Light-emitting element

Abstract

To provide a light emitting element using a novel organic compound, benzofuropyrimidine derivative or benzothienopyrimidine derivative, in a light emitting layer.SOLUTION: A light emitting element includes a pair of electrodes, and a light emitting layer between the pair of electrodes, the light emitting layer includes a first organic compound represented by the formula (G1), a second organic compound, and an organometallic complex, and the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative or a dibenzofuran derivative, and the first organic compound and the second organic compound are a combination that forms an exciplex.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] 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. However, one embodiment of the present invention is not limited to the above technical fields. The present invention relates to an object, a method, a manufacturing method, or a driving method. process, machine, manufacture, or composition of matter Specifically, the present invention relates to a semiconductor device, a display device, a liquid crystal display device, etc. It is possible. [Background technology]

[0002] Light-emitting elements (also called organic EL elements) are thin, lightweight, and have an EL layer sandwiched between a pair of electrodes. These features include high-speed response to input signals and low power consumption. This display is attracting attention as the next generation of flat panel displays.

[0003] The light-emitting element is a device that emits light by applying a voltage between a pair of electrodes, and the electrons injected from each electrode are The electrons and holes recombine in the EL layer, and the luminescent material (organic compound) contained in the EL layer becomes excited. When the excited state returns to the ground state, light is emitted. , singlet excited state (S * ) and triplet excited states (T * ) and emission from the singlet excited state. The light emitted from the triplet excited state is called fluorescence, and the light emitted from the triplet excited state is called phosphorescence. The statistical generation ratio of these is S * :T * =1:3. From luminous materials The emission spectrum obtained is specific to the luminescent material, and different types of organic compounds emit By using it as a light-emitting substance, light-emitting elements with various emission colors can be obtained.

[0004] Regarding such light-emitting elements, in order to improve their element characteristics, improvements in the element structure and material development etc. are being actively carried out (for example, see Patent Document 1).

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] Therefore, in one aspect of the present invention, a novel organic compound is provided. Also, in another aspect of the present invention a benzofuropyrimidine derivative or a benzothienopyrimidine derivative, which is a novel organic compound, is provided. Also, in one aspect of the present invention, a novel organic compound that can be used in a light-emitting element is provided. Also, in one aspect of the present invention, a novel organic compound that can be used in the EL layer of a light-emitting element is provided. Also, a novel and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. Note that the description of these problems does not prevent the existence of other problems from existing. Note that one aspect of the present invention does not necessarily have to solve all of these problems necessarily. Note that other problems other than these will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. ​

Means for Solving the Problem

[0007] One aspect of the present invention is a benzofuropyrimidine derivative or a benzothienopyrimidine derivative, which is an organic compound represented by the following general formula (G1). Further, as represented by the following general formula (G1), an aromatic hydrocarbon ring is linked at the 8-position of the benzofuropyrimidine skeleton or the benzothienopyrimidine skeleton (specifically, 2 to 4 aromatic hydrocarbon rings are linked), and it has a structure.

[0008]

Chemical Formula

[0009] In the above general formula (G1), Q represents oxygen or sulfur. Ar 1 , Ar 2 , Ar 3 , and and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, and the substituent of the aromatic hydrocarbon ring is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Further, m and n are each 0 or 1. Also , A is a group having 12 to 100 carbon atoms and has any one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, or a triphenylamine structure. Further, R is hydrogen 1 ​ , an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0010] Another aspect of the present invention is a benzofuropyrimidine derivative or a benzothienopyrimidine derivative, which is an organic compound represented by the following general formula (G2). Also, as represented by the following general formula ( G2), it has a structure in which a plurality of aromatic hydrocarbon rings are linked to the 8-position of the benzofuropyrimidine skeleton or the benzothienopyrimidine skeleton (specifically, 2 to 4 aromatic hydrocarbon rings are linked) and has a skeleton having at least hole transporting property at the 4-position.

[0011]

Chemical formula

[0012] In the above general formula (G2), Q represents oxygen or sulfur. Ar 1 , Ar 2 , Ar 3 , and Ar 4 represent the same group, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring . The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. The number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Also, m and n are each 0 or is 1. Further, α represents a substituted or unsubstituted phenylene group, and t represents an integer from 0 to 4. represents. Also, Ht uni represents a skeleton having hole transporting properties. Also, R 1 is hydrogen, carbon an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms , a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted hetero aryl group having 3 to 12 carbon atoms.

[0013] Another aspect of the present invention is a benzofuropyrimidine derivative or benzothienopyrimi dine derivative, which is an organic compound represented by the following general formula (G3). Also, as represented by the following general formula ( G3), it has a structure in which a plurality of aromatic hydrocarbon rings are linked to the 8-position of the benzofuropyrimidine skeleton or benzothienopyrimidine skeleton (specifically, 2 to 4 aromatic hydrocarbon rings are linked) and has a skeleton having hole transporting properties via a phenylene group at the 4-position.

[0014]

Chemical formula

[0015] In the above general formula (G3), Q represents oxygen or sulfur. Ar 1 , Ar 2 , Ar 3 , and and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, and the substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms , or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic It is either a saturated hydrocarbon group of the formula or a cyano group, and the carbon atoms forming the aromatic hydrocarbon ring are 6 or more and 25 or less. Also, m and n are each 0 or 1. Also , Ht uni represents a skeleton having hole-transporting properties. Also, R 1 is hydrogen, an alkyl group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms which is substituted or unsubstituted, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms which is substituted or unsubstituted , a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms .

[0016] Another aspect of the present invention is a benzofuropyrimidine derivative or a benzothienopyrimidine derivative, which is an organic compound represented by the following general formula (G4). Also, as represented by the following general formula ( G4), it has a structure in which a plurality of aromatic hydrocarbon rings are linked (specifically, 2 to 4 aromatic hydrocarbon rings are linked) to the 8-position of the benzofuropyrimidine skeleton or the benzothienopyrimidine skeleton , and has a skeleton having hole-transporting properties via a biphenyldiyl group at the 4-position.

[0017]

Chemical formula

[0018] In the above general formula (G4), Q represents oxygen or sulfur. Ar 1 , Ar 2 , Ar 3 , and and Ar 4 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring, and the substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms a xylyl group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Also, m and n are each 0 or 1. Also, uni Ht 1 represents a skeleton having hole transporting properties. Also, R is hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or

[0019] In each of the above configurations, Ht in the general formulas (G2), (G3), and (G4) u ni each independently has any one of a pyrrole ring structure, a furan ring structure, or a thiophene ring structure.

[0020] Also, in each of the above configurations, Ht in the general formulas (G2), (G3), and (G4) u ni is each independently any one of the following general formulas (Ht-1) to (Ht-26).

[0021]

Chemical formula

[0022] In the general formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. Also, R ~R 2 ~R 71 each represent 1 to 4 substituents, and each independently represents water It represents any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. Also, Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0023] In each of the above configurations, A in the general formulas (G1), (G2), (G3), and (G4) r 1 , Ar 2 , Ar 3 , and Ar 4 are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0024] Also, in each of the above configurations, Ar in the general formulas (G1), (G2), (G3), and (G4) among, Ar 1 , Ar 2 , Ar 3 , and Ar 4 are the same.

[0025] Also, in each of the above configurations, Ar in the general formulas (G1), (G2), (G3), and (G4) among, Ar 1 , Ar 2 , Ar 3 , and Ar 4 are unsubstituted.

[0026] Also, in each of the above configurations, the following general formula (G-X), which is a partial structure in the general formulas (G1), (G2), (G3), and (G4), is represented by any one of the following structural formulas (G-X-p1) to (G-X-p12) and (G-X-n1) to (G-X-n6). among, Ar p12) and (G-X-n1) to (G-X-n6).

[0027]

Chemical formula

[0028]

Chemical formula

[0029] Another aspect of the present invention is any one of the organic compounds represented by Structural Formula (100), (101), or (102). That is, it is an organic compound represented by any one of them.

[0030]

Chemical Formula

[0031] Another aspect of the present invention is a light-emitting element using the organic compound which is one aspect of the present invention described above. In addition, a light-emitting element having a guest material in addition to the above organic compound is also included in the present invention. Also, a light-emitting element having a phosphorescent material in addition to the above organic compound is included in the present invention. Furthermore, a light-emitting element having a phosphorescent material and a carbazole derivative in addition to the above organic compound is also included in the present invention. Note that the carbazole derivative includes a biscarbazole derivative or an aromatic amine having a carbazolyl group.

[0032] Another aspect of the present invention is a light-emitting element using the organic compound which is one aspect of the present invention described above. Note that a light-emitting element formed by using the organic compound which is one aspect of the present invention in the EL layer between a pair of electrodes or in the light-emitting layer included in the EL layer is also included in the present invention. In addition, when there is a layer having an organic compound (for example, a cap layer) in contact with the electrode in addition to the above light-emitting element, it is also included in the light-emitting element and thus included in the present invention. Also, in addition to the light-emitting element, a light-emitting device having a transistor, a substrate, etc. is included in the scope of the invention. Furthermore, in addition to these light-emitting devices, electronic devices and lighting devices having a microphone, a camera, an operation button, an external connection part, a housing, a cover, a support base, or a speaker, etc. are also included in the scope of the invention.

[0033] ​​​​​​​​​​​​ Another embodiment of the present invention includes a light-emitting device having a light-emitting element, and further includes a lighting device having the light-emitting device. Therefore, the term "light-emitting device" in this specification includes a light-emitting device such as an image display device. It also refers to a light source (including lighting equipment) that is connected to a light-emitting device, such as an FPC (Fl exible printed circuit) or TCP (Tape Carrier A module with a connector such as a printer package, a TCP A module with a printed wiring board or a light emitting element with COG (Chip On Glass) All modules with ICs directly mounted using the assembly method are included in the light emitting device. It shall be so. Effect of the Invention

[0034] In one embodiment of the present invention, a novel organic compound can be provided. In one embodiment, novel organic compounds, benzofuropyrimidine derivatives or benzothienopyrimidine derivatives, are used. In addition, in one embodiment of the present invention, a fluorine derivative can be used for a light-emitting element. In addition, in one embodiment of the present invention, a novel organic compound capable of emitting light can be provided. It is possible to provide a novel organic compound that can be used in the EL layer of the element. A novel light-emitting element with high reliability can be provided by using a novel organic compound according to one embodiment of the present invention. In addition, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. can be provided. [Brief description of the drawings]

[0035]

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Embodiments for Carrying Out the Invention

[0036] 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 its form and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not interpreted as being limited to the description of the embodiments shown below.

[0037] In addition, the position, size, range, etc. of each configuration shown in the drawings and the like may not represent the actual position, size, range, etc. for the sake of easy understanding. For this reason, the disclosed invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings and the like.

[0038] Also, in this specification and the like, when explaining the configuration of the invention using the drawings, the same reference numerals are commonly used among different drawings to indicate the same components.

[0039] (Embodiment 1) In this embodiment, an organic compound which is one aspect of the present invention will be described. Note that the ​​​The organic compound according to one embodiment is a benzofuropyrimidine derivative represented by the following general formula (G1): The organic compound according to one embodiment of the present invention is a benzothienopyrimidine derivative. As represented by the following general formula (G1), Multiple aromatic hydrocarbon rings are connected to the 8th position of the pyrimidine skeleton (specifically, 2 to 4 aromatic carbons). It has a structure in which hydrogen hydride rings are linked.

[0040] [ka]

[0041] In the general formula (G1), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 ,oh And Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. an oxy group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms; or a cyano group, and the aromatic hydrocarbon ring is formed by The number of carbon atoms is 6 to 25. In addition, m and n are each 0 or 1. A is a group having a total of 12 to 100 carbon atoms and is not a benzene ring, a naphthalene ring, a fluorene ring, heteroaromatic rings including a phenylene ring, a phenanthrene ring, a triphenylene ring, and a dibenzothiophene ring; Heteroaromatic rings containing dibenzofuran rings, heteroaromatic rings containing carbazole rings, benzimidazo It has one or more of a phenyl ring or a triphenylamine structure. 1 is hydrogen an alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted monocyclic saturated carbon atom having 5 to 7 carbon atoms; A hydrogen group, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0042] Another aspect of the present invention is an organic compound represented by the following general formula (G2). Incidentally, the organic compound represented by the following general formula (G2) has a structure in which a plurality of aromatic hydrocarbon rings are linked (specifically, 2 to 4 aromatic hydrocarbon rings are linked) at the 8-position of the benzofuropyrimidine skeleton or benzothieno[2,3-d]pyrimidine skeleton, and has a skeleton having at least hole-transporting properties at the 4-position.

[0043]

Chemical formula

[0044] In the above general formula (G2), Q represents oxygen or sulfur. Ar 1 , Ar 2 , Ar 3 , and Ar 4 represent the same group, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring . The substituent of the aromatic hydrocarbon ring is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. The number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Also, m and n are each 0 or 1. Also, α represents a substituted or unsubstituted phenylene group, and t represents an integer from 0 to 4. uni Ht 1 represents a skeleton having hole-transporting properties. Also, R 1 is hydrogen, carbon An alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms , a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms .

[0045] Another aspect of the present invention is an organic compound represented by the following general formula (G3). Incidentally The organic compound represented by the following general formula (G3) has a structure in which a plurality of aromatic hydrocarbon rings are linked (specifically, 2 to 4 aromatic hydrocarbon rings are linked) at the 8-position of the benzofuropyrimidine skeleton or benzothienopyrimidine skeleton, and has a hole-transporting skeleton via a phenylene group at the 4-position . . .

[0046]

Chemical formula

[0047] In the above general formula (G3), Q represents oxygen or sulfur. Ar 1 , Ar 2 , Ar 3 , and and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, and the substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Also, m and n are each 0 or 1. Also . Also, Ht . Also, R is hydrogen, having 1 to 6 carbon atoms . . Also uni represents a skeleton having hole-transporting properties. Also, R 1 is hydrogen, having 1 to 6 carbon atoms an alkyl group, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms is represented.

[0048] Another aspect of the present invention is an organic compound represented by the following general formula (G4). Incidentally, the organic compound represented by the following general formula (G4) has a structure in which a plurality of aromatic hydrocarbon rings are linked (specifically, 2 to 4 aromatic hydrocarbon rings are linked) to the 8-position of a benzofuropyrimidine skeleton or a benzothieno[2,3-d]pyrimidine skeleton, and has a skeleton having a hole transporting property via a biphenyldiyl group at the 4-position.

[0049]

Chemical formula

[0050] In the above general formula (G4), Q represents oxygen or sulfur. Ar 1 , Ar 2 , Ar 3 , and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, and the substituent of the aromatic hydrocarbon ring is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Also, m and n are each 0 or 1. Also , Ht uni represents a skeleton having a hole transporting property. Also, R 1 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkyl group, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms represents.

[0051] In addition, Ht in the above general formulas (G2), (G3), and (G4) uni represents a skeleton having hole transporting properties, and each independently represents any one having a pyrrole ring structure, a furan ring structure, or a thiophene ring structure. is any one of them.

[0052] In addition, Ht in the above general formulas (G2), (G3), and (G4) uni represents a skeleton having hole transporting properties, and each independently represents any one of the following general formulas (Ht-1) to (Ht-26). is any one of them.

[0053]

Chemical formula

[0054] In the above general formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. In addition, R 2 ~R 71 each represents a substituent of 1 to 4, and each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. In addition, Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0055] In addition, Ht in the above general formulas (G2), (G3), and (G4) uni represents a skeleton having hole transporting properties, It has a skeleton, and by having this skeleton, when combined with other substances (for example, a light-emitting substance) and used in a light-emitting element, the element characteristics can be improved. When combined with other substances (for example, a light-emitting substance) and used in a light-emitting element, the element characteristics can be improved.

[0056] In the general formulas (G1), (G2), (G3), and (G4), when the substituted or unsubstituted aromatic hydrocarbon ring has a substituent, the substituent is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and the like. an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, etc. a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and any one of them, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, etc. an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, etc.

[0057] In the general formulas (G1), (G2), (G3), and (G4), when the substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, the substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, the substituted or unsubstituted aryl group having 6 to 13 carbon atoms, the substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, or the substituted or unsubstituted phenylene group has a substituent, the substituent is an alkyl group having 1 to 7 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a cycloalkyl group having 5 to 7 carbon atoms such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an 8,9,10-trinorbornanyl group, an aryl group having 6 to 12 carbon atoms such as a phenyl group, a naphthyl group, a biphenyl group, etc. a pentyl group, a hexyl group, a cycloalkyl group having 5 to 7 carbon atoms such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an 8,9,10-trinorbornanyl group, etc. a tert-butyl group, a pentyl group, a hexyl group, an alkyl group having 1 to 7 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a cyclohexyl group, a cycloheptyl group, an 8,9,10-trinorbornanyl group, etc. a cyclohexyl group, a cycloheptyl group, an 8,9,10-trinorbornanyl group, an aryl group having 6 to 12 carbon atoms such as a phenyl group, a naphthyl group, a biphenyl group, etc. and the like can be mentioned.

[0058] In addition, Ar in the general formulas (G1), (G2), (G3), and (G4) 1 , Ar 2 , Ar 3 , and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring , and the substituent of the aromatic hydrocarbon ring is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. The number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. The aromatic hydrocarbon ring represents a monovalent or divalent aromatic hydrocarbon group, and specific examples where the number of carbon atoms forming it is 6 or more and 25 or less include a phenyl group, a phenylene group, a naphthyl group, a naphthylene group, a fluorenyl group, a fluorenediyl group, a spirofluorenyl group, a spirofluorenediyl group, a triphenylene group, a triphenylenediyl group, etc. However, in order not to cause an unnecessary decrease in the T1 level, it is preferable that the number of rings constituting the aromatic hydrocarbon ring is not a polyacene having 3 or more rings . In addition, it is preferable that the above-mentioned fluorenyl group and fluorenediyl group have a substituent such as an alkyl group or a phenyl group at the 9-position. In addition, Ar in the general formulas (G1), (G2), (G3), and (G4), Ar

[0059] , Ar 1 , Ar 2 , Ar 3 , and Ar 4 represents a substituted or unsubstituted aromatic hydrocarbon ring, and the substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy having 1 to 6 carbon atoms a xylyl group, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the carbon number forming the aromatic hydrocarbon ring is 6 or more and 25 or less, whereby the T1 level of the organic compound can be set to a desired value. In addition, appropriate sublimability can be maintained, and decomposition during sublimation purification or vacuum deposition can be suppressed. Furthermore, as shown in one aspect of the present invention, by connecting a plurality of the aromatic hydrocarbon rings, compared with the case where there is one aromatic hydrocarbon ring, the reliability when used in a light-emitting device can be improved. In particular, compared with the case where a substituent containing a heteroaromatic ring is introduced at the 8-position of the benzofuropyrimidine skeleton or benzothienopyrimidine skeleton, initial deterioration of the light-emitting device can be suppressed.

[0060] Also, Ar in the general formulas (G1), (G2), (G3), and (G4) 1 , Ar 2 , Ar 3 , and Ar 4 may each independently be a substituted or unsubstituted benzene ring or naphthalene ring.

[0061] Also, Ar in the general formulas (G1), (G2), (G3), and (G4) 1 , Ar 2 , Ar 3 , and Ar 4 may be the same.

[0062] Also, the following general formula (G-X), which is a partial structure in the general formulas (G1), (G2), (G3), and (G4), may be any one of the following structural formulas (G-X-p1) to (G-X-p12) and (G-X-n1) to (G-X-n6). ​​​

[0063]

Chem.

[0064]

Chem.

[0065] Further, when R in the general formulas (G1), (G2), (G3), and (G4) 1 represents a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, specific examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, a cycloheptyl group, and the like.

[0066] Further, when R in the general formulas (G1), (G2), (G3), and (G4) 1 represents a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, specific examples include a norbornyl group, an adamantyl group, a decalin group, a tricyclodecyl group, and the like.

[0067] Further, when R in the general formulas (G1), (G2), (G3), and (G4) 1 represents an aryl group having 6 to 13 carbon atoms, specific examples include a phenyl group, an o-tolyl group, an m -tolyl group, a p-tolyl group, a mesityl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, a 1-naphthyl group, a 2-naphthyl group, a fluorenyl group, and the like.

[0068] Further, when R in the general formulas (G1), (G2), (G3), and (G4) 1 represents an alkyl group having 1 to 6 carbon atoms, specific examples include a methyl group, an ethyl group, a propyl group and the like. , isopropyl group, butyl group, sec-butyl group, 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. can be mentioned.

[0069] Further, when R in the above general formulas (G1), (G2), (G3), and (G4) 1 represents a heteroaryl group having 3 to 12 carbon atoms, specific examples include triazinyl group, pyrazi nyl group, pyrimidinyl group, pyridinyl group, quinolinyl group, isoquinolinyl group, benzothie nyl group, benzofuranyl group, indolyl group, dibenzothienyl group, dibenzofuranyl group, or carbazolyl group, and the like.

[0070] Note that since R in the above general formulas (G1), (G2), (G3), and (G4) 1 is the specific example described above, the organic compound which is one aspect of the present invention has a high T1 level has. be.

[0071] Next, the specific structural formulas of the organic compounds which are one aspect of the present invention described above are shown below. However , the present invention is not limited to these.

[0072]

Chemical formula

[0073]

Chemical formula

[0074] [ka]

[0075] [ka]

[0076] The organic compounds represented by the above structural formulas (100) to (144) are represented by the above general formula (G1) However, the organic compound according to one embodiment of the present invention is not limited to this. I can't.

[0077] Next, one embodiment of the present invention is a benzofuropyrimidine derivative represented by the following general formula (G1): The present invention relates to a method for synthesizing a benzothienopyrimidine derivative.

[0078] [ka]

[0079] In the general formula (G1), Q represents oxygen or sulfur. 1 , Ar 2 , Ar 3 , and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, The substituent of the hydrogen ring is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. group, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms a cyclic hydrocarbon group, or a cyano group, Prime numbers are between 6 and 25. m and n are either 0 or 1. A is a group having a total of 12 to 100 carbon atoms and is a benzene ring, a naphthalene ring, a fluorene ring, , a complex aromatic ring containing a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a dibenzo furan ring-containing complex aromatic ring, a carbazole ring-containing complex aromatic ring, a benzimidazole ring, or a triphenylamine structure, and has any one or more thereof. Further, R 1 is hydrogen, a carbon alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms groups, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms represents.

