Organic compounds, optical devices, light-emitting devices, light-emitting apparatus, electronic devices and lighting apparatus

Abstract

Provided is a novel organic compound. Provided is an organic compound represented by general formula (G1). (In general formula (G1), either A or B is a group represented by the general formula (g1). Furthermore, the other of A and B, R1–R8, and R11–R14 each independently represent hydrogen, an C1-6 alkyl group, a C3-6 cyclic hydrocarbon group, a C1-6 alkoxy group, a cyano group, a halogen, a C1-6 haloalkyl group, or a substituted or unsubstituted C6-60 aromatic hydrocarbon group. R9 and R10 each independently represent hydrogen, a C1-6 alkyl group, a C3-6 cyclic hydrocarbon group, a C1-6 alkoxy group, a cyano group, halogen, a C1-6 haloalkyl group, or a substituted or unsubstituted phenyl group, and Ar represents a substituted or unsubstituted C6-13 aryl group.)

Description

[Technical field]

[0001] An embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, a display module, a lighting module, a display device, a light-emitting device, an electronic device, a lighting device, and an electronic 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, more specifically, examples of the technical field of an embodiment of the present invention disclosed in the present specification 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 devices (organic EL devices) that utilize electroluminescence (EL) using organic compounds are becoming more and more practical. The basic structure of these light-emitting devices 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 devices are self-luminous, when used as display pixels, they have advantages such as high visibility and no need for backlighting compared to liquid crystals, making them suitable for use as flat panel display elements. Another major advantage of displays using such light-emitting devices is that they can be made thin and lightweight. Another characteristic is that they have an extremely fast response speed.

[0004] In addition, these light-emitting devices can have light-emitting layers formed continuously in two dimensions, making it possible to obtain surface-like light emission. 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 valuable as surface light sources for lighting and other applications.

[0005] Displays and lighting devices using such light-emitting devices are suitable for use in a variety of electronic devices, but research and development is ongoing to find light-emitting devices with even better characteristics. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] China Patent Application Publication No. 108689972 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of one embodiment of the present invention is to provide a novel organic compound, a novel carrier-transporting material, or a novel hole-transporting material.

[0008] Another object of another embodiment of the present invention is to provide a light-emitting device with low driving voltage, or a light-emitting device, an electronic device, a display device, and an electronic device with low power consumption.

[0009] Note that the description of these problems does not preclude the existence of other problems. Note that one embodiment of the present invention does not necessarily have to solve all of these problems. Note that problems other than these will become apparent from the description of the specification, drawings, claims, etc., and it is possible to extract problems other than these from the description of the specification, drawings, claims, etc.

[0010] It is sufficient for the present invention to solve any one of the above problems. [Means for solving the problem]

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

[0012] [ka]

[0013] In the above general formula (G1), Q is an oxygen atom or a sulfur atom. One of A and B is a group represented by the following general formula (g1), and the other is any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. In addition, R 1 ~R 8 each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0014] [ka] In the above general formula (g1), R 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group; R 11 ~R 14each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0015] Another embodiment of the present invention is an organic compound in which, in the above structure, general formula (G1) is represented by the following general formula (G1-1):

[0016] [ka]

[0017] In the above general formula (G1-1), Q is an oxygen atom or a sulfur atom, and A is a group represented by the following general formula (g1), 20 represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 1 ~R 8 each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted alkyl group of an aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0018] [ka]

[0019] In the above general formula (g1), R 9 and R 10each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group; R 11 ~R 14 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0020] Another embodiment of the present invention is an organic compound having the above structure, in which general formula (G1) is represented by the following general formula (G1-2):

[0021] [ka]

[0022] In the above general formula (G1-2), Q is an oxygen atom or a sulfur atom. B is a group represented by the above general formula (g1), and R 20 represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 1 ~R 8 each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted alkyl group of an aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0023] [ka]

[0024] In the above general formula (g1), R 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group; R 11 ~R 14 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0025] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device comprising the steps of: 20 is an organic compound in which

[0026] Another embodiment of the present invention is an organic compound having the above structure, in which the group represented by general formula (g1) is a group represented by general formula (g1-1) below:

[0027] [ka]

[0028] In the above general formula (g1-1), R 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group, and each of R11 to R14 independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. Also, Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0029] Another embodiment of the present invention is an organic compound having the above structure, in which the group represented by general formula (g1) is a group represented by general formula (g1-2) below:

[0030] [ka]

[0031] In the above general formula (g1-2), R 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group; R 11 ~R 14 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0032] Alternatively, in another embodiment of the present invention, in the above structure, Ar is an organic compound represented by the following general formula (Ar-1) to (Ar-3).

[0033] [ka]

[0034] In the above general formulae (Ar-1) to (Ar-3), R A1 ~R A9 , R A11 ~R A19 and R A21 ~R A29each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0035] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device comprising the steps of: A1 ~R A9 , R A11 ~R A19 and R A21 ~R A29 is an organic compound in which

[0036] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device comprising the steps of: 9 and R 10 is an organic compound in which the methyl group is

[0037] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device comprising the steps of: 1 ~R 8 is an organic compound in which

[0038] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device comprising the steps of: 11 ~R 14 is an organic compound in which

[0039] Another embodiment of the present invention is an optical device including any of the organic compounds described above.

[0040] Another embodiment of the present invention is a light-emitting device including any of the above organic compounds.

[0041] Another embodiment of the present invention is an electronic device including any of the optical devices described above and a sensor, an operation button, a speaker, or a microphone.

[0042] Another embodiment of the present invention is a light-emitting device including the above optical device and a transistor or a substrate.

[0043] Another embodiment of the present invention is a lighting device including the above-described optical device and a housing.

[0044] In this specification, the light-emitting device includes an image display device using a light-emitting device. Also, a module in which a connector, such as an anisotropic conductive film or TCP (Tape Carrier Package), is attached to a light-emitting device, 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 device 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

[0045] In one aspect of the present invention, a novel organic compound can be provided. In one aspect of the present invention, a novel material for an electron transport layer can be provided. Or, in one aspect of the present invention, a novel host material for a phosphorescent light-emitting device can be provided.

[0046] According to another embodiment of the present invention, a light-emitting device with high emission efficiency can be provided. According to another embodiment of the present invention, a light-emitting device, a light-emitting device, an electronic device, a display device, and an electronic device with low power consumption can be provided.

[0047] 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]

[0048] 1A, 1B and 1C are schematic diagrams of a light emitting device. 2A and 2B are conceptual diagrams of an active matrix type light emitting device. 3A and 3B are conceptual diagrams of an active matrix type light emitting device. FIG. 4 is a conceptual diagram of an active matrix type light emitting device. 5A and 5B are conceptual diagrams of a passive matrix type light emitting device. 6A and 6B are diagrams illustrating a lighting device. 7A, 7B1, 7B2 and 7C are diagrams showing electronic devices. 8A, 8B and 8C are diagrams showing electronic devices. FIG. 9 is a diagram showing a lighting device. FIG. 10 is a diagram showing a lighting device. FIG. 11 is a diagram showing an in-vehicle display device and a lighting device. 12A and 12B are diagrams illustrating an electronic device. 13A, 13B and 13C are diagrams showing electronic devices. Figures 14A and 14B show the relationship between oFBiBnf(6) 1 1 H NMR chart. Figure 15 shows the absorption and emission spectra of oFBiBnf(6) in a toluene solution. Figure 16 shows the absorption and emission spectra of oFBiBnf(6) in a thin film state. Figures 17A and 17B show the relationship between oFBi(4)Bnf(6). 1 1 H NMR chart. Figure 18 shows the absorption and emission spectra of oFBi(4)Bnf(6) in toluene solution. Figure 19 shows the absorption and emission spectra of oFBi(4)Bnf(6) in a thin film state. Figures 20A and 20B show the relationship between FBi(4) and Bnf(6). 1 1 H NMR chart. Figure 21 shows the absorption and emission spectra of FBi(4)Bnf(6) in a toluene solution. Figure 22 shows the absorption and emission spectra of FBi(4)Bnf(6) in a thin film state. Figures 23A and 23B show the 11 H NMR chart. Figure 24 shows the absorption and emission spectra of FBiBnf(6) in a toluene solution. Figure 25 shows the absorption and emission spectra of FBiBnf(6) in a thin film state. FIG. 26 shows the luminance-current density characteristics of the light-emitting device 1 and the comparative light-emitting device 1. FIG. 27 shows the current efficiency-luminance characteristics of the light-emitting device 1 and the comparative light-emitting device 1. FIG. 28 shows the luminance-voltage characteristics of the light-emitting device 1 and the comparative light-emitting device 1. FIG. 29 shows the current-voltage characteristics of the light-emitting device 1 and the comparative light-emitting device 1. FIG. 30 shows the external quantum efficiency-luminance characteristics of the light-emitting device 1 and the comparative light-emitting device 1. FIG. 31 shows the emission spectra of the light-emitting device 1 and the comparative light-emitting device 1. FIG. 32 shows the luminance-current density characteristics of the light-emitting device 2 and the comparative light-emitting device 2. FIG. 33 shows the current efficiency-luminance characteristics of the light-emitting device 2 and the comparative light-emitting device 2. FIG. 34 shows the luminance-voltage characteristics of the light-emitting device 2 and the comparative light-emitting device 2. FIG. 35 shows the current-voltage characteristics of the light-emitting device 2 and the comparative light-emitting device 2. FIG. 36 shows the external quantum efficiency-luminance characteristics of the light-emitting device 2 and the comparative light-emitting device 2. FIG. 37 shows the emission spectra of the light-emitting device 2 and the comparative light-emitting device 2. FIG. 38 shows normalized luminance-time change characteristics of the light-emitting device 1 and the comparative light-emitting device 1. FIG. 39 shows normalized luminance-time change characteristics of the light-emitting device 2 and the comparative light-emitting device 2. FIG. 40 shows the luminance-current density characteristics of the light-emitting device 3 and the comparative light-emitting device 3. FIG. 41 shows the current efficiency-luminance characteristics of the light-emitting device 3 and the comparative light-emitting device 3. FIG. 42 shows the luminance-voltage characteristics of the light-emitting device 3 and the comparative light-emitting device 3. FIG. 43 shows the current-voltage characteristics of the light-emitting device 3 and the comparative light-emitting device 3. FIG. 44 shows the external quantum efficiency-luminance characteristics of the light-emitting device 3 and the comparative light-emitting device 3. FIG. 45 shows the emission spectra of the light-emitting device 3 and the comparative light-emitting device 3. FIG. 46 shows the luminance-current density characteristics of the light-emitting device 4 and the comparative light-emitting device 4. FIG. 47 shows the current efficiency-luminance characteristics of the light-emitting device 4 and the comparative light-emitting device 4. FIG. 48 shows the luminance-voltage characteristics of the light-emitting device 4 and the comparative light-emitting device 4. FIG. 49 shows the current-voltage characteristics of the light-emitting device 4 and the comparative light-emitting device 4. FIG. 50 shows the external quantum efficiency-luminance characteristics of the light-emitting device 4 and the comparative light-emitting device 4. FIG. 51 shows the emission spectra of Light-Emitting Device 4 and Comparative Light-Emitting Device 4. FIG. 52 shows the normalized luminance-time change characteristics of the light-emitting device 3 and the comparative light-emitting device 3. FIG. 53 shows the normalized luminance-time change characteristics of the light-emitting device 4 and the comparative light-emitting device 4. FIG. 54 shows the luminance-current density characteristics of the light-emitting device 5 and the light-emitting device 6. FIG. 55 shows the current efficiency-luminance characteristics of the light-emitting device 5 and the light-emitting device 6. FIG. 56 shows the luminance-voltage characteristics of the light-emitting device 5 and the light-emitting device 6. FIG. 57 shows the current-voltage characteristics of the light-emitting device 5 and the light-emitting device 6. FIG. 58 shows the external quantum efficiency-luminance characteristics of the light-emitting device 5 and the light-emitting device 6. FIG. 59 shows the emission spectra of light-emitting device 5 and light-emitting device 6. Figure 60A and Figure 60B show the 1 1 H NMR chart. Figure 61 shows the absorption and emission spectra of FBiBnf(8) in a toluene solution. Figure 62 shows the absorption and emission spectra of FBiBnf(8) in a thin film state. Figure 63A and Figure 63B show the 1 1 H NMR chart. Figure 64 shows the absorption and emission spectra of oFBiBnf(8) in a toluene solution. Figure 65 shows the absorption and emission spectra of oFBiBnf(8) in a thin film state. Figure 66A and Figure 66B show the relationship between FBi(4) and Bnf(8). 1 1 H NMR chart. Figure 67 shows the absorption and emission spectra of FBi(4)Bnf(8) in toluene solution. Figure 68 shows the absorption and emission spectra of FBi(4)Bnf(8) in a thin film state. Figure 69 shows the absorption and emission spectra of oFBi(4)Bnf(8) in toluene solution. Figure 70 shows the absorption and emission spectra of oFBi(4)Bnf(8) in a thin film state. FIG. 71 shows the luminance-current density characteristics of the light-emitting device 7 and the light-emitting device 8. As shown in FIG. FIG. 72 shows the current efficiency-luminance characteristics of the light-emitting device 7 and the light-emitting device 8. FIG. 73 shows the luminance-voltage characteristics of the light-emitting device 7 and the light-emitting device 8. As shown in FIG. FIG. 74 shows the current-voltage characteristics of the light-emitting device 7 and the light-emitting device 8. FIG. 75 shows the external quantum efficiency-luminance characteristics of the light-emitting device 7 and the light-emitting device 8. As shown in FIG. FIG. 76 shows the emission spectra of light-emitting device 7 and light-emitting device 8. FIG. 77 shows the normalized luminance-time change characteristics of the light-emitting device 7 and the light-emitting device 8. FIG. 78 shows the luminance-current density characteristics of the light-emitting device 9 and the comparative light-emitting device 5. FIG. 79 shows the current efficiency-luminance characteristics of the light-emitting device 9 and the comparative light-emitting device 5. FIG. 80 shows the luminance-voltage characteristics of the light-emitting device 9 and the comparative light-emitting device 5. FIG. 81 shows the current-voltage characteristics of the light-emitting device 9 and the comparative light-emitting device 5. FIG. 82 shows the external quantum efficiency-luminance characteristics of the light-emitting device 9 and the comparative light-emitting device 5. FIG. 83 shows the emission spectra of Light-Emitting Device 9 and Comparative Light-Emitting Device 5. FIG. 84 shows the normalized luminance-time change characteristics of the light-emitting device 9 and the comparative light-emitting device 5. FIG. 85 shows the luminance-current density characteristics of the light-emitting device 10. FIG. 86 shows the current efficiency-luminance characteristics of the light-emitting device 10. FIG. 87 shows the luminance-voltage characteristics of the light-emitting device 10. FIG. 88 shows the current-voltage characteristics of the light emitting device 10. FIG. 89 shows the external quantum efficiency-luminance characteristics of the light emitting device 10. FIG. 90 is the emission spectrum of the light emitting device 10. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0049] 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.

[0050] (Embodiment 1) In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0051] An organic compound according to one embodiment of the present invention is represented by the following general formula (G1).

[0052] [ka]

[0053] The above general formula (G1) can also be expressed as the following general formulas (G1-1) and (G1-2).

[0054] [ka]

[0055] [ka]

[0056] In the organic compounds represented by the general formulas (G1), (G1-1) and (G1-2), Q is an oxygen atom or a sulfur atom. When Q is an oxygen atom, the refractive index is lower than that of a compound having a sulfur atom, and an element using a compound with a lower refractive index has an effect of increasing the light extraction efficiency, which is preferable because a highly efficient light-emitting device can be provided.

[0057] In addition, one of A and B in the above general formula (G1), A in the above general formula (G1-1), and B in the above general formula (G1-2) are each a group represented by the following general formula (g1).

[0058] [ka]

[0059] In the group represented by the general formula (g1), the position where the nitrogen of the amine is bonded to the fluorenyl group is preferably the 2nd or 4th position. That is, when the group represented by the general formula (g1) is a group represented by the following general formula (g1-1), it becomes a compound having a fluorene-2-amine skeleton, so that a compound with a relatively shallow HOMO and high transportability can be provided, and as a result, a light-emitting device with low power consumption can be provided. In addition, when it is a group represented by the following general formula (g1-1), it is easy to synthesize, and there is also a merit in terms of cost. Alternatively, when the general formula (g1) is a group represented by the following general formula (g1-2), it is preferable because a device with high light-emitting efficiency can be provided.

