Organic compound, light-emitting device, electronic device and lighting device

Abstract

Connection represented by formula (G1): where QO represents where at least one of R 1 to R 12 a first group which is a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms, and where each of the other from R 1 to R 12 independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group or a group with 1 to 50 carbon atoms.

Description

Background of the invention 1. Field of the invention

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting device, an electronic device, and a lighting device. It should be noted that an embodiment of the present invention is not limited to these. That is to say, an embodiment of the present invention relates to an object, a method, a manufacturing process, or an operating procedure. An embodiment of the present invention relates to a process, a machine, a product, or a composition. Specific examples include a semiconductor device, a display device, a liquid crystal display device, and the like. 2. Description of the state of the art

[0002] A light-emitting element that includes an EL layer between a pair of electrodes (also called an organic EL element) has properties such as thinness, lightness, a high response speed to input signals, and low power consumption; therefore, a display incorporating such a light-emitting element has attracted attention as a next-generation flat panel display.

[0003] In a light-emitting atom, a voltage applied between a pair of electrodes causes a recombination of electrons and holes injected by the electrodes into an EL layer. This excites a light-emitting substance (organic compound) contained in the EL layer. Light is emitted when the light-emitting substance returns from the excited state to its ground state. The excited state can be a singlet excitation state (S*) or a triplet excitation state (T*). Light emission from a singlet excitation state is called fluorescence, and light emission from a triplet excitation state is called phosphorescence. The statistical production ratio of these states in the light-emitting atom is assumed to be S*:T* = 1:3.Since the spectrum of light emitted by a light-emitting substance depends on the light-emitting substance itself, light-emitting elements with different colors can be obtained by using different types of organic compounds as light-emitting substances.

[0004] To improve the elemental properties of such a light-emitting element, improvements to the elemental structure, the development of a material, and the like have been actively carried out (see, for example, patent document 1). [Reference]

[0005] Patent document 1: Japanese patent disclosure no. 2010-182699

[0006] WO 2018 / 060307 A1 concerns diazadibenzofuran or diazadibenzothiophene derivatives substituted with carbazole, fluorene, phenanthrene, benzofuran and / or benzothiophene groups and used in electronic devices.

[0007] WO 2018 / 060 218 A1 concerns diazadibenzofuran or diazadibenzothiophene derivatives substituted with carbazole structures and used in electronic devices.

[0008] C. Galvez et al., New routes to condensed thiophene ring systems from orthodiaminothiophene derivatives, Journal of chemical research, 1985, No. 9, pp. 296-297, concerns the synthesis of 2,3-diaminothiophene and 2,3-diarainebenzo[b]thiophene and their conversion into polycyclic systems. Summary of the invention

[0009] In the development of light-emitting elements, organic compounds used in the light-emitting element are very important for improving its properties and reliability. In one embodiment of the present invention, a novel organic compound is therefore provided. That is to say, a novel organic compound is provided that effectively contributes to improving the element's properties and reliability. In another embodiment of the present invention, a novel organic compound is provided that can be used in a light-emitting element. In a further embodiment of the present invention, a novel organic compound is provided that can be used in an EL layer of a light-emitting element.In a further embodiment of the present invention, a highly efficient, very reliable, and novel light-emitting element is provided, in which a novel organic compound of an embodiment of the present invention is used. In a further embodiment of the present invention, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these objects does not preclude the existence of further objects. In one embodiment of the present invention, it is not necessary to fulfill all objects. Further objects will become apparent from the explanation of the description, the drawings, the claims, and the like, and can be derived from them.

[0010] The invention relates to a connection according to claim 1, a connection according to claim 5, a light-emitting device according to claim 13, an electronic device according to claim 16 and a lighting device according to claim 17. Advantageous embodiments are found in the dependent claims.

[0011] One embodiment of the present invention is an organic compound represented by the following formula (G1).

[0012] In formula (G1), QO represents at least one of R 1 to R 12 represents a first group, which is a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms, and each of the other from R 1 to R 12Each of these independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0013] In each of the foregoing embodiments, the first group preferably comprises a total of 3 to 100 carbon atoms.

[0014] In a further embodiment of the present invention, the first group comprises a structure selected from the structures represented by formulas (A-1) to (A-21).

[0015] Each of the other ones from R 1 to R 12 independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0016] In formulas (A-1) to (A-21), Q'O represents S, and each of R represents 13 to R 24Each of these represents, independently of one another, hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0017] In a further embodiment of the present invention, the first group comprises formulas (A-1) to (A-21).

[0018] Each of the other ones from R 1 to R 12 independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0019] In formulas (A-1) to (A-21), Q'O represents S, and each of R represents 13 to R 24Each of these represents, independently of one another, hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0020] In another embodiment, the structure selected from those represented by formulas (A-1) to (A-21) is linked to the dibenzobenzofurochinoxaline or dibenzobenzothienochinoxaline framework via a substituted or unsubstituted arylene group with 6 to 24 carbon atoms in a ring or a substituted or unsubstituted heteroarylene group with 3 to 24 carbon atoms in a ring.

[0021] Another embodiment of the present invention is an organic compound represented by the following formula (G1).

[0022] In the formula (G1), QO represents, R 3 represents a first group that has a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms, and each of R 1 , R 2 and R 4 to R 12 Each of these independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0023] In a further embodiment of the present invention, the first group has a hole transport property that is higher than an electron transport property.

[0024] In a further embodiment of the present invention, the first group comprises a fluorene scaffold, a phenanthrene scaffold, a triphenylene scaffold, a naphthalene scaffold, a dibenzothiophene scaffold, a dibenzofuran scaffold or a carbazole scaffold.

[0025] In each of the foregoing embodiments, R exhibits 3 preferably a total of 3 to 100 carbon atoms.

[0026] In a further embodiment of the present invention, the first group comprises a structure selected from the structures represented by formulas (A-1) to (A-21).

[0027] Each of R 1 , R 2 and R 4 to R 12 each independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0033]

[0028] In formulas (A-1) to (A-21), Q'O represents S, and each of R represents 13 to R 24Each of these represents, independently of one another, hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0029] In a further embodiment of the present invention, the first group is represented by one of the formulas (A-1) to (A-21).

[0030] Each of R 1 , R 2 and R 4 to R 12 Each of these independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0031] In formulas (A-1) to (A-21), Q'O represents S, and each of R represents 13 to R 24Each of these represents, independently of one another, hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0032] In another embodiment, the structure selected from those represented by formulas (A-1) to (A-21) is linked to the dibenzobenzofurochinoxaline or dibenzobenzothienochinoxaline framework via a substituted or unsubstituted arylene group with 6 to 24 carbon atoms in a ring or a substituted or unsubstituted heteroarylene group with 3 to 24 carbon atoms in a ring.

[0033] In each of the foregoing embodiments, the group comprising 1 to 50 carbon atoms is an alkyloxy group, an aryloxy group, an amino group to which an alkyl group is bonded, an amino group to which an aryl group is bonded, a cyano group, a carboxyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a silyl group to which an alkyl group is bonded, a silyl group to which an aryl group is bonded, an alkyl group, a cycloalkyl group, a heteroaryl group or an aryl group.

[0034] Another embodiment of the present invention is an organic compound represented by the structural formula (100) or the structural formula (125).

[0035] Another embodiment of the present invention is a light-emitting device comprising: a light-emitting layer between a pair of electrodes, wherein the light-emitting layer comprises the compound according to the invention.

[0036] Another embodiment of the present invention is the light-emitting device according to the invention, wherein the light-emitting layer further comprises a metal-organic complex.

[0037] Another embodiment of the present invention is the light-emitting device according to the invention, wherein the metal-organic complex is an iridium complex with a phenylquinoline framework.

[0038] Another embodiment of the present invention is an electronic device comprising: the light-emitting device according to the invention; and at least one of a microphone, a camera, a control button, an external connection section and a loudspeaker.

[0039] Another embodiment of the present invention is a lighting device comprising: the light-emitting device according to the invention; and at least one housing, a cover and a support.

[0040] Another embodiment of the present disclosure is a light-emitting element comprising an organic compound having a benzofuroquinoxaline skeleton or a benzothienoquinoxaline skeleton, preferably a light-emitting element comprising an organic compound having a dibenzo[f,h][1]benzofuro[2,3-b]quinoxaline skeleton or a dibenzo[f,h][1]benzothieno[2,3-b]quinoxaline skeleton. It should be noted that an embodiment of the present disclosure also comprises a light-emitting element comprising the aforementioned organic compound and a substance that converts triplet excitation energy into light emission, such as a phosphorescent material containing a metal-organic complex or a TADF material.

[0041] Another embodiment of the present disclosure is a light-emitting element comprising the organic compound of an embodiment of the present invention described above. It should be noted that another embodiment of the present disclosure comprises a light-emitting element in which an EL layer provided between a pair of electrodes, or a light-emitting layer contained within the EL layer, comprises the organic compound of an embodiment of the present invention.

[0042] Additionally, a light-emitting device comprising a transistor, a substrate and the like is also included within the scope of protection of the invention.

[0043] Furthermore, in addition to the light-emitting device, an electronic device and a lighting device, which include a microphone, a camera, a control button, an external connection section, a housing, a cover, a support, a loudspeaker or the like, are also included within the scope of protection of the invention.

[0044] The organic compound of an embodiment of the present invention can be used as a light-emitting substance. Alternatively, the organic compound of an embodiment of the present invention can be used in combination with a light-emitting substance that emits phosphorescence (a phosphorescent compound) for a light-emitting layer of a light-emitting element. That is, light emission from a triplet excitation state can be obtained from the light-emitting layer; therefore, the efficiency of the light-emitting element can be improved, which is very effective. Accordingly, one embodiment of the present disclosure also includes a light-emitting element in which the organic compound of an embodiment of the present invention and a phosphorescent compound are used in combination in a light-emitting layer.A structure in which the light-emitting layer also contains a third substance can also be used.

[0045] One embodiment of the present disclosure comprises a light-emitting device which includes a light-emitting element, and the scope of protection of one embodiment of the invention comprises a lighting device which includes the light-emitting device.

[0046] The term "light-emitting device" in this description therefore refers to an image display device and a light source (including an illumination device). Additionally, the category of light-emitting device includes all of the following modules: a module in which a connector, such as a flexible printed circuit (FPC) or a tape carrier package (TCP), is connected to a light-emitting device; a module in which a printed circuit board is provided at the end of a TCP; and a module in which an integrated circuit (IC) is mounted directly onto a light-emitting element by a chip-on-glass (COG) process.

[0047] According to one embodiment of the present invention, a novel organic compound can be provided. In other words, a novel organic compound that effectively contributes to improving the element's properties and reliability can be provided. According to one embodiment of the present invention, a novel organic compound can be provided that can be used in a light-emitting element. According to one embodiment of the present invention, a novel organic compound can be provided that can be used in an EL layer of a light-emitting element. According to one embodiment of the present disclosure, a highly efficient, very reliable, and novel light-emitting element can be provided in which a novel organic compound of an embodiment of the present invention is used.Furthermore, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. It should be noted that the description of these effects does not preclude the existence of further effects. In one embodiment of the present invention, it is not necessarily required to achieve all effects. Further effects will become apparent from the explanation of the description, the drawings, the claims, and the like, and can be derived from them. Brief description of the drawings Fig. 1A to Fig. 1E represent structures of light-emitting elements. Fig. 2A to Fig. 2C represent light-emitting devices. Fig. 3A and Fig. 3B represents a light-emitting device. Fig. 4A to Fig. 4G represents electronic devices. Fig. 5A to Fig. 5C represents an electronic device. Fig. 6A and Fig. 6B represents a vehicle. Fig. 7A and Fig. 7B represents lighting devices. Fig. 8 shows a 1 H-NMR spectrum of an organic compound represented by the structural formula (100). Fig. 9A and Fig. Figures 9B show a UV-VIS absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (100). Fig. 10 represents a light-emitting element. Fig. Figure 11 shows the current density-luminance properties of a light-emitting element 1 and a light-emitting comparison element 2. Fig. Figure 12 shows the voltage-luminance properties of the light-emitting element 1 and the light-emitting comparison element 2. Fig. Figure 13 shows the luminance-current efficiency properties of light-emitting element 1 and light-emitting comparison element 2. Fig. Figure 14 shows the voltage-current characteristics of the light-emitting element 1 and the light-emitting comparison element 2. Fig. Figure 15 shows the emission spectra of light-emitting element 1 and light-emitting reference element 2. Fig. Figure 16 shows the reliability of the light-emitting element 1 and the light-emitting comparison element 2. Fig. 17 shows a 1 H-NMR spectrum of an organic compound represented by the structural formula (125). Detailed description of the invention

[0048] Embodiments of the present invention and embodiments of the present disclosure are described below with reference to the drawings. It should be noted that the present invention is not limited to the following description; the types and details of the present invention can be modified in various ways without departing from the basic concept and scope of the present invention. Therefore, the present invention should not be considered as limited to the description of the following embodiments.

[0049] It should be noted that the position, size, area, or the like of each component shown in drawings and the like is, in some cases, not shown precisely for ease of understanding. The disclosed invention is therefore not necessarily limited to the position, size, area, or the like shown in the drawings and the like.

[0050] In the explanation of the embodiments of the present invention in this description and the like, based on the drawings, identical components in different drawings are generally provided with the same reference numeral. (Version 1)

[0051] In this embodiment, organic compounds of embodiments of the present invention are described.

[0052] The organic compounds of embodiments of the present invention each have a structure represented by the general formula (G1) which has a dibenzobenzofuroquinoxaline skeleton or a dibenzobenzothienoquinoxaline skeleton.

[0053] In the general formula (G1), QO or S represents at least one of R 1 to R 12 represents a first group that has a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms, and the other or the others of R 1 to R 12 Each of these represents, independently of one another, hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0054] Alternatively, in the general formula (G1), QO or S represents at least one of R. 1 to R 12represents a first group that has a substituted or unsubstituted hole transport framework with 3 to 30 carbon atoms in a ring, and the other or other of R 1 to R 12 Each of these represents, independently of one another, hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0055] Alternatively, in the general formula (G1), QO or S represents at least one of R. 1 to R 12 represents a first group that has a fluorene scaffold, a phenanthrene scaffold, a triphenylene scaffold, a naphthalene scaffold, a dibenzothiophene scaffold, a dibenzofuran scaffold or a carbazole scaffold, and the other or the others of R 1 to R 12Each of these represents, independently of one another, hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0056] In each of the above structures, the first group preferably comprises a total of 3 to 100 carbon atoms.

