , As a next-generation flat panel display.

In a light-emitting element, when a voltage is applied between a pair of electrodes, electrons and holes injected from each electrode are recombined in an EL layer, and a light-emitting substance (organic compound) contained in the EL layer is brought into an excited state. Light is emitted when the excited state returns to the ground state. Note that the types of excited states include a singlet excited state (S ^* ) and a triplet excited state (T ^* ). Light emission from the singlet excited state is fluorescence, and light emission from the triplet excited state is phosphorescence. being called. Further, it is considered that their statistical generation ratio in the light emitting element is S ^* : T ^* = 1: 3. An emission spectrum obtained from a light-emitting substance is peculiar to the light-emitting substance, and light-emitting elements of various colors can be obtained by using different kinds of organic compounds as the light-emitting substance.

With respect to such a light emitting element, improvement of the element structure, development of materials, and the like have been actively performed in order to improve the element characteristics (for example, see Patent Document 1).

JP 2010-182699 A

In the development of a light-emitting element, an organic compound used for the light-emitting element is very important for enhancing its characteristics. Thus, one embodiment of the present invention provides a novel organic compound. That is, the present invention provides a novel organic compound that is effective in improving device characteristics and reliability. Another embodiment of the present invention provides a novel organic compound that can be used for a light-emitting element. Another embodiment of the present invention provides a novel organic compound that can be used for an EL layer of a light-emitting element. Further, a highly efficient and highly reliable new light-emitting element using a novel organic compound which is one embodiment of the present invention is provided. Further, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. Note that the description of these objects does not disturb the existence of other objects. Note that one embodiment of the present invention does not necessarily need to solve all of these problems. It should be noted that issues other than these are naturally evident from the description of the specification, drawings, claims, etc., and that other issues can be extracted from the description of the specifications, drawings, claims, etc. It is.

One embodiment of the present invention is an organic compound having a condensed ring structure in a carbazole skeleton and represented by General Formula (G1) below.

Note that in the general formula (G1), Ar ¹ represents a substituted or unsubstituted phenylene group. Further, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, or a substituted or unsubstituted 7 to 7 carbon atoms. Represents a polycyclic saturated hydrocarbon having 10 or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted 6 carbon atoms To 13 aryl groups.

Another embodiment of the present invention is an organic compound represented by General Formula (G2) below.

Note that in the general formula (G2), Ar ² represents an unsubstituted phenylene group. Further, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, or a substituted or unsubstituted 7 to 7 carbon atoms. Represents a polycyclic saturated hydrocarbon having 10 or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted 6 carbon atoms To 13 aryl groups.

Another embodiment of the present invention is an organic compound represented by General Formula (G3) below.

In the general formula (G3), R ^{1 to} R ²¹ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted 6 carbon atoms To 13 aryl groups.

Another embodiment of the present invention is an organic compound represented by General Formula (G4) below.

In General Formula (G4), R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Further, at least one of R ⁹ and R ¹⁰ and R ¹¹ and R ¹² is condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 6 carbon atoms as a substituent. An alkyl group, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted 6 to 6 carbon atoms It has any of the thirteen aryl groups.

The above-described organic compound of one embodiment of the present invention has a condensed ring structure in a carbazole skeleton. Specifically, it has a structure in which one benzene ring forming the carbazole skeleton is condensed at two or more positions. Note that having such a structure has a feature that when used in combination with a guest material (dopant), energy can be efficiently transferred to the dopant. Further, in the case where the arylene group bonded to the nitrogen of the carbazole skeleton is an unsubstituted phenylene group, steric hindrance in the molecule can be prevented, so that it can be easily synthesized.

Another embodiment of the present invention is an organic compound represented by a structural formula (100), a structural formula (101), a structural formula (102), or a structural formula (103).

Another embodiment of the present invention is a light-emitting element using an organic compound having a condensed ring structure in a carbazole skeleton. Note that a light-emitting element including a guest material in addition to the above organic compound is also included in the present invention.

Another embodiment of the present invention is a light-emitting element using the above-described organic compound of one embodiment of the present invention. Note that a light-emitting element formed using an organic compound of one embodiment of the present invention for an EL layer provided between a pair of electrodes or a light-emitting layer included in the EL layer is also included in the present invention. Further, a light-emitting device including a transistor, a substrate, or the like in addition to the light-emitting element is also included in the category of the invention. Further, in addition to these light-emitting devices, an electronic device or a lighting device including a microphone, a camera, an operation button, an external connection portion, a housing, a cover, a support base, a speaker, or the like is also included in the scope of the invention.

Further, one embodiment of the present invention includes a light-emitting device including a light-emitting element, and further includes a lighting device including the light-emitting device. Therefore, a light-emitting device in this specification refers to an image display device or a light source (including a lighting device). In addition, a module in which a connector such as FPC (Flexible Printed Circuit) or TCP (Tape Carrier Package) is attached to the light emitting device, a module in which a printed wiring board is provided at the tip of TCP, or a COG (Chip On) in the light emitting element. All the modules on which an IC (integrated circuit) is directly mounted by the Glass method are included in the light emitting device.

One embodiment of the present invention can provide a novel organic compound. That is, it is possible to provide a novel organic compound that is effective in improving device characteristics. According to one embodiment of the present invention, a novel organic compound that can be used for a light-emitting element can be provided. According to one embodiment of the present invention, a novel organic compound that can be used for an EL layer of a light-emitting element can be provided. Further, a highly efficient and highly reliable novel light-emitting element using a novel organic compound which is one embodiment of the present invention can be provided. Further, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. Note that the description of these effects does not disturb the existence of other effects. Note that one embodiment of the present invention does not necessarily need to have all of these effects. It should be noted that effects other than these are obvious from the description of the specification, drawings, claims, etc., and other effects can be extracted from the description of the specification, drawings, claims, etc. It is.

FIG. 4 illustrates a structure of a light-emitting element. FIG. 4 illustrates a light-emitting device. FIG. 4 illustrates a light-emitting device. 7A to 7C illustrate electronic devices. 7A to 7C illustrate electronic devices. FIG. 4 illustrates a car. FIG. 3 illustrates a lighting device. FIG. 3 illustrates a lighting device. ¹ H-NMR chart of an organic compound represented by Structural Formula (100). 27 shows an ultraviolet-visible absorption spectrum and an emission spectrum of an organic compound represented by Structural Formula (100). ¹ H-NMR chart of an organic compound represented by Structural Formula (101). 8 shows an ultraviolet-visible absorption spectrum and an emission spectrum of an organic compound represented by Structural Formula (101). FIG. 4 illustrates a light-emitting element. FIG. 13 shows current density-luminance characteristics of Light-emitting Elements 1 and 2. FIG. 6 illustrates voltage-luminance characteristics of Light-emitting Elements 1 and 2. 7A and 7B illustrate luminance-current efficiency characteristics of Light-emitting Elements 1 and 2. FIG. 7 illustrates voltage-current characteristics of Light-emitting Elements 1 and 2. FIG. 9 shows emission spectra of Light-emitting Element 1, Light-emitting Element 2, and Comparative Light-Emitting Element 3. FIG. 5 is a diagram illustrating reliability of a light-emitting element 1 and a comparative light-emitting element 3. ¹ H-NMR chart of an organic compound represented by Structural Formula (102). 29 shows an ultraviolet-visible absorption spectrum and an emission spectrum of an organic compound represented by Structural Formula (102). ¹ H-NMR chart of an organic compound represented by Structural Formula (103). 27 shows an ultraviolet-visible absorption spectrum and an emission spectrum of an organic compound represented by Structural Formula (103). FIG. 14 illustrates current density-luminance characteristics of the light-emitting element 4. FIG. 4 is a graph showing voltage-luminance characteristics of a light-emitting element 4. FIG. 13 shows luminance-current efficiency characteristics of the light-emitting element 4. FIG. 4 shows voltage-current characteristics of a light-emitting element 4. FIG. 14 shows an emission spectrum of the light-emitting element 4. FIG. 9 is a diagram illustrating reliability of the light-emitting element 4.

Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it is possible to variously change the form and details without departing from the spirit and scope of the present invention. Therefore, the present invention is not construed as being limited to the description of the embodiments below.

Note that the position, size, range, or the like of each component illustrated in drawings and the like is not accurately represented in some cases for easy understanding. Therefore, the disclosed invention is not necessarily limited to the position, size, range, or the like disclosed in the drawings and the like.

In this specification and the like, when describing the structure of the present invention with reference to the drawings, the same reference numerals are used in common in different drawings.

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

Note that the organic compound described in this embodiment has a structure represented by the following general formula (G1) in which a carbazole skeleton has a condensed ring structure.

Note that in the general formula (G1), Ar ¹ represents a substituted or unsubstituted phenylene group. Further, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, or a substituted or unsubstituted 7 to 7 carbon atoms. Represents a polycyclic saturated hydrocarbon having 10 or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted 6 carbon atoms To 13 aryl groups.

The organic compound described in this embodiment is represented by the following general formula (G2).

Note that in the general formula (G2), Ar ² represents an unsubstituted phenylene group. Further, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, or a substituted or unsubstituted 7 to 7 carbon atoms. Represents a polycyclic saturated hydrocarbon having 10 or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted 6 carbon atoms To 13 aryl groups.

The organic compound described in this embodiment is represented by the following general formula (G3).

In the general formula (G3), R ^{1 to} R ²¹ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted 6 carbon atoms To 13 aryl groups.

The organic compound described in this embodiment is represented by the following general formula (G4).

In General Formula (G4), R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, It represents either an unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Further, at least one of R ⁹ and R ¹⁰ and R ¹¹ and R ¹² is condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 6 carbon atoms as a substituent. An alkyl group, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted 6 to 6 carbon atoms It has any of the thirteen aryl groups.

In the above general formulas (G1) to (G4), a substituted or unsubstituted phenylene group, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted 7 carbon atoms When any one of 10 to 10 polycyclic saturated hydrocarbons or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms has a substituent, the substituent is a methyl group, an ethyl group, a propyl group, or an isopropyl group. Group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, alkyl group having 1 to 6 carbon atoms such as hexyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 8,9, A cycloalkyl group having 5 to 7 carbon atoms such as a 10-trinorbornanyl group, an aryl group having 6 to 12 carbon atoms such as a phenyl group, a naphthyl group, and a biphenyl group; And the like.

Specific examples of the alkyl group having 1 to 6 carbon atoms in the general formulas (G1) to (G4) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2 -Dimethylbutyl group, 2,3-dimethylbutyl group and the like.

Specific examples of the monocyclic saturated hydrocarbon having 5 to 7 carbon atoms in the general formulas (G1) to (G4) include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a 2-methylcyclohexyl group. Can be

Specific examples of the polycyclic saturated hydrocarbon having 7 to 10 carbon atoms in the general formulas (G1) to (G4) include an 8,9,10-trinorbornanyl group, a decahydronaphthyl group, and an adamantyl group. And the like.

Specific examples of the aryl group having 6 to 13 carbon atoms in the general formulas (G1) to (G4) include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, and an o-group. Examples include a biphenyl group, an m-biphenyl group, a p-biphenyl group, a 1-naphthyl group, a 2-naphthyl group, and a fluorenyl group.

The organic compound of one embodiment of the present invention represented by any of the general formulas (G1) to (G4) has a condensed ring structure in the carbazole skeleton. Specifically, it has a structure in which one benzene ring forming the carbazole skeleton is condensed at two or more positions. Note that having such a structure has a feature that when used in combination with a guest material (dopant), energy can be efficiently transferred to the dopant. Further, when the arylene group bonded to the nitrogen of the carbazole skeleton is an unsubstituted phenylene group, steric hindrance in the molecule can be particularly prevented, and the compound can be easily synthesized.

Next, specific structural formulas of the organic compound which is one embodiment of the present invention are described below. However, the present invention is not limited to these.

Note that the organic compound represented by any of the structural formulas (100) to (144) is an example of the organic compound represented by the general formula (G1), and the organic compound according to one embodiment of the present invention includes Not limited.

Next, an example of a method for synthesizing the organic compound represented by the general formula (G1) will be described.

<< Method of Synthesizing Organic Compound Represented by General Formula (G1) >>
First, an example of a method for synthesizing an organic compound represented by General Formula (G1) below will be described.

In General Formula (G1), Ar ¹ represents a substituted or unsubstituted phenylene group. Further, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, or a substituted or unsubstituted 7 to 7 carbon atoms. Represents a polycyclic saturated hydrocarbon having 10 or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted 6 carbon atoms To 13 aryl groups.

The organic compound represented by the general formula (G1) can be synthesized by a synthesis scheme (A-1) shown below. That is, the heterocyclic compound derivative (a1) and the halide (a2) of the anthracene derivative are coupled with a metal catalyst, a metal, or a metal compound in the presence of a base, whereby the compound is represented by the general formula (G1). Organic compounds can be obtained.

In the synthesis scheme (A-1), Ar ¹ represents a substituted or unsubstituted phenylene group. X represents a halogen. Further, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, or a substituted or unsubstituted 7 to 7 carbon atoms. Represents a polycyclic saturated hydrocarbon having 10 or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has 1 to 1 carbon atoms as a substituent. 6 alkyl groups, substituted or unsubstituted monocyclic saturated hydrocarbons having 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons having 7 to 10 carbon atoms, or substituted or unsubstituted 6 carbon atoms To 13 aryl groups.

In the above synthesis scheme (A-1), when performing a Hartwick-Buchwald reaction, X represents a halogen or a triflate group. As the halogen, iodine, bromine or chlorine is preferable. In this reaction, a palladium complex or a palladium compound such as bis (dibenzylideneacetone) palladium (0) or palladium (II) acetate, and tri (tert-butyl) phosphine or tri (n-hexyl) phosphine coordinated thereto. And a palladium catalyst using a ligand such as tricyclohexylphosphine. Examples of the base include an organic base such as sodium tert-butoxide and an inorganic base such as potassium carbonate. When a solvent is used, toluene, xylene, benzene, tetrahydrofuran, or the like can be used.

