Organic compound, organic semiconductor device, light-emitting device, and electronic appliance

Abstract

To provide an organic compound that can yield a light-emitting device with an excellent electron-transport property and excellent reliability.SOLUTION: An organic compound represented by formula (G1) is provided. Here, X represents S or O; R1 to R22 independently represent any one of hydrogen (including deuterium), halogen, nitrile group, alkenyl group, vinyl group, alkynyl group, straight-chain alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 30 carbon atoms, or heteroaryl group having 2 to 30 carbon atoms. At least one of R16 to R22 represents a naphthyl group; n represents an integer from 0 to 4; and Ar1 represents a fluorenyl group or a spirofluorene group.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] One aspect of the present invention relates to organic compounds, organic electronic devices, light-emitting devices, and electronic devices.

[0002] Note that one embodiment of the present invention is not limited to the above technical field. Examples of the technical field of one embodiment of the present invention include a compound, a light-emitting device, a semiconductor device, a display device, a light-emitting device, a power storage device, a memory device, an electronic device, a lighting device, an input device (e.g., a touch sensor), an input / output device (e.g., a touch panel), a driving method thereof, or a manufacturing method thereof. [Background technology]

[0003] In recent years, display devices are expected to be used in various applications. For example, applications of large display devices include home television devices (also called televisions or television receivers), digital signage, and public information displays (PIDs). In addition, development of smartphones and tablet terminals equipped with touch panels as mobile information terminals is underway.

[0004] At the same time, there is also a demand for higher resolution display devices. Devices requiring high resolution display devices, such as devices for virtual reality (VR), augmented reality (AR), substitutional reality (SR), and mixed reality (MR), are being actively developed.

[0005] As a display device, a light-emitting device having a light-emitting device (also called a light-emitting element) using an organic compound has been developed. A light-emitting device (also called an organic EL device or light-emitting device) using the electroluminescence (hereinafter referred to as EL) phenomenon has features such as being easily thin and lightweight, being capable of responding quickly to an input signal, and being capable of being driven by a DC constant voltage power supply, and is applied to a display device.

[0006] Displays and lighting devices using light-emitting devices are suitable for use in a variety of electronic devices, and research and development into both materials and devices is ongoing in search of light-emitting devices with better characteristics (see, for example, Patent Document 1). [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2021 / 132995 Summary of the Invention [Problem to be solved by the invention]

[0008] An object of one embodiment of the present invention is to provide a novel organic compound. Alternatively, an object of one embodiment of the present invention is to provide a novel carrier-transporting material. Alternatively, an object of one embodiment of the present invention is to provide a novel hole-transporting material. Alternatively, an object of one embodiment of the present invention is to provide a carrier-transporting material or a hole-transporting material having good heat resistance.

[0009] Another object of one embodiment of the present invention is to provide a light-emitting device with low driving voltage, or a light-emitting device, electronic device, and display device with low power consumption.

[0010] Note that the description of these problems does not preclude the existence of other problems. One embodiment of the present invention does not necessarily have to solve all of these problems. Problems other than these can be extracted from the description of the specification, drawings, and claims. [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 general formula (G1), X represents a sulfur atom or an oxygen atom, and R 1 ~R 22 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R 16 ~R 22 At least one of R represents a substituted or unsubstituted naphthyl group, n represents an integer of 0 to 4, and when n is 2 or more, a plurality of R 12 ~R 15 may be the same or different. 1 is represented by the following general formula (g1-1) or the following general formula (g1-2).

[0014] [ka]

[0015] In the general formula (g1-1) and the general formula (g1-2), R 23 ~R 30 Either one of the following or R 33 ~R 48 Any one of the above is bonded to the nitrogen of the amine in general formula (G1), and the other and R 31 , R 32 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0016] Another embodiment of the present invention is an organic compound in which n is 0 or 1 in the above structure.

[0017] Another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[0018] [ka]

[0019] In the general formula (G2), X represents a sulfur atom or an oxygen atom, and R 1 ~R 11 and R 16 ~R 22each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R 16 ~R 19 At least one of Ar represents a substituted or unsubstituted naphthyl group. 1 is represented by the following general formula (g1-1) or the following general formula (g1-2).

[0020] [ka]

[0021] In the general formula (g1-1) and the general formula (g1-2), R 23 ~R 30 Either one of the following or R 33 ~R 48 Any one of the above is bonded to the nitrogen of the amine in general formula (G2), and the other and R 31 , R 32 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0022] Another embodiment of the present invention is an organic compound represented by the following general formula (G3).

[0023] [ka]

[0024] In the general formula (G3), X represents a sulfur atom or an oxygen atom, and R 1 ~R 11 and R 16 ~R 22 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R 16 ~R 22 At least one of Ar represents a substituted or unsubstituted naphthyl group. 1 is represented by the following general formula (g1-1) or the following general formula (g1-2).

[0025] [ka]

[0026] In the general formula (g1-1) and the general formula (g1-2), R 23 ~R 30 Either one of the following or R 33 ~R 48 Any one of the above is bonded to the nitrogen of the amine in general formula (G3), and the other and R 31 , R 32each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0027] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device comprising the steps of: 16 ~R 22 Any one of the above is an organic compound represented by the following general formula (g2).

[0028] [ka]

[0029] In the general formula (g2), R 49 ~R 55 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0030] Another embodiment of the present invention is an organic compound represented by the following general formula (G4).

[0031] [ka]

[0032] In the general formula (G4), X represents a sulfur atom or an oxygen atom, and R 1 ~R 11 , R 16 , R 17 , R 19 ~R 22 and R 49 ~R 55 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. 1 is represented by the following general formula (g1-1) or the following general formula (g1-2).

[0033] [ka]

[0034] In the general formula (g1-1) and the general formula (g1-2), R 23 ~R 30 Either one of the following or R 33 ~R 48 Any one of the following is bonded to the nitrogen of the amine in general formula (G4); 31 , R 32 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0035] Another embodiment of the present invention is an organic compound represented by the following general formula (G5).

[0036] [ka]

[0037] In the general formula (G5), X represents a sulfur atom or an oxygen atom, and R 1 ~R 11 and R 16 , R 17 , R 19 ~R 28 , R 30 ~R 32 and R 49 ~R 55 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0038] Another embodiment of the present invention is an organic compound represented by the following general formula (G6).

[0039] [ka]

[0040] In the general formula (G6), X represents a sulfur atom or an oxygen atom, and R 1 ~R 11 and R 16 , R 17 , R 19 ~R 22 and R 33 ~R 38 , R40 ~R 55 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0041] Another embodiment of the present invention is an organic semiconductor device including any of the organic compounds described above.

[0042] Another embodiment of the present invention is a light-emitting device including any of the above organic compounds.

[0043] Another embodiment of the present invention is a light-receiving device including any of the organic compounds described above.

[0044] Another embodiment of the present invention is an organic electronic device having a light-emitting device including any one of the organic compounds described above and a light-receiving device including any one of the organic compounds described above on the same plane.

[0045] Another embodiment of the present invention is an organic electronic device using any one of the organic compounds described above in a capping layer.

[0046] Another embodiment of the present invention is an electronic device including the organic electronic device. Effect of the Invention

[0047] According to one embodiment of the present invention, a novel organic compound can be provided. Alternatively, according to one embodiment of the present invention, a novel carrier-transporting material can be provided. Alternatively, according to one embodiment of the present invention, a novel hole-transporting material can be provided. Alternatively, according to one embodiment of the present invention, a carrier-transporting material or a hole-transporting material having good heat resistance can be provided.

[0048] According to another embodiment of the present invention, a light-emitting device with low driving voltage can be provided. According to another embodiment of the present invention, a light-emitting device, a light-emitting device, an electronic device, and a display device with low power consumption can be provided.

[0049] In another embodiment of the present invention, a novel light-emitting device, a novel display device, a novel display module, and a novel electronic device can be provided.

[0050] Note that the description of these effects does not preclude the existence of other effects. One embodiment of the present invention does not necessarily have all of these effects. Effects other than these can be extracted from the description in the specification, drawings, and claims. [Brief description of the drawings]

[0051] [Figure 1] 1A to 1C are diagrams illustrating a light emitting device. [Diagram 2] 2(A) and 2(B) are a top view and a cross-sectional view of a light emitting device. [Diagram 3] 3A to 3E are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 4] 4A to 4D are cross-sectional views showing an example of a method for manufacturing a display device. [Diagram 5] 5A to 5D are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 6] 6A to 6C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 7]7A to 7C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 8] 8A to 8C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 9] 9(A) and 9(B) are perspective views showing configuration examples of a display module. [Figure 10] 10A and 10B are cross-sectional views showing configuration examples of a display device. [Figure 11] FIG. 11 is a perspective view showing a configuration example of a display device. [Figure 12] FIG. 12 is a cross-sectional view showing a configuration example of a display device. [Figure 13] FIG. 13 is a cross-sectional view showing a configuration example of a display device. [Figure 14] FIG. 14 is a cross-sectional view showing a configuration example of a display device. [Figure 15] 15A to 15D are diagrams illustrating examples of electronic devices. [Figure 16] 16A to 16F are diagrams illustrating examples of electronic devices. [Figure 17] 17A to 17G are diagrams illustrating examples of electronic devices. [Figure 18] FIG. 18 is a diagram illustrating a photosensor. [Figure 19] Figures 19(A) and 19(B) are 1H-NMR spectra of Fr(2)F(4)A(βN2)B. [Figure 20] Figures 20(A) and 20(B) show the absorption and PL spectra of Fr(2)F(4)A(βN2)B. [Figure 21] Figures 21(A) and 21(B) are 1H-NMR spectra of FrFA(βN2)B. [Figure 22] Figures 22(A) and 22(B) are the absorption and PL spectra of FrFA(βN2)B. [Figure 23] FIG. 23 is a graph showing luminance-current density characteristics of a light-emitting device according to one embodiment of the present invention. [Figure 24] FIG. 24 shows current efficiency vs. luminance characteristics of a light-emitting device according to one embodiment of the present invention. [Diagram 25] FIG. 25 is a graph showing the luminance-voltage characteristics of a light-emitting device according to one embodiment of the present invention. [Figure 26] FIG. 26 shows current density-voltage characteristics of a light-emitting device according to one embodiment of the present invention. [Figure 27] FIG. 27 is a graph showing the external quantum efficiency vs. luminance characteristics of a light-emitting device according to one embodiment of the present invention. [Figure 28] FIG. 28 shows an electroluminescence spectrum of a light-emitting device according to one embodiment of the present invention. [Figure 29] Figures 29(A) and 29(B) are 1H-NMR spectra of N-(chlorophenyl-4-yl)dibenzofuran-2-amine. [Diagram 30] Figures 30(A) and 30(B) are 1H-NMR spectra of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-2-amine. [Diagram 31] Figures 31(A) and 31(B) are 1H-NMR spectra of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine. [Diagram 32] Figures 32(A) and 32(B) are 1H-NMR spectra of Fr(2)FA(βN2)B. [Diagram 33] Figures 33(A) and 33(B) are 1H-NMR spectra of N-(chlorophenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-4-amine. [Diagram 34] Figures 34(A) and 34(B) are 1H-NMR spectra of FrF(4)A(βN2)B. [Diagram 35] Figures 35(A) and 35(B) are 1H-NMR spectra of Fr(1)FA(βN2)B. [Diagram 36]Figures 36(A) and 36(B) are 1H-NMR spectra of N-(chlorophenyl-4-yl)-N-(9,9-diphenyl-9H-fluoren-2-yl)dibenzofuran-2-amine. [Figure 37] Figures 37(A) and 37(B) are 1H-NMR spectra of Fr(2)FLP(2)A(βN2)B. [Figure 38] Figures 38(A) and 38(B) are 1H-NMR spectra of N-(chlorophenyl-4-yl)-N-(9,9-diphenyl-9H-fluoren-2-yl)dibenzofuran-4-amine. [Figure 39] Figures 39(A) and 39(B) are 1H-NMR spectra of FrFLP(2)A(βN2)B. [Diagram 40] Figures 40(A) and 40(B) are 1H-NMR spectra of FrSFA(βN2)B. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0052] The embodiments 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 modes 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.

[0053] (Embodiment 1) In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0054] An organic compound according to one embodiment of the present invention is represented by the following general formula (G1).

[0055] [ka]

[0056] In the organic compound represented by the above general formula (G1), R 16~R 22 At least one of R represents a substituted or unsubstituted naphthyl group, and the others and R 1 ~R 15 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and is particularly preferably hydrogen (including deuterium), a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, since it is possible to provide a material having high heat resistance and a low sublimation temperature. When a material having high heat resistance is used, it is possible to provide an organic semiconductor device (such as a light-emitting device or a light-receiving device) having high heat resistance, and it can be suitably used for in-vehicle applications requiring high temperature resistance. In addition, when a material having a low sublimation temperature is used, it is possible to prevent or reduce the occurrence of thermal decomposition in the heating step required for deposition when fabricating an organic semiconductor device by deposition, and therefore it is possible to provide a high-purity film, and as a result, it is possible to provide a highly reliable organic semiconductor device, which is preferable. In addition, when a material having an alkyl group or a cycloalkyl group is used, it is possible to form a film with a low refractive index, and therefore it is preferable to provide a device with high light extraction efficiency when the material of the present application is used in the transport layer of a light-emitting device. In addition, when R other than a naphthyl group is used, 16 ~R 22 and R 1 ~R 15 is preferably hydrogen since synthesis is simplified.

[0057] An organic compound having such a structure has a phenylene group bonded to the nitrogen of the amine substituted at the para position, and therefore has high heat resistance and high hole transport property. When the material of the present application is used in an organic semiconductor device, it is preferable because a device with a low driving voltage can be provided, and as a result, an organic semiconductor device with low power consumption can be provided.

[0058] In addition, R 16 ~R 22 At least one of R is a substituted or unsubstituted naphthyl group. 16 ~R 22 It is preferable that one or two of the groups be a substituted or unsubstituted naphthyl group, because this allows the device to have small voltage fluctuations when continuously operated, and provides an organic semiconductor device that operates at a stable voltage when operated. It is preferable that only one of the groups be a substituted or unsubstituted naphthyl group, because this prevents the deposition temperature from becoming too high and provides high hole transportability.

[0059] In the organic compound represented by the general formula (G1), n ​​represents an integer of 0 to 4. When n is 2 or more, a plurality of R 12 ~R 15 may be the same or different. It is preferable that n is 0 or 1, since the deposition temperature is not too high, and therefore hole transportability is improved, and also, since the voltage change during operation is small, a highly reliable organic semiconductor device is provided. In addition, it is preferable that the phenylene group bonded to the amine is a paraphenylene group, since it is possible to improve hole transportability, but when three or more phenylene groups are linked at the para position, the effective conjugation length is extended, and the absorption wavelength may extend to visible light, and in such a case, there is a concern that the light extraction efficiency of the light-emitting device may decrease. Therefore, n is preferably 0 or 1, and when n is 2 or more, it is preferable to bond at the meta position, where the effective conjugation length is less likely to extend, or at the ortho position, where three-dimensional twisting occurs, rather than the para position.

[0060] In the organic compound represented by the general formula (G1), X is a sulfur atom or an oxygen atom. When X is an oxygen atom, the refractive index is lower than that of a compound having a sulfur atom, and a device using a compound having a low refractive index has an effect of increasing the light extraction efficiency, so that a highly efficient light-emitting device can be provided, which is preferable. In addition, when X is a sulfur atom, the heat resistance is improved compared to a compound having an oxygen atom, so that a device resistant to high-temperature operation can be provided, which is preferable. In addition, when sulfur is used, the refractive index is high, so that a light-emitting device with high light extraction efficiency can be provided by forming a film with a high refractive index on the upper part of the cathode.

[0061] In the organic compound represented by the general formula (G1), Ar 1 is a group represented by the following general formula (g1-1) or the following general formula (g1-2).

[0062] [ka]

[0063] Ar 1 is a group represented by general formula (g1-1), R 23 ~R 30 Any one of the following is bonded to the nitrogen of the amine in general formula (G1); 31 , R 32 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and is particularly preferably hydrogen (including deuterium), a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms.

[0064] Ar 1 is a group represented by general formula (g1-2), R 33 ~R 48 Any one of the following is bonded to the nitrogen of the amine in general formula (G1), and the others each independently represent any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and particularly preferably hydrogen (including deuterium), a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms.

[0065] An organic compound having such a structure can be a material having good hole transport properties and high heat resistance. In addition, a thin film containing an organic compound having such a structure is preferable because it has little change in film quality and can provide a device that is stable against heat or driving. In addition, a device using an organic compound having such a structure can be a device that has a low driving voltage, has a small voltage fluctuation during driving, has high reliability against voltage, and has excellent reliability when driven at high temperatures. In addition, it is preferable because it can be a device with low power consumption. In addition, an organic compound having such a structure is preferable because it has high sublimation properties, does not decompose in the deposition process, and can form a high-purity film, so that a reliable organic semiconductor device can be provided, and is also preferable in terms of manufacturing costs because it can be produced stably.

[0066] In the organic compound represented by the general formula (G1), n ​​is preferably 0 in order to prevent the deposition temperature from becoming too high, enhance hole transportability, and provide a highly reliable organic semiconductor device with small voltage change during operation. That is, the organic compound of one embodiment of the present invention is preferably an organic compound represented by the following general formula (G2).

[0067] [ka]

[0068] In the above general formula (G2), R 1 ~R 11 and R 16 ~R 22 and Ar 1 is the same as in general formula (G1) above, so repeated explanation will be omitted.

[0069] In the organic compound represented by the above general formula (G2), the naphthyl group bonded to the paraphenylene group is preferably bonded to the paraphenylene group at the 2-position in order to achieve high hole transport properties and high reliability during driving. That is, the organic compound of one embodiment of the present invention is preferably an organic compound represented by the following general formula (G3).

[0070] [ka]

[0071] In the above general formula (G3), R 1 ~R 11 and R 16 ~R 22 and Ar 1 is the same as in general formula (G1) above, so repeated explanation will be omitted.

[0072] In the organic compounds represented by the general formulas (G1) to (G3), R 16 ~R 22At least one of the above is a substituted or unsubstituted naphthyl group, and the substituted or unsubstituted naphthyl group is preferably a substituted or unsubstituted 2-naphthyl group represented by the following general formula (g2), in order to achieve high hole transport properties and high reliability during operation.

[0073] [ka]

[0074] In the above general formula (g2), R 49 ~R 55 each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. 49 ~R 55 are each independently any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, and a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, which have high hole transport properties, high heat resistance, and high stability of a thin film; are each independently preferably any one of hydrogen (including deuterium) and a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, which can reduce the sublimation temperature and the deposition temperature and can suppress thermal decomposition during deposition; and are further preferably hydrogen (including deuterium), which can reduce the synthesis cost.

[0075] The organic compound of one embodiment of the present invention has a structure in which a substituted or unsubstituted binaphthyl group is bonded to at least the nitrogen of an amine via a substituted or unsubstituted paraphenylene group, and the binaphthyl group is preferably a substituted or unsubstituted 2,2'-binaphthyl-6-yl group, because the driving voltage of an organic semiconductor device using the organic compound of one embodiment of the present application is reduced, or the voltage change upon driving is small, or the power consumption is small, or the device has high heat resistance, or the reliability upon driving is improved. That is, the organic compound of one embodiment of the present invention is preferably an organic compound represented by the following general formula (G4).

[0076] [ka]

[0077] In the above general formula (G4), R 1 ~R 11 , R 16 , R 17 , R 19 ~R 22 is the above general formula (G1) and R 49 ~R 55 is the same as the above general formula (g2), so repeated explanation will be omitted.

[0078] In addition, another aspect of the present invention is the above-mentioned structure, 1 However, when the fluoren-2-yl group is a substituted or unsubstituted fluoren-2-yl group, the highest occupied molecular orbital level (HOMO level) becomes relatively high, and the organic compound has high hole transport properties, so that when the fluoren-2-yl group is used in a light-emitting device, a light-emitting device with low driving voltage, high light-emitting efficiency, and high reliability can be provided. That is, the organic compound of one embodiment of the present invention is preferably an organic compound represented by the following general formula (G5).

[0079] [ka]

[0080] In the above general formula (G5), R 1 ~R 11 , R 16 , R 17 , R 19 ~R 22 is the above general formula (G1) and R 23 ~R 28 , R 30 ~R 32 is the above general formula (g1-1), and R 49 ~R 55 is the same as the above general formula (g2), so repeated explanation will be omitted.