[0080] ≪Synthesis method of the organic compound represented by the general formula (G1)≫ For the synthesis of the organic compound represented by the above general formula (G1), various reactions can be applied , for example, the organic compound represented by the general formula (G1) can be synthesized by a simple method shown in the following synthesis scheme.

[0081] As shown in the following scheme (A-1), by reacting a halogen compound (A1) containing a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton having a substituent at the 8-position with a boronic acid compound (A2) of A, an organic compound represented by the general formula (G1) can be obtained.

[0082] [Chemical formula]

[0083] In the above synthesis scheme (A-1), X represents a halogen, and Q represents oxygen or sulfur . Ar 1 , Ar 2 , Ar 3 , and Ar 4 ​​​​Each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, and the substituent of the aromatic hydrocarbon ring is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, or a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, or a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Also, m and n are each 0 or 1. Also, A is a group having 12 to 100 carbon atoms in total, and has any one or a plurality of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzo[b]thiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, and a triphenylamine structure. Also, R represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 1

[0084] Also, as shown in the following synthesis scheme (A-2), after obtaining an intermediate (B2) through a reaction of a dihalogen compound (B1) containing a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton and a boronic acid compound (A2 ) of A, by reacting with a boronic acid compound (B3), an organic compound represented by the general formula (G1) can also be obtained.

[0085]

Chemical formula

[0086] In the above synthesis scheme (A-2), Q represents oxygen or sulfur. Ar 1 , Ar 2 , Ar 3 , and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, and the substituent of the aromatic hydrocarbon ring is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Also, m and n are each 0 or 1. Also, A is a group having 12 to 100 carbon atoms in total and has any one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, and a triphenylamine structure. Also, R is hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Also, as shown in the following synthesis scheme (A-3), after obtaining an intermediate (C2) through the reaction of a trihalogen compound (C1) containing a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton with a boronic acid compound (A 2) of A, the reaction with a boronic acid compound (C3) of R , and 1 is hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Also, as shown in the following synthesis scheme (A-3), after obtaining an intermediate (C2) through the reaction of a trihalogen compound (C1) containing a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton with a boronic acid compound (A 2) of A, the reaction with a boronic acid compound (C3) of R

[0087] Also, as shown in the following synthesis scheme (A-3), through the reaction of a trihalogen compound (C1) containing a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton with a boronic acid compound (A 2) of A, after obtaining an intermediate (C2), the reaction with a boronic acid compound (C3) of R 2) of A, after obtaining an intermediate (C2), the reaction with a boronic acid compound (C3) of R 1 and After obtaining the intermediate (C4) via the response, by reacting the boronic acid compound (B3), an organic compound represented by the general formula (G1) can also be obtained.

[0088]

Chemical formula

[0089] In the above synthesis scheme (A-3), Q represents oxygen or sulfur. Ar 1 、Ar 2 、Ar 3 、and Ar 4 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the substituent of the aromatic hydrocarbon ring is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group, and the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less. Also, m and n are each 0 or 1. Also, A is a group having 12 to 100 carbon atoms in total and has any one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, and a triphenylamine structure. Also 、R 、R 1 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms 、a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Also, B 、B represents, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Also, B 1represents a boronic acid, boronic acid ester, cyclic triol borate salt, etc. Also, as the cyclic triol borate salt, potassium salt or sodium salt may be used in addition to the lithium salt.

[0090] In addition, the halogen compound (A1), boronic acid compound (A2) of A, dihalogen compound (B1) containing a benzofuropyrimidine skeleton or benzothienopyrimidine skeleton, intermediate (B2), boronic acid compound (B3), trihalogen compound (C1) containing a benzofuropyrimidine skeleton or benzothienopyrimidine skeleton, intermediate (C2), boronic acid compound (C3) of R, and intermediate (C4) used in the above synthetic schemes (A-1), (A-2), and (A-3), which contain a benzofuropyrimidine skeleton or benzothienopyrimidine skeleton having a substituent at the 8-position, are commercially available in various types or can be synthesized. Therefore, a benzofuropyrimidine derivative or benzothienopyrimidine derivative represented by the general formula (G1) can be synthesized in many types. Thus, the organic compound, which is one aspect of the present invention, is characterized by having a wide variety of variations. 1

[0091] As described above, an example of the organic compound, which is one aspect of the present invention, and its synthesis method has been described. However, the present invention is not limited thereto, and it may be synthesized using other synthesis methods.

[0092] The configuration shown in this embodiment can be used in appropriate combination with the configuration shown in other embodiments.

[0093] (Embodiment 2) In this embodiment, with reference to FIG. 1, a light-emitting device using the organic compound shown in Embodiment 1 will be described. I will explain this in more detail.

[0094] <Basic structure of light-emitting element> First, the basic structure of a light-emitting element will be described. Specifically, the first electrode 101 and the second electrode 102 are disposed in a region between the first electrode 101 and the second electrode 102. It has a structure in which an EL layer 103 is sandwiched between an electrode 102 .

[0095] In addition, in FIG. 1B, a plurality of EL layers (two layers in FIG. 1B) are disposed between a pair of electrodes. a, 103b), and a stacked structure (tandem structure) having a charge generating layer 104 between the EL layers. A light-emitting element having a tandem structure can be driven at a low voltage and consumes little power. It is possible to realize a low-energy light-emitting device.

[0096] When a voltage is applied between the first electrode 101 and the second electrode 102, the charge generating layer 104 Electrons are injected into one EL layer (103a or 103b) and the other EL layer (103b or 1B, the first electrode 1 When a voltage is applied to the charge generating layer 101 so that the potential of the charge generating layer 101 becomes higher than that of the second electrode 102, Electrons are injected from the electrode 4 into the EL layer 103a, and holes are injected into the EL layer 103b. .

[0097] The charge generating layer 104 is transparent to visible light from the viewpoint of light extraction efficiency. (Specifically, it is preferable that the transmittance of visible light through the charge generating layer 104 is 40% or more.) In addition, the charge generating layer 104 has a lower conductivity than the first electrode 101 and the second electrode 102. But it still works.

[0098] In addition, Fig. 1(C) shows an example of the case where the EL layer 103 (the EL layers (103 a, 103b) shown in Fig. 1(A)) has a stacked structure. . However, in this case, it is assumed that the first electrode 101 functions as an anode. The EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked on the first electrode 101. Also, when having a plurality of EL layers as in the tandem structure shown in Fig. 1(B), each EL layer has a structure that is sequentially stacked from the anode side as described above. Further, when the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order of the EL layers is reversed.

[0099] The light-emitting layer 113 included in the EL layers (103, 103a, 103b) has, respectively, a light-emitting substance and a plurality of substances appropriately combined to obtain fluorescence emission or phosphorescence emission presenting a desired emission color . Also, the light-emitting layer 113 may have a stacked structure with different emission colors. . In this case, the light-emitting substance and other substances used for each stacked light-emitting layer may be different materials. Further, from the plurality of EL layers (103a, 103b) shown in Fig. 1(B), a configuration in which different emission colors can be obtained may be adopted. Also in this case, the light-emitting substance and other substances used for each light-emitting layer may be different materials.

[0100] In addition, in the light-emitting element which is one aspect of the present invention, a configuration may be adopted in which the light emission obtained from the EL layers (103, 103a, 103b) is resonated between both electrodes to enhance the obtained light emission. For example, in Fig. 1(C), the first electrode 101 is a reflective electrode, and the second electrode 10 By using 2 as a semi-transmissive and semi-reflective electrode, a microcavity structure can be formed, and the light emission obtained from the EL layer 103 can be enhanced. It is possible to enhance the light emission obtained from the EL layer 103.

[0101] When the first electrode 101 of the light-emitting element is a reflective electrode composed of a laminated structure of a conductive material having reflectivity and a conductive material having translucency (transparent conductive film), optical adjustment can be performed by controlling the film thickness of the transparent conductive film. Specifically, it is preferable to adjust so that the electrode distance between the first electrode 101 and the second electrode 102 is in the vicinity of mλ / 2 (where m is a natural number) with respect to the wavelength λ of the light obtained from the light-emitting layer 113. When the first electrode 101 of the light-emitting element is a reflective electrode composed of a laminated structure of a conductive material having reflectivity and a conductive material having translucency (transparent conductive film), optical adjustment can be performed by controlling the film thickness of the transparent conductive film. Specifically, by controlling the film thickness of the transparent conductive film, optical adjustment can be performed. Specifically, with respect to the wavelength λ of the light obtained from the light-emitting layer 113, the electrode distance between the first electrode 101 and the second electrode 102 is adjusted to be in the vicinity of mλ / 2 (where m is a natural number). Specifically, with respect to the wavelength λ of the light obtained from the light-emitting layer 113, the electrode distance between the first electrode 101 and the second electrode 102 is adjusted to be in the vicinity of mλ / 2 (where m is a natural number). (However, m is a natural number).

[0102] In addition, in order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, the optical distance from the first electrode 101 to the region (light-emitting region) where the desired light of the light-emitting layer 113 is obtained, and the optical distance from the second electrode 102 to the region (light-emitting region) where the desired light of the light-emitting layer 113 is obtained are each adjusted to be in the vicinity of (2m'+1)λ / 4 (where m' is a natural number). electrode 102 to the region (light-emitting region) where the desired light of the light-emitting layer 113 is obtained are each adjusted to be in the vicinity of (2m'+1)λ / 4 (where m' is a natural number). It is preferable to adjust so that they are each in the vicinity of (2m'+1)λ / 4 (where m' is a natural number). Here, the light-emitting region refers to the recombination region of holes and electrons in the light-emitting layer 113. electrons in the light-emitting layer 113.

[0103] By performing such optical adjustment, the spectrum of a specific monochromatic light obtained from the light-emitting layer 113 can be narrowed, and light emission with good color purity can be obtained. By performing such optical adjustment, the spectrum of a specific monochromatic light obtained from the light-emitting layer 113 can be narrowed, and light emission with good color purity can be obtained.

[0104] However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 is strictly the total thickness from the reflection region in the first electrode 101 to the reflection region in the second electrode 102. It can be. However, the reflection regions in the first electrode 101 and the second electrode 102 are strictly Since it is difficult to determine the position of the first electrode 101 and the second electrode 102, It is assumed that the above-mentioned effect can be obtained by assuming the ray domain. The optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, 101 / 100 . The optical distance between the reflection area in the light emitting layer and the light emitting area in the light emitting layer from which the desired light is obtained is called the optical distance. However, it is possible to change the reflecting area of the first electrode 101 and the emitting area that can obtain the desired light. Since it is difficult to precisely determine the light-emitting region in the optical layer, the first electrode 101 may be arbitrarily selected. The position of the light source is assumed to be the reflection region, and any position on the light-emitting layer where the desired light is obtained is assumed to be the light-emitting region. It is assumed that the above-mentioned effects can be sufficiently obtained.

[0105] When the light-emitting element shown in FIG. 1C has a microcavity structure, the EL layer is common. Therefore, it is possible to obtain different emission colors. This eliminates the need for separate coloring (e.g., RGB) for the color layers, enabling high definition. It is also possible to combine it with a color filter. The emission intensity of a specific wavelength in the front direction is Since it is possible to strengthen the signal strength, it is possible to reduce power consumption.

[0106] The light-emitting element shown in FIG. 1E is an example of the light-emitting element having the tandem structure shown in FIG. 1B. As shown in the figure, three EL layers (103a, 103b, 103c) are disposed on the charge generating layer (10 The three EL layers (103a, 104a, 104b) are sandwiched between the EL layers. Each of the light-emitting layers (113a, 113b, 113c) has a light-emitting layer (113a, 113b, 113c). Therefore, the emission colors of the light emitting layers can be freely combined. The light-emitting layer 113b can be red, green, or yellow, and the light-emitting layer 113c can be blue. However, the light-emitting layer 113a can be red, the light-emitting layer 113b can be blue, green, or yellow, and the light-emitting layer 113c can be red. In the light-emitting element which is one aspect of the present invention described above, at least one of the first electrode 101 and the second electrode 102 is an electrode having translucency (such as a transparent electrode, a semi-transmissive / semi-reflective electrode, etc.).

[0107] When the translucent electrode is a transparent electrode, the transmittance of visible light of the transparent electrode is 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the reflectance of visible light of the semi-transmissive / semi-reflective electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Also, these electrodes preferably have a resistivity of 1×10 Ωcm or less. -2 -2

[0108] In the light-emitting element which is one aspect of the present invention described above, when one of the first electrode 101 and the second electrode 102 is an electrode having reflectivity (reflective electrode), the reflectance of visible light of the reflective electrode is 40% or more and 100% or less, preferably 70% or more and 100% or less. Also, this electrode preferably has a resistivity of 1×10 -2 Ωcm or less.

[0109] <<Specific Structure and Fabrication Method of Light-Emitting Element>> Next, the specific structure and fabrication method of the light-emitting element which is one aspect of the present invention and shown in FIG. 1 will be described. Here, not only the light-emitting element in which the EL layer 103 has a single-layer structure as shown in FIG. 1(A) or FIG. 1(C), but also the tandem structure light-emitting elements shown in FIG. 1(B), FIG. 1(D), and FIG. 1(E) will be described together. Each light-emitting element shown in FIG. 1 is a micro structure light-emitting element. ​When having a cavity structure, for example, the first electrode 101 can be formed as a reflective electrode, and the second electrode 102 can be formed as a semi-transmissive and semi-reflective electrode. Also, a desired electrode material can be used singly or in plurality, and can be formed in a single layer or by lamination. Further, the second electrode 102 is , after forming the EL layer (103, 103b), the material is selected and formed in the same manner as above. Also , for the fabrication of these electrodes, a sputtering method or a vacuum evaporation method can be used.

[0110] <The first electrode and the second electrode> As materials for forming the first electrode 101 and the second electrode 102, the following materials can be appropriately combined and used as long as the functions of the above-mentioned both electrodes can be satisfied. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be appropriately used. Specifically, indium-tin oxide (also referred to as ITO), indium-silicon-tin oxide (also referred to as ITSO), indium-zinc oxide, indium-tungsten-zinc oxide can be mentioned. In addition, aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd) and other metals, and alloys containing these appropriately combined can also be used. In addition, elements belonging to Group 1 or Group 2 of the periodic table not exemplified above (for example, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), rare earth metals such as europium (Eu), ytterbium (Yb), and ​​​​ An alloy containing these in appropriate combination, or others such as graphene can be used.

[0111] In the light-emitting element shown in FIG. 1, having an EL layer 103 with a laminated structure as shown in FIG. 1(C) , when the first electrode 101 is an anode, a hole injection layer 111 and a hole transport layer 112 of the EL layer 103 are sequentially laminated and formed on the first electrode 101 by a vacuum evaporation method. Further, as shown in FIG. 1(D) , a plurality of EL layers (103a, 103b) having a laminated structure are laminated with a charge generation layer 104 interposed therebetween. When the first electrode 101 is an anode, a hole injection layer 111a and a hole transport layer 112a of the EL layer 103a are sequentially laminated and formed on the first electrode 101 by a vacuum evaporation method. Not only that, after the EL layer 103a and the charge generation layer 104 are sequentially laminated and formed, a hole injection layer 111b and a hole transport layer 112b of the EL layer 103b are similarly sequentially laminated and formed on the charge generation layer 10 4.

[0112] <Hole injection layer and hole transport layer> The hole injection layers (111, 111a, 111b) are layers that inject holes from the first electrode 101, which is an anode, or the charge generation layer (104) into the EL layer (103, 103a, 103b), and are layers containing a material with high hole injection property.

[0113] Examples of materials with high hole injection 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: H2Pc) and copper phthalocyanine (abbreviation: CuPC) can be used.

[0114] In addition, aromatic amine compounds such as 4,4’,4’’-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4’,4’’-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4’-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc., which are low molecular weight compounds, can be used. 4,4’,4’’-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4 ’-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4 ’-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’ -phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD) 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)- N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6- bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9- phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCz PCN1), etc., which are aromatic amine compounds, can be used. etc., can be used.

[0115] In addition, polymeric compounds (oligomers, dendrimers, polymers, etc.) such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: P VTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine (Abbreviation: Poly-TPD) etc. can be used. Or, poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS), a polymer compound to which an acid such as polyaniline / poly(styrenesulfonic acid) (PAni / PSS) is added, etc. can also be used.

[0116] In addition, as a material with high hole injection property, a composite material containing a hole transporting material and an acceptor material (electron accepting material) can also be used. In this case, electrons are withdrawn from the hole transporting material by the acceptor material, and holes are generated in the hole injection layer (111, 111a, 111b), and the holes are injected into the light emitting layer (113, 113a, 113b) through the hole transporting layer (112, 112a, 112b). Note that the hole injection layer (111, 111a, 111b) may be formed of a single layer made of a composite material containing a hole transporting material and an acceptor material (electron accepting material), or may be formed by laminating the hole transporting material and the acceptor material (electron accepting material) in separate layers.

[0117] The hole transporting layer (112, 112a, 112b) is a layer that transports the holes injected from the first electrode 101 to the light emitting layer (113, 113a, 113b) by the hole injection layer (111, 111a, 111b). Note that the hole transporting layer (112, 112a, 112b) is a layer containing a hole transporting material. The hole transporting material used for the hole transporting layer (112, 112a, 112b) preferably has a HOMO level that is the same as or close to the HOMO level of the hole injection layer (111, 111a, 111b).

[0118] As the acceptor material used for the positive hole injection layer (111, 111a, 111b), elements Oxides of metals belonging to Groups 4 to 8 in the periodic table can be used. Specifically are molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, t ungsten oxide, manganese oxide, and rhenium oxide. Among them, molybdenum oxide is preferred because it is stable even in the atmosphere, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used. Examples of those having an electron-withdrawing group (halogen group or cyano group) include 7, 7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4 -TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5, 8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7 ,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), etc. In particular, a compound in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of heteroatoms like HAT-CN is thermally stable and preferred. Also, [3]radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) are preferred because they have extremely high electron accepting properties. Specifically, α,α’,α’’-1,2,3-cycloprop antriylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacet tonitrile], α,α’,α’’-1,2,3-cyclopropantriylidene tris[2 ,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonit ril], α,α’,α’’-1,2,3-cyclopropantriylidene tris[2,3, Examples include 4,5,6-pentafluorobenzeneacetonitrile and the like.

[0119] As the hole transporting material used for the hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 11 2b), a substance having a hole mobility of 10 -6 cm 2 / Vs or more is preferable. In addition, as long as the substance has higher hole transportability than electrons, other substances can be used. As the hole transporting material, hole transporting materials with high hole transportability such as π-electron excess type heteroaromatic compounds (for example, carbazole derivatives, furan derivatives, and thiophene derivatives) and aromatic amines (compounds having an aromatic amine skeleton) are preferable.

[0120] As the above-mentioned carbazole derivative (compound having a carbazole skeleton), bicarba zole derivatives (for example, 3,3'-bicarba zole derivatives), aromatic amines having a carbazolyl group, etc. can be mentioned.

[0121] In addition, as the bicarba zole derivative (for example, 3,3'-bicarba zole derivative), specifically, 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP),

[0122] 9,9'-bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carbazole, 9,9'-bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole, 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4 -yl)-9H,9'H-3,3'-bicarba zole (abbreviation: mBPCCBP), 9-( 2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarba zole (abbreviation: β Examples include NCCP).

[0123] In addition, specific examples of the aromatic amine having a carbazolyl group include 4-phenyl-4' -(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCB A1BP), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2 -yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N- (1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol -3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: P CBBiF), 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: PC BANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbaz -ol-3-yl)triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl -(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N ,N'-bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene -1,3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N' ,N''-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-tri amine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phe nyl-9H-carbazol-3-yl)phenyl]fluorene-2-amine (abbreviation: PC BAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl) phenyl]spiro-9,9'-bifluorene-2-amine (abbreviation: PCBASF), 3- [N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenyl carbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol yl-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPC A2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)a mino]-9-phenylcarbazole (abbreviation: PCzPCN1), 3-[N-(4-diphe nylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PC zDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenyla mino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4 -diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazo le (abbreviation: PCzTPN2), 2-[N-(9-phenylcarbazol-3-yl)- N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4 -(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylanili ne (abbreviation: YGA1BP), N,N'-bis[4-(carbazol-9-yl)phenyl -N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: Y GA2F), 4,4',4''-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA) and the like can be mentioned.

[0124] In addition to the above, as carbazole derivatives, 3-[4-(9-phenanthryl)-phen Nile]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3-[4-(1-na phthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 1,3 -bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4’-di(N-carbazol yl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9- phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazol yl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anth racenyl)phenyl]-9H-carbazole (abbreviation: CzPA), etc. can be mentioned.

[0125] Regarding the above, as the thiophene derivative and furan derivative, specifically, 1,3,5-tri( dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II), 2,8-diphe nyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothio phene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluore ne-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-I V), etc. compounds having a thiophene skeleton, 4,4’,4’’-(benzene-1,3,5 -triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-( 9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbre viation: mmDBFFLBi-II), etc. compounds having a furan skeleton, etc. can be mentioned.

[0126] Regarding the above, as the aromatic amine, specifically, 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'-di amine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene-2 -yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'- (9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4 -phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9 ,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren -2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLA DFL), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl l)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl )-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 2, 7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9, 9'-bifluorene (abbreviation: DPA2SF), 4,4',4''-tris[N-(1-na phthyl)-N-phenylamino]triphenylamine (abbreviation: 1-TNATA), 4,4 ',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDAT A), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino] triphenylamine (abbreviation: m-MTDATA), N,N'-di(p-tolyl)-N,N '-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N -(4-Diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPA) B), 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), etc. may be mentioned.

[0127] As the hole transporting material, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4 -vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4- (4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)metha crylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl) -N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), etc. of polymerized compounds can also be used.

[0128] However, the hole transporting material is not limited to the above, and various known materials can be used alone or in combination of one or more species as the hole transporting material for the hole injection layer (111, 111a, 111b) and the positive hole transport layer (112, 112a, 112b). Note that the hole transport layer (1 12, 112a, 112b) may be formed of a plurality of layers respectively. That is, for example the first hole transport layer and the second hole transport layer may be laminated.

[0129] In the light emitting device shown in FIG. 1, the light emitting layer (113, 11 2a) is formed on the hole transport layer (112, 11 In the case of the light-emitting element having a tandem structure shown in After the EL layer 103a and the charge generation layer 104 are formed, the light-emitting layer 113b is also formed on the hole transport layer 112b of the EL layer 103b by the vacuum deposition method.