[0060] [ka]

[0061] [ka]

[0062] In the groups represented by the above general formulae (g1), (g1-1) and (g1-2), Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. In order to provide a highly efficient and reliable device, it is preferable that Ar is a group represented by the following general formulae (Ar-1) to (Ar-3). In addition, when Ar in general formula (g1-2) is a group represented by the following general formulae (Ar-1) to (Ar-3), it is easy to synthesize, and there is a cost advantage in providing the compound.

[0063] [ka]

[0064] In the above general formulae (Ar-1) to (Ar-3), R A1 ~R A9 , R A11 ~R A19 and R A21 ~R A29 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. A1 ~R A9 , R A11 ~R A19 and R A21 ~R A29 is preferably a hydrogen atom, a phenyl group, a biphenyl group, or a fluorenyl group, since it is possible to provide compounds and devices having high heat resistance, high reliability, and low power consumption, and the synthesis is easy and the raw materials are easily available.

[0065] In addition, in the groups represented by the above general formulae (g1), (g1-1) and (g1-2), R 9 and R 10each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. 9 and R 10 When R is an alkyl group having 1 to 6 carbon atoms, R 9 and R 10 may be bonded to each other to form a ring, forming a spiro structure.

[0066] [ka]

[0067] In the groups represented by the above general formulae (G1), (G1-1), (G1-2), (g1), (g1-1) and (g1-2), the other of A and B, R 1 ~R 8 , R 11 ~R 14 , and R 20 each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0068] In addition, in the present specification, when a group described as being "substituted or unsubstituted" has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, a phenyl group, a biphenyl group (an o-biphenyl group, an m-biphenyl group, and a p-biphenyl group), and a naphthyl group.

[0069] Specific examples of the hydrocarbon group having 1 to 6 carbon atoms, the cyclic hydrocarbon group having 3 to 6 carbon atoms, the alkoxy group having 1 to 6 carbon atoms, the cyano group, the halogen, and the haloalkyl group having 1 to 6 carbon atoms include those represented by the following structural formulas (1-1) to (1-40).

[0070] [ka]

[0071] Specific examples of the aromatic hydrocarbon group having 6 to 60 carbon atoms include substituents represented by the following structural formulas (2-1) to (2-13). The positions of substitution in the following structural formulas (2-1) to (2-13) are not important. These may have a substituent.

[0072] [ka]

[0073] In addition, R 1 ~R 8 , R 11 ~R 14 When is an aromatic hydrocarbon group, among the above structural formulas (2-1) to (2-13), structural formulas (2-1) to (2-3) and structural formula (2-9) are preferable. The substitution position of these aromatic hydrocarbon groups is not important. Specific examples of such aromatic hydrocarbon groups and those hydrocarbon groups having a substituent are shown in structural formulas (1-41) to (1-50) below.

[0074] [ka]

[0075] Specific examples of the groups represented by the above general formulae (g1), (g1-1), (g1-2) and (g3-1) to (g3-4) are shown below.

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] The organic compound according to one embodiment of the present invention having the above-described structure has a high carrier-transporting property. In particular, the organic compound has a high hole-transporting property, and even if the organic compound is formed as a thick film, the increase in driving voltage is small, and a light-emitting device having favorable characteristics can be obtained. The organic compound having the above-described structure can be suitably used as a hole-injection layer and a hole-transport layer of a light-emitting device.

[0080] Specific examples of organic compounds having the above structure are shown below.

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] Next, a method for synthesizing the organic compound as described above will be described with reference to an organic compound represented by the following general formula (G1-1a). General formula (G1-1a) is a molecular structure in which A in the general formula (G1) is general formula (g1), and the molecular structure of (g1) is fluorene-2-amine.

[0091] [ka]

[0092] The organic compound represented by general formula (G1-1a) can be synthesized according to the following synthesis schemes (a-1) and (a-2).

[0093] First, an arylamine compound (compound 1) and a fluorene compound (compound 2) are coupled according to reaction formula (a-1) to obtain a fluorenylamine compound (compound 3). Next, a fluorenylamine compound (compound 3) and a benzonaphthofuran compound (compound 4) are coupled according to reaction formula (a-2) to obtain the desired benzonaphthofuranylamine compound (G1-1a). The synthesis schemes (a-1) and (a-2) are shown below.

[0094] [ka]

[0095] [ka]

[0096] In the synthetic schemes (a-1) and (a-2), Q is an oxygen atom or a sulfur atom. 1 ~R 8 and R 11 ~R 14 represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group, and Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0097] In addition, in the synthesis schemes (a-1) and (a-2), X 1 ~X 2 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group.

[0098] 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(orthotolyl)phosphine, and (S)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diisopropylphosphine) (abbreviation: cBRIDP) can be used. In this reaction, an organic base such as sodium tert-butoxide, or an inorganic base such as potassium carbonate, cesium carbonate, or sodium carbonate can be used. In this reaction, toluene, xylene, benzene, tetrahydrofuran, dioxane, or the like can be used as a solvent. The reagents that can be used in this reaction are not limited to the above-mentioned reagents. In addition, a compound in which an organotin group is bonded to an amino group can be used instead of compound 1 or compound 3.

[0099] In addition, in the synthesis schemes (a-1) and (a-2), the Ullmann reaction can be carried out using copper or a copper compound. In this reaction, copper or a copper compound can be used. 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, benzene, and the like. In the Ullmann reaction, it is preferable to use DMPU or xylene, which have a high boiling point, 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. Reagents that can be used in this reaction are not limited to the above-mentioned reagents.

[0100] Compound 3 can also be synthesized by coupling an aryl compound (compound 5) with a fluorenylamine compound (compound 6) as shown in the following synthesis scheme (a-3).

[0101] [ka]

[0102] In the synthetic scheme (a-3), R 11 ~R 14 represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group, and Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0103] In the synthetic scheme (a-3), X 3 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. In the synthesis scheme (a-3), the same reaction conditions as those in the synthesis schemes (a-1) and (a-2) can be used.

[0104] The organic compound represented by the above general formula (G1-1a) can also be synthesized according to the following synthesis schemes (b-1) and (b-2).

[0105] First, according to reaction formula (b-1), an arylamine compound (compound 1) and a benzonaphthofuran compound (compound 4) are coupled to obtain a benzonaphthofuranylamine compound (compound 7). Next, according to reaction formula (b-2), a benzonaphthofuranylamine compound (compound 7) and a fluorene compound (compound 2) are coupled to obtain the desired benzonaphthofuranylamine compound (G1-1a). The synthesis schemes (b-1) and (b-2) are shown below.

[0106] [ka]

[0107] [ka]

[0108] In the synthetic schemes (b-1) and (b-2), Q is an oxygen atom or a sulfur atom. 1 ~R 8 and R 11 ~R 14 represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group, and Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0109] In the synthesis schemes (b-1) and (b-2), X 1 ~X 2 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group.

[0110] In the synthetic schemes (b-1) and (b-2), when the Buchwald-Hartwig reaction using a palladium catalyst or the Ullmann reaction using copper or a copper compound is performed, the same reaction conditions as those in the synthetic schemes (a-1) and (a-2) can be used.

[0111] Compound 7 can also be synthesized by coupling an aryl compound (compound 5) with a benzonaphthofuranylamine compound (compound 6) as shown in the following synthesis scheme (b-3).

[0112] [ka]

[0113] In the synthetic scheme (b-3), Q is an oxygen atom or a sulfur atom. 1 ~R 8 represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. In addition, Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0114] In the synthetic scheme (b-3), X 3 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. In the synthesis scheme (b-3), the same reaction conditions as those in the synthesis schemes (a-1) and (a-2) can be used.

[0115] The organic compound represented by the above general formula (G1-1a) can also be synthesized according to the following synthesis schemes (c-1) and (c-2).

[0116] First, according to reaction formula (c-1), a fluorenylamine compound (compound 6) and a benzonaphthofuran compound (compound 4) are coupled to obtain a benzonaphthofuranylamine compound (compound 8). Next, according to reaction formula (c-2), a benzonaphthofuranylamine compound (compound 8) and an aryl compound (compound 5) are coupled to obtain the desired benzonaphthofuranylamine compound (G1-1a). The synthesis schemes (c-1) and (c-2) are shown below.

[0117] [ka]

[0118] [ka]

[0119] In the synthetic schemes (c-1) and (c-2), Q is an oxygen atom or a sulfur atom. 1 ~R 8 and R 11 ~R 14 represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group, and Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0120] In the synthetic schemes (c-1) and (c-2), X 2 ~X 3 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group.

[0121] In the synthetic schemes (c-1) and (c-2), when the Buchwald-Hartwig reaction using a palladium catalyst or the Ullmann reaction using copper or a copper compound is performed, the same reaction conditions as those in the synthetic schemes (a-1) and (a-2) can be used.

[0122] Compound 8 can also be synthesized according to the following synthesis scheme (c-3).

[0123] [ka]

[0124] In the synthetic scheme (c-3), Q is an oxygen atom or a sulfur atom. 1 ~R 8 and R 11 ~R 14 represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 9 and R 10 each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group.

[0125] In the synthetic scheme (c-3), X 1 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. In the synthesis scheme (c-3), the same reaction conditions as those in the synthesis schemes (a-1) and (a-2) can be used.

[0126] The synthesis methods of the organic compound represented by general formula (G1-1a) are not limited to the above-mentioned synthesis schemes (a-1) and (a-3), the synthesis schemes (b-1) and (b-3), and the synthesis schemes (c-1) and (c-3).

[0127] The above is the description of the synthesis method for the general formula (G1-1a) in which A is the general formula (g1) in the general formula (G1) and the molecular structure of (g1) is fluorene-2-amine. In the general formula (G1), A is the general formula (g1) and the molecular structure of (g1) is fluorene-1-amine, or the molecular structure of (g1) is fluorene-3-amine, or the molecular structure of (g1) is fluorene-4-amine. The synthesis of the compound in which A is the general formula (g1) in the general formula (G1) and the molecular structure of (g1) is fluorene-1-amine, or the molecular structure of (g1) is fluorene-3-amine, or the molecular structure of (g1) is fluorene-4-amine can also be performed by making the substituent of the fluorene compound 1-position, 3-position, or 4-position in the synthesis schemes (a-1) and (a-3), synthesis schemes (b-1) and (b-3), and synthesis schemes (c-1) and (c-3).

[0128] Furthermore, in the case where B in general formula (G1) is general formula (g1), the benzonaphthofuran-6-amine compound of the present invention can be obtained by using a compound having a substituent at the 6-position of benzonaphthofuran as a raw material.

[0129] (Embodiment 2) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described.

[0130] 1A illustrates a light-emitting device according to one embodiment of the present invention. The light-emitting device according to one embodiment of the present invention includes a first electrode 101, a second electrode 102, and an EL layer 103. The EL layer 103 includes the organic compound described in Embodiment 1.

[0131] The EL layer 103 has a light-emitting layer 113, and the light-emitting layer 113 contains a light-emitting material. A hole injection layer 111 and a hole transport layer 112 are provided between the light-emitting layer 113 and the first electrode 101. The organic compound described in the embodiment 1 is preferably used for the hole injection layer 111 and the hole transport layer 112 because it has high carrier transport properties, particularly hole transport properties.

[0132] The light-emitting layer 113 may contain the organic compound and the electron-transporting material described in Embodiment 1 together with the light-emitting material. In this case, the organic compound and the electron-transporting material described in Embodiment 1 may form an exciplex. By forming an exciplex having an appropriate emission wavelength, effective energy transfer to the light-emitting material can be realized, and a light-emitting device with high efficiency and good lifetime can be provided.

[0133] 1A shows the EL layer 103 including the light-emitting layer 113, the hole injection layer 111, the hole transport layer 112, the electron transport layer 114, and the electron injection layer 115, but the configuration of the light-emitting device is not limited to these. Any of these layers may not be formed, or a layer having another function may be included.

[0134] Next, examples of the detailed structure and materials of the above-mentioned light-emitting device will be described. As described above, the light-emitting device according to one embodiment of the present invention has an EL layer 103 composed of multiple layers between a pair of electrodes, the first electrode 101 and the second electrode 102, and any part of the EL layer 103 contains the organic compound disclosed in the first embodiment.

[0135] 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.

[0136] The EL layer 103 preferably has a laminated structure, but the laminated structure is not particularly limited, and various layer structures such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a carrier block layer, an exciton block layer, and a charge generation layer can be applied. In this embodiment, two types of structures will be described: 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 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. The materials constituting each layer are specifically described below.

[0137] The hole-injection layer 111 is a layer containing a substance having an acceptor property. As the substance having an acceptor property, either an organic compound or an inorganic compound can be used.

[0138] As the substance having acceptor properties, a compound having an electron-withdrawing group (a halogen group or a cyano group) can be used, and examples thereof include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile, and the like. In particular, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, are thermally stable and preferred. Radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) [3] are preferred because they have a very high electron-accepting property, and specific examples thereof include α,α',α''-1,2,3-cyclopropane triylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropane triylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropane triylidene tris[2,3,4,5,6-pentafluorobenzeneacetonitrile]. As the substance having acceptor properties, in addition to the organic compounds described above, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used. In addition, the hole injection layer 111 can be formed by a phthalocyanine complex compound such as phthalocyanine (abbreviation: HPc) or copper phthalocyanine (CuPc), 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), etc.A substance having acceptor properties can extract electrons from an adjacent hole transport layer (or hole transport material) when an electric field is applied.

[0139] A composite material in which the above-mentioned acceptor substance is contained in a material having a hole transport property can also be used as the hole injection layer 111. Note that by using a composite material in which the acceptor substance is contained in a material having a hole transport property, a material for forming an electrode can be selected regardless of the work function. That is, not only a material with a high work function but also a material with a low work function can be used as the first electrode 101.

[0140] As a material having a hole transport property 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. Note that as a material having a hole transport property used in the composite material, a 1×10 -6 cm 2 A material having a hole mobility of 100 / Vs or more is preferable. Specific examples of organic compounds that can be used as a material having a hole transport property in a composite material are listed below.

[0141] 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-phenylcarbazole (abbreviation: PCzPCA3), Examples of compounds that can be used include tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (abbreviation: CzPA), and 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene.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).

[0142] 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.

[0143] The material having hole transport properties used in the composite material preferably has any one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, the second organic compound may be an aromatic amine having a substituent containing a dibenzofuran ring or a dibenzothiophene ring, an aromatic monoamine having a naphthalene ring, or an aromatic monoamine in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group. It is preferable that the second organic compound is a substance having an N,N-bis(4-biphenyl)amino group, because a light-emitting device with a long life can be manufactured. Specific examples of the second organic compound include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8 -yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d] Furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: : BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-Diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl- 1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: m TPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tris(1,1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-diphenyl-4'-(2-naphthyl)-4''-{9-(4-biphenylyl)carbazole)}triphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] -N-[4-(1-naphthyl)phenyl]-9,9'-spirobi(9H-fluorene)-2-amine (abbreviation: PCBNBSF), N,N-bis(4-biphenylyl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(1,1'-biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-Dimethyl-9H-fluoren-2-yl)-9,9'-spirobi(9H-fluorene)-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(dibenzofuran-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4 -phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 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: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-1-amine, etc. can be mentioned.

[0144] Note that the material having a hole-transporting property used in the composite material is more preferably a substance having a relatively deep HOMO level of −5.7 eV or more and −5.4 eV or less. When the material having a hole-transporting property used in the composite material has a relatively deep HOMO level, it becomes easy to inject holes into the hole-transporting layer 112, and it becomes easy to obtain a light-emitting device with a long lifetime.

[0145] The organic compound described in Embodiment 1 can be suitably used as a material having a hole-transporting property for the composite material.

[0146] The refractive index of the layer can be reduced by further mixing an alkali metal or alkaline earth metal fluoride with the composite material (preferably with an atomic ratio of fluorine atoms of 20% or more in the layer). This also makes it possible to form a layer with a low refractive index inside the EL layer 103, thereby improving the external quantum efficiency of the light-emitting device.

[0147] By forming the hole injection layer 111, the hole injection property is improved, and a light emitting device with a low driving voltage can be obtained. In addition, organic compounds having acceptor properties are easy to use because they can be easily evaporated and formed into a film.