[0057] Alternatively, in the general formula (G1), QO or S represents at least one of R. 1 to R 12 represents a first group to which one of the structures represented by the following general formulas (A-1) to (A-21) is bonded via a substituted or unsubstituted aryl group with 6 to 24 carbon atoms in a ring or a substituted or unsubstituted heteroarylene group with 3 to 24 carbon atoms in a ring, and the other or the other of R 1 to R 12Each of these represents, independently of one another, hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0058] Alternatively, in the general formula (G1), QO or S represents at least one of R. 1 to R 12 represents a first group, which is represented by one of the following general formulas (A-1) to (A-21), and the other or the others of R 1 to R 12 Each of these represents, independently of one another, hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0059] In the general formulas (A-1) to (A-21), Q'O represents S, and R 13 to R 24Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0060] Alternatively, in the general formula (G1) represents QO or S, R 3 represents a first group that has a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms, and R 1 , R 2 and R 4 to R 12 Each independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0061] Alternatively, in the general formula (G1) represents QO or S, R 3represents a first group that has a substituted or unsubstituted hole transport framework with 3 to 30 carbon atoms in a ring, and R 1 , R 2 and R 4 to R 12 Each independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0062] Alternatively, in the general formula (G1) represents QO or S, R 3 represents a first group that has a fluorene scaffold, a phenanthrene scaffold, a triphenylene scaffold, a naphthalene scaffold, a dibenzothiophene scaffold, a dibenzofuran scaffold or a carbazole scaffold, and R 1 , R 2 and R 4 to R 12 Each independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0063] In each of the above structures, R 3 preferably a total of 3 to 100 carbon atoms.

[0064] Alternatively, in the general formula (G1) represents QO or S, R 3 represents a first group to which one of the structures represented by the following general formulas (A-1) to (A-21) is bonded via a substituted or unsubstituted arylene group with 6 to 24 carbon atoms in a ring or a substituted or unsubstituted heteroarylene group with 3 to 24 carbon atoms in a ring, and R 1 , R 2 and R 4 to R 12 Each independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0065] Alternatively, in the general formula (G1) represents QO or S, R 3represents a first group, which is represented by one of the following general formulas (A-1) to (A-21), and R 1 , R 2 and R 4 to R 12 Each independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0066] In the general formulas (A-1) to (A-21), Q'O represents S, and R 13 to R 24 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0067] It should be noted that in each of the above structures, the group with 1 to 50 carbon atoms is preferably an alkyloxy group, an aryloxy group, an amino group to which an alkyl group is bonded, an amino group to which an aryl group is bonded, a cyano group, a carboxyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a silyl group to which an alkyl group is bonded, a silyl group to which an aryl group is bonded, an alkyl group, a cycloalkyl group, a heteroaryl group or an aryl group. Specific examples of these groups include a methoxy group, an ethoxy group, a propoxy group, a tert-butoxy group, a phenoxy group, a 4-methylphenoxy group, a 3,5-dimethylphenoxy group, a 1-naphthoxy group, a 2-naphthoxy group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, a methylethylamino group, and a phenylmethylamino group.a phenylamino group, a diphenylamino group, a 1-naphthylamino group, a 2-naphthylamino group, an N-1-naphthyl-N-phenylamino group, an N-2-naphthyl-N-phenylamino group, a bis(biphenyl-4-yl)amino group, an N,N-bis(p-terphenyl)amino group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a trimethylsilyl group, a triphenylsilyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, an n-hexyl group, a benzyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenyl group, a 3-Biphenyl group, a 4-biphenyl group, a phenanthrenyl group, a triphenylenyl group, a 9,9-dimethylfluorenyl group, a pyridyl group, a quinolyl group, a 9-carbazolyl group, a 9-phenyl-2-carbazolyl group,A 9-phenyl-3-carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. Furthermore, groups with 25 or fewer carbon atoms, i.e., 1 to 25 carbon atoms, such as a spirofluorenyl group and an N,N-bis(p-biphenylyl)amino group, are preferred with regard to their sublimation ability.

[0068] It should be noted that the hydrogen in the framework of the organic compound of an embodiment of the present invention may be deuterium.

[0069] It should be noted that in each of the above structures, the substitution in general formula (G1) and general formulas (A-1) to (A-21) is preferably substitution by a substituent such as an alkyl group with 1 to 6 carbon atoms, e.g., a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group, or substitution by a substituent such as an aryl group with 6 to 12 carbon atoms, e.g., a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group. These substituents can be bonded together to form a ring.In the case where, for example, the arylene group is a 2,7-fluorenylene group having two phenyl groups as substituents at the 9-position, the phenyl groups can be bonded together to form a spiro-9,9'-bifluorene-2,7-diyl group.

[0070] For each of the above structures, specific examples of the condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms, defined by R, are included. 1 to R 12 represented in the general formula (G1) are a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a naphthalene ring, a benzothiophene ring, a benzofuran ring, an indole ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a benzonaphthothiophene ring, a dibenzofuran ring, a benzonaphthofuran ring, a carbazole ring, a benzocarbazole ring and a dibenzocarbazole ring.

[0071] For each of the above structures, specific examples include the hole transport framework with 3 to 30 carbon atoms in a ring, which is defined by R 1 to R 12 represented in the general formula (G1), a naphthalene ring, a benzothiophene ring, a benzofuran ring, an indole ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a benzonaphthothiophene ring, a dibenzofuran ring, a benzonaphthofuran ring, a carbazole ring, a benzocarbazole ring and a dibenzocarbazole ring.

[0072] For each of the above structures, specific examples of the arylene group with 6 to 24 carbon atoms in a ring, represented by R 1 to R 12represented in the general formula (G1) is a phenylene group, a naphthalenediyl group, a biphenylediyl group, a terphenylediyl group, a fluorenediyl group, a phenanthrenediyl group and a triphenylenediyl group.

[0073] For each of the above structures, specific examples of the heteroarylene group with 3 to 24 carbon atoms in a ring, represented by R 1 to R 12represented in the general formula (G1) is a pyridindiyl group, a pyrazindiyl group, a pyrimidindiyl group, a triazindiyl group, a triazolediyl group, an oxadiazolediyl group, a thiadiazolediyl group, an oxazolediyl group, a thiazolediyl group, a thiophenediyl group, a pyrrolediyl group, a furandiyl group, a selenophenediyl group, a benzothiophenediyl group, a benzopyrrolediyl group, a benzofurandiyl group, a quinolinediyl group, an isoquinolinediyl group, a dibenzothiophenediyl group, a carbazolediyl group and a dibenzofurandiyl group.

[0074] For each of the above structures, specific examples of the alkyl group with 1 to 6 carbon atoms, represented by R, are included. 13 to R 24represented in the general formulas (A-1) to (A-21), a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a neohexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group and a 2,3-dimethylbutyl group.

[0075] For each of the above structures, specific examples of the cycloalkyl group with 5 to 7 carbon atoms in a ring, represented by R, are included. 13 to R 24 represented in the general formulas (A-1) to (A-21) is a cyclopentyl group, a cyclohexyl group and a cycloheptyl group.

[0076] Next, specific structural formulas of the above-mentioned organic compounds of embodiments of the present invention are shown below.

[0077] It should be noted that the organic compounds represented by structural formulas (100) to (175) are examples of the organic compound represented by the general formula (G1). The organic compound of an embodiment of the present invention is not limited thereto.

[0078] Next, an example of a method for synthesizing the organic compound of an embodiment of the present invention, represented by the general formula (G1), will be described.

[0079] First, an example of a method for synthesizing a dibenzobenzofuroquinoxaline derivative or a dibenzobenzothienoquinoxaline derivative is described, each being the organic compound represented by the following general formula (G1).

[0080] In the general formula (G1), QO or S represents R 1 to R 12 each independently represent hydrogen or a substituent, and at least one of R 1 to R 12 represents a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms. < <Verfahren zum Synthetisieren einer Halogenverbindung, die durch die allgemeine Formel (G0) dargestellt wird> >

[0081] First, a method for synthesizing a halogen compound (general formula (G0)) is described, which is used for the synthesis of the dibenzobenzofuroquinoxaline derivative or the dibenzobenzothienoquinoxaline derivative, which are represented by the general formula (G1).

[0082] For example, the halogen compound represented by the following general formula (G0) can be easily synthesized by the synthesis procedure described below. A first synthesis procedure and a second synthesis procedure are described here.

[0083] In the general formula (G0), QO or S represents R 31 to R 42 each independently represent hydrogen or a substituent, and at least one of R 31 to R 42 represents a halogen. <Erstes Syntheseverfahren>

[0084] The halogen compound represented by the general formula (G0) can be obtained by reacting a halogenated dibenzoquinoxaline derivative (A1) having a phenyl group to which a hydroxyl group or a sulfanyl group is bonded with a base (A2), such as potassium carbonate, as shown below in the synthesis scheme (A-1).

[0085] It should be noted that in the synthesis scheme (A-1) QO represents S, X represents a halogen, R 31 to R 42 each independently represent hydrogen or a substituent and at least one of R 31 to R 42 represents a halogen. <Zweites Syntheseverfahren>

[0086] The halogen compound represented by the general formula (G0) can also be obtained by reacting a phenyl group to which a methyloxy group or a methylsulfanyl group is bonded, a dibenzoquinoxaline derivative (A1') with an amino group and tert-butyl nitrite together, as shown in the synthesis scheme (A-1') below.

[0087] It should be noted that in the synthesis scheme (A-1') represents QO or S, R 31 to R 42 each independently represent hydrogen or a substituent and at least one of R 31 to R 42 represents a halogen. < <Verfahren zum Synthetisieren der organischen Verbindung, die durch die allgemeine Formel (G1) dargestellt wird> >

[0088] Next, a method for synthesizing the dibenzobenzofuroquinoxaline derivatives or the dibenzobenzothienoquinoxaline derivatives, which are represented by the general formula (G1), is described.

[0089] The dibenzobenzofuroquinoxaline derivatives or the dibenzobenzothienoquinoxaline derivatives represented by the general formula (G1) can be obtained by coupling the halogen compound (G0) obtained by the above scheme (A-1) or (A-1') and a boronic acid compound (B1) as shown below in the synthesis scheme (A-2).

[0090] It should be noted that in the synthesis scheme (A-2) QO or S represents R 1 to R 12 and R 31 to R 42 each independently represent hydrogen or a substituent and at least one of R 1 to R 12has a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms. B 1 represents a boronic acid, a boron ester, a cyclic triol borate salt, or the like.

[0091] Since various types of compounds are commercially available as the aforementioned compounds (A1) and (A1') or can be synthesized as compounds (A1) and (A1'), many types of organic compounds can be synthesized as dibenzobenzofuroquinoxaline derivatives or dibenzobenzothienoquinoxaline derivatives of an embodiment of the present invention, which are represented by the general formula (G1). Thus, the organic compound of an embodiment of the present invention is highly variable.

[0092] Specific structural formulas of the above compound (G0) are shown below.

[0093] The organic compounds represented by structural formulas (200) to (223) are examples of the halogen compound represented by the general formula (G0). The organic compound of an embodiment of the present invention is not limited thereto.

[0094] The above describes an example of the process for synthesizing the dibenzobenzofuroquinoxaline derivative or the dibenzobenzothienoquinoxaline derivative, each of which is an organic compound of an embodiment of the present invention. The present invention is not limited to this example, and another synthesis method may be used.

[0095] It should be noted that the organic compound described in this embodiment can be used in combination with one of the structures described in the other embodiments, as required.

[0096] It should be noted that the aforementioned organic compounds of embodiments of the present invention each exhibit electron transport and hole transport properties and can therefore be used as host material in a light-emitting layer or in an electron transport layer or a hole transport layer. The organic compounds of embodiments of the present invention can each maintain a relatively high T1 level and are therefore preferably used as host material in combination with a phosphorescent substance. Furthermore, the aforementioned organic compounds emit fluorescence and can thus be used as light-emitting substances of light-emitting elements.Therefore, light-emitting elements containing these organic compounds can also be considered embodiments of the present invention.

[0097] The organic compounds of embodiments of the present invention each exhibit a low LUMO level and are therefore preferred as compounds that readily accept electrons. Consequently, the organic compounds are preferably used as host material in an electron transport layer or a light-emitting layer, in which case the drive voltage of the light-emitting element can be reduced.

[0098] It should be noted that when a combination of the organic compound of an embodiment of the present invention and an organic compound having a high HOMO level (in particular greater than or equal to -5.7 eV) and readily accepting holes is used, an exciplex can be formed and excitation energy can be efficiently transferred from the exciplex to a light-emitting substance; consequently, the efficiency and reliability of a phosphorescent light-emitting element can be increased and the drive voltage of the phosphorescent light-emitting element can be reduced.For specific examples of the organic compounds (a hole transport material and an electron transport material) used in combination with the organic compound of an embodiment of the present invention, any of the materials described in embodiment 2 may be used in a suitable manner.

[0099] Using the organic compound of an embodiment of the present invention, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency can be produced. Furthermore, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with low power consumption can be produced.

[0100] In embodiment 1, one embodiment of the present invention has been described. Further embodiments of the present invention are described in the other embodiments. It should be noted that an embodiment of the present invention is not limited to this. In other words, various embodiments of the invention are described in this embodiment and in the other embodiments, and an embodiment of the present invention is not limited to a specific embodiment. For example, although the example in which an embodiment of the present invention is used with a light-emitting element is described, an embodiment of the present invention is not limited to this. Depending on the circumstances or conditions, an embodiment of the present invention may be used with objects that differ from a light-emitting element.Furthermore, depending on the circumstances or conditions, an embodiment of the present invention does not necessarily have to be used with a light-emitting element.

[0101] The structure described in this embodiment can be used in combination with one of the structures described in the other embodiments, as required. (Version 2)

[0102] In this embodiment, light-emitting elements of embodiments of the present invention are described. The organic compound of an embodiment of the present invention can be used for the light-emitting element described in this embodiment. <<Grundlegende Struktur des Licht emittierenden Elements> >

[0103] Fig.1A represents a light-emitting element that includes an EL layer between a pair of electrodes. In particular, an EL layer 103, comprising a light-emitting layer, is provided between a first electrode 101 and a second electrode 102.