[0130] <Light-emitting layer> The light-emitting layer (113, 113a, 113b, 113c) is a layer containing a light-emitting substance. Note that As the light-emitting substance, substances exhibiting light-emitting colors such as blue, purple, blue-violet, green, yellow-green, yellow, orange, and red are appropriately used. Also, by using different light-emitting substances in the plurality of light-emitting layers (113a, 113b, 113c), a configuration that exhibits different light-emitting colors (for example, white light emission obtained by combining light-emitting colors in a complementary color relationship) can be achieved. Furthermore, one light-emitting layer may have a laminated structure having different light-emitting substances.

[0131] Also, the light-emitting layer (113, 113a, 113b, 113c) may have one or more kinds of organic compounds (such as host materials) in addition to the light-emitting substance (guest material). Also, as one or more kinds of organic compounds, the organic compounds that are one aspect of the present invention, or one or both of the hole-transporting material and the electron-transporting material described in this embodiment can be used.

[0132]

[0133]

[0134] There is no particular limitation on the light-emitting substance that can be used in the light-emitting layer (113, 113a, 113b, 113c), and a light-emitting substance that converts singlet excitation energy into light emission in the visible light region, or a light-emitting substance that converts triplet excitation energy into light emission in the visible light region can be used.

[0133] In addition, examples of other light-emitting substances include the following.

[0134] As a luminescent substance that converts singlet excitation energy into luminescence, a substance that emits fluorescence (fluorescent material) can be mentioned. For example, pyrene derivatives, anthracene derivatives, triphenylene derivatives, flu orene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives , phenanthrene derivatives, naphthalene derivatives, etc. can be mentioned. In particular, pyrene derivatives are preferred because they have a high fluorescence quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3- methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bi s(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation : 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N,N '-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-( pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]fura n)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-di yl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis (6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation : 1,6BnfAPrn-03), etc. can be mentioned. ​

[0135] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2, 2’-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4’-(10-phenyl- 9-anthryl)biphenyl-4-yl]-2,2’-bipyridine (abbreviation: PAPP2B Py), N,N’-bis[4-(9H-carbazol-9-yl)phenyl]-N,N’ -diphenylstilbene-4,4’-diamine (abbreviation: YGA2S), 4-(9H-carb azol-9-yl)-4’-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4’-(9,10-di phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-di phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbaz ol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4 ’-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4’-(9- phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA ), perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP) , N,N’’-(2-tert-butylanthracene-9,10-diyl-di-4,1-f enylene)bis[N,N’,N’-triphenyl-1,4-phenylenediamine] (abbreviation : DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anth ryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N- [4-(9,10-Diphenyl-2-anthryl)phenyl]-N,N’,N’-tri enyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) etc. can be used. .

[0136] In addition, as a luminescent substance that converts triplet excitation energy into luminescence, for example, substances that emit phosphorescence (phosphorescent materials) and thermally activated delayed fluorescence (Thermally ac tivated delayed fluorescence: TADF) materials that exhibit thermally activated delayed fluorescence can be mentioned. .

[0137] Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), rare earth metal complexes, etc. Since these exhibit different emission colors (emission peaks) for each substance, they are appropriately selected and used as needed.

[0138] Examples of phosphorescent materials that exhibit blue or green and have a peak wavelength of the emission spectrum of 450 nm or more and 570 nm or less include the following substances.

[0139] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN 2 phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl yl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrp tz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl bis[3- methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl -5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III I) (abbreviation: [Ir(Prptz1-Me)3]) and other organometallic complexes having a 1H-triazole skeleton, fac-tris[1-(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: [Ir(dmpimpt-Me)3 ), and other organometallic complexes having an imidazole skeleton, bis[2-(4’,6’-difluoro phenyl)pyridinato-N,C 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 }iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) and bis[2-(4’,6’-difluorophenyl)pyridinato-N,C 2’ iridium (III) acetylacetonate (abbreviation: FIr(acac)) having an electron-withdrawing group 2’ as well as 2’ (III) ​​​Examples of the organometallic complex using a phenylpyridine derivative as a ligand include the like.

[0140] Exhibiting green or yellow, with the peak wavelength of the emission spectrum being 495 nm or more and 590 nm or less Examples of the phosphorescent material include the following substances.

[0141] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation : [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)i ridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bi s(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(m ppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(a cac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl pyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]) , (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-pheni lpyrymidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac) ), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethyl phenyl)-4-pyrimidinyl-κN 3 phenyl-κC}iridium(III) (abbreviation : [Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2( acac)]) and other organometallic iridium complexes having a pyrimidine skeleton, (acetylaceta Setonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III)( Abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5 -isopropyl-3-methyl-2-phenylpyrazinato)iridium(III)(Abbreviation: [Ir(mppr-iPr)2(acac)]) and other organometallic iridium complexes having a pyrazine skeleton, tris(2-phenylpyridinato-N,C )iridium(III) 2’ ) (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: [I r(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(II I)(Abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) iridium(III)(Abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato- N,C 2’ )iridium(III) acetylacetonate(Abbreviation: [Ir(pq)2(a cac)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-phe nyl-2-pyridinyl-κN)phenyl-κC]iridium(III)(Abbreviation: [Ir( ppy)2(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC] [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC] and other organometallic iridium complexes having a pyridine skeleton, bis(2,4-diphenyl-1,3-ox oxazolato-N,C 2’ )iridium(III) acetylacetonate(Abbreviation: [Ir( dpo)2(acac)])、bis{2-[4’-(perfluorophenyl)phenyl] pyridinato-N,C 2’}iridium(III) acetylacetonate (abbreviation: [Ir( p-PF-ph)2(acac)])、bis(2-phenylbenzothiazolato-N,C 2 ’ )iridium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac) ) and other organometallic complexes, tris(acetylacetonato)(monophenanthroline) terbium(III) (abbreviation: [Tb(acac)3(Phen)]) and other rare earth metal complexes.

[0142] Exhibiting yellow or red color, and having a peak wavelength of the emission spectrum in the range of 570 nm or more and 750 nm or less Examples of the phosphorescent material include the following substances.

[0143] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimi dinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bi s[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iri dium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (dipivaloylmeth anato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III )(abbreviation: [Ir(d1npm)2(dpm)]) and other organometallic complexes having a pyrimidine skeleton, (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iri dium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-t riphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir (tppr)2(dpm)]) (tppr)2(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethyl phenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dime thyl-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-pyraz inyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedio nato-κ 2 O,O’)iridium(III) (abbreviation: [Ir(dmdppr-dmCP) 2(dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxali nato-N,C 2’ iridium(III) (abbreviation: [Ir(mpq)2(acac)]) , (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C 2’ )ir dium(III) (abbreviation: [Ir(dpq)2(acac)]), (acetylacetonato )bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]) and other organometallic complexes having a pyrazine skeleton, tris(1-phenylisoquinolinato-N,C 2’ )iridium(III) (abbre viation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ )ir dium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), bi s[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pen tanedionato-κ 2Organic compounds having a pyridine skeleton such as iridium(III) (O,O’) metal complexes, platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H- porphyrin platinum(II) (abbreviation: [PtOEP]), tris(1,3 -diphenyl-1,3-propanedionato)(monophenanthroline) europium(I II) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-thenoyl)- 3,3,3-trifluoroacetonato](monophenanthroline)europium(III )(abbreviation: [Eu(TTA)3(Phen)]) and other rare earth metal complexes.

[0144] As the organic compound (host material, etc.) used in the light-emitting layer (113, 113a, 113b, 113c), a substance having an energy gap larger than the energy gap of the light-emitting substance (guest material) may be selected and used singly or in combination of two or more.

[0145] Therefore, when the light-emitting substance used in the light-emitting layer (113, 113a, 113b, 113c) is a fluorescent material it is preferable to use an organic compound having a large energy level of the singlet excited state and a small energy level of the triplet excited state as the organic compound (host material) used in combination with the light-emitting substance. In addition, as the organic compound (host material) used in combination with the light-emitting substance, in addition to the hole-transporting material (described above) and the electron-transporting material (described later) shown in this embodiment bipolar materials and the like can be used.

[0146] Although partially overlapping with the above specific examples, specific examples of organic compounds are shown below

[0147]

[0147] When the luminescent substance is a fluorescent material, an organic compound that can be used in combination with the luminescent substance (host material) includes condensed polycyclic aromatic compounds such as anthracene derivatives, tetracene derivatives, phenanthrene derivatives body, pyrene derivatives, chrysene derivatives, dibenzo[g,p]chrysene derivatives, etc. Aromatic compounds are mentioned.

[0148] In addition, as specific examples of the organic compound (host material) used in combination with the fluorescent luminescent substance is 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H- carbazole (abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl -9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 3-[4 -(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN ), 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl- 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3- amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenyl amine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4 -[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole -3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl )-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), 6 ,12-dimethoxy-5,11-diphenylchrysene, N,N,N’,N’,N’’,N ’’,N’’’,N’’’-octaphenyldibenzog,p]chrysene-2,7,10 ,15 - Tetraamine (abbreviation: DBC1), 9 - [4 - (10 - phenyl - 9 - anthra cenyl)phenyl] - 9H - carbazole (abbreviation: CzPA), 7 - [4 - (10 - phe nyl - 9 - anthryl)phenyl] - 7H - dibenzo[c,g]carbazole (abbreviation: c gDBCzPA), 6 - [3 - (9,10 - diphenyl - 2 - anthryl)phenyl] - benzo[b]naphtho[1,2 - d]furan (abbreviation: 2mBnfPPA), 9 - phenyl - 10 - {4 - (9 - phenyl - 9H - fluoren - 9 - yl) - biphenyl - 4’ - yl } - anthracene (abbreviation: FLPPA), 9,10 - bis(3,5 - diphenylphenyl )anthracene (abbreviation: DPPA), 9,10 - di(2 - naphthyl)anthracene (abbreviation : DNA), 2 - tert - butyl - 9,10 - di(2 - naphthyl)anthracene (abbreviation : t - BuDNA), 9,9’ - bianthryl (abbreviation: BANT), 9,9’ - (stil bene - 3,3’ - diyl)diphenanthrene (abbreviation: DPNS), 9,9’ - (stilbene ne - 4,4’ - diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5 - tri(1 - pyrenyl)benzene (abbreviation: TPB3), 5,12 - diphenyltetracene, 5,12 - bis(biphenyl - 2 - yl)tetracene and the like can be mentioned.

[0149] Also, when the light - emitting substance is a phosphorescent material, as the organic compound (host material) used in combination with the light - emitting substance, an organic compound having a triplet excitation energy larger than the triplet excitation energy (energy difference between the ground state and the triplet excited state) of the light - emitting substance may be selected. Note that in order to form an exciplex, a plurality of organic compounds (for example, the first host material and the second host material) When using a host material (or assist material, etc.) in combination with a luminescent substance, these plural organic compounds are preferably used by mixing with a phosphorescent material.

[0150] With such a configuration, Ex TET (Exciplex-Triplet Energy Transfer), which is energy transfer from an exciplex to a luminescent substance, is used to efficiently obtain luminescence. Note that as a combination of plural organic compounds, those in which an exciplex is easily formed are preferable, and it is particularly preferable to combine a compound (hole transport material) that easily receives holes with a compound (electron transport material) that easily receives electrons. Note that the organic compound, which is one aspect of the present invention shown in Embodiment 1, is suitable as a host material when the luminescent substance is a phosphorescent material because its triplet excited state is stable. In particular, it is suitable when used in combination with a phosphorescent material that exhibits green luminescence from its triplet excitation energy level. Suitable.

[0151] Note that as organic compounds (host materials, assist materials) that can be used in combination with a luminescent substance when the luminescent substance is a phosphorescent material, aromatic amines, carbazole derivatives, dibenzo thiophene derivatives, dibenzofuran derivatives, zinc- or aluminum-based metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline derivatives, etc. can be mentioned. Among the above, aromatic amines (aromatic amine skeletons

[0152] which are organic compounds with high hole transport properties Specific examples of the compound having [the relevant property] are the same as the specific examples of the hole transporting material shown above. include.

[0153] In addition, specific examples of the carbazole derivative, which is an organic compound with high hole transportability, are the same as the specific examples of the hole transporting material shown above. include.

[0154] In addition, specific examples of the dibenzothiophene derivative and dibenzofuran derivative, which are organic compounds with high hole transportability, include 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: DB F3P-II), 1,3,5-tri(dibenzothiophen-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-phenyldibenz thiophene (abbreviation: DBTFLP-IV), 4-[3-(triphenylene-2-yl)ph enyl]dibenzothiophene (abbreviation: mDBTPTp-II), etc. include. include.

[0155] In addition, specific examples of the zinc or aluminum-based metal complex, which is an organic compound with high electron transportability, include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis (10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2) , bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(I II) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), etc., and metal complexes having a quinoline skeleton or a benzoquinoline skeleton can be mentioned. In addition, metal complexes having oxazole-based or thiazole-based ligands such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: Zn

[0156] PBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: Zn BTZ) can also be used. In addition, specific examples of oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, and phenanthroline derivatives, which are organic compounds with high electron transport properties, include 2-(4-biphenylyl)-5-(4-ter t-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis

[0157] [5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiaz ol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-bip enylyl)-5-(4-tert-butylphenyl)-4-phenyl-1,2,4-tri azole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetriyl)tri s(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(diben zothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation ​​​​Name: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazole-2-isocyanate) stilbene (abbreviation: BzOS), bathophenanthroline (abbreviation: Bphen), Cuproin (abbreviation: BCP), 2,9-bis(naphthalene-2-yl)-4,7-difluoro Phenyl-1,10-phenanthroline (abbreviation: NBphen), 2-[3-(dibenzothiophene 2mDibenzo[f,h]quinoxaline (abbreviation: 2mDBTP DBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl ]Dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3' -(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinox Sarin (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carba 2CzPDBq -III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h ]quinoxaline (abbreviation: 7mDBTPDBq-II) and 6-[3-(dibenzothiophene 6m-4-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDB q-II).

[0158] In addition, heterocyclic compounds having a diazine skeleton, triazine, and tetraazine, which are organic compounds with high electron transport properties, Specific examples of heterocyclic compounds having a benzene skeleton and heterocyclic compounds having a pyridine skeleton include: 4,6-Bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6 mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (Abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole- 9-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-9H-carbazole (abbreviation: 4,6mCzP2Pm), 2-{4-[3-( N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9 -[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-9'- phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35 DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), etc. can be mentioned.

[0159] In addition, as an organic compound with high electron transport properties, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine -3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene -2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: P F-BPy) and other polymer compounds can also be used.

[0160] In addition, when a plurality of organic compounds are used in the light-emitting layer (113, 113a, 113b, 113c), two types of compounds (the first compound and the second compound) that form an exciplex, and an organometallic complex may be mixed and used. In this case, various organic compounds can be used in appropriate combinations, but in order to efficiently form an exciplex, a compound that easily accepts holes ( hole transport material) and a compound that easily accepts electrons (electron transport material) are combined. ​This is particularly preferable. Specific examples of the hole transporting material and the electron transporting material can be the materials shown in this embodiment. With this configuration, high efficiency, low voltage, and long life can be achieved simultaneously. This is particularly preferable. Specific examples of the hole transporting material and the electron transporting material can be the materials shown in this embodiment. With this configuration, high efficiency, low voltage, and long life can be achieved simultaneously. This is particularly preferable. Specific examples of the hole transporting material and the electron transporting material can be the materials shown in this embodiment. With this configuration, high efficiency, low voltage, and long life can be achieved simultaneously.

[0161] A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10 A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10 A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10 A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10 A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10 A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10 A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10 -6 A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10 -3 A TADF material is a material in which triplet excited states can be up-converted (intersystem crossing) to singlet excited states by slight thermal energy and can efficiently exhibit luminescence (fluorescence) from singlet excited states. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Also, the delayed fluorescence in a TADF material refers to luminescence that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. That lifetime is 10

[0162] Examples of the TADF material include fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be mentioned. Examples of the metal-containing porphyrin include Examples of the TADF material include fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be mentioned. Examples of the metal-containing porphyrin include Examples of the TADF material include fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be mentioned. Examples of the metal-containing porphyrin include Examples of the TADF material include fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be mentioned. Examples of the metal-containing porphyrin include Examples of the TADF material include fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be mentioned. Examples of the metal-containing porphyrin include Examples of the TADF material include fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be mentioned. Examples of the metal-containing porphyrin include Examples of the TADF material include fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be mentioned. Examples of the metal-containing porphyrin include Examples of the TADF material include fullerenes and their derivatives, acridine derivatives such as proflavine, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be mentioned. Examples of the metal-containing porphyrin include 4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(OEP)) , etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), octaethyl porphyrin-platinum chloride complex (abbreviation: PtCl2OEP), and the like.

[0163] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo [2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-T RZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-c arbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-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-di methyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACR XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10’H-spiro[a cridine-9,9’-anthracene]-10’-one (abbreviation: ACRSA), and the like. Heterocyclic compounds having a π-electron excess type heteroaromatic ring and a π-electron deficient type heteroaromatic ring can be used. Note that a substance in which a π-electron excess type heteroaromatic ring and a π-electron deficient type heteroaromatic ring are directly bonded has both strong donor properties of the π-electron excess type heteroaromatic ring and acceptor properties of the π-electron deficient type heteroaromatic ring. and the energy difference between the singlet excited state and the triplet excited state becomes small, which is particularly preferable. Yes.

[0164] In addition, when using a TADF material, it can also be used in combination with other organic compounds. In particular, it can be combined with the host material, hole transport material, and electron transport material described above, and the organic compound which is one aspect of the present invention shown in Embodiment 1 is preferably used as the host material for the TADF material. Yes.

[0165] In addition, the above materials can be used to form the light-emitting layer (113, 113a, 113b, 113c) by combining with low molecular weight materials or high molecular weight materials. For film formation, known methods (such as vapor deposition method, coating method, printing method, etc.) can be appropriately used.

[0166] In the light-emitting element shown in FIG. 1, an electron transport layer (114, 114a) is formed on the light-emitting layer (113, 113a) of the EL layer (103, 103a). In the case of the light-emitting element having a tandem structure shown in FIG. 1(D), after the EL layer 103a and the charge generation layer 104 are formed, an electron transport layer 114b is also formed on the light-emitting layer 113b of the EL layer 103b.

[0167] <Electron transport layer> The electron transport layer (114, 114a, 114b) is a layer that transports electrons injected from the second electrode 102 to the light-emitting layer (113, 113a, 113b) by the electron injection layer (115, 115a, 115b). The electron transport layer (114, 114a, 114b) is a layer containing an electron transport material. The electron transport material used for the electron transport layer (114, 114a, 114b) is 1×10 cm -6 -6 cm 2A substance having an electron mobility of Vs or higher is preferable. Note that substances having higher electron transportability than holes can be used other than these . Further, the organic compound which is one aspect of the present invention shown in Embodiment 1 is excellent in electron transportability and thus can also be used as an electron transport layer.

[0168] As the electron transport material, a metal complex having a quinoline skeleton, a metal complex having a benzoquinoline skeleton, a metal complex having an oxazole skeleton, a metal complex having a thiazole skeleton, etc., in addition, an oxadiazole derivative, a triazole derivative, an imidazole derivative, an oxazole derivative, a thiazole derivative, a phenanthroline derivative, a quinoline derivative having a quinoline ligand, a benzoquinoline derivative, a quinoxaline derivative, a dibenzoquinoxaline derivative, a pyridine derivative, a bipyridine derivative, a pyrimidine derivative, and other electron transport materials such as π-electron deficient heteroaromatic compounds containing nitrogen-containing heteroaromatic compounds can be used.

[0169] Specific examples of the electron transport material include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq3), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (II)(abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II)(abbreviation: Znq) and other metal complexes having a quinoline skeleton or a benzoquinoline skeleton , bis[2-(2-benzoxazolyl)phenolato]zinc(II)(abbreviation: ZnPBO ) Zinc(II) bis[2-(2-benzothiazolyl)phenolato] (abbreviation: ZnBTZ ) Zinc(II) bis[2-(2-hydroxyphenyl)benzothiazolato] (abbreviation: Z n(BTZ)2), and other metal complexes having an oxazole skeleton or a thiazole skeleton, etc. can be mentioned among them.

[0170] In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl )-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-te rt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl) phenyl]-9H-carbazole (abbreviation: CO11), and other oxadiazole derivatives, 3- (4-biphenylyl)-5-(4-tert-butylphenyl)-4-phenyl-1,2 ,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-( 4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), and other triazole derivatives, 2,2’,2’’-(1,3,5-benzene triyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2 -[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzo imidazole (abbreviation: mDBTBIm-II), and other imidazole derivatives (including benzimidazole derivatives), 4,4’-bis(5-methylbenzoxazol-2-yl)sty rubene (abbreviation: BzOS), and other oxazole derivatives, bathophenanthroline (abbreviation: B phen), bathocuproine (abbreviation: BCP), 2,9-bis(naphthalen-2-yl ) - Phenanthroline derivatives such as 4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo [f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3’-(dibenzo thiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3’-(9H-carbazol-9-yl)bi phenyl-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-(dibenzothio phen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPD Bq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo [f,h]quinoxaline (abbreviation: 6mDBTPDBq-II) and other quinoxaline derivatives, or dibenzoquinoxaline derivatives, 3,5-bis[3-(9H-carbazol-9-yl phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-py ridyl)phenyl]benzene (abbreviation: TmPyPB) and other pyridine derivatives, 4,6-bis [3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2P m), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4, 6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)f enyl]pyrimidine (abbreviation: 4,6mCzP2Pm) and other pyrimidine derivatives, 2-{4- [3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl {[Ru]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTz n), etc. can be used as triazine derivatives.

[0171] Also, polymers such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl fluorene-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) can also be used.

[0172] Also, the electron transport layer (114, 114a, 114b) may not only be a single layer, but also have a structure in which two or more layers composed of the above substances are stacked.

[0173] Next, in the light-emitting element shown in Fig. 1(D), an electron injection layer 115a is formed on the electron transport layer 114a of the EL layer 103a by vacuum evaporation. Then, the EL layer 103a and the charge generation layer 104 are formed, and after forming up to the electron transport layer 114b of the EL layer 103b, an electron injection layer 115b is formed on it by vacuum evaporation.