[0081] In addition, another aspect of the present invention is the above-mentioned structure, 1 However, when the 9,9'-spirobi[9H-fluoren]-2-yl group is substituted or unsubstituted, the HOMO level is relatively high, and therefore an organic compound having high hole transport properties can be provided. In addition, since the HOMO level of the organic compound is relatively high, the organic compound has excellent hole injection properties into an emitting layer containing an organic compound having a high HOMO level, particularly a phosphorescent device using a bipolar host or a mixed host of a hole transporting host and an electron transporting host. Therefore, when the organic compound is used as a material for a hole transporting layer in contact with an emitting layer in a phosphorescent light-emitting device, particularly a green phosphorescent light-emitting device or a red phosphorescent light-emitting device, a phosphorescent light-emitting device having good reliability during high-temperature operation and low driving voltage can be provided. In addition, a light-emitting device having high luminous efficiency can be provided. In addition, a device having good reliability can be provided.

[0082] That is, the organic compound of one embodiment of the present invention is preferably an organic compound represented by the following general formula (G6).

[0083] [ka]

[0084] In the above general formula (G6), R 1 ~R 11 , R 16 , R17 , R 19 ~R 22 is the above general formula (G1) and R 33 ~R 38 , R 40 ~R 48 is the above general formula (g1-2) and R 49 ~R 55 is the same as the above general formula (g2), so repeated explanation will be omitted.

[0085] In the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), specific examples of halogen include fluorine, chlorine, bromine and iodine.

[0086] In addition, in the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), examples of the alkenyl group include an ethenyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a sec-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, an isopenten ... Examples of octenyl groups include 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-heptenyl group, 2-heptenyl group, 3-heptenyl group, 4-heptenyl group, 5-heptenyl group, 6-heptenyl group, 1-octenyl group, 2-octenyl group, 3-octenyl group, 4-octenyl group, 5-octenyl group, 6-octenyl group, and 7-octenyl group.

[0087] In addition, in the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a sec-butynyl group, an isobutynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, an isopentynyl group, an alkynyl group, and an alkynyl group. Examples of octynyl groups include 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, 1-heptynyl group, 2-heptynyl group, 3-heptynyl group, 4-heptynyl group, 5-heptynyl group, 6-heptynyl group, 1-octynyl group, 2-octynyl group, 3-octynyl group, 4-octynyl group, 5-octynyl group, 6-octynyl group, and 7-octynyl group.

[0088] In addition, in the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), specific examples of the linear alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, etc. When the linear alkyl group having 1 to 6 carbon atoms has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

[0089] In addition, in the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), specific examples of the cycloalkyl group having 3 to 10 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononanyl group, a cyclodecanyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a tricyclo[5.2.1.0(2,6)]decanyl group, a noradamantyl group, etc. When the cycloalkyl group having 3 to 10 carbon atoms has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

[0090] In addition, in the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), specific examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a tert-butoxy group, a sec-butoxy group, an isobutoxy group, a pentyloxy group, an octyloxy group, an allyloxy group, a cyclohexyloxy group, a phenoxy group, a benzyloxy group, a vinyloxy group, a propenyloxy group, a butenyloxy group, a pentenyloxy group and a hexenyloxy group. When the alkoxy group having 1 to 6 carbon atoms has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

[0091] In addition, in the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), examples of the alkylsilyl group having 3 to 12 carbon atoms include a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a triisopropylsilyl group, a tri-tert-butylsilyl group, a tributylsilyl group, etc. When the alkylsilyl group having 3 to 12 carbon atoms has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

[0092] In addition, in General Formulae (G1) to (G6), (g1-1), (g1-2) and (g2), examples of the aryl group having 6 to 30 carbon atoms include a phenyl group, a tolyl group, a xylyl group, a biphenyl group, an indenyl group, a naphthyl group, a fluorenyl group, a spirofluorenyl group, a phenanthrenyl group, a triphenylenyl group, an anthracenyl group, a fluoranthenyl group, etc. When the aryl group having 6 to 30 carbon atoms has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

[0093] In the general formulae (G1) to (G6), (g1-1), (g1-2), and (g2), examples of the heteroaryl group having 2 to 30 carbon atoms include a pyridinyl group, a pyrimidinyl group, a triazinyl group, a phenanthroline-yl group, a carbazolyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a bipyridinyl group, a bipyrimidinyl group, a pyrazinyl group, a bipyrazine-yl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a dibenzoquinoxalinyl group, an azofluorenyl group, a diazofluorenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a benzocarbazolyl group, a ... Examples of such groups include a zonaphthofuranyl group, a dinaphthofuranyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, a dinaphthothiophenyl group, a benzofuropyridinyl group, a benzofuropyrimidinyl group, a benzothiopyridinyl group, a benzothiopyrimidinyl group, a naphthofuropyridinyl group, a naphthofuropyrimidinyl group, a naphthothiopyridinyl group, a naphthothiopyrimidinyl group, a dibenzoquinoxalinyl group, an acridine-yl group, a xanthene-yl group, a phenothiazinyl group, a phenoxazinyl group, a phenazinyl group, a triazolyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a benzimidazolyl group, or a pyrazolyl group. When the heteroaryl group having 2 to 30 carbon atoms has a substituent, the substituent is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

[0094] It is to be noted that hydrogen contained in the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2) includes deuterium.

[0095] In addition, when the alkenyl group, vinyl group, alkynyl group, cycloalkyl group, alkoxy group, alkylsilyl group, aryl group, and heteroaryl group are groups having a substituent, the substituent may be an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group. Specific examples of the cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, and a norbornanyl group. Specific examples of the aryl group having 6 to 12 carbon atoms include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted biphenyl group.

[0096] In addition, when the linear alkyl group is a group having a substituent, the substituent may be a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. Specific examples of the cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Specific examples of the aryl group having 6 to 12 carbon atoms include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted biphenyl group.

[0097] In the organic compounds represented by the above general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), R 1 ~R 55Specific examples of elements or groups that can be used as the substituent include groups represented by the following structural formulae (1-1) to (1-35) and (2-1) to (2-60). For groups that do not specify a bond, a monovalent group from which one of the hydrogen atoms has been eliminated can be used.

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] The organic compound of one embodiment of the present invention having the above-described structure can be a material having good hole-transporting properties and high heat resistance. In addition, a thin film including a compound having such a structure is preferable because it has little change in film quality and can provide a device that is stable against heat or the passage of driving time. In addition, a device using a compound having such a structure can be a device that has high reliability against voltage because it has a low driving voltage and small voltage fluctuation during driving, and has excellent reliability when driven at high temperatures. In addition, a device with low power consumption can be provided. In addition, an organic compound having such a structure is preferable in terms of manufacturing cost because it has high sublimation property and does not decompose during a deposition process and can be produced stably.

[0103] Next, a method for synthesizing an organic compound represented by the following general formula (G1) will be described.

[0104] [ka]

[0105] In the above general formula (G1), R 1 ~R 22 , X, n, Ar 1 This is the same as that described in the present embodiment.

[0106] The organic compound represented by the general formula (G1) can be synthesized according to the following synthesis schemes (a-1) and (a-2).

[0107] [ka]

[0108] [ka]

[0109] In the synthetic schemes (a-1) and (a-2), Q 1 and Q 2 Each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. 1 ~R 22 , X, n, Ar 1 is the same as the organic compound represented by general formula (G1).

[0110] The organic compound represented by the general formula (G1) can be prepared by first reacting Ar 1 By cross-coupling a compound having a fluorene skeleton represented by ((g1-1) or (g1-2)) (compound 1) with an amine compound having a dibenzofuran skeleton or a dibenzothiophene skeleton (compound 2), Ar 1 A dibenzofuranylamine or dibenzothiophenylamine compound having a fluorene skeleton represented by the following formula (compound 3) is obtained.

[0111] Next, Ar1 By cross-coupling a dibenzofuranylamine or dibenzothiophenylamine compound having a fluorene skeleton represented by the formula (3) with a compound having a binaphthalene skeleton represented by the formula (4), the binaphthalene skeleton and Ar 1 In this way, an organic compound according to one embodiment of the present invention, which is represented by General Formula (G1) and which has a fluorene skeleton represented by the following formula, and further a dibenzofuran skeleton or a dibenzothiophene skeleton, can be obtained.

[0112] The above synthesis schemes (a-1) and (a-2) can use the Buchwald-Hartwig reaction using a palladium catalyst. In this case, the palladium catalyst may be a palladium compound such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), or allylpalladium(II) chloride (dimer); and the ligand may be tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyltri(orthotolyl)phosphine, (S)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diisopropylphosphine) (abbreviation: cBRIDP), or the like.

[0113] In the reaction, an organic base such as sodium tert-butoxide, an inorganic base such as potassium carbonate, cesium carbonate, sodium carbonate, etc. can also be used. In addition, in the reaction, toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used as a solvent. Reagents that can be used in the reaction are not limited to the above-mentioned reagents.

[0114] In the above synthesis schemes (a-1) and (a-2), a compound in which an organotin group is bonded to the amino group of compound 2 or compound 3 can be used in place of compound 2 or compound 3.

[0115] Compound 3 used in the above synthesis schemes (a-1) and (a-2) can also be obtained as shown in the following synthesis scheme (a-1-1).

[0116] [ka]

[0117] In the synthetic scheme (a-1-1), Q 3 represents a chlorine, bromine, iodine, or triflate group. R in Compound 3, Compound 5, and Compound 6 1 ~R 7 , X, Ar 1 is the same as the organic compound represented by the general formula (G1). In addition, the above synthesis scheme (a-1-1) can be carried out using the Buchwald-Hartwig reaction using a palladium catalyst, similarly to the synthesis schemes (a-1) and (a-2).

[0118] The organic compound represented by the general formula (G1) can be synthesized according to the following synthesis schemes (a-3) and (a-4).

[0119] [ka]

[0120] [ka]

[0121] In the synthetic schemes (a-3) and (a-4), Q 2 and Q 3 Each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. 1 ~R 22 , X, n, Ar 1is the same as the organic compound represented by the general formula (G1). In addition, the above synthesis schemes (a-3) and (a-4) can be carried out using the Buchwald-Hartwig reaction using a palladium catalyst, similarly to the synthesis schemes (a-1) and (a-2).

[0122] The organic compound represented by the general formula (G1) can be prepared by first reacting Ar 1 The amine compound having a fluorene skeleton represented by the formula (compound 5) and the compound having a binaphthalene skeleton represented by the formula (compound 4) are cross-coupled to give Ar 1 It is possible to obtain an amine compound having a fluorene skeleton and a binaphthalene skeleton (compound 7) represented by the following formula:

[0123] Next, according to the synthesis scheme (a-4), Ar 1 By cross-coupling an amine compound having a fluorene skeleton and a binaphthalene skeleton (compound 7) with a compound having a dibenzofuran skeleton or a dibenzothiophene skeleton (compound 6), the binaphthalene skeleton and Ar 1 In this way, an organic compound according to one embodiment of the present invention, which is represented by General Formula (G1) and which has a fluorene skeleton represented by the following formula, and further a dibenzofuran skeleton or a dibenzothiophene skeleton, can be obtained.

[0124] Compound 7 used in the above synthesis schemes (a-3) and (a-4) can also be obtained as shown in the following synthesis schemes (a-3-1) and (a-3-2).

[0125] [ka]

[0126] [ka]

[0127] In the synthetic schemes (a-3-1) and (a-3-2), Q 1 and Q4 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. 8 ~R 22 each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; R 8 ~R 22 may be bonded to each other to form a ring, and in this case, the boron compound may be pinacolborane or the like. 8 ~R 22 , X, n, Ar 1 is the same as the organic compound represented by general formula (G1).

[0128] First, as shown in the above synthesis scheme (a-3-1), an amine compound having a binaphthalene skeleton (compound 10) can be obtained by cross-coupling an aniline compound (compound 8) with a boron compound having a binaphthalene skeleton (compound 9).

[0129] Next, as shown in the above synthesis scheme (a-3-2), an amine compound having a binaphthalene skeleton (compound 10) and Ar 1 Compound 7 can be obtained by cross-coupling a compound having a fluorene skeleton represented by the following formula (compound 1):

[0130] In the above synthesis scheme (a-3-1), the Suzuki-Miyaura reaction can be carried out using a palladium catalyst. In this case, the palladium catalyst can be a palladium compound such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0) or bis(triphenylphosphine)palladium(II) dichloride, and the ligand can be tri(orthotolyl)phosphine, triphenylphosphine or tricyclohexylphosphine.

[0131] In this reaction, an organic base such as sodium tert-butoxide or an inorganic base such as potassium carbonate or sodium carbonate can be used as a base. In addition, in this reaction, a mixed solvent of toluene and water, a mixed solvent of xylene and water, a mixed solvent of benzene and water, a mixed solvent of ethers such as ethylene glycol dimethyl ether, or 1,4-dioxane and water can be used as a solvent. The higher the solubility of boronic acid or boron compounds in the water layer, the faster the reaction rate becomes, and the higher the yield can be expected. Therefore, it is preferable to add water, but when ethers are used as a solvent, it is expected that the same effect can be obtained without adding water. In addition, a mixed solvent of toluene, water, and alcohol such as ethanol, a mixed solvent of xylene, water, and ethanol, a mixed solvent of benzene, water, and ethanol, etc. can be used as a reaction solvent. In particular, a mixed solvent of toluene and water, a mixed solvent of toluene, water, and ethanol, and a mixed solvent of ethers and water such as ethylene glycol dimethyl ether are preferable.

[0132] In addition, instead of the organic boron compound or boronic acid, a cross-coupling reaction of an organic aluminum compound, an organic zirconium compound, an organic zinc compound, an organic tin compound, or the like with a halide or a compound having a triflate group may be used.

[0133] The above synthesis scheme (a-3-2) can be carried out using a Buchwald-Hartwig reaction using a palladium catalyst, similarly to the synthesis schemes (a-1) and (a-2).

[0134] The compound 10 synthesized in the above synthesis scheme (a-3-1) can also be synthesized as shown in the following synthesis scheme (a-3-1-1).

[0135] [ka]

[0136] In the synthetic scheme (a-3-1-1), Q 2represents a chlorine, bromine, iodine, or triflate group. 8 ~R 22 each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; R 8 ~R 22 may be bonded to each other to form a ring, and in this case, the boron compound may be pinacolborane. 8 ~R 22 , X, n, Ar 1 is the same as the organic compound represented by the general formula (G1). In addition, the above synthesis scheme (a-3-1-1) can be carried out using the Suzuki-Miyaura reaction using a palladium catalyst, similarly to the synthesis scheme (a-3-1).

[0137] In the above synthesis scheme (a-3-1-1), an aniline compound having a binaphthalene skeleton (compound 10) can be obtained by cross-coupling a boron compound having an aniline skeleton (compound 11) and a compound having a binaphthalene skeleton (compound 4).

[0138] Compound 7 used in the above synthesis schemes (a-3) and (a-4) can also be obtained as shown in the following synthesis schemes (a-3-2-1) and (a-3-2-2).

[0139] [ka]

[0140] [ka]

[0141] In the synthetic schemes (a-3-2-1) and (a-3-2-2), Q 1 and Q 4 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. 8 ~R 22 each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; R8 ~R 22 may be bonded to each other to form a ring, and in this case, the boron compound may be pinacolborane or the like. 8 ~R 22 , X, n, Ar 1 is the same as the organic compound represented by general formula (G1).

[0142] First, as shown in the above synthesis scheme (a-3-2-1), Ar 1 By cross-coupling a compound having a fluorene skeleton represented by the formula (Compound 1) with an aniline compound (Compound 8), the phenyl group and Ar 1 It is possible to obtain an amine compound (compound 12) having a fluorene skeleton represented by the following formula:

[0143] Next, as shown in the above synthesis scheme (a-3-2-2), the phenyl group and Ar 1 The amine compound (compound 12) having a fluorene skeleton represented by the formula: 1 It is possible to obtain an amine compound (compound 7) having a fluorene skeleton represented by the following formula:

[0144] The above synthesis scheme (a-3-2-1) can be carried out using the Buchwald-Hartwig reaction using a palladium catalyst, as in the synthesis schemes (a-1) and (a-2). The above synthesis scheme (a-3-2-2) can be carried out using the Suzuki-Miyaura reaction using a palladium catalyst, as in the synthesis scheme (a-3-1).

[0145] The organic compound represented by the general formula (G1) can be synthesized according to the following synthesis schemes (a-5) and (a-6).

[0146] [ka]

[0147] [ka]

[0148] In the synthetic schemes (a-3) and (a-4), Q 1 and Q 2 R in Compound 1, Compound 2, Compound 4, and Compound 16 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. 1 ~R 22 , X, n, Ar 1 is the same as the organic compound represented by the general formula (G1). In addition, the above synthesis schemes (a-5) and (a-6) can be carried out using the Buchwald-Hartwig reaction using a palladium catalyst, similarly to the synthesis schemes (a-1) and (a-2).

[0149] In this synthetic scheme, first, as in the above synthetic scheme (a-5), an amine compound having a binaphthalene skeleton and a dibenzofuranylamine skeleton or a dibenzothiophenyl skeleton (compound 16) can be obtained by cross-coupling an amine compound having a dibenzofuran or dibenzothiophene skeleton (compound 2) with a compound having a binaphthalene skeleton (compound 4).

[0150] Next, according to the synthesis scheme (a-6), an amine compound having a binaphthalene skeleton and a dibenzofuranylamine skeleton or a dibenzothiophenyl skeleton (compound 16) and Ar 1 By cross-coupling a compound having a fluorene skeleton represented by the formula (Compound 1), a binaphthalene skeleton and Ar 1 In this way, an organic compound according to one embodiment of the present invention, which is represented by General Formula (G1) and which has a fluorene skeleton represented by the following formula, and further a dibenzofuran skeleton or a dibenzothiophene skeleton, can be obtained.

[0151] Compound 16 can also be synthesized as shown in the following synthetic scheme (a-5-1) using the amine compound having a binaphthalene skeleton (compound 10) synthesized in the above synthetic scheme (a-3-1) or (a-3-1-1).

[0152] [ka]

[0153] In the synthetic scheme (a-5-1), Q 3 represents a chlorine, bromine, iodine, or triflate group. R in Compound 6, Compound 10, and Compound 16 1 ~R 22 , X, and n are the same as those of the organic compound represented by the general formula (G1). In addition, the above synthesis scheme (a-5-1) can be carried out using the Buchwald-Hartwig reaction using a palladium catalyst, similarly to the synthesis schemes (a-1) and (a-2).

[0154] In the synthetic scheme (a-5-1), a compound having a dibenzofuran skeleton or a dibenzothiophene skeleton (compound 6) and an amine compound having a binaphthalene skeleton (compound 10) are cross-coupled to obtain an amine compound having a binaphthalene skeleton and a dibenzofuranylamine skeleton or a dibenzothiophenyl skeleton (compound 16).

[0155] Compound 16 can also be synthesized as shown in the following synthesis schemes (a-5-2) and (a-5-3).

[0156] [ka]

[0157] [ka]

[0158] In the synthetic schemes (a-5-2) and (a-5-3), Q 6 and Q 7 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. 1 ~R 22 each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; R 1 ~R 22 may be bonded to each other to form a ring, and in this case, the boron compound may be pinacolborane or the like. 1 ~R 22 , X, and n are the same as those of the organic compound represented by general formula (G1).

[0159] First, as in the above synthesis scheme (a-5-2), an amine compound having a dibenzofuran skeleton or a dibenzothiophene skeleton (compound 2) is cross-coupled with a boron compound having a phenyl group (compound 13) to obtain a dibenzofuranyl or dibenzothiophenylamine compound having a boronated phenyl group (compound 17).

[0160] Next, as shown in the above synthesis scheme (a-5-3), compound 17 is cross-coupled with a boron compound having a binaphthalene skeleton (compound 15) to obtain an amine compound having a binaphthalene skeleton and a dibenzofuranylamine skeleton or a dibenzothiophenyl skeleton (compound 16).

[0161] The above synthesis scheme (a-5-2) can be carried out using the Buchwald-Hartwig reaction using a palladium catalyst, as in the synthesis schemes (a-1) and (a-2). The above synthesis scheme (a-5-3) can be carried out using the Suzuki-Miyaura reaction using a palladium catalyst, as in the synthesis scheme (a-3-1).

[0162] Compound 17 can be synthesized according to the following synthesis scheme (a-5-2-1).