[0104] Fig. 1B represents a light-emitting element that has a multilayer structure (tandem structure) in which a multitude of EL layers (two EL layers 103a and 103b in Fig. 1B) is provided between a pair of electrodes and a charge-generating layer 104 is provided between the EL layers. Using such a light-emitting tandem element, a low-power light-emitting device that can be operated at a low voltage can be obtained.

[0105] The charge-generating layer 104 has a function for injecting electrons into one of the EL layers (103a or 103b) and for injecting holes into the other of the EL layers (103b or 103a) when a voltage is applied between the first electrode 101 and the second electrode 102. Therefore, injected into Fig. 1B the charge generation layer 104 injects electrons into the EL layer 103a and injects holes into the EL layer 103b when a voltage is applied such that the potential of the first electrode 101 becomes higher than that of the second electrode 102.

[0106] With regard to light extraction efficiency, the charge-generating layer 104 preferably has a transmittance for visible light (in particular, the charge-generating layer 104 has a transmittance for visible light of 40% or more). The charge-generating layer 104 functions even if it has a lower conductivity than the first electrode 101 or the second electrode 102.

[0107] Fig. 1C represents a multilayer structure of the EL layer 103. In the case where in Fig. Since the first electrode 101 serves as the 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 arranged in that order above the first electrode 101. Even in the case where a multitude of EL layers are present, as in the case described in Fig.The tandem structure shown in 1B is provided, the layers are as described above and in Fig. The diagram shows the electrodes arranged sequentially in each EL layer, starting from the anode side. If the first electrode 101 is a cathode and the second electrode 102 is an anode, the arrangement order is reversed.

[0108] In the case where several EL layers are arranged on top of each other, three EL layers (103a, 103b and 103c), as in Fig.The light-emitting layers (113, 113a, 113b, and 113c) are arranged one above the other, separated by charge-generating layers (104a and 104b). It should be noted that the number of stacked layers is not limited to two or three and can be four or more. The light-emitting layers (113, 113a, 113b, and 113c) contained within the EL layers (103, 103a, 103b, and 103c) each contain a suitable combination of a light-emitting substance and a variety of other substances, such that fluorescence or phosphorescence of a desired emission color can be obtained. In the case where a variety of light-emitting layers 113 (113a, 113b, and 113c) are provided, the light-emitting layers can exhibit the respective emission colors. In this case, the light-emitting substance and other substances are different between the stacked light-emitting layers.For example, light-emitting layer 113a can emit blue light, light-emitting layer 113b can emit red, green, or yellow light, and light-emitting layer 113c can emit blue light. In another example, light-emitting layer 113a can emit red light, light-emitting layer 113b can emit blue, green, or yellow light, and light-emitting layer 113c can emit red light. It should be noted that other combinations of emission colors may be appropriately used, taking into account the luminance and color properties of the emission.

[0109] In the light-emitting element of an embodiment of the present invention, light emitted by the EL layers (103, 103a and 103b) can be brought to resonance between the electrodes, thus amplifying the resulting light emission. Fig.1C, the light-emitting element can, for example, have an optical microresonator (microcavity) structure if the first electrode 101 is a reflective electrode and the second electrode 102 is a transflective electrode, in which case the light emission obtained from the EL layer 103 can be enhanced.

[0110] It should be noted that if the first electrode 101 of the light-emitting element is a reflective electrode having a multilayer structure consisting of a reflective conductive material and a translucent conductive material (a transparent conductive film), optical adjustment can be achieved by controlling the thickness of the transparent conductive film. In particular, if the wavelength of the light obtained from the light-emitting layer 113 is λ, the distance between the first electrode 101 and the second electrode 102 is preferably set to approximately mλ / 2 (where m is a natural number).

[0111] To amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, the optical path length from the first electrode 101 to a region of the light-emitting layer 113 where the desired light is obtained (light-emitting region), and the optical path length from the second electrode 102 to the region of the light-emitting layer 113 where the desired light is obtained (light-emitting region), are preferably set to approximately (2m'+1)λ / 4 (m' is a natural number). Here, the light-emitting region denotes a region of the light-emitting layer 113 where holes and electrons recombine.

[0112] By such optical adjustment, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed and light emission with high color purity can be obtained.

[0113] In this case, the optical path length between the first electrode 101 and the second electrode 102 is more precisely the total thickness from a reflection region in the first electrode 101 to a reflection region in the second electrode 102. However, it is difficult to determine the reflection regions in the first electrode 101 and the second electrode 102 precisely; therefore, it is assumed that the aforementioned effect can be achieved sufficiently regardless of where the reflection regions in the first electrode 101 and the second electrode 102 are located. Furthermore, the optical path length between the first electrode 101 and the light-emitting layer that emits the desired light is more precisely the optical path length between the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer that emits the desired light.However, it is difficult to precisely determine the reflection area in the first electrode 101 and the light-emitting area in the light-emitting layer that emits the desired light; therefore, it is assumed that the above effect can be sufficiently achieved regardless of where the reflection area and the light-emitting area are located in the first electrode 101 and the light-emitting layer that emits the desired light, respectively.

[0114] In the case where the light-emitting element is in Fig.Because 1C has a microcavity structure, light (monochromatic light) of different wavelengths can be extracted, even using the same EL layer. Therefore, separate dyeing to obtain different emission colors (e.g., red, green, and blue) is unnecessary. This allows for high resolution. It should be noted that a combination with color layers (color filters) is also possible. Furthermore, the emission intensity of light of a specific wavelength can be increased in the forward direction, thereby reducing power consumption.

[0115] In one embodiment of the present invention, the light-emitting element, the first electrode 101 and / or the second electrode 102, is a translucent electrode (e.g., a transparent electrode or a transflective electrode). In the case of a transparent electrode, the transparent electrode has a visible light transmittance of 40% or higher. In the case of a translucent electrode, the transflective electrode has a visible light reflectance of 20% or higher and 80% or lower, preferably 40% or higher and 70% or lower. These electrodes preferably have a resistivity of 1 × 10⁻⁶ -2 Ωcm or less.

[0116] Furthermore, if, in the light-emitting element of an embodiment of the present invention, either the first electrode 101 or the second electrode 102 is a reflective electrode, the reflectance for visible light of the reflective electrode is higher than or equal to 40% and lower than or equal to 100%, preferably higher than or equal to 70% and lower than or equal to 100%. This electrode preferably has a resistivity of 1 × 10 -2 Ωcm or less. <<Spezifische Struktur und Herstellungsverfahren des Licht emittierenden Elements> >

[0117] Next, specific structures and manufacturing processes of light-emitting elements of embodiments of the present invention are described. It should be noted that sections designated by the same reference numeral in Fig. 1A to Fig. 1D can be labelled and described in the same way. <Erste Elektrode und zweite Elektrode>

[0118] Any of the following materials, in a suitable combination, can be used for the first electrode 101 and the second electrode 102, provided that the electrode functions can be fulfilled in the element structure described above. For example, a metal, an alloy, an electrically conductive compound, a mixture thereof, and the like can be used appropriately. In particular, an In-Sn oxide (also known as ITO), an In-Si-Sn oxide (also known as ITSO), an In-Zn oxide, an In-W-Zn oxide, or the like can be used. Furthermore, it is possible to use a metal, such as…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), or neodymium (Nd), or an alloy containing a suitable combination of any of these metals, may be used. It is also possible to use an element from Group 1 or a Group 2 element of the periodic table not described above (e.g., lithium (Li), cesium (Cs), calcium (Ca), or strontium (Sr)), a rare-earth metal such as europium (Eu) or ytterbium (Yb), an alloy containing a suitable combination of any of these elements, graphene, or the like.

[0119] If the light-emitting element is the EL layer 103 with a multilayer structure as in Fig.The first electrode 101, comprising 1C and the first electrode 101 serving as the anode, contains the hole injection layer 111 and the hole transport layer 112 of the EL layer 103, arranged sequentially over the first electrode 101 by a vacuum evaporation process. When several EL layers (103a and 103b), each having a multilayer structure, are arranged as in Fig. Two EL layers 1D are arranged one above the other, with the charge generation layer 104 located between them, and the first electrode 101 is an anode. A hole injection layer 111a and a hole transport layer 112a of the EL layer 103a are arranged sequentially over the first electrode 101 by a vacuum evaporation process. After the EL layer 103a and the charge generation layer 104 have been arranged sequentially, a hole injection layer 111b and a hole transport layer 112b of the EL layer 103b are arranged sequentially over the charge generation layer 104 in a similar manner. <Lochinjektionsschicht und Lochtransportschicht>

[0120] The hole injection layers (111, 111a and 111b) inject holes from the first electrode 101 serving as an anode and the charge generation layer (104) into the EL layers (103, 103a and 103b) and each contain a material with a high hole injection property.

[0121] Examples of materials with high hole-injection properties include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. It is also possible to use any of the phthalocyanine-based compounds, such as phthalocyanine (abbreviation: H₂Pc) and copper phthalocyanine (abbreviation: CuPc).

[0122] Other examples include aromatic amine compounds, which are low-molecular-weight compounds, such as... B. 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) and 3-[N-(1-Naphthyl)-N-(9-phenylcarbazol-3-yl)}amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

[0123] Other examples include high-molecular-weight compounds (e.g., oligomers, dendrimers, and polymers), such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: poly-TPD). Alternatively, a high-molecular-weight compound to which an acid has been added can be used, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (abbreviation: PAni / PSS).

[0124] Alternatively, a composite material containing a hole transport material and an acceptor material (an electron acceptor material) can be used as a material with high hole injection properties. In this case, the acceptor material extracts electrons from the hole transport material, so that holes are created in the hole injection layers (111, 111a and 111b) and the holes are injected via the hole transport layers (112, 112a and 112b) into the light-emitting layers (113, 113a, 113b and 113c). It should be noted that each of the hole injection layers (111, 111a and 111b) can be designed to have a single-layer structure using a composite material containing a hole transport material and an acceptor material (electron acceptor material), or a multi-layer structure consisting of a layer containing a hole transport material and a layer containing an acceptor material (electron acceptor material).

[0125] The hole transport layers (112, 112a, and 112b) transport the holes injected by the hole injection layers (111, 111a, and 111b) from the first electrode 101 and the charge generation layer 104 to the light-emitting layers (113, 113a, 113b, and 113c). It should be noted that the hole transport layers (112, 112a, and 112b) each contain a hole transport material. It is particularly preferred that the HOMO level of the hole transport material contained in the hole transport layers (112, 112a, and 112b) is equal to or close to that of the hole injection layers (111, 111a, and 111b).

[0126] Examples of the acceptor material used for the hole injection layers (111, 111a, and 111b) include an oxide of a metal belonging to one of groups 4 to 8 of the periodic table. Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among these oxides, molybdenum oxide is particularly preferred because it is stable in air, has low hygroscopic properties, and is easy to handle. Alternatively, organic acceptors, such as a quinodimethane derivative, a chloranil derivative, and a hexaazatriphenylene derivative, can be used. In particular, 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) and the like can be used.A compound in which electron-withdrawing groups are bonded to a fused aromatic ring with a multitude of heteroatoms, such as HAT-CN, is particularly preferred because it is thermally stable. A [3]radialene derivative comprising an electron-withdrawing group (especially a cyano group or a halogen group, such as a fluorine group) exhibits very high electron-accepting properties and is therefore preferred. Specific examples include α,α',α''-1,2,3-cyclopropanetriylidentris[4-cyano-2,3,5,6-tetrafluorobenzolacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidentris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzolacetonitrile] and α,α',α''-1,2,3-cyclopropanetriylidentris[2,3,4,5,6-pentafluorobenzolacetonitrile].

[0127] The hole transport materials used for the hole injection layers (111, 111a and 111b) and the hole transport layers (112, 112a and 112b) preferably have a hole mobility of greater than or equal to 1 × 10 -6 cm 2 / Vs. It should be noted that other substances can be used as long as the substances have a hole transport property that is higher than an electron transport property.

[0128] Materials preferred as hole transport materials are those that each exhibit a high hole transport property, such as a π-electron-rich heteroaromatic compound (e.g., a compound having a carbazole framework and a compound having a furan framework) and a compound having an aromatic amine framework.

[0129] Specific examples of hole transport materials include aromatic amine compounds, such as 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 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: DFLADFL), N-(9,9-Dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-Diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 4-Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 3-[4-(9-Phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn) N-(4-Biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 4,4'-Diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 4-Phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N,N'-Bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N''-Triphenyl-N,N',N''-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBAF), N-Phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-amine (abbreviation: PCBASF), 2-[N-(9-Phenylcarbazol-3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2,7-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPA2SF), N-[4-(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), and N,N'-Bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F). Further examples include compounds that each possess an aromatic amine skeleton, such as... B. 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 4,4',4''-Tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA), 4,4',4''-Tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 4,4',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: m-MTDATA), N,N'-Di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-Bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD) and 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), compounds that each have a carbazole skeleton, such as... B. 1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-Di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-Bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-Bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 3-[N-(4-Diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-Bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-Naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-Tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB) and 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), compounds each possessing a thiophene skeleton, such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), as well as compounds each possessing a furan skeleton, such as... B. 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).,

[0130] High molecular weight compounds, such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA) and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: poly-TPD), can also be used.

[0131] It should be noted that the hole transport material is not limited to the examples above and can be one of several known materials or a combination thereof when used for the hole injection layers (111, 111a and 111b) and the hole transport layers (112, 112a and 112b). It should also be noted that the hole transport layers (112, 112a and 112b) can each be formed from a plurality of layers. That is to say, for example, that the hole transport layers can each have a multilayered structure consisting of a first hole transport layer and a second hole transport layer.

[0132] The light-emitting element in Fig.In step 1D, the light-emitting layer 113a is formed over the hole transport layer 112a of the EL layer 103a by a vacuum evaporation process. After the EL layer 103a and the charge generation layer 104 have been formed, the light-emitting layer 113b is formed over the hole transport layer 112b of the EL layer 103b by a vacuum evaporation process. <Licht emittierende Schicht>

[0133] The light-emitting layers (113, 113a, 113b, and 113c) each contain a light-emitting substance. It should be noted that the light-emitting substance used is a substance whose emission color is blue, violet, blue-violet, green, yellow-green, yellow, orange, red, or the like. If the multiple light-emitting layers (113a, 113b, and 113c) are formed using different light-emitting substances, different emission colors can be produced (for example, complementary emission colors are combined to obtain white light emission). Furthermore, a multilayer structure can be used in which a light-emitting layer contains two or more types of light-emitting substances.