[0174] <Electron injection layer> The electron injection layer (115, 115a, 115b) is a layer containing a substance with high electron injection property. For the electron injection layer (115, 115a, 115b), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiO ) and other such alkali metals, alkaline earth metals, or their compounds can be used. Also, x In addition, rare earth metal compounds such as erbium fluoride (ErF3) can be used. Also, an electride may be used for the electron injection layers (115, 115a, 115b). Examples of electrides include substances obtained by adding electrons to a mixed oxide of calcium and aluminum at a high concentration. Note that the materials constituting the above-described electron transport layers (114, 114a, 114b) can also be used.

[0175] Further, a composite material formed by mixing an organic compound and an electron donor may be used for the electron injection layers (115, 115a, 115b). Since electrons are generated in the organic compound by the electron donor, such a composite material is excellent in electron injection properties and electron transport properties. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, the electron transport materials (metal complexes, heteroaromatic compounds, etc.) used for the above-described electron transport layers (114, 114a, 114b) can be used. As the electron donor, any substance that exhibits electron-donating properties with respect to the organic compound may be used. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Also, alkali metal oxides and alkaline earth metal oxides are

[0176] preferred, and examples include lithium oxide, calcium oxide, barium oxide, etc. In such a case, it is preferable that the optical distance between the second electrode 102 and the light-emitting layer 113b is formed to be less than 1 / 4 of the wavelength λ of the light emitted by the light-emitting layer 113b. In this case, it can be adjusted by changing the film thickness of the electron transport layer 114b or the electron injection layer 115b.

[0177] <Charge generation layer> In the light-emitting element shown in Fig. 1(D), when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102, the charge generation layer 104 has a function of injecting electrons into the EL layer 103a and injecting holes into the EL layer 103b. Note that the charge generation layer 104 may have a structure in which an electron acceptor is added to a hole-transporting material, or a structure in which an electron donor is added to an electron-transporting material. Further, both of these structures may be laminated. By forming the charge generation layer 104 using the above-described materials, it is possible to suppress an increase in the driving voltage when the EL layers are laminated.

[0178] When the charge generation layer 104 has a structure in which an electron acceptor is added to a hole-transporting material, as the hole-transporting material, the materials shown in this embodiment can be used. As the electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, etc. can be mentioned. Further, metal oxides belonging to Groups 4 to 8 in the periodic table of elements can be mentioned. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, etc. can be mentioned.

[0179] ​​​​​​​​​​​​​​In the case where an electron donor is added to the electron transporting material in the charge generation layer 104, As the electron transporting material, the materials shown in this embodiment can be used. Also, for the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, or a metal belonging to Groups 2 and 13 in the periodic table and its oxides and carbonates 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, etc. Also, an organic compound such as tetrathianaphthacene may be used as the electron donor.

[0180] Note that the EL layer 103c in Fig. 1(E) may have the same configuration as the above-described EL layers (103, 103a, 103b). Also, the charge generation layers 104a and 104b may have the same configuration as the above-described charge generation layer 104.

[0181] <Substrate> The light-emitting element shown in this embodiment can be formed on various substrates. Note that the type of substrate is not limited to a specific one. As an example of the substrate, a semiconductor substrate (e.g., 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 tantalum substrate, a substrate having a tungsten foil, a flexible substrate, a laminated film, paper containing a fibrous material, or a base film, etc. can be mentioned.

[0182] Note that as an example of the glass substrate, barium borosilicate glass, aluminoborosilicate glass Examples include quartz, or soda lime glass. Further, examples of the flexible substrate, the bonding film, , and the base film include synthetic resins such as polyethylene terephthalate (PET), polyeth ylene naphthalate (PEN), and polyethersulfone (PES), plastics typified by acrylic resins, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic vapor deposition film, or papers, and the like.

[0183] Note that, for the fabrication of the light-emitting element shown in this embodiment, vacuum processes such as vapor deposition methods and solution processes such as spin co ating methods and inkjet methods can be used. In the case of using a vapor deposition method, physical vapor deposition methods (PVD methods) such as sputtering methods, ion plating methods, ion beam vapor deposition methods, molecular beam vapor deposition methods, and vacuum vapor deposition methods, or chemical vapor deposition methods (CVD methods) and the like can be used. Particularly, for the functional layers (hole injection layers (111, 111a, 111 b), hole transport layers (112, 112a, 112b), light-emitting layers (113, 113a, 113 b, 113c), electron transport layers (114, 114a, 114b), electron injection layers (115, 1 15a, 115b)), and charge generation layers (104, 104a, 104b)) included in the EL layer of the light-emitting element, they can be formed by methods such as vapor deposition methods (such as vacuum vapor deposition methods), coating methods (dip coating methods, die coating methods, bar coating methods, spin coating methods, spray coating methods, etc.), printing methods (inkjet methods, screen (stencil printing) methods, offset (lithographic printing) methods, flexo (letterpress printing) methods, gravure methods, microcontact printing methods, nanoimprint methods, etc.).

[0184] ​​Note that the EL layers (103, 103a, 103b) of the light-emitting element shown in this embodiment are configured by each functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a , 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport layer (114 , 114a, 114b), electron injection layer (115, 115a, 115b)) or charge generation layer( 104, 104a, 104b) are not limited to the materials described above, and other materials can be used in combination as long as they can satisfy the functions of each layer. As an example , a high molecular compound (oligomer, dendrimer, polymer, etc.), a medium molecular compound (a compound in the intermediate region between low molecules and high molecules: molecular weight 400 to 4000), an inorganic compound (quantum dot materials, etc.) can be used. Note that 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 etc. can be used.

[0185] The configuration shown in this embodiment can be used in appropriate combination with the configuration shown in other embodiments .

[0186] (Embodiment 3) In this embodiment, a light-emitting device which is one aspect of the present invention will be described. Note that the light-emitting device shown in FIG. 2(A) is an active matrix type light-emitting device in which a transistor (FET) 202 and a light-emitting element (2 03R, 203G, 203B, 203W) on a first substrate 201 are electrically connected, and a plurality of light-emitting elements (203R, 203G, 203B, 203W) have a common EL layer 204, and, according to the emission color of each light-emitting element, between the electrodes of each light-emitting element It has a microcavity structure with an adjusted optical distance. Also, the light emitted from the EL layer 204 is emitted through color filters (206R, 206G, 206 B) formed on the second substrate 205, which is a top-emission type light-emitting device.

[0187] The light-emitting device shown in Fig. 2(A) is formed such that the first electrode 207 functions as a reflective electrode. Also, the second electrode 208 is formed to function as a semi-transmissive and semi-reflective electrode. Note that as the electrode materials for forming the first electrode 207 and the second electrode 208, other embodiments may be referred to and used as appropriate.

[0188] Also, in Fig. 2(A), for example, when the light-emitting element 203R is a red light-emitting element, the light-emitting element 203 G 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 as shown in Fig. 2(B), 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 so that the optical distance between the first electrode 207 and the second electrode 208 is 200G, and the light-emitting element 2 03B is adjusted so that the optical distance between the first electrode 207 and the second electrode 208 is 200B. As shown in Fig. 2(B), in the light-emitting element 203R, the conductive layer 210R is stacked on the first electrode 207, and in the light-emitting element 203G, the conductive layer 210G is stacked on the first electrode 20 7, whereby optical adjustment can be performed. On the second substrate 205, color filters (206R, 206G, 206B) are formed. Note that the color filters transmit a specific wavelength range of visible light and block a specific wavelength range of visible light.

[0189] The second substrate 205 has color filters (206R, 206G, 206B) formed thereon. Note that the color filter passes a specific wavelength range of visible light and blocks a specific wavelength range of It is a filter for blocking. Therefore, as shown in Fig. 2(A), by providing a color filter 206R that allows only the red wavelength range to pass through at a position overlapping with the light-emitting element 203R, red light emission can be obtained from the light-emitting element 203R. Also, by providing a color filter 206G that allows only the green wavelength range to pass through at a position overlapping with the light-emitting element 203G, green light emission can be obtained from the light-emitting element 203G. Further, by providing a color filter 206B that allows only the blue wavelength range to pass through at a position overlapping with the light-emitting element 203B, blue light emission can be obtained from the light-emitting element 203B. However, for the light-emitting element 203W, white light emission can be obtained without providing a color filter. Note that a black layer (black matrix) 209 may be provided at the end of one type of color filter. Furthermore, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer made of a transparent material. At the position overlapping with the light-emitting element 203R, a color filter 206R that allows only the red wavelength range to pass through is provided, so that red light emission can be obtained from the light-emitting element 203R. Also, at the position overlapping with the light-emitting element 203G, a color filter 206G that allows only the green wavelength range to pass through is provided, so that green light emission can be obtained from the light-emitting element 203G. At the position overlapping with the light-emitting element 203G, a color filter 206G that allows only the green wavelength range to pass through is provided, so that green light emission can be obtained from the light-emitting element 203G. Also, at the position overlapping with the light-emitting element 203B, a color filter 206B that allows only the blue wavelength range to pass through is provided, so that blue light emission can be obtained from the light-emitting element 203B. At the position overlapping with the light-emitting element 203B, a color filter 206B that allows only the blue wavelength range to pass through is provided, so that blue light emission can be obtained from the light-emitting element 203B. However, for the light-emitting element 203W, white light emission can be obtained without providing a color filter. Note that a black layer (black matrix) 209 may be provided at the end of one type of color filter. Furthermore, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer made of a transparent material. Furthermore, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer made of a transparent material. Furthermore, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer made of a transparent material.

[0190] In Fig. 2(A), a light-emitting device having a structure (top emission type) for extracting light emission on the second substrate 205 side is shown. However, as shown in Fig. 2(C), it may be a light-emitting device having a structure (bottom emission type) for extracting light on the first substrate 201 side where the FET 202 is formed. Note that in the case of a bottom emission type 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. Also, the first substrate 201 uses at least a light-transmissive substrate. Also, the color filters (206R’, 206G’, 206B’) may be provided on the first substrate 201 side rather than the light-emitting elements (203R, 203G, 203B) as shown in Fig. 2(C). In Fig. 2(A), a light-emitting device having a structure (top emission type) for extracting light emission on the second substrate 205 side is shown. However, as shown in Fig. 2(C), it may be a light-emitting device having a structure (bottom emission type) for extracting light on the first substrate 201 side where the FET 202 is formed. Note that in the case of a bottom emission type 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. Also, the first substrate 201 uses at least a light-transmissive substrate. Also, the color filters (206R’, 206G’, 206B’) may be provided on the first substrate 201 side rather than the light-emitting elements (203R, 203G, 203B) as shown in Fig. 2(C). Also, the first substrate 201 uses at least a light-transmissive substrate. Also, the color filters (206R’, 206G’, 206B’) may be provided on the first substrate 201 side rather than the light-emitting elements (203R, 203G, 203B) as shown in Fig. 2(C). Also, the color filters (206R’, 206G’, 206B’) may be provided on the first substrate 201 side rather than the light-emitting elements (203R, 203G, 203B) as shown in Fig. 2(C).

[0191] Also, in FIG. 2(A), although the light-emitting element has been shown in the case of a red light-emitting element, a green light-emitting element, a blue light-emitting element, and a white light-emitting element, the light-emitting element which is one aspect of the present invention is not limited to its configuration, and a configuration having a yellow light-emitting element or an orange light-emitting element may be used. Incidentally, in order to fabricate these light-emitting elements, materials used for the EL layer (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, charge generation layer, etc.) may be referred to the description of other embodiments and used as appropriate. In that case, also, a color filter needs to be appropriately selected according to the emission color of the light-emitting element.

[0192] By adopting the above configuration, a light-emitting device including a light-emitting element exhibiting a plurality of emission colors can be obtained.

[0193] Note that the configuration shown in this embodiment can be used in appropriate combination with the configuration shown in other embodiments.

[0194] (Embodiment 4) In this embodiment, a light-emitting device which is one aspect of the present invention will be described.

[0195] By applying the element configuration of the light-emitting element which is one aspect of the present invention, an active matrix type light-emitting device or a passive matrix type light-emitting device can be fabricated. Note that an active matrix type light-emitting device has a configuration in which a light-emitting element and a transistor (FET) are combined. Therefore, a passive matrix type light-emitting device and an active matrix type light-emitting device are both included in one aspect of the present invention. Note that the light-emitting device shown in this embodiment can apply the light-emitting elements described in other embodiments.

[0196] In this embodiment, an active matrix light-emitting device will be described with reference to FIG. 3.

[0197] Note that FIG. 3(A) is a top view showing the light-emitting device, and FIG. 3(B) is a cross-sectional view taken along the chain line A-A ' in FIG. 3(A). The active matrix light-emitting device includes a pixel portion 302 provided on a first substrate 301, a driving circuit portion (source line driving circuit) 303, and driving circuit portions (gate line driving circuits) (304a, 304b). The pixel portion 302 and the driving circuit portions (3 03, 304a, 304b) are sealed between the first substrate 301 and the second substrate 306 by a sealing material 305.

[0198] In addition, a routing wiring 307 is provided on the first substrate 301. The routing wiring 307 is electrically connected to an FPC 308 which is an external input terminal. Note that the FPC 308 transmits external signals (e.g., video signals, clock signals, start signals, reset signals, etc.) and potentials to the driving circuit portions (303, 304a, 304b). Further, a printed wiring board (PWB) may be attached to the FPC 308. Note that the state where these FPCs and PWBs are attached is included in the light-emitting device.

[0199] Next, the cross-sectional structure is shown in FIG. 3(B).

[0200] 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. ​​

[0201] FETs 309, 310, 311, and 312 are not particularly limited, and for example, transistors such as the staggered type or the inverse staggered type can be applied. Also, a transistor structure such as a top gate type or a bottom gate type may be used.

[0202] In addition, the crystallinity of the semiconductor that can be used for these FETs 309, 310, 311, and 312 is not particularly limited, and any of an amorphous semiconductor, a semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single-crystalline semiconductor, or a semiconductor having a crystalline region in part) may be used. Moreover, by using a semiconductor having crystallinity, deterioration of transistor characteristics can be suppressed, which is preferable.

[0203] Also, as these semiconductors, for example, group 14 elements, compound semiconductors, oxide semiconductors, organic semiconductors, etc. can be used. Typically, semiconductors containing silicon, gallium arsenic-containing semiconductors, indium-containing oxide semiconductors, etc. can be applied.

[0204] The drive circuit section 303 has FET 309 and FET 310. Note that FET 309 and F ET 310 may be formed of a circuit containing a unipolar (either N-type or P-type only) transistor, or may be formed of a CMOS circuit containing an N-type transistor and a P-type transistor. Also, it may be configured to have a drive circuit externally.

[0205] The end of the first electrode 313 is covered by an insulator 314. Note that the insulator 314 includes organic compounds such as a negative-type photosensitive resin or a positive-type photosensitive resin (acrylic resin), and acids ​Inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride can be used. It is preferred that the upper or lower end of the insulator 314 has a curved surface with a curvature. This can improve the coating property of the film formed on the upper layer of the insulator 314. On the first electrode 313, an EL layer 315 and a second electrode 316 are laminated and formed. The EL layer 315 has a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc.

[0206] On the first electrode 313, an EL layer 315 and a second electrode 316 are laminated and formed. The EL layer 315 has a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. has.

[0207] Note that the configuration of the light-emitting element 317 shown in this embodiment can apply the configurations and materials described in other embodiments. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal. Note that the configuration of the light-emitting element 317 shown in this embodiment can apply the configurations and materials described in other embodiments. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal. terminal.

[0208] Also, in the cross-sectional view shown in FIG. 3(B), only one light-emitting element 317 is shown, but in the pixel portion 3 02, a plurality of light-emitting elements are arranged in a matrix. In the pixel portion 30 2, light-emitting elements capable of obtaining three types (R, G, B) of light emission are selectively formed respectively, and a light-emitting device capable of full-color display can be formed. Also, in addition to the light-emitting elements capable of obtaining three types (R, G, B) of light emission, for example, light-emitting elements capable of obtaining light emission such as white (W), yellow (Y), magenta (M ) cyan (C), etc. may be formed. For example, by adding light-emitting elements capable of obtaining the above-mentioned several types of light emission to the light-emitting elements capable of obtaining three types (R, G, B) of light emission, effects such as improvement of color purity and reduction of power consumption can be obtained. Also, it may be a light-emitting device capable of full-color display by combining with a color filter. Note that by combining with a color filter, it may be a light-emitting device capable of full-color display. Note that by adding light-emitting elements capable of obtaining the above-mentioned several types of light emission to the light-emitting elements capable of obtaining three types (R, G, B) of light emission, effects such as improvement of color purity and reduction of power consumption can be obtained. Also, it may be a light-emitting device capable of full-color display by combining with a color filter. Note that by combining with a color filter, it may be a light-emitting device capable of full-color display. Note , As types of color filters, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), etc. can be used. , and the like.

[0209] The FETs (309, 310, 311, 312) and the light-emitting element 317 on the first substrate 301 , by bonding the second substrate 306 and the first substrate 301 with a sealing material 305 , have a structure provided in the space 318 surrounded by the first substrate 301, the second substrate 306, and the sealing material 305. Note that the space 318 may be filled with an inert gas (such as nitrogen or argon) or an organic substance (including the sealing material 305).

[0210] For the sealing material 305, an epoxy resin or glass frit can be used. Note that it is preferable to use a material that hardly permeates moisture and oxygen for the sealing material 305. In addition, the second substrate 306 can be used in the same manner as those that can be used for the first substrate 301. Therefore, it is assumed that various substrates described in other embodiments can be appropriately used. As the substrate, in addition to a glass substrate and a quartz substrate, a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, or acrylic resin, etc. can be used. When using glass frit as the sealing material, from the viewpoint of adhesiveness, the first substrate 301 and the second substrate 306 are preferably glass substrates.

[0211] As described above, an active matrix type light-emitting device can be obtained.

[0212] In addition, when forming an active matrix type light-emitting device on a flexible substrate, on the flexible substrate An FET and a light-emitting element may be formed directly, or after forming an FET and a light-emitting element on another substrate having a release layer, the FET and the light-emitting element may be peeled off at the release layer by applying heat, force, laser irradiation, etc., and then transferred onto a flexible substrate for fabrication. As the release layer, for example, a laminate of inorganic films such as a tungsten film and a silicon oxide film, or an organic resin film such as polyimide 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 (including natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester), or regenerated fibers (acetate, cupra, rayon, regenerated polyester), etc.), a leather substrate, or a rubber substrate can be mentioned. By using these substrates, excellent durability and heat resistance can be achieved, and weight reduction and thinning can be realized. After forming an FET and a light-emitting element on another substrate having a release layer, the FET and the light-emitting element may be peeled off at the release layer by applying heat, force, laser irradiation, etc., and then transferred onto a flexible substrate for fabrication. In addition, as the release layer, for example, a laminate of inorganic films such as a tungsten film and a silicon oxide film, or an organic resin film such as polyimide 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 (including natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester), or regenerated fibers (acetate, cupra, rayon, regenerated polyester), etc.), a leather substrate, or a rubber substrate can be mentioned. By using these substrates, excellent durability and heat resistance can be achieved, and weight reduction and thinning can be realized. In addition, as the release layer, for example, a laminate of inorganic films such as a tungsten film and a silicon oxide film, or an organic resin film such as polyimide 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 (including natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester), or regenerated fibers (acetate, cupra, rayon, regenerated polyester), etc.), a leather substrate, or a rubber substrate can be mentioned. By using these substrates, excellent durability and heat resistance can be achieved, and weight reduction and thinning can be realized. Note that the configurations shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments.

[0213] Note that the configurations shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments.

[0214] (Embodiment 5) In this embodiment, an example of various electronic devices and automobiles completed by applying a light-emitting element which is one aspect of the present invention and a light-emitting device having a light-emitting element which is one aspect of the present invention will be described. Note that the light-emitting device can be mainly applied to a display portion in the electronic devices described in this embodiment. Note that the light-emitting device can be mainly applied to a display portion in the electronic devices described in this embodiment.

[0215] The electronic device shown in FIGS. 4(A) to 4(C) includes a housing 7000, a display portion 7001, a speaker 7003, an LED lamp 7004, and operation keys 7005 (power switch or operation switch including), connection terminal 7006, sensor 7007 (force, displacement, position, speed, acceleration, angular velocity , rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage , power, radiation, flow rate, humidity, gradient, vibration, odor, or having a function of measuring infrared rays ), microphone 7008, etc. can be provided.

[0216] FIG. 4(A) is a mobile computer, and in addition to the above-described components, it can have a switch 7009, an infrared port 7010, etc.

[0217] FIG. 4(B) is a portable image playback device (e.g., a DVD playback device) equipped with a recording medium, and in addition to the above-described components, it can have a second display unit 7002, a recording medium reading unit 7011, etc.

[0218] FIG. 4(C) is a digital camera with a television reception function, and in addition to the above-described components, it can have an antenna 7014, a shutter button 7015, an imaging unit 7016, etc.

[0219] FIG. 4(D) is a portable information terminal. The portable information terminal has a function of displaying information on three or more sides of the display unit 7001. Here, an example is shown where information 7052, information 7053, and information 7054 are respectively displayed on different sides. For example, the user can confirm the information 7053 displayed at a position where it can be observed from above the portable information terminal while the portable information terminal is stored in the breast pocket of the clothing. The user can confirm the display without taking the portable information terminal out of the pocket and, for example, determine whether to answer a call.

[0220] FIG. 4(E) is a portable information terminal (including a smartphone), and on the housing 7000, there is a display unit 7 ​​​​​​​​001. It can have operation keys 7005, etc. Note that the portable information terminal may be equipped with a speaker. It may also be provided with a connection terminal, a sensor, etc. Also, the portable information terminal can display character and image information on its multiple faces. Here, an example of displaying three icons 7050 is shown. Also, the information 7051 indicated by the dashed rectangle can be displayed on other faces of the display unit 7001. As an example of the information 7051, there are notifications of incoming calls such as e-mails, SNS, and phone calls, titles, sender names, dates, times, remaining battery levels, antenna reception strengths, etc. of e-mails and SNS. Or, an icon 7050 or the like may be displayed at the position where the information 7051 is displayed.