[0163] [ka]

[0164] In the synthetic scheme (a-5-2-1), Q 3 represents a chlorine, bromine, iodine, or triflate group. 1 ~R 11 each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; R 1 ~R 11 may be bonded to each other to form a ring, and in this case, the boron compound may be pinacolborane. 1 ~R 11 and X is the same as the organic compound represented by the general formula (G1). The synthesis scheme (a-5-2-1) can be carried out by using the Buchwald-Hartwig reaction using a palladium catalyst, as in the synthesis schemes (a-1) and (a-2).

[0165] In the synthetic scheme (a-5-2-1), a dibenzofuranyl or dibenzothiophenylamine compound having a boronated phenyl group (compound 17) can be obtained by cross-coupling a compound having a dibenzofuran skeleton or a dibenzothiophene skeleton (compound 6) with a boron compound having an aniline skeleton (compound 11).

[0166] The organic compound represented by the general formula (G1) can be prepared by the above synthesis scheme (a-1) or (a-1-1) using Ar 1 The compound can be synthesized by using a dibenzofuranylamine or dibenzothiophenylamine compound (compound 3) having a fluorene skeleton represented by the following synthesis schemes (a-7) and (a-8).

[0167] [ka]

[0168] [ka]

[0169] In the synthetic schemes (a-7) and (a-8), Q 8 and Q 9 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. 1 ~R 22 each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; R 1 ~R 22 may be bonded to each other to form a ring, and in this case, the boron compound may be pinacolborane. 1 ~R 22 , X, n, Ar 1 is the same as the organic compound represented by general formula (G1).

[0170] First, as shown in the above synthesis scheme (a-7), Ar 1 By cross-coupling a dibenzofuranylamine or dibenzothiophenylamine compound (compound 3) having a fluorene skeleton represented by the formula (I) with a benzene compound (compound 18), a dibenzofuran skeleton or a dibenzothiophene skeleton and an Ar 1 It is possible to obtain an amine compound having a fluorene skeleton represented by the following formula (compound 19).

[0171] Next, according to the above synthesis scheme (a-8), compound 19 is cross-coupled with a boron compound having a binaphthalene skeleton (compound 9) to obtain a compound having a binaphthalene skeleton and Ar 1 In this way, an organic compound according to one embodiment of the present invention, which is represented by General Formula (G1) and which has a fluorene skeleton represented by the following formula, and further a dibenzofuran skeleton or a dibenzothiophene skeleton, can be obtained.

[0172] The above synthesis scheme (a-7) can be carried out using the Buchwald-Hartwig reaction using a palladium catalyst, as in the synthesis schemes (a-1) and (a-2). The above synthesis scheme (a-8) can be carried out using the Suzuki-Miyaura reaction using a palladium catalyst, as in the synthesis scheme (a-3-1).

[0173] The organic compound represented by the general formula (G1) can be prepared by the above synthesis scheme (a-1) or (a-1-1) using Ar 1 The compound can be synthesized by using a dibenzofuranylamine or dibenzothiophenylamine compound (compound 3) having a fluorene skeleton represented by the following synthesis schemes (a-9) and (a-10).

[0174] [ka]

[0175] [ka]

[0176] In the synthetic schemes (a-9) and (a-10), Q 6 and Q 7 each independently represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group. 1 ~R 22 each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; R 1 ~R 22 may be bonded to each other to form a ring, and in this case, the boron compound may be pinacolborane. 1 ~R 22 , X, n, Ar 1 is the same as the organic compound represented by general formula (G1).

[0177] First, as shown in the above synthesis scheme (a-9), Ar 1A dibenzofuranylamine or dibenzothiophenylamine compound having a fluorene skeleton represented by the following formula (Compound 3) can be cross-coupled with a boron compound having a phenyl group (Compound 13) to obtain a dibenzofuranylamine or dibenzothiophenylamine compound having a boronated phenyl group (Compound 20).

[0178] Next, according to the above synthesis scheme (a-10), compound 20 is cross-coupled with a boron compound having a binaphthalene skeleton (compound 15) to obtain a compound having a binaphthalene skeleton and Ar 1 In this way, an organic compound according to one embodiment of the present invention, which is represented by General Formula (G1) and which has a fluorene skeleton represented by the following formula, and further a dibenzofuran skeleton or a dibenzothiophene skeleton, can be obtained.

[0179] The above synthesis scheme (a-9) can be carried out using the Buchwald-Hartwig reaction using a palladium catalyst, as in the synthesis schemes (a-1) and (a-2). The above synthesis scheme (a-10) can be carried out using the Suzuki-Miyaura reaction using a palladium catalyst, as in the synthesis scheme (a-3-1).

[0180] In the above manner, the organic compound of one embodiment of the present invention represented by General Formula (G1) can be obtained.

[0181] Specific examples of organic compounds that can be used as the secondary amine shown as compound 3 in the above synthesis scheme are shown below.

[0182] [ka]

[0183] [ka]

[0184] [ka]

[0185] [ka]

[0186] [ka]

[0187] [ka]

[0188] [ka]

[0189] [ka]

[0190] In addition, specific examples of organic compounds that can be used as the secondary amine shown as compound 7 in the above synthesis scheme are shown below.

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] In addition, specific examples of organic compounds that can be used as the secondary amine shown as compound 16 in the above synthesis scheme are shown below.

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] Specific examples of the organic compound of one embodiment of the present invention described in this embodiment include organic compounds represented by the following structural formulas (100) to (247) and (300) to (447).

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[0246] (Embodiment 2) In this embodiment, an organic semiconductor device according to one embodiment of the present invention will be described in detail.

[0247] FIG. 1 is a schematic diagram of a light-emitting device according to one embodiment of the present invention. The light-emitting device includes a first electrode 101 over an insulator 100, and an organic compound layer 103 between the first electrode 101 and a second electrode 102. The organic compound layer 103 includes at least one of the organic compounds represented by General Formulae (G1) to (G6) in Embodiment 1. The organic semiconductor device according to one embodiment of the present invention includes an active layer (a light-emitting layer 113 in a light-emitting device, a photoelectric conversion layer in a photosensor, or the like). The light-emitting layer 113 in the light-emitting device includes a luminescent center substance, and the luminescent center substance emits light when a voltage is applied between the first electrode 101 and the second electrode 102.

[0248] 1(A), the organic compound layer 103 preferably has functional layers such as a hole injection layer 111, a hole transport layer 112, an electron transport layer 114, and an electron injection layer 115. The organic compound layer 103 may also include functional layers other than the above-mentioned functional layers, such as a hole blocking layer, an electron blocking layer, an exciton blocking layer, and a charge generating layer. Conversely, any of the above-mentioned layers may not be provided.

[0249] Note that the organic compounds represented by any of General Formulae (G1) to (G6) in Embodiment 1 are preferably contained in a layer through which holes are transported, such as a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting layer.

[0250] In addition, in this embodiment, the first electrode 101 is described as an electrode including an anode, and the second electrode 102 is described as an electrode including a cathode, but this may be reversed. In addition, the first electrode 101 and the second electrode 102 are formed as a single layer structure or a laminated structure, and in the case of a laminated structure, a layer in contact with the organic compound layer 103 functions as an anode or a cathode. In the case of an electrode having a laminated structure, there is no restriction on the work function of layers other than the layer in contact with the organic compound layer 103, and materials can be selected according to required characteristics such as resistance value, processing convenience, reflectance, light transmittance, and stability.

[0251] The anode is preferably formed using a metal, alloy, conductive compound, or 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 (ITSO), 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 also be formed by applying a sol-gel method or the like. As an example of a method for forming indium oxide-zinc oxide, a method for forming indium oxide-zinc oxide by a sputtering method using a target in which 1 to 20 wt % of zinc oxide is added to indium oxide may be used. Indium oxide containing tungsten oxide and zinc oxide (IWZO) can also be formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide. Other materials used for the anode include, for example, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), aluminum (Al), or nitrides of metal materials (for example, titanium nitride). A layer formed by stacking these may also be used as the anode. For example, a film in which Al, Ti, and ITSO are stacked in this order on Ti is preferable because it has a good reflectance, is highly efficient, and can achieve high resolution of several thousand ppi. Alternatively, graphene can also be used as a material used for the anode. In addition, by using a composite material capable of forming the hole injection layer 111 described later as a layer in contact with the anode (typically a hole injection layer), it becomes possible to select an electrode material regardless of the work function.

[0252] The hole injection layer 111 is provided in contact with the anode and has a function of facilitating injection of holes into the organic compound layer 103. The hole injection layer 111 can be formed of a phthalocyanine compound such as phthalocyanine (abbreviation: HPc) or copper phthalocyanine (abbreviation: CuPc) or a phthalocyanine-based complex compound, an aromatic amine compound such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB) or 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), or a polymer compound such as poly(3,4-ethylenedioxythiophene) / (polystyrenesulfonic acid) (abbreviation: PEDOT / PSS), or the like.

[0253] The hole injection layer 111 may be formed of a substance having electron acceptor properties. As the substance having acceptor properties, an organic compound having an electron-withdrawing group (such as a halogen group or a cyano group) can be used, and examples of the substance 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, a cyano group, etc.) [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, transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide can be used.

[0254] In addition, the hole-injecting layer 111 is preferably formed using a composite material containing the above-mentioned material having an acceptor property and an organic compound having a hole-transporting property.

[0255] As the organic compound having a hole transporting property used in the composite material, various organic compounds such as aromatic amine compounds, heteroaromatic compounds, aromatic hydrocarbons, and polymer compounds (oligomers, dendrimers, polymers, etc.) can be used. Note that the organic compound having a hole transporting property used in the composite material is preferably 1×10 -6 cm 2 It is preferable that the organic compound has a hole mobility of 100 / Vs or more. The organic compound having hole transport properties used in the composite material is preferably a compound having a condensed aromatic hydrocarbon ring or a π-electron-rich heteroaromatic ring. As the condensed aromatic hydrocarbon ring, an anthracene ring, a naphthalene ring, etc. are preferable. As the π-electron-rich heteroaromatic ring, a condensed aromatic ring containing at least one of a pyrrole skeleton, a furan skeleton, and a thiophene skeleton in the ring is preferable, and specifically, a carbazole ring, a dibenzothiophene ring, or a ring in which an aromatic ring or a heteroaromatic ring is further condensed to the above rings is preferable.

[0256] Such organic compounds having hole transport properties preferably have any of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, the organic compounds may be aromatic amines having a substituent containing a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group. It is preferable that the organic compounds having hole transport properties are substances having an N,N-bis(4-biphenyl)amino group, because this allows the manufacture of a light-emitting device with a long life.

[0257] Specific examples of organic compounds having hole transport properties as described above 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)benzylamine (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-(dibenzothiophene-4-yl)phenyl]-4-amino-p-terphenyl ]-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: BBAαNβ NB-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: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl] 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)furan-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: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)furan-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 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(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-Dimethyl-9H-fluoren-2-yl)dibenzofuran-4-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]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF), N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-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.

[0258] As a material having a hole transporting property, other aromatic amine compounds such as N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), etc. can also be used. The organic compounds shown as General Formulae (G1) to (G6) in Embodiment 1 can also be suitably used.

[0259] 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.

[0260] Among substances having acceptor properties, organic compounds having acceptor properties are easy to use because they can be easily evaporated and formed into a film.

[0261] The hole transport layer 112 is formed by including an organic compound having a hole transport property. -6 cm 2 It is preferable that the hole mobility is 1 / Vs or more.

[0262] Examples of the material having hole transport properties include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluorene]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3-methylphenyl-4,4'-diaminobiphenyl (abbreviation: 3-methylphenyl) ... '-(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: PCBANB), 4,4'-Di(1-naphthyl)-4''-(9-phenyl Compounds with aromatic amine skeletons such as N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di( N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviation: BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,3'-Bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: βNCCP), 9-(3-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCmBP), 9-(4-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCBP), 9,9'-di-2-naphthyl-3,3'-9H,9'H-bicarbazole (abbreviation :BisβNCz), 9-(2-naphthyl)-9'-[1,1':4',1"-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-5'-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':4',1"- terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole, 9-phenyl-9'-(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole (abbreviation: PCCzTp), 9,9'-bis(triphenylene-2 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. Note that the substances given as examples of the materials having a hole-transporting property used in the composite material of the hole-injection layer 111 can also be preferably used as materials for the hole-transport layer 112. Note that the organic compounds represented by General Formulas (G1) to (G6) in Embodiment 1 can also be preferably used.

[0263] The luminescent center substance may be a fluorescent substance, a phosphorescent substance, a substance exhibiting thermally activated delayed fluorescence (TADF), or any other luminescent substance.

[0264] Examples of materials that can be used as the fluorescent substance in the light-emitting layer include the following: In addition, fluorescent substances other than these can also be used.

[0265] 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-( 10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert-butylperylene (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(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(biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA) , 9,10-bis(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(biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyrazol-2-yl)-1,1-diphenylquinacridone (abbreviation: DPQd), DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation Name: 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),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'-diphenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b ]naphtho[1,2-d]furan)-8-amine] (abbreviation: 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), etc. 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 and excellent luminous efficiency or reliability.

[0266] In addition, 5,9-diphenyl-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (abbreviation: DABNA1), 9-(diphenyl-3-yl)-N,N,5,11-tetraphenyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene-3-amine (abbreviation: DABNA2), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-N,N-diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine -7-amine (abbreviation: DPhA-tBu4DABNA), 2,12-di(tert-butyl)-N,N,5,9-tetra(4-tert-butylphenyl)-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine-7-amine (abbreviation: tBuDPhA-tBu4DABNA), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-7-methyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: Me-tBu4DABNA), N 7 ,N 7 ,N 13 ,N 13 Condensed heteroaromatic compounds containing nitrogen and boron, such as 5,9,11,15-octaphenyl-5H,9H,11H,15H-[1,4]benzazaborino[2,3,4-kl][1,4]benzazaborino[4',3',2':4,5][1,4]benzazaborino[3,2-b]phenazaborine-7,13-diamine (abbreviation: ν-DABNA) and 2-(4-tert-butylphenyl)benz[5,6]indolo[3,2,1-jk]benzo[b]carbazole (abbreviation: tBuPBibc), in particular compounds having a diaza-boranaphtho-anthracene skeleton, can be suitably used because they have a narrow emission spectrum and can emit blue light with good color purity.

[0267] In addition to these, 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: BBCz-G), 9,11-bis[3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: BBCz-Y) and the like can be preferably used.

[0268] When a phosphorescent substance is used as the light-emitting substance in the light-emitting layer, examples of the phosphorescent substance include the following materials.

[0269] Organometallic iridium complexes with a 4H-triazole skeleton, such as 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]) and tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]). , organometallic iridium complexes with 1H-triazole skeleton such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) and tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), fac-tris[1-(2,6-di isopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpim)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), tris(2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazol-2-yl-κN3}-4-cyano organometallic iridium complexes with an imidazole skeleton, such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC2)phenyl-κC]iridium(III) (abbreviation: [Ir(cb)3]), organometallic complexes with a benzimidazolidene skeleton, such as bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir(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 that exhibit blue phosphorescence and have a peak emission wavelength in the range of 450 nm to 520 nm.

[0270] 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 (2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]) and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]); organometallic iridium complexes having a pyrazine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]); 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-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mbfpypy-d3)]), [2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzo furo[2,3-b]pyridin-7-yl-κC]bis[5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC]iridium(III) (abbreviation: Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridin-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpy Iridium(III) (abbreviation: [Ir(ppy)2(mdppy)]), [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(5-methyl-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mdp Examples of such compounds include organometallic iridium complexes having a pyridine skeleton, such as [2-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy)]), and rare earth metal complexes, such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]). These are compounds that mainly exhibit green phosphorescence, and have a peak emission in the wavelength range from 500 nm to 600 nm. In addition, organometallic iridium complexes having a pyrimidine skeleton are particularly preferred because they are also remarkably excellent in reliability or luminous efficiency.

[0271] 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-triphenylpyrazinate)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’Organometallic iridium compounds with pyridine skeletons such as (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolinyl-κN]phenyl-κC]iridium(III) and (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolinyl-κN]phenyl-κC]iridium(III). In addition to iridium complexes, platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]) are examples of rare earth metal complexes. These are compounds that exhibit red phosphorescence and have a peak emission in the wavelength range from 600 nm to 700 nm. In addition, organometallic iridium complexes with a pyrazine skeleton can emit red light with good chromaticity.

[0272] In addition to the above-mentioned phosphorescent compounds, known phosphorescent compounds may be selected and used.

[0273] 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.

[0274] [ka]

[0275] 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 having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a heteroaromatic ring, 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.

[0276] [ka]

[0277] 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.

[0278] 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.

[0279] 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 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 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.

[0280] 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.

[0281] As the host material of the light-emitting layer, various carrier transporting materials such as a material having an electron transporting property and / or a material having a hole transporting property, or the above-mentioned TADF material can be used.

[0282] As the material having hole transport properties, preferred are organic compounds having an amine skeleton, a π-electron-rich heteroaromatic ring skeleton, etc. As the π-electron-rich heteroaromatic ring, preferred are condensed aromatic rings containing at least one of an acridine skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a furan skeleton, a thiophene skeleton, and a pyrrole skeleton, specifically preferred are carbazole rings, dibenzothiophene rings, or rings in which an aromatic ring or a heteroaromatic ring is further condensed to these rings.

[0283] Such organic compounds having hole transport properties preferably have any of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, the organic compounds may be aromatic amines having a substituent containing a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group. It is preferable that the organic compounds having hole transport properties are substances having an N,N-bis(4-biphenyl)amino group, because this allows the manufacture of a light-emitting device with a long life.

[0284] Examples of such organic compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: :BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation:mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: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 compounds such as 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]fluorene-2-amine (abbreviation: PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF) Compounds with aromatic amine skeletons, compounds with carbazole skeletons 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), 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 or compounds having a carbazole skeleton are preferable because they have good reliability, high hole transportability, and contribute to reducing the driving voltage. In addition, the organic compounds given as examples of materials having hole transportability in the hole transport layer can also be used. Note that the organic compounds represented by General Formulas (G1) to (G6) in Embodiment 1 can also be suitably used.

[0285] Materials with electron transport properties have an electron mobility of 1×10 at a square root of an electric field strength [V / cm] of 600. -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2 A substance having an electron mobility of 1 / Vs or more is preferable. Note that other substances can be used as long as they have a higher electron transporting property than a hole transporting property.

[0286] 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), and organic compounds having a π-electron-deficient heteroaromatic ring. Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include organic compounds containing a heteroaromatic ring having a polyazole skeleton, organic compounds containing a heteroaromatic ring having a pyridine skeleton, organic compounds containing a heteroaromatic ring having a diazine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton.

[0287] Among them, organic compounds containing a heteroaromatic ring having a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), organic compounds containing a heteroaromatic ring having a pyridine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton are preferable because of their good reliability. In particular, organic compounds containing a heteroaromatic ring having a diazine (pyrimidine or pyrazine) skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton have high electron transport properties and contribute to reducing the driving voltage. In addition, benzofuropyrimidine skeleton, benzothienopyrimidine skeleton, benzofuropyrazine skeleton, and benzothienopyrazine skeleton are preferable because of their high acceptor properties and good reliability.

[0288] 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-1,3,4-oxadiazole- Organic compounds with an azole skeleton, such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), )phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P), 2-[3-(2-triphenylenyl)phenyl]-1,10 -phenanthroline (abbreviation: mTpPPhen), 2-phenyl-9-(2-triphenylenyl)-1,10-phenanthroline (abbreviation: Ph-TpPhen), 2-[4-(9-phenanthrenyl)-1-naphthalenyl]-1,10-phenanthroline (abbreviation: PnNPhen), 2-[4-(2-triphenylenyl)phenyl]-1,10-phenanthroline (abbreviation: pTpPPhen), and other organic compounds containing heteroaromatic rings with a pyridine skeleton, such as 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 2-[4-(3,6-diphenyl 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNf pr), 9-[3'-(dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 9,9'-[pyrimidinyl 4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 8-(biphenyl-4-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4mDBtPBfpm), 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)(biphenyl-3-yl)]naphtho[1',2':4,5]furo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), 8-[(2,2'-binaphthalene)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm), 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2, 6(P-Bqn)2Py), 2,2'-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm)2Py), 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 2,6-bis(4-naphthalen-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 4-[3,5-bis(9H-carbazol-9 organic compounds with a diazine skeleton, such as 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluoren]-2-yl)-pyrimidine (abbreviation: 6BP-4Cz2PPm), 7-[4-(9-phenyl-9H-carbazol-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz), 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluoren]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d] 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole Rubazol (abbreviation: mINc(II)PTzn), 2-{3-[3-(dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mDBtBPTzn), 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: TmPPPyTz), 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-di Phenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazin-2-yl]-11,12-dihydro-12-phenyl-indolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), 2-[3'-(triphenylen-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 3 Examples of the organic compounds include organic compounds containing heteroaromatic rings having a triazine skeleton, such as -[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn) and 2-(biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',1''-terphenyl)-4-yl]-1-dibenzofuranyl}-1,3,5-triazine (abbreviation: mBP-TPDBfTzn). In addition, organic compounds containing heteroaromatic rings having a diazine skeleton, organic compounds containing heteroaromatic rings having a pyridine skeleton, and organic compounds containing heteroaromatic rings having a triazine skeleton are preferred because of their good reliability. In particular, organic compounds containing heteroaromatic rings having a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing heteroaromatic rings having a triazine skeleton have high electron transport properties and contribute to reducing the driving voltage.

