Light-emitting device

Abstract

To provide a novel organic compound, provide a novel organic compound having hole transport properties, provide a novel hole transport material, provide a novel light-emitting element, provide a light-emitting element with a long service life, and provide a light-emitting element having good luminous efficiency.SOLUTION: Provided is an organic compound having a benzo [b] naphtho [2,1-d] furanyl group or a benzo [b] naphtho [2,3-d] furanyl group and a diarylamine structure. Also provided is a light-emitting element using said organic compound.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] An embodiment of the present invention relates to a light-emitting element, a display module, a lighting module, a display device, a light-emitting device, an electronic device, and a lighting device. Note that an embodiment of the present invention is not limited to the above technical field. A technical field of an embodiment of the present invention disclosed in the present specification and the like relates to an object, a method, or a manufacturing method. Alternatively, an embodiment of the present invention relates to a process, a machine, a manufacture, or a composition of matter. Therefore, examples of technical fields of an embodiment of the present invention disclosed in the present specification more specifically include a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, a lighting device, a power storage device, a storage device, an imaging device, a driving method thereof, or a manufacturing method thereof. [Background technology]

[0002] Light-emitting elements (organic EL elements) that utilize electroluminescence (EL) using organic compounds are becoming more and more practical. The basic structure of these light-emitting elements is a pair of electrodes sandwiching an organic compound layer (EL layer) containing a light-emitting material between them. By applying a voltage to this element, carriers are injected, and the recombination energy of the carriers is utilized to emit light from the light-emitting material.

[0003] Since such light-emitting elements are self-luminous, when used as pixels in a display, they have advantages such as higher visibility than liquid crystals and no need for backlighting, making them suitable as flat panel display elements. Another major advantage of displays using such light-emitting elements is that they can be manufactured to be thin and lightweight. Another characteristic is that they have an extremely fast response speed.

[0004] In addition, these light-emitting devices can emit light in a planar manner because the light-emitting layer can be formed continuously in two dimensions. This is a feature that is difficult to obtain with point light sources such as incandescent light bulbs and LEDs, or linear light sources such as fluorescent lamps, making them highly useful as planar light sources for lighting and other applications.

[0005] Displays and lighting devices using such light-emitting elements are suitable for use in a variety of electronic devices, and research and development is currently underway to develop light-emitting elements with better efficiency and life span.

[0006] In such a light-emitting element, a hole injection layer may be formed to facilitate the injection of holes into the EL layer, which is an organic compound. One of the materials for the hole injection layer is an organic compound having an acceptor property. The organic compound having an acceptor property is suitable for mass production because it can be easily formed into a film by vapor deposition, and is widely used. However, if the LUMO level of the organic compound having an acceptor property and the HOMO level of the organic compound constituting the hole transport layer are far apart, it is difficult to inject holes into the EL layer. Therefore, it is necessary to bring the LUMO level of the organic compound having an acceptor property closer to the HOMO level of the organic compound constituting the hole transport layer. However, if the HOMO level of the organic compound constituting the hole transport layer is made shallow, the difference between the HOMO level of the light-emitting layer and the HOMO level of the hole transport layer becomes large, and there is a problem that even if holes can be injected from the electrode into the EL layer, it becomes difficult to inject holes from the hole transport layer into the host material of the light-emitting layer.

[0007] Patent Document 1 discloses a configuration in which a hole-transporting material having a HOMO level between the HOMO level of the first hole-injection layer and the HOMO level of the host material is provided between a first hole-transporting layer in contact with a hole-injection layer and a light-emitting layer.

[0008] Although the characteristics of light-emitting devices have improved remarkably, they are still insufficient to meet high demands for efficiency, durability, and all other characteristics. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] International Publication No. 2011 / 065136 Brochure Summary of the Invention [Problem to be solved by the invention]

[0010] In view of the above, an object of one embodiment of the present invention is to provide a novel organic compound. Alternatively, an object of one embodiment of the present invention is to provide a novel organic compound having a hole-transport property. Alternatively, an object of one embodiment of the present invention is to provide a novel hole-transport material. Alternatively, an object of one embodiment of the present invention is to provide a novel light-emitting element. Alternatively, an object of one embodiment of the present invention is to provide a light-emitting element with a long lifetime. Alternatively, an object of one embodiment of the present invention is to provide a light-emitting element with high emission efficiency. Alternatively, an object of one embodiment of the present invention is to provide a light-emitting element with a low driving voltage.

[0011] Another object of another embodiment of the present invention is to provide a light-emitting device, an electronic device, and a display device with high reliability, or to provide a light-emitting device, an electronic device, and a display device with low power consumption.

[0012] It is sufficient for the present invention to solve any one of the above problems. [Means for solving the problem]

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

[0014] [ka]

[0015] In the general formula (G1), R 1 ~R 10one of which is a group represented by the following general formula (g1), and the rest each independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0016] [ka]

[0017] In addition, in the general formula (g1), Ar 3 , Ar 4 Each of Ar independently represents any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the following general formula (g2) to (g4). 1 , Ar 2 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms; n and m each independently represent an integer of 0 to 2; 3 is a group represented by the following general formula (g4), n is 1 or 2, and Ar 4 is a group represented by the following general formula (g4), m is 1 or 2. When n is 2, two Ar 1 may be different or the same, and similarly, when m is 2, two Ar 2 may be different or the same. 3 , Ar 4 When is an aromatic hydrocarbon group having 6 to 10 carbon atoms and has a substituent, the substituent is one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and groups represented by the following general formulas (g2) to (g4):

[0018] In addition, n and m are 0, and Ar 3 and Ar 4is a phenyl group, and the 2- and 6-positions of the phenyl group are substituted with aromatic hydrocarbon groups. Also, n and m are each independently 1 or 2, and Ar 1 , Ar 2 In the case where the skeleton bonded to the nitrogen atom is a benzene ring, i.e., where the compound has an aniline skeleton, the structure in which the 2-position and 6-position of the aniline skeleton are substituted with aromatic hydrocarbon groups is excluded.

[0019] [ka]

[0020] In the general formula (g2), R 31 ~R 40 represents a single bond, and the nitrogen atom in the above general formula (g1), Ar 3 or Ar 4 The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0021] In addition, in the general formula (g3), R 41 ~R 50 represents a single bond, and the nitrogen atom in the above general formula (g1), Ar 3 or Ar 4 The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0022] In addition, in the general formula (g4), R 51 ~R 60 represents a single bond, and Ar 3 or Ar 4The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0023] In addition, another embodiment of the present invention is, in the above structure, the group represented by the general formula (g1) is R 1 , R 8 and R 10 It is an organic compound that bonds to one of the following:

[0024] Alternatively, another embodiment of the present invention is, in the above structure, the group represented by the general formula (g1) is R 10 It is an organic compound that bonds to

[0025] Another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[0026] [ka]

[0027] In the general formula (G2), R 11 ~R 20 one of which is a group represented by the following general formula (g1), and the rest each independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0028] [ka]

[0029] In the general formula (g1), Ar 3 , Ar 4each independently represents any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the following general formula (g2) to the following general formula (g4). 1 , Ar 2 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms; n and m each independently represent an integer of 0 to 2; 3 is a group represented by the following general formula (g4), n is 1 or 2, and Ar 4 is a group represented by the following general formula (g4), m is 1 or 2. When n is 2, two Ar 1 may be different or the same, and similarly, when m is 2, two Ar 2 may be different or the same. 3 , Ar 4 When is an aromatic hydrocarbon group having 6 to 10 carbon atoms and has a substituent, the substituent is one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and groups represented by the following general formulas (g2) to (g4):

[0030] In addition, n and m are 0, and Ar 3 and Ar 4 is a phenyl group, and the 2- and 6-positions of the phenyl group are substituted with aromatic hydrocarbon groups. Also, n and m are each independently 1 or 2, and Ar 1 , Ar 2 In the case where the skeleton bonded to the nitrogen atom is a benzene ring, i.e., where the compound has an aniline skeleton, the structure in which the 2-position and 6-position of the aniline skeleton are substituted with aromatic hydrocarbon groups is excluded.

[0031] [ka]

[0032] In the general formula (g2), R31 ~R 40 represents a single bond, and the nitrogen atom in the above general formula (g1), Ar 3 or Ar 4 The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0033] In addition, in the general formula (g3), R 41 ~R 50 represents a single bond, and the nitrogen atom in the above general formula (g1), Ar 3 or Ar 4 The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0034] In addition, in the general formula (g4), R 51 ~R 60 represents a single bond, and Ar 3 or Ar 4 The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0035] In addition, another embodiment of the present invention is, in the above structure, the group represented by the general formula (g1) is R 18 or R 20 It is an organic compound that bonds to

[0036] In addition, another embodiment of the present invention is a compound represented by the general formula (g1) in the above-mentioned structure, wherein the group represented by the general formula (G2) is R 20 It is an organic compound that bonds to

[0037] In addition, another aspect of the present invention is the above-mentioned structure, 1 and the Ar 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, 3 and Ar 4 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0038] In addition, another aspect of the present invention is the above-mentioned structure, 3 and the Ar 4 are each independently one of a substituted or unsubstituted phenyl group and a substituted or unsubstituted naphthyl group.

[0039] In addition, another aspect of the present invention is the above-mentioned structure, 1 and the Ar 2 are each independently a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0040] Alternatively, in another aspect of the present invention, in the above-mentioned configuration, the Ar 3 and the Ar 4 is an organic compound in which the phenyl group is

[0041] Alternatively, in another aspect of the present invention, in the above-mentioned configuration, the Ar 1 and the Ar 2 is an organic compound in which the phenylene group is

[0042] Another embodiment of the present invention is an organic compound having the above structure, in which n and m are each 2.

[0043] Another embodiment of the present invention is an organic compound having the above structure, in which both n and m are 1.

[0044] Another embodiment of the present invention is a light-emitting element that includes an anode, a cathode, and an EL layer. The EL layer is located between the anode and the cathode, and the EL layer contains the above-described organic compound.

[0045] Alternatively, another embodiment of the present invention is a light-emitting element including an anode, a cathode, and an EL layer, the EL layer being located between the anode and the cathode, the EL layer including a light-emitting layer, and the light-emitting layer including the above-described organic compound.

[0046] Another embodiment of the present invention is a light-emitting element having the above structure, in which the light-emitting layer further contains a light-emitting material.

[0047] Another embodiment of the present invention is a light-emitting element having the above structure, in which the light-emitting layer further contains a material having an electron-transporting property.

[0048] Alternatively, another embodiment of the present invention is a light-emitting element comprising an anode, a cathode, and an EL layer, the EL layer being located between the anode and the cathode, the EL layer having a light-emitting layer and a hole-transport layer, the light-emitting layer containing a light-emitting material, the hole-transport layer being located between the light-emitting layer and the anode, and the hole-transport layer containing the above-described organic compound.

[0049] Alternatively, another embodiment of the present invention is a light-emitting element having the above structure, in which the EL layer further includes a hole injection layer that is provided in contact with the anode and the hole transport layer, and the hole injection layer contains an organic compound having an acceptor property.

[0050] Another embodiment of the present invention is a light-emitting element having the above structure, in which the compound having acceptor properties is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene.

[0051] or a light-emitting element having the above structure, wherein the hole-transport layer has a first layer, a second layer, and a third layer, the first layer is located between the hole-injection layer and the second layer, the third layer is located between the second layer and the light-emitting layer, the first layer is in contact with the hole-injection layer, the third layer is in contact with the light-emitting layer, the first layer contains a first hole-transport material, the second layer contains the organic compound, the third layer contains a third hole-transport material, the light-emitting layer contains a host material and a light-emitting material, a HOMO level of the organic compound is deeper than a HOMO level of the first hole-transport material, a HOMO level of the host material is deeper than a HOMO level of the organic compound, and a difference between the HOMO level of the organic compound and the HOMO level of the third hole-transport material is 0.3 eV or less.

[0052] Another embodiment of the present invention is a light-emitting element having the above structure, in which the HOMO level of the first hole-transporting material is −5.4 eV or higher.

[0053] Another embodiment of the present invention is a light-emitting element having the above structure, in which a difference between a HOMO level of the first hole-transport material and a HOMO level of the organic compound is 0.3 eV or less.

[0054] Another embodiment of the present invention is a light-emitting element having the above structure, in which a difference between a HOMO level of the organic compound and a HOMO level of the third hole-transport material is 0.2 eV or less.

[0055] Another embodiment of the present invention is a light-emitting element having the above structure, in which a difference between a HOMO level of the first hole-transport material and a HOMO level of the organic compound is 0.2 eV or less.

[0056] Another embodiment of the present invention is a light-emitting element having the above structure, in which the HOMO level of the light-emitting material is higher than the HOMO level of the host material.

[0057] Another embodiment of the present invention is a light-emitting element having the above structure, in which the HOMO level of the third hole-transporting material is equal to or deeper than the HOMO level of the host material.

[0058] Another embodiment of the present invention is a light-emitting element having the above structure, in which the light-emitting material is a fluorescent substance.

[0059] Another embodiment of the present invention is a light-emitting element having the above structure, in which the light-emitting material emits blue fluorescent light.

[0060] Another embodiment of the present invention is a light-emitting element having the above structure, in which the light-emitting material is a condensed aromatic diamine compound. Note that an amino group in the aromatic diamine compound contains a carbazolyl group.

[0061] Another embodiment of the present invention is a light-emitting element having the above structure, in which the light-emitting material is a diaminopyrene compound. Note that an amino group in the diaminopyrene compound contains a carbazolyl group.

[0062] Another embodiment of the present invention is a light-emitting device having any of the above structures, further including a transistor or a substrate.

[0063] Another embodiment of the present invention is an electronic device including the above-described light-emitting device and a sensor, an operation button, a speaker, or a microphone.

[0064] Another embodiment of the present invention is a lighting device including a light-emitting device having any of the above structures and a housing.

[0065] In this specification, the light-emitting device includes an image display device using a light-emitting element. Also, a module in which a connector, such as an anisotropic conductive film or TCP (Tape Carrier Package) is attached to a light-emitting element, a module in which a printed wiring board is provided at the end of a TCP, or a module in which an IC (integrated circuit) is directly mounted on a light-emitting element by a COG (Chip On Glass) method may have a light-emitting device. Furthermore, lighting fixtures and the like may have a light-emitting device. Effect of the Invention

[0066] According to one embodiment of the present invention, a novel light-emitting element can be provided. Alternatively, a light-emitting element with a long lifetime can be provided. Alternatively, a light-emitting element with high emission efficiency can be provided. Alternatively, a light-emitting element with a low driving voltage can be provided.

[0067] According to another embodiment of the present invention, a light-emitting device, an electronic device, and a display device with high reliability can be provided. According to another embodiment of the present invention, a light-emitting device, an electronic device, and a display device with low power consumption can be provided.

[0068] Note that the description of these effects does not preclude the existence of other effects. Note that one embodiment of the present invention does not necessarily have all of these effects. Note that effects other than these will become apparent from the description in the specification, drawings, claims, etc., and it is possible to extract effects other than these from the description in the specification, drawings, claims, etc. [Brief description of the drawings]