In the synthesis scheme (A-1), when performing an Ullmann reaction, X represents halogen. As the halogen, iodine, bromine or chlorine is preferable. Copper or a copper compound is used as the catalyst. When a copper compound is used as the catalyst, R ²² and R ²³ in the formula (A-1) each represent a halogen, an acetyl group, or the like, and examples of the halogen include chlorine, bromine, and iodine. In addition, it is preferable to use copper (I) iodide which is iodine or copper (II) acetate in which R ²³ is an acetyl group as R ²² . Examples of the base used include inorganic bases such as potassium carbonate. As the solvent, 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidinone (DMPU), toluene, xylene, benzene, or the like is used. However, the solvent is not limited to these. In the Ullmann reaction, when the reaction temperature is 100 ° C. or higher, the desired product can be obtained in a shorter time and in a higher yield. Therefore, it is preferable to use DMPU or xylene having a high boiling point. Since the reaction temperature is more preferably higher than 150 ° C., DMPU is more preferably used.

As described above, the method for synthesizing the organic compound represented by General Formula (G1) has been described. However, the present invention is not limited to this, and may be synthesized by another synthesis method.

Note that since the above-described organic compound of one embodiment of the present invention has an electron-transport property and a hole-transport property, it can be used as a host material of a light-emitting layer or as an electron-transport layer or a hole-transport layer. Further, it is preferable to use as a host material in combination with a substance that emits fluorescence (fluorescent material). Further, since it emits fluorescent light, it can itself be used as a light-emitting substance of a light-emitting element. Therefore, a light-emitting element including any of these organic compounds is also one embodiment of the present invention.

With the use of the organic compound of one embodiment of the present invention, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency can be realized. Further, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with low power consumption can be provided.

Note that in this embodiment, one embodiment of the present invention has been described. Another embodiment of the present invention will be described in another embodiment. Note that one embodiment of the present invention is not limited thereto. That is, since various embodiments of the present invention are described in this embodiment and other embodiments, one embodiment of the present invention is not limited to a specific embodiment.

The structure described in this embodiment can be used in appropriate combination with any of the structures described in the other embodiments.

(Embodiment 2)
In this embodiment, a light-emitting element using the organic compound described in Embodiment 1 will be described with reference to FIGS.

基本 Basic structure of light emitting device 素 子
First, the basic structure of the light emitting element will be described. FIG. 1A illustrates a light-emitting element having an EL layer including a light-emitting layer between a pair of electrodes. Specifically, it has a structure in which an EL layer 103 is interposed between a first electrode 101 and a second electrode 102.

In FIG. 1B, a plurality of (two layers in FIG. 1B) EL layers (103a and 103b) are provided between a pair of electrodes, and a charge generation layer 104 is provided between the EL layers. 1 shows a light-emitting element having a stacked structure (tandem structure). A light-emitting element having a tandem structure can realize a light-emitting device which can be driven at low voltage and consumes low power.

When a voltage is applied to the first electrode 101 and the second electrode 102, the charge generation layer 104 injects electrons into one EL layer (103a or 103b) and charges the other EL layer (103b or 103a). It has a function of injecting holes. Therefore, in FIG. 1B, when a voltage is applied to the first electrode 101 so that the potential is higher than that of the second electrode 102, electrons are injected from the charge generation layer 104 to the EL layer 103a and the EL layer 103b Holes are injected into the holes.

Note that the charge generation layer 104 has a property of transmitting visible light from the viewpoint of light extraction efficiency (specifically, the transmittance of visible light to the charge generation layer 104 is 40% or more). preferable. Further, the charge generation layer 104 functions even if it has lower conductivity than the first electrode 101 and the second electrode 102.

FIG. 1C illustrates a stacked structure of the EL layer 103 of the light-emitting element which is one embodiment of the present invention. However, in this case, the first electrode 101 functions as an anode. The EL layer 103 has a structure in which a hole (hole) injection layer 111, a hole (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. Having. Note that even in the case where a plurality of EL layers are provided as in the tandem structure illustrated in FIG. 1B, the EL layers are sequentially stacked from the anode side as described above. When the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order is reversed.

The light-emitting layers 113 included in the EL layers (103, 103a, and 103b) each include a light-emitting substance or a plurality of substances as appropriate, and have a structure in which fluorescent light emission or phosphorescent light emission having a desired emission color can be obtained. be able to. Further, the light-emitting layer 113 may have a stacked structure of different emission colors. Note that in this case, a different material may be used for a light-emitting substance and other substances used for the stacked light-emitting layers. Further, a structure in which different emission colors can be obtained from the plurality of EL layers (103a and 103b) illustrated in FIG. Also in this case, the light-emitting substance used for each light-emitting layer and other substances may be different materials.

In the light-emitting element of one embodiment of the present invention, for example, the first electrode 101 illustrated in FIG. 1C is used as a reflective electrode, the second electrode 102 is used as a semi-transmissive / semi-reflective electrode, With a (microcavity) structure, light emission obtained from the light-emitting layer 113 included in the EL layer 103 can be resonated between both electrodes, so that light emission obtained from the second electrode 102 can be increased.

Note that in the case where the first electrode 101 of the light-emitting element is a reflective electrode having a stacked structure of a conductive material having a reflective property and a conductive material having a light-transmitting property (a transparent conductive film), The optical adjustment can be performed by controlling the thickness. Specifically, for a wavelength λ of light obtained from the light-emitting layer 113, the distance between the first electrode 101 and the second electrode 102 is close to mλ / 2 (where m is a natural number). It is preferable to adjust as follows.

In order to amplify desired light (wavelength: λ) obtained from the light-emitting layer 113, the optical distance from the first electrode 101 to a region (light-emitting region) of the light-emitting layer where desired light is obtained, The optical distance from the electrode 102 to the region (light-emitting region) of the light-emitting layer 113 where desired light is obtained is adjusted to be close to (2m ′ + 1) λ / 4 (where m ′ is a natural number). Is preferred. Note that the light-emitting region here refers to a region in the light-emitting layer 113 where holes and electrons recombine.

By performing such optical adjustment, the spectrum of the specific monochromatic light obtained from the light emitting layer 113 can be narrowed, and light emission with high color purity can be obtained.

However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 is strictly defined as the total thickness from the reflection area of the first electrode 101 to the reflection area of the second electrode 102. it can. However, since it is difficult to strictly determine the reflection region in the first electrode 101 and the second electrode 102, it is assumed that an arbitrary position between the first electrode 101 and the second electrode 102 is a reflection region. Can sufficiently obtain the above-described effects. Strictly speaking, the optical distance between the first electrode 101 and the light-emitting layer from which desired light is obtained is determined by 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 is obtained. It can be said that it is distance. However, it is difficult to strictly 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. It is assumed that the above-mentioned effect can be sufficiently obtained by assuming an arbitrary position of the light emitting layer from which light is obtained as a light emitting region.

Since the light-emitting element illustrated in FIG. 1C has a microcavity structure, light with different wavelengths (monochromatic light) can be extracted even when the light-emitting element has the same EL layer. Therefore, it is not necessary to apply different colors (for example, RGB) for obtaining different emission colors. Therefore, it is easy to realize high definition. Further, a combination with a coloring layer (color filter) is also possible. Further, the emission intensity of the specific wavelength in the front direction can be increased, so that power consumption can be reduced.

The light-emitting element illustrated in FIG. 1E is an example of the tandem light-emitting element illustrated in FIG. 1B and includes three EL layers (103a, 103b, and 103c) as illustrated in FIG. (104a, 104b). Note that each of the three EL layers (103a, 103b, 103c) has a light emitting layer (113a, 113b, 113c), and the light emitting colors of each light emitting layer can be freely combined. For example, the light emitting layer 113a can be blue, the light emitting layer 113b can be red, green, or yellow, and the light emitting layer 113c can be blue, but the light emitting layer 113a is red, and the light emitting layer 113b is blue, green, or yellow. , The light emitting layer 113c may be red.

Note that in the above light-emitting element of one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (a transparent electrode, a semi-transmissive / semi-reflective electrode, or the like). I do. When the light-transmitting electrode is a transparent electrode, the transparent electrode has a visible light transmittance of 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the reflectance of the semi-transmissive / semi-reflective electrode for visible light is 20% or more and 80% or less, preferably 40% or more and 70% or less. It is preferable that these electrodes have a resistivity of 1 × 10 ⁻² Ωcm or less.

In the above-described light-emitting element of one embodiment of the present invention, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (a reflective electrode), the visible light of the reflective electrode The light reflectance is 40% to 100%, preferably 70% to 100%. The electrode preferably has a resistivity of 1 × 10 ⁻² Ωcm or less.

<< Specific structure and manufacturing method of light emitting element >>
Next, a specific structure and a manufacturing method of a light-emitting element which is one embodiment of the present invention will be described with reference to FIGS. Here, a light-emitting element having a tandem structure and a microcavity structure illustrated in FIG. 1B is also described with reference to FIG. In the case where the light-emitting element illustrated in FIG. 1D has a microcavity structure, the first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a transflective electrode. Therefore, a single electrode or a plurality of desired electrode materials can be used to form a single layer or a stacked layer. Note that after the EL layer 103b is formed, the second electrode 102 is formed by selecting a material in the same manner as described above. Further, these electrodes can be manufactured by a sputtering method or a vacuum evaporation method.

<First electrode and second electrode>
As a material for forming the first electrode 101 and the second electrode 102, any of the following materials can be used in an appropriate combination as long as the functions of both electrodes described above can be satisfied. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used as appropriate. Specifically, an In-Sn oxide (also referred to as ITO), an In-Si-Sn oxide (also referred to as ITSO), an In-Zn oxide, and an In-W-Zn oxide are given. 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 an appropriate combination of these metals. In addition, elements belonging to Group 1 or Group 2 of the periodic table (for example, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), and ytterbium, which are not exemplified above. Rare earth metals such as (Yb), alloys containing an appropriate combination thereof, graphene, and the like can be used.

In the light-emitting element illustrated in FIG. 1D, when the first electrode 101 is an anode, a hole injection layer 111a and a hole transport layer 112a of an EL layer 103a are sequentially formed over the first electrode 101 by a vacuum evaporation method. It is formed by lamination. After the EL layer 103a and the charge generation layer 104 are formed, the hole injection layer 111b and the hole transport layer 112b of the EL layer 103b are sequentially stacked on the charge generation layer 104 in the same manner.

<Hole injection layer and hole transport layer>
The hole injection layers (111, 111a, 111b) are layers that inject holes (holes) from the first electrode 101 or the intermediate layer (104) as an anode to the EL layers (103, 103a, 103b). This is a layer containing a material having a high hole-injection property.

Examples of the material having a high hole-injecting property include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. In addition, phthalocyanine-based compounds such as phthalocyanine (abbreviation: H ₂ Pc) and copper phthalocyanine (abbreviation: CuPC), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl ( Abbreviation: DPAB), N, N'-bis {4- [bis (3-methylphenyl) amino] phenyl} -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine ( An aromatic amine compound such as DNTPD, or a polymer such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS) can be used.

As a material having a high hole-injection property, a composite material containing a hole-transport material and an acceptor material (an electron-accepting material) can also be used. In this case, electrons are extracted from the hole transporting material by the acceptor material, holes are generated in the hole injection layers (111, 111a, 111b), and the holes are generated through the hole transporting layers (112, 112a, 112b). Holes are injected into the light emitting layers (113, 113a, 113b). Note that the hole injecting layers (111, 111a, 111b) may be formed as a single layer of a composite material containing a hole transporting material and an acceptor material (electron accepting material). The material and the acceptor material (electron-accepting material) may be formed by laminating them in different layers.

The hole transport layers (112, 112a, 112b) transport holes injected from the first electrode 101 to the light emitting layers (113, 113a, 113b) by the hole injection layers (111, 111a, 111b). Layer. Note that the hole transporting layers (112, 112a, 112b) are layers containing a hole transporting material. As the hole transporting material used for the hole transporting layers (112, 112a, 112b), a material having a HOMO level equal to or close to the HOMO level of the hole injecting layers (111, 111a, 111b) is particularly preferable. Is preferred.

As the acceptor material used for the hole-injection layers (111, 111a, and 111b), an oxide of a metal belonging to Group 4 to Group 8 of the periodic table can be used. Specifically, examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, an organic acceptor such as a quinodimethane derivative, a chloranil derivative, and a hexaazatriphenylene derivative can be used. Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F ₄ -TCNQ), chloranil, 2,3,6,7,10,11 -Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) or the like can be used.

As the hole transporting material used for the hole injection layers (111, 111a, 111b) and the hole transporting layers (112, 112a, 112b), a substance having a hole mobility of 10 ⁻⁶ cm ² / Vs or more is used. preferable. Note that a substance other than these substances can be used as long as the substance has a property of transporting more holes than electrons.

As the hole transporting material, a π-electron rich heteroaromatic compound (for example, a carbazole derivative or an indole derivative) or an aromatic amine compound is preferable, and specific examples thereof are 4,4′-bis [N- (1-naphthyl). ) -N-phenylamino] biphenyl (abbreviation: NPB or α-NPD), N, N′-bis (3-methylphenyl) -N, N′-diphenyl- [1,1′-biphenyl] -4,4 '-Diamine (abbreviation: TPD), 4,4'-bis [N- (spiro-9,9'-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB), 4-phenyl-4 '-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: mBPAFLP) ), 4-phenyl-4 '-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBAlBP), 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H -Carbazole (abbreviation: PCPPn),
N- (4-biphenyl) -N- (9,9-dimethyl-9H-fluoren-2-yl) -9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N- (1,1 ′ -Biphenyl-4-yl) -N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) 4,4 '-Diphenyl-4''-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBBi1BP), 4- (1-naphthyl) -4'-(9-phenyl-9H-carbazole- 3-yl) triphenylamine (abbreviation: PCBANB), 4,4′-di (1-naphthyl) -4 ″-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBN) B), 9,9-dimethyl-N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] spiro-9,9′-bifluoren-2-amine (abbreviation: PCBASF), 4,4 ′, 4 ″ -tris (carbazole-9 -Yl) triphenylamine (abbreviation: TCTA), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [ A compound having an aromatic amine skeleton such as N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA); 1,3-bis (N-carbazolyl) benzene (abbreviation: mC ), 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 3,6-bis (3,5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 3,3′-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP), 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-phenylcarbazole) -3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene ( Compounds having a carbazole skeleton, such as 9- [4- (10-phenyl-9-anthracenyl) phenyl] -9H-carbazole (abbreviation: CzPA), 4,4 ′, 4 ″-(benzene- 1,3,5-triyl) tri (dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] dibenzothiophene ( A compound having a thiophene skeleton such as DBTFLP-III), 4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] -6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 4 ′, 4 ″-(benzene-1,3,5-triyl) tri (dibenzofuran) (abbreviation: DBF3P-II), 4- {3- [3- (9 Phenyl -9H- fluoren-9-yl) phenyl] phenyl} dibenzofuran (abbreviation: mmDBFFLBi-II) compound having a furan skeleton such like.