[0289] 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.

[0290] 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.

[0291] 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.

[0292] 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 such luminophore include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, a phenothiazine skeleton, 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, and a naphthobisbenzofuran 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, and a naphthobisbenzofuran skeleton are preferred because they have a high fluorescence quantum yield.

[0293] When a fluorescent emitting material is used as the emitting material, a material having an acene skeleton, particularly 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 hole injection and transport properties are improved, but when the host material contains a benzocarbazole skeleton in which a benzene ring is further condensed to the carbazole skeleton, the HOMO level is about 0.1 eV higher than that of a host material having a carbazole skeleton, 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 level is about 0.1 eV higher than that of a host material having a carbazole skeleton, making it easier for holes to enter, and it also has excellent hole transport properties and high heat resistance. Therefore, a more preferable host material is a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). From the viewpoint of the hole injection / transport property, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton.

[0294] Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'- 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracen-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracenyl)benzo Zo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-{4-[10-(biphenyl-4-yl)-9-anthracenyl]phenyl}-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), etc. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred choices because they show very good properties.

[0295] The host material may be a mixture of a plurality of substances, and when a mixture of host materials is used, it is preferable to mix a material having an electron transporting property with a material having a hole transporting property. By mixing a material having an electron transporting property with a material having a hole transporting property, the transporting property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The weight ratio of the content of the material having a hole transporting property to the material having an electron transporting property (material having a hole transporting property:material having an electron transporting property) can be 1:19 to 19:1.

[0296] 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.

[0297] 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.

[0298] 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.

[0299] 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 (Lowest Unoccupied Molecular Orbital) 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.

[0300] 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.

[0301] The electron transport layer 114 is a layer containing a material having an electron transport property. The material having an electron transport property is a material having an electron mobility of 1×10 -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2 A substance having an electron mobility of 100 / Vs or more is preferable. Note that, other substances can be used as long as they have a higher transportability of electrons than holes. Note that, as the organic compound, an organic compound having a π-electron-deficient heteroaromatic ring is preferable. As the organic compound having a π-electron-deficient heteroaromatic ring, for example, it is preferable to use one or more of an organic compound having a heteroaromatic ring with a polyazole skeleton, an organic compound having a heteroaromatic ring with a pyridine skeleton, an organic compound having a heteroaromatic ring with a diazine skeleton, and an organic compound having a heteroaromatic ring with a triazine skeleton.

[0302] As the organic compound having electron transport properties that can be used in the electron transport layer 114, the organic compound that can be used as the organic compound having electron transport properties in the light emitting layer 113 can be used in the same way. Among them, organic compounds containing a heteroaromatic ring having a diazine skeleton, organic compounds containing a heteroaromatic ring having a pyridine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton are preferable because they have good reliability. In particular, organic compounds containing a heteroaromatic ring having a diazine (pyrimidine or pyrazine) skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton have high electron transport properties and contribute to reducing the driving voltage. In particular, organic compounds having a phenanthroline skeleton such as mTpPPhen, PnNPhen, and mPPhen2P are preferable, and organic compounds having a phenanthroline dimer structure such as mPPhen2P are more preferable because they have excellent stability.

[0303] The electron transport layer 114 may have a laminated structure. In addition, a layer in the electron transport layer 114 having a laminated structure that is in contact with the light-emitting layer 113 may function as a hole blocking layer. When the electron transport layer in contact with the light-emitting layer is made to function as a hole blocking layer, it is preferable to use a material whose HOMO level is 0.5 eV or more lower than the HOMO level of the material contained in the light-emitting layer 113.

[0304] The electron injection layer 115 may be a layer containing an alkali metal or alkaline earth metal compound or complex such as 8-hydroxyquinolinato-lithium (abbreviation: Liq), or 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviation: hpp2Py). The electron injection layer 115 may be a layer made of a substance having an electron transporting property containing an alkali metal or alkaline earth metal or a compound thereof.

[0305] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1(B)). The charge generation layer 116 is a layer capable of injecting holes into a layer in contact with the cathode side of the layer and electrons into a layer in contact with the anode side of the layer by applying a potential. The charge generation layer 116 includes at least a P-type layer 117. The P-type layer 117 is preferably formed using the composite material listed 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 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 with a low refractive index, a light-emitting device with good external quantum efficiency can be obtained by using the organic compound for the P-type layer 117.

[0306] In addition, the charge generating layer 116 preferably includes, in addition to the P-type layer 117, either or both of an electron relay layer 118 and an electron injection buffer layer 119.

[0307] 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.

[0308] 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)).

[0309] 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.

[0310] The second electrode 102 is an electrode including a cathode. The second electrode 102 may have a laminated structure, in which case the layer in contact with the organic compound layer 103 functions as the cathode. As a material for forming the cathode, a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less) can be used. Specific examples of such a cathode material include alkali metals such as lithium (Li) or 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 (MgAg, AlLi) and compounds (lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), etc.) containing these, rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these, etc. However, by providing the electron injection layer 115 or a thin film of the above-mentioned material with a small work function 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 cathode regardless of the magnitude of the work function.

[0311] When the second electrode 102 is formed using a material that is transparent to visible light, a light-emitting device that emits light from the second electrode 102 side can be obtained.

[0312] 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.

[0313] In addition, various methods can be used for forming the organic compound layer 103, regardless of whether it is a dry method or a wet method. For example, a vacuum deposition method, a gravure printing method, an offset printing method, a screen printing method, an inkjet method, a spin coating method, or the like may be used.

[0314] Moreover, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0315] Next, an embodiment of a light-emitting device having a structure in which a plurality of light-emitting units are stacked (also called a stacked device or a tandem device) will be described with reference to FIG. 1(C). This light-emitting device has a plurality of light-emitting units between an anode and a cathode. One light-emitting unit has a structure almost similar to that of the organic compound layer 103 shown in FIG. 1(A). In other words, it can be said that the light-emitting device shown in FIG. 1(C) is a light-emitting device having a plurality of light-emitting units, and the light-emitting device shown in FIG. 1(A) or FIG. 1(B) is a light-emitting device having one light-emitting unit.

[0316] In Fig. 1(C), a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between a first electrode 501 and a second electrode 502, and a charge generation layer 513 is provided between the first light-emitting unit 511 and the second light-emitting unit 512. The first electrode 501 and the second electrode 502 correspond to the first electrode 101 and the second electrode 102 in Fig. 1(A), respectively, and the same as those described in the description of Fig. 1(A) can be applied to them. In addition, the first light-emitting unit 511 and the second light-emitting unit 512 may have the same structure or different structures.

[0317] The charge generation layer 513 has a function of injecting electrons into one light-emitting unit and injecting holes into the other light-emitting unit when a voltage is applied between the first electrode 501 and the second electrode 502. That is, in FIG. 1C, when a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the charge generation layer 513 can inject electrons into the first light-emitting unit 511 and inject holes into the second light-emitting unit 512.

[0318] The charge generation layer 513 is preferably formed to have the same structure as the charge generation layer 116 described in FIG. 1B. A composite material of an organic compound and a metal oxide has excellent carrier injection and carrier transport properties, and therefore can realize low-voltage driving and low-current driving. When the anode side surface of the light-emitting unit is in contact with the charge generation layer 513, the charge generation layer 513 can also function as a hole injection layer of the light-emitting unit, and therefore the light-emitting unit does not need to be provided with a hole injection layer.

[0319] 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.

[0320] 1C, a light-emitting device having two light-emitting units has been described, but 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 generation layer 513 as in the light-emitting device according to this embodiment, it is possible to realize a device that can emit high-luminance light 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.

[0321] 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.

[0322] In addition, each layer and electrode such as the organic compound 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.

[0323] Next, an organic semiconductor device according to one embodiment of the present invention will be described.

[0324] 18 is a schematic diagram of a photosensor of one embodiment of the present invention. The photosensor includes a first electrode 101S over an insulator 100S and an organic compound layer 103S between the first electrode 101S and a second electrode 102S. The organic compound layer 103S includes at least a photoelectric conversion layer 123 and may further include a layer having a different function. The organic compound layer 103S includes the organic compound shown as General Formula (G1) in Embodiment 1.

[0325] The photoelectric conversion layer 123 is a layer that generates carriers and includes a p-type semiconductor and an n-type semiconductor. Charges are generated by light 124 incident on the photoelectric conversion layer 123, and can be extracted as a current.

[0326] In addition to the photoelectric conversion layer 123, the organic compound layer 103S preferably has functional layers such as a hole injection layer 111S, a hole transport layer 112S, an electron transport layer 114S, and an electron injection layer 115S, as shown in Fig. 18. The organic compound layer 103S may include a functional layer other than the functional layers described above. Conversely, any of the layers described above may not be provided.

[0327] Note that the organic compound represented by the general formula (G1) in the embodiment 1 is preferably contained in a layer through which holes are transported. Examples of the layer through which holes are transported include a hole injection layer, a hole transport layer, an electron blocking layer, and a photoelectric conversion layer.

[0328] In this embodiment, the first electrode 101S and the second electrode 102S are formed as a single layer structure or a laminated structure, and in the case of a laminated structure, the layer in contact with the organic compound layer 103 functions as an anode or a cathode. In the case of a laminated structure, there is no restriction on the work function of layers other than the layer in contact with the organic compound layer 103, and materials can be selected according to required characteristics such as resistance value, processing convenience, reflectance, light transmittance, and stability. The first electrode 101S and the second electrode 102S can be formed using the same material as the first electrode 101 and the second electrode 102. However, the electrode that takes in light is preferably formed using a material that is transparent to light of a wavelength that can be photoelectrically converted in the photoelectric conversion layer, more preferably has a transmittance of 50% or more, and further preferably has a transmittance of 70% or more. For the first electrode 101S and the second electrode 102S, the electrode that receives holes is preferably made of a material listed as being preferably used as an anode in a light-emitting device, and for the electrode that receives electrons is preferably made of a material listed as being preferably used as a cathode in a light-emitting device.

[0329] The hole injection layer 111S, the hole transport layer 112S, the electron transport layer 114S, the electron injection layer 115S, and other functional layers can be made of the same materials as those given as the materials for the functional layers constituting the light-emitting device. Note that the layer having a hole transport function preferably contains the organic compound of one embodiment of the present invention.

[0330] The photoelectric conversion layer 123 is a layer that generates carriers based on incident light and is a layer that includes a semiconductor. Examples of the semiconductor include inorganic semiconductors such as silicon, and organic semiconductors that include organic compounds. In this embodiment, an example in which an organic semiconductor is used as the semiconductor of the active layer is shown. By using an organic semiconductor, the light-emitting layer and the active layer can be formed by the same method (for example, vacuum deposition), and a common manufacturing device can be used, which is preferable.

[0331] Moreover, the photoelectric conversion layer 123 has at least a p-type semiconductor material and an n-type semiconductor material.

[0332] Examples of p-type semiconductor materials include electron-donating organic semiconductor materials such as copper (II) phthalocyanine (CuPc), tetraphenyldibenzoperiflanthene (DBP), zinc phthalocyanine (ZnPc), tin phthalocyanine (SnPc), and quinacridone.

[0333] Examples of p-type semiconductor materials include carbazole derivatives, thiophene derivatives, furan derivatives, and compounds having an aromatic amine skeleton. Examples of p-type semiconductor materials include naphthalene derivatives, anthracene derivatives, pyrene derivatives, triphenylene derivatives, fluorene derivatives, pyrrole derivatives, benzofuran derivatives, benzothiophene derivatives, indole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, indolocarbazole derivatives, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, quinacridone derivatives, polyphenylenevinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and polythiophene derivatives.

[0334] As n-type semiconductor materials, fullerenes (e.g., C 60 , C 70 Examples of electron-accepting organic semiconductor materials include organic semiconductor materials such as fullerene derivatives, etc. Fullerenes have a shape like a soccer ball, and this shape is energetically stable. Fullerenes have deep (low) HOMO and LUMO levels. Fullerenes have extremely high electron-accepting (acceptor) properties because of their deep LUMO level. Normally, when π-electron conjugation (resonance) spreads on a plane, as in benzene, electron-donating (donor) properties are high, but fullerenes have a spherical shape, so they have high electron-accepting properties despite the large spread of π-electron conjugation. High electron-accepting properties cause charge separation quickly and efficiently, making them useful as photoelectric conversion devices. C 60 , C 70Both have a wide absorption band in the visible light region, especially C 70 is C 60 It is preferred because it has a larger π-electron conjugated system and a wide absorption band in the long wavelength region compared to [6,6]-Phenyl-C 71 -butyric acid methyl ester (abbreviation: PC71BM), [6,6]-Phenyl-C 61 -butyric acid methyl ester (abbreviation: PC61BM), 1',1'',4',4''-Tetrahydro-di[1,4]methanonaphthaleno[1,2:2',3',56,60:2'',3''][5,6]fulrerene-C 60 (Abbreviation: ICBA) and others.

[0335] Examples of n-type semiconductor materials include metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline derivatives, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, naphthalene derivatives, anthracene derivatives, coumarin derivatives, rhodamine derivatives, triazine derivatives, and quinone derivatives.

[0336] Moreover, the photoelectric conversion layer 123 is preferably a laminated film of a first layer having a p-type semiconductor material and a second layer having an n-type semiconductor material.

[0337] In the light emitting devices having the above configurations, the photoelectric conversion layer 123 is preferably a mixed film having a p-type semiconductor material and an n-type semiconductor material.

[0338] The HOMO level of the electron-donating organic semiconductor material is preferably shallower (higher) than the HOMO level of the electron-accepting organic semiconductor material, and the LUMO level of the electron-donating organic semiconductor material is preferably shallower (higher) than the LUMO level of the electron-accepting organic semiconductor material.

[0339] In addition, a spherical fullerene may be used as the electron-accepting organic semiconductor material, and an organic semiconductor material with a nearly planar shape may be used as the electron-donating organic semiconductor material. Molecules with similar shapes tend to gather together, and when molecules of the same type aggregate, the energy levels of the molecular orbitals are close to each other, which can increase the carrier transportability.

[0340] In the light-emitting device and photosensor according to one embodiment of the present invention having the above-described structure, since the organic compound represented by the general formula (G1) is a material having good hole-transporting properties and high heat resistance, a device having low driving voltage and excellent reliability when driven at high temperatures can be provided by manufacturing a device using the organic compound. In addition, a thin film including an organic compound having such a structure is preferable because it has little change in film quality and can provide a device that is stable against heat or driving. In addition, a device using an organic compound having such a structure can provide a device that has low driving voltage, high reliability against voltage because of small voltage fluctuation during driving, and excellent reliability when driven at high temperatures. In addition, it is preferable because a device with low power consumption can be provided. In addition, an organic compound having such a structure is preferable in terms of manufacturing cost because it has high sublimability and does not decompose during a deposition process and can be produced stably.

[0341] (Embodiment 3) In this embodiment, an embodiment in which an organic semiconductor device according to one embodiment of the present invention is a light-emitting device that can be used as a display device of a display device will be described. Note that, although an example in which an organic compound layer of a light-emitting device is patterned by a photolithography method is shown in this embodiment, a light-emitting device may be formed by a conventional method such as mask deposition.

[0342] As shown in FIGS. 2A and 2B, a plurality of light emitting devices 130 are formed on an insulating layer 175 to constitute a display device.

[0343] The display device has a pixel portion 177 in which a plurality of pixels 178 are arranged in a matrix. The pixel 178 has a sub-pixel 110R, a sub-pixel 110G, and a sub-pixel 110B.

[0344] In this specification and the like, when describing matters common to, for example, the subpixels 110R, 110G, and 110B, they may be referred to as subpixels 110. When describing matters common to other components distinguished by alphabets, they may be described using symbols without the alphabets.

[0345] The sub-pixel 110R emits red light, the sub-pixel 110G emits green light, and the sub-pixel 110B emits blue light. This allows an image to be displayed in the pixel section 177. In the present embodiment, sub-pixels of three colors, red (R), green (G), and blue (B), are described as an example, but combinations of sub-pixels of other colors may be used. The number of sub-pixels is not limited to three, and may be four or more. Examples of the four sub-pixels include sub-pixels of four colors, R, G, B, and white (W), sub-pixels of four colors, R, G, B, and yellow (Y), and sub-pixels of R, G, B, and infrared (IR).

[0346] In this specification and the like, the row direction may be referred to as the X direction, and the column direction may be referred to as the Y direction. The X direction and the Y direction intersect, for example, perpendicularly.

[0347] 2A shows an example in which subpixels of different colors are arranged side by side in the X direction, and subpixels of the same color are arranged side by side in the Y direction. Note that subpixels of different colors may be arranged side by side in the Y direction, and subpixels of the same color may be arranged side by side in the X direction.

[0348] A connection portion 140 and a region 141 may be provided outside the pixel portion 177. The region 141 is provided between the pixel portion 177 and the connection portion 140. The region 141 is provided with an organic compound layer 103. In addition, the connection portion 140 is provided with a conductive layer 151C.

[0349] 2A shows an example in which the region 141 and the connection portion 140 are located on the right side of the pixel portion 177, but the positions of the region 141 and the connection portion 140 are not particularly limited. The region 141 and the connection portion 140 may be singular or plural.

[0350] Fig. 2(B) is an example of a cross-sectional view between dashed line A1-A2 in Fig. 2(A). As shown in Fig. 2(B), the display device has an insulating layer 171, a conductive layer 172 on the insulating layer 171, an insulating layer 173 on the insulating layer 171 and on the conductive layer 172, an insulating layer 174 on the insulating layer 173, and an insulating layer 175 on the insulating layer 174. The insulating layer 171 is provided on a substrate (not shown). An opening reaching the conductive layer 172 is provided in the insulating layer 175, the insulating layer 174, and the insulating layer 173, and a plug 176 is provided to fill the opening.

[0351] In the pixel section 177, the light emitting device 130 is provided on the insulating layer 175 and the plug 176. A protective layer 131 is provided so as to cover the light emitting device 130. The substrate 120 is bonded onto the protective layer 131 by a resin layer 122. In addition, an inorganic insulating layer 125 and an insulating layer 127 on the inorganic insulating layer 125 are preferably provided between adjacent light emitting devices 130.

[0352] 2B shows multiple cross sections of the inorganic insulating layer 125 and the insulating layer 127, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are connected to one another when the display device is viewed from above. In other words, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are insulating layers having an opening over the first electrode.

[0353] In FIG. 2B, the light emitting device 130 includes a light emitting device 130R, a light emitting device 130G, and a light emitting device 130B. The light emitting device 130R, the light emitting device 130G, and the light emitting device 130B emit light of different colors. For example, the light emitting device 130R can emit red light, the light emitting device 130G can emit green light, and the light emitting device 130B can emit blue light. The light emitting device 130R, the light emitting device 130G, or the light emitting device 130B may emit other visible light or infrared light. In FIG. 2B, the light emitting device 130R and the light emitting device 130G, and the light emitting device 130G and the light emitting device 130B can be said to be adjacent light emitting devices.

[0354] The display device of one embodiment of the present invention can be, for example, a top emission type that emits light in a direction opposite to a substrate on which a light-emitting device is formed. Note that the display device of one embodiment of the present invention may be a bottom emission type.

[0355] The light-emitting device 130R is a light-emitting device that emits red light (preferably phosphorescence), and preferably has a configuration as shown in embodiment 1 or embodiment 2. The light-emitting device 130R has a first electrode 101R (pixel electrode) composed of a conductive layer 151R and a conductive layer 152R, a first layer 135R on the first electrode, a common layer 136 on the first layer 135R, and a second electrode (common electrode) 102 on the common layer 136. The common layer 136 is preferably an electron injection layer.