[0221] FIG. 4(F) shows a large television device (also referred to as a TV or a television receiver), which can have a housing 7000, a display unit 7001, etc. Here, a configuration in which the housing 7000 is supported by a stand 7018 is shown. Also, the operation of the television device can be performed by a separate remote control operation device 7111, etc. Note that the display unit 7 001 may be provided with a touch sensor, and it may be operated by touching the display unit 7001 with a finger or the like. The remote control operation device 7111 may have a display unit for displaying the information output from the remote control operation device 7111. The operation keys or touch panel provided in the remote control operation device 7111 can be used to operate the channel and volume, and the image displayed on the display unit 7001 can be operated.

[0222] The electronic devices shown in FIGS. 4(A) to 4(F) can have various functions. For example, it has a function of displaying various information (still images, moving images, text images, etc.) on the display unit, a touch panel functions such as the <ル> function, calendar, date, or time display function, functions for controlling processing by various software (programs), wireless communication functions, functions for connecting to various computer networks using the wireless communication function, functions for transmitting or receiving various data using the wireless communication function, functions for reading programs or data recorded on a recording medium and displaying them on a display unit, etc. can be included. Further, in an electronic device having a plurality of display units, it is possible to mainly display image information on one display unit and mainly display character information on another display unit, or to display a stereoscopic image by displaying an image considering parallax on a plurality of display units, etc. Further, in an electronic device having an imaging unit, it is possible to have functions such as a function for taking still images, a function for taking moving images, a function for automatically or manually correcting the captured images, a function for storing the captured images on a recording medium (external or built into the camera), a function for displaying the captured images on a display unit, etc. Note that the functions that the electronic device shown in FIGS. 4(A) to 4(F) can have are not limited to these, and it can have various functions.

[0223] FIG. 4(G) shows a wristwatch-type portable information terminal, which can be used, for example, as a smartwatch. This wristwatch-type portable information terminal has a housing 7000, a display unit 7001, operation buttons 7022, 7023, a connection terminal 7024, a band 7025, a microphone 7026 a speaker 7030, etc. The display unit 7001 has a curved display surface and can perform display along the curved display surface. Further, this portable information terminal is capable of hands-free calling, for example, through mutual communication with a wirelessly communicable headset.​​​​​​​​​​​​ Yes. Additionally, the connection terminal 7024 can perform data transmission with other information terminals and perform charging. The charging operation can also be performed by wireless power supply.

[0224] The display unit 7001 mounted on the housing 7000 that also serves as the bezel portion has a non-rectangular display area. The display unit 7001 can display icons representing time and other icons. Further, the display unit 7001 may be a touch panel (input / output device) equipped with a touch sensor (input device).

[0225] Note that the smartwatch shown in FIG. 4(G) can have various functions. For example, it can have functions such as displaying various information (still images, videos, text images, etc.) on the display unit, touch panel function, function of displaying a calendar, date, or time, function of controlling processing by various software (programs), wireless communication function, function of connecting to various computer networks using the wireless communication function, function of transmitting or receiving various data using the wireless communication function, function of reading a program or data recorded on a recording medium and displaying it on the display unit, etc.

[0226] Also, inside the housing 7000, there can be a speaker, a sensor (including functions for measuring force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, electric power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), microphone, etc.

[0227] Note that a light-emitting device which is one aspect of the present invention and a display having a light-emitting element which is one aspect of the present invention ​The device can be used for each display portion of the electronic device shown in this embodiment, and has a long life. This can be achieved.

[0228] In addition, as an electronic device to which a light-emitting device is applied, a folding type electronic device as shown in FIG. FIG. 5A shows a portable information terminal 93 in an unfolded state. 10. Also, FIG. 5(B) shows the state of the unfolded or folded state. 5C shows the mobile information terminal 9310 in the process of changing to the folded state. The portable information terminal 9310 in a folded state is shown. The portable information terminal 9310 in a folded state is shown. When unfolded, it has excellent portability, and when unfolded, it has a seamless, wide display area that allows for easy viewing of the display. Excellent.

[0229] The display unit 9311 is supported by three housings 9315 connected by hinges 9313. The display unit 9311 is a touch panel (input / output) equipped with a touch sensor (input device). The display unit 9311 may be connected to two housings via a hinge 9313. By bending the gap between the terminals 9315, the portable information terminal 9310 can be folded from the unfolded state. The light-emitting device of one embodiment of the present invention can be reversibly transformed into a display state. The display portion 9311 can be used as a display unit. In addition, a long-life electronic device can be realized. The display area 9312 in FIG. 1 is located on the side of the portable information terminal 9310 in the folded state. The display area 9312 displays information icons and frequently used apps and programs. You can display shortcuts to programs, check information, and launch apps. It can be done smoothly.

[0230] In addition, an automobile to which the light-emitting device is applied is shown in FIGS. 6(A) and 6(B). That is, the light-emitting device can be provided integrally with the automobile. Specifically, for the automobile shown in FIG. 6(A), the outer lights 5101 (including the rear part of the vehicle body), the wheels 5102 of the tires, and the doors 5103 can be applied to part or all of them. Also, for the interior display part 5104, the steering wheel 5105, the shift lever 5106, the seat 5107, the inner rearview mirror 5108, etc. of the automobile shown in FIG. 6(B) can be applied. In addition, it may be applied to a part of the glass window.

[0231] As described above, electronic devices and automobiles to which the light-emitting device or the display device, which is an aspect of the present invention, is applied can be obtained. In that case, long-life electronic devices can be realized. Note that the applicable electronic devices and automobiles are not limited to those shown in this embodiment, and can be applied in any field.

[0232] Note that the configurations shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments.

[0233] (Embodiment 6) In this embodiment, the configuration of a lighting device manufactured by applying the light-emitting device, which is an aspect of the present invention, or a light-emitting element, which is a part of the light-emitting device, will be described with reference to FIG. 7.

[0234] FIGS. 7(A) and 7(B) show an example of a cross-sectional view of the lighting device. Note that FIG. 7(A) is a bottom emission type lighting device that emits light from the substrate side, and FIG. 7(B) is a top emission type lighting device that emits light from the sealing substrate side.

[0235] ​​​​​​​​The lighting device 4000 shown in Fig. 7(A) has a light-emitting element 4002 on a substrate 4001. Also, it has a substrate 4003 with irregularities on the outside of the substrate 4001. The light-emitting element 4002 has a first electrode 4004, an EL layer 4005, and a second electrode 4006.

[0236] The first electrode 4004 is electrically connected to an electrode 4007, and the second electrode 4006 is electrically connected to an electrode 4 008. Also, an auxiliary wiring 4009 electrically connected to the first electrode 4004 may be provided. An insulating layer 4010 is formed on the auxiliary wiring 4009.

[0237] Also, the substrate 4001 and the sealing substrate 4011 are adhered with a sealing material 4012. Also, it is preferable that a desiccant 4013 is provided between the sealing substrate 4011 and the light-emitting element 4002. Since the substrate 4003 has irregularities as shown in Fig. 7(A), the extraction efficiency of the light generated by the light-emitting element 4002 can be improved.

[0238] The lighting device 4200 in Fig. 7(B) has a light-emitting element 4202 on a substrate 4201. The light-emitting element 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206.

[0239] The first electrode 4204 is electrically connected to an electrode 4207, and the second electrode 4206 is electrically connected to an electrode 4 208. Also, an auxiliary wiring 4209 electrically connected to the second electrode 4206 may be provided. Also, an insulating layer 4210 may be provided below the auxiliary wiring 4209.

[0240] The substrate 4201 and the sealing substrate 4211 with irregularities are adhered with a sealing material 4212. Also, A barrier film 4213 and a planarization film 4214 may be provided between the sealing substrate 4211 and the light-emitting element 4202. Since the sealing substrate 4211 has irregularities as shown in FIG. 7(B), the extraction efficiency of the light generated by the light-emitting element 4202 can be improved.

[0241] In addition, as an application example of these lighting devices, a ceiling light for indoor lighting can be mentioned. There are ceiling-mounted types and ceiling-embedded types for ceiling lights. Such lighting devices are configured by combining a light-emitting device with a housing or a cover.

[0242] In addition, it can also be applied to a footlight that irradiates the floor surface to enhance the safety of the feet. The footlight is effective, for example, when used in a bedroom, a staircase, or a passage. In that case, the size and shape can be appropriately changed according to the size and structure of the room. It is also possible to use a stationary lighting device configured by combining a light-emitting device and a support base.

[0243] It can also be applied as a sheet-shaped lighting device (sheet-shaped lighting). Since the sheet-shaped lighting is attached to the wall surface and used, it can be used for a wide range of applications without taking up space. In addition, it is easy to increase the area. It can also be used for a wall surface or a housing having a curved surface.

[0244] In addition to the above, a light-emitting device according to one aspect of the present invention, or a light-emitting element which is a part thereof, can be applied to a part of furniture provided indoors, and a lighting device having a function as furniture can be obtained.

[0245] As described above, various lighting devices to which the light-emitting device is applied can be obtained. These lighting devices ​​​​​​​​​​is included in one aspect of the present invention.

[0246] In addition, the configurations shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments. It can be used.

Example

[0247] ≪Synthesis Example 1≫ In this example, an organic compound which is one aspect of the present invention represented by the structural formula (100) of Embodiment 1, 8-(1,1'-biphenyl-4-yl)-4-[3-(dibenzothiophene-4 -yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4m DBtPBfpm) will be described. The structure of 8BP-4mDBtPBfpm is shown below. DBtPBfpm is shown below.

[0248]

Chemical formula

[0249] <8-(1,1'-biphenyl-4-yl)-4-[3-(dibenzothiophene-4-yl phenyl]-[1]benzofuro[3,2-d]pyrimidine synthesis> 1.37 g of 8-chloro-4-[3-(dibenzothiophene-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine, 0.657 g of 4-biphenylboronic acid, potassium phosphate tripotassium 1.91 g, 30 mL of diethylene glycol dimethyl ether (diglyme), and 0.662 g of t-butanol were placed in a three-necked flask, and the inside of the flask was stirred under reduced pressure to degas and then nitrogen-substituted. This mixture was heated to 60 °C, and 23.3 mg of palladium(II) acetate, di(1-adamantyl was added.

[0250] This mixture was heated to 60 °C, and 23.3 mg of palladium(II) acetate, di(1-adamantyl 66.4 mg of (ethyl)-n-butylphosphine was added, and the mixture was stirred at 120° C. for 27 hours. Water was added to the reaction solution, which was then subjected to suction filtration. The residue was washed with water, ethanol, and toluene. The residue was dissolved in hot toluene and packed in the following order: Celite, alumina, and Celite. The resulting solution was concentrated to dryness and recrystallized from toluene to give The target product, a white solid, was obtained in an amount of 1.28 g and a yield of 74%.

[0251] 1.26 g of this white solid was purified by train sublimation. The conditions were a pressure of 2.56 Pa, argon gas flow rate of 10 mL / min, and a temperature of 310 The solid was heated at 50°C. After purification by sublimation, 1.01 g of the target pale yellow solid was obtained with a recovery rate of 80%. The synthesis scheme is shown in the following formula (a-1).

[0252] [ka]

[0253] The pale yellow solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR chart is shown in FIG. In the present invention, the organic compound represented by the above structural formula (100) is 8BP- It was found that 4mDBtPBfpm was obtained.

[0254] 1 H-NMR.δ(CDCl3):7.39(t,1H), 7.47-7.53(m,4 H), 7.63-7.67(m,2H), 7.68(d,2H), 7.75(d,2H) , 7.79-7.83(m,4H), 7.87(d,1H), 7.98(d,1H), 8 .02 (d, 1H), 8.23 - 8.26 (m, 2H), 8.57 (s, 1H), 8.7 3 (d, 1H), 9.05 (s, 1H), 9.34 (s, 1H).

[0255] ≪Properties of 8BP - 4mDBtPBfpm≫ Next, the ultraviolet - visible absorption spectra and emission spectra of the toluene solution and solid thin film of 8BP - 4mDBtPBfpm were measured.

[0256] For the measurement of the absorption spectrum in the toluene solution, an ultraviolet - visible spectrophotometer (V550 type, manufactured by JASCO Corporation) was used. Also, for the measurement of the emission spectrum in the toluene solution, a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.) was used. The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Fig. 9(A). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0257] From Fig. 9(A), the toluene solution of 8BP - 4mDBtPBfpm shows absorption peaks around 332 nm, 316 n m and 281 nm, and the peak of the emission wavelength is 406 nm (excitation wavelength 318 nm).

[0258] For the measurement of the absorption spectrum of the solid thin film, a solid thin film prepared by vacuum evaporation on a quartz substrate was used, and measured using an ultraviolet - visible spectrophotometer (U4100 type, manufactured by Hitachi High - Technologies Corporation). Also, for the measurement of the emission spectrum of the solid thin film, the same solid thin film as above was used, and measured using a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.). The measurement results of the absorption spectrum and emission spectrum of the obtained solid thin film are shown in Fig. 9(B). The horizontal axis represents the wavelength, and the vertical axis represents the absorption ​​It represents the absorption intensity and the emission intensity. Also, using the same solid thin film as above, the microscopic PL apparatus Lab RAM HR-PL (manufactured by Horiba, Ltd.) was used. The measurement temperature was 10 K, and a He-Cd laser with a wavelength of 325 nm was used as the excitation light. A CCD detector was used as the detector to measure the emission spectrum at low temperature (10 K).

[0259] From FIG. 9(B), in the solid thin film of 8BP-4mDBtPBfpm, absorption peaks were observed at around 341 nm, 308 nm, 286 nm, 273 nm, and 243 nm, and a peak of the emission wavelength was observed at around 428 nm (excitation wavelength 340 nm). Also, from the results of the emission spectrum at low temperature (10 K), the wavelength of the peak on the shortest wavelength side (including the shoulder) of the phosphorescence component of the emission spectrum of 8BP-4mDBtPBfpm was 482 nm. Therefore, from the above peak wavelengths, the T1 level of 8BP-4mDBtPBfpm was calculated to be 2.57 eV

[0260] The organic compound 8BP-4mDBtPBfpm, which is one embodiment of the present invention, has a high T1 level and can be said to be a host material suitable for a phosphorescent material (guest material) that emits light in the vicinity of green to red In addition, the organic compound 8BP-4mDBtPBfpm, which is one embodiment of the present invention, can also be used as a host material or a luminescent substance for a phosphorescent luminescent substance in the visible region.

Example

[0261] ≪Synthesis Example 2≫ In this example, the organic compound, which is one embodiment of the present invention represented by the structural formula (101) of Embodiment 1, 8-(1,1'-biphenyl-3-yl)-4-[3-(dibenzothiophene-4 -yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8mBP-4 ​​​​​​​​​ The synthesis method of mDBtPBfpm) will be described. Note that 8mBP-4mDBtPBf The structure of pm is shown below.

[0262] [Chemical formula]

[0263] <8-(1,1'-Biphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine synthesis> 1.37 g of 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzof uro[3,2-d]pyrimidine, 0.664 g of 3-biphenylboronic acid, tripotassium phosphate 1.90 g, 0.663 g of t-butanol, and 30 mL of diglyme were placed in a three-necked flask, degassed by stirring under reduced pressure, and substituted with nitrogen. This mixture was heated to 60 °C, and 21.4 mg of palladium(II) acetate and 65.6 mg of di(1-adamantyl)-n-butylphosphine

[0264] were added, and the mixture was stirred at 120 °C for 21 hours. 23.5 mg of palladium(II) acetate and 66.4 mg of di(1-adamantyl)-n-but ylphosphine were added to this reaction product, and the mixture was stirred at 120 °C for 8 hours. Water was added to this reaction product, and it was suction filtered, and the obtained filtrate was washed with water, ethanol, and toluene. This filtrate was dissolved in hot toluene and passed

[0265] through a filter aid filled in the order of celite, alumina, and celite. The obtained solution was concentrated, dried, and recrystallized from toluene to obtain 1.10 g of the target white solid with a yield of 64%.

[0265] 1.10 g of this white solid was sublimation-purified by the train sublimation method. Sublimation purification The conditions were as follows: while flowing argon gas at a flow rate of 10 mL / min under a pressure of 2.57 Pa, the solid was heated at 300 °C. After sublimation purification, 0.895 g of the desired pale yellow solid was obtained with a recovery rate of 81%. This synthetic scheme is shown in the following formula (b-1).

[0266]

Chemical formula

[0267] In addition, the analysis results of the pale yellow solid obtained from the above reaction by nuclear magnetic resonance spectroscopy ( 1 1H-NMR) are shown below. Also, the 1H-NMR chart is shown in FIG. 10. From these results, in this example, 1 the organic compound, 8mB P-4mDBtPBfpm, which is one aspect of the present invention represented by the above structural formula (101), was obtained.

[0268] 1 1H-NMR. δ(CDCl3): 7.39 (t, 1H), 7.47 - 7.50 (m, 4 H), 7.57 (t, 1H), 7.62 - 7.64 (m, 3H), 7.67 - 7.69( m, 3H), 7.77 - 7.80 (m, 2H), 7.86 (d, 1H), 7.92 (s, 1H), 7.79 (d, 1H), 8.00 (d, 1H), 8.21 - 8.23 (m, 2H ), 8.57 (s, 1H), 8.71 (d, 1H), 9.03 (s, 1H), 9.32( s, 1H).

[0269] ≪Regarding the physical properties of 8mBP-4mDBtPBfpm≫ Next, the ultraviolet-visible absorption spectra (hereinafter simply referred to as "absorption spectra") and emission spectra of toluene solutions and solid thin films of 8mBP-4mDBtPBfpm were measured.

[0270] ​​ For the measurement of the absorption spectrum in toluene solution, a UV-visible spectrophotometer (manufactured by JASCO Corporation) Model V550 was used. Also, for the measurement of the emission spectrum in toluene solution, a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics K.K.) was used. The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Fig. 11(A). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0271] From Fig. 11(A), the toluene solution of 8mBP-4mDBtPBfpm shows absorption peaks around 331 nm, 31 5 nm, and 280 nm, and the peak of the emission wavelength is 389 nm (excitation wavelength 320 nm).

[0272] For the measurement of the absorption spectrum of the solid thin film, a solid thin film prepared by vacuum evaporation on a quartz substrate was used, and measured using a UV-visible spectrophotometer (U4100 model manufactured by Hitachi High-Technologies Corporation). Also, for the measurement of the emission spectrum of the solid thin film, the same solid thin film as above was used, and measured using a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics K.K.). The measurement results of the absorption spectrum and emission spectrum of the obtained solid thin film are shown in Fig. 11(B). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. Also, using the same solid thin film as above, a microscopic PL device La bRAM HR-PL (manufactured by Horiba, Ltd.) was used, the measurement temperature was 10 K, and as the excitation light, a He-Cd laser with a wavelength of 325 nm was used, and a CCD detector was used as the detector to measure the emission spectrum at low temperature (1 0 K). From Fig. 11(B), in the solid thin film of 8mBP-4mDBtPBfpm, at 343 nm, 31

[0273] Absorption peaks are observed near 9 nm and 245 nm, and a peak in the emission wavelength is observed near 411 nm (excitation wavelength 320 nm). Moreover, from the results of the emission spectrum at low temperature (10 K), the wavelength of the peak on the shortest wavelength side of the phosphorescence component of the emission spectrum of 8mBP-4mDBtPBfpm (including the shoulder) was 456 nm. Therefore, from the above peak wavelength, the T1 level of 8 mBP-4mDBtPBfpm was calculated to be 2.72 eV.

[0274] The organic compound, 8mBP-4mDBtPBfpm, which is one aspect of the present invention, has a high T1 level and can be said to be a host material suitable for a phosphorescent material (guest material) that emits light in the range from green to near red. Note that the organic compound, 8mBP-4mDBtPBfpm, which is one aspect of the present invention, can also be used as a host material or a luminescent substance for a phosphorescent luminescent substance in the visible region.

Example

[0275] ≪Synthesis Example 3≫ In this example, the synthesis method of the organic compound, 8-[(2,2'-binaphthalen)-6-yl]-4-[3-(dibenzothiophene -4-yl)phenyl-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN 2)-4mDBtPBfpm), which is one aspect of the present invention represented by the structural formula (102) of Embodiment 1, will be described. Note that the structure of 8(βN2)-4m DBtPBfpm is shown below.

[0276]

Chemical formula

[0277] <8-[(2,2’-binaphthalen)-6-yl]-4-[3-(dibenzothiophene- Synthesis of 4-(3-(dibenzothiophen-4-yl)phenyl)-[1]benzofuro[3,2-d]pyrimidine> 8-Chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzof uro[3,2-d]pyrimidine 1.21 g, [2,2'-binaphthalene]-6-ylboronic acid 0.857 g, tripotassium phosphate 1.67 g, diglyme 26 mL, t-butanol 0. 583 g were placed in a three-necked flask, and the inside of the flask was degassed by stirring under reduced pressure and then purged with nitrogen. Then.

[0278] This mixture was heated to 60 °C, and palladium(II) acetate 18.9 mg and di(1-adamantyl)-n-butylphosphine 61.1 mg were added, followed by stirring at 120 °C for 10 hours. Water was added to the reaction solution and suction filtration was carried out. The obtained filtrate was washed with water, ethanol, and toluene. The filtrate was dissolved in hot toluene and passed through a filter aid filled in the order of celite, alumina, and celite. The resulting solution was concentrated to dryness to obtain a white solid. All of the obtained solid, [2,2'-binaphthalene]-6-ylboronic acid 0.348 g, tripotassium phosphate 0.621 g, diglyme 13 mL, and t-butanol 0.239 g were placed in a three-necked flask.

[0279] The inside of the flask was degassed by stirring under reduced pressure and then purged with nitrogen. This mixture was heated to 6 0 °C, and palladium(II) acetate 8.7 mg and di(1-adamantyl)-n-butyl phosphine 25.1 mg were added, followed by stirring at 120 °C for 18.5 hours. Water was added to the reaction solution and suction filtration was carried out. The obtained filtrate was washed with water, ethanol, and toluene. The filtrate was dissolved in hot toluene and passed through a filter filled in the order of celite, alumina, and celite. This filtrate was washed with water, ethanol, and toluene.

[0280] The filtrate was dissolved in hot toluene and passed through a filter filled with celite, alumina, and celite in that order. The resulting solution was concentrated to dryness and recrystallized in toluene to obtain the target compound. The resulting white solid was 1.16 g in a yield of 65%. The sublimation purification was carried out by the rain sublimation method. The sublimation purification conditions were a pressure of 2.64 Pa and The solid was heated at 365°C while flowing argon gas at a flow rate of 10 mL / min. After that, 0.958 g of 8(βN2)-4mDBtPBfpm of the present invention (recovery rate 83%, The synthesis scheme is shown in formula (c-1) below.