[0069] [Figure 1] Schematic diagram of a light-emitting element. [Diagram 2] FIG. 1 is a conceptual diagram of an active matrix light-emitting device. [Diagram 3] FIG. 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 4] FIG. 1 is a conceptual diagram of an active matrix light-emitting device. [Diagram 5] FIG. 1 is a conceptual diagram of a passive matrix light-emitting device. [Figure 6] FIG. [Figure 7] FIG. [Figure 8] FIG. [Figure 9] FIG. [Figure 10] FIG. [Figure 11] 1 is a diagram illustrating an in-vehicle display device and a lighting device. [Figure 12] FIG. [Figure 13] FIG. [Figure 14] 1H NMR chart of 2-chlorobenzo[b]naphtho[2,3-d]furan. [Figure 15] 1H NMR chart of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviation: BBABnf(II)(2)). [Figure 16] Absorption and emission spectra of BBABnf(II)(2) in toluene solution. [Figure 17] Absorption and emission spectra of BBABnf(II)(2) in a thin film. [Figure 18] 1H NMR chart of 4-chlorobenzo[b]naphtho[2,3-d]furan. [Figure 19] 1H NMR chart of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)). [Figure 20] Absorption and emission spectra of BBABnf(II)(4) in toluene solution. [Figure 21] Absorption and emission spectra of BBABnf(II)(4) in a thin film. [Figure 22] Luminance-current density characteristics of Light-emitting element 1 and Light-emitting element 2. [Figure 23] Current efficiency-luminance characteristics of Light-emitting element 1 and Light-emitting element 2. [Figure 24] Luminance-voltage characteristics of light-emitting element 1 and light-emitting element 2. [Diagram 25] Current-voltage characteristics of light-emitting element 1 and light-emitting element 2. [Figure 26] 4 shows the external quantum efficiency-luminance characteristics of the light-emitting element 1 and the light-emitting element 2. [Figure 27] 4 shows the emission spectra of light-emitting element 1 and light-emitting element 2. [Figure 28] Normalized luminance-time change characteristics of light-emitting element 1 and light-emitting element 2. [Figure 29] luminance-current density characteristics of light-emitting element 3 and light-emitting element 4. [Diagram 30] Current efficiency-luminance characteristics of the light-emitting element 3 and the light-emitting element 4. [Diagram 31] luminance-voltage characteristics of light-emitting element 3 and light-emitting element 4. [Diagram 32] Current-voltage characteristics of light-emitting element 3 and light-emitting element 4. [Diagram 33] 4 shows external quantum efficiency-luminance characteristics of the light-emitting element 3 and the light-emitting element 4. [Diagram 34] 4 shows emission spectra of light-emitting element 3 and light-emitting element 4. [Diagram 35] Normalized luminance-time change characteristics of light-emitting element 3 and light-emitting element 4. [Diagram 36] luminance-current density characteristics of light-emitting element 5 and light-emitting element 6. [Figure 37] Current efficiency-luminance characteristics of the light-emitting element 5 and the light-emitting element 6. [Figure 38] luminance-voltage characteristics of light-emitting element 5 and light-emitting element 6. [Figure 39] Current-voltage characteristics of light-emitting element 5 and light-emitting element 6. [Diagram 40] 4 shows external quantum efficiency-luminance characteristics of the light-emitting element 5 and the light-emitting element 6. [Diagram 41] 4 shows emission spectra of light-emitting element 5 and light-emitting element 6. [Diagram 42] Normalized luminance-time change characteristics of light-emitting element 5 and light-emitting element 6. [Diagram 43] luminance-current density characteristics of light-emitting element 7; [Diagram 44] Current efficiency-luminance characteristics of light-emitting element 7. [Diagram 45] Luminance-voltage characteristics of light-emitting element 7. [Figure 46] Current-voltage characteristics of light-emitting element 7. [Figure 47] External quantum efficiency-luminance characteristics of light-emitting element 7. [Figure 48] Emission spectrum of light-emitting element 7. [Figure 49] Luminance-current density characteristics of light-emitting element 8. [Figure 50] Current efficiency-luminance characteristics of light-emitting element 8. [Figure 51] Luminance-voltage characteristics of light-emitting element 8. [Figure 52] Current-voltage characteristics of light-emitting element 8. [Figure 53] External quantum efficiency-luminance characteristics of light-emitting element 8. [Figure 54] Emission spectrum of light-emitting element 8. [Figure 55] luminance-current density characteristics of light-emitting element 9 and light-emitting element 10. [Figure 56] Current efficiency-luminance characteristics of the light-emitting element 9 and the light-emitting element 10. [Figure 57] luminance-voltage characteristics of light-emitting element 9 and light-emitting element 10. [Figure 58] 4 shows current-voltage characteristics of light-emitting element 9 and light-emitting element 10. [Figure 59] 4 shows external quantum efficiency-luminance characteristics of the light-emitting element 9 and the light-emitting element 10. [Figure 60] 4 shows emission spectra of light-emitting element 9 and light-emitting element 10. [Figure 61] Normalized luminance-time change characteristics of light-emitting element 9 and light-emitting element 10. [Figure 62] luminance-current density characteristics of light-emitting element 11 and light-emitting element 12. [Figure 63] Current efficiency-luminance characteristics of the light-emitting element 11 and the light-emitting element 12. [Figure 64] luminance-voltage characteristics of light-emitting element 11 and light-emitting element 12. [Figure 65] Current-voltage characteristics of light-emitting element 11 and light-emitting element 12. [Figure 66] 4 shows external quantum efficiency-luminance characteristics of the light-emitting element 11 and the light-emitting element 12. [Figure 67] 4 shows emission spectra of light-emitting element 11 and light-emitting element 12. [Figure 68] Normalized luminance-time change characteristics of light-emitting element 11 and light-emitting element 12. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0070] Hereinafter, the embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it will be easily understood by those skilled in the art that the form and details of the present invention can be modified in various ways without departing from the spirit and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the description of the embodiments shown below.

[0071] (Embodiment 1) An organic compound according to one embodiment of the present invention is an organic compound represented by the following general formula (G1) or general formula (G2).

[0072] [ka]

[0073] In the general formula (G1), R 1 ~R 10 one of which is a group represented by the following general formula (g1), and the rest each independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0074] [ka]

[0075] In addition, in general formula (G2), R 11 ~R 20one of which is a group represented by the following general formula (g1), and the rest each independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0076] [ka]

[0077] In the general formula (g1), Ar 3 , Ar 4 each independently represents any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the following general formula (g2) to the following general formula (g4). 1 , Ar 2 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms; n and m each independently represent an integer of 0 to 2; 3 is a group represented by the following general formula (g4), n is 1 or 2, and Ar 4 is a group represented by the following general formula (g4), m is 1 or 2. When n is 2, two Ar 1 may be different or the same, and similarly, when m is 2, two Ar 2 may be different or the same. 3 , Ar 4 When is an aromatic hydrocarbon group having 6 to 10 carbon atoms and has a substituent, the substituent is one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and groups represented by the following general formulas (g2) to (g4):

[0078] [ka]

[0079] In general formula (g2), R 31 ~R 40 represents a single bond, and the nitrogen atom in the above general formula (g1), Ar 3 or Ar 4 The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0080] In addition, in the general formula (g3), R 41 ~R 50 represents a single bond, and the nitrogen atom in the above general formula (g1), Ar 3 or Ar 4 The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0081] In addition, in the general formula (g4), R 51 ~R 60 represents a single bond, and Ar 3 or Ar 4 The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

[0082] In the above general formula (G1), R 1 , R 8 and R 10 In particular, an organic compound in which any one of R in the general formula (G1) is a group represented by the above general formula (g1) is preferable because it can be easily synthesized with a small number of steps required for synthesis, and can provide a highly reliable element. 10The organic compound in which is a group represented by the above general formula (g1) has a high phosphorescence level and can therefore be suitably used in a phosphorescent device.

[0083] In addition, R in the above general formula (G2) 18 or R 20 In the organic compound in which any one of R in the general formula (G2) is a group represented by the above general formula (g1), the number of steps required for synthesis is small and the synthesis can be easily performed, which is preferable. In addition, a light-emitting element using the organic compound is preferable because it can be a highly reliable light-emitting element. 20 The organic compound in which is a group represented by the above general formula (g1) has a high phosphorescence level and can therefore be suitably used in a phosphorescent device.

[0084] The above general formula R 1 ~R 20 and R 31 ~R 60 Specific examples of the substituent that can be applied to include the substituents represented by the following structural formulae (1-1) to (1-37) and the substituents represented by the following structural formulae (2-1) to (2-13), etc. The substitution positions in the following structural formulae (2-1) to (2-13) are not important.

[0085] [ka]

[0086] [ka]

[0087] Ar 3 , Ar 4each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, or any one of the groups represented by the above general formulae (g2) to (g4). Specific examples of the substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms include groups represented by the following structural formulae (1-38) and (1-39). Note that these may be substituted at any position. These may also have a substituent.

[0088] [ka]

[0089] Ar 3 , Ar 4 is an aromatic hydrocarbon group having 6 to 10 carbon atoms, and when it further has a substituent, the substituent may be any one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a group represented by the above general formulas (g2) to (g4), and specific examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, and a haloalkyl group having 1 to 6 carbon atoms include those represented by the following structural formulas (1-1) to (1-37). Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

[0090] [ka]

[0091] Ar 3 , Ar 4 and Ar having a substituent 3 , Ar 4 Specific examples of the group include groups represented by the following structural formulas (1-100) to (1-134).

[0092] [ka]

[0093] Also, Ar 1 and Ar 2 is a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and representative examples include the following. Note that these may be substituted at any position. In addition, they may have a substituent.

[0094] [ka]

[0095] Also, n is 2 and there are two Ar 1 are different from each other, and m is 2 and there are two Ar 2 Examples where are different are shown in the following structural formulas (1-40) to (1-74).

[0096] [ka]

[0097] In the organic compound having the above structure, the Ar 1 and the Ar 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, 3 and Ar 4 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, it is preferable because a bulky skeleton is not bonded to the amine skeleton, and therefore a material with high hole transport properties can be provided. In addition, since it does not have a large condensed ring hydrocarbon, it is difficult to accept electrons, and when used as a hole transport material in a device, it shows high electron blocking properties, and therefore it is preferable because a device with high luminous efficiency can be provided.

[0098] Also, n and m are 0, and Ar 3 and Ar 4In the case where n is a phenyl group and the 2- and 6-positions of the phenyl group are substituted with aromatic hydrocarbon groups, it is difficult to provide high hole transport properties because a bulky substituent is bonded to the amine structure, and therefore this is excluded from the organic compounds of the present invention. 1 , Ar 2 In the case where the skeleton bonded to the nitrogen atom is a benzene ring, i.e., where the compound has an aniline skeleton, a structure in which the 2- and 6-positions of the aniline skeleton are substituted with aromatic hydrocarbon groups is excluded from the organic compounds of the present invention, since it is difficult for such a structure to have high hole transport properties due to the bulky substituents bonded to the amine structure.

[0099] In the organic compound having the above structure, Ar 3 and Ar 4 is either a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, it is preferable because it is an organic compound having both high heat resistance and high hole transportability, and a transport layer with good film quality can be formed. In particular, when these are phenyl groups, it is more preferable because it shows good film quality, good hole transportability, and high electron blocking property.

[0100] In the organic compound having the above structure, Ar 1 , Ar 2 However, organic compounds having a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group are preferred because they have high heat resistance, can form a transport layer with good film quality, and have good hole transport properties. In particular, when these are phenylene groups, they have good film quality and good hole transport properties, making them a more preferred configuration.

[0101] In the organic compound having the above structure, an organic compound in which both n and m are 2 is preferred because it has both high hole transport properties and heat resistance.

[0102] In addition, among the organic compounds having the above-mentioned structure, an organic compound in which both n and m are 1 has high hole transport properties and heat resistance, and can be highly purified in the synthesis process, so that it can be suitably used in an organic EL device, which is a preferred structure.

[0103] Specific examples of the group represented by the above general formula (g1) are shown below.

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] [ka]

[0108] [ka]

[0109] [ka]

[0110] [ka]

[0111] [ka]

[0112] Specific examples of organic compounds having the above structure are shown below.

[0113]

change

[0114]

change

[0115]

change

[0116]

change

[0117]

change

[0118]

change

[0119]

change

[0120]

change

[0121]

change

[0122]

change

[0123]

change

[0124] [ka]

[0125] The above organic compounds can be synthesized according to the following synthesis scheme.

[0126] Here, in the above general formula (G1), R 10 The synthesis method of the organic compound represented by the following general formula (G1-a), which is a compound in which the group represented by R 1 ~R 9 Other organic compounds according to one embodiment of the present invention having various substituents at the corresponding substitution positions can also be synthesized by a similar method using starting materials having substituents corresponding to the corresponding substitution positions.

[0127] In addition, the substituent R in the following general formula (G1-a) and reaction schemes (a-1) and (a-2) 1 ~R 9 , substituent Ar 1 , Ar 2 Since the description of is the same as that of the general formula (G1) above, the description will be omitted.

[0128] As a method for synthesizing the organic compound represented by the general formula (G1-a), various reactions can be applied. For example, the organic compound represented by the general formula (G1-a) can be synthesized by carrying out the synthesis reaction shown below.

[0129] [ka]

[0130] <Method for synthesizing organic compound represented by general formula (G1-a)> The organic compound represented by the general formula (G1-a) of the present invention can be synthesized according to the following synthesis scheme (a-1) or (a-2).

[0131] First, the scheme (a-1) will be described. That is, a benzonaphthofuranylamino compound (G1-a) can be obtained by coupling a benzonaphthofuran compound (compound 1) with a diarylamine (compound 2). The synthesis scheme (a-1) is shown below.

[0132] [ka]

[0133] Next, the scheme (a-2) will be described. That is, by coupling a benzonaphthofuran compound (compound 3) with an aryl compound (compound 4), a benzonaphthofuranylamino compound (compound 5) can be obtained, and then by coupling compound 5 with an aryl compound (compound 6), the target benzonaphthofuranylamino compound (G1-a) can be obtained. The synthesis scheme (a-2) is shown below.

[0134] [ka]

[0135] In the above reaction schemes (a-1) and (a-2), X 1 and X 5 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group; X 2 represents hydrogen, an organotin group, etc., and X 3 and X 4 represents an amino group or an amino group having an organotin group, and X 3 and X 4 The other represents a chlorine, bromine, iodine, or triflate group.

[0136] In the synthesis schemes (a-1) and (a-2), when the Buchwald-Hartwig reaction using a palladium catalyst is performed, palladium compounds such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), and allylpalladium(II) chloride (dimer) and ligands such as tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, and di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)) can be used. In this reaction, an organic base such as sodium tert-butoxide, or an inorganic base such as potassium carbonate, cesium carbonate, sodium carbonate, etc. can be used. In this reaction, a solvent such as toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used.

[0137] In the synthesis schemes (a-1) and (a-2), when the Ullmann reaction is carried out using copper or a copper compound, X 1 and X 5 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group; X 2 represents hydrogen, an organotin group, etc., and X 3 and X 4 Either one of them represents an amino group, and X 3 and X 4The other represents chlorine, bromine, iodine, or a triflate group. Copper or a copper compound can be used in this reaction. Examples of the base used include inorganic bases such as potassium carbonate. Examples of solvents that can be used in this reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, and benzene. In the Ullmann reaction, it is preferable to use DMPU or xylene, which have high boiling points, because a reaction temperature of 100°C or higher allows the target product to be obtained in a shorter time and with a higher yield. In addition, a reaction temperature of 150°C or higher is even more preferable, so it is more preferable to use DMPU.

[0138] This synthesis example is 1 ~R 9 Compounds having (g1) in R can be synthesized in a similar manner. For example, 10 R, which is a substitution position different from 1 ~R 9 When synthesizing (G1) having an amino group such as that of general formula (g1) or general formula (g5) at any position of X, 1 When synthesizing (G1) according to (a-2), a benzonaphthofuran compound corresponding to compound 1 having the formula: 3 If a benzonaphthofuran compound corresponding to compound 3 having the formula R 1 ~R 9 It is possible to obtain an object having (g1).

[0139] Next, in the above general formula (G2), R 20 The synthesis method of an organic compound represented by the following general formula (G2-a), which is a compound in which R has a group represented by (g1), is described below. 11 ~R 19 An organic compound according to one embodiment of the present invention having various substituents represented by the following formula (I) can also be synthesized by a similar method using a raw material having a substituent corresponding to the corresponding substitution position.

[0140] In addition, the substituent R in the following general formula (G2-a) and reaction schemes (b-1) and (b-2) 11 ~R 19 , substituent Ar 1 , Ar 2 Since the description of is the same as that of the general formula (G2) above, the description will be omitted.

[0141] Various reactions can be applied as a method for synthesizing the organic compound represented by the general formula (G2-a). For example, the organic compound represented by the general formula (G2-a) can be synthesized by carrying out the synthesis reaction shown below.

[0142] [ka]

[0143] <Method for synthesizing organic compound represented by general formula (G2-a)> The organic compound represented by the general formula (G2-a) of the present invention can be synthesized according to the following synthesis scheme (b-1) or (b-2).

[0144] First, the scheme (b-1) will be described. That is, the benzonaphthofuran compound (compound 7) and the diarylamine (compound 2) are coupled to obtain the benzonaphthofuranylamino compound (G2-a). The synthesis scheme (b-1) is shown below.

[0145] [ka]

[0146] Next, the scheme (b-2) will be described. That is, by coupling a benzonaphthofuran compound (compound 8) with an aryl compound (compound 4), a benzonaphthofuranylamino compound (compound 9) can be obtained, and then by coupling compound 7 with an aryl compound (compound 6), the target benzonaphthofuranylamino compound (G2-a) can be obtained. The synthesis scheme (b-2) is shown below.

[0147] [ka]

[0148] X 5 and X 6 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group; X 2 represents hydrogen, an organotin group, etc., and X 4 and X 7 represents an amino group or an amino group having an organotin group, and X 4 and X 7 The other represents a chlorine, bromine, iodine, or triflate group.

[0149] In the synthesis schemes (b-1) and (b-2), when the Buchwald-Hartwig reaction using a palladium catalyst is carried out, a palladium compound such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), or allylpalladium(II) chloride (dimer) and a ligand such as tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, or di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)) can be used. In this reaction, an organic base such as sodium tert-butoxide, or an inorganic base such as potassium carbonate, cesium carbonate, sodium carbonate, etc. can be used. In this reaction, a solvent such as toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used.

[0150] In the synthesis schemes (b-1) and (b-2), when the Ullmann reaction is carried out using copper or a copper compound, X 5 and X 6 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group; X 2 represents hydrogen, an organotin group, etc., and X 4 and X 7 Either one of them represents an amino group, and X 4 and X 7The other represents chlorine, bromine, iodine, or a triflate group. Copper or a copper compound can be used in this reaction. Examples of the base used include inorganic bases such as potassium carbonate. Examples of solvents that can be used in this reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, and benzene. In the Ullmann reaction, it is preferable to use DMPU or xylene, which have high boiling points, because a reaction temperature of 100°C or higher allows the target product to be obtained in a shorter time and with a higher yield. In addition, a reaction temperature of 150°C or higher is even more preferable, so it is more preferable to use DMPU.

[0151] This synthesis example is 11 ~R 19 Compounds having an amino group at the corresponding position can also be synthesized in a similar manner using benzonaphthofuran compounds having a chlorine, bromine, iodine, or triflate group at the corresponding position. For example, R 20 R, which is a substitution position different from 11 ~R 19 When synthesizing (G2) having an amino group at any one of the positions, when synthesizing (G2) according to (b-1), 6 When (G2) is synthesized according to (b-2) using a benzonaphthofuran compound corresponding to compound 7 having the formula: 7 If a benzonaphthofuran compound corresponding to compound 8 having the formula R 11 ~R 19 It is possible to obtain an object having (g1).

[0152] (Embodiment 2)

[0153] A light-emitting element according to one embodiment of the present invention is illustrated in Fig. 1. The light-emitting element according to one embodiment of the present invention includes a first electrode 101, a second electrode 102, and an EL layer 103, and the EL layer includes a hole-transporting material containing the above-described organic compound.

[0154] The EL layer 103 includes a light-emitting layer 113 and may include a hole-transport layer 112. The light-emitting layer 113 contains a light-emitting material and a host material, and the light-emitting element of one embodiment of the present invention emits light from the light-emitting material. The hole-transport material of one embodiment of the present invention may be included in either the light-emitting layer 113 or the hole-transport layer 112.