[0134] The light-emitting layers (113, 113a, 113b and 113c) can each contain, in addition to a light-emitting substance (guest material), one or more types of organic compounds (a host material and an auxiliary material). The hole transport material and / or the electron transport material described in this embodiment can be used as one or more types of organic compounds.

[0135] The light-emitting substance that can be used for the light-emitting layers (113, 113a, 113b and 113c) is not particularly limited, and a light-emitting substance that converts singlet excitation energy into light emission in the visible light range or a light-emitting substance that converts triplet excitation energy into light emission in the visible light range can be used. The organic compound of one embodiment of the present invention emits fluorescence and can therefore be used as a light-emitting substance that converts singlet excitation energy into light emission in the visible light range. Further examples of the aforementioned light-emitting substances are given below.

[0136] As an example of a light-emitting substance that converts singlet excitation energy into light emission, a substance that emits fluorescence (fluorescent material) can be given. Examples of substances that emit fluorescence include a pyrene derivative, an anthracene derivative, a triphenylene derivative, a fluorene derivative, a carbazole derivative, a dibenzothiophene derivative, a dibenzofuran derivative, a dibenzoquinoxaline derivative, a quinoxaline derivative, a pyridine derivative, a pyrimidine derivative, a phenanthrene derivative, and a naphthalene derivative. A pyrene derivative is particularly preferred because it exhibits a high emission quantum yield.Specific examples of the pyrene derivative include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (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'-bis(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]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02) and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03).

[0137] Furthermore, it is possible to obtain 5,6-Bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-Bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-Bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA), Perylene, 2,5,8,11-Tetra(tert-butyl)perylene (abbreviation: TBP), N,N''-(2-tert-Butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-Diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N-[4-(9,to use 10-Diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) or the like.

[0138] Examples of light-emitting substances that convert triplet excitation energy into light emission include a substance that emits phosphorescence (phosphorescent material) and a thermally activated delayed fluorescence (TADF) material that exhibits thermally activated delayed fluorescence.

[0139] Examples of phosphorescent materials include a metal-organic complex, a metal complex (platinum complex), and a rare-earth metal complex. These substances exhibit their respective emission colors (emission peaks), and any one of them is selected appropriately depending on the requirements.

[0140] Examples of phosphorescent materials that emit blue or green light and whose emission spectrum has a peak wavelength greater than or equal to 450 nm and less than or equal to 570 nm include the following substances.

[0141] For example, organometallic complexes with a 4H-triazole skeleton, such as 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-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]) and Tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz)3]), organometallic complexes with a 1H-triazole skeleton, such as... B. Tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) and Tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), organometallic complexes with an imidazole skeleton, such asfac-Tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]) and Tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), and organometallic complexes in which a phenylpyridine derivative with an electron-withdrawing group is a ligand, such as Bis[2-(4',6'-difluorophenyl)pyridinato-N,C. 2' ]iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' ]iridium(III)picolinate (abbreviation: Firpic), Bis{2-[3' ,5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2'}iridium(III)picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) and Bis[2-(4',6'difluorophenyl)pyridinato-N,C 2' ]iridium(III)acetylacetonate (abbreviation: Flr(acac)).

[0142] Examples of phosphorescent materials that emit green or yellow light and whose emission spectrum has a peak wavelength greater than or equal to 495 nm and less than or equal to 590 nm include the following substances.

[0143] For example, organometallic complexes with a pyrimidine backbone, such as... B. Tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (Acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (Acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (Acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (Acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (Abbreviation: [Ir(mpmppm)2(acac)]), (Acetylacetonato)bis {4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN 3]phenyl-κC}iridium(III) (abbreviation: [Ir(dmppm-dmp)2(acac)]) and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), organometallic complexes with a pyrazine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), organometallic complexes with a pyridine skeleton, such as Tris(2-phenylpyridinato-N,C 2' )iridium(III) (abbreviation: [Ir(ppy)3]), Bis(2-phenylpyridinato-N,C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), Bis(benzo[h]quinolinato)iridium(III)acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), Tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), Tris(2-phenylquinolinato-N,C 2' )iridium(III) (abbreviation: [Ir(pq)3]) and bis(2-phenylquinolinato-N,C 2')iridium(III)acetylacetonate (abbreviation: [Ir(pq)2(acac)]), organometallic complexes, such as bis(2,4-diphenyl-1,3-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)]) and bis(2-phenylbenzothiazolato-N,C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(bt)2(acac)]), as well as a rare earth metal complex, such as Tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]).

[0144] Examples of phosphorescent materials that emit yellow or red light and whose emission spectrum has a peak wavelength greater than or equal to 570 nm and less than or equal to 750 nm include the following substances.

[0145] For example, organometallic complexes with a pyrimidine framework, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]) and (dipivaloylmethanato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), can be organometallic complexes with a pyrazine framework, such as... B. (Acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), Bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]) and (Acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), organometallic complexes with a pyridine skeleton, such as Tris(1-phenylisoquinolinato-N,C 2' )iridium(III) (abbreviation: [Ir(piq)3]) and bis(1-phenylisoquinolinato-N,C 2')iridium(III)acetylacetonate (abbreviation: [Ir(piq)2(acac)]), a platinum complex, such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatin(II) (abbreviation: [PtOEP]), and rare earth metal complexes, such as Tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]) and Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]).

[0146] The organic compounds used in the light-emitting layers (113, 113a, 113b, and 113c) are one or more types of substances that have a larger energy gap than the light-emitting substance (the guest material). It should be noted that any of the hole transport materials listed above and the electron transport materials specified below can be used as organic compounds (as host and guest material). Since the organic compound of an embodiment of the present invention has a low LUMO level, using the organic compound as the host and guest material can lower the drive voltage. The relatively high T1 level described above is also a property required for the organic compound.Due to its low LUMO level, this organic compound can be used as one of the organic compounds forming an exciplex in combination with any number of different materials. With reference to further materials as examples, the properties required for the organic compounds (the host material and the excipient) are described in detail.

[0147] If the light-emitting substance is a fluorescent material, an organic compound is preferably used as the host material, exhibiting a high energy level in a singlet excitation state and a low energy level in a triplet excitation state. It should be noted that, in addition to the hole-transporting materials and electron-transporting materials described in this embodiment, a bipolar material can be used as the host material, and a substance that meets the aforementioned conditions is preferred. For example, an anthracene derivative and a tetracene derivative are also preferred.

[0148] Therefore, examples of the host material used in combination with a fluorescent substance include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), PCPN, CzPA, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: FLPPA), 5,12-diphenyltetracene, and 5,12-Bis(biphenyl-2-yl)tetracene.

[0149] In the case where the light-emitting substance is a phosphorescent material, an organic compound with a triplet excitation energy (energy difference between a ground state and a triplet excitation state) higher than that of the light-emitting substance is selected as the host material. It should be noted that, in addition to the hole-transporting materials and electron-transporting materials described in this embodiment, a bipolar material can be used as the host material, and a substance that meets the aforementioned conditions is preferred. For example, condensed polycyclic aromatic compounds, such as an anthracene derivative, a phenanthrene derivative, a pyrene derivative, a chrysene derivative, and a dibenzo[g,p]chrysene derivative, are also preferred.

[0150] Therefore, examples of the host material used in combination with a phosphorescent substance include 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, 9-(4-{4'-[N-phenyl-N-(N-phenyl-3-carbazolyl)]amino}phenyl)phenyl-10-phenylanthracene (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA). 6,12-Dimethoxy-5,11-diphenylchrysene, N,N,N',N',N',N'',N'',N'''',N'''-Octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), CzPA, 3,6-Diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-Di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-Bianthryl (abbreviation: BANT) 9,9'-(Stilben-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(Stilben-4,4'-diyl)diphenanthrene (abbreviation: DPNS2) and 1,3,5-Tri(1-pyrenyl)benzene (abbreviation: TPB3).,

[0151] In cases where a variety of organic compounds are used for the light-emitting layers (113, 113a, 113b, and 113c), compounds forming an exciplex are preferably used in combination with a phosphorescent substance. With such a structure, light emission can be achieved through exciplex triplet energy transfer (ExTET), which is the transfer of energy from an exciplex to a light-emitting substance. In this case, any number of different organic compounds can be combined in a suitable manner to efficiently form an exciplex; in particular, a compound that readily accepts holes (hole transport material) and a compound that readily accepts electrons (electron transport material) are preferably combined.

[0152] The TADF material can up-convert a triplet excitation state to a singlet excitation state (i.e., reverse intersystem crossing is possible) using little thermal energy, and it can efficiently emit light (fluorescence) from the singlet excitation state. TADF is efficiently maintained under the following condition: the energy difference between the triplet excitation level and the singlet excitation level is greater than or equal to 0 eV and less than or equal to 0.2 eV, preferably greater than or equal to 0 eV and less than or equal to 0.1 eV. It should be noted that "delayed fluorescence" emitted by the TADF material refers to light emission that has the same spectrum as normal fluorescence and a very long lifetime. The lifetime is 1 × 10⁻⁶ -6 Seconds or longer, preferably 1 × 10 -3 Seconds or longer.

[0153] Examples of TADF materials include fullerene, a fullerene derivative, an acridine derivative such as proflavine, and eosin. Other examples include metal-containing porphyrins, such as porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of metal-containing porphyrins include a protoporphyrin tin fluoride complex (abbreviation: SnF2(Proto IX)), a mesoporphyrin tin fluoride complex (abbreviation: SnF2(Meso IX)), a hematoporphyrin tin fluoride complex (abbreviation: SnF2(Hämato IX)), a coproporphyrin tetramethyl ester tin fluoride complex (abbreviation: SnF2(Copro III-4Me)), an octaethylporphyrin tin fluoride complex (abbreviation: SnF2(OEP)), an etioporphyrin tin fluoride complex (abbreviation: SnF2(Etio I)) and an octaethylporphyrin platinum chloride complex (abbreviation: PtCl2OEP).

[0154] Other examples of TADF material include heterocyclic compounds, each containing a π-electron-rich heteroaromatic ring and a π-electron-poor heteroaromatic ring, such as... B. 2-(Biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-Dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), Bis[4-(9,9-dimethyl-9,10-dihydroacridin)phenyl]sulfone (abbreviation: DMAC-DPS) and 10-Phenyl-10H, 10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA).It should be noted that a substance in which the π-electron-rich heteroaromatic ring is directly bonded to the π-electron-poor heteroaromatic ring is particularly preferred, since this increases both the donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-poor heteroaromatic ring, and reduces the energy difference between the singlet excitation state and the triplet excitation state.

[0155] It should be noted that if a TADF material is used, the TADF material can be used in combination with another organic compound.

[0156] By using the above materials in a suitable manner, the light-emitting layers (113, 113a, 113b and 113c) can be formed. Furthermore, when the above materials are used in combination with a low-molecular-weight material or a high-molecular-weight material, they can be used to form the light-emitting layers (113, 113a, 113b and 113c).

[0157] The light-emitting element in Fig. In step 1D, the electron transport layer 114a is formed above the light-emitting layer 113a of the EL layer 103a. After the EL layer 103a and the charge-generating layer 104 have been formed, the electron transport layer 114b is formed above the light-emitting layer 113b of the EL layer 103b. <elektronentransportschicht>

[0158] The electron transport layers (114, 114a, and 114b) transport the electrons injected from the second electrode 102 through the electron injection layers (115, 115a, and 115b) to the light-emitting layers (113, 113a, 113b, and 113c). It should be noted that the electron transport layers (114, 114a, and 114b) each contain an electron transport material. The electron transport materials contained in the electron transport layers (114, 114a, and 114b) are preferably substances with an electron mobility of 1 × 10⁻⁶ or higher. -6 cm 2 / Vs. It should be noted that other substances can also be used, provided they have an electron transport property that is higher than their hole transport property. The organic compound of one embodiment of the present invention meets these requirements. Furthermore, the low LUMO level of the organic compound contributes to lowering the drive voltage; therefore, the organic compound is preferably used for the electron transport layers. Further examples of materials that can be used for the electron transport layers are given below.

[0159] Any of the following materials with high electron transport properties can be used as an electron transport material: a metal complex with a quinoline framework, a metal complex with a benzoquinoline framework, a metal complex with an oxazole framework, a metal complex with a thiazole framework, an oxadiazole derivative, a triazole derivative, an imidazole derivative, an oxazole derivative, a thiazole derivative, a phenanthroline derivative, a quinoline derivative with a quinoline ligand, a benzoquinoline derivative, a quinoxaline derivative, a dibenzoquinoxaline derivative, a pyridine derivative, a bipyridine derivative, a pyrimidine derivative, and a π-electron-deficient heteroaromatic compound, such as a nitrogen-containing heteroaromatic compound.

[0160] Specific examples of the electron transport material include metal complexes with a quinoline or benzoquinoline framework, such as tris(8-quinolinolato)aluminium(III) (abbreviation: Alq3), tris(4-methyl-8-quinolinolato)aluminium(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminium(III) (abbreviation: BAlq) and bis(8-quinolinolato)zinc(II) (abbreviation: Znq), as well as metal complexes with an oxazole or thiazole framework, such as... B. Bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), Bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ) and Bis[2-(2-hydroxyphenyl)benzothiazolato]zinc(II) (abbreviation: Zn(BTZ)2).

[0161] It is possible to use, in addition to the metal complexes, oxadiazole derivatives, such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7) and 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), triazole derivatives, such as... B. 3-(4'-tert-butylphenyl)-4-phenyl-5-(4''-biphenyl)-1,2,4-triazole (abbreviation: TAZ) and 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), imidazole derivatives (including benzimidazole derivatives), such as 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI) and 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), an oxazole derivative, such as... B. 4,4'-Bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOS), phenanthroline derivatives, such asBathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP) and 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), quinoxaline derivatives and dibenzoquinoxaline derivatives, such as... B. 2-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-Carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-Diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II) and 6-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[fh]quinoxaline (abbreviation: 6mDBTPDBq-II), pyridine derivatives, such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) and 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), pyrimidine derivatives, such as4,6-Bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-Bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II) and 4,6-Bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), as well as triazine derivatives, such as... B. 2-{4-[3-(N-Phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) and 9-[3-(4,6-Diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), to use.

[0162] As another alternative, a high molecular weight compound such as poly(2,5-pyridindiyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can be used.

[0163] Each of the electron transport layers (114, 114a and 114b) is not limited to a single layer and can be a layer arrangement of two or more layers, each containing any one of the aforementioned substances.