Furthermore, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N '-[4- (4-diphenylamino)] Phenyl] phenyl-N'-phenylaminodiphenyl) methacrylamide] (abbreviation: PTPDMA) poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviation: Poly -TPD) can also be used.

However, the hole transporting material is not limited to the above, and one or a plurality of known various materials may be used as the hole transporting material by combining one or more kinds of materials, and the hole injecting layers (111, 111a, 111b) and the hole transporting layer may be used. (112, 112a, 112b). Note that each of the hole transport layers (112, 112a, 112b) may be formed of a plurality of layers. That is, for example, a first hole transport layer and a second hole transport layer may be stacked.

In the light-emitting element illustrated in FIG. 1D, a light-emitting layer 113a is formed over a hole-transport layer 112a of an EL layer 103a by a vacuum evaporation method. After the EL layer 103a and the charge generation layer 104 are formed, a light-emitting layer 113b is formed over the hole transport layer 112b of the EL layer 103b by a vacuum evaporation method.

<Light-emitting layer>
The light emitting layers (113, 113a, 113b, 113c) are layers containing a light emitting substance. Note that as the light-emitting substance, a substance which emits light of a color such as blue, purple, blue-violet, green, yellow-green, yellow, orange, or red is used as appropriate. In addition, by using different light-emitting substances for the plurality of light-emitting layers (113a, 113b, 113c), a structure in which different light-emitting colors are exhibited (for example, white light emission obtained by combining light-emitting colors having complementary colors) can be obtained. . Further, one light-emitting layer may have a stacked structure including different light-emitting substances.

Further, the light-emitting layer (113, 113a, 113b, 113c) may include one or more kinds of organic compounds (host material, assist material) in addition to the light-emitting substance (guest material). As the one or more kinds of organic compounds, one or both of a hole-transport material and an electron-transport material described in this embodiment can be used.

As a light-emitting substance that can be used for the light-emitting layers (113, 113a, 113b, and 113c), a light-emitting substance that changes singlet excitation energy to light in a visible light region or light emission that changes triplet excitation energy to light in a visible light region is used. Substances can be used.

In addition, as another light emitting substance, for example, the following substances can be mentioned.

Examples of the light-emitting substance that changes singlet excitation energy into light emission include a substance that emits fluorescence (fluorescent material). For example, pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, and dibenzofuran derivatives Quinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives and the like. In particular, a pyrene derivative is preferable because of its high emission 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 (1,6 mMemFLPAPrn), (N, N'-diphenyl-N, N'-bis [4- (9-phenyl-9H-fluoren-9-yl) phenyl] pyrene-1,6-diamine) (1 , 6FLPAPrn), N, N′-bis (dibenzofuran-2-yl) -N, N′-diphenylpyrene-1,6-diamine (1,6FrAPrn), N, N′-bis (dibenzothiophen-2-yl) ) -N, N'-diphenylpyrene-1,6-diamine (1,6ThAPrn), N, N '-(pyrene-1,6-diyl) bis [(N-phenylbenzo [b] naphtho [1,2 -D] (Ran) -6-amine] (abbreviation: 1,6BnfAPrn), N, N '-(pyrene-1,6-diyl) bis [(N-phenylbenzo [b] naphtho [1,2-d] furan)- 8-amine] (abbreviation: 1,6BnfAPrn-02), N, N ′-(pyrene-1,6-diyl) bis [(6, N-diphenylbenzo [b] naphtho [1,2-d] furan) -8-amine] (abbreviation: 1,6BnfAPrn-03).

In addition, 5,6-bis [4- (10-phenyl-9-anthryl) phenyl] -2,2′-bipyridine (abbreviation: PAP2BPy), 5,6-bis [4 ′-(10-phenyl- 9-anthryl) biphenyl-4-yl] -2,2'-bipyridine (abbreviation: PAPP2BPy), N, N'-bis [4- (9H-carbazol-9-yl) phenyl] -N, N'-diphenyl Stilbene-4,4'-diamine (abbreviation: YGA2S), 4- (9H-carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- ( 9H-carbazol-9-yl) -4 ′-(9,10-diphenyl-2-anthryl) triphenylamine (abbreviation: 2YGAPPA), N, 9-diphenyl-N- [4- (10 Phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: PCAPA), 4- (10-phenyl-9-anthryl) -4 ′-(9-phenyl-9H-carbazol-3-yl) Triphenylamine (abbreviation: PCBAPA), 4- [4- (10-phenyl-9-anthryl) phenyl] -4 '-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBAPBA) , Perylene, 2,5,8,11-tetra (tert-butyl) perylene (abbreviation: TBP), N, N ″-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene) Bis [N, N ′, N′-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N, 9-diphenyl-N- [4- ( , 10-Diphenyl-2-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: 2PCAPPA), N- [4- (9,10-diphenyl-2-anthryl) phenyl] -N, N ', N '-Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) or the like can be used.

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

Examples of the phosphorescent material include an organic metal complex, a metal complex (platinum complex), and a rare earth metal complex. Since these exhibit different emission colors (emission peaks) for each substance, they are appropriately selected and used as needed.

Examples of the phosphorescent material which emits blue or green light and has a peak wavelength of an emission spectrum of 450 nm or more and 570 nm or less include the following substances.

For example, tris {2- [5- (2-methylphenyl) -4- (2,6-dimethylphenyl) -4H-1,2,4-triazol-3-yl-κN2] phenyl-κC} iridium (III ) (Abbreviation: [Ir (mppptz-dmp) ₃ ]), tris (5-methyl-3,4-diphenyl-4H-1,2,4-triazolate) iridium (III) (abbreviation: [Ir (Mptz) _3] ]), Tris [4- (3-biphenyl) -5-isopropyl-3-phenyl-4H-1,2,4-triazolate] iridium (III) (abbreviation: [Ir (iPrptz-3b) ₃ ]) tris [ 3- (5-biphenyl) -5-isopropyl-4-phenyl-4H-1,2,4-triazolato] iridium (III) _{(abbreviation: Ir (iPr5btz) 3])} , 4 such as Organometallic complex having a triazole skeleton, tris [3-methyl-1- (2-methylphenyl) -5-phenyl-1H-1,2,4-triazolate] iridium (III) (abbreviation: [Ir (Mptz1- mp) ₃ ]) and tris (1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato) iridium (III) (abbreviation: [Ir (Prptz1-Me) ₃ ]). Organometallic complex having 1H-triazole skeleton, fac-tris [(2,6-diisopropylphenyl) -2-phenyl-1H-imidazole] iridium (III) (abbreviation: [Ir (iPrpmi) ₃ ]), tris [3 -(2,6-dimethylphenyl) -7-methylimidazo [1,2-f] phenanthridinato] iridium (III) (abbreviation: [I _(Dmpimpt-Me) 3] an organometallic complex having an imidazole skeleton, such as), bis [2- (4 ', 6'-difluorophenyl) pyridinato -N, C ^2'] iridium (III) tetrakis (1-pyrazolyl ) Borate (abbreviation: FIr6), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C ^{2 ′} ] iridium (III) picolinate (abbreviation: FIrpic), bis {2- [3 ′, 5 '- bis (trifluoromethyl) phenyl] pyridinato -N, C ^2'] iridium (III) picolinate _{(abbreviation: [Ir (CF 3 ppy)} 2 (pic)]), bis [2- (4 ', 6' - difluorophenyl) pyridinato -N, C ^{2 ']} iridium (III) acetylacetonate (abbreviation: FIr (acac) off with an electron withdrawing group such as) The Nirupirijin derivatives and organic metal complexes having a ligand.

Examples of the phosphorescent material which emits green or yellow light and has a peak wavelength of an emission spectrum of 495 nm or more and 590 nm or less include the following substances.

For example, tris (4-methyl-6-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) ₃ ]), tris (4-t-butyl-6-phenylpyrimidinato) iridium (III) (Abbreviation: [Ir (tBuppm) ₃ ]), (acetylacetonato) bis (6-methyl-4-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) ₂ (acac)]), ( Acetylacetonato) bis (6-tert-butyl-4-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (tBuppm) ₂ (acac)]), (acetylacetonato) bis [6- (2- Norbornyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (nbppm) ₂ (acac)]), (acetylacetona G) bis [5-methyl-6- (2-methylphenyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (mpmppm) ₂ (acac)]), (acetylacetonato) bis 4,6-dimethyl-2- [6- (2,6-dimethylphenyl) -4-pyrimidinyl-κN3] phenyl-κC｝ iridium (III) (abbreviation: [Ir (dmppm-dmp) ₂ (acac)]) An organometallic iridium complex having a pyrimidine skeleton such as, (acetylacetonato) bis (4,6-diphenylpyrimidinato) iridium (III) (abbreviation: [Ir (dppm) ₂ (acac)]), isocyanatomethyl) 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) pyrazine skeleton, such as 2 (acac)]) Organometallic iridium complex having the formula: tris (2-phenylpyridinato-N, C2 ^' ) iridium (III) (abbreviation: [Ir (ppy) ₃ ]], bis (2-phenylpyridinato-N, C ^{2 ′} ) Iridium (III) acetylacetonate (abbreviation: [Ir (ppy) ₂ (acac)]), bis (benzo [h] quinolinato) iridium (III) acetylacetonate (abbreviation: [Ir (bzq) ₂ ( acac)]), tris (benzo [h] quinolinato) iridium (III) _{(abbreviation: [Ir (bzq) 3]} ), tris (2-Fenirukinori DOO -N, C ^{2 ')} iridium (III) _{(abbreviation: [Ir (pq) 3]} ), bis (2-phenylquinolinato--N, C ^2') iridium (III) acetylacetonate (abbreviation: [Ir (Pq) ₂ (acac)]), an organometallic iridium complex having a pyridine skeleton, bis (2,4-diphenyl-1,3-oxazolate-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-phenyl-benzothiazyl Zola DOO -N, C ^{2 ')} iridium (III) acetylacetonate (abbreviation: [Ir (bt ₂ (acac)]) other organometallic complexes such as tris (acetylacetonato) (monophenanthroline) terbium (III) _{(abbreviation: [Tb (acac) 3 (} Phen)]) include rare earth metal complex such as Can be

Examples of the phosphorescent material which emits yellow or red light and has a peak wavelength of an emission spectrum of 570 nm to 750 nm include the following substances.

For example, (diisobutyrylmethanato) bis [4,6-bis (3-methylphenyl) pyrimidinato] iridium (III) (abbreviation: [Ir (5 mdppm) ₂ (dibm)]), bis [4,6-bis ( 3-Methylphenyl) pyrimidinato] (dipivaloylmethanato) iridium (III) (abbreviation: [Ir (5 mdppm) ₂ (dpm)]), (dipivaloylmethanato) bis [4,6-di (naphthalene- Organometallic complexes having a pyrimidine skeleton such as 1-yl) pyrimidinato] iridium (III) (abbreviation: [Ir (d1npm) ₂ (dpm)]), (acetylacetonato) bis (2,3,5-triphenyl) Pirajinato) 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 ² O, O ′) iridium (III) (abbreviation: [Ir (dmdppr-P) ₂ (dibm) ]), Bis {4,6-dimethyl-2- [5- (4-cyano-2,6-dimethylphenyl) -3- (3,5-dimethylphenyl) -2-pyrazinyl-κN] phenyl-κC} (2,2,6,6-tetramethyl-3,5-heptanedionato-κ ² O, O ′) iridium (III) (abbreviation: [Ir (dmdppr-dmCP) ₂ (dpm)]), (acetylacetonato ) Screw [2 -Methyl-3-phenylquinoxalinato-N, C ^{2 ′} ] iridium (III) (abbreviation: [Ir (mpq) ₂ (acac)]), (acetylacetonato) bis (2,3-diphenylquinoxalinato —N, C ^{2 ′} ) iridium (III) (abbreviation: [Ir (dpq) ₂ (acac)]), (acetylacetonato) bis [2,3-bis (4-fluorophenyl) quinoxalinato] iridium (III) (Abbreviation: [Ir (Fdpq) ₂ (acac)]), an organometallic complex having a pyrazine skeleton, and tris (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) (abbreviation: [Ir (Piq) ₃ ]), bis (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) acetylacetonate (abbreviation: [Ir (piq) ₂ (aca) c)], an organometallic complex having a pyridine skeleton such as 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation: [PtOEP]) Such a platinum complex, 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)]).

As the organic compound (host material, assist material) used for the light emitting layer (113, 113a, 113b, 113c), one or more substances having an energy gap larger than the energy gap of the light emitting substance (guest material) are selected. It may be used.

When the light-emitting substance is a fluorescent material, it is preferable to use an organic compound having a large energy level in a singlet excited state and a small energy level in a triplet excited state as a host material. For example, it is preferable to use an anthracene derivative or a tetracene derivative. Specifically, 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA), 3- [4- (1-naphthyl) -phenyl] -9 -Phenyl-9H-carbazole (abbreviation: PCPN), 9- [4- (10-phenyl-9-anthracenyl) phenyl] -9H-carbazole (abbreviation: CzPA), 7- [4- (10-phenyl-9- (Anthryl) phenyl] -7H-dibenzo [c, g] carbazole (abbreviation: cgDBCzPA), 6- [3- (9,10-diphenyl-2-anthryl) phenyl] -benzo [b] naphtho [1,2-d ] Furan (abbreviation: 2mBnfPPA), 9-phenyl-10- {4- (9-phenyl-9H-fluoren-9-yl) -biphenyl-4'-yl} anthracene (Abbreviation: FLPPA), 5,12 diphenyltetracene, 5,12-bis (biphenyl-2-yl) tetracene, and the like.

In the case where the light-emitting substance is a phosphorescent material, an organic compound having a higher triplet excitation energy than a triplet excitation energy (an energy difference between a ground state and a triplet excited state) of the light-emitting substance may be selected as the host material. In this case, in addition to zinc and aluminum-based metal complexes, oxadiazole derivatives, triazole derivatives, benzimidanol derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, pyrimidine derivatives, triazine derivatives, In addition to pyridine derivatives, bipyridine derivatives, phenanthroline derivatives, and the like, aromatic amines, carbazole derivatives, and the like can be used.