[0155] In addition, in FIG. 1, a hole injection layer 111, an electron transport layer 114, and an electron injection layer 115 are illustrated, but the configuration of the light emitting element is not limited to these.

[0156] The hole transport material can also be used as a host material. In addition, the hole transport material may be co-evaporated with an electron transport material to form an exciplex of the electron transport material and the hole transport material. By forming an exciplex having an appropriate emission wavelength, effective energy transfer to the light emitting material can be realized, and a light emitting element having high efficiency and good life can be provided.

[0157] In addition, since the hole transport material has a good hole transport property, it is effective to use the hole transport material in the hole transport layer 112. In particular, it is preferable when the hole injection layer 111 is provided between the hole transport layer 112 and the first electrode 101, and an organic compound having an acceptor property that facilitates hole injection from the electrode is used in the hole injection layer 111.

[0158] When holes are injected using an organic compound having an acceptor property, the compound contained in the hole transport layer 112 in contact with the hole injection layer 111 is preferably a hole transport material with a relatively shallow HOMO level in order to facilitate the extraction of electrons by the organic compound having an acceptor property. However, since it is difficult to inject holes into the light-emitting layer 113 using a hole transport material with a shallow HOMO level, when the hole transport layer 112 made of such a hole transport material with a shallow HOMO level is formed in contact with the light-emitting layer 113, carriers are accumulated at the interface, which may cause a decrease in the life and efficiency of the light-emitting element. Here, by providing a layer containing the organic compound described in embodiment 1 between the hole transport material with a shallow HOMO level and the light-emitting layer 113, it is possible to smoothly inject holes into the light-emitting layer, thereby improving the life and efficiency of the light-emitting element.

[0159] That is, the hole transport layer 112 has a first hole transport layer 112-1 and a second hole transport layer 112-2 from the hole injection layer 111 side, the first hole transport layer contains a first hole transport material, the second hole transport layer contains an organic compound described in the above embodiment 1, and a light-emitting element having a HOMO level of the organic compound described in embodiment 1 that is deeper than the HOMO level of the first hole transport material can be a light-emitting element with good lifetime and efficiency, which is a preferred configuration. Note that when the HOMO level of the first hole transport material is −5.4 eV or higher, this is a preferred configuration because it is easy to extract electrons from the organic compound having acceptor properties.

[0160] In addition, it is preferable that the difference between the HOMO level of the first hole transport material and the HOMO level of the organic compound described in embodiment 1 is 0.3 eV or less, more preferably 0.2 eV or less, because this facilitates the injection of holes from the first hole transport layer 112-1 to the second hole transport layer 112-2.

[0161] The hole transport layer 112 may further include a third hole transport layer 112-3 between the second hole transport layer 112-2 and the light emitting layer, and the third hole transport layer 112-3 may include a third hole transport material. In this case, the third hole transport material preferably has a HOMO level deeper than the HOMO level of the organic compound described in embodiment 1 contained in the second hole transport layer 112-2. The difference between the HOMO level of the third hole transport material and the HOMO level of the organic compound described in embodiment 1 contained in the second hole transport layer 112-2 is preferably 0.3 eV or less, more preferably 0.2 eV or less.

[0162] In addition, it can be said that a more preferable configuration is one in which the HOMO level of the third hole-transporting material is the same as that of the host material or the third hole-transporting material is located deeper than the host material, since holes are appropriately transported into the light-emitting layer, resulting in good lifetime and efficiency.

[0163] In addition, when the HOMO level of the light-emitting material is shallower (higher) than that of the host material, the ratio of holes injected into the light-emitting material increases depending on the position of the HOMO level of the hole transport layer, and the holes are trapped in the light-emitting material, which may cause a decrease in life due to the bias of the light-emitting region. In such a case, the application of the above-mentioned light-emitting device configuration is suitable. A blue fluorescent device can be cited as an example that is likely to have such a configuration. The configuration of the present invention can be particularly preferably applied to aromatic diamine compounds that emit good blue fluorescence, especially pyrene diamine compounds, and the like, and a light-emitting device with good life, efficiency, and chromaticity can be obtained.

[0164] Next, examples of the detailed structure and materials of the light-emitting element will be described. As described above, the light-emitting element of one embodiment of the present invention has an EL layer 103 composed of multiple layers between a pair of electrodes, that is, a first electrode 101 and a second electrode 102, and the EL layer 103 includes at least a hole-injection layer 111, a hole-transport layer 112, and a light-emitting layer 113 from the first electrode 101 side.

[0165] The layers other than those included in the EL layer 103 are not particularly limited, and various layer structures can be applied, such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier blocking layer, an exciton blocking layer, and a charge generating layer.

[0166] The first electrode 101 is preferably formed using a metal, alloy, conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, and indium oxide containing tungsten oxide and zinc oxide (IWZO). These conductive metal oxide films are usually formed by a sputtering method, but may be formed by applying a sol-gel method or the like. As an example of a manufacturing method, indium oxide-zinc oxide may be formed by a sputtering method using a target containing indium oxide and 1 to 20 wt % zinc oxide. Indium oxide containing tungsten oxide and zinc oxide (IWZO) may also be formed by a sputtering method using a target containing indium oxide and 0.5 to 5 wt % tungsten oxide and 0.1 to 1 wt % zinc oxide. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), and nitrides of metal materials (e.g., titanium nitride). Graphene can also be used. By using a composite material described later for the layer in contact with the first electrode 101 in the EL layer 103, it becomes possible to select an electrode material regardless of the work function.

[0167] Regarding the stacked structure of the EL layer 103, two types of structures will be described in this embodiment: a structure having an electron transport layer 114 and an electron injection layer 115 in addition to a hole injection layer 111, a hole transport layer 112, and a light-emitting layer 113 as shown in Fig. 1A, and a structure having an electron transport layer 114, an electron injection layer 115, and a charge generation layer 116 in addition to a hole injection layer 111, a hole transport layer 112, and a light-emitting layer 113 as shown in Fig. 1B. Materials constituting each layer will be specifically described below.

[0168] The hole injection layer 111 is a layer containing a substance having an acceptor property. In the structure of one embodiment of the present invention, the structure is more suitable when an organic compound having an acceptor property is used. As the organic compound having an acceptor property, a compound having an electron-withdrawing group (a halogen group or a cyano group) can be used, and examples of the organic compound having an acceptor property include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), 3,6-difluoro-2,5,7,7,8,8-hexacyanoquinodimethane, chloranil, and 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN). As the organic compound having an acceptor property, a compound in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of heteroatoms, such as HAT-CN, is thermally stable and is preferable. An organic compound having acceptor properties can extract electrons from an adjacent hole transport layer (or hole transport material) when an electric field is applied.

[0169] In the case where an organic compound having an acceptor property is not used for the hole injection layer 111, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, or the like can be used as a substance having an acceptor property. 2The hole injection layer 111 can also be formed from a phthalocyanine compound such as copper phthalocyanine (CuPC) or copper phthalocyanine (Pc), an aromatic amine compound such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB) or N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), or a polymer such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), or the like.

[0170] In addition, a composite material in which an acceptor substance is contained in a substance having a hole-transporting property can be used as the hole-injection layer 111. By using a composite material in which an acceptor substance is contained in a substance having a hole-transporting property, a material for forming an electrode can be selected regardless of the work function. That is, not only a material having a high work function but also a material having a low work function can be used as the first electrode 101. Examples of the acceptor substance include organic compounds having an acceptor property such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, and 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), and transition metal oxides. In addition, oxides of metals belonging to Groups 4 to 8 of the periodic table can also be used. As the oxides of metals belonging to Groups 4 to 8 in the periodic table, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, etc. are preferred because of their high electron-accepting properties. Among them, molybdenum oxide is particularly preferred because it is stable in the air, has low hygroscopicity, and is easy to handle.

[0171] As the hole transporting substance used in the composite material, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, and polymer compounds (oligomers, dendrimers, polymers, etc.) can be used. -6 cm2 It is preferable that the material has a hole mobility of 1 / Vs or more. Specific examples of organic compounds that can be used as the hole-transporting material in the composite material are listed below.

[0172] Examples of aromatic amine compounds that can be used in the composite material include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B). Specific examples of the carbazole derivative include 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-phenyl Carbazole (abbreviation: PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, and the like can be used.Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), 2-tert- Butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene, etc. In addition, pentacene, coronene, etc. can also be used. It may have a vinyl skeleton. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi) and 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA). Note that the organic compound of one embodiment of the present invention can also be used. Note that in this case, it is preferable to use F6-TCNNQ as the acceptor substance.

[0173] In addition, polymer 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.

[0174] By forming the hole injection layer 111, the hole injection property is improved, and a light emitting element with a low driving voltage can be obtained. In addition, an organic compound having an acceptor property is an easy-to-use material because it is easy to evaporate and form a film.

[0175] The hole transport layer 112 is formed by containing a hole transport material. -6 cm 2 / Vs or more. The hole-transport layer 112 preferably contains a hole-transport material of one embodiment of the present invention. By containing the organic compound described in Embodiment 1 in the hole-transport layer 112, a light-emitting element with long lifetime and high efficiency can be obtained.

[0176] In particular, when an organic compound having an acceptor property is used as the hole injection layer 111, at least the hole injection layer 111 is formed of two layers, a first hole transport layer and a second hole transport layer, and the first hole transport layer contains a first hole transport material having a relatively shallow HOMO level, and the second hole transport layer contains the organic compound described in Embodiment 1, whereby a light-emitting element with a long lifetime and high efficiency can be obtained.

[0177] The difference between the LUMO level of the organic compound having acceptor properties and the HOMO level of the first hole transport material is not particularly limited because it varies depending on the strength of the acceptor properties of the organic compound having acceptor properties, but holes can be injected if the difference in levels is approximately 1 eV or less. When HAT-CN is used as the organic compound having acceptor properties, the LUMO level of HAT-CN is estimated to be -4.41 eV from cyclic voltammetry measurement, so the HOMO level of the first hole transport material is preferably -5.4 eV or more. However, if the HOMO level of the first hole transport material becomes too high, the hole injection into the second hole transport material will be poor. In addition, since the work function of an anode such as ITO is around -5 eV, it is disadvantageous to use a first hole transport material with a higher HOMO level than that. Therefore, the HOMO level of the first hole transport material is preferably -5.0 eV or less.

[0178] A third hole transport layer may be further formed between the second hole transport layer and the light emitting layer. The third hole transport layer contains a third hole transport material.

[0179] The first hole transport layer, the second hole transport layer, and the third hole transport layer have been described above, so repeated description will be omitted. Note that, as for the hole transport material contained in each of them, a material that matches the relationship between the layers may be selected from the materials having hole transport properties described above or from various other materials having hole transport properties.

[0180] The light-emitting layer 113 is a layer containing a host material and a light-emitting material. The light-emitting material may be a fluorescent material, a phosphorescent material, a material exhibiting thermally activated delayed fluorescence (TADF), or other light-emitting material. The light-emitting layer 113 may be a single layer or may be composed of multiple layers containing different light-emitting materials. Note that one embodiment of the present invention can be more suitably applied to the case where the light-emitting layer 113 is a layer that exhibits fluorescent light, in particular, a layer that exhibits blue fluorescent light.

[0181] Examples of materials that can be used as the fluorescent substance in the light-emitting layer 113 include the following: Other fluorescent substances can also be used.

[0182] 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'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), 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'-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-(1 0-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), 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-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N',N'',N'',N'''',N'''-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, N-(9,10-diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPA BPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA) Coumarin 545T, N,N'-diphenylquinacridone, (abbreviation: DPQd), rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6 -methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine Amine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), N,N'-(pyren-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), and the like. In particular, condensed aromatic diamine compounds, such as pyrene diamine compounds, such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred because they have high hole trapping properties, excellent luminous efficiency, and excellent reliability.

[0183] Examples of materials that can be used as the phosphorescent material in the light-emitting layer 113 include the following:

[0184] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]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-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp) 3 ]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me) 3]), and fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi) 3 ]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me 3 ]) and bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir(CF 3 ppy) 2 (pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ] Organometallic iridium complexes with phenylpyridine derivatives having electron-withdrawing groups as ligands, such as iridium(III) acetylacetonate (abbreviation: FIr(acac)), are compounds that exhibit blue phosphorescence and have emission peaks between 440 nm and 520 nm.

[0185] In addition, 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-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm) 2 and organometallic iridium complexes with pyrimidine skeletons such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinate)iridium(III) (abbreviation: [Ir(mppr-Me 2 (acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinate)iridium(III) (abbreviation: [Ir(mppr-iPr) 2 Organometallic iridium complexes with pyrazine skeletons 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 ]), bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(pq) 2In addition to organometallic iridium complexes with pyridine skeletons such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)]), 3 These are compounds that mainly exhibit green phosphorescence, with an emission peak at 500 nm to 600 nm. In addition, organometallic iridium complexes having a pyrimidine skeleton are particularly preferred because they are remarkably excellent in reliability and luminous efficiency.

[0186] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm) 2 (dpm)]), bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm) 2 and organometallic iridium complexes with pyrimidine skeletons such as (acetylacetonato)bis(2,3,5-triphenylpyrazinate)iridium(III) (abbreviation: [Ir(tppr) 2 (acac)]), bis(2,3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr) 2 (dpm])]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq) 2 Organometallic iridium complexes with pyrazine skeletons such as tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq) 3 ]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(piq) 2In addition to organometallic iridium complexes with pyridine skeletons such as iridium complexes with pyridine skeletons such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM) 3 (Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA) 3 These are compounds that exhibit red phosphorescence, with emission peaks at 600 to 700 nm. In addition, organometallic iridium complexes with a pyrazine skeleton can emit red light with good chromaticity.

[0187] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting materials may be selected and used.

[0188] Examples of TADF materials that can be used include fullerene and its derivatives, acridine and its derivatives, and eosin derivatives. Examples of metal-containing porphyrins that can be used include those containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of metal-containing porphyrins include protoporphyrin-tin fluoride complex (SnF), which is shown in the following structural formula: 2 (Proto IX)), mesoporphyrin-tin fluoride complex (SnF 2 (Meso IX)), hematoporphyrin-tin fluoride complex (SnF 2 (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF 2 (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF 2 (OEP)), etioporphyrin-tin fluoride complex (SnF 2 (Etio I)), octaethylporphyrin-platinum chloride complex (PtCl 2OEP) etc.

[0189] [ka]

[0190] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ) shown in the following structural formula, 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTzn), 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 Heterocyclic compounds having both π-electron rich heteroaromatic rings and π-electron deficient heteroaromatic rings, such as bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), etc., can also be used. The heterocyclic compound has a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, and therefore has high electron transport and hole transport properties, which is preferable. In addition, in a substance in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded to each other, the donor property of the π-electron rich heteroaromatic ring and the acceptor property of the π-electron deficient heteroaromatic ring are both strong, and S 1 Level and T 1This is particularly preferred because the energy difference between the levels is small, and therefore thermally activated delayed fluorescence can be efficiently obtained. Note that, instead of the π-electron-deficient heteroaromatic ring, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used.

[0191] [ka]

[0192] As the host material of the light-emitting layer, various carrier transporting materials such as a material having an electron transporting property or a material having a hole transporting property can be used.

[0193] Examples of materials having hole transport properties include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), 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: BP AFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: P CBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF) and other aromatic amines. Compounds with a carbazole skeleton, such as 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), and 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), and compounds with a carbazole skeleton, such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,Examples of the compounds include compounds having a thiophene skeleton such as 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), and compounds having a furan skeleton such as 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). Among the above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferable because they have good reliability, high hole transport properties, and contribute to reducing the driving voltage. In addition, the organic compounds described in embodiment 1 can also be suitably used.

[0194] An example of a material having electron transport properties is bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq 2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and other metal complexes. p-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1,2,4-triazole (abbreviation: TAZ), We have developed heterocyclic compounds with polyazole skeletons such as 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: 2mDBTBPDBq-II), and 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II). Examples of heterocyclic compounds having a diazine skeleton include 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), and 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), and heterocyclic compounds having a pyridine skeleton include 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), and 1,3,5-tri[3-(3-pyridyl)-phenyl]benzene (abbreviation: TmPyPB).Among the above, heterocyclic compounds having a diazine skeleton and heterocyclic compounds having a pyridine skeleton are preferable because of their high reliability. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties and contribute to reducing the driving voltage.

[0195] When a fluorescent material is used as the light-emitting material, a material having an anthracene skeleton is suitable as the host material. When a material having an anthracene skeleton is used as the host material of the fluorescent material, it is possible to realize a light-emitting layer having both good light-emitting efficiency and durability. Since many materials having an anthracene skeleton have a deep HOMO level, one embodiment of the present invention can be suitably applied. As a material having an anthracene skeleton to be used as a host material, a diphenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton, is preferable because it is chemically stable. In addition, when the host material has a carbazole skeleton, it is preferable because the hole injection and transport properties are improved, but when the host material contains a benzocarbazole skeleton in which a benzene ring is further condensed to carbazole, the HOMO is shallower by about 0.1 eV than carbazole, making it easier for holes to enter, which is more preferable. In particular, when the host material contains a dibenzocarbazole skeleton, it is preferable because the HOMO is shallower by about 0.1 eV than carbazole, making it easier for holes to enter, and it also has excellent hole transport properties and high heat resistance. Therefore, a more preferable host material is a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). From the viewpoint of the hole injection / transport property, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton. Examples of such a substance include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9 -anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: FLPPA), and the like.In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred choices since they exhibit very good properties.

[0196] Note that the light-emitting element of one embodiment of the present invention is preferably used as a light-emitting element that emits blue fluorescent light.