[0356] Light-emitting device 130G is a light-emitting device that emits green light (preferably phosphorescence), and preferably has a configuration as shown in embodiment 1 or embodiment 2. Light-emitting device 130G has a first electrode 101G (pixel electrode) composed of conductive layer 151G and conductive layer 152G, a first layer 135G on the first electrode, a common layer 136 on the first layer 135G, and a second electrode (common electrode) 102 on the common layer 136. Common layer 136 is preferably an electron injection layer.

[0357] Light-emitting device 130B is a light-emitting device that emits blue light (preferably fluorescent light) and preferably has a configuration as shown in embodiment 1 or embodiment 2. It has a first electrode 101B (pixel electrode) consisting of conductive layer 151B and conductive layer 152B, a first layer 135B on the first electrode, a common layer 136 on the first layer 135B, and a second electrode (common electrode) 102 on the common layer 136. The common layer 136 is preferably an electron injection layer.

[0358] One of a pixel electrode (first electrode) and a common electrode (second electrode) of a light-emitting device functions as an anode, and the other functions as a cathode. In this embodiment, unless otherwise specified, the pixel electrode functions as an anode, and the common electrode functions as a cathode.

[0359] The first layer 135R, the first layer 135G, and the first layer 135B are independent in an island shape for each light-emitting device or for each light-emitting color. It is also preferable that the first layer 135R, the first layer 135G, and the first layer 135B do not overlap each other. The first layer 135R, the first layer 135G, and the first layer 135B, which are included in the plurality of light-emitting devices 130 formed in the light-emitting device, may be collectively referred to as the first layer group 135A. By providing the first layer group 135A in an island shape for each light-emitting device 130, it is possible to suppress the leakage current between adjacent light-emitting devices 130 even in a high-definition display device. This makes it possible to prevent crosstalk and realize a display device with extremely high contrast. In particular, it is possible to realize a display device with high current efficiency at low luminance.

[0360] The island-shaped first layer group 135A is formed by depositing an EL film for each emitted color and processing the EL film by photolithography.

[0361] The first layer 135 is preferably provided so as to cover the upper surface and side surfaces of the first electrode 101 (pixel electrode) of the light-emitting device 130. This makes it easier to increase the aperture ratio of the display device compared to a configuration in which the end of the first layer 135 is located inside the end of the pixel electrode. In addition, by covering the side surfaces of the pixel electrode of the light-emitting device 130 with the first layer 135, contact between the first electrode 101 and the second electrode 102 can be prevented, and therefore short-circuiting of the light-emitting device 130 can be prevented.

[0362] In the display device of one embodiment of the present invention, the first electrode 101 (pixel electrode) of the light-emitting device preferably has a stacked structure. For example, in the example shown in FIG. 2B, the first electrode 101 of the light-emitting device 130 has a stacked structure of a conductive layer 151 provided on the insulating layer 171 side and a conductive layer 152 provided on the organic compound layer side.

[0363] For example, a metal material can be used as the conductive layer 151. Specifically, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd), and alloys containing appropriate combinations of these metals can also be used.

[0364] The conductive layer 152 can be made of an oxide containing one or more selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon. For example, it is preferable to use a conductive oxide containing one or more of indium oxide, indium tin oxide, indium zinc oxide, zinc oxide, zinc oxide containing gallium, titanium oxide, indium zinc oxide containing gallium, indium zinc oxide containing aluminum, indium tin oxide containing silicon, and indium zinc oxide containing silicon. In particular, indium tin oxide containing silicon has a large work function, for example, a work function of 4.0 eV or more, and therefore can be suitably used for the conductive layer 152.

[0365] The conductive layer 151 may have a stacked structure of multiple layers having different materials, and the conductive layer 152 may have a stacked structure of multiple layers having different materials. In this case, the conductive layer 151 may have a layer using a material that can be used for the conductive layer 152, such as a conductive oxide, or the conductive layer 152 may have a layer using a material that can be used for the conductive layer 151, such as a metal material. For example, when the conductive layer 151 has a stacked structure of two or more layers, a layer in contact with the conductive layer 152 can be a layer using a material that can be used for the conductive layer 152.

[0366] Note that an end portion of the conductive layer 151 preferably has a tapered shape. Specifically, an end portion of the conductive layer 151 preferably has a tapered shape with a taper angle of less than 90°. In this case, the conductive layer 152 provided along the side surface of the conductive layer 151 also has a tapered shape. By making the end portion of the conductive layer 152 have a tapered shape, the coverage of the first layer 135 provided along the side surface of the conductive layer 152 can be improved.

[0367] Next, an example of a method for manufacturing a display device having the structure shown in FIG. 2A will be described with reference to FIGS.

[0368] [Example of manufacturing method] The thin films (insulating films, semiconductor films, conductive films, etc.) that constitute the display device can be formed using a sputtering method, a chemical vapor deposition (CVD) method, a vacuum deposition method, a pulsed laser deposition (PLD) method, an ALD method, or the like.

[0369] Furthermore, the thin films (insulating films, semiconductor films, conductive films, etc.) constituting the display device can be formed by wet film formation methods such as spin coating, dipping, spray coating, inkjet, dispensing, screen printing, offset printing, doctor knife method, slit coating, roll coating, curtain coating, or knife coating.

[0370] Furthermore, when processing the thin films that constitute the display device, they can be processed using, for example, a photolithography method.

[0371] In the photolithography method, the light used for exposure may be, for example, i-line (wavelength 365 nm), g-line (wavelength 436 nm), h-line (wavelength 405 nm), or a mixture of these. In addition, ultraviolet light, KrF laser light, ArF laser light, etc. may also be used. Exposure may also be performed by immersion exposure technology. Extreme ultraviolet (EUV) light or X-rays may also be used as the light used for exposure. An electron beam may also be used instead of the light used for exposure.

[0372] The thin film can be etched by dry etching, wet etching, sandblasting, or the like.

[0373] 3A, an insulating layer 171 is formed on a substrate (not shown). Then, a conductive layer 172 and a conductive layer 179 are formed on the insulating layer 171, and an insulating layer 173 is formed on the insulating layer 171 so as to cover the conductive layer 172 and the conductive layer 179. Then, an insulating layer 174 is formed on the insulating layer 173, and an insulating layer 175 is formed on the insulating layer 174.

[0374] The substrate may be a substrate having at least a heat resistance sufficient to withstand a subsequent heat treatment, such as a glass substrate, a quartz substrate, a sapphire substrate, a ceramic substrate, an organic resin substrate, a single crystal semiconductor substrate made of silicon, silicon carbide, or the like, a polycrystalline semiconductor substrate, a compound semiconductor substrate made of silicon germanium, or the like, or an SOI substrate.

[0375] 3A, an opening reaching the conductive layer 172 is formed in the insulating layer 175, the insulating layer 174, and the insulating layer 173. Then, a plug 176 is formed to fill the opening.

[0376] 3A, a conductive film 151f, which will later become the conductive layers 151R, 151G, 151B, and 151C, is formed on the plugs 176 and the insulating layer 175. The conductive film 151f can be made of, for example, a metal material.

[0377] 3A, a resist mask 191 is formed over the conductive film 151f. The resist mask 191 can be formed by applying a photosensitive material (photoresist) and then performing exposure and development.

[0378] 3B, for example, the conductive film 151f is removed from a region that does not overlap with the resist mask 191. In this way, the conductive layer 151 is formed.

[0379] 3C, the resist mask 191 is removed. The resist mask 191 can be removed by ashing using oxygen plasma, for example.

[0380] Next, as shown in FIG. 3(D), an insulating film 156f, which will later become insulating layers 156R, 156G, 156B, and 156C, is formed on conductive layer 151R, conductive layer 151G, conductive layer 151B, conductive layer 151C, and insulating layer 175.

[0381] The insulating film 156f can be an inorganic insulating film such as an insulating oxide film, a nitride insulating film, an oxynitride insulating film, or a nitride oxide insulating film, for example, a silicon oxynitride film.

[0382] Subsequently, as shown in FIG. 3(E), the insulating film 156f is processed to form an insulating layer 156R, an insulating layer 156G, an insulating layer 156B, and an insulating layer 156C.

[0383] Next, as shown in FIG. 4(A), a conductive film 152f is formed on the conductive layer 151R, the conductive layer 151G, the conductive layer 151B, the conductive layer 151C, the insulating layer 156R, the insulating layer 156G, the insulating layer 156B, the insulating layer 156C, and the insulating layer 175.

[0384] The conductive film 152f may be, for example, a conductive oxide, or may be a multilayer film.

[0385] Subsequently, as shown in FIG. 4B, the conductive film 152f is processed to form a conductive layer 152R, a conductive layer 152G, a conductive layer 152B, and a conductive layer 152C.

[0386] 4(C), the organic compound film 103Rf is formed on the conductive layer 152R, the conductive layer 152G, the conductive layer 152B, and the insulating layer 175. Note that, as shown in FIG. 4(C), the organic compound film 103Rf is not formed on the conductive layer 152C.

[0387] Subsequently, as shown in FIG. 4(C), a sacrificial film 158Rf and a mask film 159Rf are formed.

[0388] By providing the sacrificial film 158Rf on the organic compound film 103Rf, damage to the organic compound film 103Rf during the manufacturing process of the display device can be reduced, and the reliability of the light-emitting device can be improved.

[0389] The sacrificial film 158Rf is made of a film having high resistance to the processing conditions of the organic compound film 103Rf, specifically, a film having a high etching selectivity with respect to the organic compound film 103Rf. The mask film 159Rf is made of a film having a high etching selectivity with respect to the sacrificial film 158Rf.

[0390] The sacrificial film 158Rf and the mask film 159Rf are formed at a temperature lower than the heat-resistant temperature of the organic compound film 103Rf. The substrate temperature when forming the sacrificial film 158Rf and the mask film 159Rf is typically 100° C. or higher and 200° C. or lower, preferably 100° C. or higher and 150° C. or lower, and more preferably 100° C. or higher and 120° C. or lower.

[0391] The sacrificial film 158Rf and the mask film 159Rf are preferably made of a film that can be removed by wet etching or dry etching.

[0392] In addition, the sacrificial film 158Rf formed on and in contact with the organic compound film 103Rf is preferably formed using a formation method that causes less damage to the organic compound film 103Rf than the mask film 159Rf. For example, the ALD method (Atomic Layer Deposition method) or the vacuum deposition method is more preferable than the sputtering method.

[0393] The sacrificial film 158Rf and the mask film 159Rf may each be made of one or more of a metal film, an alloy film, a metal oxide film, a semiconductor film, an organic insulating film, and an inorganic insulating film, for example.

[0394] The sacrificial film 158Rf and the mask film 159Rf may be made of, for example, a metal material such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, or tantalum, or an alloy material containing the metal material. In particular, it is preferable to use a low melting point material such as aluminum or silver. It is preferable to use a metal material capable of blocking ultraviolet rays for one or both of the sacrificial film 158Rf and the mask film 159Rf, since it is possible to suppress irradiation of ultraviolet rays during pattern exposure to the organic compound film 103Rf, and thus to suppress deterioration of the organic compound film 103Rf.

[0395] Furthermore, for the sacrificial film 158Rf and the mask film 159Rf, metal oxides such as In-Ga-Zn oxide, indium oxide, In-Zn oxide, In-Sn oxide, indium titanium oxide (In-Ti oxide), indium tin zinc oxide (In-Sn-Zn oxide), indium titanium zinc oxide (In-Ti-Zn oxide), indium gallium tin zinc oxide (In-Ga-Sn-Zn oxide), and indium tin oxide containing silicon can be used.

[0396] In addition, in the above metal oxide, an element M (M is one or more elements selected from aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium) may be used instead of gallium.

[0397] For the sacrificial film 158Rf and the mask film 159Rf, it is preferable to use a semiconductor material such as silicon or germanium because it has a high affinity with the semiconductor manufacturing process, or a compound containing the above semiconductor material may be used.

[0398] Moreover, various inorganic insulating films can be used as the sacrificial film 158Rf and the mask film 159Rf, respectively. In particular, an oxide insulating film is preferable because it has higher adhesion to the organic compound film 103Rf than a nitride insulating film.

[0399] 4(C), a resist mask 190R is formed. The resist mask 190R can be formed by applying a photosensitive material (photoresist) and then performing exposure and development.

[0400] The resist mask 190R is provided in a position overlapping with the conductive layer 152R. The resist mask 190R is preferably provided also in a position overlapping with the conductive layer 152C, which can prevent the conductive layer 152C from being damaged during the manufacturing process of the display device.

[0401] 4(D), a resist mask 190R is used to remove a portion of the mask film 159Rf to form a mask layer 159R. The mask layer 159R remains on the conductive layer 152R and the conductive layer 152C. The resist mask 190R is then removed. The mask layer 159R is then used as a mask (also called a hard mask) to remove a portion of the sacrificial film 158Rf to form a sacrificial layer 158R.

[0402] By using the wet etching method, damage to the organic compound film 103Rf during processing of the sacrificial film 158Rf and the mask film 159Rf can be reduced compared to the case of using the dry etching method. When using the wet etching method, it is preferable to use an acid aqueous solution such as a developing solution, an alkaline aqueous solution such as a tetramethylammonium hydroxide (TMAH) aqueous solution, a chemical solution using dilute hydrofluoric acid, oxalic acid, phosphoric acid, acetic acid, nitric acid, or a mixture of these.

[0403] Furthermore, when dry etching is used in processing the sacrificial film 158Rf, deterioration of the organic compound film 103Rf can be suppressed by not using an oxygen-containing gas as an etching gas.

[0404] The resist mask 190R can be removed in the same manner as the resist mask 191.

[0405] 4(D), the organic compound film 103Rf is processed to form a first layer 135R. For example, the mask layer 159R and the sacrificial layer 158R are used as a hard mask to remove a part of the organic compound film 103Rf to form the first layer 135R.

[0406] 4D, a laminated structure of the first layer 135R, the sacrificial layer 158R, and the mask layer 159R remains on the conductive layer 152R. Also, the conductive layers 152G and 152B are exposed.

[0407] The organic compound film 103Rf is preferably processed by anisotropic etching, particularly anisotropic dry etching, or wet etching may be used.

[0408] When dry etching is used, deterioration of the organic compound film 103Rf can be suppressed by not using an oxygen-containing gas as an etching gas.

[0409] Moreover, a gas containing oxygen may be used as the etching gas. When the etching gas contains oxygen, the etching speed can be increased. Therefore, etching can be performed under low power conditions while maintaining a sufficiently high etching speed. This makes it possible to suppress damage to the organic compound film 103Rf. Furthermore, problems such as adhesion of reaction products generated during etching can be suppressed.

[0410] When using a dry etching method, it is preferable to use a gas containing one or more of H2, CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, or a group 18 element such as He or Ar as an etching gas. Alternatively, it is preferable to use a gas containing one or more of these elements and oxygen as an etching gas. Alternatively, oxygen gas may be used as an etching gas.

[0411] Subsequently, as shown in FIG. 5A, an organic compound film 103Gf which will later become a first layer 135G is formed.

[0412] The organic compound film 103Gf can be formed by the same method as that used for forming the organic compound film 103Rf, and can have the same configuration as the organic compound film 103Rf.

[0413] 5(A), a sacrificial film 158Gf and a mask film 159Gf are formed in this order. Then, a resist mask 190G is formed. The materials and forming methods of the sacrificial film 158Gf and the mask film 159Gf are the same as those applicable to the sacrificial film 158Rf and the mask film 159Rf. The materials and forming methods of the resist mask 190G are the same as those applicable to the resist mask 190R.

[0414] The resist mask 190G is provided in a position overlapping with the conductive layer 152G.

[0415] 5(B), a part of the mask film 159Gf is removed using a resist mask 190G to form a mask layer 159G. The mask layer 159G remains on the conductive layer 152G. Then, the resist mask 190G is removed. Then, a part of the sacrificial film 158Gf is removed using the mask layer 159G as a mask to form a sacrificial layer 158G. Then, the organic compound film 103Gf is processed to form a first layer 135G.

[0416] Subsequently, as shown in FIG. 5(C), an organic compound film 103Bf is formed.

[0417] The organic compound film 103Bf can be formed by the same method as that used for forming the organic compound film 103Rf, and can have the same configuration as the organic compound film 103Rf.

[0418] 5(C), a sacrificial film 158Bf and a mask film 159Bf are formed in this order. Then, a resist mask 190B is formed. The material and the forming method of the sacrificial film 158Bf and the mask film 159Bf are the same as those applicable to the sacrificial film 158Rf and the mask film 159Rf. The material and the forming method of the resist mask 190B are the same as those applicable to the resist mask 190R.

[0419] The resist mask 190B is provided in a position overlapping with the conductive layer 152B.

[0420] 5(D), a part of the mask film 159Bf is removed using a resist mask 190B to form a mask layer 159B. The mask layer 159B remains on the conductive layer 152B. Then, the resist mask 190B is removed. Then, a part of the sacrificial film 158Bf is removed using the mask layer 159B as a mask to form a sacrificial layer 158B. Then, the organic compound film 103Bf is processed to form a first layer 135B. For example, a part of the organic compound film 103Bf is removed using the mask layer 159B and the sacrificial layer 158B as a hard mask to form a first layer 135B.

[0421] 5(D), a laminated structure of the first layer 135B, the sacrificial layer 158B, and the mask layer 159B remains on the conductive layer 152B. Also, the mask layers 159R and 159G are exposed.

[0422] It is preferable that the side surfaces of the first layer 135R, the first layer 135G, and the first layer 135B are perpendicular or approximately perpendicular to the surface on which the layers are to be formed. For example, it is preferable that the angle between the surface on which the layers are to be formed and these side surfaces is 60 degrees or more and 90 degrees or less.

[0423] As described above, the distance between two adjacent ones of the first layer 135R, the first layer 135G, and the first layer 135B formed by photolithography can be narrowed to 8 μm or less, 5 μm or less, 3 μm or less, 2 μm or less, or 1 μm or less. Here, the distance can be defined, for example, as the distance between two adjacent opposing ends of the first layer 135R, the first layer 135G, and the first layer 135B. In this way, by narrowing the distance between the island-shaped organic compound layers, a display device having high definition and a large aperture ratio can be provided. In addition, the distance between the first electrodes between adjacent light-emitting devices can also be narrowed, and can be, for example, 10 μm or less, 8 μm or less, 5 μm or less, 3 μm or less, or 2 μm or less. Note that the distance between the first electrodes between adjacent light-emitting devices is preferably 2 μm or more and 5 μm or less.

[0424] Next, as shown in FIG. 6(A), it is preferable to remove the mask layers 159R, 159G, and 159B.

[0425] The mask layer removal process can be performed using the same method as the mask film processing process. In particular, by using a wet etching method, damage to the first layer 135 during removal of the mask layer can be reduced compared to the case of using a dry etching method.

[0426] The mask layer may also be removed by dissolving it in a polar solvent such as water or alcohol, such as ethyl alcohol, methyl alcohol, isopropyl alcohol (IPA), or glycerin.

[0427] After removing the mask layer, a drying treatment may be performed to remove water adsorbed on the surface. For example, a heat treatment can be performed in an inert gas atmosphere or a reduced pressure atmosphere. The heat treatment can be performed at a substrate temperature of 50° C. to 200° C., preferably 60° C. to 150° C., and more preferably 70° C. to 120° C. A reduced pressure atmosphere is preferable because it allows drying at a lower temperature.

[0428] Subsequently, as shown in FIG. 6(B), an inorganic insulating film 125f is formed.

[0429] Subsequently, as shown in FIG. 6(C), an insulating film 127f, which will later become the insulating layer 127, is formed on the inorganic insulating film 125f.

[0430] The substrate temperature when forming the inorganic insulating film 125f and the insulating film 127f is preferably 60°C or more, 80°C or more, 100°C or more, or 120°C or more, and 200°C or less, 180°C or less, 160°C or less, 150°C or less, or 140°C or less.

[0431] As the inorganic insulating film 125f, it is preferable to form an insulating film having a thickness of 3 nm or more, 5 nm or more, or 10 nm or more and 200 nm or less, 150 nm or less, 100 nm or less, or 50 nm or less within the above substrate temperature range.

[0432] The inorganic insulating film 125f is preferably formed by, for example, the ALD method. By using the ALD method, damage during film formation can be reduced, and a film with high coverage can be formed, which is preferable. As the inorganic insulating film 125f, for example, an aluminum oxide film is preferably formed by the ALD method.

[0433] The insulating film 127f is preferably formed by using the above-mentioned wet film formation method. The insulating film 127f is preferably formed by using a photosensitive material, for example, by spin coating, and more specifically, is preferably formed by using a photosensitive resin composition containing an acrylic resin.