[0148] The hole transport layer 112 is formed by including a material having a hole transport property. -6 cm 2The hole transporting material preferably has a hole mobility of 1000 or more Vs. Examples of the hole transporting material 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: B PAFLP), 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: Aromatic amines such as PCBANB), 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), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF). 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 transportability, and contribute to reducing the driving voltage. The substances given as examples of materials having a hole transport property used in the composite material of the hole injection layer 111 can also be suitably used as materials for the hole transport layer 112. The organic compounds described in embodiment 1 have high hole transport properties and can therefore be very suitably used as materials for the hole transport layer 112. In addition, since the organic compounds described in embodiment 1 have high hole transport properties, even if the hole transport layer 112 is formed to a thickness of 100 nm or more, a light-emitting device can be provided in which the increase in driving voltage is small and the device has good element characteristics. By making the hole transport layer 112 thick, the optical path length between the electrodes can be easily adjusted, which makes it easy to appropriately configure a microcavity structure.

[0149] The light-emitting layer 113 contains a light-emitting substance and a host material. The light-emitting layer 113 may contain other materials at the same time. The light-emitting layer 113 may also be a laminate of two layers having different compositions.

[0150] The luminescent material may be a fluorescent material, a phosphorescent material, a material exhibiting thermally activated delayed fluorescence (TADF), or any other luminescent material.

[0151] Examples of materials that can be used as the fluorescent substance in the light-emitting layer 113 include 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) 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 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: 2DPABPhA), 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-diphenyltetrahydrofuran N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 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',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (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'-(Pi 1,6BnfAPrn-03), 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02). 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. Other fluorescent substances can also be used.

[0152] In the case where a phosphorescent material is used as the light-emitting material in the light-emitting layer 113, examples of materials that can be used include 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, Organometallic iridium complexes with a 4H-triazole skeleton, such as tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz)3]) and 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-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]) Organometallic iridium complexes with 1H-triazole skeletons, such as tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) and tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), and fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl- Organometallic iridium complexes with an imidazole skeleton, such as tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(iPrpmi)3]) and tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), and bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), 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 (abbreviated as FIracac), are examples of such compounds. These are compounds that exhibit blue phosphorescence and have a peak emission wavelength between 440 nm and 520 nm.

[0153] 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-( Organometallic iridium complexes having a pyrimidine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and organometallic iridium complexes having a pyrazine skeleton, such as tris(2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2’)iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C 2’ )iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridyl-κN2)phenyl-κ]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mbfpypy-d3)]), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridyl-κN2)phenyl-κ]iridium(III) In addition to organometallic iridium complexes having a pyridine skeleton such as furo[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy-d3)]), rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]) can be mentioned. These are compounds that mainly exhibit green phosphorescence, and have a peak emission wavelength 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.

[0154] In addition, organometallic iridium complexes having a pyrimidine skeleton, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), and bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), Organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), and tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ In addition to organometallic iridium complexes with a pyridine skeleton such as iridium(III) acetylacetonate (abbreviated as [Ir(piq)2(acac)]), platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP), and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviated as [Eu(DBM)3(Phen)]) and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviated as [Eu(TTA)3(Phen)]) are examples of such compounds. These are compounds that exhibit red phosphorescence and have a peak emission wavelength of 600 to 700 nm. Furthermore, an organometallic iridium complex having a pyrazine skeleton can emit red light with good chromaticity.

[0155] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting substances may be selected and used.

[0156] TADF materials include fullerene and its derivatives, acridine and its derivatives, eosin derivatives, etc. Also included are metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), etc. Examples of the metal-containing porphyrin include protoporphyrin-tin fluoride complex (SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), etioporphyrin-tin fluoride complex (SnF2(Etio I)), and octaethylporphyrin-platinum chloride complex (PtCl2OEP), which are shown in the following structural formulas.

[0157] [ka]

[0158] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 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 (abbreviation: PCCzPTzn), Heterocyclic compounds having one or both of a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, such as 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA), 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, and is therefore preferred. Among the skeletons having a π-electron deficient heteroaromatic ring, the pyridine skeleton, the diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and the triazine skeleton are preferred because they are stable and reliable. In particular, the benzofuropyrimidine skeleton, the benzothienopyrimidine skeleton, the benzofuropyrazine skeleton, and the benzothienopyrazine skeleton are preferred because they have high acceptor properties and good reliability. In addition, among the skeletons having a π-electron rich heteroaromatic ring, the acridine skeleton, the phenoxazine skeleton, the phenothiazine skeleton, the furan skeleton, the thiophene skeleton, and the pyrrole skeleton are preferred because they are stable and reliable.In addition, the furan skeleton is preferably a dibenzofuran skeleton, and the thiophene skeleton is preferably a dibenzothiophene skeleton. In addition, the pyrrole skeleton is particularly preferably an indole skeleton, a carbazole skeleton, an indolocarbazole skeleton, a bicarbazole skeleton, or a 3-(9-phenyl-9H-carbazol-3-yl)-9H-carbazole skeleton. In addition, a substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded is particularly preferable because the electron donating property of the π-electron-rich heteroaromatic ring and the electron accepting property of the π-electron-deficient heteroaromatic ring are both strong, and the energy difference between the S1 level and the T1 level is small, so that thermally activated delayed fluorescence can be efficiently obtained. In addition, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used instead of the π-electron-deficient heteroaromatic ring. In addition, an aromatic amine skeleton, a phenazine skeleton, or the like can be used as the π-electron-rich skeleton. In addition, examples of the π-electron-deficient skeleton that can be used include a xanthene skeleton, a thioxanthene dioxide skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or boranthrene, an aromatic ring or a heteroaromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, etc. In this way, a π-electron-deficient skeleton and a π-electron-rich skeleton can be used in place of at least one of a π-electron-deficient heteroaromatic ring and a π-electron-rich heteroaromatic ring.

[0159] [ka]

[0160] TADF materials are materials that have a small difference between the S1 and T1 levels and have the function of converting triplet excitation energy to singlet excitation energy by reverse intersystem crossing. Therefore, triplet excitation energy can be upconverted to singlet excitation energy by a small amount of thermal energy (reverse intersystem crossing), and singlet excitation states can be generated efficiently. In addition, triplet excitation energy can be converted into light emission.

[0161] In addition, exciplexes (also called exciplexes), which form an excited state with two types of substances, have an extremely small difference between the S1 level and the T1 level and function as TADF materials that can convert triplet excitation energy into singlet excitation energy.

[0162] As an index of the T1 level, a phosphorescence spectrum observed at low temperatures (for example, 77 K to 10 K) may be used. For a TADF material, when a tangent line is drawn at the base of the short wavelength side of the fluorescence spectrum, and the energy of the wavelength of the extrapolated line is taken as the S1 level, and a tangent line is drawn at the base of the short wavelength side of the phosphorescence spectrum, and the energy of the wavelength of the extrapolated line is taken as the T1 level, the difference between S1 and T1 is preferably 0.3 eV or less, and more preferably 0.2 eV or less.

[0163] In addition, when a TADF material is used as a light-emitting material, the S1 level of the host material is preferably higher than the S1 level of the TADF material, and the T1 level of the host material is preferably higher than the T1 level of the TADF material.

[0164] As the host material of the light-emitting layer, various carrier transporting materials such as a material having an electron transporting property, a material having a hole transporting property, or the above-mentioned TADF material can be used.

[0165] As a material having hole transport properties, an organic compound having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton is preferable. For example, 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: BPAFLP ... mBPAFLP, 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBANB) , 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 amine skeletons. 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), 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 the first embodiment can also be used.

[0166] Examples of materials having electron transport properties include metal complexes such as bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), as well as organic compounds having a π-electron-deficient heteroaromatic ring skeleton.Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-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, Heterocyclic compounds with polyazole skeletons such as 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]kyi, 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]kyi, and 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI) and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]kyi, are also useful. quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl Examples of the heterocyclic compounds include heterocyclic compounds having a diazine skeleton such as 4,6mDBTP2Pm-II, 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzo[h]quinazoline (abbreviation: 4,8mDBtP2Bqn), and heterocyclic compounds having a pyridine skeleton such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 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 preferred because of their good reliability. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties and contribute to reducing the driving voltage.

[0167] As a TADF material that can be used as a host material, the same TADF materials listed above can be used. When a TADF material is used as a host material, the triplet excitation energy generated in the TADF material is converted to singlet excitation energy by reverse intersystem crossing, and the energy is then transferred to the light-emitting material, thereby increasing the light-emitting efficiency of the light-emitting device. In this case, the TADF material functions as an energy donor, and the light-emitting material functions as an energy acceptor.

[0168] This is very effective when the luminescent material is a fluorescent luminescent material. In this case, in order to obtain high luminous efficiency, the S1 level of the TADF material is preferably higher than the S1 level of the fluorescent luminescent material. In addition, the T1 level of the TADF material is preferably higher than the S1 level of the fluorescent luminescent material. Therefore, the T1 level of the TADF material is preferably higher than the T1 level of the fluorescent luminescent material.

[0169] It is also preferable to use a TADF material that emits light that overlaps with the wavelength of the lowest energy absorption band of the fluorescent material, because this allows for smooth transfer of excitation energy from the TADF material to the fluorescent material, resulting in efficient emission.

[0170] In addition, in order to efficiently generate singlet excitation energy from triplet excitation energy by reverse intersystem crossing, it is preferable that carrier recombination occurs in the TADF material. In addition, it is preferable that the triplet excitation energy generated in the TADF material does not transfer to the triplet excitation energy of the fluorescent material. For this purpose, it is preferable that the fluorescent material has a protective group around the luminophore (skeleton causing light emission) of the fluorescent material. As the protective group, a substituent having no π bond is preferable, and a saturated hydrocarbon is preferable, specifically, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and a trialkylsilyl group having 3 to 10 carbon atoms are mentioned, and it is more preferable that there are a plurality of protective groups. Since a substituent having no π bond has poor function of transporting carriers, the distance between the TADF material and the luminophore of the fluorescent material can be increased without affecting carrier transport or carrier recombination. Here, the luminophore refers to an atomic group (skeleton) causing light emission in the fluorescent material. The luminophore preferably has a skeleton having a π bond, preferably contains an aromatic ring, and preferably has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of the condensed aromatic ring or the condensed heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, and a phenothiazine skeleton. In particular, fluorescent substances having a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, or a naphthobisbenzofuran skeleton are preferred because they have a high fluorescence quantum yield.

[0171] When a fluorescent emitting material is used as the 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 emitting material, it is possible to realize an emitting layer having both good luminous efficiency and durability. As a material having an anthracene skeleton to be used as the host material, a material having 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 injection and transport properties of holes 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 that of 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 that of 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 material 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 material 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: CzPA), and 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: CzPA). Examples of such compounds include 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 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth).In particular, CzPA, cgDBCzPA2mBnfPPA, and PCzPA are preferred choices since they exhibit very good properties.

[0172] The host material may be a mixture of a plurality of substances. 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 weight ratio of the content of the material having a hole transporting property to the material having an electron transporting property may be 1:19 to 19:1 (material having a hole transporting property: material having an electron transporting property). As the material having an electron transporting property in the mixed host material, the organic compound described in embodiment 1 can be preferably used.

[0173] A phosphorescent material can be used as a part of the mixed material. The phosphorescent material can be used as an energy donor that provides excitation energy to a fluorescent material when the fluorescent material is used as a light-emitting material.

[0174] 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.

[0175] At least one of the materials forming the exciplex may be a phosphorescent material, which allows the triplet excitation energy to be efficiently converted into singlet excitation energy by reverse intersystem crossing.

[0176] As a combination of materials that efficiently form an exciplex, it is preferable that the HOMO level of the material having hole transport properties is equal to or higher than the HOMO level of the material having electron transport properties. It is also preferable that the LUMO level of the material having hole transport properties is equal to or higher than the LUMO level of the material having electron transport properties. The LUMO level and HOMO level of the material can be derived from the electrochemical properties (reduction potential and oxidation potential) of the material measured by cyclic voltammetry (CV) measurement.

[0177] The formation of an exciplex can be confirmed, for example, by comparing the emission spectrum of a material having hole transport properties, the emission spectrum of a material having electron transport properties, and the emission spectrum of a mixed film obtained by mixing these materials, and observing the phenomenon that the emission spectrum of the mixed film shifts to a longer wavelength than the emission spectrum of each material (or has a new peak on the longer wavelength side). Alternatively, the formation of an exciplex can be confirmed by comparing the transient photoluminescence (PL) of a material having hole transport properties, the transient PL of a material having electron transport properties, and the transient PL of a mixed film obtained by mixing these materials, and observing the difference in transient response, such as the transient PL lifetime of the mixed film having a longer lifetime component than the transient PL lifetime of each material, or the proportion of delayed components becoming larger. The above-mentioned transient PL may also be read as transient electroluminescence (EL). That is, the formation of an exciplex can also be confirmed by comparing the transient EL of a material having hole transport properties, the transient EL of a material having electron transport properties, and the transient EL of a mixed film obtained by mixing these materials, and observing the difference in transient response.

[0178] 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.

[0179] The electron transport layer 114 has an electron mobility of 1×10 -7 cm 2 / Vs or more 5×10 -5 cm 2 / Vs or less. By lowering the electron transportability in the electron transport layer 114, the amount of electrons injected into the light-emitting layer can be controlled, and the light-emitting layer can be prevented from becoming in an electron excess state. In addition, the electron transport layer preferably contains a material having an electron transportability and an alkali metal or an element, compound, or complex of an alkali metal. These configurations are particularly preferable when the hole injection layer is formed as a composite material, and the HOMO level of the material having hole transportability in the composite material is a substance having a relatively deep HOMO level of -5.7 eV or more and -5.4 eV or less, because the lifetime is improved. In this case, the material having electron transportability preferably has a HOMO level of -6.0 eV or more. In addition, the material having electron transportability is preferably an organic compound having an anthracene skeleton, and more preferably an organic compound having both an anthracene skeleton and a heterocyclic skeleton. The heterocyclic skeleton is preferably a nitrogen-containing 5-membered skeleton or a nitrogen-containing 6-membered skeleton, and particularly preferably has a nitrogen-containing 5-membered skeleton or a nitrogen-containing 6-membered skeleton containing two heteroatoms in the ring, such as a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazine ring, a pyrimidine ring, or a pyridazine ring. In addition, the alkali metal or alkali metal simple substance, compound, or complex preferably contains an 8-hydroxyquinolinato structure. Specifically, for example, 8-hydroxyquinolinato-lithium (abbreviation: Liq) and 8-hydroxyquinolinato-sodium (abbreviation: Naq) can be mentioned. In particular, a complex of a monovalent metal ion, particularly a lithium complex, is preferable, and Liq is more preferable. In addition, when the 8-hydroxyquinolinato structure is contained, a methyl-substituted product (for example, a 2-methyl-substituted product or a 5-methyl-substituted product) can also be used. In the electron transport layer, it is preferable that the alkali metal or the simple substance, compound or complex of the alkali metal has a concentration difference (including the case where the concentration difference is 0) in the thickness direction.

[0180] Between the electron transport layer 114 and the second electrode 102, a layer containing an alkali metal or an alkaline earth metal, such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), or 8-hydroxyquinolinato-lithium (abbreviation: Liq), or a compound thereof may be provided as the electron injection layer 115. The electron injection layer 115 may be a layer made of a substance having an electron transport property containing an alkali metal or an alkaline earth metal or a compound thereof, or an electride. Examples of the electride include a substance in which electrons are added at a high concentration to a mixed oxide of calcium and aluminum.

[0181] Note that a layer containing a fluoride of the alkali metal or alkaline earth metal in a substance having an electron transporting property (preferably an organic compound having a bipyridine skeleton) at a concentration at which the fluoride is in a microcrystalline state or higher (50 wt % or higher) can be used as the electron injection layer 115. Since this layer has a low refractive index, it is possible to provide a light-emitting device with better external quantum efficiency.

[0182] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1B). 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 as a material capable of forming the hole injection layer 111. The P-type layer 117 may be formed by laminating a film containing an acceptor material and a film containing a hole transport material, both of which are materials that form 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 device operates. In addition, since the organic compound according to one embodiment of the present invention is an organic compound having a low refractive index, a light-emitting device having good external quantum efficiency can be obtained by using the organic compound for the P-type layer 117.

[0183] It is preferable that the charge generating layer 116 is provided with either or both of an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117 .

[0184] 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.

[0185] 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)).