[0197] The host material may be a mixture of a plurality of substances, and when a mixture of host materials is used, it is preferable to mix a material having an electron transporting property with a material having a hole transporting property. By mixing a material having an electron transporting property with a material having a hole transporting property, the transporting property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The content ratio of the material having a hole transporting property to the material having an electron transporting property may be 1:9 to 9:1 (material having a hole transporting property:material having an electron transporting property).

[0198] In addition, these mixed materials may form an exciplex. It is preferable to select a combination that forms an exciplex that emits light that overlaps with the wavelength of the lowest energy absorption band of the light-emitting material, because this makes energy transfer smooth and allows efficient light emission. In addition, the use of this structure is preferable because the driving voltage is reduced.

[0199] The electron transport layer 114 is a layer containing a substance having an electron transport property. As the substance having an electron transport property, any of the substances exemplified above as the substance having an electron transport property that can be used as the host material can be used.

[0200] Between the electron transport layer 114 and the second electrode 102, an electron injection layer 115 made of lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2The electron injection layer 115 may be a layer containing an alkali metal or alkaline earth metal or a compound thereof, such as ZnO, ZnSe ...

[0201] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1(B)). The charge generation layer 116 is a layer capable of injecting holes into a layer in contact with the cathode side of the layer and electrons into a layer in contact with the anode side of the layer by applying a potential. The charge generation layer 116 includes at least a P-type layer 117. The P-type layer 117 is preferably formed using the composite material listed above as a material capable of forming the hole injection layer 111. The P-type layer 117 may also be formed by laminating a film containing an acceptor material and a film containing a hole transport material, both of which are materials that constitute the composite material. By applying a potential to the P-type layer 117, electrons are injected into the electron transport layer 114 and holes are injected into the second electrode 102, which is the cathode, and the light-emitting element operates.

[0202] In addition, the charge generating layer 116 preferably includes, in addition to the P-type layer 117, either or both of an electron relay layer 118 and an electron injection buffer layer 119.

[0203] The electron relay layer 118 contains at least a substance having an electron transporting property, and has a function of preventing an interaction between the electron injection buffer layer 119 and the P-type layer 117 and smoothly transferring electrons. The LUMO level of the substance having an electron transporting property contained in the electron relay layer 118 is preferably between the LUMO level of the acceptor substance in the P-type layer 117 and the LUMO level of the substance contained in the layer in contact with the charge generating layer 116 in the electron transport layer 114. The specific energy level of the LUMO level of the substance having an electron transporting property used in the electron relay layer 118 is -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. Note that, as the substance having an electron transporting property used in the electron relay layer 118, a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand is preferably used.

[0204] The electron injection buffer layer 119 can be made of a material with high electron injection properties, such as an alkali metal, an alkaline earth metal, a rare earth metal, or a compound thereof (an alkali metal compound (including an oxide such as lithium oxide, a halide, or a carbonate such as lithium carbonate or cesium carbonate), an alkaline earth metal compound (including an oxide, a halide, or a carbonate), or a rare earth metal compound (including an oxide, a halide, or a carbonate)).

[0205] In addition, when the electron-injection buffer layer 119 is formed containing a substance having an electron-transporting property and a donor substance, as the donor substance, an alkali metal, an alkaline earth metal, a rare earth metal, and a compound thereof (an alkali metal compound (including an oxide such as lithium oxide, a halide, or a carbonate such as lithium carbonate or cesium carbonate), an alkaline earth metal compound (including an oxide, a halide, or a carbonate), or a rare earth metal compound (including an oxide, a halide, or a carbonate)), or an organic compound such as tetrathianaphthacene (abbreviation: TTN), nickelocene, or decamethylnickelocene can be used. Note that as the substance having an electron-transporting property, a material similar to the material constituting the electron-transporting layer 114 described above can be used.

[0206] The second electrode 102 may be made of a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include alkali metals such as lithium (Li) and cesium (Cs), elements belonging to Group 1 or Group 2 of the periodic table such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these elements (MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these elements. However, by providing an electron injection layer between the second electrode 102 and the electron transport layer, various conductive materials such as Al, Ag, ITO, indium oxide-tin oxide containing silicon or silicon oxide can be used as the second electrode 102 regardless of the magnitude of the work function. These conductive materials can be formed into a film by a dry method such as a vacuum deposition method or a sputtering method, an inkjet method, a spin coating method, etc. Also, they may be formed by a wet method using a sol-gel method, or may be formed by a wet method using a paste of a metal material.

[0207] In addition, various methods, whether dry or wet, can be used to form the EL layer 103. For example, a vacuum deposition method, a gravure printing method, an offset printing method, a screen printing method, an inkjet method, or a spin coating method may be used.

[0208] Moreover, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0209] The configuration of the layers provided between the first electrode 101 and the second electrode 102 is not limited to the above. However, a configuration in which a light-emitting region where holes and electrons recombine is provided at a position away from the first electrode 101 and the second electrode 102 is preferable so as to suppress quenching caused by the proximity of the light-emitting region to the metals used in the electrodes and the carrier injection layer.

[0210] In addition, the hole transport layer and electron transport layer in contact with the light-emitting layer 113, particularly the carrier transport layer close to the recombination region in the light-emitting layer 113, are preferably composed of a substance having a band gap larger than the band gap of the light-emitting material constituting the light-emitting layer or the light-emitting material contained in the light-emitting layer, in order to suppress energy transfer from excitons generated in the light-emitting layer.

[0211] Next, an embodiment of a light-emitting element having a structure in which multiple light-emitting units are stacked (also referred to as a stacked element or a tandem element) will be described with reference to FIG. 1(C). This light-emitting element has multiple light-emitting units between an anode and a cathode. One light-emitting unit has a structure almost similar to that of the EL layer 103 shown in FIG. 1(A). In other words, it can be said that the light-emitting element shown in FIG. 1(C) is a light-emitting element having multiple light-emitting units, and the light-emitting element shown in FIG. 1(A) or FIG. 1(B) is a light-emitting element having one light-emitting unit.

[0212] In Fig. 1(C), a first light-emitting unit 511 and a second light-emitting unit 512 are laminated between an anode 501 and a cathode 502, and a charge generation layer 513 is provided between the first light-emitting unit 511 and the second light-emitting unit 512. The anode 501 and the cathode 502 correspond to the first electrode 101 and the second electrode 102 in Fig. 1(A), respectively, and the same electrodes as those described in the description of Fig. 1(A) can be applied. In addition, the first light-emitting unit 511 and the second light-emitting unit 512 may have the same structure or different structures.

[0213] The charge generation layer 513 has a function of injecting electrons into one light-emitting unit and injecting holes into the other light-emitting unit when a voltage is applied between the anode 501 and the cathode 502. That is, in FIG. 1C, when a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the charge generation layer 513 may inject electrons into the first light-emitting unit 511 and inject holes into the second light-emitting unit 512.

[0214] The charge generation layer 513 is preferably formed to have the same structure as the charge generation layer 116 described in FIG. 1B. A composite material of an organic compound and a metal oxide has excellent carrier injection and carrier transport properties, and therefore can realize low-voltage driving and low-current driving. When the anode side surface of the light-emitting unit is in contact with the charge generation layer 513, the charge generation layer 513 can also function as a hole injection layer of the light-emitting unit, and therefore the light-emitting unit does not need to be provided with a hole injection layer.

[0215] Furthermore, when an electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer layer 119 plays the role of an electron injection layer in the light-emitting unit on the anode side, so that it is not necessarily necessary to form an electron injection layer in the light-emitting unit on the anode side.

[0216] 1C, a light-emitting element having two light-emitting units has been described, but the same can be applied to a light-emitting element having three or more light-emitting units stacked together. By disposing a plurality of light-emitting units between a pair of electrodes and separating them with a charge generation layer 513 as in the light-emitting element according to this embodiment, a high-luminance light-emitting element can be realized while keeping the current density low, and an element with a long life can be realized. In addition, a light-emitting device that can be driven at a low voltage and consumes low power can be realized.

[0217] In addition, by making the emission colors of the respective light-emitting units different, it is possible to obtain light emission of a desired color as the whole light-emitting element. For example, in a light-emitting element having two light-emitting units, it is possible to obtain a light-emitting element that emits white light as the whole light-emitting element by obtaining red and green emission colors from the first light-emitting unit and blue emission color from the second light-emitting unit.

[0218] In addition, each layer and electrode such as the above-mentioned EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and the charge generation layer can be formed by using, for example, a deposition method (including a vacuum deposition method), a droplet discharge method (also called an ink-jet method), a coating method, a gravure printing method, etc. In addition, they may contain a low molecular weight material, a medium molecular weight material (including an oligomer and a dendrimer), or a polymer material.

[0219] (Embodiment 3) In this embodiment mode, a light-emitting device using the light-emitting element described in Embodiment 1 will be described.

[0220] In this embodiment, a light-emitting device manufactured using the light-emitting element described in Embodiment 1 will be described with reference to Fig. 2. Fig. 2(A) is a top view showing the light-emitting device, and Fig. 2(B) is a cross-sectional view taken along the lines AB and CD in Fig. 2(A). This light-emitting device includes a driver circuit section (source line driver circuit) 601, a pixel section 602, and a driver circuit section (gate line driver circuit) 603, all of which are shown by dotted lines, for controlling light emission from the light-emitting element. Reference numeral 604 denotes a sealing substrate, 605 denotes a sealant, and the inside surrounded by the sealant 605 defines a space 607.

[0221] The lead wiring 608 is a wiring for transmitting signals input to the source line driving circuit 601 and the gate line driving circuit 603, and receives a video signal, a clock signal, a start signal, a reset signal, and the like from an FPC (flexible printed circuit) 609 serving as an external input terminal. Although only an FPC is shown here, a printed wiring board (PWB) may be attached to this FPC. In this specification, the light emitting device includes not only the light emitting device itself, but also a state in which an FPC or a PWB is attached to it.

[0222] Next, the cross-sectional structure will be described with reference to Fig. 2(B). A driver circuit portion and a pixel portion are formed on an element substrate 610, and here, a source line driver circuit 601 which is the driver circuit portion and one pixel in the pixel portion 602 are shown.

[0223] The element substrate 610 may be made of a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl fluoride), polyester, acrylic, or the like.

[0224] The structure of the transistor used in the pixel or the driver circuit is not particularly limited. For example, the transistor may be an inverted staggered type transistor or a staggered type transistor. In addition, the transistor may be a top-gate type transistor or a bottom-gate type transistor. The semiconductor material used for the transistor is not particularly limited, and for example, silicon, germanium, silicon carbide, gallium nitride, or the like may be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In-Ga-Zn-based metal oxide, may be used.

[0225] The crystallinity of a semiconductor material used for a transistor is not particularly limited, and any of an amorphous semiconductor and a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a crystalline region in a part) may be used. The use of a crystalline semiconductor is preferable because it can suppress deterioration of transistor characteristics.

[0226] Here, in addition to the transistors provided in the pixels and driver circuits, an oxide semiconductor is preferably used for semiconductor devices such as transistors used in touch sensors, which will be described later. In particular, an oxide semiconductor having a wider band gap than silicon is preferably used. By using an oxide semiconductor having a wider band gap than silicon, the current in the off state of the transistor can be reduced.

[0227] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn), and more preferably contains an oxide represented by In-M-Zn oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0228] In particular, it is preferable to use, as the semiconductor layer, an oxide semiconductor film which has a plurality of crystal parts whose c-axes are oriented perpendicular to a surface on which the semiconductor layer is formed or a top surface of the semiconductor layer and which has no grain boundaries between adjacent crystal parts.

[0229] By using such a material for the semiconductor layer, fluctuations in electrical characteristics are suppressed, and a highly reliable transistor can be realized.

[0230] In addition, the transistor having the above-mentioned semiconductor layer can hold charge accumulated in a capacitance through the transistor for a long period of time due to its low off-state current. By applying such a transistor to a pixel, it is possible to stop a driver circuit while maintaining the gray level of an image displayed in each display region. As a result, an electronic device with extremely low power consumption can be realized.

[0231] It is preferable to provide an undercoat film in order to stabilize the characteristics of the transistor. The undercoat film can be prepared as a single layer or a multilayer structure using an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film. The undercoat film can be formed by a sputtering method, a CVD (Chemical Vapor Deposition) method (such as a plasma CVD method, a thermal CVD method, or a MOCVD (Metal Organic CVD) method), an ALD (Atomic Layer Deposition) method, a coating method, a printing method, or the like. Note that the undercoat film need not be provided if it is not necessary.

[0232] The FET 623 indicates one of the transistors formed in the driving circuit section 601. The driving circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. Although the present embodiment shows a driver-integrated type in which a driving circuit is formed on a substrate, this is not necessarily required, and the driving circuit may be formed externally instead of on the substrate.

[0233] In addition, the pixel portion 602 is formed by a plurality of pixels including a switching FET 611, a current control FET 612, and a first electrode 613 electrically connected to the drain of the FET 612. However, the present invention is not limited to this, and the pixel portion may be formed by combining three or more FETs and a capacitive element.

[0234] An insulator 614 is formed to cover an end portion of the first electrode 613. Here, the insulator 614 can be formed by using a positive type photosensitive acrylic resin film.

[0235] In order to improve the covering ability of an EL layer or the like to be formed later, a curved surface having a curvature is formed at the upper end or lower end of the insulator 614. For example, when a positive type photosensitive acrylic is used as the material of the insulator 614, it is preferable that only the upper end of the insulator 614 has a curved surface having a radius of curvature (0.2 μm to 3 μm). In addition, either a negative type photosensitive resin or a positive type photosensitive resin can be used as the insulator 614.

[0236] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, it is desirable to use a material with a large work function as a material used for the first electrode 613 that functions as an anode. For example, in addition to a single layer film such as an ITO film, an indium tin oxide film containing silicon, an indium oxide film containing 2 to 20 wt % zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, or a Pt film, a laminated structure of a titanium nitride film and a film mainly composed of aluminum, or a three-layer structure of a titanium nitride film, a film mainly composed of aluminum, and a titanium nitride film, can be used. Note that a laminated structure provides low resistance as wiring, good ohmic contact, and can further function as an anode.

[0237] The EL layer 616 is formed by various methods such as a deposition method using a deposition mask, an inkjet method, a spin coating method, etc. The EL layer 616 includes the configuration described in the embodiment 1. Other materials constituting the EL layer 616 may be low molecular weight compounds or high molecular weight compounds (including oligomers and dendrimers).

[0238] Furthermore, the second electrode 617 formed on the EL layer 616 and functioning as a cathode is preferably made of a material having a small work function (such as Al, Mg, Li, Ca, or alloys or compounds thereof (MgAg, MgIn, AlLi, etc.)). When light generated in the EL layer 616 is transmitted through the second electrode 617, the second electrode 617 is preferably made of a laminate of a thin metal thin film and a transparent conductive film (such as ITO, indium oxide containing 2 to 20 wt % zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.).

[0239] Note that a light-emitting element is formed with the first electrode 613, the EL layer 616, and the second electrode 617. The light-emitting element is the light-emitting element described in Embodiment 1. Note that a pixel portion is formed with a plurality of light-emitting elements, but the light-emitting device in this embodiment may include both the light-emitting element described in Embodiment 1 and a light-emitting element having a structure other than that.

[0240] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with a sealant 605, a structure is formed in which a light emitting element 618 is provided in a space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealant 605. The space 607 is filled with a filler, and may be filled with an inert gas (nitrogen, argon, etc.) or with a sealant. A recess is formed in the sealing substrate, and a desiccant is provided therein to suppress deterioration due to the influence of moisture, which is a preferable configuration.

[0241] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is also preferable that these materials are as moisture and oxygen impermeable as possible. In addition to glass and quartz substrates, materials that can be used for the sealing substrate 604 include plastic substrates made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, acrylic, etc.

[0242] Although not shown in Fig. 2, a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. The protective film may be formed so as to cover the exposed portion of the sealant 605. The protective film may be provided so as to cover the surfaces and side surfaces of the pair of substrates, the exposed side surfaces of the sealing layer, the insulating layer, etc.

[0243] The protective film can be made of a material that is difficult for impurities such as water to permeate, and therefore can effectively prevent impurities such as water from diffusing from the outside to the inside.

[0244] The protective film may be made of an oxide, a nitride, a fluoride, a sulfide, a ternary compound, a metal, a polymer, or the like. For example, a material containing aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide, titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide, cerium oxide, scandium oxide, erbium oxide, vanadium oxide, indium oxide, or the like; a material containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, gallium nitride, or the like; a nitride containing titanium and aluminum; an oxide containing titanium and aluminum; an oxide containing aluminum and zinc; a sulfide containing manganese and zinc; a sulfide containing cerium and strontium; an oxide containing erbium and aluminum; an oxide containing yttrium and zirconium, or the like.

[0245] The protective film is preferably formed using a film formation method with good step coverage. One such method is the atomic layer deposition (ALD) method. It is preferable to use a material that can be formed using the ALD method for the protective film. By using the ALD method, it is possible to form a dense protective film with reduced defects such as cracks and pinholes, or with a uniform thickness. In addition, it is possible to reduce damage to the processed member when forming the protective film.

[0246] For example, by forming a protective film using the ALD method, it is possible to form a uniform protective film with few defects on surfaces with complex uneven shapes, as well as on the top, side, and back surfaces of a touch panel.

[0247] In the above manner, a light-emitting device manufactured using the light-emitting element described in Embodiment 1 can be obtained.

[0248] The light-emitting device in this embodiment uses the light-emitting element described in Embodiment 1, and therefore a light-emitting device with good characteristics can be obtained. Specifically, the light-emitting element described in Embodiment 1 has a long lifetime, and therefore a light-emitting device with good reliability can be obtained. In addition, the light-emitting device using the light-emitting element described in Embodiment 1 has good emission efficiency, and therefore a light-emitting device with low power consumption can be obtained.