[0434] Subsequently, exposure is performed to expose a part of the insulating film 127f to visible light or ultraviolet light. The insulating layer 127 is formed in a region sandwiched between any two of the conductive layers 152R, 152G, and 152B, and around the conductive layer 152C.

[0435] The width of the insulating layer 127 to be formed later can be controlled by the exposed region of the insulating film 127f. In this embodiment, the insulating layer 127 is processed so as to have a portion overlapping with the upper surface of the conductive layer 151.

[0436] The light used for exposure preferably contains i-line (wavelength 365 nm), and may contain at least one of g-line (wavelength 436 nm) and h-line (wavelength 405 nm).

[0437] Subsequently, as shown in FIG. 7(A), development is performed to remove the exposed area of ​​the insulating film 127f, thereby forming an insulating layer 127a.

[0438] 7(B), an etching process is performed using the insulating layer 127a as a mask to remove a part of the inorganic insulating film 125f and to thin the thickness of the sacrificial layers 158R, 158G, and 158B. As a result, the inorganic insulating layer 125 is formed under the insulating layer 127a. In addition, the surfaces of the thin parts of the sacrificial layers 158R, 158G, and 158B are exposed. In the following, the etching process using the insulating layer 127a as a mask may be referred to as the first etching process.

[0439] The first etching process can be performed by dry etching or wet etching. Note that, when the inorganic insulating film 125f is formed using the same material as the sacrificial layers 158R, 158G, and 158B, the first etching process can be performed at once, which is preferable.

[0440] When dry etching is performed, it is preferable to use a chlorine-based gas. As the chlorine-based gas, Cl2, BCl3, SiCl4, CCl4, etc. can be used alone or in a mixture of two or more gases. In addition, oxygen gas, hydrogen gas, helium gas, argon gas, etc. can be appropriately added alone or in a mixture of two or more gases to the chlorine-based gas. By using dry etching, the thin film regions of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B can be formed with good in-plane uniformity.

[0441] As the dry etching apparatus, a dry etching apparatus having a high density plasma source can be used. As the dry etching apparatus having a high density plasma source, for example, an inductively coupled plasma (ICP) etching apparatus can be used. Alternatively, a capacitively coupled plasma (CCP) etching apparatus having parallel plate electrodes can be used.

[0442] In addition, it is preferable to perform the first etching process by wet etching. By using the wet etching method, damage to the first layer 135R, the first layer 135G, and the first layer 135B can be reduced compared to the case of using the dry etching method. For example, the wet etching can be performed using an alkaline solution. For example, an alkaline solution, TMAH, can be used for wet etching of an aluminum oxide film. Also, an acid solution containing fluoride can be used. In this case, the wet etching can be performed by the paddle method. Note that, when the inorganic insulating film 125f is formed using the same material as the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B, the above-mentioned etching process can be performed at once, which is preferable.

[0443] In the first etching process, the sacrificial layers 158R, 158G, and 158B are not completely removed, and the etching process is stopped when the film thickness becomes thin. In this manner, by leaving the corresponding sacrificial layers 158R, 158G, and 158B on the first layers 135R, 135G, and 135B, it is possible to prevent the first layers 135R, 135G, and 135B from being damaged in the processing of the subsequent process.

[0444] Next, the entire substrate is exposed to light, and it is preferable to irradiate the insulating layer 127a with visible light or ultraviolet light. The energy density of the exposure is 0 mJ / cm 2 Larger, 800mJ / cm2 It is preferable to set the concentration to 0 mJ / cm or less. 2 Larger than 500mJ / cm 2 It is more preferable to set the following. By performing such exposure after development, the transparency of the insulating layer 127a can be improved in some cases. In addition, the substrate temperature required for a heat treatment for transforming the insulating layer 127a into a tapered shape in a later step can be reduced in some cases.

[0445] Here, the presence of a barrier insulating layer against oxygen (e.g., an aluminum oxide film, etc.) as sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B can suppress the diffusion of oxygen into first layer 135R, first layer 135G, and first layer 135B.

[0446] Next, heat treatment (also referred to as post-baking) is performed. By performing heat treatment, the insulating layer 127a can be transformed into the insulating layer 127 having tapered sides (FIG. 7C). The heat treatment is performed at a temperature lower than the heat resistance temperature of the organic compound layer. The heat treatment can be performed at a substrate temperature of 50° C. to 200° C., preferably 60° C. to 150° C., more preferably 70° C. to 130° C. The heating atmosphere may be an air atmosphere or an inert gas atmosphere. The heating atmosphere may be an atmospheric pressure atmosphere or a reduced pressure atmosphere. This can improve the adhesion between the insulating layer 127 and the inorganic insulating layer 125 and also improve the corrosion resistance of the insulating layer 127.

[0447] In the first etching process, the sacrificial layers 158R, 158G, and 158B are not completely removed, and the sacrificial layers 158R, 158G, and 158B are left in a state where the film thickness is reduced, so that the first layers 135R, 135G, and 135B can be prevented from being damaged and deteriorated in the heat treatment, and therefore the reliability of the light-emitting device can be improved.

[0448] 8(A), an etching process is performed using the insulating layer 127 as a mask to remove parts of the sacrificial layers 158R, 158G, and 158B. As a result, openings are formed in the sacrificial layers 158R, 158G, and 158B, respectively, and the top surfaces of the first layer 135R, 135G, 135B, and the conductive layer 152C are exposed. Note that, hereinafter, this etching process may be referred to as a second etching process.

[0449] An end portion of the inorganic insulating layer 125 is covered with an insulating layer 127. Also, Fig. 8(A) shows an example in which a part of the end portion of the sacrificial layer 158G (specifically, the tapered portion formed by the first etching process) is covered with the insulating layer 127, and the tapered portion formed by the second etching process is exposed.

[0450] The second etching process is performed by wet etching. By using the wet etching method, damage to the first layer 135R, the first layer 135G, and the first layer 135B can be reduced compared to the case of using the dry etching method. The wet etching can be performed using, for example, an alkaline solution or an acidic solution. It is preferable to use an aqueous solution so that the first layer 135 does not dissolve.

[0451] 8B, the second electrode 102 is formed on the first layer 135R, the first layer 135G, the first layer 135B, the conductive layer 152C, and the insulating layer 127. The second electrode 102 can be formed by a method such as a sputtering method or a vacuum deposition method. At this time, as shown in FIG. 2, the first layer 135 may be formed as a laminated structure of the first layer 135 and the common layer 136, and the second electrode 102 may be formed thereon.

[0452] 8C, a protective layer 131 is formed on the second electrode 102. The protective layer 131 can be formed by a method such as a vacuum deposition method, a sputtering method, a CVD method, or an ALD method.

[0453] Then, the substrate 120 is attached over the protective layer 131 using the resin layer 122, so that a display device can be manufactured. As described above, in a manufacturing method of a display device according to one embodiment of the present invention, the insulating layer 156 is provided so as to have a region overlapping with a side surface of the conductive layer 151, and the conductive layer 152 is formed so as to cover the conductive layer 151 and the insulating layer 156. This can increase the yield of the display device and suppress the occurrence of defects.

[0454] As described above, in the manufacturing method of the display device according to one embodiment of the present invention, the island-shaped first layer 135R, the island-shaped first layer 135G, and the first layer 135B are formed by forming a film on one surface and then processing it, instead of using a fine metal mask, so that the island-shaped layers can be formed with a uniform thickness. As a result, a high-definition display device or a display device with a high aperture ratio can be realized. Even if the definition or aperture ratio is high and the distance between the subpixels is extremely short, the first layer 135R, the first layer 135G, and the first layer 135B can be prevented from contacting each other in adjacent subpixels. Therefore, leakage current can be prevented from occurring between the subpixels. As a result, crosstalk can be prevented, and a display device with extremely high contrast can be realized. Even in a display device including a tandem light-emitting device manufactured by a photolithography method, a display device with good characteristics can be provided.

[0455] (Embodiment 4) In this embodiment, a display device according to one embodiment of the present invention will be described.

[0456] The display device of the present embodiment can be a high-definition display device. Therefore, the display device of the present embodiment can be used for, for example, a display unit of a wristwatch-type or bracelet-type information terminal (wearable device), a VR device such as a head-mounted display (HMD), and a head-mounted wearable device such as a glasses-type AR device.

[0457] The display device of the present embodiment can be a high-resolution display device or a large-sized display device. Therefore, the display device of the present embodiment can be used in electronic devices having relatively large screens, such as television devices, desktop or notebook personal computers, computer monitors, digital signage, and large game machines such as pachinko machines, as well as in the display units of digital cameras, digital video cameras, digital photo frames, mobile phones, portable game machines, personal digital assistants, and sound reproducing devices.

[0458] [Display module] 9A shows a perspective view of a display module 280. The display module 280 includes a display device 100A and an FPC 290. Note that the display device included in the display module 280 is not limited to the display device 100A and may be any of display devices 100B to 100E described later.

[0459] The display module 280 has a substrate 291 and a substrate 292. The display module 280 has a display unit 281. The display unit 281 is a region that displays an image in the display module 280, and is a region where light from each pixel provided in a pixel unit 284 described later can be viewed.

[0460] 9(B) shows a perspective view that typically illustrates the configuration on the substrate 291 side. A circuit portion 282, a pixel circuit portion 283 on the circuit portion 282, and a pixel portion 284 on the pixel circuit portion 283 are stacked on the substrate 291. A terminal portion 285 for connecting to an FPC 290 is provided in a portion of the substrate 291 that does not overlap with the pixel portion 284. The terminal portion 285 and the circuit portion 282 are electrically connected to each other by a wiring portion 286 that is composed of a plurality of wirings.

[0461] The pixel section 284 has a plurality of pixels 284a arranged periodically. An enlarged view of one pixel 284a is shown on the right side of Fig. 9(B). The various configurations described in the previous embodiment can be applied to the pixel 284a. Fig. 9(B) shows an example in which the pixel 284a has the same configuration as the pixel 178 shown in Fig. 2.

[0462] The pixel circuit section 283 has a plurality of pixel circuits 283a that are periodically arranged.

[0463] One pixel circuit 283a is a circuit that controls the driving of a plurality of devices included in one pixel 284a.

[0464] The circuit portion 282 includes a circuit for driving each pixel circuit 283a of the pixel circuit portion 283. For example, it is preferable that the circuit portion 282 includes one or both of a gate line driver circuit and a source line driver circuit. In addition, the circuit portion 282 may include at least one of an arithmetic circuit, a memory circuit, a power supply circuit, and the like.

[0465] The FPC 290 functions as wiring for supplying a video signal, a power supply potential, or the like from the outside to the circuit portion 282. In addition, an IC may be mounted on the FPC 290.

[0466] Since the display module 280 can be configured such that one or both of the pixel circuit portion 283 and the circuit portion 282 are stacked below the pixel portion 284, the aperture ratio (effective display area ratio) of the display portion 281 can be made extremely high.

[0467] Such a display module 280 has extremely high resolution and can be suitably used in VR devices such as HMDs or glasses-type AR devices. For example, even in a configuration in which the display unit of the display module 280 is viewed through a lens, the display module 280 has an extremely high resolution display unit 281, so that pixels are not visible even when the display unit is enlarged with a lens, and a highly immersive display can be performed. In addition, the display module 280 is not limited to this and can be suitably used in electronic devices having a relatively small display unit.

[0468] [Display device 100A] A display device 100A shown in FIG. 10A includes a substrate 301, a light emitting device 130R, a light emitting device 130G, a light emitting device 130B, a capacitor 240, and a transistor 310.

[0469] The substrate 301 corresponds to the substrate 291 in FIGS. 9A and 9B. The transistor 310 is a transistor having a channel formation region in the substrate 301. As the substrate 301, for example, a semiconductor substrate such as a single crystal silicon substrate can be used. The transistor 310 includes a part of the substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 functions as a gate electrode. The insulating layer 313 is located between the substrate 301 and the conductive layer 311 and functions as a gate insulating layer. The low-resistance region 312 is a region in which the substrate 301 is doped with impurities, and functions as a source or drain. The insulating layer 314 is provided to cover a side surface of the conductive layer 311.

[0470] In addition, an element isolation layer 315 is provided between two adjacent transistors 310 so as to be embedded in the substrate 301 .

[0471] In addition, an insulating layer 261 is provided to cover the transistor 310 , and a capacitor 240 is provided on the insulating layer 261 .

[0472] Capacitor 240 has conductive layer 241, conductive layer 245, and insulating layer 243 located therebetween. Conductive layer 241 functions as one electrode of capacitor 240, conductive layer 245 functions as the other electrode of capacitor 240, and insulating layer 243 functions as a dielectric of capacitor 240.

[0473] The conductive layer 241 is provided over the insulating layer 261 and is embedded in the insulating layer 254. The conductive layer 241 is electrically connected to one of the source and the drain of the transistor 310 by a plug 271 embedded in the insulating layer 261. The insulating layer 243 is provided to cover the conductive layer 241. The conductive layer 245 is provided in a region overlapping with the conductive layer 241 with the insulating layer 243 interposed therebetween.

[0474] An insulating layer 255 is provided covering the capacitor 240, an insulating layer 174 is provided on the insulating layer 255, and an insulating layer 175 is provided on the insulating layer 174. Light-emitting device 130R, light-emitting device 130G, and light-emitting device 130B are provided on the insulating layer 175. An insulator is provided in the region between adjacent light-emitting devices.

[0475] An insulating layer 156R is provided so as to have an area overlapping with a side surface of the conductive layer 151R, an insulating layer 156G is provided so as to have an area overlapping with a side surface of the conductive layer 151G, and an insulating layer 156B is provided so as to have an area overlapping with a side surface of the conductive layer 151B. A conductive layer 152R is provided so as to cover the conductive layer 151R and the insulating layer 156R, a conductive layer 152G is provided so as to cover the conductive layer 151G and the insulating layer 156G, and a conductive layer 152B is provided so as to cover the conductive layer 151B and the insulating layer 156B. A sacrificial layer 158R is located on the first layer 135R, a sacrificial layer 158G is located on the first layer 135G, and a sacrificial layer 158B is located on the first layer 135B.

[0476] The conductive layer 151R, the conductive layer 151G, and the conductive layer 151B are electrically connected to one of the source or the drain of the transistor 310 via an insulating layer 243, an insulating layer 255, an insulating layer 174, a plug 256 embedded in the insulating layer 175, a conductive layer 241 embedded in the insulating layer 254, and a plug 271 embedded in the insulating layer 261. Various conductive materials can be used for the plug.

[0477] Further, a protective layer 131 is provided on the light emitting devices 130R, 130G, and 130B. The substrate 120 is bonded onto the protective layer 131 by a resin layer 122. For details of the components from the light emitting devices 130 to the substrate 120, refer to the third embodiment. The substrate 120 corresponds to the substrate 292 in FIG. 9(A).

[0478] Fig. 10(B) is a modified example of the display device 100A shown in Fig. 10(A). The display device shown in Fig. 10(B) has a colored layer 132R, a colored layer 132G, and a colored layer 132B, and the light-emitting device 130 has an area overlapping one of the colored layer 132R, the colored layer 132G, and the colored layer 132B. In the display device shown in Fig. 10(B), the light-emitting device 130 can emit, for example, white light. Also, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light.

[0479] [Display device 100B] FIG. 11 shows a perspective view of the display device 100B, and FIG. 12 shows a cross-sectional view of the display device 100C.

[0480] The display device 100B has a configuration in which a substrate 352 and a substrate 351 are bonded together. In Fig. 11, the substrate 352 is indicated by a dashed line.

[0481] The display device 100B has a pixel unit 177, a connection unit 140, a circuit 356, wiring 355, etc. Fig. 11 shows an example in which an IC 354 and an FPC 353 are mounted on the display device 100B. Therefore, the configuration shown in Fig. 11 can also be called a display module having the display device 100B, an IC (integrated circuit), and an FPC. Here, a display device having a connector such as an FPC attached to a substrate, or a display device having an IC mounted on the substrate, is called a display module.

[0482] The connection section 140 is provided outside the pixel section 177. There may be one or more connection sections 140. The connection section 140 electrically connects the common electrode of the light emitting device and the conductive layer, and can supply a potential to the common electrode.

[0483] The circuit 356 can be, for example, a scanning line driver circuit.

[0484] The wiring 355 has a function of supplying signals and power to the pixel portion 177 and the circuit 356. The signals and power are input to the wiring 355 from the outside via the FPC 353 or from the IC 354.

[0485] 11 shows an example in which an IC 354 is provided on a substrate 351 by a chip on glass (COG) method or a chip on film (COF) method. For example, an IC having a scanning line driver circuit or a signal line driver circuit can be used as the IC 354. Note that the display device 100B and the display module may not include an IC. Also, the IC may be mounted on an FPC by a COF method, for example.

[0486] FIG. 12 shows an example of a cross section of the display device 100C, in which a portion of the region including the FPC 353, a portion of the circuit 356, a portion of the pixel portion 177, a portion of the connection portion 140, and a portion of the region including the end portion are cut away.

[0487] [Display device 100C] The display device 100C shown in FIG. 12 has, between a substrate 351 and a substrate 352, a transistor 201, a transistor 205, a light-emitting device 130R that emits red light, a light-emitting device 130G that emits green light, and a light-emitting device 130B that emits blue light, etc.

[0488] For details of the light emitting devices 130R, 130G, and 130B, refer to the first embodiment.

[0489] Light-emitting device 130R has conductive layer 224R, conductive layer 151R on conductive layer 224R, and conductive layer 152R on conductive layer 151R. Light-emitting device 130G has conductive layer 224G, conductive layer 151G on conductive layer 224G, and conductive layer 152G on conductive layer 151G. Light-emitting device 130B has conductive layer 224B, conductive layer 151B on conductive layer 224B, and conductive layer 152B on conductive layer 151B.

[0490] The conductive layer 224R is connected to the conductive layer 222b of the transistor 205 through an opening provided in the insulating layer 214. An end of the conductive layer 151R is located outside an end of the conductive layer 224R. An insulating layer 156R is provided to have a region in contact with a side surface of the conductive layer 151R, and a conductive layer 152R is provided to cover the conductive layer 151R and the insulating layer 156R.

[0491] Conductive layer 224G, conductive layer 151G, conductive layer 152G, and insulating layer 156G in light-emitting device 130G, and conductive layer 224B, conductive layer 151B, conductive layer 152B, and insulating layer 156B in light-emitting device 130B are similar to conductive layer 224R, conductive layer 151R, conductive layer 152R, and insulating layer 156R in light-emitting device 130R, and therefore detailed description thereof will be omitted.

[0492] Recesses are formed in the conductive layers 224R, 224G, and 224B so as to cover the openings provided in the insulating layer 214. The layer 128 is embedded in the recesses.

[0493] The layer 128 has a function of planarizing the recesses of the conductive layer 224R, the conductive layer 224G, and the conductive layer 224B. The conductive layer 151R, the conductive layer 151G, and the conductive layer 151B, which are electrically connected to the conductive layer 224R, the conductive layer 224G, and the conductive layer 224B, are provided on the conductive layer 224R, the conductive layer 224G, and the conductive layer 224B, and the layer 128. Therefore, the regions overlapping with the recesses of the conductive layer 224R, the conductive layer 224G, and the conductive layer 224B can also be used as light-emitting regions, and the aperture ratio of the pixel can be increased.

[0494] The layer 128 may be an insulating layer or a conductive layer. Various inorganic insulating materials, organic insulating materials, and conductive materials can be appropriately used for the layer 128. In particular, the layer 128 is preferably formed using an insulating material, and more preferably formed using an organic insulating material. For example, the organic insulating material that can be used for the insulating layer 127 described above can be used for the layer 128.

[0495] A protective layer 131 is provided on the light emitting device 130R, the light emitting device 130G, and the light emitting device 130B. The protective layer 131 and the substrate 352 are bonded via an adhesive layer 142. The substrate 352 is provided with a light shielding layer 157. A solid sealing structure, a hollow sealing structure, or the like can be applied to seal the light emitting device 130. In FIG. 12, the space between the substrate 352 and the substrate 351 is filled with the adhesive layer 142, and a solid sealing structure is applied. Alternatively, the space may be filled with an inert gas (nitrogen, argon, or the like), and a hollow sealing structure may be applied. In this case, the adhesive layer 142 may be provided so as not to overlap with the light emitting device. The space may also be filled with a resin different from the adhesive layer 142 provided in a frame shape.