[0186] 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.

[0187] 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.

[0188] 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.

[0189] Moreover, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0190] 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.

[0191] 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.

[0192] Next, an embodiment of a light-emitting device having a configuration in which a plurality of light-emitting units are stacked (also called a stacked element or a tandem element) will be described with reference to FIG. 1C. This light-emitting device has a plurality of light-emitting units between an anode and a cathode. One light-emitting unit has a configuration almost similar to that of the EL layer 103 shown in FIG. 1A. In other words, it can be said that the light-emitting device shown in FIG. 1C is a light-emitting device having a plurality of light-emitting units, and the light-emitting device shown in FIG. 1A or FIG. 1B is a light-emitting device having one light-emitting unit.

[0193] In Fig. 1C, 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. 1A, respectively, and the same electrodes as those described in the description of Fig. 1A can be applied. In addition, the first light-emitting unit 511 and the second light-emitting unit 512 may have the same configuration or different configurations.

[0194] 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 anode 501 and cathode 502. That is, when a voltage is applied so that the potential of the anode is higher than the potential of the cathode in FIG. 1C, charge generation layer 513 only needs to inject electrons into first light-emitting unit 511 and inject holes into second light-emitting unit 512.

[0195] The charge generation layer 513 is preferably formed in 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 play the role of the hole injection layer of the light-emitting unit, so that the light-emitting unit does not need to be provided with a hole injection layer.

[0196] 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.

[0197] Although the light-emitting device having two light-emitting units has been described in Fig. 1C, the present invention can be applied to a light-emitting device having three or more light-emitting units stacked in the same manner. By disposing a plurality of light-emitting units between a pair of electrodes and separating them with a charge generating layer 513 as in the light-emitting device according to the present embodiment, it is possible to realize an element that can emit light with high brightness while keeping the current density low and has a long life. In addition, it is possible to realize a light-emitting device that can be driven at a low voltage and consumes low power.

[0198] 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 from the light-emitting device as a whole. For example, in a light-emitting device having two light-emitting units, it is possible to obtain a light-emitting device that emits white light as a whole by obtaining red and green emission colors from the first light-emitting unit and blue emission color from the second light-emitting unit.

[0199] 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.

[0200] (Embodiment 3) In this embodiment, a light emitting apparatus using the light emitting device described in Embodiment 2 will be described.

[0201] In this embodiment, a light-emitting device manufactured using the light-emitting device described in Embodiment 2 will be described with reference to FIG. 2. FIG. 2A is a top view showing the light-emitting device, and FIG. 2B is a cross-sectional view taken along the lines AB and CD in FIG. 2A. 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 the light emission of the light-emitting device. Reference numeral 604 denotes a sealing substrate, 605 denotes a sealant, and the inside surrounded by the sealant 605 defines a space 607.

[0202] 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.

[0203] Next, the cross-sectional structure will be described with reference to Fig. 2B. A driver circuit section and a pixel section are formed on an element substrate 610, and here, a source line driver circuit 601, which is the driver circuit section, and one pixel in a pixel section 602 are shown.

[0204] 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 resin, or the like.

[0205] 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.

[0206] 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.

[0207] 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.

[0208] 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).

[0209] 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.

[0210] By using such a material for the semiconductor layer, fluctuations in electrical characteristics are suppressed, and a highly reliable transistor can be realized.

[0211] 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.

[0212] 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.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] 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 resin 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.

[0217] 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.

[0218] 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 2. Other materials constituting the EL layer 616 may be low molecular weight compounds or high molecular weight compounds (including oligomers and dendrimers).

[0219] 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.).

[0220] Note that a light-emitting device is formed with the first electrode 613, the EL layer 616, and the second electrode 617. The light-emitting device is the light-emitting device described in Embodiment 2. Note that a pixel portion is formed with a plurality of light-emitting devices, but the light-emitting device in this embodiment may include both the light-emitting device described in Embodiment 2 and light-emitting devices having other structures.

[0221] 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 device 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 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.

[0222] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is also preferable that these materials are as impermeable to moisture and oxygen 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 resin, etc.

[0223] 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.

[0224] 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.

[0225] 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.

[0226] 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.

[0227] 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.

[0228] In the above manner, a light-emitting device manufactured using the light-emitting device described in Embodiment 2 can be obtained.

[0229] A light-emitting device with favorable characteristics can be obtained in the light-emitting device of this embodiment because the light-emitting device described in Embodiment 2 is used. Specifically, since the light-emitting device described in Embodiment 2 has favorable emission efficiency, it is possible to provide a light-emitting device with low power consumption.

[0230] Fig. 3 shows an example of a full-color light-emitting device in which a light-emitting device that emits white light is formed and a colored layer (color filter) is provided, etc. Fig. 3A shows a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral section 1042, a pixel section 1040, a driving circuit section 1041, first electrodes 1024W, 1024R, 1024G, 1024B of the light-emitting device, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting device, a sealing substrate 1031, a sealant 1032, etc.

[0231] 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. Light that does not pass through the colored layers is white, and light that passes through the colored layers is red, green, and blue, so that an image can be expressed by four color pixels.

[0232] 3B shows an example in which the colored layers (red colored layer 1034R, green colored layer 1034G, and 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.

[0233] In the light-emitting device described above, the light-emitting device has a structure (bottom emission type) in which light is extracted to 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 to 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 device is formed. Then, 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, as well as other known materials.

[0234] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device 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 configuration as that described for the EL layer 103 in the second embodiment, and has an element structure that can emit white light.

[0235] 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.

[0236] In a top-emission type light-emitting device, a microcavity structure can be suitably applied. A light-emitting device having a microcavity structure can be 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.

[0237] 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.

[0238] 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.

[0239] 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 resonating wavelengths and attenuate the light of non-resonating wavelengths between the reflective electrode and the semi-transmissive / semi-reflective electrode.

[0240] 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.

[0241] In the above configuration, the EL layer may have a structure having multiple light-emitting layers or a structure having a single light-emitting layer. For example, the EL layer may be combined with the above-mentioned tandem light-emitting device configuration, in which multiple EL layers are provided in one light-emitting device with a charge generation layer sandwiched therebetween, and a single or multiple light-emitting layers are formed in each EL layer.

[0242] 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.

[0243] A light-emitting device with favorable characteristics can be obtained in the light-emitting device of this embodiment because the light-emitting device described in Embodiment 2 is used. Specifically, since the light-emitting device described in Embodiment 2 has favorable emission efficiency, it is possible to provide a light-emitting device with low power consumption.

[0244] 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. 5A is a perspective view showing the light emitting device, and FIG. 5B is a cross-sectional view taken along XY in FIG. 5A. 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 side walls of the partition layer 954 have an inclination such that the distance between one side wall and the other side wall becomes narrower as the side walls approach 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 device due to static electricity or the like can be prevented. In addition, the light-emitting device described in Embodiment 2 is used in a passive matrix light-emitting device, and the light-emitting device can be made to be highly reliable or to have low power consumption.

[0245] The light emitting device described above is capable of individually controlling a large number of minute light emitting devices arranged in a matrix, and is therefore a light emitting device that can be suitably used as a display device for displaying images.

[0246] This embodiment mode can be freely combined with other embodiment modes.

[0247] (Embodiment 4) In this embodiment, an example in which the light-emitting device described in Embodiment 2 is used as a lighting device will be described with reference to Fig. 6. Fig. 6B is a top view of the lighting device, and Fig. 6A is a cross-sectional view taken along line ef in Fig. 6B.

[0248] 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 2. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.

[0249] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0250] 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 2, 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.

[0251] A second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in the second embodiment. 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.

[0252] As described above, the lighting device described in this embodiment has a light-emitting device including the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting device has high emission efficiency, the lighting device in this embodiment can have low power consumption.

[0253] The substrate 400 on which the light-emitting device 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, which can absorb moisture and improve reliability.

[0254] 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.

[0255] As described above, the lighting device described in this embodiment uses the light-emitting device described in Embodiment 2 as its EL element, and can be a light-emitting device with low power consumption.

[0256] (Embodiment 5) In this embodiment, an example of an electronic device including the light-emitting device described in Embodiment 2 as a part thereof will be described. The light-emitting device described in Embodiment 2 has good light-emitting efficiency and low power consumption. As a result, the electronic device described in this embodiment can be an electronic device having a light-emitting portion with low power consumption.

[0257] Examples of electronic devices to which the light-emitting devices are applied include television sets (also called televisions or television receivers), computer monitors, 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.

[0258] 7A illustrates an example of a television set. The television set has a display portion 7103 built 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 devices described in Embodiment 2 are arranged in a matrix.

[0259] 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.

[0260] 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.

[0261] 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 devices described in Embodiment 2 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 the 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 the 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 damaged during storage or transportation.

[0262] 7C shows an example of a mobile terminal. The mobile phone 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 devices described in Embodiment 2 are arranged in a matrix.

[0263] 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.

[0264] 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.

[0265] 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 the screen of the display portion 7402.

[0266] 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.

[0267] 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.

[0268] 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.

[0269] 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.

[0270] FIG. 8A is a schematic diagram showing an example of a cleaning robot.

[0271] 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.

[0272] 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.

[0273] 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.

[0274] 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.

[0275] 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.

[0276] The light-emitting device according to one embodiment of the present invention can be used for the display 5101 .

[0277] The robot 2100 shown in FIG. 8B 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.

[0278] 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.

[0279] 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.

[0280] 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.

[0281] 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 for 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.

[0282] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the display portion 5002 .

[0283] 9 shows an example in which the light-emitting device described in Embodiment 2 is used in a desk lamp, which is a lighting device. The desk lamp shown in FIG. 9 has a housing 2001 and a light source 2002, and the lighting device described in Embodiment 3 may be used as the light source 2002.

[0284] FIG. 10 shows an example in which the light-emitting device described in Embodiment 2 is used as an indoor lighting device 3001. Since the light-emitting device described in Embodiment 2 has high emission efficiency, it can be used as a lighting device with low power consumption. In addition, since the light-emitting device described in Embodiment 2 can be made large, it can be used as a large-area lighting device. In addition, since the light-emitting device described in Embodiment 2 is thin, it can be used as a thin lighting device.

[0285] The light-emitting device described in Embodiment 2 can also be mounted on a windshield or dashboard of an automobile. FIG 11 shows an example in which the light-emitting device 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 device described in Embodiment 2.

[0286] A display region 5200 and a display region 5201 are display devices equipped with the light-emitting device described in embodiment 2, which is provided on the windshield of an automobile. The light-emitting device described in embodiment 2 can be a so-called see-through display device in which the opposite side can be seen through by manufacturing 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.

[0287] A display area 5202 is a display device provided on a pillar and equipped with the light-emitting device described in Embodiment 2. By displaying an image from an imaging means provided on the vehicle body in the display area 5202, the view blocked by the pillar can be complemented. Similarly, a display area 5203 provided on the dashboard can complement the view blocked by the vehicle body by displaying an image from an imaging means provided on the outside of 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.

[0288] The display area 5203 can also provide various information by displaying navigation information, a speedometer, a tachometer, a mileage, a fuel gauge, a gear status, air conditioning settings, and the like. 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.

[0289] 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.

[0290] 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.

[0291] 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.

[0292] 13A to 13C show a foldable mobile information terminal 9310. Fig. 13A shows the mobile information terminal 9310 in an unfolded state. Fig. 13B shows the mobile 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. 13C shows the mobile information terminal 9310 in a folded state. The mobile 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.

[0293] 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.

[0294] 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.

[0295] As described above, the light-emitting device having the light-emitting device described in Embodiment 2 has a very wide range of application, and can be applied to electronic devices in a variety of fields. By using the light-emitting device described in Embodiment 2, electronic devices with low power consumption can be obtained. EXAMPLES

[0296] <Synthesis Example 1> In this synthesis example, a method for synthesizing N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: oFBiBnf(6)) shown as structural formula (5-106) in embodiment 1 will be described. The structural formula of oFBiBnf(6) is shown below.

[0297] [ka]

[0298] <Step 1: Synthesis of N-(1,1'-biphenyl-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine> 5.2g (15mmol) of 6-iodo-benzo[b]naphtho[1,2-d]furan, 2.5g (15mmol) of 2-biphenylamine, and 0.12g (0.30mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl were placed in a 200mL three-neck flask equipped with a reflux condenser, and the flask was purged with nitrogen. 2.9g (30mmol) of sodium tert-butoxide and 110mL of xylene were added to the flask, and the flask was degassed under reduced pressure and purged with nitrogen three times each. 86mg (0.15mmol) of bis(bis(dibenzylideneacetone)palladium)(0) was added to the flask, and the mixture was stirred at 110°C for 3 hours. After stirring, insoluble matter was removed from the mixture obtained by suction filtration. Water was added to the obtained filtrate, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water, then washed with saturated saline, and dried over anhydrous magnesium sulfate. The obtained mixture was gravity filtered to remove the anhydrous magnesium sulfate. The obtained filtrate was concentrated to obtain 5.5 g of the desired brown solid in a yield of 95%. The synthesis scheme of step 1 is shown below.

[0299] [ka]

[0300] Nuclear magnetic resonance spectroscopy of the brown solid obtained in step 1 above ( 1 The results of the H-NMR analysis are shown below, which demonstrate that N-(1,1'-biphenyl-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine was obtained in step 1. 1 H NMR (dichloromethane-d2, 300 MHz): δ = 8.52 (d, J = 7.8 Hz, 1H), 7.91 (d, J = 8.7 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.68-7.32 (m, 14H), 7.19 (t, J = 4.2 Hz, 1H), 6.39 (s, 1H)

[0301] <Step 2: Synthesis of N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: oFBiBnf(6))> 2.0g (5.2mmol) of N-(1,1'-biphenyl-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine obtained in step 1 and 1.4g (5.2mmol) of 2-bromo-9,9-dimethylfluorene were placed in a 200mL three-neck flask equipped with a reflux condenser, and the flask was purged with nitrogen. 1.0g (10mmol) of sodium tert-butoxide, 0.30mL of tri-tert-butylphosphine (10wt% hexane solution), and 50mL of xylene were added to the flask, and degassing under reduced pressure and nitrogen replacement were performed three times each. 30mg (0.51mmol) of bis(bis(dibenzylideneacetone)palladium)(0) was added to the flask, and the mixture was stirred at 90°C for 6 hours. After stirring, water was added to the reaction mixture, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water, then washed with saturated saline, and then dried over anhydrous magnesium sulfate. The obtained mixture was gravity filtered to remove the anhydrous magnesium sulfate. The obtained filtrate was concentrated to obtain 2.9 g of a yellow solid containing the target substance in a yield of 96%.

[0302] Of the yellow solid obtained, 2.4 g was purified by train sublimation. The sublimation purification was performed by heating the solid at 200°C for 16 hours under a pressure of 3.6 Pa while flowing argon at 15 mL / min. After sublimation purification, 1.6 g of the target pale yellow solid was obtained with a recovery rate of 66%. The synthesis scheme of step 2 is shown below.

[0303] [ka]

[0304] The obtained solid 1 The numerical data of H-NMR are shown below. 1 The H-NMR charts are shown in Figures 14A and 14B. This shows that oFBiBnf (6) was obtained by this synthesis example. 1 H NMR (dichloromethane-d2, 300 MHz): δ = 8.53 (d, J = 8.4 Hz, 1H), 8.38-8.34 (m, 1H), 7.73 (d, J = 8.4 Hz, 1H), 7.58 (t, J = 6.6 Hz, 2H), 7.48-7.20 (m, 15H), 6.91-6.85 (m, 4H), 6.77 (t, J = 7.5 Hz, 1H), 1.24 (s, 6H)

[0305] Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid thin film of oFBiBnf(6) were measured. The solid thin film was prepared by vacuum deposition on a quartz substrate. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: V-550, manufactured by JASCO Corporation; thin film: U-4100, manufactured by Hitachi High-Technologies Corporation). The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell, and the absorption spectrum of the thin film was calculated by the absorbance (-log 10 The transmittance was calculated from [%T / (100-%R)], where %T is the transmittance and %R is the reflectance. A fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.) was used to measure the emission spectrum.

[0306] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. 15. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown in FIG. 16. From the results in FIG. 15, the toluene solution of oFBiBnf(6) exhibited absorption peaks including shoulder peaks at around 382 nm, 337 nm, and 311 nm, and an emission wavelength peak was observed at 429 nm (excitation wavelength 377 nm). From the results in FIG. 16, the solid thin film of oFBiBnf(6) exhibited absorption peaks including shoulder peaks at around 385 nm, 339 nm, 315 nm, and 248 nm, and an emission wavelength peak was observed at around 445 nm (excitation wavelength 370 nm).