[0249] 3 shows an example of a light-emitting device in which a light-emitting element that emits white light is formed and a colored layer (color filter) is provided to achieve full color. In FIG. 3(A), a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, and 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driver circuit portion 1041, first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting element, a sealing substrate 1031, a sealant 1032, and the like are illustrated.

[0250] In FIG. 3A, the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) are provided on a transparent base material 1033. A black matrix 1035 may be further provided. The transparent base material 1033 on which the colored layers and black matrix are provided is aligned and fixed to the substrate 1001. The colored layers and black matrix 1035 are covered with an overcoat layer 1036. In FIG. 3A, there are light-emitting layers from which light does not pass through the colored layers and goes out, and light-emitting layers from which light passes through the colored layers of each color and goes out. The light that does not pass through the colored layers is white, and the light that passes through the colored layers is red, green, and blue, so that an image can be expressed by four color pixels.

[0251] 3B shows an example in which colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. In this manner, the colored layers may be provided between the substrate 1001 and the sealing substrate 1031.

[0252] In the light-emitting device described above, the light-emitting device has a structure (bottom emission type) in which light is extracted on the substrate 1001 side on which the FET is formed, but the light-emitting device may have a structure (top emission type) in which light is extracted on the sealing substrate 1031 side. A cross-sectional view of a top emission type light-emitting device is shown in FIG. 4. In this case, a substrate that does not transmit light can be used as the substrate 1001. The process is performed in the same manner as the bottom emission type light-emitting device until a connection electrode that connects the FET and the anode of the light-emitting element is formed. Thereafter, a third interlayer insulating film 1037 is formed to cover the electrode 1022. This insulating film may play a role of planarization. The third interlayer insulating film 1037 can be formed using the same material as the second interlayer insulating film, or other known materials.

[0253] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are anodes here, but may be cathodes. In addition, in the case of a top-emission type light-emitting device as shown in FIG. 4, it is preferable that the first electrodes are reflective electrodes. The EL layer 1028 has the same structure as that of the EL layer 103 described in the first embodiment, and has an element structure that can emit white light.

[0254] In the top emission structure as shown in FIG. 4, sealing can be performed with a sealing substrate 1031 provided with colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B). A black matrix 1035 may be provided on the sealing substrate 1031 so as to be located between pixels. The colored layers (the red colored layer 1034R, the green colored layer 1034G, and the blue colored layer 1034B) and the black matrix may be covered with an overcoat layer 1036. Note that a substrate having light transmissivity is used as the sealing substrate 1031. In addition, although an example of full color display using four colors, red, green, blue, and white, is shown here, the present invention is not particularly limited, and full color display using four colors, red, yellow, green, and blue, or three colors, red, green, and blue, may be used.

[0255] In a top-emission type light-emitting device, a microcavity structure can be suitably applied. A light-emitting element having a microcavity structure is obtained by making the first electrode a reflective electrode and the second electrode a semi-transmissive / semi-reflective electrode. At least an EL layer is provided between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least a light-emitting layer that becomes a light-emitting region is provided.

[0256] The reflectance of the reflective electrode to visible light is 40% to 100%, preferably 70% to 100%, and the resistivity is 1×10 -2 The semi-transmitting and semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1×10 -2 It is assumed that the film has a resistance of less than Ωcm.

[0257] Light emitted from a light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transmissive and semi-reflective electrode, causing resonance.

[0258] In this light-emitting device, the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode can be changed by changing the thickness of the transparent conductive film, the above-mentioned composite material, the carrier transport material, etc. This makes it possible to intensify the light of a resonating wavelength between the reflective electrode and the semi-transmissive / semi-reflective electrode and attenuate the light of a non-resonating wavelength.

[0259] In addition, since the light reflected by the reflective electrode and returned (first reflected light) causes significant interference with the light (first incident light) that is directly incident on the semi-transmissive and semi-reflective electrode from the light-emitting layer, it is preferable to adjust the optical distance between the reflective electrode and the light-emitting layer to (2n-1)λ / 4 (where n is a natural number equal to or greater than 1, and λ is the wavelength of the emitted light to be amplified). By adjusting the optical distance, the phase of the first reflected light and the first incident light can be aligned, thereby further amplifying the light emitted from the light-emitting layer.

[0260] In the above configuration, the EL layer may have a plurality of light-emitting layers or a single light-emitting layer. For example, the EL layer may be combined with the above-mentioned tandem-type light-emitting element configuration to provide a single light-emitting element with a plurality of EL layers sandwiched between a charge generating layer, and each EL layer may have a single or multiple light-emitting layers.

[0261] The microcavity structure makes it possible to increase the emission intensity of a specific wavelength in the front direction, thereby reducing power consumption. In the case of a light-emitting device that displays images using four sub-pixels of red, yellow, green, and blue, in addition to the brightness improvement effect of yellow emission, the microcavity structure that matches the wavelength of each color can be applied to all sub-pixels, resulting in a light-emitting device with good characteristics.

[0262] The light-emitting device in this embodiment uses the light-emitting element described in Embodiment 1, and therefore a light-emitting device with good characteristics can be obtained. Specifically, the light-emitting element described in Embodiment 1 has a long lifetime, and therefore a light-emitting device with good reliability can be obtained. In addition, the light-emitting device using the light-emitting element described in Embodiment 1 has good emission efficiency, and therefore a light-emitting device with low power consumption can be obtained.

[0263] Up to this point, active matrix type light emitting devices have been described, but from here on, passive matrix type light emitting devices will be described. FIG. 5 shows a passive matrix type light emitting device manufactured by applying the present invention. FIG. 5(A) is a perspective view showing the light emitting device, and FIG. 5(B) is a cross-sectional view taken along XY in FIG. 5(A). In FIG. 5, an EL layer 955 is provided between an electrode 952 and an electrode 956 on a substrate 951. An end of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided on the insulating layer 953. The sidewalls of the partition layer 954 have an inclination such that the distance between one sidewall and the other sidewall becomes narrower as the sidewall approaches the substrate surface. That is, the cross section of the partition layer 954 in the short side direction is trapezoidal, and the bottom side (the side facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is shorter than the top side (the side facing the same direction as the surface direction of the insulating layer 953 and not in contact with the insulating layer 953). By providing the partition layer 954 in this manner, defects in the light-emitting element due to static electricity or the like can be prevented. In addition, the light-emitting element described in Embodiment 1 is used in a passive matrix light-emitting device, and the light-emitting device can be made to have high reliability or low power consumption.

[0264] The light-emitting device described above is capable of controlling each of a large number of minute light-emitting elements arranged in a matrix, and therefore can be suitably used as a display device for displaying images.

[0265] This embodiment mode can be freely combined with other embodiment modes.

[0266] (Embodiment 4) In this embodiment, an example in which the light-emitting element described in Embodiment 1 is used as a lighting device will be described with reference to Fig. 6. Fig. 6(B) is a top view of the lighting device, and Fig. 6(A) is a cross-sectional view taken along line ef in Fig. 6(B).

[0267] In the lighting device in this embodiment, a first electrode 401 is formed over a light-transmitting substrate 400, which is a support. The first electrode 401 corresponds to the first electrode 101 in Embodiment 1. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.

[0268] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0269] An EL layer 403 is formed over the first electrode 401. The EL layer 403 corresponds to the structure of the EL layer 103 in Embodiment 1, or a structure in which the light-emitting units 511 and 512 and the charge generation layer 513 are combined, or the like. For these structures, refer to the description thereof.

[0270] A second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in Embodiment 1. When light is extracted from the first electrode 401 side, the second electrode 404 is formed of a material with high reflectivity. The second electrode 404 is connected to a pad 412 to supply a voltage.

[0271] As described above, the lighting device described in this embodiment has a light-emitting element having the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting element has high emission efficiency, the lighting device in this embodiment can have low power consumption.

[0272] The substrate 400 on which the light-emitting element having the above structure is formed and a sealing substrate 407 are fixed and sealed using sealants 405 and 406, thereby completing the lighting device. Either one of the sealants 405 and 406 may be used. A desiccant may be mixed into the inner sealant 406 (not shown in FIG. 6(B)), which can adsorb moisture and improve reliability.

[0273] Moreover, the pad 412 and a part of the first electrode 401 can be extended outside the sealing materials 405 and 406 to serve as an external input terminal. Also, an IC chip 420 equipped with a converter or the like may be provided thereon.

[0274] As described above, the lighting device described in this embodiment uses the light-emitting element described in Embodiment 2 as an EL element, and can be a light-emitting device with high reliability and low power consumption.

[0275] (Embodiment 5) In this embodiment, an example of an electronic device including a light-emitting element described in Embodiment 1 will be described. The light-emitting element described in Embodiment 2 has a long lifetime and is a highly reliable light-emitting element. As a result, the electronic device described in this embodiment can be an electronic device having a highly reliable light-emitting portion.

[0276] Examples of electronic devices to which the light-emitting elements are applied include television devices (also called televisions or television receivers), monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), portable game machines, personal digital assistants, audio playback devices, large game machines such as pachinko machines, etc. Specific examples of these electronic devices are shown below.

[0277] 7A illustrates an example of a television set. In the television set, a display portion 7103 is incorporated in a housing 7101. Here, the housing 7101 is supported by a stand 7105. The display portion 7103 can display an image, and the light-emitting elements described in Embodiment 1 are arranged in a matrix.

[0278] The television device can be operated using an operation switch provided on the housing 7101 or a separate remote control 7110. Using operation keys 7109 provided on the remote control 7110, the channel and volume can be controlled, and an image displayed on the display portion 7103 can be operated. The remote control 7110 may be provided with a display portion 7107 that displays information output from the remote control 7110.

[0279] The television device is configured to include a receiver, a modem, etc. The receiver can receive general television broadcasts, and by connecting to a wired or wireless communication network via the modem, it is also possible to perform one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.

[0280] FIG. 7B1 shows a computer, which includes a main body 7201, a housing 7202, a display portion 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like. Note that this computer is manufactured by using the light-emitting elements described in Embodiment 1 arranged in a matrix for the display portion 7203. The computer in FIG. 7B1 may have a form as shown in FIG. 7B2. The computer in FIG. 7B2 is provided with a second display portion 7210 instead of the keyboard 7204 and the pointing device 7206. The second display portion 7210 is a touch panel type, and input can be performed by operating a display for input displayed on the second display portion 7210 with a finger or a dedicated pen. The second display portion 7210 can display not only a display for input but also other images. The display portion 7203 may also be a touch panel. The two screens are connected by a hinge, which can prevent the screens from being scratched or broken during storage or transportation.

[0281] 7C shows an example of a mobile terminal. A mobile phone 7400 includes a display portion 7402 incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. Note that the mobile phone 7400 includes the display portion 7402 in which the light-emitting elements described in Embodiment 1 are arranged in a matrix.

[0282] 7C can be configured so that information can be input by touching the display portion 7402 with a finger or the like. In this case, operations such as making a call or composing an e-mail can be performed by touching the display portion 7402 with a finger or the like.

[0283] The screen of the display unit 7402 has three main modes. The first is a display mode that is mainly for displaying images, the second is an input mode that is mainly for inputting information such as characters, and the third is a display + input mode that combines the display mode and the input mode.

[0284] For example, when making a call or composing an e-mail, the display portion 7402 may be set to a character input mode mainly for inputting characters, and the character input operation may be performed by inputting characters displayed on the screen. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402.

[0285] In addition, by providing a detection device having a sensor for detecting tilt, such as a gyro or an acceleration sensor, inside the mobile terminal, the orientation of the mobile terminal (portrait or landscape) can be determined and the screen display of the display portion 7402 can be automatically switched.

[0286] The screen mode can be switched by touching the display portion 7402 or by operating operation buttons 7403 on the housing 7401. The mode can also be switched depending on the type of image displayed on the display portion 7402. For example, if the image signal to be displayed on the display portion is moving image data, the mode is switched to the display mode, and if it is text data, the mode is switched to the input mode.

[0287] In addition, in the input mode, a signal detected by an optical sensor of the display portion 7402 may be detected, and if there is no input by a touch operation on the display portion 7402 for a certain period of time, the screen mode may be controlled to be switched from the input mode to the display mode.

[0288] The display portion 7402 can also function as an image sensor. For example, personal authentication can be performed by touching the display portion 7402 with a palm or a finger to capture an image of a palm print, a fingerprint, or the like. In addition, finger veins, palm veins, or the like can be captured by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light for the display portion.

[0289] Note that the structure described in this embodiment mode can be used by appropriately combining the structures described in any of Embodiment Modes 1 to 4.

[0290] As described above, the light-emitting device including the light-emitting element described in Embodiment 1 has a very wide range of application, and can be applied to electronic devices in a variety of fields. By using the light-emitting element described in Embodiment 1, electronic devices with high reliability can be obtained.

[0291] FIG. 8(A) is a schematic diagram showing an example of a cleaning robot.

[0292] The cleaning robot 5100 has a display 5101 arranged on the top surface, a plurality of cameras 5102 arranged on the side surface, a brush 5103, and an operation button 5104. Although not shown, the bottom surface of the cleaning robot 5100 is provided with tires, a suction port, and the like. The cleaning robot 5100 also has various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezoelectric sensor, an optical sensor, and a gyro sensor. The cleaning robot 5100 also has wireless communication means.

[0293] The cleaning robot 5100 can move by itself, detect dirt 5120, and suck up the dirt from a suction port provided on the bottom surface.

[0294] In addition, the cleaning robot 5100 can analyze the image captured by the camera 5102 and determine the presence or absence of obstacles such as walls, furniture, steps, etc. Furthermore, when an object that may become entangled in the brush 5103, such as a wire, is detected by image analysis, the rotation of the brush 5103 can be stopped.

[0295] The remaining battery level, the amount of sucked up dirt, etc. can be displayed on the display 5101. The route traveled by the cleaning robot 5100 may be displayed on the display 5101. The display 5101 may be a touch panel, and an operation button 5104 may be provided on the display 5101.

[0296] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. Images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can know the state of the room even when he or she is away from home. Also, the display on the display 5101 can be confirmed on a portable electronic device such as a smartphone.

[0297] The light-emitting device according to one embodiment of the present invention can be used for the display 5101 .

[0298] The robot 2100 shown in FIG. 8(B) includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0299] The microphone 2102 has a function of detecting the user's voice, environmental sounds, etc. The speaker 2104 has a function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104.

[0300] The display 2105 has a function of displaying various information. The robot 2100 can display information desired by the user on the display 2105. The display 2105 may be equipped with a touch panel. The display 2105 may also be a removable information terminal, and by installing it in a fixed position on the robot 2100, charging and data transfer are possible.

[0301] The upper camera 2103 and the lower camera 2106 have a function of capturing images of the surroundings of the robot 2100. In addition, the obstacle sensor 2107 can detect the presence or absence of an obstacle in the moving direction when the robot 2100 moves forward using the moving mechanism 2108. The robot 2100 can recognize the surrounding environment and move safely using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107. The light-emitting device of one embodiment of the present invention can be used for the display 2105.

[0302] 8C is a diagram showing an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, operation keys 5005 (including a power switch or an operation switch), a connection terminal 5006, a sensor 5007 (including a function of measuring force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared ray), a microphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, and the like.

[0303] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the second display portion 5002 .

[0304] 9 shows an example in which the light-emitting element described in Embodiment 1 is used in a desk lamp, which is a lighting device. The desk lamp shown in FIG. 9 includes a housing 2001 and a light source 2002, and the lighting device described in Embodiment 3 may be used as the light source 2002.

[0305] FIG. 10 shows an example in which the light-emitting element described in Embodiment 1 is used as an indoor lighting device 3001. The light-emitting element described in Embodiment 1 is a highly reliable light-emitting element, and therefore a highly reliable lighting device can be provided. The light-emitting element described in Embodiment 2 can be made large in area and therefore can be used as a large-area lighting device. The light-emitting element described in Embodiment 1 is thin and therefore can be used as a thin lighting device.

[0306] The light-emitting element described in Embodiment 2 can also be mounted on a windshield or dashboard of an automobile. FIG 11 shows one mode in which the light-emitting element described in Embodiment 2 is used on a windshield or dashboard of an automobile. Display regions 5200 to 5203 are displays provided using the light-emitting element described in Embodiment 2.

[0307] A display region 5200 and a display region 5201 are a display device equipped with the light-emitting element described in Embodiment 1, which is provided on the windshield of an automobile. The light-emitting element described in Embodiment 2 can be a so-called see-through display device in which the other side can be seen through by forming the first electrode and the second electrode using light-transmitting electrodes. If the display is in a see-through state, the display device can be installed on the windshield of an automobile without interfering with the view. When a transistor for driving is provided, a light-transmitting transistor such as an organic transistor made of an organic semiconductor material or a transistor using an oxide semiconductor is preferably used.

[0308] The display area 5202 is a display device provided in a pillar portion and equipped with the light-emitting element described in Embodiment 1. By displaying an image from an imaging means provided in the vehicle body in the display area 5202, the view blocked by the pillar can be complemented. Similarly, the display area 5203 provided in the dashboard portion can complement the view blocked by the vehicle body by displaying an image from an imaging means provided outside the vehicle, thereby compensating for blind spots and improving safety. By displaying an image to complement the invisible parts, safety can be confirmed more naturally and without discomfort.

[0309] The display area 5203 can also provide various other information such as navigation information, a speedometer, a tachometer, mileage, fuel, gear status, and air conditioning settings. The display items and layout can be changed as appropriate to suit the user's preferences. Note that this information can also be provided in the display areas 5200 to 5202. The display areas 5200 to 5203 can also be used as lighting devices.

[0310] 12A and 12B show a foldable mobile information terminal 5150. The foldable mobile information terminal 5150 has a housing 5151, a display area 5152, and a bending portion 5153. Fig. 12A shows the mobile information terminal 5150 in an unfolded state. Fig. 12B shows the mobile information terminal in a folded state. Although the mobile information terminal 5150 has a large display area 5152, it is compact and highly portable when folded.