[0164] The light-emitting element in Fig. In step 1D, the electron injection layer 115a is next formed over the electron transport layer 114a of the EL layer 103a by a vacuum evaporation process. Subsequently, the EL layer 103a and the charge generation layer 104 are formed, the components up to the electron transport layer 114b of the EL layer 103b are formed, and then the electron injection layer 115b is formed over it by a vacuum evaporation process. <elektroneninjektionsschicht>

[0165] The electron injection layers (115, 115a and 115b) each contain a substance with high electron injection properties. The electron injection layers (115, 115a and 115b) can each be made using an alkali metal, an alkaline earth metal or a compound thereof, such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF₂) or lithium oxide (LiO₂). x ). A rare-earth metal compound such as erbium fluoride (ErF3) can also be used. An electride can also be used for the electron injection layers (115, 115a, and 115b). Examples of the electride include a substance in which electrons are added to calcium oxide-aluminum oxide at a high concentration. Any of the substances mentioned above that are used for the electron transport layers (114, 114a, and 114b) can also be used.

[0166] A composite material containing an organic compound and an electron donor can also be used for the electron injection layers (115, 115a, and 115b). Such a composite material exhibits high electron injection and electron transport properties because the electron donor generates electrons in the organic compound. Here, the organic compound is preferably a material that can transport the generated electrons exceptionally well. In particular, the electron transport materials used for the electron transport layers (114, 114a, and 114b), such as a metal complex or a heteroaromatic compound, can be used. The electron donor can be a substance that exhibits electron-donating properties with respect to the organic compound.Preferred examples are an alkali metal, an alkaline earth metal, and a rare earth metal. Specifically, lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like may be specified. Furthermore, an alkali metal oxide and an alkaline earth metal oxide are preferred, and lithium oxide, calcium oxide, barium oxide, and the like may be specified. Alternatively, a Lewis base, such as magnesium oxide, may be used. As a further alternative, an organic compound, such as tetrathiafulvalene (abbreviation: TTF), may be used.

[0167] In the case where light emitted by the light-emitting layer 113b reaches the light-emitting element in Fig. When the 1D signal is amplified, the optical path length between the second electrode 102 and the light-emitting layer 113b is preferably less than a quarter of the wavelength λ of the light emitted by the light-emitting layer 113b. In this case, the optical path length can be adjusted by changing the thickness of the electron transport layer 114b or the electron injection layer 115b. < Charge generation layer>

[0168] The light-emitting element in Fig. In 1D, the charge-generating layer 104 has a function for injecting electrons into the EL layer 103a and for injecting holes into the EL layer 103b when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. The charge-generating layer 104 can have either a structure in which an electron acceptor is added to a hole transport material or a structure in which an electron donor is added to an electron transport material. Alternatively, both of these structures can be stacked on top of each other. It should be noted that forming the charge-generating layer 104 using any of the aforementioned materials can suppress a rise in the drive voltage that results from stacking the EL layers.

[0169] In the case where the charge-generating layer 104 has a structure in which an electron acceptor is added to a hole-transporting material, any of the materials described for this embodiment can be used as the hole-transporting material. It is possible to use 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, and the like as electron acceptors. Furthermore, oxides of metals belonging to groups 4 to 8 of the periodic table can be specified. Specific examples are vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide.

[0170] In the case where the charge-generating layer 104 has a structure in which an electron donor is added to an electron transport material, any of the materials described in this embodiment can be used as the electron transport material. It is possible to use an alkali metal, an alkaline earth metal, a rare earth metal, metals belonging to groups 2 and 13 of the periodic table, or an oxide or carbonate thereof as the electron donor. In particular, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, or the like are preferably used. An organic compound, such as tetrathianaphthacene, can be used as the electron donor. <substrat>

[0171] The light-emitting element described in this embodiment can be formed on any number of different substrates. It should be noted that the substrate type is not limited to any one particular type. Examples of substrates include semiconductor substrates (e.g., a single-crystal substrate and a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate containing a stainless steel foil, a tungsten substrate, a substrate containing a tungsten foil, a flexible substrate, a mounting film, paper containing a fiber material, and a base material film.

[0172] Examples of the glass substrate include barium borosilicate glass, aluminum borosilicate glass, and soda-lime glass. Examples of the flexible substrate, affixing film, and base material film include plastics, typically polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES); a synthetic resin, such as an acrylic resin, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, an aramid resin, an epoxy resin, an evaporation-deposited inorganic film, and paper.

[0173] For the fabrication of the light-emitting element of this embodiment, a vacuum process, such as an evaporation process, or a solution process, such as a rotational coating process or an inkjet process, can be used. If an evaporation process is used, a physical vapor deposition (PVD) process, such as a sputtering process, an ion plating process, an ion beam evaporation process, a molecular beam evaporation process, or a vacuum evaporation process, a chemical vapor deposition (CVD) process, or the like can be employed.In particular, the functional layers contained in the EL layers (the hole injection layers (111, 111a and 111b), the hole transport layers (112, 112a and 112b), the light-emitting layers (113, 113a, 113b and 113c), the electron transport layers (114, 114a and 114b) and the electron injection layers (115, 115a and 115b)) as well as the charge generation layers (104, 104a and 104b) in the light-emitting element can be deposited by an evaporation process (e.g. a vacuum evaporation process), a coating process (e.g. a dip coating process, a nozzle coating process, a rod coating process, a rotary coating process or a spray coating process), a printing process (e.g. an inkjet process, screen printing (stencil printing), an offset printing process) (Flat printing), flexographic printing (relief printing), gravure printing, microcontact printing or nanoembossing lithography) or the like.

[0174] It should be noted that materials that can be used for the functional layers contained in the EL layers (103, 103a and 103b) (the hole injection layers (111, 111a and 111b), the hole transport layers (112, 112a and 112b), the light-emitting layers (113, 113a, 113b and 113c), the electron transport layers (114, 114a and 114b) and the electron injection layers (115, 115a and 115b)) as well as the charge generation layers (104, 104a and 104b) of the light-emitting element described in this embodiment are not limited to the materials listed above, and other materials can be used in combination, as long as the functions of the layers are ensured. For example, a high-molecular-weight compound (e.g.,An oligomer, a dendrimer, or a polymer), a medium-molecular-weight compound (a compound between a low-molecular-weight compound and a high-molecular-weight compound with a molecular weight of 400 to 4000), or an inorganic compound (e.g., a quantum dot material) can be used. The quantum dot material can be a gelatinous quantum dot material, an alloyed quantum dot material, a core-shell quantum dot material, a core-quantum quantum dot material, or the like.

[0175] The structures described in this embodiment can be combined in a suitable manner with one of the structures described in the other embodiments. (Version 3)

[0176] This embodiment describes a light-emitting device of an embodiment of the present invention. It should be noted that a light-emitting device which is in Fig. Figure 2A shows a light-emitting active matrix device in which transistors (FETs) 202 are electrically connected to light-emitting elements (203R, 203G, 203B, and 203W) on a first substrate 201. The light-emitting elements (203R, 203G, 203B, and 203W) include a common EL layer 204 and each has a microcavity structure in which the optical path length between electrodes is adapted according to the emission color of the light-emitting element. The light-emitting device is a top-emission light-emitting device in which light is emitted from the EL layer 204 through color filters (206R, 206G, and 206B) formed on a second substrate 205.

[0177] The in Fig. The light-emitting device shown in Figure 2A is manufactured such that a first electrode 207 serves as a reflective electrode and a second electrode 208 serves as a transflective electrode. It should be noted that, with regard to the electrode materials for the first electrode 207 and the second electrode 208, reference may be made, if necessary, to the description of one of the other embodiments.

[0178] In the case where, for example, Fig. 2A where the light-emitting element 203R serves as a red light-emitting element, the light-emitting element 203G serves as a green light-emitting element, the light-emitting element 203B serves as a blue light-emitting element, and the light-emitting element 203W serves as a white light-emitting element, is, as in Fig. Figure 2B shows a distance between the first electrode 207 and the second electrode 208 in the light-emitting element 203R adjusted to obtain an optical path length of 200R, a distance between the first electrode 207 and the second electrode 208 in the light-emitting element 203G is adjusted to obtain an optical path length of 200G, and a distance between the first electrode 207 and the second electrode 208 in the light-emitting element 203B is adjusted to obtain an optical path length of 200B. It should be noted that the optical adjustment can be carried out such that, as shown in Fig. Figure 2B shows that a conductive layer 210R is arranged over the first electrode 207 in the light-emitting element 203R and a conductive layer 210G is arranged over the first electrode 207 in the light-emitting element 203G.

[0179] The second substrate 205 is equipped with the color filters (206R, 206G and 206B). It should be noted that the color filters each transmit visible light in a specific wavelength range and block visible light in a specific wavelength range. Therefore, as in Fig. Figure 2A shows the color filter 206R, which transmits only light in the red wavelength range, positioned so that it overlaps the light-emitting element 203R, thus enabling red light emission from the light-emitting element 203R. Similarly, the color filter 206G, which transmits only light in the green wavelength range, is positioned so that it overlaps the light-emitting element 203G, thus enabling green light emission from the light-emitting element 203G. Finally, the color filter 206B, which transmits only light in the blue wavelength range, is positioned so that it overlaps the light-emitting element 203B, thus enabling blue light emission from the light-emitting element 203B. It should be noted that the light-emitting element 203W can emit white light without a color filter.It should be noted that a black layer (black matrix) 209 may be provided at one end section of each color filter. The color filters (206R, 206G and 206B) and the black layer 209 may be covered with a cover layer formed using a transparent material.

[0180] Although the light-emitting device in Fig. 2A has a structure in which light is extracted from the side of the second substrate 205 (top-emission structure), as shown in Fig. Figure 2C shows a structure in which light is extracted from the side of the first substrate 201, above which the FETs 202 are formed (bottom-emission structure). In the case of a light-emitting bottom-emission device, the first electrode 207 is configured as a transflective electrode and the second electrode 208 is configured as a reflective electrode. The first substrate 201 is a substrate that has at least a certain light transmittance. As shown in Fig. As shown in 2C, color filters (206R', 206G' and 206B') are provided closer to the first substrate 201 than the light-emitting elements (203R, 203G and 203B).

[0181] In Fig. 2A The light-emitting elements are the red light-emitting element, the green light-emitting element, the blue light-emitting element, and the white light-emitting element; however, the light-emitting elements of an embodiment of the present invention are not limited to the foregoing, and a yellow light-emitting element or an orange light-emitting element may be used. It should be noted that with regard to the materials used for the EL layers (a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like), reference may be made, as needed, to the description of one of the other embodiments in order to fabricate each of the light-emitting elements.In this case, a color filter must be selected appropriately according to the emission color of the light-emitting element.

[0182] The above structure can be used to manufacture a light-emitting device that includes light-emitting elements exhibiting a variety of emission colors.

[0183] It should be noted that the structures described in this embodiment can be combined with any of the structures described in the other embodiments as required. (Version 4)

[0184] This embodiment describes a light-emitting device of an embodiment of the present invention.

[0185] The use of the element structure of the light-emitting element in one embodiment of the present invention enables the fabrication of a light-emitting active-matrix device or a light-emitting passive-matrix device. It should be noted that a light-emitting active-matrix device has a structure comprising a combination of a light-emitting element and a transistor (FET). Therefore, a light-emitting passive-matrix device and a light-emitting active-matrix device are each embodiments of the present invention. It should be noted that any of the light-emitting elements described in the other embodiments can be used in the light-emitting device described in this embodiment.

[0186] In this embodiment, a light-emitting active matrix device is used based on Fig. 3A and Fig. 3B described.

[0187] Fig. 3A is a top view showing a light-emitting device 21, and Fig. 3B is a cross-sectional view along the catenary AA' in Fig. 3A. The light-emitting active matrix device comprises a pixel section 302, a driver circuit section (source line driver circuit) 303, and driver circuit sections (gate line driver circuits) (304a and 304b), which are provided above a first substrate 301. The pixel section 302 and the driver circuit sections (303, 304a, and 304b) are sealed with a sealant 305 between the first substrate 301 and a second substrate 306.

[0188] A connecting line 307 is provided above the first substrate 301. The connecting line 307 is electrically connected to an FPC 308, which is an external input terminal. It should be noted that the FPC 308 transmits a signal (e.g., a video signal, a clock signal, a start signal, or a reset signal) or a potential from outside to the driver circuit sections (303, 304a, and 304b). The FPC 308 may be provided with a printed circuit board (PWB). It should be noted that the light-emitting device provided with an FPC or a PWB is included in the category of a light-emitting device.

[0189] Fig. Figure 3B represents a cross-sectional structure of the light-emitting device.

[0190] Pixel section 302 contains a plurality of pixels, each containing a switching FET 311, a current-controlling FET 312, and a first electrode 313 electrically connected to FET 312. It should be noted that the number of FETs contained in each pixel is not particularly limited and can be adjusted as appropriate.

[0191] For example, FETs 309, 310, 311, and 312 can be used as staggered transistors or inverted staggered transistors without any particular restrictions. A top-gate transistor, a bottom-gate transistor, or the like can be used.

[0192] It should be noted that there is no particular restriction regarding the crystallinity of a semiconductor that can be used for FETs 309, 310, 311, and 312; an amorphous semiconductor or a semiconductor with crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single-crystal semiconductor, or a semiconductor that partially contains crystalline regions) can be used. Preferably, a semiconductor with crystallinity is used, in which case a deterioration of the transistor properties can be prevented.

[0193] The semiconductor can be, for example, an element from group 14, a compound semiconductor, an oxide semiconductor, an organic semiconductor, or the like. Typical examples include a semiconductor containing silicon, a semiconductor containing gallium arsenide, or an oxide semiconductor containing indium.

[0194] The driver circuit section 303 includes the FET 309 and the FET 310. The FET 309 and the FET 310 can be implemented with a circuit containing transistors of the same line type (either n-channel or p-channel transistors), or with a CMOS circuit containing one n-channel transistor and one p-channel transistor. Alternatively, a driver circuit can be provided externally.

[0195] An end section of the first electrode 313 is covered with an insulator 314. The insulator 314 can be formed using an organic compound, such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin), or an inorganic compound, such as silicon dioxide, silicon oxynitride, or silicon nitride. An upper end section or a lower end section of the insulator 314 preferably has a curved surface. In this case, an advantageous covering can be obtained with a film formed over the insulator 314.

[0196] An EL layer 315 and a second electrode 316 are arranged above the first electrode 313. The EL layer 315 comprises a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like.