[0307] The HOMO and LUMO levels of oFBiBnf(6) were calculated based on cyclic voltammetry (CV) measurements. The calculation method is shown below.

[0308] 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.

[0309] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.), the auxiliary electrode was a platinum electrode (Pt counter electrode (5 cm) for VC-3, manufactured by BAS Co., Ltd.), and the reference electrode was an Ag / Ag + An electrode (RE7 non-aqueous solvent reference electrode, manufactured by BAS Co., Ltd.) was used. The measurements were carried out at room temperature (20 to 25°C).

[0310] The scan speed during CV measurement 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 embodiment relative to the vacuum level is known to be -4.94 [eV], the HOMO level and the LUMO level can be calculated from the formulas HOMO level [eV] = -4.94-Ea and LUMO level [eV] = -4.94-Ec, respectively.

[0311] In addition, 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 1st cycle to examine the electrical stability of the compound.

[0312] As a result, the HOMO level of oFBiBnf(6) was found to be -5.49 eV based on the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of oFBiBnf(6) was found to be -2.36 eV based on the measurement of the reduction potential Ec [V]. In addition, the results of repeated measurements of the oxidation-reduction wave showed that the peak intensity was maintained at 92% in the Ea measurement and 95% in the Ec measurement when comparing the waveforms after the first cycle and 100 cycles, confirming that oFBiBnf(6) has very good resistance to oxidation and reduction.

[0313] Differential scanning calorimetry (DSC) of oFBiBnf(6) was also performed using a Pyris1 DSC manufactured by PerkinElmer. Differential scanning calorimetry was performed by heating the material from -10°C to 270°C at a heating rate of 40°C / min, holding the material at the same temperature for 1 minute, and then cooling it to -10°C at a heating rate of 100°C / min twice in succession. The results of the second cycle of DSC measurement revealed that the glass transition point of oFBiBnf(6) was 119°C, indicating that it is a material with extremely high heat resistance.

[0314] In addition, we performed a differential thermal analysis of oFBiBnf(6). A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, a heating rate of 10°C / min, and a nitrogen gas flow (flow rate 200 mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement was 366°C, indicating that the substance has good sublimation properties.

[0328] The above results demonstrate that the organic compound of one embodiment of the present invention has both high heat resistance and favorable sublimation property, and can provide an organic optical device (light-emitting device and light-receiving device) with high heat resistance and can increase the productivity of device fabrication. EXAMPLES

[0315] <Synthesis Example 2> In this synthesis example, a method for synthesizing N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: oFBi(4)Bnf(6)) shown as structural formula (5-107) in embodiment 1 will be described. The structural formula of oFBi(4)Bnf(6) is shown below.

[0316] [ka]

[0317] <Step 1: Synthesis of N-(1,1'-biphenyl-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine> The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1 in Example 1.

[0318] <Step 2: Synthesis of N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: oFBi(4)Bnf(6))> 2.0g (5.2mmol) of N-(1,1'-biphenyl-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine obtained in step 1 and 1.4g (5.2mmol) of 4-bromo-9-dimethylfluorene were placed in a 200mL three-neck flask equipped with a reflux condenser, and the flask was replaced with nitrogen. 1.0g (10mmol) of sodium tert-butoxide, 0.30mL of tri-tert-butylphosphine (10wt% hexane solution), and 50mL of xylene were added to the flask, and reduced pressure degassing and nitrogen replacement were performed three times each. 30mg (0.51mmol) of bis(bis(dibenzylideneacetone)palladium)(0) was added to the flask, and the mixture was stirred at 80°C for 16 hours. After stirring, water was added to the reaction mixture, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water, then washed with saturated saline, and then dried over anhydrous magnesium sulfate. The obtained mixture was gravity filtered to remove the anhydrous magnesium sulfate. The obtained filtrate was concentrated to obtain 2.9 g of a yellow solid containing the target substance. This yellow solid was purified by recrystallization (toluene / hexane) to obtain 1.4 g of the target white solid in a yield of 47%.

[0319] The resulting 1.4 g of white solid was purified by train sublimation. The sublimation purification was performed by heating the white solid at 205°C for 15 hours under a pressure of 3.6 Pa while flowing argon at 15 mL / min. After sublimation purification, 1.1 g of the target white solid was obtained with a recovery rate of 78%. The synthesis scheme is shown below.

[0320] [ka]

[0321] The obtained solid 1 The numerical data of H-NMR are shown below. 1 The H-NMR charts are shown in Figures 17A and 17B. This shows that oFBi(4)Bnf(6) was obtained by this synthesis example. 1H NMR (dichloromethane-d2, 300 MHz): δ = 8.57 (d, J = 7.8 Hz, 1H), 8.50-8.44 (m, 1H), 7.66-7.50 (m, 5H), 7.42-7.03 (m, 12H), 6.97 (t, J = 7.5 Hz, 1H), 6.83 (d, J = 7.5 Hz, 1H), 6.65-6.55 (m, 4H), 1.29 (s, 6H)

[0322] Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid thin film of oFBi(4)Bnf(6) were measured. The measurement method and the measurement device were the same as those in Example 1, so repeated descriptions will be omitted.

[0323] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 18. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown in Figure 19. From the results in Figure 18, the toluene solution of oFBi(4)Bnf(6) showed absorption peaks including shoulder peaks near 357 nm, 328 nm, and 301 nm, and an emission wavelength peak was observed at 405 nm (excitation wavelength 353 nm). From the results in Figure 19, the solid thin film of oFBi(4)Bnf(6) showed absorption peaks including shoulder peaks near 360 nm, 332 nm, 304 nm, and 282 nm, and an emission wavelength peak was observed near 423 nm (excitation wavelength 360 nm).

[0324] The HOMO and LUMO levels of oFBi(4)Bnf(6) were calculated based on cyclic voltammetry (CV) measurements. The calculation method, measurement method, and measurement device were the same as in Example 1, so repeated descriptions will be omitted.

[0325] As a result, the HOMO level of oFBi(4)Bnf(6) was found to be -5.64 eV and the LUMO level to be -2.32 eV. In addition, when the waveforms after the 1st and 100th cycles of repeated measurements of the oxidation-reduction wave were compared, the peak intensity was found to be 79% in the Ea measurement and 97% in the Ec measurement, confirming that oFBi(4)Bnf(6) has very good resistance to oxidation and reduction.

[0326] Differential scanning calorimetry (DSC) of oFBi(4)Bnf(6) was also performed using a Pyris1 DSC manufactured by PerkinElmer. The differential scanning calorimetry was performed by heating the material from -10°C to 253°C at a heating rate of 40°C / min, holding the material at the same temperature for 1 minute, and then cooling it to -10°C at a heating rate of 100°C / min twice in succession. The results of the second cycle of DSC measurement revealed that the glass transition point of oFBi(4)Bnf(6) was 114°C, indicating that the material has extremely high heat resistance.

[0327] In addition, we performed differential thermal analysis of oFBi(4)Bnf(6). A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, heating rate of 10°C / min, and nitrogen flow (flow rate 200mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement was 343°C, indicating that the substance has good sublimation properties.

[0328] The above results demonstrate that the organic compound of one embodiment of the present invention has both high heat resistance and favorable sublimation property, and can provide an organic optical device (light-emitting device and light-receiving device) with high heat resistance and can increase the productivity of device fabrication. EXAMPLES

[0329] <Synthesis Example 3> In this synthesis example, a method for synthesizing N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: FBi(4)Bnf(6)) shown as structural formula (5-59) in embodiment 1 will be described. The structural formula of FBi(4)Bnf(6) is shown below.

[0330] [ka]

[0331] <Step 1: Synthesis of N-(9,9-dimethyl-9H-fluoren-4-yl) t-butoxycarbonylamine> 5.4g (20mmol) of 4-bromo-9,9-dimethyl-9H-fluorene, 2.3g (20mmol) of tert-butyl carbamate, 0.23g (0.40mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (abbreviated as Xantphos), and 13g (40mmol) of cesium carbonate were placed in a 200mL three-neck flask equipped with a reflux condenser, and the flask was replaced with nitrogen. 100mL of anhydrous 1,4-dioxane was added to the flask, and the mixture was degassed under reduced pressure. After placing the flask under a nitrogen stream, the mixture was stirred at 60°C, 55mg (0.20mmol) of palladium(II) acetate was added, and the mixture was stirred at 80°C for 3 hours. After stirring, the precipitate was removed by suction filtration, and the mixture was washed three times with about 100 mL of water using a 500 mL separatory funnel. The aqueous layer obtained by washing was extracted three times with about 200 mL of toluene, and the obtained extract and organic layer were combined and washed once with about 300 mL of saturated saline. Anhydrous magnesium sulfate was added to the obtained organic layer, and the mixture was left for 1 hour, and then naturally filtered. The obtained filtrate was concentrated to obtain a compound, which was purified by silica gel column chromatography (developing solvent: toluene: ethyl acetate = 9:1), and 5.5 g of the target white solid was obtained in a yield of 88%. The synthesis scheme of step 1 is shown below.

[0332] [ka]

[0333] <Step 2: Synthesis of 9,9-dimethyl-9H-fluoren-4-amine> 5.5g (18mmol) of N-(9,9-dimethyl-9H-fluoren-4-yl) t-butoxycarbonylamine obtained in step 1 and 100mL of dichloromethane were placed in a 1000mL eggplant flask, and the flask was placed under a nitrogen stream. 5.2mL (8.1g, 71mmol) of trifluoroacetic acid was added dropwise to this solution from a dropping funnel over 5 minutes, and the mixture was stirred at room temperature for about 16 hours. After stirring, the eggplant flask was placed in an ice bath, and 100mL of potassium hydroxide solution (0.7mmol) was added to neutralize. The resulting mixture was separated into an organic phase and an aqueous phase using a 500mL separatory funnel, and the organic phase was washed three times with about 100mL of water. The water used for washing was extracted three times with 200mL of toluene, and the resulting extract and organic phase were combined and washed with about 200mL of saturated saline. After washing, anhydrous magnesium sulfate was added to the organic phase obtained, and the mixture was left for 1 hour, then gravity filtered and the filtrate obtained was concentrated. The obtained compound was dried in a vacuum to obtain 3.2 g of the desired white solid in 86% yield. The synthesis scheme of step 2 is shown below.

[0334] [ka]

[0335] <Step 3: Synthesis of N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-6-amine> 1.5g (7.2mmol) of 9,9-dimethyl-9H-fluoren-4-amine obtained in step 2, 2.5g (7.2mmol) of 6-iodobenzo[b]naphtho[1,2-d]furan, 0.18g (0.4mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (sphos), and 1.5g (15mmol) of sodium t-butoxide were placed in a 200mL three-neck flask equipped with a reflux condenser, and the flask was replaced with nitrogen. 40mL of toluene was added to the flask, and the flask was degassed under reduced pressure, and then the flask was placed under a nitrogen stream. This mixture was stirred at 60°C, and 0.11g (0.20mmol) of bis(bis(dibenzylideneacetone)palladium)(0) was added to the flask at the same temperature, and the mixture was stirred at 80°C for 3 hours. After stirring, the resulting mixture was washed three times with about 100 mL of water using a 1 L separatory funnel. The water used for washing was extracted three times with about 100 mL of toluene, and the resulting extract and organic phase were combined and washed with about 200 mL of saturated saline. Anhydrous magnesium sulfate was added to the resulting organic phase and left for 1 hour, after which the mixture was naturally filtered, and the resulting filtrate was concentrated to obtain 3.5 g of a dark brown compound. The resulting compound was purified by silica gel column chromatography (developing solvent: hexane: toluene = 2: 1), obtaining 1.8 g of the target product in a yield of 59%. The synthesis scheme of step 3 is shown below.

[0336] [ka]

[0337] <Step 4: Synthesis of N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: FBi(4)Bnf(6))> 1.8g (4.1mmol) of N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-6-amine obtained in step 3 and 0.96g (4.1mmol) of 4-bromobiphenyl were placed in a 200mL three-neck flask equipped with a reflux condenser, and the flask was purged with nitrogen. 0.80g (8.3mmol) of sodium tert-butoxide, 0.30mL of tri-tert-butylphosphine (10wt% hexane solution), and 25mL of xylene were added to the flask, and vacuum degassing and nitrogen replacement were performed three times each. 24mg (0.41mmol) of bis(bis(dibenzylideneacetone)palladium)(0) was added to the flask, and the mixture was stirred at 80°C for 4 hours. After stirring, water was added to the reaction mixture, and the aqueous layer was extracted with toluene. The obtained organic layer was washed twice with water, then washed with saturated saline, and then dried over anhydrous magnesium sulfate. The obtained mixture was gravity filtered to remove the anhydrous magnesium sulfate. The obtained filtrate was concentrated to obtain 3.4 g of a pale yellow solid. The obtained pale yellow solid was purified by high performance liquid chromatography (HPLC) (mobile phase: chloroform) to obtain 2.2 g of the target white solid in a yield of 93%.

[0338] Of the resulting white solid, 1.8 g was purified by train sublimation. The sublimation purification was carried out by heating the solid at 230°C for 16 hours under a pressure of 3.1 Pa while flowing argon at 15 mL / min. After sublimation purification, 1.2 g of the target white solid was obtained with a recovery rate of 66%. The synthesis scheme of step 4 is shown below.

[0339] [ka]

[0340] The obtained solid 1 The numerical data of H-NMR are shown below. 1 The H-NMR charts are shown in Figures 20A and 20B. This shows that FBi(4)Bnf(6) was obtained in this synthesis example. 1H NMR (dichloromethane-d2, 300 MHz): δ = 8.61 (d, J = 8.4 Hz, 1H), 8.45-8.42 (m, 1H), 7.84 (d, J = 7.8 Hz, 1H), 7.78 (d, J = 8.1 Hz, 1H), 7.66-7.18 (m, 18H), 7.03-6.96 (m, 3H), 1.57 (s, 6H)

[0341] Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid thin film of FBi(4)Bnf(6) were measured. The measurement method and the measurement device were the same as those in Example 1, so repeated descriptions will be omitted.

[0342] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 21. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown in Figure 22. From the results in Figure 21, the toluene solution of FBi(4)Bnf(6) showed absorption peaks including shoulder peaks near 371 nm, 336 nm, 307 nm, and 283 nm, and an emission wavelength peak was observed at 428 nm (excitation wavelength 370 nm). From the results in Figure 22, the solid thin film of FBi(4)Bnf(6) showed absorption peaks including shoulder peaks near 374 nm, 337 nm, 309 nm, and 285 nm, and an emission wavelength peak was observed near 428 nm (excitation wavelength 350 nm).

[0343] The HOMO level and LUMO level of FBi(4)Bnf(6) were calculated based on cyclic voltammetry (CV) measurements. The calculation method is shown below. The calculation method, measurement method, and measurement device are the same as those in Example 1, so repeated descriptions will be omitted.

[0344] As a result, the HOMO level of FBi(4)Bnf(6) was found to be -5.64 eV and the LUMO level to be -2.40 eV. In addition, when the waveforms after the 1st and 100th cycles were compared in repeated measurements of the oxidation-reduction wave, 79% of the peak intensity was maintained in the Ea measurement, and 93% of the peak intensity was maintained in the Ec measurement, confirming that FBi(4)Bnf(6) has good resistance to oxidation and reduction.

[0345] Differential scanning calorimetry (DSC) of FBi(4)Bnf(6) was also performed using a Pyris1 DSC manufactured by PerkinElmer. Differential scanning calorimetry was performed by heating the material from -10°C to 280°C at a heating rate of 40°C / min, holding the material at the same temperature for 1 minute, and then cooling it to -10°C at a heating rate of 100°C / min twice in succession. The results of the second cycle of DSC measurement revealed that the glass transition point of FBi(4)Bnf(6) was 134°C, indicating that the material has extremely high heat resistance.

[0346] In addition, differential thermal analysis (Thermogravimetry-Differential Thermal Analysis) of FBi(4) and Bnf(6) was performed. A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, heating rate of 10°C / min, and nitrogen flow (flow rate 200mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement was 390°C, indicating that the substance has good sublimation properties.