[0496] 12 shows an example in which the connection portion 140 has a conductive layer 224C obtained by processing the same conductive film as the conductive layers 224R, 224G, and 224B, a conductive layer 151C obtained by processing the same conductive film as the conductive layers 151R, 151G, and 151B, and a conductive layer 152C obtained by processing the same conductive film as the conductive layers 152R, 152G, and 152B. Also, FIG. 12 shows an example in which an insulating layer 156C is provided so as to have an area overlapping with the side surface of the conductive layer 151C.

[0497] The display device 100C is a top emission type. Light emitted by the light emitting device is emitted to the substrate 352 side. The substrate 352 is preferably made of a material having high transparency to visible light. When the light emitting device emits infrared or near infrared light, it is preferably made of a material having high transparency to the infrared light. The first electrode (pixel electrode) contains a material that reflects visible light, and the second electrode 155 (counter electrode) contains a material that transmits visible light.

[0498] An insulating layer 211, an insulating layer 213, an insulating layer 215, and an insulating layer 214 are provided over a substrate 351 in this order. A part of the insulating layer 211 functions as a gate insulating layer for each transistor. A part of the insulating layer 213 functions as a gate insulating layer for each transistor. The insulating layer 215 is provided to cover the transistors. The insulating layer 214 is provided to cover the transistors and functions as a planarizing layer. Note that the number of gate insulating layers and the number of insulating layers covering the transistors are not limited, and each may be a single layer or two or more layers.

[0499] Each of the insulating layers 211, 213, and 215 is preferably an inorganic insulating film.

[0500] The insulating layer 214, which functions as a planarizing layer, is preferably an organic insulating layer.

[0501] The transistor 201 and the transistor 205 each have a conductive layer 221 functioning as a gate, an insulating layer 211 functioning as a gate insulating layer, a conductive layer 222a and a conductive layer 222b functioning as a source and a drain, a semiconductor layer 231, an insulating layer 213 functioning as a gate insulating layer, and a conductive layer 223 functioning as a gate.

[0502] A connection portion 204 is provided in an area of ​​the substrate 351 where the substrate 352 does not overlap. In the connection portion 204, the wiring 355 is electrically connected to the FPC 353 via the conductive layer 166 and the connection layer 242. The conductive layer 166 is an example of a laminated structure of a conductive film obtained by processing the same conductive film as the conductive layers 224R, 224G, and 224B, a conductive film obtained by processing the same conductive film as the conductive layers 151R, 151G, and 151B, and a conductive film obtained by processing the same conductive film as the conductive layers 152R, 152G, and 152B. On the upper surface of the connection portion 204, the conductive layer 166 is exposed. This allows the connection portion 204 and the FPC 353 to be electrically connected via the connection layer 242.

[0503] It is preferable to provide a light-shielding layer 157 on the surface of the substrate 352 facing the substrate 351. The light-shielding layer 157 can be provided between adjacent light-emitting devices, on the connection portion 140, on the circuit 356, etc. In addition, various optical members can be disposed on the outside of the substrate 352.

[0504] The materials usable for the substrate 120 can be used for the substrate 351 and the substrate 352, respectively.

[0505] The adhesive layer 142 may be made of a material that can be used for the resin layer 122 .

[0506] The connection layer 242 may be an anisotropic conductive film (ACF), an anisotropic conductive paste (ACP), or the like.

[0507] [Display device 100D] A display device 100D shown in FIG. 13 differs from the display device 100C shown in FIG. 12 mainly in that the display device 100D is a bottom-emission type display device.

[0508] Light emitted by the light emitting device is emitted to the side of the substrate 351. It is preferable that a material having high transparency to visible light is used for the substrate 351. On the other hand, the light transmissivity of a material used for the substrate 352 does not matter.

[0509] It is preferable to form a light-shielding layer 157 between the substrate 351 and the transistor 201 and between the substrate 351 and the transistor 205. Fig. 13 shows an example in which the light-shielding layer 157 is provided over the substrate 351, the insulating layer 153 is provided over the light-shielding layer 157, and the transistors 201, 205, etc. are provided over the insulating layer 153.

[0510] Light emitting device 130R includes a conductive layer 112R, a conductive layer 126R on conductive layer 112R, and a conductive layer 129R on conductive layer 126R.

[0511] Light emitting device 130B has conductive layer 112B, conductive layer 126B on conductive layer 112B, and conductive layer 129B on conductive layer 126B.

[0512] A material having high transparency to visible light is used for the conductive layers 112R, 112B, 126R, 126B, 129R, and 129B. A material that reflects visible light is preferably used for the second electrode.

[0513] Although the light emitting device 130G is not shown in FIG. 13, the light emitting device 130G is also provided.

[0514] In addition, although FIG. 13 and other figures show an example in which the upper surface of layer 128 has a flat portion, the shape of layer 128 is not particularly limited.

[0515] [Display device 100E] The display device 100E shown in FIG. 14 is a modification of the display device 100C shown in FIG. 12, and differs from the display device 100C mainly in that the display device 100E has colored layers 132R, 132G, and 132B.

[0516] In the display device 100E, the light emitting device 130 has an area overlapping one of the colored layer 132R, the colored layer 132G, and the colored layer 132B. The colored layer 132R, the colored layer 132G, and the colored layer 132B can be provided on the surface of the substrate 352 facing the substrate 351. An end of the colored layer 132R, an end of the colored layer 132G, and an end of the colored layer 132B can overlap the light blocking layer 157.

[0517] In the display device 100E, the light emitting device 130 can emit, for example, white light. For example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light. The display device 100E may be configured such that the colored layers 132R, 132G, and 132B are provided between the protective layer 131 and the adhesive layer 142.

[0518] Although an example in which the upper surface of the layer 128 has a flat portion is shown in FIG. 12 and FIG. 14 and the like, the shape of the layer 128 is not particularly limited.

[0519] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in the case where a plurality of configuration examples are shown in one embodiment mode in this specification, the configuration examples can be combined as appropriate.

[0520] (Embodiment 5) In this embodiment, an electronic device according to one embodiment of the present invention will be described.

[0521] The electronic devices of this embodiment include the display device of one embodiment of the present invention in a display portion. The display device of one embodiment of the present invention has high display performance and can easily achieve high definition and high resolution. Therefore, the display device of one embodiment of the present invention can be used in the display portion of various electronic devices.

[0522] Examples of electronic devices include electronic devices with relatively large screens, such as television devices, desktop or notebook personal computers, computer monitors, digital signage, large game machines such as pachinko machines, as well as digital cameras, digital video cameras, digital photo frames, mobile phones, portable game machines, personal digital assistants, and audio playback devices.

[0523] In particular, the display device of one embodiment of the present invention can be suitably used in electronic devices having a relatively small display area because it can increase the resolution. Examples of such electronic devices include wristwatch-type and bracelet-type information terminals (wearable devices), and head-mounted wearable devices such as VR devices, glasses-type AR devices, and MR devices.

[0524] The electronic device of this embodiment may have a sensor (including a function of measuring force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays).

[0525] An example of a wearable device that can be attached to the head will be described with reference to FIGS. 15(A) to 15(D).

[0526] Electronic device 700A shown in FIG. 15(A) and electronic device 700B shown in FIG. 15(B) each have a pair of display panels 751, a pair of housings 721, a communication unit (not shown), a pair of mounting units 723, a control unit (not shown), an imaging unit (not shown), a pair of optical members 753, a frame 757, and a pair of nose pads 758.

[0527] The display device of one embodiment of the present invention can be applied to the display panel 751. Thus, the electronic device can be highly reliable.

[0528] Each of the electronic device 700A and the electronic device 700B can project an image displayed on the display panel 751 onto a display area 756 of the optical member 753. Since the optical member 753 has translucency, a user can see the image displayed in the display area superimposed on a transmitted image visually recognized through the optical member 753.

[0529] The electronic device 700A and the electronic device 700B may be provided with a camera capable of capturing an image of the front as an imaging unit. In addition, the electronic device 700A and the electronic device 700B may each be provided with an acceleration sensor such as a gyro sensor, thereby detecting the orientation of the user's head and displaying an image corresponding to the orientation in the display area 756.

[0530] The communication unit has a wireless communication device and can supply, for example, a video signal through the wireless communication device. Note that instead of or in addition to the wireless communication device, a connector to which a cable through which a video signal and a power supply potential can be connected may be provided.

[0531] Furthermore, the electronic device 700A and the electronic device 700B are provided with a battery, which can be charged wirelessly and / or wired.

[0532] The housing 721 may be provided with a touch sensor module.

[0533] As the touch sensor module, various touch sensors can be applied. For example, various types of sensors can be adopted, such as a capacitance type, a resistive film type, an infrared type, an electromagnetic induction type, a surface acoustic wave type, or an optical type. In particular, it is preferable to apply a capacitance type or an optical type sensor to the touch sensor module.

[0534] Electronic device 800A shown in Figure 15 (C) and electronic device 800B shown in Figure 15 (D) each have a pair of display units 820, a housing 821, a communication unit 822, a pair of mounting units 823, a control unit 824, a pair of imaging units 825, and a pair of lenses 832.

[0535] The display device of one embodiment of the present invention can be applied to the display portion 820. Thus, the electronic device can be made highly reliable.

[0536] Display unit 820 is provided inside housing 821 at a position that can be viewed through lens 832. Also, by displaying different images on the pair of display units 820, it is possible to perform three-dimensional display using parallax.

[0537] It is preferable that electronic device 800A and electronic device 800B each have a mechanism capable of adjusting the left-right positions of lens 832 and display unit 820 so that they are optimally positioned according to the position of the user's eyes.

[0538] The mounting portion 823 allows the user to mount the electronic device 800A or the electronic device 800B on the head.

[0539] The imaging unit 825 has a function of acquiring external information. Data acquired by the imaging unit 825 can be output to the display unit 820. An image sensor can be used for the imaging unit 825. In addition, multiple cameras may be provided so as to be compatible with multiple angles of view, such as telephoto and wide angle.

[0540] The electronic device 800A may have a vibration mechanism that functions as a bone conduction earphone.

[0541] The electronic device 800A and the electronic device 800B may each have an input terminal. The input terminal can be connected to a cable for supplying a video signal from a video output device or the like and power for charging a battery provided in the electronic device.

[0542] The electronic device of one embodiment of the present invention may have a function of wireless communication with the earphone 750.

[0543] 15B includes an earphone unit 727. A part of a wiring connecting the earphone unit 727 and a control unit may be disposed inside the housing 721 or the attachment unit 723.

[0544] 15D includes an earphone unit 827. For example, the earphone unit 827 and the control unit 824 may be configured to be connected to each other by wire.

[0545] As described above, as electronic devices according to one embodiment of the present invention, both glasses-type devices (such as the electronic device 700A and the electronic device 700B) and goggles-type devices (such as the electronic device 800A and the electronic device 800B) are suitable.

[0546] An electronic device 6500 shown in FIG. 16A is a portable information terminal that can be used as a smartphone.

[0547] The electronic device 6500 includes a housing 6501, a display portion 6502, a power button 6503, a button 6504, a speaker 6505, a microphone 6506, a camera 6507, and a light source 6508. The display portion 6502 has a touch panel function.

[0548] The display device of one embodiment of the present invention can be applied to the display portion 6502. Therefore, the electronic device can be highly reliable.

[0549] FIG. 16B is a schematic cross-sectional view including the end of the housing 6501 on the microphone 6506 side.

[0550] A light-transmitting protective member 6510 is provided on the display surface side of the housing 6501, and a display panel 6511, optical members 6512, a touch sensor panel 6513, a printed circuit board 6517, a battery 6518, etc. are arranged in the space surrounded by the housing 6501 and the protective member 6510.

[0551] A display panel 6511, an optical member 6512, and a touch sensor panel 6513 are fixed to the protective member 6510 by an adhesive layer (not shown).

[0552] In an area outside the display unit 6502, a part of the display panel 6511 is folded back, and the folded back part is connected to an FPC 6515. An IC 6516 is mounted on the FPC 6515. The FPC 6515 is connected to a terminal provided on a printed circuit board 6517.

[0553] The display device of one embodiment of the present invention can be applied to the display panel 6511. Therefore, an extremely lightweight electronic device can be realized. In addition, since the display panel 6511 is extremely thin, a large-capacity battery 6518 can be mounted thereon while keeping the thickness of the electronic device small. In addition, by folding back a part of the display panel 6511 and arranging a connection portion with the FPC 6515 on the back side of the pixel portion, an electronic device with a narrow frame can be realized.

[0554] 16C shows an example of a television set. In a television set 7100, a display portion 7000 is incorporated in a housing 7171. Here, the housing 7171 is supported by a stand 7173.

[0555] The display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can be provided with high reliability.

[0556] A television set 7100 shown in FIG. 16C can be operated using an operation switch provided in a housing 7171 and a remote control unit 7151 provided separately.

[0557] 16D shows an example of a laptop personal computer 7200. The laptop personal computer 7200 includes a housing 7211, a keyboard 7212, a pointing device 7213, and an external connection port 7214. A display portion 7000 is incorporated in the housing 7211.

[0558] The display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can be provided with high reliability.

[0559] 16(E) and 16(F) show an example of digital signage.

[0560] 16E includes a housing 7301, a display portion 7000, and a speaker 7303. The digital signage 7300 may further include an LED lamp, an operation key (including a power switch or an operation switch), a connection terminal, various sensors, a microphone, and the like.

[0561] 16(F) shows a digital signage 7400 attached to a cylindrical pillar 7401. The digital signage 7400 has a display unit 7000 provided along the curved surface of the pillar 7401.

[0562] 16E and 16F, the display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can have high reliability.

[0563] The larger the display unit 7000, the more information can be provided at one time. Also, the larger the display unit 7000, the more easily it catches people's attention, which can increase the advertising effect of, for example, advertisements.

[0564] Furthermore, as shown in FIGS. 16E and 16F, it is preferable that the digital signage 7300 or the digital signage 7400 be capable of linking with an information terminal 7311 or an information terminal 7411 such as a smartphone carried by a user via wireless communication.

[0565] The electronic devices shown in Figures 17(A) to 17(G) have a housing 9000, a display unit 9001, a speaker 9003, operation keys 9005 (including a power switch or an operation switch), a connection terminal 9006, a sensor 9007 (including a function of measuring force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared rays), a microphone 9008, etc.

[0566] 17(A) to 17(G) have various functions, such as a function of displaying various information (still images, videos, text images, etc.) on a display unit, a touch panel function, a function of displaying a calendar, date, time, etc., a function of controlling processing by various software (programs), a wireless communication function, a function of reading and processing a program or data recorded in a recording medium, etc.

[0567] The electronic devices shown in FIGS. 17A to 17G will be described in detail below.

[0568] FIG. 17A is a perspective view showing a mobile information terminal 9171. The mobile information terminal 9171 can be used as, for example, a smartphone. Note that the mobile information terminal 9171 may be provided with a speaker 9003, a connection terminal 9006, a sensor 9007, or the like. The mobile information terminal 9171 can display text and image information on a plurality of surfaces thereof. FIG. 17A shows an example in which three icons 9050 are displayed. Information 9051 shown in a dashed rectangle can also be displayed on another surface of the display unit 9001. Examples of the information 9051 include notification of incoming e-mail, SNS, phone call, etc., the title of e-mail or SNS, the sender's name, date and time, time, remaining battery level, radio wave intensity, and the like. Alternatively, the icon 9050, etc. may be displayed at the position where the information 9051 is displayed.

[0569] 17B is a perspective view of a mobile information terminal 9172. The mobile information terminal 9172 has a function of displaying information on three or more surfaces of a display unit 9001. Here, an example is shown in which information 9052, information 9053, and information 9054 are displayed on different surfaces. For example, a user can check information 9053 displayed in a position that can be observed from above the mobile information terminal 9172 while the mobile information terminal 9172 is stored in a breast pocket of clothes.

[0570] 17C is a perspective view showing a tablet terminal 9173. The tablet terminal 9173 is capable of executing various applications such as mobile phone, e-mail, text browsing and creation, music playback, Internet communication, computer games, etc. The tablet terminal 9173 has a display unit 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front side of a housing 9000, operation keys 9005 as operation buttons on the left side of the housing 9000, and a connection terminal 9006 on the bottom.

[0571] 17D is a perspective view showing a wristwatch-type mobile information terminal 9200. The mobile information terminal 9200 can be used as, for example, a smart watch (registered trademark). The display surface of the display unit 9001 is curved, and display can be performed along the curved display surface. The mobile information terminal 9200 can also perform hands-free conversation by communicating with, for example, a headset capable of wireless communication. The mobile information terminal 9200 can also perform data transmission and charging with another information terminal through a connection terminal 9006. Note that charging may be performed by wireless power supply.

[0572] 17(E) to 17(G) are perspective views showing a foldable mobile information terminal 9201. FIG. 17(E) is a perspective view of the mobile information terminal 9201 in an unfolded state, FIG. 17(G) is a perspective view of the mobile information terminal 9201 in a folded state, and FIG. 17(F) is a perspective view of a state in the middle of changing from one of FIG. 17(E) and FIG. 17(G) to the other. The mobile information terminal 9201 has excellent portability in a folded state, and has excellent viewability of the display due to a seamless wide display area in an unfolded state. A display portion 9001 of the mobile information terminal 9201 is supported by three housings 9000 connected by a hinge 9055. For example, the display portion 9001 can be bent with a curvature radius of 0.1 mm to 150 mm.

[0573] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in the case where a plurality of configuration examples are shown in one embodiment mode in this specification, the configuration examples can be combined as appropriate. EXAMPLES

[0574] Synthesis Example 1 In this synthesis example, a method for synthesizing N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-2-amine (abbreviation: Fr(2)F(4)A(βN2)B), shown as structural formula (162) in the embodiment, is described. The structural formula of Fr(2)F(4)A(βN2)B is shown below.

[0575] [ka]

[0576] <Step 1: Synthesis of N-(chlorophenyl-4-yl)dibenzofuran-2-amine> 4.2g (4.0mmol) of 4-chloroaniline and 10g (40mmol) of 2-bromodibenzofuran were added to a 500mL three-neck flask. After replacing the atmosphere in the flask with nitrogen, 7.8g (81mmol) of sodium tert-butoxide and 202mL of toluene were added. This mixture was degassed by stirring under reduced pressure. 2.4mL (0.81mmol) of tris(tert-butyl)phosphine (hexane solution 10wt%) was added to this mixture, which was then heated to 60℃ and stirred. After stirring, 0.23g (0.40mmol) of bis(dibenzylideneacetone)palladium(0) was added, heated to 120℃, and stirred for 1 hour. After stirring, the reaction solution was subjected to suction filtration through alumina, Celite (Fujifilm Wako Pure Chemical Industries, Ltd., catalog number: 537-02305), and Florisil (Fujifilm Wako Pure Chemical Industries, Ltd., catalog number: 066-05265). The filtrate was concentrated to obtain a solid, which was purified by silica gel column chromatography (hexane:toluene = 9:1) to obtain 5.4 g of a light yellow solid containing the target product. Hexane was added to an ethyl acetate solution of the obtained solid, and the precipitated solid was collected by suction filtration to obtain 5.2 g of the target white solid in a yield of 44%. The synthesis scheme (s1-1) of step 1 is shown below. In addition, 1 The results of H NMR measurement are shown in Figures 29(A) and (B). Note that Figure 29(B) is an enlarged chart showing the range from 5.5 ppm to 7.8 ppm in Figure 29(A). This shows that N-(chlorophenyl-4-yl)dibenzofuran-2-amine was obtained.

[0577] [ka]

[0578] <Step 2: Synthesis of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-2-amine> 5.0g (17mmol) of N-(chlorophenyl-4-yl)dibenzofuran-2-amine synthesized in step 1 and 4.7g (17mmol) of 4-bromo-9,9'-dimethylfluorene were added to a 300mL three-neck flask. After replacing the atmosphere in the flask with nitrogen, 3.3g (34mmol) of sodium tert-butoxide and 85mL of toluene were added. This mixture was degassed by stirring under reduced pressure. 1.0mL (0.34mmol) of tris(tert-butyl)phosphine (10wt% hexane solution) was added to this mixture, and the mixture was heated to 60℃ and stirred. After stirring, 98mg (0.17mmol) of bis(dibenzylideneacetone)palladium(0) was added, heated to 120℃, and stirred for 1 hour. After stirring, the reaction solution was suction filtered through alumina, Celite (FUJIFILM Wako Pure Chemical Industries, Ltd., catalog number: 537-02305), and Florisil (FUJIFILM Wako Pure Chemical Industries, Ltd., catalog number: 066-05265). The filtrate was concentrated to obtain a solid, which was purified by silica gel column chromatography (hexane) to obtain 4.5 g of the desired white solid in a yield of 65%. The synthesis scheme (s1-2) of step 2 is shown below. 1 The results of H NMR measurement are shown in Figures 30(A) and (B). Note that Figure 30(B) is an enlarged chart showing the range from 6.7 ppm to 7.9 ppm in Figure 30(A). This shows that N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-2-amine was obtained.