[0197] The structure and materials described in one of the other embodiments can be used for the components of a light-emitting element 317 described in this embodiment. Although not shown, the second electrode 316 is electrically connected to the FPC 308, which is an external input terminal.

[0198] Although the cross-sectional view in Fig. While 3B represents only a single light-emitting element 317, a multitude of light-emitting elements are arranged in a matrix within pixel section 302. Light-emitting elements emitting light of three types of colors (R, G, and B) are selectively formed within pixel section 302, thereby creating a light-emitting device capable of displaying a full-color image. In addition to the light-emitting elements emitting light of three types of colors (R, G, and B), light-emitting elements emitting light of white (W), yellow (Y), magenta (M), cyan (C), and the like can be formed. For example, the light-emitting elements emitting light of some of the aforementioned colors are used in combination with the light-emitting elements emitting light of three types of colors (R, G, and B), resulting in effects such as...An improvement in color purity and a reduction in power consumption can be achieved. Alternatively, a light-emitting device capable of displaying a full-color image can be produced by combining it with color filters. Red (R), green (G), blue (B), cyan (C), magenta (M), and yellow (Y) color filters, and the like, can be used as color filters.

[0199] When the second substrate 306 and the first substrate 301 are joined together with the sealant 305, the FETs (309, 310, 311, and 312) and the light-emitting element 317 are positioned above the first substrate 301 in a space 318 enclosed by the first substrate 301, the second substrate 306, and the sealant 305. It should be noted that the space 318 can be filled with an inert gas (e.g., nitrogen or argon) or an organic substance (including the sealant 305).

[0200] For the sealant 305, an epoxy-based resin, a glass frit, or the like can be used. Preferably, a material with minimal moisture and oxygen permeability is used for the sealant 305. The second substrate 306 can be a substrate that can be used as the first substrate 301, in a similar manner. Therefore, any of the numerous substrates described in the other embodiments can be used appropriately. The substrate can be a glass substrate, a quartz substrate, or a plastic substrate made of fiber-reinforced plastic (FRP), polyvinyl fluoride (PVF), polyester, an acrylic resin, or the like. In the case where a glass frit is used for the sealant, the first substrate 301 and the second substrate 306 are preferably glass substrates with regard to adhesion.

[0201] In this way, the light-emitting active matrix device can be obtained.

[0202] In cases where the light-emitting active matrix device is deployed over a flexible substrate, the FETs and the light-emitting element can be formed directly over the flexible substrate. Alternatively, the FETs and the light-emitting element can be formed over a substrate containing a separating layer and then separated by applying heat, force, laser light, or the like to the separating layer to transfer them to the flexible substrate. The separating layer could, for example, be a layer arrangement comprising inorganic films, such as a tungsten film and a silicon oxide film, or an organic resin film made of polyimide or the like.Examples of flexible substrates include, 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 fabric substrate (including a natural fiber (e.g., silk, cotton, or hemp), a synthetic fiber (e.g., nylon, polyurethane, or polyester), a regenerated fiber (e.g., acetate, cupro, viscose, or regenerated polyester), or the like), a leather substrate, and a rubber substrate. Using any of these substrates, an increase in service life, an increase in heat resistance, a reduction in weight, and a reduction in thickness can be achieved.

[0203] It should be noted that the structures described in this embodiment can be combined with any of the structures described in the other embodiments as required. (Version 5)

[0204] In this embodiment, examples of various electronic devices and a vehicle are described, which are manufactured using the light-emitting element of an embodiment of the present invention or a light-emitting device incorporating the light-emitting element of an embodiment of the present invention. It should be noted that the light-emitting device can be used primarily in a display section of the electronic device described in this embodiment.

[0205] Electronic devices that are in Fig. 4A to Fig. The components shown in Figure 4C may include a housing 7000, a display section 7001, a loudspeaker 7003, an LED lamp 7004, operating buttons 7005 (including a power switch or an operating switch), a connection port 7006, a sensor 7007 (a sensor with a function for measuring or detecting force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electrical power, radiation, flow rate, humidity, gradient, vibration, odor or infrared rays), a microphone 7008 and the like.

[0206] Fig. 4A represents a portable computer which, in addition to the above components, may include a 7009 switch, a 7010 infrared connector, and the like.

[0207] Fig. 4B represents a portable image display device (e.g. a DVD player) which is equipped with a storage medium and may, in addition to the components mentioned above, include a second display section 7002, a storage medium read section 7011 and the like.

[0208] Fig. 4C represents a digital camera which has a television reception function and may, in addition to the above components, include an antenna 7014, a release button 7015, an image reception section 7016 and the like.

[0209] Fig. 4D represents a portable information terminal. The portable information terminal has a function for displaying information on three or more surfaces of the display section 7001. Here, information 7052, information 7053, and information 7054 are displayed on different surfaces. For example, a user of the portable information terminal can check information 7053, which is displayed in such a way that it can be viewed from above the portable information terminal, with the portable information terminal kept in a breast pocket of their clothing. Thus, for example, the user can see the display without removing the portable information terminal from the pocket and can decide whether to answer the call.

[0210] Fig. 4E represents a portable information terminal (e.g., a smartphone) and may include the display section 7001, the control buttons 7005, and the like within the housing 7000. It should be noted that the portable information terminal may include a speaker, a connection port, a sensor, or the like. The portable information terminal can display text and image data on its various surfaces. Here, three icons 7050 are shown. Additionally, information 7051, represented by dashed rectangles, may be displayed on another surface of the display section 7001. Examples of the information 7051 include notification of the arrival of an email, SNS message, or call; the subject and sender of an email, SNS message, or the like; the date; the time; the remaining battery power; and the signal strength of an antenna.The icon 7050 or similar can be displayed in the place where the information 7051 is displayed.

[0211] Fig. 4F represents a large television set (also called a TV or television receiver) and may include the housing 7000, the display section 7001, and the like. The housing 7000 is also shown here supported by a stand 7018. The television set can be operated with a separate remote control 7111 or the like. The display section 7001 may include a touch sensor. The television set can be operated by touching the display section 7001 with a finger or the like. The remote control 7111 may be equipped with a display section for showing information output by the remote control 7111. The television channels and volume can be controlled by means of control buttons or a touchscreen on the remote control 7111, and images displayed on the display section 7001 can be controlled.

[0212] The in Fig. 4A to Fig. The electronic devices shown in Figure 4F may have various functions, such as a function to display various information (a still image, a moving image, a text image, and the like) on a display section, a touchscreen function, a function to display a calendar, date, time, and the like, a function to control processing by means of various types of software (programs), a wireless communication function, a function to connect to various computer networks by means of a wireless communication function, a function to transmit and receive various data by means of a wireless communication function, a function to read a program or data that is / are stored in a storage medium and to display the program or data on the display section, and the like.Furthermore, the electronic device, which includes a multitude of display sections, may have the following functions: a function for displaying image data mainly on one display section while text data is mainly displayed on another display section; a function for displaying a three-dimensional image by displaying images on a multitude of display sections, taking into account parallax or the like.Furthermore, the electronic device, which includes an image reception section, may have the following functions: a function for capturing a still image, a function for capturing a moving image, a function for automatically or manually correcting a captured image, a function for saving a captured image to a storage medium (an external storage medium or a storage medium built into the camera), a function for displaying a captured image on the display section, or the like. It should be noted that functions that are intended for the [missing information] are not included. Fig. 4A to Fig. The electronic devices shown in 4F can be provided, are not limited to those described above, and the electronic devices can have various functions.

[0213] Fig. 4G is a wristwatch-like portable information terminal, which can be used, for example, as a smartwatch. The wristwatch-like portable information terminal includes the housing 7000, the display section 7001, control buttons 7022 and 7023, a connection port 7024, a band 7025, a microphone 7026, a sensor 7029, a speaker 7030, and the like. The display surface of the display section 7001 is curved, and images can be displayed on this curved surface. Furthermore, two-way communication is possible between the portable information terminal and, for example, a headset suitable for wireless communication, thus enabling hands-free operation using the portable information terminal. It should be noted that the connection port 7024 allows for two-way data transmission with another information terminal as well as charging.Wireless power supply can also be used during the charging process.

[0214] The display section 7001, mounted in the housing 7000 which serves as a frame, comprises a non-rectangular display area. The display section 7001 can display an icon 7027, which shows the time, another icon 7028, and the like. The display section 7001 can be a touchscreen (input / output device) that includes a touch sensor (input device).

[0215] The smartwatch, which is in Fig. 4G, as depicted, can have various functions, such as a function to display various information (e.g., a still image, a moving image, and a text image) on the display section, a touchscreen function, a function to display a calendar, date, time, and the like, a function to control processing using various types of software (programs), a wireless communication function, a function to connect to various computer networks using a wireless communication function, a function to transmit and receive various data using a wireless communication function, a function to read a program or data stored in a storage medium and to display the program or data on the display section, and the like.

[0216] The housing 7000 can contain a loudspeaker, a sensor (a sensor with a function to measure or detect force, displacement, position, speed, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electrical power, radiation, flow rate, humidity, gradient, vibration, odor or infrared rays), a microphone and the like.

[0217] It should be noted that the light-emitting device of an embodiment of the present invention and the display device comprising the light-emitting element of an embodiment of the present invention can be used in the display section of each of the electronic devices described in this embodiment, so that a long-life electronic device can be obtained.

[0218] Another electronic device incorporating the light-emitting device is a foldable portable information terminal, which is located in Fig. 5A to Fig. 5C is shown. Fig. 5A represents a portable information terminal 9310, which is unfolded. Fig. Figure 5B depicts the portable information terminal 9310 during unfolding or folding. Fig. Figure 5C depicts the 9310 portable information terminal in its folded state. The 9310 portable information terminal is highly portable when folded. When unfolded, the 9310 portable information terminal offers excellent searchability due to its large, seamless display area.

[0219] A display section 9311 is supported by three housings 9315 connected to each other by hinges 9313. It should be noted that the display section 9311 can be a touchscreen (input / output device) that includes a touch sensor (input device). The shape of the portable information terminal 9310 can be reversibly changed from an open state to a folded state by bending the display section 9311 at a connection point between two housings 9315 using the hinges 9313. The light-emitting device of an embodiment of the present invention can be used for the display section 9311. Furthermore, a long-life electronic device can be obtained. A display area 9312 in the display section 9311 is a display area positioned on a side surface of the folded portable information terminal 9310.The display area 9312 can show information icons, shortcuts to frequently used applications or programs, and the like, and allows for easy confirmation of information as well as starting applications and the like.

[0220] Fig. 6A and Fig. 6B represents a vehicle that incorporates the light-emitting device. The light-emitting device may be installed in the vehicle, and in particular may be located in headlights 5101 (including rear headlights of the car), a wheel cover 5102, part of a door 5103 or the whole of a door 5103, or the like, on the outside of the vehicle. Fig. The light-emitting device may also be contained in a display section 5104, a steering wheel 5105, a gearshift lever 5106, a seat 5107, an interior rearview mirror 5108, or the like, inside the vehicle shown in Figure 6A. Fig. 6B depicted vehicle or contained in part of a glass window.

[0221] In the manner described above, electronic devices and vehicles can be obtained using the light-emitting device or the display device of an embodiment of the present invention. In this case, a long-life electronic device can be obtained. It should be noted that the light-emitting device or the display device for electronic devices and vehicles can be used in various fields, not limited to those described in this embodiment.

[0222] It should be noted that the structures described in this embodiment can be combined with any of the structures described in the other embodiments as required. (Version 6)

[0223] In this embodiment, the structure of a lighting device, which is manufactured using the light-emitting device of an embodiment of the present invention or the light-emitting element that is part of the light-emitting device, is described by means of Fig. 7A and Fig. 7B described.

[0224] Fig. 7A and Fig. Figure 7B shows examples of cross-sectional views of lighting devices. Fig. 7A represents a bottom-emission lighting device in which light is extracted from the side of the substrate, and Fig. 7B represents a top-emission lighting device in which light is extracted from the side of the sealing substrate.

[0225] A lighting device 4000, which is in Fig. Figure 7A shows a light-emitting element 4002 above a substrate 4001. The lighting device 4000 also includes a substrate 4003 with an unevenness on the outside of the substrate 4001. The light-emitting element 4002 includes a first electrode 4004, an EL layer 4005, and a second electrode 4006.

[0226] The first electrode 4004 is electrically connected to an electrode 4007, and the second electrode 4006 is electrically connected to an electrode 4008. An auxiliary conductor 4009, electrically connected to the first electrode 4004, can also be provided. It should be noted that an insulating layer 4010 is formed over the auxiliary conductor 4009.

[0227] The substrate 4001 and a sealing substrate 4011 are joined to each other by a sealing agent 4012. A desiccant 4013 is preferably provided between the sealing substrate 4011 and the light-emitting element 4002. The substrate 4003 has the following features: Fig. 7A shows an unevenness which can increase the extraction efficiency of the light emitted by the light-emitting element 4002.

[0228] A lighting device 4200, which is in Fig. Figure 7B shows a light-emitting element 4202 above a substrate 4201. The light-emitting element 4202 includes a first electrode 4204, an EL layer 4205 and a second electrode 4206.

[0229] The first electrode 4204 is electrically connected to an electrode 4207, and the second electrode 4206 is electrically connected to an electrode 4208. An auxiliary line 4209, electrically connected to the second electrode 4206, can be provided. An insulating layer 4210 can be provided under the auxiliary line 4209.

[0230] The substrate 4201 and a sealing substrate 4211 with unevenness are bonded to each other with a sealant 4212. A barrier film 4213 and a planarizing film 4214 can be provided between the sealing substrate 4211 and the light-emitting element 4202. The sealing substrate 4211 has the following properties: Fig. 7B depicted unevenness, which can increase the extraction efficiency of the light emitted by the light-emitting element 4202.

[0231] Examples of such lighting devices include ceiling lights for interior lighting. Examples of ceiling lights include directly mounted lights and recessed lights. Such lighting devices are manufactured using a combination of the light-emitting device and a housing or cover.

[0232] Another example: Such lighting devices can be used for floor lighting, illuminating a floor and thus improving floor safety. Floor lighting can be effectively used, for example, in a bedroom, on stairs, or in a hallway. In this case, the size or shape of the floor lighting can be adapted to the area or structure of a room. The floor lighting can be a stationary lighting device, manufactured using a combination of the light-emitting device and a support.

[0233] Such lighting devices can also be used for a leaf-shaped lighting fixture (leaf-shaped lighting). The leaf-shaped lighting, which is mounted on a wall, is space-saving and can therefore be used for a wide variety of purposes. Furthermore, the surface area of ​​the leaf-shaped lighting can be easily enlarged. The leaf-shaped lighting can also be used on a wall or housing with a curved surface.