[0311] The display area 5152 can be folded in half by the bending portion 5153. The bending portion 5153 is composed of an expandable member and a plurality of support members, and when folding, the expandable member stretches. The bending portion 5153 is folded with a curvature radius of 2 mm or more, preferably 3 mm or more.

[0312] Note that the display region 5152 may be a touch panel (input / output device) equipped with a touch sensor (input device). The light-emitting device of one embodiment of the present invention can be used for the display region 5152.

[0313] 13(A) to 13(C) show a foldable portable information terminal 9310. Fig. 13(A) shows the portable information terminal 9310 in an unfolded state. Fig. 13(B) shows the portable information terminal 9310 in a state in which it is changing from one of the unfolded state and the folded state to the other. Fig. 13(C) shows the portable information terminal 9310 in a folded state. The portable information terminal 9310 has excellent portability in the folded state, and has excellent viewability of the display due to a seamless wide display area in the unfolded state.

[0314] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. Note that the display panel 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). The display panel 9311 can be reversibly transformed from an unfolded state of the mobile information terminal 9310 to a folded state by bending the two housings 9315 via the hinges 9313. The light-emitting device of one embodiment of the present invention can be used for the display panel 9311. EXAMPLES

[0315] In this example, a synthesis method of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviation: BBABnf(II)(2)), which is an organic compound according to one embodiment of the present invention, is described in detail. The structural formula of BBABnf(II)(2) is shown below.

[0316] [ka]

[0317] <Step 1: Synthesis of 3-(5-chloro-2-fluorophenyl)-2-naphthol> In a 300mL three-neck flask, 8.9g (40mmol) of 3-bromo-2-naphthol, 10g (60mmol) of 5-chloro-2-fluorophenylboronic acid, 0.24g (0.080mmol) of tri(ortho-tolyl)phosphine, 40mL of potassium carbonate aqueous solution (2.0mmol / L), 120mL of toluene, and 50mL of ethanol were added and mixed. After degassing the mixture under reduced pressure, the flask was substituted with nitrogen. The mixture was heated to 60°C, and then 90mg (40μmol) of palladium(II) acetate was added and stirred at 80°C for 8 hours. After stirring, 5.8g (35mmol) of 5-chloro-2-fluorophenylboronic acid and 90mg (40μmol) of palladium(II) acetate were added to the mixture and stirred at 80°C for 8 hours. After stirring, the mixture was cooled to room temperature, washed with water and saturated saline, and the aqueous and organic layers were separated. The organic layer was then dried over magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated and dried. After drying, 7.6 g of a black solid was obtained. The synthesis scheme of step 1 is shown below.

[0318] [ka]

[0319] <Step 2: Synthesis of 2-chlorobenzo[b]naphtho[2,3-d]furan> In a 500 mL eggplant flask, 7.6 g of the black solid obtained in step 1, 7.6 g (55 mmol) of potassium carbonate, and 110 mL of N-methyl-2-pyrrolidone (abbreviation: NMP) were placed and stirred at 120 °C for 7 hours. The resulting mixture was suction filtered to remove the potassium carbonate. When 10 mL of 2 mol / L hydrochloric acid was added to the obtained filtrate to neutralize the filtrate, a white precipitate was formed. This white precipitate was collected by suction filtration and washed with ethyl acetate, water, and ethanol, and 3.5 g of a white solid was obtained, with a combined yield of 34% for steps 1 and 2. The synthesis scheme for step 2 is shown below.

[0320] [ka]

[0321] The obtained solid 1 The H NMR data are shown in Figures 14(A) and (B), and the numerical data are shown below. Note that Figure 14(B) is an enlarged view of the range from 7.2 ppm to 8.3 ppm in Figure 14(A). This shows that 2-chlorobenzo[b]naphtho[2,3-d]furan was obtained.

[0322] 1 H NMR (chloroform-d, 500MHz): δ = 8.39 (s, 1H), 8.04-8.03 (m, 2H), 7.97 (d, J = 8.0Hz, 1H), 7.92 (s, 1H), 7.54 (t, J = 7.5Hz, 1H), 7.52-7.45 (m, 3H)

[0323] <Step 3: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (BBABnf(II)(2))> In a 300 mL three-neck flask equipped with a reflux condenser, 2.0 g (8.0 mmol) of 2-chlorobenzo[b]naphtho[2,3-d]furan, 2.6 g (8.0 mmol) of bis(4-biphenylyl)amine, 56 mg (0.16 mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (trade name: cBRIDP (registered trademark)), 1.5 g (16 mmol) of sodium tert-butoxide, and 100 mL of toluene were placed, and the mixture was degassed under reduced pressure, the atmosphere in the flask was replaced with nitrogen, and then 46 mg (80 μmol) of bis(benzylideneacetone)palladium was added. This mixture was stirred at 110° C. for 13 hours. After stirring, water was added to the obtained mixture, the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined, washed with water and saturated saline, and dried with magnesium sulfate. The mixture was filtered and the filtrate was concentrated to give 3.7 g of a brown solid in 86% yield. The synthetic scheme of Step 3 is shown below.

[0324] [ka]

[0325] The obtained solid 1 The H NMR data are shown in Figures 15(A) and (B), and the numerical data are shown below. Note that Figure 15(B) is an enlarged view of the range from 7.0 ppm to 8.1 ppm in Figure 15(A). This shows that BBABnf(II)(2), an organic compound according to one embodiment of the present invention, was obtained in this synthesis example.

[0326] 1 H NMR (chloroform-d, 500MHz): δ=8.33(s,1H),7.96(d,J=10Hz,2H),7.92-7.91(m,2H),7. 60(d,J=7.0Hz,4H),7.53-7.38(m,12H),7.32(t,J=7.5Hz,2H),7.24(d,J=7.0Hz,4H)

[0327] The obtained solid was purified by sublimation purification. The sublimation purification was performed by heating the solid to 275°C under the conditions of an argon flow rate of 15 mL / min and a pressure of 2.6 Pa. After the sublimation purification, the target compound was obtained as a yellow solid in a yield of 2.6 g and a recovery rate of 70%.

[0328] Next, the absorption spectrum and emission spectrum of the toluene solution of BBABnf(II)(2) were measured, and the results are shown in Figure 16. The absorption spectrum and emission spectrum of the thin film are shown in Figure 17. The solid thin film was prepared by vacuum deposition on a quartz substrate. The absorption spectrum of the toluene solution was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation), and the spectrum measured by putting only toluene in a quartz cell was subtracted. The absorption spectrum of the thin film was measured using a spectrophotometer (U4100 spectrophotometer, manufactured by Hitachi High-Technologies Corporation). The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics Corporation).

[0329] As shown in Figure 16, the toluene solution of BBABnf(II)(2) showed absorption peaks at 402 nm, 346 nm, and 322 nm, and the emission wavelength peak was 435 nm (excitation wavelength 385 nm). Also, as shown in Figure 17, the thin film of BBABnf(II)(2) showed absorption peaks at 392 nm, 350 nm, 257 nm, and 207 nm, and the emission wavelength peak was 452 nm (excitation wavelength 350 nm). From these results, it was confirmed that BBABnf(II)(2)B emits blue light, and it was found that it can be used as a host for luminescent substances and fluorescent substances in the visible range.

[0330] In addition, it was found that the thin film of BBABnf(II)(2) did not easily aggregate even in air, had little change in morphology, and had good film quality.

[0331] Next, the HOMO and LUMO levels of BBABnf(II)(2) were calculated based on cyclic voltammetry (CV) measurements. The calculation method is shown below.

[0332] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C). The solution used for CV measurement was prepared by dissolving the supporting electrolyte tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) in dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) to a concentration of 100 mmol / L, and further dissolving the measurement target to a concentration of 2 mmol / L. A platinum electrode (PTE platinum electrode, BAS Co., Ltd.) was used as the working electrode, a platinum electrode (Pt counter electrode (5 cm) for VC-3, BAS Co., Ltd.) was used as the auxiliary electrode, and an Ag / Ag+ electrode (RE7 non-aqueous solvent reference electrode, BAS Co., Ltd.) was used as the reference electrode. The measurements were performed at room temperature (20-25°C). The scan rate during CV measurements was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] relative to the reference electrode were measured. Ea was the midpoint potential of the oxidation-reduction wave, and Ec was the midpoint potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this example with respect to the vacuum level is known to be -4.94 [eV], the HOMO level and LUMO level can be calculated from the formulas HOMO level [eV] = -4.94-Ea and LUMO level [eV] = -4.94-Ec, respectively.

[0333] The CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was compared with the oxidation-reduction wave in the first cycle to examine the electrical stability of the compound.

[0334] As a result, the HOMO level of BBABnf(II)(2) was found to be -5.45 eV and the LUMO level to be -2.50 eV. In addition, when the waveforms after the 1st and 100th cycles of repeated measurements of the oxidation-reduction wave were compared, 89% of the peak intensity was maintained in the oxidation potential Ea [V] measurement, confirming that BBABnf(II)(2) has very good resistance to oxidation.

[0335] Differential scanning calorimetry (DSC) of BBABnf(II)(2) was measured using a Pyris1 DSC manufactured by PerkinElmer. Differential scanning calorimetry was performed by heating from -10°C to 310°C at a heating rate of 40°C / min, holding at the same temperature for 1 minute, then cooling to -10°C at a heating rate of 100°C / min, and holding at -10°C for 5 minutes, twice in succession. The results of the second cycle of DSC measurement revealed that the glass transition point of BBABnf(II)(2) was 106°C, indicating that it is a substance with extremely high heat resistance.

[0336] Thermogravimetry-Differential Thermal Analysis (TG-DTA) of BBABnf(II)(2) was also performed. A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS) was used for the measurements. The measurements were performed at atmospheric pressure, with a heating rate of 10°C / min, and under a nitrogen gas flow (flow rate of 200 mL / min). Thermogravimetry-Differential Thermal Analysis revealed that the temperature at which the weight of BBABnf(II)(2) was -5% of the weight at the start of the measurement (decomposition temperature) was 440°C or higher, indicating that BBABnf(II)(2) is a highly heat-resistant substance. EXAMPLES

[0337] In this example, a synthesis method of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), which is an organic compound according to one embodiment of the present invention, is described in detail. The structural formula of BBABnf(II)(4) is shown below.

[0338] [ka]

[0339] <Step 1: Synthesis of 3-(3-chloro-2-fluorophenyl)-2-naphthol> In a 300mL three-neck flask, 7.5g (34mmol) of 3-bromo-2-naphthol, 5.9g (34mmol) of 3-chloro-2-fluorophenylboronic acid, 0.21g (67μmol) of tri(ortho-tolyl)phosphine, 30mL of potassium carbonate aqueous solution (2.0mol / L), 110mL of toluene, and 30mL of ethanol were added, and the mixture was degassed under reduced pressure, and then the flask was replaced with nitrogen. After heating this mixture to 60℃, 76mg (34μmol) of palladium(II) acetate was added and stirred at 80℃ for 8 hours. After stirring, 3.0g (17mmol) of 3-chloro-2-fluorophenylboronic acid and 36mg (16μmol) of palladium(II) acetate were added and stirred at 80℃ for 8 hours. After stirring, the mixture was cooled to room temperature, washed with water and saturated saline, and the aqueous and organic layers were separated. The organic layer was then dried over magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated and dried. After drying, 6.1 g of a black solid was obtained. The synthesis scheme of step 1 is shown below.

[0340] [ka]

[0341] <Step 2: Synthesis of 4-chlorobenzo[b]naphtho[2,3-d]furan> In a 500 mL eggplant flask, 6.1 g of the black solid obtained in step 1, 6.3 g (44 mmol) of potassium carbonate, and 110 mL of N-methyl-2-pyrrolidone (NMP) were placed and stirred at 120 ° C for 7 hours. The resulting mixture was suction filtered to remove potassium carbonate. The resulting filtrate was neutralized by adding 10 mL of 2.0 mol / L hydrochloric acid. Water was added to this mixture, the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with ethyl acetate. The resulting extract and organic layer were combined, washed with water, a saturated aqueous sodium bicarbonate solution, and saturated saline, and dried with magnesium sulfate. The mixture was naturally filtered, and the filtrate was concentrated to obtain 4.9 g of a brown solid. The brown solid was purified by supercritical fluid chromatography (SFC) (mobile phase: liquid carbon dioxide: tetrahydrofuran = 7:3), and 2.2 g of the target pale yellow solid was obtained, with a combined yield of 26% for steps 1 and 2. The synthesis scheme for step 2 is shown below.

[0342] [ka] The obtained solid 1 The H NMR data is shown in Figures 18(A) and (B), and the numerical data is shown below. Note that Figure 18(B) is an enlarged view of the range from 7.2 ppm to 8.3 ppm in Figure 18(A). This shows that 4-chlorobenzo[b]naphtho[2,3-d]furan was obtained.

[0343] 1 H NMR (chloroform-d, 500MHz): δ = 8.42 (s, 1H), 8.04 (d, J = 8.5Hz, 1H), 8.00-7.96 (m, 3H), 7.57-7.49 (m, 3H), 7.32 (t, J = 7.5Hz, 1H)

[0344] <Step 3: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (BBABnf(II)(4))> In a 300mL three-neck flask equipped with a reflux condenser, 1.5g (6.0mmol) of 4-chlorobenzo[b]naphtho[2,3-d]furan, 1.9g (6.0mmol) of bis(4-biphenylyl)amine, 42mg (0.12mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (cBRIDP (registered trademark)), 1.2g (12mmol) of sodium tert-butoxide, and 90mL of toluene were placed, and the flask was purged with nitrogen after degassing under reduced pressure. 34mg (60μmol) of bis(benzylideneacetone)palladium was added to this mixture, and the mixture was stirred at 110°C for 6 hours. Water was added to the resulting mixture, and the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with toluene. The resulting extract and the organic layer were combined, washed with water and saturated saline, and dried with magnesium sulfate. This mixture was gravity filtered, and the obtained filtrate was concentrated to give 2.7 g of a brown solid, which was the target product, in a yield of 83%. The synthetic scheme for step 3 is shown below.

[0345] [ka]

[0346] The obtained solid 1 The H NMR data are shown in Figures 19(A) and (B), and the numerical data are shown below. Note that Figure 19(B) is an enlarged view of the range from 7.0 ppm to 8.6 ppm in Figure 19(A). This shows that BBABnf(II)(4), an organic compound according to one embodiment of the present invention, was obtained in this synthesis example.

[0347] 1 H NMR (chloroform-d, 500MHz): δ=8.42(s,1H),8.03(d,J=10Hz,1H),7.91-7.87(m,2H),7.77(s,1H),7.60(d,J=8.0Hz,4H),7.53 (d,J=8.0Hz,4H),7.50-7.45(m,2H),7.42(t,J=7.5Hz,4H),7.38-7.34(m,2H),7.31(t,J=7.5Hz,2H),7.23(d,J=8.5Hz,4H)

[0348] The obtained solid was purified by sublimation purification. The sublimation purification was performed by heating the solid to 250°C under the conditions of an argon flow rate of 15 mL / min and a pressure of 3.7 Pa. After the sublimation purification, the target compound was obtained as a yellow solid (yield 450 mg, recovery rate 17%).

[0349] Next, the absorption spectrum and emission spectrum of a toluene solution of BBABnf(II)(4) were measured, and the results are shown in Figure 20. The absorption spectrum and emission spectrum of the thin film are shown in Figure 21. The measurements were performed in the same manner as in Example 1.

[0350] As shown in Figure 20, the toluene solution of BBABnf(II)(4) showed absorption peaks at 384 nm, 345 nm, and 327 nm, and the emission wavelength peak was 421 nm (excitation wavelength 327 nm). Also, as shown in Figure 21, the thin film of BBABnf(II)(4) showed absorption peaks at 374 nm, 355 nm, 325 nm, 257 nm, and 207 nm, and the emission wavelength peak was 439 nm (excitation wavelength 350 nm). From these results, it was confirmed that BBABnf(II)(4)B emits blue light, and it was found that it can be used as a host for luminescent substances and fluorescent substances in the visible range.

[0351] In addition, it was found that the thin film of BBABnf(II)(4) did not easily aggregate even in air, had little change in morphology, and had good film quality.

[0352] Next, the HOMO level and LUMO level of BBABnf(II)(4) were calculated based on cyclic voltammetry (CV) measurements. The calculation method was the same as in Example 1.

[0353] The CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was compared with the oxidation-reduction wave in the first cycle to examine the electrical stability of the compound.

[0354] As a result, the HOMO level of BBABnf(II)(4) was found to be -5.57 eV and the LUMO level to be -2.48 eV. In addition, when the waveforms of the 1st and 100th cycles were compared in repeated measurements of the oxidation-reduction wave, 85% of the peak intensity was maintained in the oxidation potential Ea [V] measurement, confirming that BBABnf(II)(4) has very good resistance to oxidation.

[0355] Differential scanning calorimetry of BBABnf(II)(4) was also carried out using the same apparatus as in Example 1. The differential scanning calorimetry was carried out by heating the sample from -10°C to 275°C at a heating rate of 40°C / min, holding the sample at the same temperature for 1 minute, then cooling the sample to -10°C at a heating rate of 100°C / min, and holding the sample at -10°C for 5 minutes, twice in succession. The results of the second cycle of DSC measurement revealed that the glass transition point of BBABnf(II)(4) was 108°C, indicating that the sample was a substance with extremely high heat resistance.