[0281] [ka]

[0282] The white solid obtained in the above reaction was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR Analysis Results The following is a summary of the 1 The H-NMR chart is shown in FIG. In the present invention, the organic compound represented by the above structural formula (102) is an embodiment of the present invention. 2)-4mDBtPBfpm was obtained.

[0283] 1 H-NMR.δ(CDCl3):7.50-7.7.57(m,4H), 7.64-7 .67(m,2H), 7.82(t,1H), 7.86-8.00(m,9H), 8.0 5-8.09(m,2H), 8.14(d,1H), 8.22-8.26(m,5H), 8.69(s,1H), 8.74(d,1H), 9.07(s,1H), 9.35(s, 1H).

[0284] ≪Physical properties of 8(βN2)-4mDBtPBfpm≫ Next, the ultraviolet-visible absorption spectra (hereinafter simply referred to as "absorption spectra") and emission spectra of the toluene solution and solid thin film of 8(βN2)-4mDBtPBfpm were measured.

[0285] For the measurement of the absorption spectrum in the toluene solution, an ultraviolet-visible spectrophotometer (model V550, manufactured by JASCO Corporation) was used. Also, for the measurement of the emission spectrum in the toluene solution, a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.) was used. The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Fig. 13(A). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. From Fig. 13(A), the toluene solution of 8(βN2)-4mDBtPBfpm shows absorption peaks near 333 nm,

[0286] 325 nm, and 280 nm, and the peak of the emission wavelength is 414 nm ( excitation wavelength 329 nm). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0287] For the measurement of the absorption spectrum of the solid thin film, a solid thin film prepared by vacuum evaporation on a quartz substrate was used, and measured using an ultraviolet-visible spectrophotometer (U4100 type, manufactured by Hitachi High-Technologies Corporation). Also, for the measurement of the emission spectrum of the solid thin film, the same solid thin film as above was used, and measured using a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.). The measurement results of the absorption spectrum and emission spectrum of the obtained solid thin film are shown in Fig. 13(B). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. Also, using the same solid thin film as above, a microscopic PL device La bRAM HR-PL (manufactured by Horiba, Ltd.) was used. The measurement temperature was 10 K, and a He-Cd laser with a wavelength of 325 nm was used as the excitation light. A CCD detector was used as the detector to measure the emission spectrum at low temperature (1 0 K). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. Also, using the same solid thin film as above, a microscopic PL device La bRAM HR-PL (manufactured by Horiba, Ltd.) was used. The measurement temperature was 10 K, and a He-Cd laser with a wavelength of 325 nm was used as the excitation light. A CCD detector was used as the detector to measure the emission spectrum at low temperature (1 0 K).

[0288] From Fig. 13(B), in the solid thin film of 8(βN2)-4mDBtPBfpm, absorption peaks are observed at around 328 nm, 266 nm, and 245 nm, and an emission wavelength peak is observed at around 451 nm (excitation wavelength 340 nm ). Also, from the results of the emission spectrum at low temperature (10 K), the wavelength of the peak (including the shoulder) on the shortest wavelength side of the phosphorescence component of the emission spectrum of 8(βN2)-4mDBtPBfpm was 543 nm. Therefore, from the above peak wavelengths, the T1 level of 8(βN2)-4mDBtPBfpm was calculated to be 2.28 eV.

[0289] The organic compound 8(βN2)-4mDBtPBfpm, which is one aspect of the present invention, has a high T1 level and can be said to be a host material suitable for a phosphorescent material (guest material) that emits light in the vicinity of yellow to red. Note that the organic compound 8(βN2)-4mDBtPBfp m of the present invention can also be used as a host material or a luminescent substance for a phosphorescent luminescent substance in the visible region.

Example

[0290] In this example, as a light-emitting element of one aspect of the present invention, 8-[(2, 2'-binaphthalenyl)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtP Bfpm) (structural formula (102)) described in Example 3 was used as the light-emitting layer in Light-emitting Element 1. For comparison, 4-[3-( dibenzothiophen-4-yl)phenyl]-8-(naphthalen-2-yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8βN-4mDBtPBfpm) (structural formula ([[]] )) was used. Comparative light-emitting device 2 using 301)) in the light-emitting layer. For comparative light-emitting device 3 using 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8 mDBtP2Bfpm) (structural formula (302)) in the light-emitting layer, the device structure, manufacturing method, and its characteristics will be described. The device structure of the light-emitting device used in this example is shown in Fig. 14, and the specific configuration is shown in Table 1. Also, the chemical formulas of the materials used in this example are shown below. Regarding the element structure, manufacturing method, and its characteristics. The element structure of the light-emitting device used in this example is shown in Fig. 14, and the specific configuration is shown in Table 1. Also, the chemical formulas of the materials used in this example are shown below.

[0291]

Table 1

[0292]

Chemical formula

[0293] ≪Fabrication of light-emitting device≫ The light-emitting device shown in this example has a structure in which a hole injection layer 911, a hole transport layer 912, a light-emitting layer 913, an electron transport layer 914, and an electron injection layer 915 are sequentially laminated on a first electrode 901 formed on a substrate 900 as shown in Fig. 14, and a second electrode 903 is laminated on the electron injection layer 915. First, a first electrode 901 was formed on the substrate 900. The electrode area was 4 mm

[0294] (2 mm × 2 2 mm). A glass substrate was used for the substrate 900. The first electrode 901 was formed by sputtering indium tin oxide (ITSO) containing silicon oxide to a film thickness of 70 nm.

[0295] Here, as a pretreatment, the surface of the substrate was washed with water, baked at 200 °C for 1 hour, and then UV o​​​​​​​​ Zone treatment was performed for 370 seconds. Then, 10 -4 The substrate was introduced into a vacuum evaporation apparatus whose interior was depressurized to about 10 Pa, and in a heating chamber within the vacuum evaporation apparatus, vacuum baking was carried out at 170 °C for 30 minutes, and then the substrate was allowed to cool for about 30 minutes.

[0296] Next, a hole injection layer 911 was formed on the first electrode 901. The hole injection layer 911 was formed by co-evaporating 1,3,5-tris(dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II) and molybdenum oxide in a vacuum evaporation apparatus after depressurizing the interior to 10 Pa, with a mass ratio of DBT3P-II:molybdenum oxide of 2:1 and a film thickness of 60 nm. -4 Pa, and then 1,3,5-tris(dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II) and molybdenum oxide were co-evaporated so that the mass ratio of DBT3P-II:molybdenum oxide was 2:1 and the film thickness became 60 nm. benzene (abbreviation: DBT3P-II) and molybdenum oxide, with DBT3P-II:molybdenum oxide = 2:1 (mass ratio), and formed by co-evaporation so that the film thickness was 60 nm. formed.

[0297] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 was formed by evaporating 4,4 '-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenyl amine (abbreviation: PCBBi1BP) so that the film thickness was 20 nm. formed.

[0298] Next, a light-emitting layer 913 was formed on the hole transport layer 912.

[0299] In the case of the light-emitting element 1, the light-emitting layer 913, in addition to 8(βN2)-4mDBtPBfpm and N- (1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole -3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: P CBBiF), as a guest material (phosphorescent light-emitting material), bis[4,6-dimethyl- 2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2 O, (O’) iridium(III) (abbreviation: [Ir(dmpqn)2(acac)]) was used, with a weight ratio of 8(βN2)-4mDBtPBfpm:PCBBiF:[Ir(dmpqn)2 (acac)] = 0.75:0.25:0.1, they were co-evaporated. The film thickness was set to 40 nm. In the case of Comparative Light-Emitting Element 2, in addition to 8βN-4mDBtPBfpm and PCBBiF, as a guest material (phosphorescent light-emitting material), [Ir(dmpqn)2( acac)] was used, and they were co-evaporated with a weight ratio of 8βN-4mDBtPBfpm:PCBBiF:[Ir( dmpqn)2(acac)] = 0.75:0.25:0.1. The film thickness was set to 40 nm. In the case of Comparative Light-Emitting Element 3, in addition to 4,8mDBtP2B fpm and PCBBiF, as a guest material (phosphorescent light-emitting material), [Ir(dm pqn)2(acac)] was used, and they were co-evaporated with a weight ratio of 4,8mDBtP2Bfpm:PCBBiF :[Ir(dmpqn)2(acac)] = 0.75:0.25:0.1. The film thickness was set to 40 nm.

[0300] Next, an electron transport layer 914 was formed on the light-emitting layer 913.

[0301] In the case of Light-Emitting Element 1, for the electron transport layer 914, the film thickness of 8(βN2)-4mDBtPBfpm was 25 nm, and the film thickness of 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10- phenanthroline (abbreviation: NBphen) was 15 nm, and they were sequentially evaporated to form it. In the case of Comparative Light-Emitting Element 2, the film thickness of 8βN-4mDBtPBfpm was 25 n m, and the film thickness of NBphen was 15 nm, and they were sequentially evaporated to form it. Also, for the comparative light-emitting In the case of the element 3, it was formed by sequentially depositing a film of 4,8 mDBtP2Bfpmm with a thickness of 25 nm and a film of NBphen with a thickness of 15 nm.

[0302] Next, an electron injection layer 915 was formed on the electron transport layer 914. The electron injection layer 915 was formed by depositing lithium fluoride (LiF) to a thickness of 1 nm.

[0303] Next, a second electrode 903 was formed on the electron injection layer 915. The second electrode 903 was formed by depositing aluminum by vapor deposition to a thickness of 200 nm. In this embodiment, the second electrode 903 functions as a cathode.

[0304] Through the above steps, a light-emitting element was formed on the substrate 900 with an EL layer 902 sandwiched between a pair of electrodes. Note that the hole injection layer 911, the hole transport layer 912, the light-emitting layer 91 3, the electron transport layer 914, and the electron injection layer 915 described in the above steps are functional layers that constitute the EL layer in one aspect of the present invention. Also, in the vapor deposition process in the manufacturing method described above, all vapor depositions were performed by the resistance heating method.

[0305] In addition, the light-emitting element manufactured as described above is sealed with another substrate (not shown). Note that when sealing with another substrate (not shown), in a glove box under a nitrogen atmosphere, a another substrate (not shown) coated with a sealant that is cured by ultraviolet light was fixed on the substrate 900, and the substrates were adhered to each other so that the sealant adhered to the periphery of the light-emitting element formed on the substrate 900. At the time of sealing, ultraviolet light of 365 nm was irradiated at 6 J / cm 2 to cure the sealant, and the sealant was stabilized by heat treatment at 8 0 °C for 1 hour.

[0306] ​ ≪Operating Characteristics of Light-Emitting Element≫ The operating characteristics of each fabricated light-emitting element were measured. The measurement was carried out at room temperature (maintained at 25 °C atmosphere). Also, as a result of the operating characteristics of each light-emitting element, the current density-luminance characteristics are shown in Fig. 1 5, the voltage-luminance characteristics are shown in Fig. 16, the luminance-current efficiency characteristics are shown in Fig. 17, and the voltage-current characteristics are shown in Fig. 18 respectively.

[0307] Also, the main initial characteristic values of each light-emitting element near 1000 cd / m 2 are shown in Table 2 below. .

[0308]

Table 2

[0309] Also, the emission spectra of the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3 when a current was passed at a current density of 2.5 mA / cm 2 are shown in Fig. 19. As shown in Fig. 19, the emission spectra of the light-emitting element 1 , the comparative light-emitting element 2, and the comparative light-emitting element 3 have a peak near 626 nm , and it is suggested that they all originate from the emission of [Ir(dmpqn)2(acac) contained in the light-emitting layer 913. .

[0310] Next, reliability tests were conducted on the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3 . The results of the reliability test are shown in Fig. 20. In Fig. 20, the vertical axis indicates the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis indicates the driving time (h) of the element. The reliability test was a constant current drive test in which a constant current was passed at a current density of 75 mA / cm . 2

[0311] From the results of the reliability test, it was found that the light-emitting element 1 has less deterioration at the initial stage of driving compared to the comparative light-emitting element 2 and the comparative light-emitting element 3. Using the organic compound, 8(( βN2)-4mDBtPBfpm (structural formula (102)), which is one aspect of the present invention, can be said to be useful for improving the element characteristics of the light-emitting element. Note that 8βN-4mD BtPBfpm (structural formula (301)) used for the comparative light-emitting element 2 has a structure in which a naphthyl group is bonded to the 8-position of the benzofuropyrimidine skeleton, and 4,8mDBtP2Bfpm (structural formula ( 302)) used for the comparative light-emitting element 3 has a structure in which dibenzothiophene is bonded to the 8-position of the benzofuropyrimidine skeleton via a phenyl group. However, 8((βN2)-4mDBtPBfpm used for the light-emitting element 1 has a structure in which a plurality of arylene groups are linked to the 8-position of the benzofuropyrimidine skeleton. Specifically, it has a molecular structure having a binaphthyl group in which two identical naphthyl groups are linked. Therefore, by using an organic compound having a structure in which a biarylene group is present at the 8-position of a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton, such as the organic compound which is one aspect of the present invention, in a light-emitting element, the time (LT95) when the initial luminance of the light-emitting element 1 decreases by 5% is 173 hours, whereas the LT95 of the comparative light-emitting element 2 is 86 hours and the LT95 of the comparative light-emitting element 3 is 32 hours. It can be said that it is effective in suppressing the initial deterioration of the light-emitting element and can provide a highly reliable light-emitting element.

[0312]

[0313]

Example

[0313] In this example, as the light-emitting element which is one aspect of the present invention, a light-emitting element 4 using 8BP-4m DBtPBfpm (structural formula (100)) described in Example 1 in the light-emitting layer, and a light-emitting element described in Example 2 ​The light-emitting device 5 using 8mBP-4mDBtPBfpm (structural formula (101)) in the light-emitting layer, As a comparison, the comparative light-emitting device 6 using 8Ph-4mDBtPBfpm (structural formula (300)) in the light-emitting layer, As a comparison, the comparative light-emitting device 7 using 8DBt-4mDBtPBfpm (structural formula (303)) in the light-emitting layer, were fabricated, and the measurement results of their characteristics are shown.

[0314] Note that the device structures of the light-emitting device 4, the light-emitting device 5, the comparative light-emitting device 6, and the comparative light-emitting device 7 fabricated in this example are the same as those shown in FIG. 14 in Example 4, but the specific configurations of the respective layers constituting the device structure are as shown in Table 3. In addition, the chemical formulas of the materials used in this example are shown below.

[0315]

Table 3

[0316]

Chemical formula

[0317] ≪Operating characteristics of each light-emitting device≫ The operating characteristics of the fabricated light-emitting device 4, the light-emitting device 5, the comparative light-emitting device 6, and the comparative light-emitting device 7 were measured. The measurement was performed at room temperature (atmosphere maintained at 25°C).

[0318] The current density-luminance characteristics of each light-emitting device are shown in FIG. 21, the voltage-luminance characteristics are shown in FIG. 22, the luminance-current efficiency characteristics are shown in FIG. 23, and the voltage-current characteristics are shown in FIG. 24, respectively.

[0319] Also, the main initial characteristic values of each light-emitting device near 1000 cd / m 2 are shown in Table 4 below.

[0320] ​​​​​​​ [Table 4]

[0321] In addition, each light-emitting element is supplied with 2.5mA / cm 2 The emission spectrum when a current is applied at a current density of As shown in FIG. 25, the emission spectrum of each light-emitting element has a peak at around 560 nm. The peak is the peak of [Ir(ppy)2(4dppy)] contained in the light-emitting layer 913. This suggests that it is due to luminescence.

[0322] Next, a reliability test was performed on each light-emitting element. The results of the reliability test are shown in FIG. In 6, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test is performed at 50mA / cm 2 At a constant current density A constant current drive test was carried out.

[0323] From the results of the reliability test, the organic compound according to one embodiment of the present invention, 8BP-4mDBtPBfp The light-emitting element 4 using m (structural formula (100)) in the light-emitting layer had a time required for the luminance to decrease by 5% from the initial luminance. (LT95) was 131 hours, and 8mBP-4mDBtPBfpm (structural formula (101) The light-emitting device 5 using the organic compound 8) in the light-emitting layer had a LT95 of 112 hours. Comparative light-emitting element 6, which uses Ph-4mDBtPBfpm (structural formula (300)) in the light-emitting layer, The LT95 was 98 hours, and 8DBt-4mDBtPBfpm (structural formula (303)) was produced. The comparative light-emitting element 7 used in the optical layer had a LT95 of 62 hours, and The initial deterioration of a light-emitting element using the material for a light-emitting layer was suppressed. The organic compounds, 8BP-4mDBtPBfpm and 8mBP-4mDBtPBfpm have a structure in which a plurality of arylene groups are linked to the 8-position of the benzofuropyrimidine skeleton, more preferably due to the effect of having a biphenyl group to which two identical phenyl groups are linked. Therefore, using the organic compound which is one aspect of the present invention is useful for improving the reliability of the light-emitting device and it can be said that.

Examples

[0324] In this example, as the light-emitting device which is one aspect of the present invention, a light-emitting device 8 using 8BP-4mD BtPBfpm (structural formula (100)) described in Example 1 in the light-emitting layer, a light-emitting device 9 using 8mBP-4mDBtPBfpm (structural formula (101)) described in Example 2 in the light-emitting layer, for comparison a comparative light-emitting device 10 using 8Ph-4mDBtPBfpm (structural formula (300)) in the light-emitting layer, and for comparison a comparative light-emitting device 11 using 8DBt-4mDBtPBfpm (structural formula (303)) in the light-emitting layer were fabricated, and the results of measuring their characteristics are shown.

[0325] Note that the device structures of the light-emitting device 8, the light-emitting device 9, the comparative light-emitting device 10, and the comparative light-emitting device 11 fabricated in this example are the same as those shown in FIG. 14 in Example 4, but the specific configurations of the respective layers constituting the device structure are as shown in Table 5. Also, the chemical formulas of the materials used in this example are shown below.

[0326]

Table 5

[0327]

Chemical formula

[0328] ≪Operating Characteristics of Each Light-Emitting Element≫ The operating characteristics of the fabricated light-emitting elements 8 and 9, comparative light-emitting element 10, and comparative light-emitting element 11 were measured. The measurement was performed at room temperature (in an atmosphere maintained at 25°C).

[0329] The current density-luminance characteristics, voltage-luminance characteristics, luminance-current efficiency characteristics, and voltage-current characteristics of each light-emitting element are shown in FIGS. 27, 28, 29, and 30, respectively.

[0330] Also, the main initial characteristic values of each light-emitting element near 1000 cd / m 2 are shown in Table 6 below.

[0331]

Table 6

[0332] In addition, the emission spectra of each light-emitting element when a current was passed at a current density of 2.5 mA / cm 2 are shown in FIG. 31. As shown in FIG. 31, the emission spectrum of the light-emitting element has a peak near 524 nm, suggesting that it is derived from the emission of [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κ C]iridium (abbreviation: [Ir(ppy)2(mdppy)]) contained in the light-emitting layer 913.

[0333] Next, a reliability test was performed on each light-emitting element. The results of the reliability test are shown in FIG. 32. In FIG. 3 2, the vertical axis represents the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis represents the driving time (h) of the element. Note that the reliability test was performed at a current density of 50 mA / cm 2 with a constant electric ​​​​​A constant current drive test with a flowing current was conducted.

[0334] From the results of the reliability test, the organic compound, 8BP-4mDBtPBfp m (structural formula (100)) used in the light-emitting element 8 for the light-emitting layer has a time when the luminance decreases by 5% from the initial luminance (LT95) of 30 hours, and 8mBP-4mDBtPBfpm (structural formula (10 1)) used in the light-emitting element 9 for the light-emitting layer has an LT95 of 28 hours. For the comparative organic compound, the comparative light-emitting element 1 1 using 8DBt-4mDBtPBfpm (structural formula (303)) in the light-emitting layer has an LT95 of 15 hours, and the initial deterioration of the organic compound which is one aspect of the present invention was suppressed Also, for the comparative light-emitting element 10 using the comparative organic compound, 8Ph-4mDBtPBfpm (structural formula (300) ) in the light-emitting layer, although the LT95 is 29 hours which is good, the slope of the long-term deterioration was steeper than that of the organic compound which is one aspect of the present invention. These are due to the effect of the organic compound which is one aspect of the present invention, 8BP-4mDBtPBfp and 8mBP-4mDBtP Bfpm having a structure in which a plurality of arylene groups are linked at the 8-position of the benzofuropyrimidine skeleton, more preferably a biphenyl group having two linked identical phenyl groups. Therefore, it can be said that using the organic compound which is one aspect of the present invention is useful for improving the reliability of the light-emitting element.

[0335] ≪Reference Synthesis Example 1≫ In this reference synthesis example, the organic compound represented by the following structural formula used in the comparative light-emitting element 6 of Example 5 and the comparative light-emitting element 10 of Example 6, 4-[3-(dibenzothiophen-4-yl) phenyl]-8-phenyl-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8Ph- ​Specific examples of the synthesis of 4mDBtPBfpm) (structural formula (300)) are illustrated.

[0336]

Chemical formula

[0337] <Synthesis of 8Ph-4mDBtPBfpm> 8-Chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzof uro[3,2-d]pyrimidine 3.00 g, phenylboronic acid 0.95 g, tripotassium phosphate 4.12 g, diglyme 65 mL, and t-butanol 1.44 g were placed in a three-necked flask, and the flask was degassed by stirring under reduced pressure and purged with nitrogen. To this mixture, palladium(II) acetate 42.7 mg and di(1-adamantyl)-n-butylphosphine 140 mg were added , and the mixture was stirred at 120 °C for 15.5 hours.

[0338] To this reaction solution, palladium(II) acetate 45.2 mg and di(1-adamantyl)-n-butyl phosphine 140 mg were added, and the mixture was stirred at 120 °C for 6 hours and then at 140 °C for 3 hours. Water was added to this reaction solution, and the mixture was suction filtered. The obtained residue was washed with ethyl acetate and hexane . This residue was dissolved in hot toluene and passed through a filter aid filled with celite, alumina, and celite in that order. The obtained solution was concentrated to dryness and recrystallized from toluene to obtain a white solid containing the target product in a yield of 1.50 g. 1.50 g of the obtained white solid was sublimation-purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 3.48 Pa, while flowing argon gas at a flow rate of 15 mL / min, the solid was heated at 28

[0339] 0 °C. After sublimation purification, the target product was obtained (1.02 g of white solid, recovery rate 68%). 0 °C while flowing argon gas at a flow rate of 15 mL / min. After sublimation purification, the target product was obtained (1.02 g of white solid, recovery rate 68%). 0 °C while flowing argon gas at a flow rate of 15 mL / min. After sublimation purification, the target product was obtained (1.02 g of white solid, recovery rate 68%). )。The synthesis scheme is shown in the following formula (d-1).