[0234] In addition to the above examples, if the light-emitting device of an embodiment of the present invention, or the light-emitting element that is part of the light-emitting device, is used as part of a piece of furniture in a room, a lighting device that serves as that piece of furniture can be obtained.

[0235] As described above, various lighting devices incorporating the light-emitting device can be obtained. It should be noted that these lighting devices are also embodiments of the present invention.

[0236] It should be noted that the structures described in this embodiment can be used in combination with one of the structures described in the other embodiments, as required. [Example 1]<<Synthesebeispiel 1> >

[0237] This example describes a method for synthesizing 13-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h][1]benzofuro[2,3-h]quinoxaline (abbreviation: 13mDBtPBfdbq), i.e., the organic compound of an embodiment of the present invention, which in embodiment 1 is represented by the structural formula (100). The structure of 13mDBtPBfdbq is shown below. <Schritt 1: Synthese von 1,4-Dihydrophenanthro[9,10-b]pyrazin-2,3-dion>

[0238] 5.97 g of phenanthrene-9,10-diamine hydrochloride, 16.51 g of sodium bicarbonate, and 230 mL of diethyl oxalate were placed in a three-necked flask equipped with a reflux tube, and the air in the flask was replaced with nitrogen. The mixture was then stirred at 130 °C for 23 hours to initiate a reaction. After a predetermined time, 1 L of water was added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The resulting mixture was suction-filtered and washed with ethanol, giving 3.91 g of a target pyrazine derivative (ochre-colored powder) in a 61% yield. A synthesis scheme for step 1 is shown below in (a-1). <Schritt 2: Synthese von 2,3-Dichlordibenzo[f,h]chinoxalin>

[0239] Next, 3.91 g of 1,4-dihydrophenanthro[9,10-b]pyrazine-2,3-dione, obtained in step 1, and 60 mL of anhydrous DMF were placed in a three-necked flask equipped with a reflux tube, and the air in the flask was replaced with nitrogen. After the flask had been cooled with ice, 5.4 mL of phosphoryl chloride were added, and the mixture was stirred at 100 °C for 7.5 hours. After a predetermined time, the resulting mixture was added to 130 mL of a 1 M aqueous solution of sodium hydroxide, and suction filtration was performed. The resulting solid was washed with water and ethanol and dissolved in toluene, and the mixture was filtered through Celite. The filtrate obtained was concentrated to give 1.00 g of a target quinoxaline derivative (yellowish-white powder) in a 22% yield. A synthesis scheme for step 2 is shown below in (a-2). <Schritt 3: Synthese von 2-Chlor-3-(5-chlor-2-methoxyphenyl)chinoxalin>

[0240] Next, 1.85 g of 2,3-dichlorodibenzo[f,h]quinoxaline, obtained in step 2, 1.16 g of 5-chloro-2-methoxyphenylboronic acid, 0.66 g of sodium carbonate, 27 mL of ethylene glycol dimethyl ether (abbreviation: DME), and 27 mL of water were placed in a three-necked flask equipped with a reflux tube, and the air in the flask was replaced with nitrogen. The mixture in the flask was degassed by stirring under reduced pressure, and then 0.48 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added. Stirring was carried out for 20.5 hours at 100 °C to initiate a reaction. After a predetermined time, water was added to the reaction solution, the solid obtained by suction filtration was dissolved in dichloromethane and filtered, and the filtrate was concentrated.The obtained solid was purified by silica gel column chromatography using a mobile phase in which the ratio of toluene to hexane was 1:2, yielding 1.86 g of a target quinoxaline derivative (white powder) in a yield of 74%. A synthesis scheme for step 3 is shown below in (a-3). <Schritt 4: Synthese von 2-Chlor-3-(5-chlor-2-hydroxyphenyl)chinoxalin>

[0241] Next, 2.56 g of 2-chloro-3-(5-chloro-2-methoxyphenyl)quinoxaline, obtained in step 3, and 70 ml of anhydrous dichloromethane were placed in a three-necked flask, and the air in the flask was replaced with nitrogen. After the flask had been cooled to -20 °C, 13 ml of boron tribromide (1 M dichloromethane solution) were added dropwise, and the resulting mixture was stirred at room temperature for 16 hours. After a predetermined time, water was added, and an extraction was carried out with dichloromethane. The solid obtained by the extraction was purified by silica gel column chromatography using dichloromethane as the mobile phase, giving 2.12 g of a target quinoxaline derivative (yellow powder) in 84% yield. A synthesis scheme of step 4 is shown below in (a-4). <Schritt 5: Synthese von 13-Chlordibenzo[f,h][1]benzofuro[2,3-b]chinoxalin>

[0242] Subsequently, 2.12 g of 2-chloro-3-(5-chloro-2-hydroxyphenyl)quinoxaline, obtained in step 4, and 27 ml of anhydrous N-methyl-2-pyrrolidone (abbreviated NMP) were placed in a three-necked flask equipped with a reflux tube, and the air in the flask was replaced with nitrogen. Then, 1.51 g of potassium carbonate was added to the mixture, and the resulting mixture was stirred at 120 °C for 8 hours. After a predetermined time, water was added, and the resulting mixture was suction-filtered. The resulting solid was washed with ethanol, giving 1.56 g of a target quinoxaline derivative (pale yellow powder) in 84% yield. The synthesis scheme of step 5 is shown below in (a-5). <Schritt 6: Synthese von 13-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h][1]benzofuro[2,3-b]chinoxalin (Abkürzung: 13mDBtPBfdbq)>

[0243] Subsequently, 0.78 g of 13-chlorodibenzo[f,h][1]benzofuro[2,3-b]quinoxaline, obtained in step 5, 1.10 g of (dibenzothiophen-4-yl)phenyl-3-boronic acid, 1.26 g of cesium fluoride, and 44 ml of mesitylene were placed in a three-necked flask equipped with a reflux tube, and the air in the flask was replaced with nitrogen. This mixture was degassed by stirring under reduced pressure, 0.075 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) and 0.059 g of 2'-(dicyclohexylphosphino)acetophenone ethyleneketal were added, and the resulting mixture was stirred for 17.5 hours at 120 °C. After a predetermined time, the resulting mixture, to which ethanol had been added, was suction filtered and washed with water and ethanol.The recovered solid was dissolved in toluene, and the mixture was filtered through a filter aid in which celite, aluminum oxide, and celite were arranged in that order. The filtrate was concentrated, dried, and then recrystallized from toluene to obtain 0.71 g of a target compound (yellowish-white powder) in a 56% yield. 0.70 g of the obtained yellowish-white powder were purified by train sublimation. In the sublimation purification, the solid was heated at 330 °C under a pressure of 2.7 Pa with an argon gas flow rate of 10.5 ml / min. After sublimation purification, 0.5 g of a yellowish-white target solid was obtained in an 80% yield. A synthesis scheme for step 6 is shown below in (a-6).

[0244] Analysis results by nuclear magnetic resonance spectroscopy ( 1 The 1H NMR measurements of the yellowish-white solid obtained in step 6 are shown below. 1 H-NMR spectrum is in Fig. Figure 8 shows. These results reveal that 13mDBtPBfdbq, i.e. the organic compound represented by structural formula (100) of an embodiment of the present invention, was obtained in this example.

[0245] 1 H NMR. δ (CDCl3): 7.49-7.51 (m, 2H), 7.63-7.64 (m, 2H), 7.71 (t, 1H), 7.80-7.89 (m, 8H), 8.06 (d, 1H), 8.16 (s, 1H), 8.22-8.25 (m, 2H), 8.70-8.74 (m, 3H), 9.36 (d, 1H), 9.49-9.51 (m, 1H).

[0246] Subsequently, the UV / VIS absorption spectra (hereinafter referred to simply as "absorption spectra") and emission spectra of 13mDBtPBfdbq were measured in a toluene solution and a solid thin film of 13mDBtPBfdbq.

[0247] The absorption spectrum of 13mDBtPBfdbq in toluene solution was measured using a UV-VIS spectrophotometer (V550 type, manufactured by JASCO Corporation). The emission spectrum of 13mDBtPBfdbq in toluene solution was measured using a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK). Fig. Figure 9A shows the obtained absorption and emission spectra of 13mDBtPBfdbq in the toluene solution. The horizontal axis represents the wavelength, and the vertical axes represent the absorption and emission intensities.

[0248] Fig. Figure 9A shows that 13mDBtPBfdbq in the toluene solution has absorption peaks at about 281 nm and 397 nm and an emission wavelength peak at about 405 nm (the excitation wavelength: 372 nm).

[0249] The solid thin film of 13mDBtPBfdbq was formed on a quartz substrate by vacuum evaporation, and its absorption spectrum was measured using a UV-VIS spectrophotometer (U-4100, manufactured by Hitachi High-Technologies Corporation). The emission spectrum of the same 13mDBtPBfdbq thin film was measured using a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK). The obtained absorption and emission spectra of the 13mDBtPBfdbq solid thin film are presented in Fig. Figure 9B shows the horizontal axis representing the wavelength, and the vertical axes representing the absorption intensity and the emission intensity.

[0250] Fig. Figure 9B shows that the solid thin film of 13mDBtPBfdbq exhibits absorption peaks at approximately 383 nm and 403 nm, as well as an emission wavelength peak at approximately 511 nm (the excitation wavelength: 380 nm).

[0251] Differential calorimetry was also performed on 13mDBtPBfdbq. A differential calorimeter (Pyris 1, PerkinElmer Japan Co., Ltd.) was used for the calorimetry. One cycle of the calorimetry was as follows: The temperature was increased from -10 °C to 350 °C at a rate of 40 °C / min, held at 350 °C for one minute, and then decreased from 350 °C to -10 °C at a rate of 100 °C / min. In this example, the measurement was performed for up to three cycles. From the result of the increasing temperature in the second cycle, it was determined that the glass transition temperature (Tg) g ) 141 °C. This suggests that 13mDBtPBfdbq, which was synthesized in this example, has very high heat resistance. [Example 2]

[0252] This example describes the element structures, manufacturing processes, and properties of a light-emitting element 1 (a light-emitting element of an embodiment of the present invention) and a light-emitting reference element 2. Light-emitting element 1 uses 13-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13mDBtPBfdbq) (structural formula (100)) for a light-emitting layer, which has been described in Example 1. Light-emitting reference element 2 uses 2-[3-(3'-Dibenzothiophen-4-yl)biphenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) (structural formula (200)) for a light-emitting layer. It should be noted that Fig. Figure 10 presents an elemental structure of the light-emitting elements used in this example, and Table 1 shows specific structures. The chemical formulas of the materials used in this example are shown below. [Table 1] first electrode Hole injection layer Hole transport layer light-emitting layer electron transport layer Electron injection layer second electrode 901 911 912 913 914 915 903 Light-emitting element 1 ITSO (70 nm) DBT3P-II:MoOx(2:1, 70 nm) PCBBi1BP(20 nm) * mPCCzPTzn-02(30 nm) NBphen(15 nm) LiF(1 nm) Al(200 nm) Light-emitting reference element 2 ITSO (70 nm) DBT3P-II:MoOx(2:1, 70 nm) PCBBi1BP(20 nm) ** mPCCzPTzn-02(30 nm) NBphen(15 nm) LiF(1 nm) Al(200 nm) *13mDBtPBfdbq : PCBBIF : [Ir(dmpqn)2(acac)] (0.75:0.25:0.1, 40 nm) **** 2mDBTBPDBq-II : PCBBiF : [Ir(dmpqn)2(acac)] (0.75:0.25:0.1, 40 nm) <Herstellung der Licht emittierenden Elemente>

[0253] Each of the light-emitting elements described in this example has, as shown in Fig. Figure 10 shows 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 arranged in this order over a first electrode 901 formed over a substrate 900, and a second electrode 903 is arranged over the electron injection layer 915.

[0254] First, the first electrode 901 was formed over the substrate 900. The electrode area was set to 4 mm². 2 (2 mm × 2 mm). A glass substrate was used as substrate 900. The first electrode 901 was formed by a sputtering process using indium tin oxide containing silicon oxide (ITSO) with a thickness of 70 nm.

[0255] As a pretreatment, the substrate surface was washed with water, baked for one hour at 200 °C, and then treated with UV ozone for 370 seconds. Afterwards, the substrate was transferred to a vacuum evaporation device where the pressure was set to approximately 10 -4 After the Pa was reduced, vacuum baking was carried out for 30 minutes at 170 °C in a heating chamber of the vacuum evaporation device, and then the substrate was cooled for approximately 30 minutes.

[0256] Next, the hole injection layer 911 was formed over the first electrode 901. After the pressure in the vacuum evaporation device was increased to 1 × 10 -4 After Pa had been reduced, the hole injection layer 911 was formed by co-evaporation of 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum oxide to a thickness of 70 nm to have a mass ratio of 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) to molybdenum oxide of 2:1.

[0257] Subsequently, the hole transport layer 912 was formed over the hole injection layer 911. The hole transport layer 912 was formed by evaporation of 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP) to a thickness of 20 nm.

[0258] Next, the light-emitting layer 913 was formed above the hole transport layer 912.

[0259] The light-emitting layer 913 in the light-emitting element 1 was created by co-evaporation of 13mDBtPBfdbq, i.e., the organic compound of an embodiment of the present invention, as host material, PCBBiF as auxiliary material, and Bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmpqn)2(acac)]) as guest material (phosphorescent material) in a thickness of 40 nm to have a weight ratio of 13mDBtPBfdbq to PCBBiF and [Ir(dmpqn)2(acac)] of 0.75:0.25:0.1.

[0260] The light-emitting layer 913 in the light-emitting reference element 2 was formed by co-evaporation of 2mDBTBPDBq-II as host material, PCBBiF as auxiliary material and [Ir(dmpqn)2(acac)] as guest material (phosphorescent material) in a thickness of 40 nm to have a weight ratio of 2mDBTBPDBq-II to PCBBiF and [Ir(dmpqn)2(acac)] of 0.75:0.25:0.1.

[0261] Next, the electron transport layer 914 was formed over the light-emitting layer 913. The electron transport layer 914 was formed as follows: 9-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02) and 2,9-Bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen) were successively deposited by evaporation to thicknesses of 30 nm and 15 nm, respectively.