[0356] In addition, thermogravimetry-differential thermal analysis of BBABnf(II)(4) was performed in the same manner as in Example 1. In the thermogravimetry-differential thermal analysis, it was found that the temperature at which the weight determined by thermogravimetry of BBABnf(II)(4) was -5% of the weight at the start of the measurement (decomposition temperature) was 410°C, indicating that BBABnf(II)(4) is a substance with high heat resistance. EXAMPLES

[0357] Example 1 In this example, a synthesis method of N,N-bis(4-biphenyl)benzo[b]naphtho[2,1-d]furan-4-amine (abbreviation: BBAaBnf(10)), which is an organic compound according to one embodiment of the present invention, is described in detail. The structural formula of BBAaBnf(10) is shown below.

[0358] [ka]

[0359] <Step 1: Synthesis of 2-bromophenyl-1-naphthyl ether> In a 200mL three-neck flask, 2.9g (20mmol) of 1-naphthol and 13g (40mmol) of potassium carbonate were added, and the atmosphere in the flask was replaced with nitrogen. To this mixture, 110mL of N-methylpyrrolidone (NMP) and 7.5g (40mmol) of 1-bromo-2-fluorobenzene were added, and the mixture was stirred at 170°C for 4 hours. After stirring, 100mL of 2mol / L hydrochloric acid was added to the resulting mixture and stirred at room temperature. After stirring, the organic layer of this mixture was washed twice with 100mL of 2mol / L hydrochloric acid, and the aqueous layer was extracted twice with toluene. The extracted solution and the organic layer were combined and washed with 100mL of 2mol / L hydrochloric acid and saturated saline, and magnesium sulfate was added to the resulting organic layer to dry it. This mixture was naturally filtered, and the resulting filtrate was concentrated to obtain a brown compound. This compound was purified by silica gel column chromatography (developing solvent: toluene:hexane=1:1) to obtain 4.1 g of the target colorless transparent oil in a yield of 69%. The synthesis scheme of step 1 is shown below.

[0360] [ka]

[0361] <Step 2: Synthesis of benzo[b]naphtho[2,1-d]furan> In a 500 mL eggplant flask, 4.1 g (14 mmol) of 2-bromophenyl-1-naphthyl ether, 0.20 mg (0.40 mmol) of triphenylphosphine, and 10 g (30 mmol) of cesium carbonate were added, and the atmosphere in the flask was replaced with nitrogen. 100 mL of NMP was added to this mixture, and the mixture was degassed under reduced pressure. 89 mg (0.40 mmol) of palladium (II) acetate was added to this mixture, and the mixture was stirred at 180°C for 3.5 hours under a nitrogen stream. After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting extract and organic layer were combined, washed with 2 mol / L hydrochloric acid, saturated aqueous sodium carbonate solution, and saturated saline, and then dried with magnesium sulfate. The mixture was naturally filtered, and the obtained filtrate was concentrated, obtaining 3.0 g of the target light brown solid in a yield of 99%. The synthesis scheme of step 2 is shown below.

[0362] [ka]

[0363] <Step 3: Synthesis of 10-iodobenzo[b]naphtho[2,1-d]furan> 3.0g (14mmol) of benzo[b]naphtho[2,1-d]furan was added to a 200mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen, after which 70mL of tetrahydrofuran (THF) was added. This solution was cooled to -75°C, and then 8.5mL (14mmol) of n-butyllithium (1.64mol / L n-hexane solution) was added dropwise to this solution. After the dropwise addition, the resulting solution was stirred at room temperature for 1 hour. After the stirring, this solution was cooled to -75°C, and then a solution in which 3.6g (14mmol) of iodine was dissolved in 10mL of THF was added dropwise. After the dropwise addition, the resulting solution was stirred for 17 hours while returning to room temperature. After the stirring, an aqueous solution of sodium thiosulfate was added to the resulting solution, and after stirring for 1 hour, the organic layer of this mixture was washed with water, and the aqueous layer was extracted with ethyl acetate. The extract and the organic layer were combined, washed with saturated saline, and the resulting organic layer was dried with magnesium sulfate. After drying, the mixture was gravity filtered and the resulting solution was concentrated to give the desired white solid in an amount of 4.4 g and a yield of 93%. The synthetic scheme of Step 3 is shown below.

[0364] [ka]

[0365] Below is the chloroform solution 1 The results of H NMR measurement are shown below. 1H NMR (chloroform-d, 500MHz): δ=7.16(t,J=7.8Hz,1H),7.59(td,J1=7.5Hz,J2=1.5Hz,1H),7.67(td,J1=7.5Hz,J2=1.0Hz,1H), 7.80(d,J=8.5Hz,1H),7.83(dd,J1=8.0Hz,J2=1.5Hz,1H),7.94-7.96(m,2H),7.99(d,J=8.0Hz,1H),8.53(d,J=8.5Hz,1H)

[0366] <Step 4: Synthesis of N,N-bis(4-biphenyl)benzo[b]naphtho[2,1-d]furan-4-amine (abbreviation: BBAaBnf(10))> In a 200mL three-neck flask equipped with a reflux condenser, 2.0g (6.0mmol) of 10-iodobenzo[b]naphtho[2,1-d]furan, 1.9g (6.0mmol) of bis(4-biphenylyl)amine, 42mg (0.12mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (cBRIDP (registered trademark)), 1.2g (12mmol) of sodium tert-butoxide, and 70mL of toluene were placed, and the mixture was degassed under reduced pressure, and then the atmosphere in the flask was replaced with nitrogen. After adding 34mg (0.060mmol) of bis(benzylideneacetone)palladium, the mixture was stirred at 110°C for 10 hours. After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The organic layer and the obtained extract were washed together with water and saturated saline, and dried over magnesium sulfate. The mixture was gravity filtered, and the obtained filtrate was concentrated. The obtained crude product was purified by silica gel chromatography (mobile phase: hexane:toluene=5:1) to obtain 0.75 g of the target brown solid in a yield of 23%. The synthesis scheme of Step 4 is shown below.

[0367] [ka]

[0368] The obtained solid 1The 1 H NMR data is shown below, which indicates that BBAaBnf (10), an organic compound according to one embodiment of the present invention, was obtained in this synthesis example.

[0369] 1 H NMR (chloroform-d,500MHz): δ=7.99(d,J=8.5Hz,1H),7.93(d,J=7.5Hz,1H),7.90(d,J =8.0Hz,1H),7.81(dd,J=5.0,4.0Hz,1H),7.76(d,J=8.5Hz,1H),7.60(d,J=8.5Hz, 4H),7.54(d,J=8.5Hz,4H),7.49(t,J=6.5Hz,1H),7.81(dd,J=8.0,1.5Hz,1H),7.4 2(t,J=8.0Hz,4H),7.38-7.37(m,2H),7.31(t,J=7.5Hz,2H),7.29(d,J=8.5Hz,4H)

[0370] The obtained solid was purified by sublimation purification. The sublimation purification was performed by heating the solid to 270°C under the conditions of an argon flow rate of 15 mL / min and a pressure of 3.7 Pa. After sublimation purification, the target compound was obtained as a glassy yellow solid in a yield of 0.44 g and a recovery rate of 58%. EXAMPLES

[0371] Example 1 This example describes the light-emitting element 1 and the light-emitting element 2 which are one embodiment of the present invention described in Embodiment 2. The structural formulae of organic compounds used in the light-emitting element 1 and the light-emitting element 2 are shown below.

[0372] [ka]

[0373] (Method of manufacturing light-emitting element 1) First, indium tin oxide containing silicon oxide (ITSO) was formed by sputtering on a glass substrate to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the area of ​​the electrode was 2 mm×2 mm.

[0374] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0375] Then, 10 -4 The substrate was introduced into a vacuum deposition apparatus whose inside had been reduced in pressure to about Pa, and vacuum baking was carried out at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0376] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward. 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) represented by the above structural formula (i) was deposited to a thickness of 5 nm on the first electrode 101 by a deposition method using resistance heating to form a hole injection layer 111.

[0377] Next, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) represented by the above structural formula (ii) was deposited on the hole injection layer 111 to a thickness of 20 nm to form a first hole transport layer 112-1, and N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)) represented by the above structural formula (iii) was deposited on the first hole transport layer 112-1 to a thickness of 10 nm to form a second hole transport layer 112-2.

[0378] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light-emitting layer 113.

[0379] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was deposited on the light-emitting layer 113 to a thickness of 10 nm to form the electron-transporting layer 114.

[0380] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting element 1 of this embodiment.

[0381] (Method of manufacturing light-emitting element 2) Light-emitting element 2 was fabricated in the same manner as light-emitting element 1, except that the electron-transport layer 114 was formed by evaporating 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (vii) to a thickness of 15 nm, and then evaporating NBPhen to a thickness of 10 nm.

[0382] The device structures of the light-emitting element 1 and the light-emitting element 2 are summarized in the table below.

[0383] [Table 1]

[0384] The light-emitting elements 1 and 2 were sealed with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting elements would not be exposed to the atmosphere (a sealant was applied around the elements, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), after which the initial characteristics and reliability of these light-emitting elements were measured. The measurements were performed at room temperature (an atmosphere maintained at 25°C).

[0385] The luminance-current density characteristics of the light-emitting element 1 and the light-emitting element 2 are shown in FIG 22, the current efficiency-luminance characteristics are shown in FIG 23, the luminance-voltage characteristics are shown in FIG 24, the current-voltage characteristics are shown in FIG 25, the external quantum efficiency-luminance characteristics are shown in FIG 26, and the emission spectrum is shown in FIG 27. 2 The main characteristics of the area are shown in Table 2.

[0386] [Table 2]

[0387] 22 to 27 and Table 2 show that Light-emitting Element 1 and Light-emitting Element 2, which are embodiments of the present invention, are blue light-emitting elements with favorable characteristics such as driving voltage and emission efficiency.

[0388] In addition, the current density is 50mA / cm 2 A graph showing changes in luminance with respect to driving time in the case of the light-emitting element 1 and the light-emitting element 2 according to one embodiment of the present invention is shown in Fig. 28. As shown in Fig. 28, it was found that the decrease in luminance with accumulation of driving time was small in the light-emitting element 1 and the light-emitting element 2, which are light-emitting elements according to one embodiment of the present invention, and thus the light-emitting elements have a long lifetime. EXAMPLES

[0389] Example 2 In this example, a light-emitting element 3 and a light-emitting element 4 according to one embodiment of the present invention described in Embodiment 2 will be described. The structural formulae of organic compounds used in the light-emitting element 3 and the light-emitting element 4 are shown below.

[0390] [ka]

[0391] (Method of Manufacturing Light-Emitting Element 3) First, indium tin oxide containing silicon oxide (ITSO) was formed by sputtering on a glass substrate to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the area of ​​the electrode was 2 mm×2 mm.

[0392] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0393] Then, 10 -4 The substrate was introduced into a vacuum deposition apparatus whose inside had been reduced in pressure to about Pa, and vacuum baking was carried out at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0394] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward. N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)) represented by the above structural formula (iii) and molybdenum oxide (VI) were co-deposited on the first electrode 101 by a deposition method using resistance heating to a thickness of 10 nm so as to have a weight ratio of 4:2 (=BBABnf(II)(4):molybdenum oxide), thereby forming a hole injection layer 111.

[0395] Next, BBABnf(II)(4) was deposited on the hole injection layer 111 to a thickness of 30 nm to form a hole transport layer 112.

[0396] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light-emitting layer 113.

[0397] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was deposited on the light-emitting layer 113 to a thickness of 10 nm to form the electron-transporting layer 114.

[0398] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting element 3 of this embodiment.

[0399] (Method of manufacturing light-emitting element 4) Light-emitting element 4 was fabricated in the same manner as light-emitting element 3, except that the electron-transport layer 114 was formed by evaporating 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (vii) to a thickness of 15 nm, and then evaporating NBPhen to a thickness of 10 nm.

[0400] The device structures of the light-emitting element 3 and the light-emitting element 4 are summarized in the table below.

[0401] [Table 3]

[0402] The light-emitting elements 3 and 4 were sealed with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting elements would not be exposed to the atmosphere (a sealant was applied around the elements, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), after which the initial characteristics and reliability of these light-emitting elements were measured. The measurements were performed at room temperature (an atmosphere maintained at 25°C).

[0403] The luminance-current density characteristics of the light-emitting element 3 and the light-emitting element 4 are shown in FIG. 29, the current efficiency-luminance characteristics are shown in FIG. 30, the luminance-voltage characteristics are shown in FIG. 31, the current-voltage characteristics are shown in FIG. 32, the external quantum efficiency-luminance characteristics are shown in FIG. 33, and the emission spectrum is shown in FIG. 2 The main characteristics of the area are shown in Table 4.

[0404] [Table 4]

[0405] 29 to 34 and Table 4 show that Light-emitting Element 3 and Light-emitting Element 4, which are embodiments of the present invention, are blue light-emitting elements with favorable characteristics such as driving voltage and emission efficiency.

[0406] In addition, the current density is 50mA / cm 2 A graph showing changes in luminance with respect to driving time in the case of the light-emitting element 3 and the light-emitting element 4 according to one embodiment of the present invention is shown in Fig. 35. As shown in Fig. 35, it was found that the decrease in luminance with accumulation of driving time was small in the light-emitting element 3 and the light-emitting element 4, which are light-emitting elements according to one embodiment of the present invention, and thus the light-emitting elements have a long lifetime. EXAMPLES

[0407] This example describes the light-emitting element 5 and the light-emitting element 6 which are one embodiment of the present invention described in Embodiment 2. The structural formulas of organic compounds used in the light-emitting element 5 and the light-emitting element 6 are shown below.

[0408] [ka]

[0409] (Method of Manufacturing Light-Emitting Element 5) First, indium tin oxide containing silicon oxide (ITSO) was formed by sputtering on a glass substrate to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the area of ​​the electrode was 2 mm×2 mm.

[0410] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0411] Then, 10 -4 The substrate was introduced into a vacuum deposition apparatus whose inside had been reduced in pressure to about Pa, and vacuum baking was carried out at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0412] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward. On the first electrode 101, N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)) represented by the above structural formula (iii) and 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ) were co-deposited to a thickness of 10 nm by a deposition method using resistance heating so that the weight ratio was 1:0.5 (=BBABnf(II)(4):F6-TCNNQ) to form a hole injection layer 111.

[0413] Next, BBABnf(II)(4) was deposited on the hole injection layer 111 to a thickness of 10 nm to form a first hole transport layer 112-1, and 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn) represented by the above structural formula (ix) was deposited on the first hole transport layer 112-1 to a thickness of 20 nm to form a second hole transport layer 112-2, thereby forming the hole transport layer 112.

[0414] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light-emitting layer 113.

[0415] Thereafter, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (vii) was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was deposited on the light-emitting layer 113 to a thickness of 10 nm, thereby forming an electron transport layer 114.

[0416] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting element 5 of this embodiment.

[0417] (Method of Manufacturing Light-Emitting Element 6) The light-emitting element 6 was fabricated in the same manner as the light-emitting element 5, except that the hole transport layer 112 was formed by vapor deposition of PCPPn to a thickness of 30 nm.

[0418] The device structures of the light-emitting elements 5 and 6 are summarized in the table below.

[0419] [Table 5]

[0420] The light-emitting elements 5 and 6 were sealed with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting elements were not exposed to the atmosphere (a sealant was applied around the elements, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), and then the initial characteristics and reliability of these light-emitting elements were measured. The measurements were performed at room temperature (an atmosphere maintained at 25°C).

[0421] FIG 36 shows the luminance-current density characteristics of the light-emitting element 5 and the light-emitting element 6, FIG 37 shows the current efficiency-luminance characteristics, FIG 38 shows the luminance-voltage characteristics, FIG 39 shows the current-voltage characteristics, FIG 40 shows the external quantum efficiency-luminance characteristics, and FIG 41 shows the emission spectrum. 2 The main characteristics of the area are shown in Table 6.

[0422] [Table 6]

[0423] 36 to 41 and Table 6 show that the light-emitting elements 5 and 6 which are embodiments of the present invention are blue light-emitting elements with favorable characteristics such as driving voltage and emission efficiency.

[0424] In addition, the current density is 50mA / cm 2 A graph showing changes in luminance with respect to drive time in the case of the light-emitting element 5 and the light-emitting element 6 according to one embodiment of the present invention is shown in Fig. 42. As shown in Fig. 42, it was found that the decrease in luminance with accumulation of drive time was small in the light-emitting element 5 and the light-emitting element 6, which are light-emitting elements according to one embodiment of the present invention, and thus the light-emitting elements have a long lifetime. EXAMPLES

[0425] Example 7 will describe the light-emitting element 7 which is one embodiment of the present invention described in Embodiment 2. The structural formula of an organic compound used in the light-emitting element 7 is shown below.

[0426] [ka]

[0427] (Method of Manufacturing Light-Emitting Element 7) First, indium tin oxide containing silicon oxide (ITSO) was formed by sputtering on a glass substrate to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the area of ​​the electrode was 2 mm×2 mm.

[0428] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0429] Then, 10 -4 The substrate was introduced into a vacuum deposition apparatus whose inside had been reduced in pressure to about Pa, and vacuum baking was carried out at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0430] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward. 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) represented by the above structural formula (i) was deposited to a thickness of 5 nm on the first electrode 101 by a deposition method using resistance heating to form a hole injection layer 111.

[0431] Next, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) represented by the above structural formula (ii) was deposited on the hole injection layer 111 to a thickness of 20 nm to form a first hole transport layer 112-1, and N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviation: BBABnf(II)(2)) represented by the above structural formula (x) was deposited on the first hole transport layer 112-1 to a thickness of 10 nm to form a second hole transport layer 112-2.

[0432] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light-emitting layer 113.

[0433] Then, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (vii) was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was deposited on the light-emitting layer 113 to a thickness of 10 nm, thereby forming an electron transport layer 114.

[0434] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting element 7 of this embodiment.

[0435] The device structure of the light-emitting device 7 is summarized in the table below.