More specifically, for example, the following hole transporting materials and electron transporting materials can be used as the host material.

Examples of these host materials having a high hole transporting property include N, N′-di (p-tolyl) -N, N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA) and 4,4′-bis [ N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), N, N'-bis {4- [bis (3-methylphenyl) amino] phenyl} -N, N'-diphenyl -(1,1'-biphenyl) -4,4'-diamine (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B) And the like.

Further, 3- [N- (4-diphenylaminophenyl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] -9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis [N- (4-diphenylaminophenyl) -N- (1-naphthyl) amino] -9-phenylcarbazole (abbreviation: PCzTPN2), 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 Phenyl-3-yl) amino] phenyl carbazole (abbreviation: PCzPCNl) can be mentioned carbazole derivatives such. Other examples of the carbazole derivative include 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP) and 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene (abbreviation: TCPB) ), 1,4-bis [4- (N-carbazolyl) phenyl] -2,3,5,6-tetraphenylbenzene and the like can also be used.

Examples of a host material having a high hole-transport property include 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB or α-NPD) and N, N ′ -Bis (3-methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (abbreviation: TPD), 4,4 ', 4' '-tris (carbazole- 9-yl) triphenylamine (abbreviation: TCTA), 4,4 ′, 4 ″ -tris [N- (1-naphthyl) -N-phenylamino] triphenylamine (abbreviation: 1′-TNATA), 4 , 4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino ] Triphenylamine (abbreviation) m-MTDATA), 4,4'-bis [N- (spiro-9,9'-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB), 4-phenyl-4 '-(9 -Phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP), 4-phenyl-3 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: mBPAFLP), N- (9,9f- Dimethyl-9H-fluoren-2-yl) -N- {9,9-dimethyl-2- [N'-phenyl-N '-(9,9-dimethyl-9H-fluoren-2-yl) amino] -9H -Fluoren-7-yl} phenylamine (abbreviation: DFLADFL), N- (9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl) diphenylamine (abbreviation: DPNF), 2- [N- (4-diphenylaminophenyl) -N-phenylamino] spiro-9,9'-bifluorene (abbreviation: DPASF), 4-phenyl-4 '-(9-phenyl-9H-carbazole -3-yl) triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4 "-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBBi1BP), 4- ( 1-naphthyl) -4 ′-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBANB), 4,4′-di (1-naphthyl) -4 ″-(9-phenyl) -9H-carbazol-3-yl) triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl- (9-phenyl-9H-carbazol-3-) L) 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), N- (4-biphenyl)- N- (9,9-dimethyl-9H-fluoren-2-yl) -9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N- (1,1′-biphenyl-4-yl)- N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 9,9-dimethyl-N-phenyl- N- [ -(9-phenyl-9H-carbazol-3-yl) phenyl] fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl Spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 2- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] spiro-9,9'-bifluorene (abbreviation) : PCASF), 2,7-bis [N- (4-diphenylaminophenyl) -N-phenylamino] -spiro-9,9'-bifluorene (abbreviation: DPA2SF), N- [4- (9H-carbazole- 9-yl) phenyl] -N- (4-phenyl) phenylaniline (abbreviation: YGA1BP), N, N′-bis [4- (carbazol-9-yl) phenyl Aromatic amine compounds such as -N, N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F) can be used. Further, 3- [4- (1-naphthyl) -phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPN), 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H-carbazole (Abbreviation: PCPPn), 3,3'-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP), 1,3-bis (N-carbazolyl) benzene (abbreviation: mCP), 3,6-bis ( 3,5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 4- {3- [3- (9-phenyl-9H-fluoren-9-yl) phenyl] phenyl} dibenzofuran (abbreviation: mmDBFFLBi-II) ), 4,4 ′, 4 ″-(benzene-1,3,5-triyl) tri (dibenzofuran) (abbreviation: DBF3P-II), 1,3,5-tri (dibenzofuran) (Nzothiophen-4-yl) -benzene (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] dibenzothiophene (abbreviation: DBTFLP-III) ), 4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] -6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 4- [3- (triphenylen-2-yl) phenyl] A carbazole compound such as dibenzothiophene (abbreviation: mDBTPTp-II), a thiophene compound, a furan compound, a fluorene compound, a triphenylene compound, a phenanthrene compound, or the like can be used.

Examples of the host material having a high electron-transport property include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis ( Metal complexes having a quinoline skeleton or a benzoquinoline skeleton, such as 8-quinolinolato) zinc (II) (abbreviation: Znq). In addition, bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), etc. Metal complexes having an oxazole-based or thiazole-based ligand can also be used. Further, in addition to the metal complex, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD) and 1,3-bis [5 -(P-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 9- [4- (5-phenyl-1,3,4-oxa Oxadiazole derivatives such as diazol-2-yl) phenyl] -9H-carbazole (abbreviation: CO11) and 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl)- Triazole derivatives such as 1,2,4-triazole (abbreviation: TAZ) and 2,2 ′, 2 ″-(1,3,5-benzenetriyl) tris (1-phenyl-1H-benzimidazole) (Abbreviation: TPBI A compound having an imidazole skeleton (particularly, a benzimidazole derivative) such as 2- [3- (dibenzothiophen-4-yl) phenyl] -1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II); Compounds having an oxazole skeleton (especially benzoxazole derivatives) such as 4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: BzOS), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP) Phenanthroline derivatives such as 2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen) and 2- [3- (dibenzothiophen-4-yl) phenyl ] Dibenzo [f, h] quinoxaline (abbreviation: 2mDB PDBq-II), 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq-II), 2- [3 ′-(9H-carbazole -9-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mCzBPDBq), 2- [4- (3,6-diphenyl-9H-carbazol-9-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 2CzPDBq-III), 7- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 7mDBTPDBq-II), and 6- [3- (dibenzothiophene) -4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 6mDBTPDBq-II), 4,6-bis [ 3- (phenanthren-9-yl) phenyl] pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis [3- (4-dibenzothienyl) phenyl] pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6 Heterocyclic compounds having a diazine skeleton, such as -bis [3- (9H-carbazol-9-yl) phenyl] pyrimidine (abbreviation: 4,6mCzP2Pm), and 2- {4- [3- (N-phenyl-9H- Heterocyclic compounds having a triazine skeleton such as carbazol-3-yl) -9H-carbazol-9-yl] phenyl} -4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn); -Bis [3- (9H-carbazol-9-yl) phenyl] pyridine (abbreviation: 35DCzPPy), 1,3,5-tri [3- ( - pyridyl) phenyl] benzene (abbreviation: TmPyPB) can also be used a heterocyclic compound having a pyridine skeleton such. Further, 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-BPy). Molecular compounds can also be used.

Examples of the host material include condensed polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo [g, p] chrysene derivatives. Specifically, 9,10-diphenylanthracene ( Abbreviation: DPAnth), N, N-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: CzA1PA), 4- (10-phenyl-9- Anthryl) triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N, 9-diphenyl-N- {4- [4- (10-phenyl-9-anthryl) phenyl] phenyl} -9H-carbazol-3-amine (Abbreviation: PCAPBA) 2PCAPA, 6,12-dimethoxy-5,11-diphenylc Sen, DBC1, 9- [4- (10-phenyl-9-anthracenyl) phenyl] -9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9- [4- (10-phenyl-9-anthryl) Phenyl] -9H-carbazole (abbreviation: DPCzPA), 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), or the like can be used.

When a plurality of organic compounds are used for the light-emitting layers (113, 113a, 113b, 113c), two kinds of compounds (a first compound and a second compound) that form an exciplex are mixed with an organometallic complex. May be used. In this case, various organic compounds can be appropriately used in combination. However, in order to form an exciplex efficiently, a compound that easily accepts holes (a hole transporting material) and a compound that easily accepts electrons (an electron (Transportable material). Note that as specific examples of the hole-transport material and the electron-transport material, the materials described in this embodiment can be used. With this configuration, high efficiency, low voltage, and long life can be simultaneously realized.

A TADF material is a material that can up-convert a triplet excited state to a singlet excited state with a small amount of thermal energy (crossover between inverse terms) and efficiently emits light (fluorescence) from the singlet excited state. is there. The condition under which the thermally activated delayed fluorescence can be efficiently obtained is that the energy difference between the triplet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. No. In addition, the term “delayed fluorescence” in a TADF material refers to light emission that has a spectrum similar to that of ordinary fluorescence but has an extremely long life. Its lifetime is at least 10 ^-6 seconds, preferably at least 10 ^-3 seconds.

Examples of the TADF material include fullerene and its derivatives, acridine derivatives such as proflavine, and eosin. Further, a metal-containing porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), or the like can be given. Examples of the metal-containing porphyrin include a protoporphyrin-tin fluoride complex (abbreviation: SnF ₂ (Proto IX)), a mesoporphyrin-tin fluoride complex (abbreviation: SnF ₂ (Meso IX)), and hematoporphyrin-tin fluoride. Complex (abbreviation: SnF ₂ (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF ₂ (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF ₂ (OEP) )), Ethioporphyrin-tin fluoride complex (abbreviation: SnF ₂ (Etio I)), octaethylporphyrin-platinum chloride complex (abbreviation: PtCl ₂ OEP), and the like.

In addition, 2- (biphenyl-4-yl) -4,6-bis (12-phenylindolo [2,3-a] carbazol-11-yl) -1,3,5-triazine (abbreviation: PIC) -TRZ), 2- {4- [3- (N-phenyl-9H-carbazol-3-yl) -9H-carbazol-9-yl] phenyl} -4,6-diphenyl-1,3,5-triazine (Abbreviation: 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) -Acridine- 0-yl) -9H-xanthen-9-one (abbreviation: ACRXTN), bis [4- (9,9-dimethyl-9,10-dihydroacridine) phenyl] sulfone (abbreviation: DMAC-DPS), 10-phenyl A heterocyclic ring having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring such as -10H, 10'H-spiro [acridine-9,9'-anthracene] -10'-one (abbreviation: ACRSA); Compounds can be used. Note that a substance in which a π-electron rich heteroaromatic ring is directly bonded to a π-electron deficient heteroaromatic ring has both a donor property of the π-electron-rich heteroaromatic ring and an acceptor property of the π-electron-deficient heteroaromatic ring. This is particularly preferable because the energy difference between the singlet excited state and the triplet excited state is reduced.

When a TADF material is used, it can be used in combination with another organic compound.

In the light-emitting element illustrated in FIG. 1D, an electron-transport layer 114a is formed over the light-emitting layer 113a of the EL layer 103a by a vacuum evaporation method. After the EL layer 103a and the charge generation layer 104 are formed, an electron transport layer 114b is formed over the light-emitting layer 113b of the EL layer 103b by a vacuum evaporation method.

<Electron transport layer>
The electron transport layers (114, 114a, 114b) are layers that transport electrons injected from the second electrode 102 to the light emitting layers (113, 113a, 113b) by the electron injection layers (115, 115a, 115b). . Note that the electron transporting layers (114, 114a, 114b) are layers containing an electron transporting material. The electron transporting material used for the electron transporting layers (114, 114a, 114b) is preferably a substance having an electron mobility of 1 × 10 ⁻⁶ cm ² / Vs or more. Note that a substance other than these substances can be used as long as the substance has a property of transporting more electrons than holes.

Examples of the electron transporting material include metal complexes having a quinoline ligand, a benzoquinoline ligand, an oxazole ligand, or a thiazole ligand, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, a pyridine derivative, and a bipyridine derivative. Is mentioned. In addition, a π electron deficient heteroaromatic compound such as a nitrogen-containing heteroaromatic compound can be used.

Specifically, Alq ₃ , tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq ₂ ) , BAlq, bis [2- (2-hydroxyphenyl) benzoxazolat] zinc (II) (abbreviation: Zn (BOX) ₂ ), bis [2- (2-hydroxyphenyl) benzothiazolat] zinc (II) (abbreviation) : Metal complex such as Zn (BTZ) ₂ ), 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), OXD-7, 3- (4′-tert-butylphenyl) -4-phenyl-5- (4 ″ -biphenyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-te rt-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), heteroaromatic compounds such as 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: BzOS), 2- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [ f, h] quinoxaline (abbreviation: 2mDBTPDBq-II), 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTPBPDBq-II), 2- [4- (3,6-diphenyl-9H-carbazol-9-yl) phenyl] dibenzo [f, h] quinoxaline ( Name: 2CzPDBq-III), 7- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 7mDBTPDBq-II), 6- [3- (dibenzothiophen-4-yl) A quinoxaline or a dibenzoquinoxaline derivative such as phenyl] dibenzo [f, h] quinoxaline (abbreviation: 6mDBTPDBq-II) can be used.

Further, 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-BPy). Molecular compounds can also be used.

Further, the electron transport layer (114, 114a, 114b) is not limited to a single layer, and may have a structure in which two or more layers made of the above substances are stacked.

In the light-emitting element illustrated in FIG. 1D, an electron-injection layer 115a is formed over the electron-transport layer 114a of the EL layer 103a by a vacuum evaporation method. After that, the EL layer 103a and the charge generation layer 104 are formed, and after the electron transport layer 114b of the EL layer 103b is formed, the electron injection layer 115b is formed thereon by a vacuum evaporation method.

<Electron injection layer>
The electron injection layers (115, 115a, 115b) are layers containing a substance having a high electron injection property. An alkali metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiO _x ), or an alkali is used for the electron injection layers (115, 115a, 115b). Earth metals or their compounds can be used. In addition, a rare earth metal compound such as erbium fluoride (ErF ₃ ) can be used. In addition, electride may be used for the electron injection layer (115, 115a, 115b). Examples of the electride include a substance obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum. Note that a substance included in the above-described electron transport layer (114, 114a, 114b) can be used.