[0340] [Chemical formula]

[0341] Note that the analysis results of the white solid obtained above by nuclear magnetic resonance spectroscopy ( 1 1H-NMR) are shown below . From this, it was found that 8Ph-4mDBtPBfpm was obtained.

[0342] 1 1H-NMR. δ(CDCl3): 7.42 (t, 1H), 7.49 - 7.53 (m, 4 H), 7.64 - 7.66 (m, 2H), 7.71 (d, 2H), 7.79 - 7.82 ( m, 2H), 7.87 (d, 1H), 7.97 (t, 2H), 8.23 - 8.25 (m, 2H), 8.52 (s, 1H), 8.72 (d, 1H), 9.05 (s, 1H), 9.3 3 (s, 1H).

[0343] <<Reference Synthesis Example 2>> In this reference synthesis example, the organic compound represented by the following structural formula used in Comparative Light Emitting Element 2 of Example 4 , 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalen-2-yl yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8βN-4mDBtPBfp m) (structural formula (301)) is specifically exemplified as a synthesis example.

[0344] [Chemical formula]

[0345] <Synthesis of 8βN-4mDBtPBfpm> First, 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]ben 1.5 g of enzofuro[3,2-d]pyrimidine, 0.73 g of 2-naphthalene boronic acid, 1.5 g of cesium fluoride and 32 mL of mesitylene were added, and the inside of a 100 mL three-necked flask was purged with nitrogen, and 70 mg of 2'-(dicyclohexylphosphino)acetophenone ethylene ketal and 89 mg of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) were added, and the mixture was heated at 120 °C for 5 hours under a nitrogen stream. The resulting reaction product was added with water and filtered, and the filtrate was washed successively with water and ethanol.

[0346] This filtrate was dissolved in toluene and filtered using a filter aid filled with celite, alumina, and celite in that order. The solvent of the resulting solution was concentrated and recrystallized to obtain 1.5 g of a pale yellow solid of the target product in a yield of 64%. The synthetic scheme is shown in the following formula (e-1).

[0347]

Chemical formula

[0348] 1.5 g of the obtained pale yellow solid was purified by sublimation using the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.0 Pa, while flowing argon gas at a flow rate of 10 mL / min, the solid was heated at 290 °C. After sublimation purification, 0.60 g of a yellow solid of the target product was obtained in a recovery rate of 39%.

[0349] The analysis results of the obtained yellow solid by nuclear magnetic resonance spectroscopy ( 1 1H-NMR) are shown below. From these results, it was found that 8βN-4mDBtPBfpm was obtained.

[0350] 1H-NMR. δ (TCE-d2): 7.45 - 7.50 (m, 4H), 7.57 - 7. 62 (m, 2H), 7.72 - 7.93 (m, 8H), 8.03 (d, 1H), 8.10 (s, 1H), 8.17 (d, 2H), 8.60 (s, 1H), 8.66 (d, 1H), 8.98 (s, 1H), 9.28 (s, 1H).

Example

[0351] ≪Synthesis Example 4≫ In this example, an organic compound which is an aspect of the present invention represented by the structural formula (103) of Embodiment 1, 8-(1,1'-biphenyl-4-yl)-4-[3'-(dibenzothiophene- 4-yl)biphenyl-3-yl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation : 8BP-4mDBtBPBfpm) will be described about its synthesis method. Incidentally, the structure of 8BP-4m DBtBPBfpm is shown below.

[0352]

Chemical Formula

[0353] <Synthesis of 8BP-4mDBtBPBfpm> 2.26 g of 8-chloro-4-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]- [1]benzofuro[3,2-d]pyrimidine, 0.9 15 g of 4-biphenylboronic acid, 1.27 g of cesium fluoride, and 42 mL of mesitylene were placed in a three-necked flask, degassed by stirring under reduced pressure, and purged with nitrogen. This mixture was heated to 60 °C, and 0.116 g of tris(dibenzylideneacetone)dipalladium(0) and 90.2 mg of 2'-(dicyclohexylphosphino)acetophenone ethylene ketal were added, and heated at 100 °C for 13.5 hours ​​​​Then, it was stirred at 120 °C for 7.5 hours. To this mixture, 0.115 g of tris(dibenzylideneacetone)dipalladium(0) and 90.3 mg of 2'-(dicyclohexylphosphino)acetophenone ethylene ketal were added, and the mixture was stirred at 120 °C for 28 hours. Water was added to this reaction solution, and suction filtration was performed. The obtained filtrate was washed with water, ethanol, and toluene. The filtrate was dissolved in hot toluene and passed through a filter aid filled with celite, alumina, and celite in that order. The obtained solution was concentrated to dryness and recrystallized from toluene to obtain 1.93 g of the target pale yellow solid in a yield of 70%. 1.93 g of the obtained pale yellow solid was sublimation-purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.35 Pa, while flowing argon gas at a flow rate of 10 mL / min, the solid was heated at 355 °C. After sublimation purification, 1.66 g of the target pale yellow solid was obtained in a recovery rate of 86%. This synthesis scheme is shown in the following formula (f-1). Note that the analysis results of the white solid obtained in the above reaction by nuclear magnetic resonance spectroscopy ( 1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 33. From these results, in this example, it was found that the organic compound 8BP-4mDBtBPBfpm, which is one aspect of the present invention represented by the above structural formula (103), was obtained. is shown in the following formula (f-1).

[0354]

Chemical formula

[0355] In addition, the analysis results of the white solid obtained in the above reaction by nuclear magnetic resonance spectroscopy ( 1 1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 33. From these results, in this example, 1 it was found that the organic compound 8BP-4mDBtBPBfpm, which is one aspect of the present invention represented by the above structural formula (103), was obtained. In this example, the organic compound, 8BP-4mDBtBPBfpm, which is one aspect of the present invention represented by the above structural formula (103), was obtained. was found.

[0356] 1 1H-NMR.δ(CDCl3): 7.37 - 7.40 (m, 1H), 7.46 - 7.5 2(m, 4H), 7.60 - 7.85(m, 14H), 7.92 - 7.98(m, 2H) , 8.19 - 8.23(m, 3H), 8.57(m, 1H), 8.64 - 8.66(m, 1H), 8.98 - 8.99(m, 1H), 9.33(s, 1H).

[0357] ≪Properties of 8BP - 4mDBtBPBfpm≫ Next, the ultraviolet - visible absorption spectra and emission spectra of the toluene solution and solid thin film of 8BP - 4mDBtBPBfpm were measured. (Hereinafter, simply referred to as "absorption spectrum").

[0358] For the measurement of the absorption spectrum in the toluene solution, an ultraviolet - visible spectrophotometer (model V550, manufactured by JASCO Corporation) was used. Also, for the measurement of the emission spectrum in the toluene solution, a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.) was used. The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Fig. 34. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0359] From Fig. 34, the toluene solution of 8BP - 4mDBtBPBfpm shows absorption peaks around 332 nm, 316 nm and 281 nm, and the peak of the emission wavelength is 406 nm (excitation wavelength 3 18 nm).

[0360] For the measurement of the absorption spectrum of the solid thin film, a solid thin film prepared by vacuum evaporation on a quartz substrate was used, and measured using an ultraviolet - visible spectrophotometer (U4100 type, manufactured by Hitachi High - Technologies Corporation). Also, for the measurement of the emission spectrum of the solid thin film, the same solid thin film as above was used, and measured using a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.). The absorption The measurement results of the spectrum and emission spectrum are shown in Fig. 35. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0361] From Fig. 35, in the solid thin film of 8BP-4mDBtBPBfpm, absorption peaks were observed near 340 nm, 310 nm , 290 nm, 270 nm, and 245 nm, and an emission wavelength peak was observed near 426 nm (excitation wavelength 330 nm).

Example

[0362] ≪Synthesis Example 5≫ In this example, a method for synthesizing an organic compound, which is an aspect of the present invention represented by the structural formula (105) of Embodiment 1, 8-[(2,2'-binaphthalen)-6-yl]-4-[3'-(dibenzothiophene -4-yl)biphenyl-3-yl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtBPBfpm) will be described. Incidentally, the structure of 8(βN2)-4mDBtBPBfpm) is shown below.

[0363]

Chemical formula

[0364] <Synthesis of 8(βN2)-4mDBtBPBfpm> 2.11 g of 8-chloro-4-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]- [1]benzofuro[3,2-d]pyrimidine, 1.26 g of [2,2'-binaphthalene]- 6-ylboronic acid, 2.55 g of tripotassium phosphate, 40 mL of diglyme, and 0.93 g of t-butyl anol were placed in a three-necked flask, and the inside of the flask was degassed by stirring under reduced pressure and substituted with nitrogen. This mixture was heated to 60 °C, and 27.0 mg of palladium(II) acetate, di (1-Adamantyl)-n-butylphosphine 77.8 mg was added, and the mixture was stirred at 120 °C for 14 hours. Palladium(II) acetate 27.5 mg and di(1-adamantyl)-n-butyl phosphine 76.4 mg were added, and the mixture was stirred at 120 °C for 16 hours. Further, palladium(II) acetate 27.6 mg and di(1-adamantyl)-n-butylphosphine 77 .9 mg were added to this reaction mixture, and the mixture was stirred at 120 °C for 14.5 hours and then at 130 °C for 6.5 hours.

[0365] Water was added to this reaction mixture, and the mixture was suction filtered. The obtained filtrate was washed with water and toluene. This filtrate was dissolved in hot toluene and passed through a filtration aid filled with celite, alumina, and celite in that order. The obtained solution was concentrated to dryness and recrystallized from toluene to obtain 1.56 g of a white solid as the target product in a yield of 52%.

[0366] 1.15 g of this white solid was purified by sublimation using the train sublimation method. The sublimation purification conditions were as follows: while flowing argon gas at a flow rate of 10 mL / min, the pressure was 2.33 Pa, and the solid was heated at 375 °C. After sublimation purification, 1.06 g of a pale yellow solid as the target product was obtained in a recovery rate of 92%. This synthetic scheme is shown in the following formula (g-1).

[0367]

Chemical formula

[0368] Note that the analysis results 1 by nuclear magnetic resonance spectroscopy ( 1H-NMR) of the white solid obtained in the above reaction are shown below. Also, 1 the 1H-NMR chart is shown in Fig. 36. From these results, in this example, the organic compound, 8(βN, which is one aspect of the present invention represented by the above structural formula (105), 2) It was found that 2-4mDBtBPBfpm was obtained.

[0369] 1 H-NMR, δ(CDCl3): 7.46 - 7.57 (m, 4H), 7.62 - 7.6 3 (m, 2H), 7.70 (t, 1H), 7.75 - 7.87 (m, 5H), 7.90 - 8.00 (m, 7H), 8.06 - 8.10 (m, 3H), 8.20 - 8.24 (m, 6 H), 8.66 - 8.68 (m, 2H), 9.00 (s, 1H), 9.34 (s, 1H) .

[0370] <<Regarding the physical properties of 8(βN2)-4mDBtBPBfpm>> Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum of the solid thin film of 8(βN2)-4mDBtBPBfpm were measured.

[0371] For the measurement of the absorption spectrum of the solid thin film, a solid thin film prepared by vacuum evaporation on a quartz substrate was used, and measured using an ultraviolet-visible spectrophotometer (U4100 type manufactured by Hitachi High-Technologies). Also, for the measurement of the emission spectrum of the solid thin film, the same solid thin film as above was used, and measured using a fluorescence photometer ((FS920 manufactured by Hamamatsu Photonics K.K.)). The measurement results of the absorption spectrum and the emission spectrum of the obtained solid thin film are shown in Fig. 37. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity.

[0372] From Fig. 37, in the solid thin film of 8(βN2)-4mDBtBPBfpm, absorption peaks were observed near 328 nm, 29 0 nm, 267 nm, and 246 nm, and a peak of the emission wavelength was observed near 446 nm (excitation wavelength 3 30 nm).

Example

[0373] <Synthesis Example 6> In this example, an organic compound represented by structural formula (126) in Embodiment 1, which is one embodiment of the present invention, Compound 8-(1,1':3',1''-terphenyl-4-yl)-4-[3-(diphenyl 1,2-Dimethylbenzo[3,2-d]pyrimidine (abbreviation) The synthesis method of 8pmTP-4mDBtPBfpm is explained below. The structure of P-4mDBtPBfpm is shown below.

[0374] [ka]

[0375] <Step 1: Synthesis of 4-bromo-1,1':3',1''-terphenyl> 3-Biphenylboronic acid 0.50g, 1-bromo-4-iodobenzene 1.06g, carbonic acid Put 0.80 g of sodium, 17 mL of toluene, and 4 mL of ethanol into a flask with sidearm. The flask was degassed by stirring under reduced pressure and replaced with nitrogen. Add 86.7 mg of triphenylphosphine palladium (0) and stir at 120°C for 26 hours. Water was added to the reaction mixture, which was then subjected to suction filtration. The filtrate was concentrated to give a brown solid. The solid was dissolved in a mixture of toluene and ethyl acetate, and silica gel was added to the resulting solution. The concentrate was concentrated. The resulting concentrate was subjected to silica gel column chromatography to remove the eluent from hexane. When purified as a solid, the desired product was obtained as a white solid (0.30 g, 39% yield). The synthesis scheme is shown in formula (h-1) below.

[0376] [ka]

[0377] <Step 2: Synthesis of 1,1’:3’,1’’-Terphenyl-4-boronic acid> 2.94 g of 4-bromo-1,1’:3’,1’’-terphenyl synthesized in Step 1 was placed in a three-necked flask, the inside of the flask was purged with nitrogen, and 53 mL of dehydrated tetrahydrofuran was added and cooled to -78°C. 8.9 mL of n-butyllithium (1.6 M - hexane solution) was slowly added dropwise thereto, and the mixture was stirred at -78°C for 1 hour. Trimethyl borate 1.6 mL was added dropwise to this reaction product, and the mixture was stirred overnight at room temperature. Hydrochloric acid was added to this reaction product, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine and dried over magnesium sulfate was added dropwise thereto, and the mixture was stirred overnight at room temperature. Hydrochloric acid was added to this reaction product, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine and dried over magnesium sulfate and dried. This mixture was filtered naturally, and the filtrate was concentrated to obtain a solid. The obtained solid was washed with a mixed solution of ethyl acetate and hexane to obtain 1.57 g of the target white solid in a yield of 60%. This synthetic scheme is shown in the following formula (h-2). This synthetic scheme is shown in the following formula (h-2).

[0378]

Chemical formula

[0379] <Step 3: Synthesis of 8pmTP-4mDBtPBfpm> 1.12 g of 1,1’:3’,1’’-terphenyl-4-boronic acid synthesized in Step 2 , 1.35 g of 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine, 1.70 g of cesium fluoride, and 26 mL of mesitylene were placed in a three-necked flask, degassed by stirring under reduced pressure, and purged with nitrogen.

[0380] 343 mg of tris(dibenzylideneacetone)dipalladium(0) and di(1 -Adamantyl)-n-butylphosphine 127 mg and 2'-(dicyclohexylphosphino)acetophenone ethylene ketal 126 mg were added, and the mixture was stirred at 120 °C for 43.5 hours. Water was added to the reaction mixture, and the mixture was filtered by suction. The obtained filtrate was washed with water, ethanol, and toluene, dissolved in hot toluene, passed through a filter aid filled in the order of celite, alumina, and celite, concentrated, dried, and recrystallized by a diffusion method using toluene / ethanol as a solvent that separates into two phases to obtain 702 mg of a white solid as the target product, with a yield of 37%.

[0381] Hexane was added to the filtrate obtained by suction filtration of the above-mentioned reaction mixture, and the precipitated solid was filtered by suction, purified by silica gel column chromatography (toluene:ethyl acetate = 50:1), recrystallized with toluene / ethanol, and 0.18 g of a white solid as the target product was obtained with a yield of 9.5%. These target products were mixed, and 633 mg of a white solid was sublimation-purified by the train sublimation method. The sublimation purification conditions were as follows: while flowing argon gas at a flow rate of 10 mL / min under a pressure of 2.52 Pa, the solid was heated at 330 °C. After sublimation purification, 460 mg of a pale yellow solid of the target product was obtained with a recovery rate of 73%. This synthetic scheme is shown in the following formula (h-3).

[0382]

Chemical formula

[0383] In addition, the analysis results of the pale yellow solid obtained in the above reaction by nuclear magnetic resonance spectroscopy ( 1 1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 38. From these results, in this example 1 ​​​In the above, the organic compound represented by the structural formula (126) according to one embodiment of the present invention, 8pm It was found that TP-4mDBtPBfpm was obtained.

[0384] 1 H-NMR.δ(CDCl3):7.40(t,1H), 7.47-7.70(m,1 1H), 7.79-7.89(m,8H), 7.98-8.04(m,2H), 8.24 -8.26(m,2H), 8.59(d,1H), 8.73(d,1H), 9.05(t ,1H), 9.34(s,1H).

[0385] ≪Physical properties of 8pmTP-4mDBtPBfpm≫ Next, the UV-visible absorption spectra of the toluene solution and the solid thin film of 8pmTP-4mDBtPBfpm were The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured.

[0386] The absorption spectrum in toluene solution was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). The emission spectrum in the toluene solution was measured using a fluorometer. The absorption spectrum of the obtained toluene solution was The results of the measurements of the absorption and emission spectra are shown in Figure 39. The horizontal axis is the wavelength, and the vertical axis is the absorption intensity and and luminescence intensity.

[0387] As shown in Figure 39, the toluene solution of 8pmTP-4mDBtPBfpm has a peak at 315 nm and 282 nm. The absorption peak is seen around nm, and the emission wavelength peak is 406 nm (excitation wavelength 310 nm). It was.

[0388] To measure the absorption spectrum of a solid thin film, a solid thin film was prepared by vacuum deposition on a quartz substrate. Using an ultraviolet-visible spectrophotometer (U4100 type manufactured by Hitachi High-Technologies Corporation), measurements were taken. For the measurement of the emission spectrum of the solid thin film, using the same solid thin film as above, a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics K.K.) was used for measurement. The absorption spectrum and emission spectrum measurement results of the obtained solid thin film are shown in Fig. 40. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0389] From Fig. 40, in the solid thin film of 8BP-4mDBtBPBfpm, absorption peaks were observed near 340 nm, 310 nm , 288 nm, 270 nm, and 243 nm, and an emission wavelength peak was observed near 426 nm (excitation wavelength 330 nm).

Example

[0390] ≪Synthesis Example 7≫ In this example, a method for synthesizing an organic compound, which is an aspect of the present invention represented by the structural formula (128) of Embodiment 1, 8-(1,1’:4’,1’’-terphenyl-3-yl)-4-[3-(dibenzo thiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation : 8mpTP-4mDBtPBfpm), will be described. The structure of 8mpT P-4mDBtPBfpm is shown below.

[0391]

Chemical formula

[0392] <Step 1: Synthesis of 2-hydroxy-5-(1,1’:4’,1’’-terphenyl-3-yl)benzonitrile> 6.98 g of 5-bromo-2-hydroxybenzonitrile, β-[1,1’:4’,1’’ -Terphenyl]-3-ylboronic acid 10.9 g, potassium carbonate 11.0 g, toluene 3 70 mL, ethanol 40 mL, and water 40 mL were placed in a three-necked flask and stirred under reduced pressure to degas and then purged with nitrogen. To this mixture, 467 mg of palladium(II) acetate and 1.34 g of tris(2 -methylphenyl)phosphine were added, and the mixture was stirred at 80 °C for 4.0 hours. Water was added to this reaction product, and the mixture was suction filtered. The resulting filter cake was washed with water, ethanol, toluene, and ethyl acetate to obtain 12.0 g of the desired gray solid in a yield of 98%. This synthetic scheme is shown in the following formula (i-1).

[0393]

Chemical formula

[0394] <Step 2: Synthesis of ethyl 3-amino-5-(1,1’:4’,1’’-terphenyl-3-yl) benzo[b]furan-2-carboxylate> Next, 12.0 g of 2-hydroxy-5-(1,1’:4’,1’’-terphenyl-3-yl)benzonitrile synthesized in Step 1, 7.05 g of ethyl bromoacetate, 9.64 g of potassium carbonate, and 90 mL of dimethylformamide were placed in a three-necked flask. This mixture was stirred at 1 00 °C for 7.0 hours. Water was added to this reaction solution, and the mixture was suction filtered. The resulting filter cake was washed with water and ethanol. This filter cake was dissolved in hot ethyl acetate and suction filtered. The resulting solution was concentrated to obtain 11.9 g of the desired gray solid in a yield of 79%. This synthetic scheme is shown in the following formula (i-2).

[0395]

Chemical formula

[0396] <Step 3: Synthesis of 8-(1,1’:4’,1’’-terphenyl-3-yl)[1]benzofuro[3,2-d]pyrimidin-4(3H)-one> > Next, 11.9 g of ethyl 3-amino-5-(1,1’:4’,1’’-terphenyl-3-yl)benzofuran-2-carboxylate synthesized in Step 2, 5.81 g of formamidine acetate, and 120 mL of formamide were placed in a three-necked flask. This mixture was stirred at 160 °C for 12.0 hours. Water was added to the reaction solution and suction filtration was performed. The obtained filtrate was washed with water and ethanol, and the target brown solid was obtained in a yield of 10.6 g and a yield of 93%. This synthesis scheme is shown in the following formula (i-3).