[0328] The above results demonstrate that the organic compound of one embodiment of the present invention has both high heat resistance and favorable sublimation property, and can provide an organic optical device (light-emitting device and light-receiving device) with high heat resistance and can increase the productivity of device fabrication. EXAMPLES

[0347] <Synthesis Example 4> In this synthesis example, a method for synthesizing N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: FBiBnf(6)) shown as structural formula (5-58) in embodiment 1 will be described. The structural formula of FBiBnf(6) is shown below.

[0348] [ka]

[0349] <Step 1: Synthesis of N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine> 2.1g (10mmol) of 9,9-dimethyl-9H-fluoren-2-amine, 3.4g (10mmol) of 6-iodobenzo[b]naphtho[1,2-d]furan, 0.84mg (0.2mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (sphos), and 2.0g (20mmol) of sodium t-butoxide were placed in a 200mL three-neck flask equipped with a reflux condenser, and the flask was replaced with nitrogen. 50mL of toluene was added to the flask, and after degassing under reduced pressure, the flask was placed under a nitrogen stream. This mixture was stirred at 60°C, and 60mg (0.11mmol) of bis(bis(dibenzylideneacetone)palladium)(0) was added to the flask at the same temperature, and then stirred at 80°C for 7 hours. After stirring, 600mL of toluene was added to the resulting mixture, and the mixture was heated and stirred at 100°C. This mixture was filtered at the same temperature through alumina, Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 066-05265), and Celite (Wako Pure Chemical Industries, Ltd., catalog number: 537-02305). The filtrate was concentrated to obtain a solid, which was then recrystallized from 300 mL of ethanol to obtain 2.5 g of the desired white solid in a yield of 58%. The synthesis scheme for step 1 is shown below.

[0350] [ka]

[0351] <Step 2: Synthesis of N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: FBiBnf(6))> 1.1g (2.5mmol) of N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine obtained in step 1, 0.58g (2.5mmol) of 4-bromobiphenyl, 0.86mg (0.2mmol) of 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tBuxphos), and 0.52g (5.0mmol) of t-butoxysodium were placed in a 200mL three-neck flask equipped with a reflux condenser, and the flask was replaced with nitrogen. 25mL of xylene was added to the flask, and the flask was degassed under reduced pressure, and then the flask was placed under a nitrogen stream. The mixture was stirred at 80°C, and 62 mg (0.11 mmol) of bis(bis(dibenzylideneacetone)palladium)(0) was added to the flask at the same temperature, followed by stirring at 110°C for 5 hours. After stirring, 600 mL of toluene was added to the mixture obtained and heated and stirred at 100°C. The mixture was filtered at the same temperature through alumina, Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 066-05265), and Celite (Wako Pure Chemical Industries, Ltd., catalog number: 537-02305). The filtrate was concentrated to obtain a solid, which was purified by silica gel column chromatography (developing solvent: hexane:toluene = 1:1) and then by high performance liquid chromatography (developing solvent: chloroform), yielding 0.96 g of the target pale yellow solid in 66% yield.

[0352] The pale yellow solid (0.96 g) obtained was purified by train sublimation. The sublimation purification was performed by heating the pale yellow solid at 270°C for 16 hours under a pressure of 2.5 Pa while flowing argon at 15 mL / min. After sublimation purification, 0.80 g of the target white solid was obtained with a recovery rate of 84%. The synthesis scheme of step 2 is shown below.

[0353] [ka]

[0354] The obtained solid 1 The numerical data of H-NMR are shown below. 1 The H-NMR charts are shown in Figures 23A and 23B. This shows that FBiBnf (6) was obtained by this synthesis example.

[0355] 1 H NMR (dichloromethane-d2,300MHz): δ=8.63(d, J=8.0Hz, 1H), 8.43(dd, J1=6.8Hz, J2=1.5Hz, 1H), 7.86(d, J=8.0Hz, 1H), 7.71(s, 1H), 7.69-7.59( m, 5H), 7.53(d, J=8.5Hz, 2H), 7.52-7.38(m, 7H), 7.32-7.24(m, 4H), 7.21(d, J=9.0Hz, 2H), 7.13(dd, J1=8.3Hz, J2=1.5Hz, 1H)1.37(s, 6H)

[0356] Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid thin film of FBiBnf(6) were measured. The measurement method and the measurement device were the same as those in Example 1, so repeated descriptions will be omitted.

[0357] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in FIG. 24. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown in FIG. 25. From the results in FIG. 24, the toluene solution of FBiBnf(6) exhibited absorption peaks including shoulder peaks at around 389 nm, 352 nm, 340 nm, and 313 nm, and an emission wavelength peak was observed at 438 nm (excitation wavelength 360 nm). From the results in FIG. 25, the solid thin film of FBiBnf(6) exhibited absorption peaks including shoulder peaks at around 396 nm, 358 nm, 341 nm, and 316 nm, and an emission wavelength peak was observed at around 452 nm (excitation wavelength 365 nm).

[0358] The HOMO level and LUMO level of FBiBnf(6) were calculated based on cyclic voltammetry (CV) measurement. The calculation method is shown below. The calculation method, measurement method, and measurement device are the same as those in Example 1, so repeated descriptions will be omitted.

[0359] As a result, the HOMO level of FBiBnf(6) was found to be -5.48 eV and the LUMO level was found to be -2.41 eV. In addition, when the waveforms after the 1st and 100th cycles were compared in repeated measurements of the oxidation-reduction wave, 87% of the peak intensity was maintained in the Ea measurement and 97% in the Ec measurement, confirming that FBiBnf(6) has good resistance to oxidation and reduction.

[0360] Differential scanning calorimetry (DSC) of FBiBnf(6) was also performed using a Pyris1 DSC manufactured by PerkinElmer. The differential scanning calorimetry was performed by heating the material from -10°C to 300°C at a heating rate of 40°C / min, holding the material at the same temperature for 1 minute, and then cooling it to -10°C at a heating rate of 100°C / min twice in succession. The results of the second cycle of DSC measurement revealed that the glass transition point of FBiBnf(6) was 128°C, indicating that the material has extremely high heat resistance.

[0361] In addition, differential thermal analysis (Thermogravimetry-Differential Thermal Analysis) of FBiBnf(6) was performed. A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, heating rate of 10 °C / min, and nitrogen flow (flow rate 200 mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement was 352 °C, indicating that the substance has good sublimation properties.

[0328] The above results demonstrate that the organic compound of one embodiment of the present invention has both high heat resistance and favorable sublimation property, and can provide an organic optical device (light-emitting device and light-receiving device) with high heat resistance and can increase the productivity of device fabrication. EXAMPLES

[0362] Example 1 In this example, a light-emitting device according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of organic compounds used in this example are shown below.

[0363] [ka]

[0364] (Method of fabricating light-emitting device 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.

[0365] Next, as a pretreatment for forming a light-emitting device 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.

[0366] 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.

[0367] Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 is formed faces downward. On the first electrode 101, N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: FBiBnf(6)) represented by the above structural formula (i) and ALD-MP001Q (Bunseki Kobo Co., Ltd., material serial number: 1S20180314) are co-deposited to a thickness of 10 nm by a deposition method using resistance heating so that the weight ratio is 1:0.1 (=FBiBnf(6):ALD-MP001Q) to form a hole injection layer 111.

[0368] Next, FBiBnf(6) was deposited on the hole injection layer 111 to a thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0369] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iii) and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03) represented by the above structural formula (iv) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6BnfAPrn-03) to form the light-emitting layer 113.

[0370] Thereafter, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (v) was formed to a thickness of 15 nm on the light-emitting layer 113, and then 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0371] 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 device 1 of this embodiment.

[0372] (Method of producing comparative light-emitting device 1) Comparative light-emitting device 1 was prepared in the same manner as light-emitting device 1, except that FBiBnf(6) in light-emitting device 1 was replaced with N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf) represented by the above structural formula (vii).

[0373] (Method of manufacturing light-emitting device 2) Light-emitting device 2 was fabricated in the same manner as light-emitting device 1, except that the thickness of FBiBnf(6) in the hole-transporting layer of light-emitting device 1 was changed from 20 nm to 120 nm.

[0374] (Method of producing comparative light-emitting device 2) Comparative light-emitting device 2 was prepared in the same manner as light-emitting device 2, except that FBiBnf(6) in light-emitting device 2 was changed to BBABnf.

[0375] The element structure of the above light emitting device is summarized in the table below.

[0376] [Table 1]

[0377] [Table 2]

[0378] The above light-emitting device was sealed with a glass substrate in a glove box with a nitrogen atmosphere to prevent the light-emitting device from being 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 were measured.

[0379] The luminance-current density characteristics of light-emitting device 1 and comparative light-emitting device 1 are shown in Fig. 26, the current efficiency-luminance characteristics in Fig. 27, the luminance-voltage characteristics in Fig. 28, the current-voltage characteristics in Fig. 29, the external quantum efficiency-luminance characteristics in Fig. 30, and the emission spectra in Fig. 31. The luminance-current density characteristics of light-emitting device 2 and comparative light-emitting device 2 are shown in Fig. 32, the current efficiency-luminance characteristics in Fig. 33, the luminance-voltage characteristics in Fig. 34, the current-voltage characteristics in Fig. 35, the external quantum efficiency-luminance characteristics in Fig. 36, and the emission spectra in Fig. 37. In addition, at 1000 cd / m of each light-emitting device, 2 The main characteristics of the vicinity are as follows:

[0380] [Table 3]

[0381] [Table 4]

[0382] 26 to 31, it was found that the light-emitting device 1 of one embodiment of the present invention is an EL device with good light-emitting efficiency. In addition, the light-emitting device 2 and the comparative light-emitting device 2 are elements in which FBiBnf(6) and BBABnf in the hole-transport layer are thickened to 120 nm, but it was found that the light-emitting device 2 of one embodiment of the present invention is an element in which the voltage increase is small even when the film is thickened. This shows that FBiBnf(6), which is an organic compound of one embodiment of the present invention, is an organic compound with good carrier-transport properties, particularly hole-transport properties.

[0383] In addition, the current density is 50mA / cm 2Graphs showing changes in luminance with respect to drive time in the above-mentioned embodiment are shown in Fig. 38 and Fig. 39. As shown in Fig. 38 and Fig. 39, it was found that light-emitting device 1 and light-emitting device 2, which are light-emitting devices according to an embodiment of the present invention, are light-emitting devices with good lifetimes, similar to comparative light-emitting device 1 and comparative light-emitting device 2. EXAMPLES

[0384] Example 1 In this example, a light-emitting device according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of organic compounds used in this example are shown below.

[0385] [ka]

[0386] (Method of manufacturing light-emitting device 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.

[0387] Next, as a pretreatment for forming a light-emitting device 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.

[0388] 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.

[0389] Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 is formed faces downward. On the first electrode 101, N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: oFBiBnf(6)) represented by the above structural formula (viii) and ALD-MP001Q (Bunseki Kobo Co., Ltd., material serial number: 1S20180314) are co-deposited to a thickness of 10 nm by a deposition method using resistance heating so that the weight ratio is 1:0.1 (=oFBiBnf(6):ALD-MP001Q) to form a hole injection layer 111.

[0390] Next, oFBiBnf(6) was deposited on the hole injection layer 111 to a thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0391] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iii) and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03) represented by the above structural formula (iv) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=cgDBCzPA:1,6BnfAPrn-03) to form the light-emitting layer 113.

[0392] Thereafter, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (v) was formed to a thickness of 15 nm on the light-emitting layer 113, and then 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0393] 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 device 3 of this embodiment.

[0394] (Method of producing comparative light-emitting device 3) Comparative light-emitting device 3 was prepared in the same manner as light-emitting device 3, except that oFBiBnf(6) in light-emitting device 3 was replaced with N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf) represented by the above structural formula (vii).

[0395] (Method of manufacturing light-emitting device 4) Light-emitting device 4 was fabricated in the same manner as light-emitting device 3, except that the thickness of the oFBiBnf(6) in the hole-transporting layer of light-emitting device 3 was changed from 20 nm to 120 nm.

[0396] (Method of producing comparative light-emitting device 4) Comparative light-emitting device 4 was fabricated in the same manner as light-emitting device 4, except that oFBiBnf(6) in light-emitting device 4 was changed to BBABnf.

[0397] The element structure of the above light emitting device is summarized in the table below.

[0398] [Table 5]

[0399] [Table 6]

[0400] The above light-emitting device was sealed with a glass substrate in a glove box with a nitrogen atmosphere to prevent the light-emitting device from being 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 were measured.

[0401] The luminance-current density characteristics of light-emitting device 3 and comparative light-emitting device 3 are shown in Fig. 40, the current efficiency-luminance characteristics in Fig. 41, the luminance-voltage characteristics in Fig. 42, the current-voltage characteristics in Fig. 43, the external quantum efficiency-luminance characteristics in Fig. 44, and the emission spectra in Fig. 45. The luminance-current density characteristics of light-emitting device 4 and comparative light-emitting device 4 are shown in Fig. 46, the current efficiency-luminance characteristics in Fig. 47, the luminance-voltage characteristics in Fig. 48, the current-voltage characteristics in Fig. 49, the external quantum efficiency-luminance characteristics in Fig. 50, and the emission spectra in Fig. 51. In addition, at 1000 cd / m of each light-emitting device, 2 The main characteristics of the vicinity are as follows:

[0402] [Table 7]

[0403] [Table 8]

[0404] 40 to 45 show that the light-emitting device 3 of one embodiment of the present invention is an EL device with good light-emitting efficiency. 48 and 49 show that the light-emitting device 4 and the comparative light-emitting device 4 are elements in which oFBiBnf(6) and BBABnf in the hole-transport layer are thickened to 120 nm, but the light-emitting device 4 of one embodiment of the present invention is an element in which the voltage increase is small even when the film is thickened. This shows that oFBiBnf(6), which is an organic compound of one embodiment of the present invention, is an organic compound with good carrier-transport properties, particularly hole-transport properties.

[0405] In addition, the current density is 50mA / cm 2Graphs showing changes in luminance with respect to drive time in the above-mentioned embodiment are shown in Fig. 52 and Fig. 53. As shown in Fig. 52 and Fig. 53, it was found that light-emitting device 3 and light-emitting device 4, which are light-emitting devices according to one embodiment of the present invention, are light-emitting devices with good lifetimes, similar to comparative light-emitting device 3 and comparative light-emitting device 4. EXAMPLES

[0406] Example 1 In this example, a light-emitting device according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of organic compounds used in this example are shown below.

[0407] [ka]

[0408] (Method of Manufacturing Light-Emitting Device 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.

[0409] Next, as a pretreatment for forming a light-emitting device 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.

[0410] 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.

[0411] Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 is formed faces downward. On the first electrode 101, N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: oFBi(4)Bnf(6)) represented by the above structural formula (ix) and ALD-MP001Q (Breakdown Workshop Co., Ltd., material serial number: 1S20180314) are co-deposited to a thickness of 10 nm by a deposition method using resistance heating so that the weight ratio is 1:0.1 (=oFBi(4)Bnf(6):ALD-MP001Q) to form a hole injection layer 111.

[0412] Next, oFBi(4)Bnf(6) was deposited on the hole injection layer 111 to a thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0413] Next, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iii) and 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02) represented by the above structural formula (x) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.015 (=cgDBCzPA:3,10PCA2Nbf(IV)-02) to form the light-emitting layer 113.

[0414] Thereafter, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (v) was formed to a thickness of 15 nm on the light-emitting layer 113, and then 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0415] 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 device 5 of this embodiment.

[0416] (Method of manufacturing light-emitting device 6) Light-emitting device 6 was fabricated in the same manner as light-emitting device 5, except that oFBi(4)Bnf(6) in light-emitting device 5 was changed to N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: FBi(4)Bnf(6)) represented by the above structural formula (xi).

[0417] The element structure of the above light emitting device is summarized in the table below.

[0418] [Table 9]

[0419] The above light-emitting device was sealed with a glass substrate in a glove box with a nitrogen atmosphere to prevent the light-emitting device from being 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 were measured.

[0420] The luminance-current density characteristics of light-emitting device 5 and light-emitting device 6 are shown in Fig. 54, the current efficiency-luminance characteristics in Fig. 55, the luminance-voltage characteristics in Fig. 56, the current-voltage characteristics in Fig. 57, the external quantum efficiency-luminance characteristics in Fig. 58, and the emission spectrum in Fig. 59. 2 The main characteristics of the vicinity are as follows:

[0421] [Table 10]

[0422] 54 to 59 show that the light-emitting devices 5 and 6 of one embodiment of the present invention are EL devices with high emission efficiency. EXAMPLES

[0423] <Synthesis Example 5> In this synthesis example, a method for synthesizing N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: FBiBnf(8)) shown as structural formula (5-55) in embodiment 1 will be described. The structural formula of FBiBnf(8) is shown below.