[0262] Subsequently, the electron injection layer 915 was formed over the electron transport layer 914. The electron injection layer 915 was formed by evaporating lithium fluoride (LiF) to a thickness of 1 nm.

[0263] The second electrode 903 was then formed above the electron injection layer 915. The second electrode 903 was formed by evaporating aluminum to a thickness of 200 nm. In this example, the second electrode 903 serves as the cathode.

[0264] By the preceding steps, the light-emitting elements, each comprising an EL layer between a pair of electrodes, were formed on the substrate 900. The hole injection layer 911, the hole transport layer 912, the light-emitting layer 913, the electron transport layer 914, and the electron injection layer 915, which have been described above, are functional layers that form the EL layer of an embodiment of the present invention. Furthermore, in all evaporation steps of the preceding manufacturing process, evaporation was carried out by a resistance heating process.

[0265] Each of the light-emitting elements, fabricated as described above, was sealed using a further substrate (not shown) such that the substrate (not shown) was fixed to substrate 900 with a UV-curing sealant in a glove box containing a nitrogen atmosphere, and the substrates were joined to one another by the sealant adhering to the periphery of the light-emitting element formed above substrate 900. During sealing, the sealant was cured with 365 nm UV light at 6 J / cm². 2 It was irradiated to solidify, and the sealant was heated at 80°C for one hour to stabilize it. <<Betriebseigenschaften der Licht emittierenden Elemente> >

[0266] The operating characteristics of the manufactured light-emitting elements were measured. It should be noted that the measurement was carried out at room temperature (in an atmosphere maintained at 25 °C). Fig. 11 to Fig. Figure 14 shows the measurement results.

[0267] Table 2 lists the initial values ​​of the main properties of light-emitting elements at approximately 1000 cd / m². 2 on. [Table 2] Voltage (V) Current (mA) Current density (mA / cm³) 2 ) Chromaticity(x,y) Luminance (cd / m²) 2 ) Power efficiency (cd / A) Energy efficiency (Im / W) external quantum yield (%) Light-emitting element 1 3,2 0,25 6,3 (0,68, 0,32) 1000 16 15 19 Light-emitting reference element 2 3,4 0,21 5,3 (0,68, 0,32) 910 17 16 19

[0268] The preceding results show that the light-emitting element 1 produced in this example exhibits excellent current-voltage characteristics compared to the light-emitting reference element 2. This is presumably due to the fact that 13mDBtPBfdbq, an embodiment of the present invention used in the light-emitting layer of the light-emitting element 1, has a low LUMO level due to a structure in which an oxygen-containing five-membered ring is condensed. According to the cyclic voltammetry (CV) measurement results of the reduction potentials, the LUMO level of 2mDBTBPDBq-II was -2.94 eV, while the LUMO level of 13mDBtPBfdbq was -3.17 eV.

[0269] Fig. Figure 15 shows emission spectra in the case where a current with a density of 2.5 mA / cm² is applied to the light-emitting element 1 and the light-emitting reference element 2. 2 was supplied. As in Fig. As shown in Figure 15, the emission spectrum of the light-emitting element 1 and that of the light-emitting reference element 2 each exhibit a peak at about 628 nm, which is probably due to light emission from the metal-organic complex [Ir(dmpqn)2(acac)] contained in the light-emitting layer 913.

[0270] Next, reliability tests were performed on the light-emitting element 1 and the light-emitting comparison element 2. Fig. Figure 16 shows the results of the reliability tests. Fig. Figure 16 shows the normalized luminance (%) at an initial luminance of 100%, and the horizontal axis represents the operating time (h) of the elements. During the reliability tests, the light-emitting elements were operated at a current density of 75 mA / cm². 2 targeted.

[0271] The results of the reliability tests show that light-emitting element 1 exhibits higher reliability than light-emitting reference element 2. This is likely due to the use of the organic compound 13mDBtPBfdbq (structural formula (100)) of an embodiment of the present invention in the light-emitting layer of light-emitting element 1. Since 13mDBtPBfdbq has a structure in which, as described for embodiment 1, an oxygen-containing five-membered ring is condensed to the 2- and 3-positions of a dibenzoquinoxaline framework, unlike 2mDBTBPDBq-II (structural formula: 200), steric repulsion between a substituted phenylene group at the 2-position of the dibenzoquinoxaline framework and hydrogen at the 3-position does not cause the substituted phenylene group to rotate, leading to improvements in robustness and stability. of molecules.The excellent current-voltage characteristics of light-emitting element 1 compared to light-emitting reference element 2, shown in Table 2, indicate that light-emitting element 1 has a narrow charge carrier recombination region in the light-emitting layer and an element structure that readily causes local degradation. The reason why light-emitting element 1, as shown in . Fig. As shown in Figure 16, the high reliability of the organic compound in an embodiment of the present invention is due to its low steric hindrance and its high robustness and stability. This means that the organic compound in an embodiment of the present invention is a material that overcomes the contradiction between low drive voltage and high reliability, a problem frequently encountered in light-emitting elements.

[0272] Moreover, the organic compound 13mDBtPBfdbq of an embodiment of the present invention not only possesses the aforementioned molecular structure to increase reliability, but also a structure with a condensed oxygen-containing five-membered ring to minimize a decrease in the T1 level caused by a condensed polycyclic molecular structure. In particular, the T1 levels of 2mDBTBPDBq-II and 13mDBtPBfdbq were estimated assuming that they correspond to peaks on the short-wavelength side of the phosphorescence spectra observed at a liquid nitrogen temperature (77 K); the T1 level of 2mDBTBPDBq-II was 515 nm, and the T1 level of 13mDBtPBfdbq was 538 nm. Therefore, the T1 level shifted only approximately 20 nm towards the long wavelength.Thus, the use of the organic compound 13mDBtPBfdbq (structural formula (100)) of an embodiment of the present invention in the EL layer of a light-emitting element is effective in maintaining the T1 level to a certain degree and increasing the reliability of the light-emitting element. [Example 3]<<Synthesebeispiel 2> >

[0273] This example describes a method for synthesizing 13-[3-(Dibenzofuran-4-yl)phenyl]dibenzo[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13mDBfPBfdbq), i.e., the organic compound of an embodiment of the present invention, which in embodiment 1 is represented by the structural formula (101). The structure of 13mDBfPBfdbq is shown below. <Synthese von 13mDBfPBfdbq>

[0274] 13mDBfPBfdbq, which is described in this example, is synthesized by the procedure shown in the following synthesis scheme (b-1), as in the synthesis procedure of 13mDBtPBfdbq described in Example 1.

[0275] In this way, the organic compound 13mDBfPBfdbq of an embodiment of the present invention can be obtained. [Example 4]<<Synthesebeispiel 3> >

[0276] This example describes a method for synthesizing 13-[3-(9H-carbazol-9-yl)phenyl]dibenzo[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13mCzPBfdbq), i.e., the organic compound of an embodiment of the present invention, which in embodiment 1 is represented by the structural formula (102). The structure of 13mCzPBfdbq is shown below. <Synthese von 13mCzPBfdbq>

[0277] 13mCzPBfdbq in this example is synthesized by the procedure shown in the following synthesis scheme (c-1), as in the synthesis procedure of 13mDBtPBfdbq described in Example 1.

[0278] In this way, the organic compound 13mCzPBfdbq of an embodiment of the present invention can be obtained. [Example 5]<<Synthesebeispiel 4> >

[0279] This example describes a method for synthesizing 13-[3-(Triphenylen-2-yl)phenyl]dibenzo[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13mTpPBfdbq), i.e., the organic compound of an embodiment of the present invention, which in embodiment 1 is represented by the structural formula (110). The structure of 13mTpPBfdbq is shown below. <Synthese von 13mTpPBfdbq>

[0280] 13mTpPBfdbq, which is described in this example, is synthesized by the procedure shown in the following synthesis scheme (d-1), as in the synthesis procedure of 13mDBtPBfdbq described in Example 1.

[0281] In this way, the organic compound 13mTpPBfdbq of an embodiment of the present invention can be obtained. [Example 6]<<Synthesebeispiel 5> >

[0282] This example describes a method for synthesizing 13-[3-(9'-Phenyl-3,3'-bi-9H-carbazol-9-yl)phenyl]dibenzo[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13mPCCzPBfdbq), i.e., the organic compound of an embodiment of the present invention, which in embodiment 1 is represented by the structural formula (123). The structure of 13mPCCzPBfdbq is shown below. <Synthese von 13mPCCzPBfdbq>

[0283] 13mPCCzPBfdbq, which is described in this example, is synthesized by the procedure shown in the following synthesis scheme (e-1), as in the synthesis procedure of 13mDBtPBfdbq described in Example 1.

[0284] In this way, the organic compound 13mPCCzPBfdbq of an embodiment of the present invention can be obtained. [Example 7]<<Synthesebeispiel 6> >

[0285] This example describes a method for synthesizing 13-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)dibenzo[f,h][1]benzofuro[2,3-h]quinoxaline (abbreviation: 13PCCzBfdbq), i.e., the organic compound of an embodiment of the present invention, which in embodiment 1 is represented by the structural formula (125). The structure of 13PCCzBfdbq is shown below. <Synthese von 13PCCzBfdbq>

[0286] Next, 0.78 g of 13-chlorodibenzo[f,h][1]benzofuro[2,3-b]quinoxaline, obtained in step 5 of Example 1, 0.90 g of 9'-phenyl-3,3'-bi-9H-carbazole, and 22 ml of mesitylene were placed in a three-necked flask equipped with a reflux tube, and the air in the flask was replaced with nitrogen. The mixture in the flask was degassed by stirring under reduced pressure, and then 0.42 g of sodium tert-butoxide, 0.013 g of bis(dibenzylideneacetone)palladium(0) (abbreviation: Pd(dba)2), and 0.018 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) were added. The resulting mixture was stirred for 13 hours at 150 °C.

[0287] After a predetermined time, the resulting mixture, to which ethanol had been added, was subjected to suction filtration and washed with water and ethanol. Purification was then carried out by silica gel column chromatography using toluene as the mobile phase, yielding 0.56 g of a target substance (yellow solid) in a 35% yield. The synthesis scheme of the above synthesis procedure described in this example is shown below in (f-1).

[0288] Analysis results through nuclear magnetic resonance ( 1 H-NMR-) spectroscopy of the yellow solid obtained above is shown below. Fig. 17 is the 1 H-NMR spectrum. These results reveal that 13PCCzBfdbq, i.e. the organic compound represented by structural formula (125) of an embodiment of the present invention, was obtained in this example.

[0289] 1 H-NMR. δ (CDCl3): 7,33 (t, 1H), 7,39 (t, 1H), 7,45-7,56 (m, 6H), 7,62-7,69 (m, 5H), 7,79-7,90 (m, 6H), 7,95 (d, 1H), 8,06 (d, 1H), 8,27 (d, 1H), 8,32 (d, 1H), 8,56 (d, 2H), 8,70-8,76 (m, 3H), 9,36 (d, 1H), 9,44 (d, 1H).< / substrat> < / elektroneninjektionsschicht> < / elektronentransportschicht>

Claims

[1] Compound represented by formula (G1): where QO represents where at least one of R 1 to R 12 a first group which is a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms, and where each of the other from R 1 to R 12 independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group or a group with 1 to 50 carbon atoms. [2] Compound according to claim 1, where the first group comprises a structure selected from the structures represented by formulas (A-1) to (A-21), where each of the other from R 1 to R 12independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms, where Q' represents O or S, and where each of R 13 to R 24 independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. [3] Compound according to claim 1, wherein the first group represents one of the formulas (A-1) to (A-21), where each of the other from R 1 to R 12 independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms, where Q' represents O or S, and where each of R 13 to R 24 independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. [4] Compound according to claim 2, wherein the structure selected from the structures represented by formulas (A-1) to (A-21) is linked to the dibenzobenzofurochinoxaline or dibenzobenzothienochinoxaline framework via a substituted or unsubstituted arylene group having 6 to 24 carbon atoms in a ring or a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms in a ring. [5] Compound represented by formula (G1): where QO represents where R 3a first group which has a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms, and where each of R 1 , R 2 and R 4 to R 12 independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group or a group with 1 to 50 carbon atoms. [6] Compound according to claim 1 or 5, wherein the first group has a hole transport property which is higher than an electron transport property. [7] Compound according to claim 1 or 5, wherein the first group comprises a fluorene scaffold, a phenanthrene scaffold, a triphenylene scaffold, a naphthalene scaffold, a dibenzothiophene scaffold, a dibenzofuran scaffold or a carbazole scaffold. [8] Compound according to claim 5, where the first group comprises a structure selected from the structures represented by formulas (A-1) to (A-21), where each of R 1 , R 2 and R 4 to R 12 independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms, where Q' represents O or S, and where each of R 13 to R 24 independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. [9] Compound according to claim 5, wherein the first group is represented by one of the formulas (A-1) to (A-21), where each of R 1 , R2 and R 4 to R 12 independently represents hydrogen, a halogen group, a hydroxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms, where Q' represents O or S, and where each of R 13 to R 24 independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 5 to 7 carbon atoms in a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. [10] Compound according to claim 8, wherein the structure selected from the structures represented by formulas (A-1) to (A-21) is linked to the dibenzobenzofurochinoxaline or dibenzobenzothienochinoxaline framework via a substituted or unsubstituted arylene group having 6 to 24 carbon atoms in a ring or a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms in a ring. [11] Compound according to claim 1 or 5, wherein the group comprising 1 to 50 carbon atoms is an alkyloxy group, an aryloxy group, an amino group to which an alkyl group is bonded, an amino group to which an aryl group is bonded, a cyano group, a carboxyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a silyl group to which an alkyl group is bonded, a silyl group to which an aryl group is bonded, an alkyl group, a cycloalkyl group, a heteroaryl group or an aryl group. [12] Compound according to claim 5, wherein the compound is represented by formula (100) or formula (125): [13] Light-emitting device comprising: a light-emitting layer between a pair of electrodes, wherein the light-emitting layer comprises the compound according to claim 1 or 5. [14] Light-emitting device according to claim 13, wherein the light-emitting layer further comprises a metal-organic complex. [15] Light-emitting device according to claim 14, wherein the metal-organic complex is an iridium complex with a phenylquinoline skeleton. [16] Electronic device comprising: the light-emitting device according to claim 13; and at least one consisting of a microphone, a camera, a control button, an external connection section and a speaker. [17] Lighting device comprising: the light-emitting device according to claim 13; and at least one of a housing, a cover and a support.

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