Further, a composite material in which an organic compound and an electron donor (donor) are mixed may be used for the electron injection layers (115, 115a, 115b). Such a composite material is excellent in an electron injecting property and an electron transporting property because electrons are generated in an organic compound by an electron donor. In this case, the organic compound is preferably a material excellent in transporting generated electrons. Specifically, for example, the electron transporting material (metal complex) used for the above-described electron transporting layer (114, 114a, 114b) Or a heteroaromatic compound). The electron donor may be any substance that has an electron donating property to an organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Further, an alkali metal oxide or an alkaline earth metal oxide is preferable, and examples thereof include lithium oxide, calcium oxide, and barium oxide. Also, a Lewis base such as magnesium oxide can be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

Note that, for example, in the case where light obtained from the light-emitting layer 113b is amplified, the optical distance between the second electrode 102 and the light-emitting layer 113b is smaller than λ / 4 with respect to the wavelength of the light exhibited by the light-emitting layer 113b. It is preferable to form so that it becomes. In this case, adjustment can be performed by changing the thickness of the electron transport layer 114b or the electron injection layer 115b.

<Charge generation layer>
When a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102, the charge generation layer 104 injects electrons into the EL layer 103a and creates holes in the EL layer 103b. Has the ability to inject. Note that the charge generation layer 104 may have a structure in which an electron acceptor (acceptor) is added to a hole transporting material or a structure in which an electron donor (donor) is added to an electron transporting material. Good. Alternatively, both of these configurations may be stacked. Note that when the charge generation layer 104 is formed using the above-described materials, an increase in driving voltage in a case where EL layers are stacked can be suppressed.

In the case where the charge generation layer 104 has a structure in which an electron acceptor is added to a hole-transport material, the material described in this embodiment can be used as the hole-transport material. Examples of the electron acceptor include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F ₄ -TCNQ) and chloranil. In addition, oxides of metals belonging to Groups 4 to 8 of the periodic table can be given. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, and the like can be given.

In the case where the charge generation layer 104 has a structure in which an electron donor is added to an electron-transporting material, the material described in this embodiment can be used as the electron-transporting material. In addition, as the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, a metal belonging to Group 2 or 13 of the periodic table, and an oxide or carbonate thereof can be used. Specifically, it is preferable to use lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, or the like. Further, an organic compound such as tetrathianaphthacene may be used as the electron donor.

Note that the EL layer 103c in FIG. 1E may have a structure similar to that of the above-described EL layers (103, 103a, and 103b). In addition, the charge generation layers 104a and 104b may have the same configuration as the charge generation layer 104 described above.

<Substrate>
The light-emitting element described in this embodiment can be formed over a variety of substrates. The type of the substrate is not limited to a specific one. Examples of the substrate include a semiconductor substrate (eg, a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate having a stainless steel foil, a tungsten substrate, Examples include a substrate having a tungsten foil, a flexible substrate, a laminated film, paper containing a fibrous material, or a base film.

Note that examples of a material of the glass substrate include barium borosilicate glass, aluminoborosilicate glass, and soda lime glass. Examples of a flexible substrate, a laminated film, a base film, and the like include plastics such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES), and synthetic acrylic. Examples include resin, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride, polyamide, polyimide, aramid, epoxy, an inorganic vapor-deposited film, and papers.

Note that a light-emitting element described in this embodiment can be manufactured by a vacuum process such as an evaporation method or a solution process such as a spin coating method or an inkjet method. When an evaporation method is used, a physical evaporation method (PVD method) such as a sputtering method, an ion plating method, an ion beam evaporation method, a molecular beam evaporation method, or a vacuum evaporation method, or a chemical evaporation method (CVD method) is used. be able to. In particular, the functional layers (the hole injection layers (111, 111a, 111b), the hole transport layers (112, 112a, 112b), the light emitting layers (113, 113a, 113b, 113c) included in the EL layer of the light emitting element, and the electron transport For the layers (114, 114a, 114b), the electron injection layers (115, 115a, 115b), and the charge generation layers (104, 104a, 104b), an evaporation method (such as a vacuum evaporation method) and a coating method (a dip coating method) , Die coating method, bar coating method, spin coating method, spray coating method, etc.), printing method (ink jet method, screen (stencil printing) method, offset (lithographic printing) method, flexo (letter printing) method, gravure method, micro contact Method, etc.).

Note that each functional layer (a hole injection layer (111, 111a, 111b), a hole transport layer (112, 112a, 112b)) included in the EL layer (103, 103a, 103b) of the light-emitting element described in this embodiment mode. The light emitting layers (113, 113a, 113b, 113c), the electron transport layers (114, 114a, 114b), the electron injection layers (115, 115a, 115b), and the charge generation layers (104, 104a, 104b) are described above. The material is not limited to the material, and other materials can be used in combination as long as they can satisfy the function of each layer. As an example, a high molecular compound (oligomer, dendrimer, polymer, etc.), a medium molecular compound (compound in an intermediate region between a low molecular weight and a high molecular weight: molecular weight of 400 to 4000), an inorganic compound (quantum dot material, etc.) and the like can be used. it can. As the quantum dot material, a colloidal quantum dot material, an alloy type quantum dot material, a core-shell type quantum dot material, a core type quantum dot material, or the like can be used.

The structure described in this embodiment can be used in appropriate combination with the structure described in any of the other embodiments.

(Embodiment 3)
In this embodiment, a light-emitting device which is one embodiment of the present invention will be described. Note that the light-emitting device illustrated in FIG. 2A is an active matrix light-emitting device in which a transistor (FET) 202 and a light-emitting element (203R, 203G, 203B, and 203W) over a first substrate 201 are electrically connected. A plurality of light-emitting elements (203R, 203G, 203B, 203W) have a common EL layer 204, and the optical distance between the electrodes of each light-emitting element depends on the emission color of each light-emitting element. It has a tuned microcavity structure. Further, this is a top emission light-emitting device in which light emitted from the EL layer 204 is emitted through color filters (206R, 206G, 206B) formed in the second substrate 205.

In the light-emitting device illustrated in FIG. 2A, the first electrode 207 is formed so as to function as a reflective electrode. Further, the second electrode 208 is formed so as to function as a semi-transmissive / semi-reflective electrode. Note that an electrode material for forming the first electrode 207 and the second electrode 208 may be used as appropriate with reference to the description of other embodiments.

2A. For example, in FIG. 2A, when the light-emitting element 203R is a red light-emitting element, the light-emitting element 203G is a green light-emitting element, the light-emitting element 203B is a blue light-emitting element, and the light-emitting element 203W is a white light-emitting element. ), The light emitting element 203R is adjusted so that the optical distance between the first electrode 207 and the second electrode 208 is 200R, and the light emitting element 203G is adjusted to the first electrode 207 and the second electrode 207. The distance between the first electrode 207 and the second electrode 208 is adjusted so that the distance between the first electrode 207 and the second electrode 208 is adjusted to 200 G. Note that as shown in FIG. 2B, in the light-emitting element 203R, the conductive layer 207R is stacked over the first electrode 207, and in the light-emitting element 203G, the conductive layer 207G is stacked on the first electrode 207, so that optical adjustment is performed. It can be performed.

Color filters (206R, 206G, 206B) are formed on the second substrate 205. The color filter is a filter that allows a specific wavelength range of visible light to pass therethrough and blocks a specific wavelength range. Therefore, as shown in FIG. 2A, by providing a color filter 206R that passes only the red wavelength band at a position overlapping with the light emitting element 203R, red light emission can be obtained from the light emitting element 203R. In addition, by providing a color filter 206G that passes only the green wavelength band at a position overlapping with the light emitting element 203G, green light can be emitted from the light emitting element 203G. Further, by providing a color filter 206B that passes only the blue wavelength band at a position overlapping with the light emitting element 203B, blue light emission can be obtained from the light emitting element 203B. However, the light-emitting element 203W can obtain white light emission without providing a color filter. Note that a black layer (black matrix) 209 may be provided at an end of one type of color filter. Further, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer using a transparent material.

FIG. 2A shows a light-emitting device having a structure (top emission type) in which light is emitted to the second substrate 205 side, but the first substrate on which the FET 202 is formed as shown in FIG. A light emitting device having a structure (bottom emission type) for extracting light to the side 201 may be used. Note that in the case of a bottom-emission light-emitting device, the first electrode 207 is formed to function as a semi-transmissive / semi-reflective electrode, and the second electrode 208 is formed to function as a reflective electrode. For the first substrate 201, at least a light-transmitting substrate is used. The color filters (206R ', 206G', 206B ') may be provided on the first substrate 201 side of the light-emitting elements (203R, 203G, 203B) as shown in FIG.

FIG. 2A illustrates the case where the light-emitting elements are a red light-emitting element, a green light-emitting element, a blue light-emitting element, and a white light-emitting element; however, a light-emitting element of one embodiment of the present invention is limited to that structure. Instead, a structure having a yellow light emitting element or an orange light emitting element may be employed. Note that as a material used for an EL layer (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) for manufacturing these light-emitting elements, another embodiment is used. May be used as appropriate, with reference to the description. In this case, it is necessary to appropriately select a color filter according to the emission color of the light emitting element.

With the above structure, a light-emitting device including a light-emitting element that emits light of a plurality of colors can be obtained.

Note that the structure described in this embodiment can be used in appropriate combination with any of the structures described in the other embodiments.

(Embodiment 4)
In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

By applying the element structure of the light-emitting element which is one embodiment of the present invention, an active matrix light-emitting device and a passive matrix light-emitting device can be manufactured. Note that an active matrix light-emitting device has a structure in which a light-emitting element and a transistor (FET) are combined. Therefore, a passive-matrix light-emitting device and an active-matrix light-emitting device are both embodiments of the present invention. Note that the light-emitting element described in another embodiment can be applied to the light-emitting device described in this embodiment.

In this embodiment, an active matrix light-emitting device will be described with reference to FIGS.

Note that FIG. 3A is a top view illustrating the light-emitting device, and FIG. 3B is a cross-sectional view of FIG. 3A taken along a chain line A-A ′. The active matrix light-emitting device includes a pixel portion 302 provided over a first substrate 301, a driver circuit portion (source line driver circuit) 303, and a driver circuit portion (gate line driver circuit) (304a, 304b). . The pixel portion 302 and the driver circuit portions 303, 304a, and 304b) are sealed between the first substrate 301 and the second substrate 306 by a sealant 305.

In addition, a lead wiring 307 is provided over the first substrate 301. The lead wiring 307 is connected to the FPC 308 which is an external input terminal. Note that the FPC 308 transmits a signal (for example, a video signal, a clock signal, a start signal, a reset signal, and the like) and a potential from the outside to the driving circuit units (303, 304a, and 304b). Further, a printed wiring board (PWB) may be attached to the FPC 308. The state in which the FPC or PWB is attached is included in the light emitting device.

Next, FIG. 3B shows a cross-sectional structure.

The pixel portion 302 is formed by a plurality of pixels each having an FET (switching FET) 311, an FET (current control FET) 312, and a first electrode 313 electrically connected to the FET 312. Note that the number of FETs included in each pixel is not particularly limited, and can be appropriately provided as needed.

The FETs 309, 310, 311, and 312 are not particularly limited, and for example, a staggered or inverted staggered transistor can be used. Further, a transistor structure of a top gate type, a bottom gate type, or the like may be employed.

Note that there is no particular limitation on the crystallinity of a semiconductor that can be used for the FETs 309, 310, 311, and 312, and an amorphous semiconductor, a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, Or a semiconductor partially having a crystal region). Note that using a semiconductor having crystallinity is preferable because deterioration of transistor characteristics can be suppressed.

In addition, as these semiconductors, for example, an element belonging to Group 14, a compound semiconductor, an oxide semiconductor, an organic semiconductor, or the like can be used. Typically, a semiconductor containing silicon, a semiconductor containing gallium arsenide, an oxide semiconductor containing indium, or the like can be used.

The drive circuit unit 303 includes an FET 309 and an FET 310. Note that the FET 309 and the FET 310 may be formed of a circuit including a unipolar (only one of N-type and P-type) transistors, or may be formed of a CMOS circuit including an N-type transistor and a P-type transistor. May be. Further, a structure having a driving circuit outside may be employed.

An end of the first electrode 313 is covered with an insulator 314. Note that for the insulator 314, an organic compound such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin), or an inorganic compound such as silicon oxide, silicon oxynitride, or silicon nitride can be used. . It is preferable that the insulator 314 have a curved surface with a curvature at the upper end or the lower end. This makes it possible to improve the coverage of the film formed over the insulating portion 314.

An EL layer 315 and a second electrode 316 are formed over the first electrode 313. 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.

Note that the structure and materials described in the other embodiments can be applied to the structure of the light-emitting element 317 described in this embodiment. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal.

Although only one light-emitting element 317 is illustrated in the cross-sectional view in FIG. 3B, it is assumed that a plurality of light-emitting elements are arranged in a matrix in the pixel portion 302. In the pixel portion 302, light-emitting elements that can emit light of three types (R, G, and B) are selectively formed, so that a light-emitting device capable of full-color display can be formed. Further, in addition to the light-emitting elements that can emit light of three types (R, G, and B), for example, light emission that can emit light of white (W), yellow (Y), magenta (M), and cyan (C) can be obtained. An element may be formed. For example, by adding a light emitting element capable of obtaining the above-mentioned several kinds of light emission to a light emitting element capable of obtaining three kinds of light emission (R, G, B), effects such as improvement of color purity and reduction of power consumption can be obtained. Can be. Further, a light emitting device capable of full color display may be formed by combining with a color filter. In addition, as a type of the color filter, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), and the like can be used.

The FETs (309, 310, 311 and 312) and the light-emitting element 317 on the first substrate 301 are formed by bonding the second substrate 306 and the first substrate 301 with the sealant 305. It has a structure provided in a space 318 surrounded by 301, a second substrate 306, and a sealant 305. Note that the space 318 may be filled with an inert gas (such as nitrogen or argon) or an organic substance (including the sealant 305).

For the sealant 305, an epoxy resin or glass frit can be used. Note that a material which does not transmit moisture or oxygen as much as possible is preferably used for the sealant 305. As the second substrate 306, a substrate that can be used for the first substrate 301 can be used in a similar manner. Therefore, the various substrates described in the other embodiments can be used as appropriate. In addition to a glass substrate or a quartz substrate, a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used as the substrate. When a glass frit is used as the sealant, the first substrate 301 and the second substrate 306 are preferably glass substrates from the viewpoint of adhesiveness.

As described above, an active matrix light-emitting device can be obtained.