[0424] [ka]

[0425] <Step 1: Synthesis of FBiBnf(8)> 1.6g (6.3mmol) of 8-chloro-benzo[b]naphtho[1,2-d]furan, 2.3g (6.3mmol) of 2-(4-biphenylyl)amino-9,9-dimethylfluorene, 1.2g (13mol) of sodium tert-butoxide, 44mg (0.13mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (commonly known as cBRIDP(regR)), and 30mL of xylene were placed in a 500mL three-neck flask equipped with a reflux condenser, and the flask was purged with nitrogen. 36mg (63μmol) of bis(dibenzylideneacetone)palladium(0) was added to the flask, and the mixture was heated at 160℃ for 6 hours.

[0426] Toluene and water were added to the resulting mixture, and the organic layer and the aqueous layer were separated. The resulting organic layer was washed twice with water, and then washed with saturated saline. The organic layer was dried over magnesium sulfate. The resulting mixture was gravity filtered to remove the magnesium sulfate. The resulting filtrate was concentrated and dried to obtain 4.3 g of a dark brown solid. The resulting solid was purified by silica gel chromatography (hexane:toluene = 3:1) to obtain 2.2 g of a white solid in 60% yield. The synthesis scheme of step 1 is shown below.

[0427] [ka]

[0428] The resulting white solid (2.0 g) was purified by train sublimation. The purification was carried out by heating the solid at 260°C for 16 hours under a pressure of 5.6 Pa while flowing argon at 10 mL / min. After the purification, 1.6 g of the target white solid was obtained with a recovery rate of 80%.

[0429] The obtained solid 1 The numerical data of H-NMR are shown below. 1 The H-NMR chart is shown in Figure 60. Note that Figure 60B is a graph showing an enlarged range from 7.0 ppm to 9.0 ppm in Figure 60A. This shows that FBiBnf(8) was obtained.

[0430] 1 H NMR (Chloroform-d, 300MHz): δ=8.65(d, J=8.7Hz, 1H), 8.23(d, J=6.9Hz, 1H), 8.00(d, J=8.1Hz, 1H), 7.84(d, J=9.3Hz, 1H), 7.74 (t, J=8.4Hz, 1H), 7.65(d, J=6.9Hz, 1H), 7.63-7.28(m, 16H), 7.21(d, J=8.7Hz, 2H), 7.14(dd, J=4.2, 2.1Hz, 1H), 1.39(s, 6H)

[0431] Next, we measured the UV-visible absorption spectrum (hereinafter simply referred to as the “absorption spectrum”) and emission spectrum of the toluene solution and solid thin film of FBiBnf(8). The solid thin film was prepared on a quartz substrate by vacuum deposition.

[0432] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: V-550, manufactured by JASCO Corporation; thin film: U-4100, manufactured by Hitachi High-Technologies Corporation). The absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell, and the absorption spectrum of the thin film was calculated by the absorbance (-log 10 The transmittance was calculated from [%T / (100-%R)], where %T is the transmittance and %R is the reflectance. A fluorometer (JASCO FP-8600) was used to measure the emission spectrum.

[0433] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 61. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown in Figure 62. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. From the results in Figure 61, the toluene solution of FBiBnf(8) showed absorption peaks near 357 nm and 339 nm, and an emission wavelength peak was observed near 421 nm (excitation wavelength 350 nm). From the results in Figure 62, the solid thin film of FBiBnf(8) showed absorption peaks near 360 nm, 341 nm, 315 nm, and 250 nm, and an emission wavelength peak was observed near 431 nm (excitation wavelength 340 nm).

[0434] The HOMO level and LUMO level of FBiBnf(8) were calculated based on cyclic voltammetry (CV) measurements. The calculation method, measurement method, and measurement device were the same as those in Example 1, so repeated descriptions will be omitted.

[0435] As a result, the HOMO level of FBiBnf(8) was found to be -5.48 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of FBiBnf(8) was found to be -2.37 eV in the measurement of the reduction potential Ec [V]. In addition, when the waveforms after the first and 100th cycles were compared in the repeated measurement of the oxidation-reduction wave, the peak intensity was 85% in the Ea measurement and 94% in the Ec measurement, confirming that FBiBnf(8) has very good resistance to oxidation and reduction.

[0436] Differential scanning calorimetry (DSC) of FBiBnf(8) was also performed using a Rigaku DSC8231-SL. The differential scanning calorimetry was performed by heating the material from 0°C to 290°C at a heating rate of 10°C / min, holding the material at the same temperature for 1 minute, and then cooling it to 0°C at a heating rate of 10°C / min, three times in succession. The results of the second cycle of DSC measurement revealed that the glass transition temperature of FBiBnf(8) was 118°C, indicating that the material has extremely high heat resistance.

[0437] In addition, we performed differential thermal analysis of FBiBnf(8). A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, a heating rate of 10 °C / min, and a nitrogen gas flow (flow rate 200 mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement was 422 °C, indicating that the substance has good sublimation properties. EXAMPLES

[0438] <Synthesis Example 6> In this synthesis example, a method for synthesizing N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: oFBiBnf(8)) shown as structural formula (5-3) in embodiment 1 will be described. The structural formula of oFBiBnf(8) is shown below.

[0439] [ka]

[0440] <Step 1: Synthesis of N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: oFBiBnf(8))> 1.6g (6.3mmol) of 8-chloro-benzo[b]naphtho[1,2-d]furan, 2.3g (6.3mmol) of 2-(2-biphenylyl)amino-9,9-dimethylfluorene, 1.2g (13mol) of sodium tert-butoxide, 44mg (0.13mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (commonly known as cBRIDP(regR)), and 30mL of xylene were placed in a 500mL three-neck flask equipped with a reflux condenser, and the flask was purged with nitrogen. 36mg (63μmol) of bis(dibenzylideneacetone)palladium(0) was added to the flask, and the mixture was heated at 160℃ for 12 hours.

[0441] Toluene and water were added to the resulting mixture, and the organic layer and the aqueous layer were separated. The resulting organic layer was washed twice with water, and then washed with saturated saline. The organic layer was dried over magnesium sulfate. The resulting mixture was gravity filtered to remove the magnesium sulfate. The resulting filtrate was concentrated and dried to obtain 4.1 g of a dark brown solid. The resulting solid was purified by silica gel chromatography (hexane:toluene = 4:1) to obtain 1.2 g of a white solid in a yield of 33%. The synthesis scheme of this synthesis example is shown below.

[0442] [ka]

[0443] The resulting 1.2 g of white solid was purified by train sublimation. The purification was carried out by heating the solid at 225°C for 16 hours under a pressure of 4.0 Pa while flowing argon at 15 mL / min. After the purification, 1.1 g of the target white solid was obtained with a recovery rate of 92%.

[0444] The obtained solid 1 The numerical data of H-NMR are shown below. 1 The H-NMR chart is shown in Figure 63. Note that Figure 63B is a graph showing an enlarged view of the range from 6.6 ppm to 9.0 ppm in Figure 63A. This shows that oFBiBnf(8) was obtained.

[0445] 1 H NMR (Chloroform-d, 300MHz): δ=8.57(d, J=7.8Hz, 1H), 8.00-7.96(m, 2H), 7.80(d, J=8.7Hz, 1H), 7.70(t, J=6.6Hz, 1H), 7.59(d, J=6. 6Hz, 1H), 7.53(t, J=7.5Hz, 1H), 7.49-7.18(m, 12H), 7.01(d, J=7.2Hz, 1H), 6.94-6.79(m, 4H), 6.75(t, J=7.2Hz, 1H), 1.25(s, 6H)

[0446] Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid thin film of oFBiBnf(8) were measured. The measurement method and the device were the same as those in Example 7, so repeated description will be omitted.

[0447] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 64. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown in Figure 65. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0448] From the results in FIG. 64, in the toluene solution of oFBiBnf(8), absorption peaks were observed near 377 nm, 357 nm, and 339 nm, and an emission wavelength peak was observed near 414 nm (excitation wavelength 335 nm).

[0449] Furthermore, from the results in Figure 65, in the solid thin film of oFBiBnf(8), absorption peaks were observed near 390 nm, 385 nm, 360 nm, and 340 nm, and an emission wavelength peak was observed near 423 nm (excitation wavelength 340 nm).

[0450] The HOMO level and LUMO level of oFBiBnf(8) were calculated based on cyclic voltammetry (CV) measurements. The calculation method, measurement method, and measurement device were the same as those in Example 1, so repeated descriptions will be omitted.

[0451] As a result, the HOMO level of oFBiBnf(8) was found to be -5.48 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of oFBiBnf(8) was found to be -2.34 eV in the measurement of the reduction potential Ec [V]. In addition, when the waveforms after the first and 100th cycles were compared in the repeated measurement of the oxidation-reduction wave, the peak intensity was maintained at 92% in the Ea measurement and 94% in the Ec measurement, confirming that oFBiBnf(8) has very good resistance to oxidation and reduction.

[0452] Differential scanning calorimetry (DSC) of oFBiBnf(8) was also performed using a Rigaku DSC8231-SL. The differential scanning calorimetry was performed by heating the sample from 0°C to 220°C at a heating rate of 10°C / min, holding the sample at the same temperature for 1 minute, and then cooling the sample to 0°C at a heating rate of 10°C / min, three times in succession. The results of the second cycle of DSC measurement revealed that the glass transition temperature of oFBiBnf(8) was 114°C, indicating that the material has extremely high heat resistance.

[0453] In addition, we performed a differential thermal analysis of oFBiBnf(8). A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, a heating rate of 10°C / min, and a nitrogen gas flow (flow rate 200 mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement was 364°C, indicating that the substance has good sublimation properties. EXAMPLES

[0454] <Synthesis Example 7> In this synthesis example, a method for synthesizing N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: FBi(4)Bnf(8)) shown as structural formula (5-32) in embodiment 1 will be described. The structural formula of FBi(4)Bnf(8) is shown below.

[0455] [ka]

[0456] <Step 1: Synthesis of FBi(4)Bnf(8)> 1.5g (5.8mmol) of 8-chloro-benzo[b]naphtho[1,2-d]furan, 2.0g (5.8mmol) of 4-(4-biphenylyl)amino-9,9-dimethylfluorene, 1.1g (12mol) of sodium tert-butoxide, 60mg (0.15mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (commonly known as Sphos), and 30mL of xylene were placed in a 500mL three-neck flask equipped with a reflux condenser, and the flask was purged with nitrogen. 33mg (58μmol) of bis(dibenzylideneacetone)palladium(0) was added to the flask, and the mixture was heated at 160℃ for 7 hours.

[0457] Toluene and water were added to the obtained mixture, and the organic layer and the aqueous layer were separated. The obtained organic layer was washed twice with water, and then washed with saturated saline. The organic layer was dried over magnesium sulfate. The obtained mixture was gravity filtered to remove magnesium sulfate. The obtained filtrate was concentrated and dried to obtain 3.6 g of a black-brown solid. The 3.6 g of the black-brown solid was purified by high-performance liquid chromatography (solvent used: chloroform). The obtained fraction solution was concentrated, and the obtained solid was washed with hexane. The obtained solid was dried to obtain 1.7 g of a white solid in a yield of 51%. The synthesis scheme of this synthesis example is shown below.

[0458] [ka]

[0459] The resulting 1.7 g of white solid was purified by train sublimation. The purification was carried out by heating the solid at 245°C for 19 hours under a pressure of 3.8 Pa while flowing argon at 15 mL / min. After the purification, 1.4 g of the target white solid was obtained with a recovery rate of 82%.

[0460] The obtained solid 1 The numerical data of H-NMR are shown below. 1 The H-NMR chart is shown in Figure 66. Note that Figure 66B is a graph showing an enlarged view of the range from 6.8 ppm to 8.8 ppm in Figure 66A. This shows that FBi(4)Bnf(8) was obtained.

[0461] 1 H NMR (dichloromethane-d2,300MHz): δ=8.64(d, J=8.1Hz, 1H), 8.20(dd, J=3.9, 1.2Hz, 1H), 8.04(d, J=7.5Hz, 1H), 7.91(d, J=8.7Hz, 1H), 7.80(d, J=7.5Hz) , 1H), 7.75(t, J=6.9Hz, 1H), 7.63-7.52(m, 4H), 7.50-7.32(m, 8H), 7.31 -7.16(m, 4H), 7.02(t, J=7.5Hz, 1H), 6.93(d, J=9.0Hz, 2H), 1.50(s, 6H)

[0462] Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid thin film of FBi(4)Bnf(8) were measured. The measurement method and the measurement device were the same as those in Example 7, so repeated descriptions will be omitted.

[0463] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 67. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown in Figure 68. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0464] From the results in Figure 67, in the toluene solution of FBi(4)Bnf(8), absorption peaks were observed near 331 nm, 310 nm, and 298 nm, and an emission wavelength peak was observed near 404 nm (excitation wavelength 330 nm).

[0465] Furthermore, from the results in Figure 68, in the solid thin film of FBi(4)Bnf(8), absorption peaks were observed near 370 nm, 335 nm, 316 nm, and 302 nm, and an emission wavelength peak was observed near 414 nm (excitation wavelength 335 nm).

[0466] The HOMO and LUMO levels of FBi(4)Bnf(8) were calculated based on cyclic voltammetry (CV) measurements. The calculation method, measurement method, and measurement device were the same as in Example 1, so repeated descriptions will be omitted.

[0467] As a result, the HOMO level of FBi(4)Bnf(8) was found to be -5.58 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of FBi(4)Bnf(8) was found to be -2.37 eV in the measurement of the reduction potential Ec [V]. In addition, when the waveforms after the first and 100th cycles were compared in the repeated measurement of the oxidation-reduction wave, 80% of the peak intensity was maintained in the Ea measurement, and 95% of the peak intensity was maintained in the Ec measurement, confirming that FBi(4)Bnf(8) has very good resistance to oxidation and reduction.

[0468] Differential scanning calorimetry (DSC) of FBi(4)Bnf(8) was also performed using a Rigaku DSC8231-SL. The differential scanning calorimetry was performed by heating the material from 0°C to 290°C at a heating rate of 10°C / min, holding the material at the same temperature for 1 minute, and then cooling it to 0°C at a heating rate of 10°C / min, three times in succession. The results of the second cycle of DSC measurement revealed that the glass transition temperature of FBi(4)Bnf(8) was 118°C, indicating that the material has extremely high heat resistance.

[0469] In addition, differential thermal analysis (Thermogravimetry-Differential Thermal Analysis) of FBi(4) and Bnf(8) was performed. A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, heating rate of 10°C / min, and nitrogen flow (flow rate 200 mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement was 394°C, indicating that the substance has good sublimation properties. EXAMPLES

[0470] <Synthesis Example 8> In this synthesis example, a method for synthesizing N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: oFBi(4)Bnf(8)) shown as structural formula (5-46) in the embodiment will be described. The structural formula of oFBi(4)Bnf(8) is shown below.

[0471] [ka]

[0472] <Step 1: Synthesis of oFBi(4)Bnf(8)> 1.6g (6.3mmol) of 8-chloro-benzo[b]naphtho[1,2-d]furan, 2.3g (6.3mmol) of 4-(2-biphenylyl)amino-9,9-dimethylfluorene, 1.2g (13mol) of sodium tert-butoxide, 44mg (0.13mmol) of di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (commonly known as cBRIDP(regR)), and 30mL of xylene were placed in a 500mL three-neck flask equipped with a reflux condenser, and the flask was purged with nitrogen. 36mg (63μmol) of bis(dibenzylideneacetone)palladium(0) was added to the flask, and the mixture was heated at 160℃ for 10 hours.