[0436] [Table 7]

[0437] The light-emitting element 7 was placed in a glove box with a nitrogen atmosphere, and was sealed with a glass substrate so that the light-emitting element would not be exposed to the atmosphere (a sealant was applied around the element, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), after which the initial characteristics and reliability of the light-emitting element 7 were measured. The measurements were performed at room temperature (an atmosphere maintained at 25°C).

[0438] The luminance vs. current density characteristics of the light-emitting element 7 are shown in FIG 43, the current efficiency vs. luminance characteristics in FIG 44, the luminance vs. voltage characteristics in FIG 45, the current vs. voltage characteristics in FIG 46, the external quantum efficiency vs. luminance characteristics in FIG 47, and the emission spectrum in FIG 48. 2 The main characteristics of the area are shown in Table 8.

[0439] [Table 8]

[0440] 43 to 48 and Table 8 show that the light-emitting element 7 of one embodiment of the present invention is a blue light-emitting element with favorable characteristics such as driving voltage and luminous efficiency. EXAMPLES

[0441] Example 1 This example describes the light-emitting element 8 which is one embodiment of the present invention described in Embodiment 2. The structural formula of an organic compound used in the light-emitting element 8 is shown below.

[0442] [ka]

[0443] (Method of Manufacturing Light-Emitting Element 8) First, indium tin oxide containing silicon oxide (ITSO) was formed by sputtering on a glass substrate to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the area of ​​the electrode was 2 mm×2 mm.

[0444] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0445] Then, 10 -4The substrate was introduced into a vacuum deposition apparatus whose inside had been reduced in pressure to about Pa, and vacuum baking was carried out at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0446] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward. N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviation: BBABnf(II)(2)) represented by the above structural formula (x) and molybdenum oxide (VI) were co-deposited on the first electrode 101 to a thickness of 10 nm by a deposition method using resistance heating so as to have a weight ratio of 4:2 (=BBABnf(II)(2):molybdenum oxide). Thus, a hole injection layer 111 was formed.

[0447] Next, BBABnf(II)(2) was deposited on the hole injection layer 111 to a thickness of 30 nm to form a hole transport layer 112.

[0448] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light-emitting layer 113.

[0449] Then, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (vii) was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was deposited on the light-emitting layer 113 to a thickness of 10 nm, thereby forming an electron transport layer 114.

[0450] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting element 8 of this embodiment.

[0451] The device structure of the light-emitting device 8 is summarized in the table below.

[0452] [Table 9]

[0453] The light-emitting element 8 was sealed with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting element would not be exposed to the atmosphere (a sealant was applied around the element, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), and then the initial characteristics and reliability of the light-emitting element 8 were measured. The measurements were performed at room temperature (an atmosphere maintained at 25°C).

[0454] The luminance-current density characteristics of the light-emitting element 8 are shown in FIG 49, the current efficiency-luminance characteristics in FIG 50, the luminance-voltage characteristics in FIG 51, the current-voltage characteristics in FIG 52, the external quantum efficiency-luminance characteristics in FIG 53, and the emission spectrum in FIG 54. 2 The main characteristics of the area are shown in Table 10.

[0455] [Table 10]

[0456] 49 to 54 and Table 10 show that the light-emitting elements 3 and 4 of one embodiment of the present invention are blue light-emitting elements with favorable characteristics such as driving voltage and emission efficiency. EXAMPLES

[0457] Example 1 This example describes the light-emitting element 9 and the light-emitting element 10 which are one embodiment of the present invention described in Embodiment 2. The structural formulae of organic compounds used in the light-emitting element 9 and the light-emitting element 10 are shown below.

[0458] [ka]

[0459] (Method of Manufacturing Light-Emitting Element 9) First, indium tin oxide containing silicon oxide (ITSO) was formed by sputtering on a glass substrate to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the area of ​​the electrode was 2 mm×2 mm.

[0460] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0461] Then, 10 -4 The substrate was introduced into a vacuum deposition apparatus whose inside had been reduced in pressure to about Pa, and vacuum baking was carried out at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0462] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward. 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) represented by the above structural formula (i) was deposited to a thickness of 5 nm on the first electrode 101 by a deposition method using resistance heating to form a hole injection layer 111.

[0463] Next, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) represented by the above structural formula (ii) was deposited on the hole injection layer 111 to a thickness of 10 nm to form a first hole transport layer 112-1, N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)) represented by the above structural formula (iii) was deposited on the first hole transport layer 112-1 to a thickness of 10 nm to form a second hole transport layer 112-2, and 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole (abbreviation: PCzN2) represented by the above structural formula (xi) was deposited on the second hole transport layer 112-2 to a thickness of 10 nm to form a third hole transport layer 112-3.

[0464] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light-emitting layer 113.

[0465] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was deposited on the light-emitting layer 113 to a thickness of 10 nm to form the electron-transporting layer 114.

[0466] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting element 1 of this embodiment.

[0467] (Method of Manufacturing Light-Emitting Element 10) The light-emitting element 10 was fabricated in the same manner as the light-emitting element 9, except that the electron transport layer 114 was formed by evaporating 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (vii) to a thickness of 15 nm, and then evaporating NBPhen to a thickness of 10 nm.

[0468] The device structures of the light-emitting elements 9 and 10 are summarized in the table below.

[0469] [Table 11]

[0470] The light-emitting elements 9 and 10 were sealed with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting elements would not be exposed to the atmosphere (a sealant was applied around the elements, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), and then the initial characteristics and reliability of these light-emitting elements were measured. The measurements were performed at room temperature (an atmosphere maintained at 25°C).

[0471] The luminance-current density characteristics of the light-emitting element 9 and the light-emitting element 10 are shown in FIG. 55, the current efficiency-luminance characteristics in FIG. 56, the luminance-voltage characteristics in FIG. 57, the current-voltage characteristics in FIG. 58, the external quantum efficiency-luminance characteristics in FIG. 59, and the emission spectrum in FIG. 60. 2 The main characteristics of the area are shown in Table 12.

[0472] [Table 12]

[0473] 55 to 60 and Table 12 show that the light-emitting elements 9 and 10 which are embodiments of the present invention are blue light-emitting elements with favorable characteristics such as driving voltage and emission efficiency.

[0474] In addition, the current density is 50mA / cm 2 A graph showing changes in luminance with respect to drive time in the case of the light-emitting element 9 and the light-emitting element 10 according to one embodiment of the present invention is shown in Fig. 61. As shown in Fig. 61, it was found that the decrease in luminance with accumulation of drive time was small in the light-emitting element 9 and the light-emitting element 10, which are light-emitting elements according to one embodiment of the present invention, and thus the light-emitting element has a long lifetime. EXAMPLES

[0475] Example 1 This example describes the light-emitting element 11 and the light-emitting element 12 which are one embodiment of the present invention described in Embodiment 2. The structural formulae of organic compounds used in the light-emitting element 11 and the light-emitting element 12 are shown below.

[0476] [ka]

[0477] (Method of manufacturing light-emitting element 11) First, indium tin oxide containing silicon oxide (ITSO) was formed by sputtering on a glass substrate to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the area of ​​the electrode was 2 mm×2 mm.

[0478] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0479] Then, 10 -4 The substrate was introduced into a vacuum deposition apparatus whose inside had been reduced in pressure to about Pa, and vacuum baking was carried out at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes.

[0480] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward. 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) represented by the above structural formula (i) was deposited to a thickness of 5 nm on the first electrode 101 by a deposition method using resistance heating to form a hole injection layer 111.

[0481] Next, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) represented by the above structural formula (ii) was deposited on the hole injection layer 111 to a thickness of 10 nm to form a first hole transport layer 112-1, N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-2-amine (abbreviation: BBABnf(II)(2)) represented by the above structural formula (iii) was deposited on the first hole transport layer 112-1 to a thickness of 10 nm to form a second hole transport layer 112-2, and 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole (abbreviation: PCzN2) represented by the above structural formula (xi) was deposited on the second hole transport layer 112-2 to a thickness of 10 nm to form a third hole transport layer 112-3.

[0482] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) represented by the above structural formula (v) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6mMemFLPAPrn) to form the light-emitting layer 113.

[0483] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was deposited on the light-emitting layer 113 to a thickness of 10 nm to form the electron-transporting layer 114.

[0484] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting element 11 of this embodiment.

[0485] (Method of Manufacturing Light-Emitting Element 12) The light-emitting element 12 was fabricated in the same manner as the light-emitting element 11, except that the electron-transport layer 114 was formed by evaporating 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (vii) to a thickness of 15 nm, and then evaporating NBPhen to a thickness of 10 nm.

[0486] The device structures of the light-emitting elements 11 and 12 are summarized in the table below.

[0487] [Table 13]

[0488] The light-emitting elements 11 and 12 were sealed with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting elements would not be exposed to the atmosphere (a sealant was applied around the elements, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), and then the initial characteristics and reliability of these light-emitting elements were measured. The measurements were performed at room temperature (an atmosphere maintained at 25°C).

[0489] FIG 62 shows the luminance-current density characteristics of the light-emitting elements 11 and 12, FIG 63 shows the current efficiency-luminance characteristics, FIG 64 shows the luminance-voltage characteristics, FIG 65 shows the current-voltage characteristics, FIG 66 shows the external quantum efficiency-luminance characteristics, and FIG 67 shows the emission spectrum. 2 The main characteristics of the area are shown in Table 14.

[0490] [Table 14]

[0491] 62 to 67 and Table 14 show that Light-emitting Elements 11 and 12, which are embodiments of the present invention, are blue light-emitting elements with favorable characteristics such as driving voltage and emission efficiency.

[0492] In addition, the current density is 50mA / cm 2 A graph showing changes in luminance with respect to drive time in the case of the light-emitting element 11 and the light-emitting element 12 are shown in Fig. 68. As shown in Fig. 68, it was found that the light-emitting element 11 and the light-emitting element 12, which are light-emitting elements according to one embodiment of the present invention, show little decrease in luminance with accumulation of drive time and have a long lifetime. [Explanation of symbols]

[0493] 101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 112: hole transport layer, 112-1: first hole transport layer, 112-2: second hole transport layer, 112-3: third hole transport layer, 113: light emitting layer, 114: electron transport layer, 115: electron injection layer, 116: charge generation layer, 117: P-type layer, 118: electron relay layer, 119: electron injection buffer layer, 400: substrate, 401: first electrode, 403: EL layer, 404: second electrode, 405: sealing material, 406: sealing material, 407: sealing substrate, 412: pad, 420: IC chip, 501: positive electrode, 502: cathode, 511: first light-emitting unit, 512: second light-emitting unit, 513: charge generation layer, 601: driving circuit section (source line driving circuit), 602: pixel section, 603: driving circuit section (gate line driving circuit), 604: sealing substrate, 605: sealing material, 607: space, 608: wiring, 609: FPC (flexible printed circuit), 610: element substrate, 611: switching FET, 612: current control FET, 613: first electrode, 614: insulator, 616: EL layer, 617: second electrode, 618: light-emitting element, 951: substrate, 952: electrode, 95 3: insulating layer, 954: partition layer, 955: EL layer, 956: electrode, 1001: substrate, 1002: undercoat insulating film, 1003: gate insulating film, 1006: gate electrode, 1007: gate electrode, 1008: gate electrode, 1020: first interlayer insulating film, 1021: second interlayer insulating film, 1022: electrode, 1024W: anode, 1024R: anode, 1024G: anode, 1024B: anode, 1025: partition, 1028: EL layer, 1029: second electrode, 1031: sealing substrate, 1032: seal material, 1033: transparent base material, 1034R: red colored layer, 1034G: green colored layer, 1034B: blue coloring layer, 1035: black matrix, 1036: overcoat layer, 1037: third interlayer insulating film, 1040: pixel section, 1041: driving circuit section, 1042: peripheral section, 2001: housing, 2002: light source, 2100: robot, 2110: computing device, 2101: illuminance sensor, 2102: microphone, 2103: upper camera, 2104: speaker, 2105: display, 2106: lower camera, 2107: obstacle sensor, 2108: moving mechanism, 3001: lighting device, 5000: housing, 5001: display section, 5002: second display section,5003: speaker, 5004: LED lamp, 5005: operation key, 5006: connection terminal, 5007: sensor, 5008: microphone, 5012: support part, 5013: earphone, 5100: cleaning robot, 5101: display, 5102: camera, 5103: brush, 5104: operation button, 5150: mobile information terminal, 5151: housing, 5152: display area, 5153: bending part, 5120: dust, 5200: display area, 5201: display area, 5202: display area, 5203: display area, 7101: housing, 7103: Display unit, 7105: stand, 7107: display unit, 7109: operation keys, 7110: remote control unit, 7201: main body, 7202: housing, 7203: display unit, 7204: keyboard, 7205: external connection port, 7206: pointing device, 7210: second display unit, 7401: housing, 7402: display unit, 7403: operation buttons, 7404: external connection port, 7405: speaker, 7406: microphone, 7400: mobile phone, 9310: mobile information terminal, 9311: display panel, 9313: hinge, 9315: housing,

Claims

1. A hole injection layer and a light emitting layer are provided between an anode and a cathode, The light-emitting device further comprises a layer containing an organic compound represented by the following general formula (G1) between the hole-injection layer and the light-emitting layer: 【Chemistry 1】 (In the general formula (G1), R １ ~R １０ one of which is a group represented by the following general formula (g1), and the rest each independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 【Chemistry 2】 (However, in general formula (g1), Ar ３ , Ar ４ each independently represents any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the following general formula (g2) to the following general formula (g4). １ , Ar ２ each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms; n and m each independently represent an integer of 0 to 2; ３ is a group represented by the following general formula (g4), n is 1 or 2, and Ar ４ is a group represented by the following general formula (g4), m is 1 or 2. When n is 2, two Ar １ may be different or the same, and when m is 2, two Ar ２ may be different or the same. ３ , Ar ４ When Ar is an aromatic hydrocarbon group having 6 to 10 carbon atoms and has a substituent, the substituent is one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a group represented by the following general formulas (g2) to (g4). ３ and Ar ４ is a phenyl group, and the 2- and 6-positions of the phenyl group are substituted with aromatic hydrocarbon groups.) 【Chemistry 3】 (In the general formula (g2), R ３１ ~R ４０ one of which represents a single bond, and the nitrogen atom in the above general formula (g1), Ar ３ Or Ar ４ The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms. In addition, in the general formula (g3), R ４１ ~R ５０ one of which represents a single bond, and the nitrogen atom in the above general formula (g1), Ar ３ Or Ar ４ The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms. In addition, in general formula (g4), R ５１ ~R ６０ one of which represents a single bond, and Ar in the above general formula (g1) ３ Or Ar ４ The remainders each independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

2. In claim 1, The group represented by the general formula (g1) is R in the organic compound represented by the general formula (G1). ７ ~R １０ A light emitting device.

3. In claim 1, The group represented by the general formula (g1) is R in the organic compound represented by the general formula (G1). １ , R ８ and R １０ A light emitting device.

4. A hole injection layer and a light emitting layer are provided between an anode and a cathode, The light-emitting device further comprises a layer containing an organic compound represented by the following general formula (G2) between the hole-injection layer and the light-emitting layer: 【Chemistry 4】 (In the general formula (G2), R １７ ~R ２０ one of R is a group represented by the following general formula (g1), and the rest each independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. １１ ~R １６ each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 【Chemistry 5】 (However, in general formula (g1), Ar ３ , Ar ４ each independently represents any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and a group represented by the following general formula (g2) to the following general formula (g4). １ , Ar ２ each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 10 carbon atoms; n and m each independently represent an integer of 0 to 2; ３ is a group represented by the following general formula (g4), n is 1 or 2, and Ar ４ is a group represented by the following general formula (g4), m is 1 or 2. When n is 2, two Ar １ may be different or the same, and when m is 2, two Ar ２ may be different or the same. ３ , Ar ４ When is an aromatic hydrocarbon group having 6 to 10 carbon atoms and has a substituent, the substituent is one or more of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, fluorine, a haloalkyl group having 1 to 6 carbon atoms, and groups represented by the following general formulas (g2) to (g4): However, this does not include the case where the general formula (g1) has a [1,1':3',1''-terphenyl]-2'-amino group. 【Chemistry 6】 (In the general formula (g2), R ３１ ~R ４０ one of which represents a single bond, and the nitrogen atom in the above general formula (g1), Ar ３ Or Ar ４ The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms. In addition, in the general formula (g3), R ４１ ~R ５０ one of which represents a single bond, and the nitrogen atom in the above general formula (g1), Ar ３ Or Ar ４ The remainders each independently represent any one of a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms. In addition, in general formula (g4), R ５１ ~R ６０ one of which represents a single bond, and Ar in the above general formula (g1) ３ Or Ar ４ The remainders each independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, and a haloalkyl group having 1 to 6 carbon atoms.

5. In claim 4, The group represented by general formula (g1) is R １８ Or R ２０ A light emitting device coupled to the

6. In any one of claims 1 to 5, A light emitting device, wherein n and m are each independently 1 or 2.

7. In any one of claims 1 to 6, Ar ３ and Ar ４ each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms.

8. In any one of claims 1 to 7, Ar ３ and Ar ４ are each independently any one of a substituted or unsubstituted phenyl group and a substituted or unsubstituted naphthyl group.

9. In any one of claims 1 to 8, Ar １ and Ar ２ are each independently a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

10. In any one of claims 1 to 9, A light emitting device, wherein n and m are 2.

11. In any one of claims 1 to 10, A light emitting device, wherein n and m are 1.

12. In any one of claims 1 to 11, The light emitting device, wherein the light emitting layer comprises a fluorescent emitting material.

13. In any one of claims 1 to 11, The light emitting device, wherein the light emitting layer comprises a phosphorescent emissive material.

14. In any one of claims 1 to 11, The light-emitting device, wherein the light-emitting layer comprises a substance that exhibits thermally activated delayed fluorescence.

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