In the case where an active matrix light-emitting device is formed over a flexible substrate, the FET and the light-emitting element may be directly formed over the flexible substrate. Then, the FET and the light-emitting element may be separated by a release layer by applying heat, force, laser irradiation, or the like, and then may be transferred to a flexible substrate for manufacturing. Note that as the release layer, for example, a stack of an inorganic film of a tungsten film and a silicon oxide film, an organic resin film such as polyimide, or the like can be used. As the flexible substrate, in addition to a substrate on which a transistor can be formed, a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a cloth substrate (natural fibers (silk, cotton, hemp), synthetic fibers ( Nylon, polyurethane, polyester) or recycled fiber (including acetate, cupra, rayon, recycled polyester), a leather substrate, a rubber substrate, and the like. By using these substrates, durability and heat resistance are excellent, and a reduction in weight and thickness can be achieved.

Note that the structure described in this embodiment can be combined with any of the structures described in the other embodiments as appropriate.

(Embodiment 5)
In this embodiment, examples of various electronic devices and automobiles which are completed using a light-emitting device of one embodiment of the present invention and a display device including a light-emitting element of one embodiment of the present invention will be described.

4A to 4E, a housing 7000, a display portion 7001, a speaker 7003, an LED lamp 7004, operation keys 7005 (including a power switch or an operation switch), a connection terminal 7006, Sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical, sound, time, hardness, electric field, current, voltage, power, radiation, flow, humidity Including a function of measuring inclination, vibration, odor, or infrared light), a microphone 7008, and the like.

FIG. 4A illustrates a mobile computer, which can include a switch 7009, an infrared port 7010, and the like in addition to the above objects.

FIG. 4B illustrates a portable image reproducing device (for example, a DVD reproducing device) including a recording medium, which may include a second display portion 7002, a recording medium reading portion 7011, and the like in addition to the above components. it can.

FIG. 4C illustrates a goggle-type display which can include a second display portion 7002, a support portion 7012, an earphone 7013, and the like in addition to the above components.

FIG. 4D illustrates a digital camera with a television receiving function, which can include an antenna 7014, a shutter button 7015, an image receiving portion 7016, and the like in addition to the above objects.

FIG. 4E illustrates a mobile phone (including a smartphone), which can include a display portion 7001, a microphone 7008, a speaker 7003, a camera 7020, an external connection portion 7021, operation buttons 7022, and the like in the housing 7000. .

FIG. 4F illustrates a large television device (also referred to as a television or a television receiver), which can include a housing 7000, a display portion 7001, a speaker 7003, and the like. Here, a structure in which the housing 7000 is supported by the stand 7018 is illustrated.

The electronic devices illustrated in FIGS. 4A to 4F can have various functions. For example, a function of displaying various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a function of displaying a calendar, date or time, and the like, a function of controlling processing by various software (programs) , A wireless communication function, a function of connecting to various computer networks using the wireless communication function, a function of transmitting or receiving various data using the wireless communication function, reading a program or data recorded on a recording medium, It can have a function of displaying on a display portion, and the like. Further, in an electronic device having a plurality of display units, a function of displaying image information mainly on one display unit and displaying text information mainly on another display unit, or considering parallax on a plurality of display units. The function of displaying a three-dimensional image by displaying the displayed image can be provided. Further, in an electronic device having an image receiving unit, a function of capturing a still image, a function of capturing a moving image, a function of automatically or manually correcting a captured image, and a function of storing a captured image in a recording medium (external or built into a camera) It can have a function of saving, a function of displaying a captured image on a display unit, and the like. Note that the functions of the electronic devices illustrated in FIGS. 4A to 4F are not limited thereto, and the electronic devices can have a variety of functions.

FIG. 4G illustrates a smart watch including a housing 7000, a display portion 7001, operation buttons 7022 and 7023, a connection terminal 7024, a band 7025, a clasp 7026, and the like.

The display portion 7001 mounted on the housing 7000 also serving as a bezel has a non-rectangular display area. The display portion 7001 can display an icon 7027 indicating time, another icon 7028, and the like. Further, the display portion 7001 may be a touch panel (input / output device) equipped with a touch sensor (input device).

Note that the smart watch illustrated in FIG. 4G can have various functions. For example, a function of displaying various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a function of displaying a calendar, date or time, and the like, a function of controlling processing by various software (programs) , A wireless communication function, a function of connecting to various computer networks using the wireless communication function, a function of transmitting or receiving various data using the wireless communication function, reading a program or data recorded on a recording medium, It can have a function of displaying on a display portion, and the like.

In addition, a speaker, a sensor (force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, etc. Including a function of measuring voltage, power, radiation, flow rate, humidity, gradient, vibration, smell or infrared light), a microphone, and the like.

Note that the light-emitting device of one embodiment of the present invention and the display device including the light-emitting element of one embodiment of the present invention can be used for each of the display portions of the electronic devices described in this embodiment, and display with high color purity can be performed. Becomes possible.

Further, as an electronic device to which the light-emitting device is applied, a foldable portable information terminal as shown in FIGS. FIG. 5A illustrates the portable information terminal 9310 in an expanded state. FIG. 5B illustrates the portable information terminal 9310 in a state of being changed from one of an expanded state and a folded state to the other. Further, FIG. 5C illustrates the portable information terminal 9310 in a folded state. The portable information terminal 9310 is excellent in portability in a folded state, and excellent in viewability of display due to a seamless large display area in an expanded state.

The display portion 9311 is supported by three housings 9315 connected by a hinge 9313. Note that the display portion 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). Further, the display portion 9311 can reversibly deform the portable information terminal 9310 from an expanded state to a folded state by bending the two housings 9315 via the hinge 9313. The light-emitting device of one embodiment of the present invention can be used for the display portion 9311. Also, display with good color purity can be performed. A display area 9312 in the display portion 9311 is a display area located on a side surface of the portable information terminal 9310 in a folded state. In the display area 9312, information icons, shortcuts of frequently used applications and programs, and the like can be displayed, so that information can be confirmed and applications and the like can be started smoothly.

FIGS. 6A and 6B show an automobile to which the light-emitting device is applied. That is, the light emitting device can be provided integrally with the automobile. Specifically, the present invention can be applied to a light 5101 (including a rear portion of a vehicle body) outside a car, a wheel 5102 of a tire, a part or the whole of a door 5103 shown in FIG. Further, the present invention can be applied to the display portion 5104, the steering wheel 5105, the shift lever 5106, the seat 5107, the inner rear view mirror 5108, and the like shown in FIG. In addition, you may apply to some glass windows.

As described above, an electronic device or an automobile to which the light-emitting device or the display device of one embodiment of the present invention is applied can be obtained. In this case, display with good color purity can be performed. Note that applicable electronic devices and automobiles are not limited to those described in this embodiment, and can be applied in various fields.

Note that the structure described in this embodiment can be used in appropriate combination with any of the structures described in the other embodiments.

(Embodiment 6)
In this embodiment, a structure of a lighting device manufactured using the light-emitting device which is one embodiment of the present invention or a light-emitting element which is part thereof will be described with reference to FIGS.

FIGS. 7A, 7B, 7C, and 7D show an example of a cross-sectional view of a lighting device. 7A and 7B show a bottom emission type illumination device that extracts light to the substrate side, and FIGS. 7C and 7D show a top emission type illumination device that extracts light to the sealing substrate side. It is a lighting device.

A lighting device 4000 illustrated in FIG. 7A includes a light-emitting element 4002 over a substrate 4001. In addition, a substrate 4003 having irregularities outside the substrate 4001 is provided. The light-emitting element 4002 includes a first electrode 4004, an EL layer 4005, and a second electrode 4006.

The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. Further, an auxiliary wiring 4009 which is electrically connected to the first electrode 4004 may be provided. Note that an insulating layer 4010 is formed over the auxiliary wiring 4009.

Further, the substrate 4001 and the sealing substrate 4011 are bonded with a sealant 4012. Further, a desiccant 4013 is preferably provided between the sealing substrate 4011 and the light-emitting element 4002. Note that the substrate 4003 has unevenness as illustrated in FIG. 7A; thus, the efficiency of extracting light generated in the light-emitting element 4002 can be improved.

Further, instead of the substrate 4003, a diffusion plate 4015 may be provided outside the substrate 4001 as in the lighting device 4100 in FIG. 7B.

The lighting device 4200 in FIG. 7C includes a light-emitting element 4202 over a substrate 4201. The light-emitting element 4202 includes a first electrode 4204, an EL layer 4205, and a second electrode 4206.

The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. Further, an auxiliary wiring 4209 which is electrically connected to the second electrode 4206 may be provided. Further, an insulating layer 4210 may be provided below the auxiliary wiring 4209.

The substrate 4201 and the sealing substrate 4211 having projections and depressions are bonded to each other with a sealant 4212. Further, a barrier film 4213 and a planarization film 4214 may be provided between the sealing substrate 4211 and the light-emitting element 4202. Note that since the sealing substrate 4211 has projections and depressions as illustrated in FIG. 7C, light extraction efficiency of the light-emitting element 4202 can be improved.

Further, instead of the sealing substrate 4211, a diffusion plate 4215 may be provided over the light-emitting element 4202 as in the lighting device 4300 in FIG.

Note that as described in this embodiment, a lighting device having a desired chromaticity can be provided by applying a light-emitting device which is one embodiment of the present invention or a light-emitting element which is part thereof.

Note that the structure described in this embodiment can be used in appropriate combination with any of the structures described in the other embodiments.

(Embodiment 7)
In this embodiment, an application example of a lighting device manufactured using the light-emitting device which is one embodiment of the present invention or a light-emitting element which is part thereof will be described with reference to FIGS.

As an indoor lighting device, the ceiling light 8001 can be applied. The ceiling light 8001 includes a ceiling directly mounted type and a ceiling embedded type. Note that such a lighting device is configured by combining a light emitting device with a housing or a cover. In addition, application to a cord pendant type (cord hanging from the ceiling) is also possible.

In addition, the foot light 8002 can illuminate the floor surface with light, thereby improving the safety of the feet. For example, it is effective to use it for a bedroom, stairs, a passage, and the like. In that case, the size and shape can be appropriately changed according to the size and structure of the room. In addition, a stationary lighting device configured by combining a light emitting device and a support base can be used.

A sheet-like illumination 8003 is a thin sheet-like illumination device. It can be used for a wide range of applications without taking up space because it is used by attaching it to a wall surface. It is easy to increase the area. In addition, it can be used for a wall surface or a housing having a curved surface.

Further, an illumination device 8004 in which light from a light source is controlled only in a desired direction can be used.

Note that in addition to the above, by applying the light-emitting device of one embodiment of the present invention or a light-emitting element which is a part thereof to part of furniture provided in a room, a lighting device having a function as furniture can be provided. can do.

As described above, various lighting devices to which the light-emitting device is applied can be obtained. Note that these lighting devices are one embodiment of the present invention.

The structure described in this embodiment can be used in appropriate combination with any of the structures described in the other embodiments.

<< Synthesis example 1 >>
In this example, an organic compound of one embodiment of the present invention represented by the structural formula (100) in Embodiment 1 and 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-dibenzo [ [a, c] Carbazole (abbreviation: acDBCzPA) will be described. The structure of acDBCzPA is shown below.

In a 200 mL three-necked flask, 3.1 g (7.5 mmol) of 9- (4-bromophenyl) -10-phenylanthracene, 2.0 g (7.5 mmol) of 9H-dibenzo [a, c] carbazole, sodium tert-butoxide 1. 4 g (15 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. 38 mL of xylene was added to this mixture, and the mixture was stirred under reduced pressure to be degassed. To this mixture, 0.3 mL of tri (tert-butyl) phosphine and 43 mg (75 μmol) of bis (dibenzylideneacetone) palladium (0) were added, and the mixture was refluxed at 160 ° C. for 3 hours under a nitrogen stream.

The mixture was filtered and the solid was washed with water. This solid was dissolved in toluene, and this solution was subjected to suction filtration through Celite, alumina, and Florisil. The solid obtained by concentrating the obtained filtrate was recrystallized with toluene to obtain 3.1 g of a target pale yellow solid in a yield of 70%. The synthesis scheme of the above synthesis method is shown in the following formula (a).

3.1 g of the obtained pale yellow solid was sublimated and purified by a train sublimation method. The sublimation purification was performed by heating the pale yellow solid at 300 ° C. under the conditions of a pressure of 3.7 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 2.9 g of a pale yellow solid was obtained at a recovery of 93%.

Nuclear magnetic resonance spectroscopy of the resulting yellow solid analysis result by ^{(1 H-NMR)} is shown below. FIGS. 9A and 9B show ¹ H-NMR charts. Note that FIG. 9B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. 9A is enlarged. From this result, it was found that in this example, an organic compound represented by the above structural formula (100), which is one embodiment of the present invention, acDBCzPA, was obtained.

_{^{1 H NMR (CDCl 3, 300MHz}} ): δ = 7.42-7.69 (m, 15H), 7.76-7.96 (m, 10H), 8.71-8.75 (m, 1H) _{, 8.87 (t, J = 9.0Hz} , 2H), 9.00 (dd, J 1 = 8.4Hz, J 2 = 1.2Hz, 1H).

Next, an ultraviolet-visible absorption spectrum (hereinafter simply referred to as “absorption spectrum”) and an emission spectrum of a toluene solution of acDBCzPA and a solid thin film were measured. The solid thin film was formed on a quartz substrate by a vacuum evaporation method. For measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (solution: V-550, manufactured by JASCO Corporation, thin film: U-4100, manufactured by Hitachi High-Technologies Corporation) was used. The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell, and the absorption spectrum of the thin film was determined by the absorbance (−log ₁₀₎ obtained from the transmittance and the reflectance of the thin film including the substrate. Calculated from [% T / (100-% R)], where% T represents transmittance and% R represents reflectance, and the emission spectrum was measured using a fluorimeter (FS920, manufactured by Hamamatsu Photonics Co., Ltd.). ) Was used.

FIG. 10A shows the measurement results of the absorption spectrum and emission spectrum of a toluene solution of acDBCzPA. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. FIG. 10B shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results in FIG. 10A, in a toluene solution of acDBCzPA, absorption peaks were observed at around 396 nm, 375 nm, 357 nm, and 325 nm, and emission peaks were observed at around 432 nm and 417 nm (excitation wavelength: 376 nm). In addition, from the results in FIG. 10B, in the solid thin film of acDBCzPA, absorption peaks were observed at around 400 nm, 378 nm, 359 nm, 328 nm, and 266 nm, and emission peaks at around 484 nm, 449 nm, and 427 nm (excitation wavelength: 380 nm). It was observed.