[0473] Toluene and water were added to the obtained mixture, and the organic layer and the aqueous layer were separated. The obtained organic layer was washed twice with water, and then washed with saturated saline. The organic layer was dried over magnesium sulfate. The obtained mixture was gravity filtered to remove magnesium sulfate. The obtained filtrate was concentrated and dried to obtain 4.4 g of a dark brown solid. The obtained solid was purified by silica gel chromatography (hexane:toluene = 3:1) to obtain 1.8 g of a white solid. The obtained 1.8 g of solid was purified by high performance liquid chromatography (solvent used: chloroform). The obtained fraction solution was concentrated, and the obtained solid was washed with hexane. The obtained solid was dried to obtain 1.1 g of a white solid with a yield of 30%. In addition, the obtained white solid was found to have an m / z of 578 as a result of LC\MS analysis, and was found to be the target product. The synthesis scheme of this synthesis example is shown below.

[0474] [ka]

[0475] The resulting white solid (1.1 g) was purified by train sublimation. The purification was carried out by heating the solid at 220°C for 16 hours under a pressure of 5.2 Pa while flowing argon at 10 mL / min. After purification by sublimation, 0.78 g of the target white solid was obtained with a recovery rate of 71%.

[0476] Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid thin film of oFBi(4)Bnf(8) were measured. The measurement method and the measurement device were the same as those in Example 7, so repeated descriptions will be omitted.

[0477] The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 69. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown in Figure 70. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0478] From the results in Figure 69, the toluene solution of oFBi(4)Bnf(8) showed absorption peaks at 341 nm, 327 nm, and 314 nm, and an emission wavelength peak at 412 nm (excitation wavelength 330 nm). Also, from the results in Figure 70, the solid thin film of oFBi(4)Bnf(8) showed absorption peaks at 342 nm and 318 nm, and an emission wavelength peak at 428 nm (excitation wavelength 340 nm).

[0479] The HOMO and LUMO levels of oFBi(4)Bnf(8) were calculated based on cyclic voltammetry (CV) measurements. The calculation method, measurement method, and measurement device were the same as in Example 1, so repeated descriptions will be omitted.

[0480] As a result, the HOMO level of oFBi(4)Bnf(8) was found to be -5.41 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of oFBi(4)Bnf(8) was found to be -2.35 eV in the measurement of the reduction potential Ec [V]. In addition, when the waveforms after the first and 100th cycles were compared in the repeated measurement of the oxidation-reduction wave, the peak intensity was 85% in the Ea measurement and 88% in the Ec measurement, confirming that oFBi(4)Bnf(8) has very good resistance to oxidation and reduction.

[0481] Differential scanning calorimetry (DSC) of oFBi(4)Bnf(8) was also performed using a Rigaku DSC8231-SL. The differential scanning calorimetry was performed by heating the material from 0°C to 250°C at a heating rate of 10°C / min, holding the material at the same temperature for 1 minute, and then cooling it to 0°C at a heating rate of 10°C / min, three times in succession. The results of the second cycle of DSC measurement revealed that the glass transition temperature of oFBi(4)Bnf(8) was 101°C, indicating that the material has extremely high heat resistance.

[0482] In addition, we performed differential thermal analysis of oFBi(4)Bnf(8). A high vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, heating rate of 10°C / min, and nitrogen flow (flow rate 200 mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature (decomposition temperature) at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement was 343°C, indicating that the substance has good sublimation properties.

[0328] The above results demonstrate that the organic compound of one embodiment of the present invention has both high heat resistance and favorable sublimation property, and can provide an organic optical device (light-emitting device and light-receiving device) with high heat resistance and can increase the productivity of device fabrication. EXAMPLES

[0483] Example 1 In this example, a light-emitting device according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of organic compounds used in this example are shown below.

[0484] [ka]

[0485] (Method of Manufacturing Light-Emitting Device 7) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 110 nm, and the electrode area was 2 mm×2 mm.

[0486] Next, as a pretreatment for forming a light-emitting device 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.

[0487] 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.

[0488] Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 is formed faces downward. On the first electrode 101, N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: oFBiBnf(8)) represented by the above structural formula (xii) and ALD-MP001Q (Bunseki Kobo Co., Ltd., material serial number: 1S20180314) are co-deposited to a thickness of 10 nm by a deposition method using resistance heating so that the weight ratio is 1:0.1 (=oFBiBnf(8):ALD-MP001Q) to form a hole injection layer 111.

[0489] Next, oFBiBnf(8) was deposited on the hole injection layer 111 to a thickness of 20 nm, and then N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP) represented by the above structural formula (xiii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0490] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the above structural formula (xiv) and 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02) represented by the above structural formula (x) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) to form the light-emitting layer 113.

[0491] Thereafter, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (xv) was formed to a thickness of 10 nm on the light-emitting layer 113, and further 2-{4-[9,10-di(naphthalen-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN) represented by the above structural formula (xvi) and 8-quinolinolatrium (abbreviation: Liq) represented by the above structural formula (xvii) were co-deposited in a weight ratio of 1:1 to a thickness of 15 nm to form an electron-transporting layer 114.

[0492] After the electron transport layer 114 was formed, aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 7 of this example.

[0493] (Method of Making Light-Emitting Device 8) Light-emitting device 8 was prepared in the same manner as light-emitting device 7, except that oFBiBnf(8) in light-emitting device 7 was replaced with N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: FBiBnf(8)) represented by the above structural formula (xvii).

[0494] The element structure of the above light emitting device is summarized in the table below.

[0495] [Table 11]

[0496] The above light-emitting device was sealed with a glass substrate in a glove box with a nitrogen atmosphere to prevent the light-emitting device from being 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 were measured.

[0497] The luminance-current density characteristics of light-emitting device 7 and light-emitting device 8 are shown in Fig. 71, the current efficiency-luminance characteristics in Fig. 72, the luminance-voltage characteristics in Fig. 73, the current-voltage characteristics in Fig. 74, the external quantum efficiency-luminance characteristics in Fig. 75, and the emission spectrum in Fig. 76. 2 The main characteristics of the vicinity are as follows:

[0498] [Table 12]

[0499] 71 to 76 show that the light-emitting devices 7 and 8 of one embodiment of the present invention are EL devices with high emission efficiency.

[0500] In addition, the current density is 50mA / cm 2 A graph showing the change in luminance with respect to the driving time in the case of the light-emitting device 7 is shown in Fig. 77. As shown in Fig. 77, it was found that both the light-emitting device 7 and the light-emitting device 8, which are light-emitting devices according to an embodiment of the present invention, have a long life. EXAMPLES

[0501] Example 1 In this example, a light-emitting device according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of organic compounds used in this example are shown below.

[0502] [ka]

[0503] (Method of manufacturing light-emitting device 9) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 110 nm, and the electrode area was 2 mm×2 mm.

[0504] Next, as a pretreatment for forming a light-emitting device 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.

[0505] 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.

[0506] 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 was facing downward. On the first electrode 101, N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: FBiBnf(8)) represented by the above structural formula (xvii) and ALD-MP001Q (Bunseki Kobo Co., Ltd., material serial number: 1S20180314) were co-deposited to a thickness of 10 nm by a deposition method using resistance heating so as to have a weight ratio of 1:0.1 (=FBiBnf(8):ALD-MP001Q) to form a hole injection layer 111.

[0507] Next, FBiBnf(8) was deposited on the hole injection layer 111 to a thickness of 90 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0508] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the above structural formula (xiv) and 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02) represented by the above structural formula (x) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) to form the light-emitting layer 113.

[0509] Then, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (xv) was formed to a thickness of 10 nm on the light-emitting layer 113, and further, ALD-MC057Q (Bunseki Kobo Co., Ltd., material serial number: 1S20190330) and 8-quinolinolatritium (abbreviation: Liq) represented by the above structural formula (xvii) were co-deposited at a weight ratio of 1:1 and to a film thickness of 15 nm to form an electron transport layer 114.

[0510] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115, and aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 9 of this embodiment.

[0511] (Method of producing comparative light-emitting device 5) Comparative light-emitting device 5 was prepared in the same manner as light-emitting device 9, except that FBiBnf(8) in light-emitting device 9 was changed to N-(9,9-dimethyl-9H-fluoren-2-yl)-N-(1,1':4',1''-terphenyl-4-yl)-benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: FTPBnf(8)) represented by the above structural formula (xix).

[0512] The element structure of the above light emitting device is summarized in the table below.

[0513] [Table 13]

[0514] The above light-emitting device was sealed with a glass substrate in a glove box with a nitrogen atmosphere to prevent the light-emitting device from being 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 were measured.

[0515] The luminance-current density characteristics of light-emitting device 9 and comparative light-emitting device 5 are shown in Fig. 78, the current efficiency-luminance characteristics in Fig. 79, the luminance-voltage characteristics in Fig. 80, the current-voltage characteristics in Fig. 81, the external quantum efficiency-luminance characteristics in Fig. 82, and the emission spectrum in Fig. 83. 2 The main characteristics of the vicinity are as follows:

[0516] [Table 14]

[0517] 78 to 83 show that the light-emitting device 9 of one embodiment of the present invention is an EL device that has high emission efficiency and shows high emission efficiency even in a low luminance region.

[0518] In addition, the current density is 50mA / cm 2 A graph showing the change in luminance with respect to the driving time in the above case is shown in Fig. 84. As shown in Fig. 84, it was found that both the light-emitting device 9 and the comparative light-emitting device 5 were light-emitting devices with good life spans. EXAMPLES

[0519] Example 1 In this example, a light-emitting device according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of organic compounds used in this example are shown below.

[0520] [ka]

[0521] (Method of Making Light-Emitting Device 10) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 110 nm, and the electrode area was 2 mm×2 mm.

[0522] Next, as a pretreatment for forming a light-emitting device 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.

[0523] 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.

[0524] Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 is formed faces downward. On the first electrode 101, N-(1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)-benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: FBi(4)Bnf(8)) represented by the above structural formula (xx) and ALD-MP001Q (Breakdown Workshop Co., Ltd., material serial number: 1S20180314) are co-deposited to a thickness of 10 nm by a deposition method using resistance heating so that the weight ratio is 1:0.1 (=FBi(4)Bnf(8):ALD-MP001Q) to form a hole injection layer 111.

[0525] Next, FBi(4)Bnf(8) was deposited on the hole injection layer 111 to a thickness of 90 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0526] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the above structural formula (xiv) and 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02) represented by the above structural formula (x) were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) to form the light-emitting layer 113.

[0527] Thereafter, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (xv) was formed to a thickness of 10 nm on the light-emitting layer 113, and further 2-{4-[9,10-di(naphthalen-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN) represented by the above structural formula (xvi) and 8-quinolinolatrium (abbreviation: Liq) represented by the above structural formula (xvii) were co-deposited in a weight ratio of 1:1 to a thickness of 15 nm to form an electron-transporting layer 114.

[0528] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115, and aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 10 of this embodiment.

[0529] The element structure of the light emitting device 10 is summarized in the table below.

[0530] [Table 15]

[0531] The above light-emitting device was sealed with a glass substrate in a glove box with a nitrogen atmosphere to prevent the light-emitting device from being 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 were measured.

[0532] The luminance-current density characteristics of the light-emitting device 10 are shown in Fig. 85, the current efficiency-luminance characteristics in Fig. 86, the luminance-voltage characteristics in Fig. 87, the current-voltage characteristics in Fig. 88, the external quantum efficiency-luminance characteristics in Fig. 89, and the emission spectrum in Fig. 90. 2 The main characteristics of the vicinity are as follows:

[0533] [Table 16]

[0534] 85 to 90 show that the light-emitting device 10, which is a light-emitting device according to one embodiment of the present invention, is an EL device with high emission efficiency. [Explanation of symbols]

[0535] 101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 112: 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: anode, 502: cathode, 511: first light emitting unit, 512: second light emitting unit, 513: charge generation layer, 601: driver circuit section (source line driver circuit), 602: pixel section, 603: driver circuit section (gate line driver circuit), 604: sealing substrate, 605: sealant, 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 device, 951: substrate, 952: electrode, 953: insulating layer, 954: partition layer, 955: EL layer, 956: electrode, 1001: substrate, 1002: Base 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: first electrode, 1024R: first electrode, 1024G: first electrode, 1024B: first electrode, 1025: partition wall, 1028: EL layer, 1029: second electrode, 1031: sealing substrate, 1032: sealing material, 1033: transparent base material, 1034R: red colored layer, 1034G: green colored layer, 1034B: blue colored layer, 1035: black matrix, 1 036: 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: display section, 5003: speaker, 5004: LED lamp, 5005: operation key,5006: Connection terminal, 5007: Sensor, 5008: Microphone, 5012: Support, 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, 7 107: 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. An organic compound represented by the following general formula (G1): 【Chemistry 1】 (In the above general formula (G1), Q represents an oxygen atom or a sulfur atom. In addition, one of A and B represents a group represented by the following general formula (g1-2), and the other represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. In addition, R １ ~R ８ each independently represents any one of hydrogen, an alkyl 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, 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】 (In the above general formula (g1-2), R ９ and R １０ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. When R 9 and R 10 are an alkyl group having 1 to 6 carbon atoms, R 9 and R 10 may be bonded to each other to form a ring, forming a spiro structure. １１ ~R １４ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

2. An organic compound represented by the following general formula (G1-1): 【Chemistry 3】 (In the above general formula (G1-1), Q is an oxygen atom or a sulfur atom. A is a group represented by the following general formula (g1-2), ２０ represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. １ ~R ８ each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 【Chemistry 4】 (In the above general formula (g1-2), R ９ and R １０ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. When R 9 and R 10 are an alkyl group having 1 to 6 carbon atoms, R 9 and R 10 may be bonded to each other to form a ring, forming a spiro structure. １１ ~R １４ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

3. An organic compound represented by the following general formula (G1-2): 【Chemistry 5】 (In the above general formula (G1-2), Q is an oxygen atom or a sulfur atom. B is a group represented by the above general formula (g1), and R ２０ represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. １ ~R ８ each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 【Chemistry 6】 (However, in the above general formula (g1), R ９ and R １０ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. When R 9 and R 10 are an alkyl group having 1 to 6 carbon atoms, R 9 and R 10 may be bonded to each other to form a ring, forming a spiro structure. １１ ~R １４ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

4. In claim 2 or 3, R ２０ An organic compound in which the nucleus is hydrogen.

5. In claim 3, An organic compound in which the group represented by general formula (g1) is a group represented by general formula (g1-1) below: 【Chemistry 7】 (In the above general formula (g1-1), R ９ and R １０ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. When R 9 and R 10 are an alkyl group having 1 to 6 carbon atoms, R 9 and R 10 may be bonded to each other to form a ring, forming a spiro structure. １１ ~R １４ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

6. In claim 3, An organic compound in which the group represented by general formula (g1) is a group represented by the following general formula (g1-2): 【Chemistry 8】 (In the above general formula (g1-2), R ９ and R １０ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. When R 9 and R 10 are an alkyl group having 1 to 6 carbon atoms, R 9 and R 10 may be bonded to each other to form a ring, forming a spiro structure. １１ ~R １４ each independently represents any one of hydrogen, an alkyl 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, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

7. In any one of claims 1 to 6, The Ar is an organic compound represented by the following general formulas (Ar-1) to (Ar-3). 【Chemistry 9】 (However, in the above general formulae (Ar-1) to (Ar-3), R Ａ１ ~R Ａ９ , R Ａ１１ ~R Ａ１９ and R Ａ２１ ~R Ａ２９ each independently represents any one of hydrogen, an alkyl 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, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

8. In claim 6, R Ａ１ ~R Ａ９ , R Ａ１１ ~R Ａ１９ and R Ａ２１ ~R Ａ２９ An organic compound in which the hydrogen atom is

9. In any one of claims 1 to 8, R ９ and R １０ An organic compound in which the methyl group is present.

10. In any one of claims 1 to 9, R １ ~R ８ An organic compound in which the hydrogen atom is

11. In any one of claims 1 to 10, R １１ ~R １４ An organic compound in which the nucleus is hydrogen.

12. In any one of claims 1 to 11, An organic compound in which Q is an oxygen atom.

13. An optical device comprising an organic compound according to any one of claims 1 to 12.

14. A light emitting device comprising an organic compound according to any one of claims 1 to 12.

15. The optical device according to claim 13, a sensor, an operation button, a speaker, or a microphone; An electronic device having the

16. A light-emitting device according to claim 14, a sensor, an operation button, a speaker, or a microphone; An electronic device having the

17. A light emitting device comprising the optical device according to claim 13 and a transistor or a substrate.

18. A light emitting apparatus comprising the light emitting device according to claim 14 and a transistor or a substrate.

19. A lighting device comprising the optical device according to claim 13 and a housing.

20. A lighting device comprising the light-emitting device according to claim 14 and a housing.

Images