[0397] [Chemical formula]

[0398] <Step 4: Synthesis of 4-chloro-8-(1,1’:4’,1’’-terphenyl-3-yl) [1]benzofuro[3,2-d]pyrimidine> Next, 10.6 g of 8-(1,1’:4’,1’’-terphenyl-3-yl) [1]benzofuro[3,2-d]pyrimidin-4(3H)-one synthesized in Step 3, 40 mL of phosphorus oxychloride, and 0.02 mL of dimethylformamide were placed in a three-necked flask. This mixture was stirred at 90 °C for 12.0 hours under a nitrogen stream. The obtained reaction product was placed in ice water, and this solution was neutralized with sodium hydroxide and then saturated sodium bicarbonate water and stirred for 1 hour. This mixture was suction filtered, and the filtrate was dissolved in hot toluene and passed through a filter aid filled with celite, alumina, and celite in that order. The obtained solution was concentrated, and toluene was used as a solvent for separating into two phases. ​​​Recrystallization was carried out by the diffusion method using EtOH, and the target yellow solid was obtained in a yield of 8. 99 g and a yield of 81%. This synthetic scheme is shown in the following formula (i-4).

[0399]

Chemical formula

[0400] <Step 5: Synthesis of 8-(1,1’:4’,1’’-terphenyl-3-yl)-4-[3- (dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine > Next, 1.98 g of 4-chloro-8-(1,1’:4’,1’’-terphenyl-3-yl)[1]benzofuro[3,2-d]pyrimidine obtained in Step 4, 1.69 g of 3-(dibenzothiophen-4-yl)phenylboronic acid, 1.64 g of potassium carbonate, 45 mL of toluene, 5.0 mL of ethanol and 5.0 mL of water were placed in a three-necked flask, stirred under reduced pressure to degas and replace with nitrogen.

[0401] 407 mg of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2) was added to this mixture and stirred at 90 °C for 9.0 hours. Water was added to the resulting reaction product and suction filtered. The obtained filtrate was washed with water, ethanol and toluene, dissolved in hot toluene and passed through a filter aid filled in the order of celite, alumina, celite. The obtained solution was concentrated to dryness and recrystallized by the diffusion method using toluene / ethanol as a solvent for two-phase separation, and the target white solid was obtained in a yield of 2.57 g and a yield of 8 5%.

[0402] ​​2.30 g of this white solid was purified by sublimation using the train sublimation method. Sublimation purification conditions were as follows: while flowing argon gas at a flow rate of 15 mL / min under a pressure of 2.5 Pa, the solid was heated at 350 °C . After sublimation purification, 8-(1,1’:4’,1’’-terphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine, the target product, was obtained in a yield of 1.69 g (recovery rate 74%, white solid). This synthetic scheme is shown in the following formula (i-5).

[0403]

Chemical formula

[0404] In addition, the analysis results of the pale yellow solid obtained in the above reaction by nuclear magnetic resonance spectroscopy ( 1 1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 41. From these results, in this example, 1 the organic compound 8mpTP-4mDBtPBfpm, which is one aspect of the present invention represented by the above structural formula (128), was obtained.

[0405] 1 1H-NMR. δ(CDCl3): 7.38 (t, 1H), 7.47 - 7.53 (m, 4 H), 7.59 - 7.74 (m, 9H), 7.77 - 7.88 (m, 5H), 7.97 - 7.99 (m, 2H), 8.03 - 8.05 (m, 1H), 8.23 - 8.25 (m, 2 H), 8.61 (d, 1H), 8.73 (d, 1H), 9.05 (t, 1H), 9.34 (s, 1H).

Example

[0406] ≪Synthesis Example 8≫ In this example, an organic compound, which is one aspect of the present invention represented by the structural formula (143) of Embodiment 1, 8-(1,1’:3’1’’-Terphenyl-5’-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8mTP-4mDBtPBfpm) will be described in terms of its synthesis method. The structure of 8mTP-4mDBtPBfpm is shown below. 8mTP- 4mDBtPBfpm is as follows.

[0407]

Chemical formula

[0408] <Step 1: Synthesis of 8mTP-4mDBtPBfpm> 503 mg of 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine, 923 mg of (3,5-diphenylphenyl)boronic acid, 1.23 g of tripotassium phosphate, 700 mg of tert-butyl alcohol, and 36 mL of diethylene glycol dimethyl ether were placed in a three-necked flask, and the mixture was degassed by stirring under reduced pressure and then purged with nitrogen. 58.3 mg of palladium(II) acetate and 166 mg of di(1-adamantyl)-n-butylphosphine were added to this mixture, and the mixture was stirred at 120 °C for 7.5 hours. Water was added to this reaction product, and suction filtration was performed. The obtained filtrate was washed with water, ethanol, and toluene. The filtrate was dissolved in hot toluene and passed through a filter aid filled in the order of celite, alumina, and celite. The obtained solution was concentrated, dried, and recrystallized by the diffusion method using toluene / ethanol as a solvent that separates into two phases, yielding 302 mg of the target white solid with a yield of 25%.

[0409]

[0410] 292 mg of this white solid was purified by sublimation using the train sublimation method. Sublimation purification conditions were as follows: while flowing argon gas at a flow rate of 10 mL / min, the pressure was 2.6 Pa, and the solid was heated at 340 °C After sublimation purification, the target product, 8mTP-4mDBtPBfpm, was obtained in a yield of 161 mg (recovery rate 55%, white solid). This synthetic scheme is shown in the following formula (j-1). Shown.

[0411]

Chemical formula

[0412] In addition, the analysis results of the pale yellow solid obtained in the above reaction by nuclear magnetic resonance spectroscopy ( 1 1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 42. From these results, in this example 1 it was found that the organic compound, 8mTP-4mDBtPbfpm, which is one aspect of the present invention represented by the above structural formula (143), was obtained. 1H-NMR. δ (CDCl3): 7.40 - 7.43 (m, 2H), 7.47 - 7.5 3 (m, 6H), 7.63 - 7.66 (m, 2H), 7.74 - 7.76 (m, 4H),

[0413] 1 7.79 - 7.87 (m, 4H), 7.91 (m, 2H), 7.97 - 7.99 (m, 1 H), 8.08 - 8.09 (m, 1H), 8.22 - 8.26 (m, 2H), 8.66( m, 1H), 8.72 - 8.73 (m, 1H), 9.05 - 9.06 (m, 1H), 9. 34 (s, 1H).

Example

[0414] <<Synthesis Example 9>> In this example, an organic compound, which is one aspect of the present invention represented by the structural formula (144) of Embodiment 1, 8-(1,1'-Biphenyl-4-yl)-4-[3-(9H-carbazol-9 -yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4m CzPBfpm), will be described in terms of its synthesis method. The structure of 8BP-4mCzPBfpm is shown below.

[0415]

Chemical formula

[0416] Note that the above 8BP-4mCzPBfpm can be synthesized according to the synthesis scheme represented by the following formula (k-1).

[0417]

Chemical formula

Example

[0418] In this example, as a light-emitting element which is one aspect of the present invention, a light-emitting element was fabricated using 8(βN2)-4mDBtBPBfpm (structural formula (105)), PCBBiF, and a guest material (phosphorescent light-emitting material) described in Example 8 in the light-emitting layer, and the results of measuring its characteristics are shown. Note that in this example, a light-emitting element using [Ir(dmpqn)2(acac)] as the guest material is designated as Light-emitting Element 12, and a light-emitting element using bis{4,6-dimethyl-2- 5-(5-cyano-2-methylphenyl)-3-(3,5-dimethylphenyl)-2-py razinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptane dionato-κ2O,O')iridium(III) (abbreviation: [Ir(dmdppr-m5C as the guest material ​​​​ The light-emitting element using P)2(dpm)] is defined as the light-emitting element 13.

[0419] Note that the element structures of the light-emitting element 12 and the light-emitting element 13 fabricated in this example are the same as those shown in Fig. 14 of Example 4, but the specific configurations of the respective layers constituting the element structure are as shown in Table 7. Further, the chemical formulas of the materials used in this example are shown below. Although the element structures of the light-emitting element 12 and the light-emitting element 13 fabricated in this example are the same as those shown in Fig. 14 of Example 4, the specific configurations of the respective layers constituting the element structure are as shown in Table 7. Further, the chemical formulas of the materials used in this example are shown below. As shown in Table 7. Also, the chemical formulas of the materials used in this example are shown below.

[0420]

Table 7

[0421]

Chemical formula

[0422] ≪Operating characteristics of each light-emitting element≫ The operating characteristics of the fabricated light-emitting element 12 and the light-emitting element 13 were measured. The measurement was performed at room temperature (in an atmosphere maintained at 25 °C). The current density-luminance characteristics, voltage-luminance characteristics, luminance-current efficiency characteristics, and voltage-current characteristics of each light-emitting element are shown in Fig. 43, Fig. 44, Fig. 45, and Fig. 46, respectively.

[0423] The current density-luminance characteristics, voltage-luminance characteristics, luminance-current efficiency characteristics, and voltage-current characteristics of each light-emitting element are shown in Fig. 43, Fig. 44, Fig. 45, and Fig. 46, respectively. The current density-luminance characteristics, voltage-luminance characteristics, luminance-current efficiency characteristics, and voltage-current characteristics of each light-emitting element are shown in Fig. 43, Fig. 44, Fig. 45, and Fig. 46, respectively.

[0424] Also, the main initial characteristic values of each light-emitting element in the vicinity of 1000 cd / m 2 are shown in Table 8 below. .

[0425]

Table 8

[0426] Also, the emission spectrum when a current was passed through each light-emitting element at a current density of 2.5 mA / cm 2 is , as shown in FIG. 47. As shown in FIG. 47, the emission spectrum of the light-emitting element 12 has a peak near 628 nm and is suggested to be derived from the emission of [Ir(dmpqn)2(acac) contained in the light-emitting layer 913. Further, the emission spectrum of the light-emitting element 13 has a peak near 6 48 nm and is suggested to be derived from the emission of [Ir(dmdppr- m5CP)2(dpm)] contained in the light-emitting layer 913.

[0427] Next, a reliability test was conducted on each light-emitting element. The results of the reliability test are shown in FIG. 48. In FIG. 48, the vertical axis represents the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis represents the element driving time (h). The reliability test was a constant current driving test in which a constant current was passed at a current density of 75 mA / cm 2 .

[0428] From the results of the reliability test, the light-emitting element 12 using the organic compound 8(βN2)-4mDBtB PBfpm (structural formula (105)) according to one aspect of the present invention in the light-emitting layer has a time (LT95) of 115 hours when the luminance drops by 5% from the initial luminance, and the light-emitting element 13 has an LT95 of 62 hours . This is the effect due to the fact that the organic compound 8(βN2)-4mDBtBPBfp m according to one aspect of the present invention has a structure in which a plurality of naphthyl groups are linked to the 8-position of the benzofuropyrimidine skeleton. Therefore, it can be said that using the organic compound according to one aspect of the present invention is useful for improving the reliability of the light-emitting element.

Examples

[0429] In this example, as a light-emitting element according to one aspect of the present invention, 8pmTP- 4mDBtPBfpm (Structural formula (126)), PCCP, and [Ir(ppy)2(m dppy)] were used in the light-emitting layer of the light-emitting device 14, and 8BP-4mDBtB PBfpm (Structural formula (103)), PCCP, and [Ir(ppy)2(mdppy) were used in the light-emitting layer to fabricate the light-emitting device 15, and the measurement results of its characteristics are shown.

[0430] Note that the device structures of the light-emitting devices 14 and 15 fabricated in this example are the same as those shown in FIG. 14 shown in Example 4, but the specific configurations of the respective layers constituting the device structure are as shown in Table 9. Also, the chemical formulas of the materials used in this example are shown below.

[0431]

Table 9

[0432]

Chemical formula

[0433] ≪Operating characteristics of each light-emitting device≫ The operating characteristics of the fabricated light-emitting devices 14 and 15 were measured. Note that the measurement was carried out at room temperature (atmosphere maintained at 25 °C).

[0434] The current density-luminance characteristics of each light-emitting device are shown in FIG. 49, the voltage-luminance characteristics are shown in FIG. 50, the luminance-current efficiency characteristics are shown in FIG. 51, and the voltage-current characteristics are shown in FIG. 52, respectively.

[0435] Also, the main initial characteristic values of each light-emitting device near 1000 cd / m 2 are shown in Table 10 below. are shown.

[0436]

Table 10

[0437] Also, when a current is passed through each light-emitting element at a current density of 2.5 mA / cm 2 the emission spectrum is as shown in FIG. 53. As shown in FIG. 53, the emission spectrum of each light-emitting element has a peak near 526 nm, suggesting that it is derived from the emission of [Ir(ppy)2(mdppy)] contained in the light-emitting layer 913.

[0438] Next, a reliability test was conducted on each light-emitting element. The results of the reliability test are shown in FIG. 54. In FIG. 54, the vertical axis represents the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis represents the driving time (h) of the element. The reliability test was a constant current drive test in which a constant current was passed at a current density of 50 mA / cm 2

[0439] From the results of the reliability test, for the light-emitting element 14 using the organic compound 8pmTP-4mDBtPBfpm (structural formula (126)), which is one aspect of the present invention, in the light-emitting layer, the time (LT95) for the luminance to decrease by 5% from the initial luminance is approximately 30 hours, and for the light-emitting element 15 using 8BP-4mDBtBPBfpm (structural formula (103)) in the light-emitting layer, the LT95 was 21 hours. This is due to the effect of the organic compounds 8pmTP-4mDBtPBfpm and 8BP-4 mDBtBPBfpm, which are aspects of the present invention, having a structure in which a plurality of arylene groups are linked at the 8-position of the benzofuropyrimidine skeleton, more preferably a biphenyl group having two linked identical phenyl groups. Therefore, it can be said that using the organic compound which is one aspect of the present invention is useful for improving the reliability of the light-emitting element.

Description of Reference Numerals

[0440] 101: First electrode, 102: Second electrode, 103: EL layer, 103a, 103b: EL layer, 104, 104a, 104b: Charge generation layer, 111, 111a, 111b: Hole injection layer, 112, 112a, 112b: Hole transport layer, 113, 113a, 113b, 113c : Light-emitting layer, 114, 114a, 114b: Electron transport layer, 115, 115a, 115b: Electron injection layer, 200R, 200G, 200B: Optical distance, 201: First substrate, 202: Transistor (FET), 203R, 203G, 203B, 203W: Light-emitting element, 204: EL layer, 205: Second substrate, 206R, 206G, 206B: Color filter, 206 R’, 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: Driving circuit portion (source line driving circuit), 304a, 304b: Driving circuit portion (gate line driving circuit), 305: Sealing material, 306: Second substrate, 307: Wiring, 308: FPC, 309: FET, 310: FET, 311: F ET, 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, 91 3: 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, 4 010: Insulating layer, 4011: Sealing substrate, 4012: Sealing material, 4013: Desiccant, 420 0: Lighting device, 4201: Substrate, 4202: Light-emitting element, 4204: First electrode, 4205 : EL layer, 4206: Second electrode, 4207: Electrode, 4208: Electrode, 4209: Auxiliary lead wire, 4210: Insulating layer, 4211: Sealing substrate, 4212: Sealing material, 4213: Barrier film 、4214: Planarization film, 5101: Light, 5102: Wheel, 5103: Door, 51 04: Display section, 5105: Handle, 5106: Shift lever, 5107: Seat cushion, 5108: Inner rearview mirror, 7000: Housing, 7001: Display section, 7002: Second display section, 7003: Speaker, 7004: LED lamp, 7005: Operation key, 70 06: Connection terminal, 7007: Sensor, 7008: Microphone, 7009: Switch, 7010: Infrared port, 7011: Recording medium reading section, 7014: Antenna, 7015: Shutter button, 7016: Image receiving section, 7018: Stand, 7021: External connection section, 7 022, 7023: Operation button, 7024: Connection terminal, 7025: Band, 7026: Microphone, 7027: Icon representing time, 7028: Other icons, 702 9: Sensor, 7030: Speaker, 7052, 7053, 7054: Information, 9310: Portable band information terminal, 9311: Display section, 9312: Display area, 9313: Hinge, 9315: Housing body

Claims

1. A light-emitting device having a pair of electrodes and a light-emitting layer between the pair of electrodes, wherein the light-emitting layer includes a first organic compound represented by formula (G1) (excluding the compound represented by formula (1)), a second organic compound, and an organometallic complex, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, and the first organic compound and the second organic compound form a combination that forms an exciplex. 【Chemical 1】 (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Also, m and n are each 0 or 1. Also, A is a group having 12 to 100 carbon atoms in total, and a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, or a group to which one or more of a triphenylamine structure are bonded. Also, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.) 【Chemical 2】 (In formula (1), Q represents oxygen or sulfur. Also, A １ and A ２ each independently represent a substituted or unsubstituted polycyclic aromatic hydrocarbon. Also, m represents any one of the integers from 0 to 4. Also, n represents any one of the integers from 1 to 4. Also, R １ to R １２ each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.)

2. A light-emitting device having a pair of electrodes and a light-emitting layer between the pair of electrodes, wherein the light-emitting layer includes a first organic compound represented by formula (G1) (excluding the compound represented by formula (1)), a second organic compound, and an organometallic complex, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, and the first organic compound and the second organic compound form a combination that forms an exciplex. [Chemical 3] (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring. When the benzene ring or the naphthalene ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Also, m and n are each 0 or 1. Also, A is a group having 12 to 100 carbon atoms and represents a group to which any one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, or a triphenylamine structure is bonded. Also, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.) 【Chemical Formula 4】 (In formula (1), Q represents oxygen or sulfur. Also, A １ and A ２ each independently represent a substituted or unsubstituted polycyclic aromatic hydrocarbon. Also, m represents any one of the integers from 0 to 4. Also, n represents any one of the integers from 1 to 4. Also, R １ to R １２ each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.)

3. A light-emitting device having a pair of electrodes and a light-emitting layer between the pair of electrodes, wherein the light-emitting layer includes a first organic compound represented by formula (G1), a second organic compound, and an organometallic complex, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, and the first organic compound and the second organic compound form a combination that forms an exciplex. [Chemical Formula 5] (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted benzene ring. When the benzene ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Also, m and n are each 0 or 1. Also, A is a group having 12 to 100 carbon atoms and represents a group to which any one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, or a triphenylamine structure is bonded. Also, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.)

4. A light-emitting device having a pair of electrodes and a light-emitting layer between the pair of electrodes, wherein the light-emitting layer includes a first organic compound represented by formula (G1), a second organic compound, and an organometallic complex, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, and the first organic compound and the second organic compound form a combination that forms an exciplex. [Chemical Formula 6] (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted naphthalene ring. When the naphthalene ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Also, m and n are each 0 or 1. Also, A is a group having 12 to 100 carbon atoms and represents a group to which any one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, or a triphenylamine structure is bonded. Also, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.)

5. A light-emitting device having a pair of electrodes and a light-emitting layer between the pair of electrodes, wherein the light-emitting layer includes a first organic compound represented by formula (G1) (excluding the compound represented by formula (1)), a second organic compound, and an organometallic complex, the second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, and the first organic compound and the second organic compound form a combination that forms an exciplex. [Chemical Formula 7] (In formula (G1), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each represent an identical substituted or unsubstituted aromatic hydrocarbon ring, the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Also, m and n are each 0 or 1. Also, A is a group having 12 to 100 carbon atoms in total, and represents a group to which any one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring containing a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzimidazole ring, or a triphenylamine structure are bonded. Also, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.) [Chemical Formula 8] (In formula (1), Q represents oxygen or sulfur. Also, A １ and A ２ each independently represent a substituted or unsubstituted polycyclic aromatic hydrocarbon. Also, m represents any one of integers from 0 to 4. Also, n represents any one of integers from 1 to 4. Also, R １ to R １２ each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.)

6. It has a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer has a first organic compound represented by formula (G2), a second organic compound, and an organometallic complex, The second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, The light-emitting device, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemical Formula 9】 (In formula (G2), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Also, m and n are each 0 or 1. Further, α represents a substituted or unsubstituted phenylene group, and t represents an integer from 0 to 4. Also, Ht ｕｎｉ represents a heteroaromatic ring having any one of a pyrrole ring structure, a furan ring structure, or a thiophene ring structure. Also, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.)

7. It has a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer has a first organic compound represented by formula (G3), a second organic compound, and an organometallic complex, The second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, The light-emitting device, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemical 10】 (In formula (G3), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Also, m and n are each 0 or 1. Also, Ht ｕｎｉ represents a heteroaromatic ring having any one of a pyrrole ring structure, a furan ring structure, or a thiophene ring structure. Also, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.)

8. It has a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer has a first organic compound represented by formula (G4), a second organic compound, and an organometallic complex, The second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, The light-emitting device, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemical 11】 (In formula (G4), Q represents oxygen or sulfur. Ar １ , Ar ２ , Ar ３ , and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, the number of carbon atoms forming the aromatic hydrocarbon ring is 6 or more and 25 or less, and when the aromatic hydrocarbon ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, or a cyano group. Also, m and n are each 0 or 1. Further, Ht ｕｎｉ represents a heteroaromatic ring having any one of a pyrrole ring structure, a furan ring structure, or a thiophene ring structure. Also, R １ represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.)

9. In any one of Claims 6 to 8, The Ht ｕｎｉ is a light-emitting element represented by any one of formulas (Ht-1) to (Ht-26). 【Chemical 12】 (In formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. Also, R ２ to R ７１ each represent a substituent of 1 to 4, and each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. Also, Ar ５ represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.)

10. In any one of Claims 6 to 9, Ar １ 、 Ar ２ 、 Ar ３ 、 and Ar ４ are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring, a light-emitting element.

11. In any one of Claims 6 to 10, Ar １ 、Ar ２ 、Ar ３ 、and Ar ４ are the same, a light-emitting element.

12. In any one of Claims 1 to 11, Ar １ 、 Ar ２ 、 Ar ３ 、 and Ar ４ is unsubstituted, a light-emitting element.

13. In any one of Claim 1, Claim 2, Claims 5 to 11, The light-emitting device, wherein the partial structure represented by the following formula (G-X) in the formulas (G1) to (G4) is represented by any one of the following formulas (G-X-p1) to (G-X-p12) and (G-X-n1) to (G-X-n6). 【Chemical 13】 【Chemical Formula 14】

14. It has a pair of electrodes and a light-emitting layer between the pair of electrodes, The light-emitting layer has a first organic compound, a second organic compound, and an organometallic complex, The first organic compound is a compound represented by any one of formulas (100) to (103), formula (105), formula (126), formula (128), formula (143), and formula (144), The second organic compound is an aromatic amine, a carbazole derivative, a dibenzothiophene derivative, or a dibenzofuran derivative, The light-emitting device, wherein the first organic compound and the second organic compound are a combination that forms an exciplex. 【Chemical 15】 【Chemical Formula 16】

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