It was confirmed that acDBCzPA emitted blue light. The organic compound, acDBCzPA, which is one embodiment of the present invention, can also be used as a host for a light-emitting substance and a fluorescent light-emitting substance in a visible region. In addition, it was found that the acDBCzPA thin film had a good film quality that hardly aggregated even in the air.

The HOMO level and LUMO level of acDBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is described below.

As a measuring device, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used. For the solution in the CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate as a supporting electrolyte was used. n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the object to be measured is further dissolved to a concentration of 2 mmol / L. did.

As a working electrode, a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.), and as an auxiliary electrode, a platinum electrode (Pt counter electrode, VC-3, manufactured by BAS Co., Ltd.) 5 cm)) and an Ag / Ag ⁺ electrode (RE7 non-aqueous solvent-based reference electrode manufactured by BAS Inc.) was used as a reference electrode. The measurement was performed at room temperature (20 to 25 ° C.).

Further, the scan speed at the time of CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured. Ea was the intermediate potential of the oxidation-reduction wave, and Ec was the intermediate potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] =-4.94-Ea, LUMO The HOMO level and the LUMO level can be obtained from the equation [level [eV] = − 4.94−Ec].

Further, the CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.

As a result, in the measurement of the oxidation potential Ea [V] of acDBCzPA, it was found that the HOMO level was −5.75 eV. On the other hand, in measurement of the reduction potential Ec [V], it was found that the LUMO level was -2.74 eV. Further, when compared with the waveforms after the first cycle and after 100 cycles in the repetitive measurement of the oxidation-reduction wave, the peak intensity of 80% was maintained in the Ea measurement, so that acDBCzPA has very good resistance to oxidation. Was confirmed.

<< Synthesis Example 2 >>
In this example, an organic compound of one embodiment of the present invention, which is represented by the structural formula (101) of Embodiment 1 and has a structure of 7- [4- (10-phenyl-9-anthryl) phenyl] -7H-tribenzo [ [a, c, g] carbazole (abbreviation: acgTBCzPA) will be described. The structure of acgTBCzPA is shown below.

1.3 g (3.2 mmol) of 9- (4-bromophenyl) -10-phenylanthracene, 1.0 g (3.2 mmol) of 7H-tribenzo [a, c, g] carbazole, sodium tert-butoxide in a 200 mL three-necked flask 0.61 g (6.4 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. 16 mL of xylene was added to this mixture, and the mixture was stirred under reduced pressure to be degassed. To this mixture, 0.6 mL of tri (tert-butyl) phosphine and 86 mg (0.15 mmol) of bis (dibenzylideneacetone) palladium (0) were added, and the mixture was refluxed at 160 ° C. for 20 hours under a nitrogen stream.

The mixture was filtered and the solid was washed with water. This solid was purified by silica gel column chromatography (toluene: hexane = 1: 3), and further recrystallized from toluene to obtain 1.0 g of a target pale yellow solid in a yield of 48%. The synthesis scheme of the above synthesis method is shown in the following formula (b).

1.0 g of the obtained pale yellow solid was sublimated and purified by a train sublimation method. The sublimation purification was performed by heating the pale yellow solid at 290 ° C. under the conditions of a pressure of 3.2 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 0.92 g of a pale yellow solid was obtained at a recovery of 93%.

Analysis result by nuclear magnetic resonance spectroscopy ^{(1 H-NMR)} of pale yellow solid thus obtained are shown below. FIGS. 11A and 11B show ¹ H-NMR charts. Note that FIG. 11B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. 11A is enlarged. From this result, it was found that in this example, acgTBCzPA, an organic compound of one embodiment of the present invention represented by the above structural formula (101), was obtained.

¹ H NMR (CDCl ₃ , 300 MHz): δ = 7.40-7.82 (m, 23H), 7.91-7.94 (m, 3H), 8.09 (d, J = 7.2 Hz, 1H), 8.82-8.87 (m, 2H), 9.18 (d, J = 8.4 Hz, 1H), 9.24 (d, J = 7.8 Hz, 1H).

Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as an “absorption spectrum”) and an emission spectrum of a toluene solution of acgTBCzPA and a solid thin film were measured. The solid thin film was formed on a quartz substrate by a vacuum evaporation method. For measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (solution: V-550, manufactured by JASCO Corporation, thin film: U-4100, manufactured by Hitachi High-Technologies Corporation) was used. The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell, and the absorption spectrum of the thin film was determined by the absorbance (−log ₁₀ [%) determined from the transmittance and the reflectance including the substrate. T / (100-% R)], where% T represents transmittance and% R represents reflectance, and a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics Co., Ltd.) was used for measuring the emission spectrum. Using.

FIG. 12A shows the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. FIG. 12B shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

12A, in the toluene solution of acgTBCzPA, absorption peaks were observed at around 396 nm, 376 nm, 361 nm and 346 nm, and emission peaks were observed at around 434 nm and 417 nm (excitation wavelength: 376 nm). In addition, from the result of FIG. 12B, in the solid thin film of acgTBCzPA, an absorption peak is observed at around 402 nm, 380 nm, 365 nm, 345 nm, 305 nm, and 266 nm, and an emission wavelength peak is observed at around 443 nm (excitation wavelength: 380 nm). Was done.

In addition, it was confirmed that acgTBCzPA emitted blue light. The organic compound, acgTBCzPA, which is one embodiment of the present invention, can also be used as a host for a light-emitting substance and a fluorescent light-emitting substance in a visible region. In addition, it was found that the thin film of acgTBCzPA has a good film quality that does not easily aggregate even in the atmosphere.

The HOMO level and LUMO level of acgTBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is described below.

As a measuring device, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used. For the solution in the CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate as a supporting electrolyte was used. n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the object to be measured is further dissolved to a concentration of 2 mmol / L. did.

As a working electrode, a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.), and as an auxiliary electrode, a platinum electrode (Pt counter electrode, VC-3, manufactured by BAS Co., Ltd.) 5 cm)) and an Ag / Ag ⁺ electrode (RE7 non-aqueous solvent-based reference electrode manufactured by BAS Inc.) was used as a reference electrode. The measurement was performed at room temperature (20 to 25 ° C.).

Further, the scan speed at the time of CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured. Ea was the intermediate potential of the oxidation-reduction wave, and Ec was the intermediate potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] =-4.94-Ea, LUMO The HOMO level and the LUMO level can be obtained from the equation [level [eV] = − 4.94−Ec].

Further, the CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.

As a result, in the measurement of the oxidation potential Ea [V] of acgTBCzPA, it was found that the HOMO level was −5.64 eV. On the other hand, in measurement of the reduction potential Ec [V], it was found that the LUMO level was -2.75 eV.

In this embodiment, as a light-emitting element which is one embodiment of the present invention, a light-emitting element 1 in which acDBCzPA (structural formula (100)) is used for a light-emitting layer described in Embodiment 1 and an acgTBCzPA ( The light emitting element 2 using the structural formula (101)) in the light emitting layer, the organic compound to be compared, and the comparative light emitting element 3 using the cgDBCzPA (structural formula (201)) in the light emitting layer have these element structures, manufacturing methods, and The characteristics will be described. Note that the element structure of the light-emitting element used in this embodiment is shown in FIG. 13 and the specific structure is shown in Table 1. The chemical formula of the material used in this example is shown below.

<< Production of light-emitting element >>
The light-emitting element described in this embodiment has a hole-injection layer 911, a hole-transport layer 912, a light-emitting layer 913, an electron-transport layer 914 over a first electrode 901 formed over a substrate 900 as shown in FIG. It has a structure in which an electron injection layer 915 is sequentially stacked and a second electrode 903 is stacked over the electron injection layer 915.

First, a first electrode 901 was formed over a substrate 900. The electrode area was 4 mm ² (2 mm × 2 mm). Further, a glass substrate was used as the substrate 900. The first electrode 901 was formed using indium tin oxide containing silicon oxide (ITSO) with a thickness of 70 nm by a sputtering method.

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. Thereafter, the substrate was introduced into a vacuum evaporation apparatus having an internal pressure reduced to about 10 ⁻⁴ Pa, and baked at 170 ° C. for 60 minutes in a heating chamber in the vacuum evaporation apparatus, and then the substrate was released for about 30 minutes. Cooled down.

Next, a hole-injection layer 911 was formed over the first electrode 901. After the pressure in the vacuum evaporation apparatus is reduced to 10 ⁻⁴ Pa, the hole injection layer 911 is formed of 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPPn) and molybdenum oxide. Were formed by co-evaporation so that PCPPn: molybdenum oxide = 4: 2 (mass ratio) and a film thickness of 10 nm.

Next, a hole transport layer 912 was formed over the hole injection layer 911. The hole transport layer 912 was formed using PCPPn by vapor deposition so as to have a thickness of 30 nm.

Next, a light-emitting layer 913 was formed over the hole-transport layer 912.

In the case of the light-emitting element 1, the light-emitting layer 913 uses acDBCzPA as a host material and N, N′-bis (3-methylphenyl) -N, N′-bis [3- (9-phenyl-9H) as a guest material. -Fluoren-9-yl) phenyl] -pyrene-1,6-diamine (abbreviation: 1,6 mMemFLPAPrn) and co-evaporated so that the weight ratio was acDBCzPA: 1,6 mMemFLPAPrn = 1: 0.03. The thickness was 25 nm.

For the light-emitting layer 913, in the case of the light-emitting element 2, acgTBCzPA was used as a host material, 1,6 mMemFLPAPrn was used as a guest material, and co-evaporation was performed so that the weight ratio was acgTBCzPA: 1,6memFLPAPrn = 1: 0.03. The thickness was 25 nm.

For the light-emitting layer 913, in the case of the comparative light-emitting element 3, cgDBCzPA was used as a host material, 1,6 mMemFLPAPrn was used as a guest material, and co-evaporation was performed so that the weight ratio was cgDBCzPA: 1,6memFLPAPrn = 1: 0.03. . The thickness was 25 nm.

Next, an electron transport layer 914 was formed over the light-emitting layer 913. In the case of the light-emitting element 1, the electron-transport layer 914 was formed by vapor deposition so that the thickness of acDBCzPA was 15 nm and the thickness of bathophenanthroline (abbreviation: Bphen) was 10 nm. In the case of the light-emitting element 2, the light-emitting element 2 was formed by vapor deposition so that the thickness of acgTBCzPA was 15 nm and the thickness of Bphen was 10 nm. In the case of Comparative Light-Emitting Element 3, it was formed by vapor deposition in such a manner that the thickness of cgDBCzPA was 15 nm and the thickness of Bphen was 10 nm.

Next, an electron-injection layer 915 was formed over the electron-transport layer 914. The electron-injection layer 915 was formed using lithium fluoride (LiF) by evaporation to a thickness of 1 nm.

Next, a second electrode 903 was formed over the electron-injection layer 915. The second electrode 903 was formed by evaporation of aluminum to have a thickness of 200 nm. Note that in this embodiment, the second electrode 903 functions as a cathode.

Through the above steps, a light-emitting element in which an EL layer was interposed between a pair of electrodes was formed over the substrate 900. Note that the hole-injection layer 911, the hole-transport layer 912, the light-emitting layer 913, the electron-transport layer 914, and the electron-injection layer 915 described in the above steps are functional layers included in an EL layer of one embodiment of the present invention. In addition, in all of the evaporation steps in the above manufacturing method, an evaporation method by a resistance heating method was used.

Further, the light-emitting element manufactured as described above is sealed with another substrate (not shown). Note that when sealing using another substrate (not shown), another substrate (not shown) is fixed on the substrate 900 using a sealing material in a glove box in a nitrogen atmosphere, and sealing is performed. The material was applied to the periphery of the light emitting element formed over the substrate 900, irradiated with ultraviolet light of 365 nm at 6 J / cm ² at the time of sealing, and heat-treated at 80 ° C. for 1 hour.

動作 Operating characteristics of light emitting device 素 子
The operating characteristics of the manufactured light-emitting elements 1 and 2 were measured. The measurement was performed at room temperature. 14 to 17 show the results of the operation characteristics of the light-emitting elements 1 and 2. FIG.

Table 2 below shows main initial characteristic values of the light-emitting elements 1 and ^{2 at} around 1000 cd / m ² .

From the above results, it can be seen that each light-emitting element manufactured in this example has good current efficiency and high external quantum efficiency.

FIG. 18 shows emission spectra obtained when current was applied to the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 at a current density of 12.5 mA / cm ² . As shown in FIG. 18, the emission spectra of Light-Emitting Element 1, Light-Emitting Element 2, and Comparative Light-Emitting Element 3 each have a peak near 468 nm, which is derived from the emission of 1,6 mMemFLPAPrn contained in the light-emitting layer 913. It is suggested that you do.

Next, a reliability test was performed on the light-emitting element 1 and the comparative light-emitting element 3. FIG. 19 shows the results of the reliability test. In FIG. 19, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. The reliability test was a constant current drive test at 2 mA.

From the result of the reliability test, it was found that the light-emitting element 1 which is one embodiment of the present invention exhibited characteristics superior to the comparative light-emitting element 3 in reliability. Thus, even when the same light emitting material (1,6 mMemFLPAPrn) is used, using acDBCzPA (structural formula (100)) described in Example 1 as a light emitting layer host is useful for extending the life. It can be said that

<< Synthesis example 3 >>
In this example, an organic compound of one embodiment of the present invention represented by the structural formula (102) in Embodiment 1 and 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-tribenzo [ [a, c, i] Carbazole (abbreviation: aciTBCzPA) will be described. The structure of aciTBCzPA is shown below.

1.7 g (4.1 mmol) of 9- (4-bromophenyl) -10-phenylanthracene, 1.3 g (4.1 mmol) of 9H-tribenzo [a, c, i] carbazole in a 200 mL three-neck flask, sodium tert-butoxide 0.38 g (8.2 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. 20 mL of xylene was added to this mixture, and the mixture was degassed by stirring under reduced pressure. 0.85 mL of tri (tert-butyl) phosphine and 0.12 g (0.21 mmol) of bis (dibenzylideneacetone) palladium (0) were added to this mixture, and the mixture was refluxed at 150 ° C. for 12 hours under a nitrogen stream.

The mixture was filtered and the solid was washed with water. This solid was dissolved in toluene, and this solution was subjected to suction filtration through Celite, alumina, and Florisil. The solid obtained by concentrating the obtained filtrate was recrystallized with toluene. The obtained solid was purified by HPLC, and the obtained solid was recrystallized from toluene to give 1.2 g of a target white solid in a yield of 46%. The synthesis scheme of the above synthesis method is shown in the following formula (c).

1.2 g of the obtained white solid was sublimated and purified by a train sublimation method. The sublimation purification was performed by heating the pale yellow solid at 305 ° C. under the conditions of a pressure of 4.0 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 1.0 g of a pale yellow solid was obtained at a recovery of 85%.

Analysis result by nuclear magnetic resonance spectroscopy ^{(1 H-NMR)} of pale yellow solid thus obtained are shown below. FIGS. 20A and 20B show ¹ H-NMR charts. Note that FIG. 20B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. 20A is enlarged. From this result, it was found that in this example, an organic compound of one embodiment of the present invention, aciTBCzPA, represented by the above structural formula (102) was obtained.

_{^{1 H NMR (CDCl 3, 300MHz}} ): δ = 7.39-7.71 (m, 15H), 7.79-7.92 (m, 7H), 7.98-8.10 (m, 5H) _{, 8.86-8.92 (m, 3H),} 9.14 (dd, J 1 = 8.4Hz, J 2 = 0.9Hz, 1H).

Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and an emission spectrum of a toluene solution and a solid thin film of aciTBCzPA were measured. The solid thin film was formed on a quartz substrate by a vacuum evaporation method. For measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (solution: V-550, manufactured by JASCO Corporation, thin film: U-4100, manufactured by Hitachi High-Technologies Corporation) was used. The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell, and the absorption spectrum of the thin film was determined by the absorbance (−log ₁₀ [%) determined from the transmittance and the reflectance including the substrate. T / (100-% R)], where% T represents transmittance and% R represents reflectance, and a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics Co., Ltd.) was used for measuring the emission spectrum. Using.

FIG. 21A shows the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. FIG. 21B shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results of FIG. 21A, in the toluene solution of aciTBCzPA, absorption peaks are observed at around 396 nm, 374 nm, 362 nm, 354 nm, 346 nm, and 337 nm, and emission peaks are observed at around 433 nm and 414 nm (excitation wavelength: 376 nm). Was done. In addition, from the results of FIG. 21B, in the solid thin film of aciTBCzPA, absorption peaks are observed at around 400 nm, 378 nm, 360 nm, 300 nm, and 264 nm, and emission peaks are observed at around 445 nm and 430 nm (excitation wavelength 365 nm). Was done.

In addition, it was confirmed that aciTBCzPA emitted blue light. The organic compound, aciTBCzPA, which is one embodiment of the present invention, can also be used as a host for a light-emitting substance or a fluorescent light-emitting substance in a visible region. In addition, it was found that the thin film of aciTBCzPA has a good film quality that does not easily aggregate even in the atmosphere.

The HOMO level and LUMO level of aciTBCzPA were calculated based on cyclic voltammetry (CV) measurement. The calculation method is described below.

As a measuring device, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used. For the solution in the CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate as a supporting electrolyte was used. n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the object to be measured is further dissolved to a concentration of 2 mmol / L. did.

As a working electrode, a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.), and as an auxiliary electrode, a platinum electrode (Pt counter electrode, VC-3, manufactured by BAS Co., Ltd.) 5 cm)) and an Ag / Ag ⁺ electrode (RE7 non-aqueous solvent-based reference electrode manufactured by BAS Inc.) was used as a reference electrode. The measurement was performed at room temperature (20 to 25 ° C.).

Further, the scan speed at the time of CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] with respect to the reference electrode were measured. Ea was the intermediate potential of the oxidation-reduction wave, and Ec was the intermediate potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] =-4.94-Ea, LUMO The HOMO level and the LUMO level can be obtained from the equation [level [eV] = − 4.94−Ec].

Further, the CV measurement was repeated 100 times, and the electrical stability of the compound was examined by comparing the oxidation-reduction wave in the measurement at the 100th cycle with the oxidation-reduction wave at the first cycle.

As a result, in the measurement of the oxidation potential Ea [V] of aciTBCzPA, it was found that the HOMO level was −5.74 eV. On the other hand, in measurement of the reduction potential Ec [V], it was found that the LUMO level was -2.76 eV. In addition, when compared with the waveforms after the first cycle and after 100 cycles in the repetitive measurement of the oxidation-reduction wave, since the peak intensity was maintained at 84% in the Ea measurement, aciTBCzPA has very good resistance to oxidation. It was confirmed that there was.

<< Synthesis example 4 >>
In this example, an organic compound of one embodiment of the present invention, which is represented by the structural formula (103) of Embodiment 1 and has 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-tetrabenzo [ [a, c, g, i] A method for synthesizing carbazole (abbreviation: TeBCzPA) will be described. The structure of TeBCzPA is shown below.

1.2 g (3.0 mmol) of 9- (4-bromophenyl) -10-phenylanthracene, 1.1 g (3.0 mmol) of 9H-tetrabenzo [a, c, g, i] carbazole in a 200 mL three-neck flask, sodium tert -Butoxide (0.58 g, 6.0 mmol) was added, and the atmosphere in the flask was replaced with nitrogen. 16 mL of mesitylene was added to the mixture, and the mixture was degassed by stirring under reduced pressure. To this mixture, 0.61 mL of tri (tert-butyl) phosphine and 86 mg (0.15 mmol) of bis (dibenzylideneacetone) palladium (0) were added, and the mixture was stirred at 140 ° C. for 20 hours under a nitrogen stream.

The mixture was filtered and the solid was washed with water. This solid was purified by silica gel column chromatography (toluene: hexane = 1: 4) and recrystallized from toluene. The obtained solid was purified by HPLC, and the obtained solid was recrystallized from toluene. As a result, 0.76 g of a target pale yellow solid was obtained in a yield of 36%. The synthesis scheme of the above synthesis method is shown in the following formula (d).

Analysis result by nuclear magnetic resonance spectroscopy ^{(1 H-NMR)} of pale yellow solid thus obtained are shown below. In addition, FIGS. 22A and 22B show ¹ H-NMR charts. Note that FIG. 22B is a chart in which the range of 7.0 ppm to 9.5 ppm in FIG. 22A is enlarged. From this result, it was found that in this example, an organic compound of one embodiment of the present invention, TeBCzPA, represented by the above structural formula (103), was obtained.

¹ H NMR (CDCl ₃ , 300 MHz): δ = 7.42-7.49 (m, 4H), 7.53-7.71 (m, 15H), 7.81 (d, J = 8.7 Hz, 2H), 7.87-7.90 (m, 2H), 7.98-8.04 (m, 4H), 8.78-8.81 (m, 2H), 8.86 (d, J = 7.8 Hz, 2H), 9.06-9.10 (m, 2H).

Next, an ultraviolet-visible absorption spectrum and an emission spectrum of a toluene solution of TeBCzPA were measured. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (solution: manufactured by JASCO Corporation, V-550) was used. The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell. The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics Co., Ltd.).

FIG. 23 shows the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

From the results shown in FIG. 23, in the toluene solution of TeBCzPA, absorption peaks were observed at around 396 nm, 373 nm, 356 nm, 340 nm, and 303 nm, and emission peaks were observed at around 433 nm, 415 nm (excitation wavelength: 374 nm).

In addition, it was confirmed that TeBCzPA emitted blue light. The organic compound, TeBCzPA, which is one embodiment of the present invention, can also be used as a host for a light-emitting substance or a fluorescent light-emitting substance in a visible region.

In this example, as a light-emitting element which is one embodiment of the present invention, a light-emitting element 4 in which aciTBCzPA (structural formula (102)) described in Example 4 was used for a light-emitting layer was manufactured and its characteristics were measured. Is shown.

The element structure of the light emitting element used in this example is the same as that shown in FIG. 13 shown in Example 3, but the specific structure of each layer constituting the element structure is as shown in Table 3. . The chemical formula of the material used in this example is shown below.

動作 Operating characteristics of light emitting device 素 子
The operating characteristics of the manufactured light-emitting element 4 were measured. The measurement was performed at room temperature. The results are shown in FIGS.

Table 4 below shows main initial characteristic values of the light-emitting element at around 1000 cd / m ² .

From the above results, it can be seen that the light-emitting element 4 manufactured in this example is driven at a very low voltage and exhibits good efficiency.

FIG. 28 shows an emission spectrum when a current was applied to the light-emitting element 4 at a current density of 12.5 mA / cm ² . As shown in FIG. 28, the emission spectrum of the light-emitting element has a peak near 469 nm, which suggests that the light-emitting element is derived from light emission of a light-emitting substance included in the light-emitting layer 913.

Next, a reliability test was performed on the light-emitting element 4. FIG. 29 shows the results of the reliability test. In FIG. 29, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. The reliability test was a constant current drive test at 2 mA.

From the result of the reliability test, it was found that the light-emitting element 4 which is one embodiment of the present invention exhibited excellent characteristics in reliability. Accordingly, it can be said that using an organic compound, aciTBCzPA (Structural Formula (102)), which is one embodiment of the present invention, as a light-emitting layer host is useful for extending the life.

101 first electrode 102 second electrode 103 EL layer 103a, 103b EL layer 104 charge generation layer 111, 111a, 111b hole injection layer 112, 112a, 112b hole transport layer 113, 113a, 113b light emitting layer 114, 114a , 114b Electron transport layer 115, 115a, 115b Electron injection layer 201 First substrate 202 Transistor (FET)
203R, 203G, 203B, 203W Light emitting element 204 EL layer 205 Second substrate 206R, 206G, 206B Color filter 206R ', 206G', 206B 'Color filter 207 First electrode 208 Second electrode 209 Black layer (black matrix) )
210R, 210G Conductive layer 301 First substrate 302 Pixel portion 303 Drive circuit portion (source line drive circuit)
304a, 304b drive circuit section (gate line drive circuit)
305 Sealant 306 Second substrate 307 Routing wiring 308 FPC
309 FET
310 FET
311 FET
312 FET
313 first electrode 314 insulator 315 EL layer 316 second electrode 317 light emitting element 318 space 900 substrate 901 first electrode 902 EL layer 903 second electrode 911 hole injection layer 912 hole transport layer 913 light emitting layer 914 Electron transport layer 915 electron injection layer 4000 lighting device 4001 substrate 4002 light emitting element 4003 substrate 4004 first electrode 4005 EL layer 4006 second electrode 4007 electrode 4008 electrode 4009 auxiliary wiring 4010 insulating layer 4011 sealing substrate 4012 sealant 4013 desiccant 4015 diffusion plate 4100 lighting device 4200 lighting device 4201 substrate 4202 light emitting element 4204 first electrode 4205 EL layer 4206 second electrode 4207 electrode 4208 electrode 4209 auxiliary wiring 4210 insulating layer 4211 sealing substrate 4212 sealing material 4213 ba A film 4214 Flattening film 4215 Diffusion plate 4300 Lighting device 5101 Light 5102 Wheel 5103 Door 5104 Display unit 5105 Handle 5106 Shift lever 5107 Seat seat 5108 Inner rear view mirror 7000 Housing 7001 Display unit 7002 Second display unit 7003 Speaker 7004 LED lamp 7005 Operation key 7006 Connection terminal 7007 Sensor 7008 Microphone 7009 Switch 7010 Infrared port 7011 Recording medium reading unit 7012 Support unit 7013 Earphone 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7020 Camera 7021 External connection unit 7022, 7023 Operation button 7024 Connection terminal 7025 band,
7026 Clasp 7027 Icon 7028 indicating time 7082 Other icons 8001 Lighting device 8002 Lighting device 8003 Lighting device 8004 Lighting device 9310 Personal digital assistant 9311 Display portion 9312 Display region 9313 Hinge 9315 Housing

Claims (11)

An organic compound represented by the general formula (G1).

(In the formula, Ar ¹ represents a substituted or unsubstituted phenylene group. Further, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted 5 to 7 carbon atoms. R ⁹ represents a monocyclic saturated hydrocarbon, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. And R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, wherein the benzene ring is unsubstituted or an alkyl group having 1 to 6 carbon atoms as a substituent. A substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl having 6 to 13 carbon atoms Having one of the groups: An organic compound represented by a general formula (G2).

(In the formula, Ar ² represents an unsubstituted phenylene group. Further, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent group having 5 to 7 carbon atoms. cyclic saturated hydrocarbons, represents any of polycyclic saturated hydrocarbon or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted 7-10 carbon atoms. also, R ⁹ and R ¹⁰ and R ¹¹ and R ¹² may be independently condensed to form a benzene ring, and the benzene ring is unsubstituted or has an alkyl group having 1 to 6 carbon atoms as a substituent; Or an unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms Having either one.) An organic compound represented by a general formula (G3).

(Wherein, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon number, Represents a polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and R ⁹ and R ¹⁰ and R ¹¹ and R ¹² each independently represent The benzene ring may be unsubstituted or an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic group having 5 to 7 carbon atoms, It has a saturated hydrocarbon, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.) An organic compound represented by a general formula (G4).

(Wherein, R ^{1 to} R ²¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted carbon number, Represents a polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and at least one of R ⁹ and R ¹⁰ , and R ¹¹ and R ¹² is Condensed to form a benzene ring, and the benzene ring is unsubstituted or an alkyl group having 1 to 6 carbon atoms as a substituent, or a substituted or unsubstituted monocyclic saturated group having 5 to 7 carbon atoms. It has any of a hydrocarbon, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.) An organic compound represented by the structural formula (100), the structural formula (101), the structural formula (102), or the structural formula (103).

  A light-emitting element using the organic compound according to claim 1. Having an EL layer between the pair of electrodes,
A light-emitting element having the organic compound according to any one of claims 1 to 5, wherein the EL layer includes the organic compound. Having an EL layer between the pair of electrodes,
The EL layer has a light emitting layer,
A light-emitting device comprising the organic compound according to claim 1, wherein the light-emitting layer includes the organic compound according to claim 1. A light emitting device according to claim 6,
At least one of a transistor or a substrate;
A light emitting device having: A light emitting device according to claim 9,
At least one of a microphone, a camera, an operation button, an external connection unit, or a speaker,
Electronic equipment having A light emitting device according to claim 6,
At least one of a housing, a cover, or a support,
Lighting device having a.

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