[0579] [ka]

[0580] <Step 3: Synthesis of Fr(2)F(4)A(βN2)B> In a 200mL three-neck flask, 4.5g (9.2mmol) of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-2-amine, 3.5g (9.2mmol) of 2-[2,2'-binaphthalen-6-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 110mg (0.37mmol) of tri(o-tolyl)phosphine, 7.8g (37mmol) of tripotassium phosphate, 73mL of toluene, 18mL of ethanol, and 18mL of pure water were added. The mixture was stirred and degassed under reduced pressure, then heated to 60°C, 41mg of palladium(II) acetate was added, and the mixture was heated to 90°C and stirred for 24 hours. After stirring, the mixture was cooled to 60°C, and 41 mg of palladium (II) acetate, 130 mg of di(1-adamantyl)-n-butylphosphine, and 5.0 g of potassium carbonate were added and stirred at 90°C for one week. After stirring, the mixture was cooled to room temperature and the reaction solution was concentrated, and pure water and toluene were added to perform a liquid separation operation. The organic layer was dehydrated with magnesium sulfate and subjected to suction filtration. The solid obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane: toluene = 9: 1), and 1.8 g of the target pale yellow solid was obtained in a yield of 30%. The synthesis scheme (s1-3) of step 3 is shown below.

[0581] [ka]

[0582] The obtained solid (1.4 g) was purified by train sublimation. The purification was carried out by heating the solid at 310°C for 45 hours under a pressure of 2.3 Pa while flowing argon at 10 mL / min. After the purification, 910 mg of the target solid was obtained with a recovery rate of 65%.

[0583] The obtained solid 1 The results of H NMR measurement are shown in Figures 19(A) and (B) and below. Note that Figure 19(B) is an enlarged chart showing the range from 7.00 ppm to 8.25 ppm in Figure 19(A). This shows that Fr(2)F(4)A(βN2)B was obtained in this synthesis example.

[0584] 1 H NMR (dichloromethane-d2,500MHz,20℃): δ=8.18(d,J=7.5Hz,2H), δ=8.03(s,1H), δ=7.97-7.75(m,11H), δ=7.61(d,J=8.5Hz,2H), δ=7.54-7.34(m,9H) , δ=7.28(t,J=7.5Hz,1H), δ=7.23(t,J=7.5Hz,1H), δ=7.14(d,J=7.5Hz,1H), δ=7.11(d,J=7.5Hz,1H), δ=7.09(d,J=8.5Hz,2H), δ=1.54(s,6H)

[0585] <Measurement of physical properties> Next, the UV-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and PL spectrum (photoluminescence spectrum) of the toluene solution and thin film of Fr(2)F(4)A(βN2)B were measured.

[0586] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-770DS, manufactured by JASCO Corporation). The PL spectrum was measured using a spectrofluorophotometer (FP-8600DS, manufactured by JASCO Corporation).

[0587] The absorption spectrum of the toluene solution was calculated by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution of Fr(2)F(4)A(βN2)B in a quartz cell and measuring it.

[0588] The absorption and PL spectra of the thin film were measured by forming a film of FrFA(βN2)B on a quartz substrate by vacuum deposition and sealing it with a quartz substrate as the opposing substrate. The PL spectrum was measured for the sealed sample, and the absorption spectrum was measured for the sample after removing the sealing and the opposing substrate. The absorption spectrum was obtained by subtracting the absorption spectrum of the quartz substrate from the absorption spectrum of FrFA(βN2)B formed on the quartz substrate.

[0589] The measurement results of the toluene solution are shown in Figure 20(A), and the measurement results of the thin film are shown in Figure 20(B). From the measurement results, the toluene solution of Fr(2)F(4)A(βN2)B showed an absorption spectrum peak (absorption peak) around 360 nm, and the thin film of Fr(2)F(4)A(βN2)B showed an absorption peak around 361 nm, and no absorption band was observed on the longer wavelength side than 430 nm in either the toluene solution or the thin film. From this, it became clear that when Fr(2)F(4)A(βN2)B is used in a light-emitting device, it is thought that there will be no decrease in luminous efficiency due to absorption at the wavelength of light used in the display, and it can be used preferably. In addition, the toluene solution of Fr(2)F(4)A(βN2)B had a peak in the emission spectrum (emission peak) at around 418 nm (excitation wavelength: 359 nm), and the thin film of Fr(2)F(4)A(βN2)B had a peak in the emission spectrum at around 441 nm (excitation wavelength: 369 nm). The HOMO and LUMO levels of Fr(2)F(4)A(βN2)B were calculated based on cyclic voltammetry (CV) measurements. The calculation method is shown below.

[0590] 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 tetra-n-butylammonium perchlorate (abbreviation: n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) as a supporting electrolyte to a concentration of 100 mmol / L in dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) and further dissolving the measurement target to a concentration of 2 mmol / L.

[0591] 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 performed at room temperature (20°C or higher and 25°C or lower). 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 example 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.

[0592] 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.

[0593] As a result, the HOMO level of Fr(2)F(4)A(βN2)B was found to be -5.51 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of Fr(2)F(4)A(βN2)B was found to be -2.45 eV in the measurement of the reduction potential Ec [V]. In addition, when comparing the waveforms after the first and 100th cycle in the repeated measurement of the oxidation-reduction wave, the peak intensity was maintained at 92% in the Ea measurement and 99% in the Ec measurement, confirming that Fr(2)F(4)A(βN2)B has very good resistance to repeated oxidation and reduction.

[0594] Differential scanning calorimetry (DSC) of Fr(2)F(4)A(βN2)B was also performed using a PerkinElmer DSC8500. The differential scanning calorimetry was performed by heating the sample from -10°C to 320°C at a heating rate of 40°C / min, holding the sample at the same temperature for 3 minutes, then cooling the sample to -10°C at a heating rate of 40°C / min, and holding the sample at the same temperature for 3 minutes twice in succession. The results of the second cycle of DSC measurement showed that the glass transition point (Tg) of Fr(2)F(4)A(βN2)B was 133°C, and no crystallization or melting point was observed. This indicates that Fr(2)F(4)A(βN2)B is a material with extremely high heat resistance and can maintain a stable film quality against heat.

[0595] Thermogravimetry-Differential Thermal Analysis (TG-DTA) of Fr(2)F(4)A(βN2)B was also performed. A high-sensitivity differential thermobalance (STA2500Regulus, manufactured by Netsch Japan Co., Ltd.) was used for the measurements. The measurements were performed at atmospheric pressure, with a heating rate of 10°C / min, and under a nitrogen gas flow (flow rate of 200mL / min). In the thermogravimetry-differential thermal analysis, it was found that the temperature at which the weight calculated by thermogravimetry was -5% of the weight at the start of the measurement (decomposition temperature) was 472°C or higher, indicating that the substance has high heat resistance. EXAMPLES

[0596] Synthesis Example 2 In this synthesis example, a method for synthesizing N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrFA(βN2)B), shown as structural formula (152) in the embodiment, is described. The structural formula of FrFA(βN2)B is shown below.

[0597] [ka]

[0598] <Step 1: Synthesis of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine> In a 200mL three-neck flask, 4.8g (13.1mmol) of N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine, 5.0g (13.1mmol) of 2-[(2,2'-binaphthalene)-6-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 160mg of tris(o-tolyl)phosphine, 5.5g of potassium carbonate, 40mL of toluene, 10mL of ethanol, and 10mL of pure water were added. The mixture was degassed by stirring under reduced pressure, and then heated to 60°C and stirred for 10 minutes. After stirring, palladium(II) acetate was added and stirred at 90°C for 1 hour. After stirring, the reaction solution was cooled to room temperature, filtered with suction, and washed with ethanol to obtain 6.0g of a gray-brown solid. The gray-brown solid was dissolved in dichloromethane and naturally filtered to obtain 5.1g of a yellow solid. The yellow solid was dissolved in hot toluene, and the solution was allowed to cool to room temperature and recrystallized to obtain 4.4 g of the target pale yellow solid in a yield of 63%. The synthesis scheme (s2-1) of step 1 is shown below. 1 The results of H NMR measurement are shown in Figures 31(A) and (B). Note that Figure 31(B) is an enlarged chart showing the range from 5.9 ppm to 8.2 ppm in Figure 31(A). This shows that N-[4-(2,2'-binaphthyl-6-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine was obtained.

[0599] [ka]

[0600] <Step 2: Synthesis of FrFA(βN2)B> In a 50mL three-neck flask, 1.0g (1.8mmol) of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine and 500mg (1.8mmol) of 4-bromodibenzofuran were added. After replacing the atmosphere in the flask with nitrogen, 360mg (3.7mmol) of sodium tert-butoxide and 18mL of toluene were added. The mixture was degassed by stirring under reduced pressure. 37μL (37μmol) of tris(tert-butyl)phosphine (10wt% hexane solution) was added dropwise to the mixture, which was then heated to 60℃ and stirred. After that, 11mg (18μmol) of bis(dibenzylideneacetone)palladium(0) was added and stirred at 120℃ for 1 hour. After stirring, the reaction solution was filtered through alumina, Celite (FUJIFILM Wako Pure Chemical Industries, Ltd., catalog number: 537-02305), and Florisil (FUJIFILM Wako Pure Chemical Industries, Ltd., catalog number: 066-05265) by suction. The filtrate was concentrated to obtain a solid, which was purified by silica gel column chromatography (hexane: toluene = 7:1) to obtain 675 mg of the desired white solid in a yield of 52%. The synthesis scheme (s2-2) of step 2 is shown below.

[0601] [ka]

[0602] The obtained solid (0.67 g) was purified by train sublimation. The purification was carried out by heating the solid at 295°C for 20 hours under a pressure of 2.9 Pa while flowing argon at 8.0 mL / min. After the purification, 0.33 g of the target solid was obtained with a recovery rate of 49%.

[0603] The obtained solid 1 The results of H NMR measurement are shown in Figures 21(A) and (B) and below. Note that Figure 21(B) is an enlarged chart showing the range from 7.00 ppm to 8.30 ppm in Figure 21(A). This shows that FrFA(βN2)B was obtained in this synthesis example.

[0604] 1 H NMR (dichloromethane-d2,500MHz, 20℃): δ=8.20(s,2H), δ=8.09(s,1H), δ=8.00-7.87 (m,8H), δ=7.82(dt,J=8.0Hz,2.0Hz,2H), δ=7.67(d,J=8.5Hz,2H), δ=7.64(d, J=7.5Hz,1H), δ=7.62(d,J=8.0Hz,1H), δ=7.53-7.47(m,2H), δ=7.41-7.23(m, 9H), δ=7.19(d,J=8.5Hz,2H), δ=7.11(dd,J=8.0Hz,2.0Hz,1H), δ=1.54(s,6H)

[0605] <Measurement of physical properties> Next, the absorption spectrum and PL spectrum of the toluene solution and thin film of FrFA(βN2)B were measured. The measurements were performed in the same manner as in Example 1.

[0606] The measurement results of the solution are shown in Fig. 22(A), and the measurement results of the thin film are shown in Fig. 22(B). From the measurement results, the toluene solution of FrFA(βN2)B showed an absorption peak near 362 nm, the thin film of FrFA(βN2)B showed an absorption peak near 365 nm, and no absorption band was observed on the longer wavelength side than 440 nm. From this, it became clear that even if FrFA(βN2)B is used in a light-emitting device, it is thought that there will be no decrease in luminous efficiency due to absorption at the wavelength of light used in a display, and it can be used preferably. In addition, the toluene solution of FrFA(βN2)B showed an emission peak near 422 nm (excitation wavelength: 366 nm), and the thin film of FrFA(βN2)B showed an emission peak near 444 nm (excitation wavelength: 365 nm).

[0607] The HOMO level and LUMO level of FrFA(βN2) were calculated based on cyclic voltammetry (CV) measurement. The calculation was performed in the same manner as in Example 1. As a result, in the measurement of the oxidation potential Ea [V] of FrFA(βN2), the HOMO level was found to be -5.47 eV. On the other hand, in the measurement of the reduction potential Ec [V], the LUMO level was found to be -2.47 eV. In addition, when the waveforms after the first cycle and the 100th cycle were compared in the repeated measurement of the oxidation-reduction wave, 96% of the peak intensity was maintained in the Ea measurement, and 98% was maintained in the Ec measurement, confirming that FrFA(βN2) has very good resistance to repeated oxidation and repeated reduction.

[0608] Further, DSC measurement of FrFA(βN2) was performed. The measurement was performed in the same manner as in Example 1. From the results of the DSC measurement in the second cycle, the glass transition point of FrFA(βN2) was 128°C, and no crystallization temperature or melting point was observed. This indicates that FrFA(βN2) is a material with extremely high heat resistance, and can maintain a film quality that is stable against heat.

[0609] In addition, TG-DTA of FrFA(βN2) was performed. The measurement was performed in the same manner as in Example 1. As a result, it was found that the decomposition temperature of FrFA(βN2) was 460°C or higher, indicating that it is a substance with high heat resistance. EXAMPLES

[0610] Example 1 In this example, a light-emitting device according to one embodiment of the present invention will be described in detail. The structural formulae of representative organic compounds used in this example are shown below.

[0611] [ka]

[0612] (Method of manufacturing light-emitting devices) First, indium tin oxide containing silicon oxide (ITSO) was formed to a thickness of 110 nm on a glass substrate by a sputtering method to form a first electrode 101. The electrode area was 2 mm×2 mm.

[0613] 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.

[0614] Then 1×10 -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.

[0615] 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. N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrFA(βN2)B) represented by the above structural formula (i) and an electron acceptor material (OCPD-003) having a molecular weight of 672 and containing fluorine were co-deposited on the first electrode 101 to a thickness of 10 nm in a weight ratio of 1:0.1 (=FrFA(βN2)B:OCPD-003) by a deposition method using resistance heating to form a hole injection layer 111.

[0616] Next, FrFA(βN2)B was evaporated onto the hole injection layer 111 to a thickness of 90 nm to form a first hole transport layer, and then N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form a second hole transport layer, forming the hole transport layer 112. The second hole transport layer also functions as an electron blocking layer.

[0617] Next, on the hole transport layer 112, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) 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 (iv) were co-deposited in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) to a film thickness of 25 nm to form an emitting layer 113.

[0618] Then, on the light-emitting layer 113, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (v) was formed into a film with a thickness of 10 nm to form a first electron-transporting layer, and subsequently, 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P) represented by the above structural formula (vi) was formed into a film with a thickness of 15 nm to form a second electron-transporting layer, thereby forming the electron-transporting layer 114.

[0619] On the electron transport layer 114, a film of lithium fluoride was formed to a thickness of 1 nm to form the electron injection layer 115.

[0620] Finally, aluminum was evaporated to a thickness of 200 nm to form a second electrode 102, completing the production of a light-emitting device according to one embodiment of the present invention.

[0621] The element structures of the above light-emitting devices are summarized in the table below.

[0622] [Table 1]

[0623] The above light-emitting devices were sealed with a glass substrate in a nitrogen-atmosphere glove box to prevent exposure to the atmosphere (a sealant was applied around the elements, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), and then the initial characteristics of these light-emitting devices were measured.

[0624] The luminance-current density characteristics of the light-emitting device are shown in Fig. 23, the current efficiency-luminance characteristics in Fig. 24, the luminance-voltage characteristics in Fig. 25, the current density-voltage characteristics in Fig. 26, the external quantum efficiency-luminance characteristics in Fig. 27, and the electroluminescence spectrum in Fig. 28. The 1000 cd / m 2 Table 2 shows the main characteristics in the vicinity. The luminance, CIE chromaticity, and emission spectrum were measured using a spectroradiometer (SR-UL1R, manufactured by Topcon Corporation) at room temperature. The external quantum efficiency was calculated using the measured luminance and emission spectrum, assuming that the light distribution characteristic is a Lambertian type.

[0625] [Table 2]

[0626] 23 to 28 and Table 2 show that the light-emitting device of one embodiment of the present invention has favorable characteristics. EXAMPLES

[0627] Synthesis Example 3 In this synthesis example, N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9'-dimethyl-9H-fluoren-2-yl)dibenzofuran-2-amine (abbreviation: Fr(2)FA(βN2)B) shown as structural formula (153) in the first embodiment was synthesized. Fr(2)FA(βN2)B was synthesized in the same manner as FrFA(βN2)B synthesized in Example 2. The structural formula, synthesis scheme (s3) and 1The H NMR values ​​are shown in the charts in Figures 32(A) and (B). Note that Figure 32(B) is an enlarged chart showing the range from 7.00 ppm to 8.40 ppm in Figure 32(A). This indicates that Fr(2)FA(βN2)B was obtained.

[0628] [ka]

[0629] [ka]

[0630] 1 H NMR (dichloromethane-d2, 500 MHz, 20℃): δ=8.20(s, 2H), δ=8.08(s,1H), δ=8.01-7.84(m, 9H), δ=7.81(dd, J=8.5 Hz, J=2.0 Hz, 1H), δ=7.67(d, J=8.5 Hz, 2H), δ=7.65-7.61(m, 2H), δ=7.57-7.44(m, 5H), δ=7.39(d, J=7.5 Hz, 1H), δ=7.35(dd, J=10 Hz, J=2.5 Hz, 1H), δ=7.31-7.22(m, 6H), δ=7.10(dd, J=8.0 Hz, J=2.5 Hz, 1H), δ=1.40(s, 6H)

[0631] The results of measuring the physical properties of Fr(2)FA(βN2)B are shown in the table below. The measurements of each physical property were performed in the same manner as described in Example 1. As a result, no absorption band was observed for Fr(2)FA(βN2)B at wavelengths longer than 440 nm, and it is believed that there will be no decrease in the luminous efficiency of light-emitting devices due to absorption in the visible light wavelength region, making it suitable for use. It was also shown to be a substance with high heat resistance.

[0632] [Table 3] EXAMPLES

[0633] Synthesis Example 4 In this synthesis example, N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-4-amine (abbreviation: FrF(4)A(βN2)B) was synthesized, which is shown as structural formula (157) in the first embodiment. The structural formula of FrF(4)A(βN2)B is shown below.

[0634] [ka]

[0635] <Step 1: Synthesis of N-(chlorophenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-4-amine> The synthesis was carried out in the same manner as in step 2 of Example 1. The synthesis scheme (s4-1) of step 1 is shown below. 1 H NMR was measured. The values ​​are shown in the charts of Figures 33(A) and (B) below. Note that Figure 33(B) is a chart showing an enlarged range from 6.60 ppm to 8.00 ppm in Figure 33(A). This shows that N-(chlorophenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-4-amine was obtained in this step.

[0636] [ka]

[0637] 1H NMR (dichloromethane-d2,500MHz, 20℃): δ=7.96(d, J=8.0 Hz, 1H), δ=7.73(d, J=8.0Hz, 1H), δ=7.65(d, J=7.5 Hz, 1H), δ=7.43-7.29(m, 6H), δ=7.20(t, J=7.5 Hz, 2H), δ=7.12(d, J=8.0 Hz, 2H), δ=7.09(d, J=8.5 Hz, 2H), δ=7.00(t, J=7.5 Hz, 1H), δ=6.72(d,J=9.5 Hz,2H), δ=1.51(s,6H)

[0638] <Step 2: Synthesis of FrF(4)A(βN2)B> In a 200 mL three-neck flask, 2.0 g (4.1 mmol) of N-(chlorophenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-4-amine obtained in step 1, 1.6 g (4.1 mmol) of 2-[2,2'-binaphthalen-6-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 1.4 g (12 mmol) of potassium tert-butoxide, 41 mL of toluene, 10 mL of ethanol, and 10 mL of pure water were added. The mixture was stirred and degassed under reduced pressure, heated to 60°C, and then [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (abbreviated as PEPPSI) was added. TM 56 mg of 1,2-dihydro-1,3-tetrahydrofuran (IPr) was added and the mixture was heated to 90°C and stirred for 1 hour. After stirring, the mixture was cooled to room temperature and then concentrated, followed by suction filtration using hot toluene. The filtrate was concentrated to obtain a yellow solid, which was dissolved in toluene and then treated for recrystallization by adding ethanol, yielding 2.1 g of the desired pale yellow solid in 74% yield. The synthesis scheme (s4-2) of step 2 is shown below. 1H NMR was measured. The values ​​are shown in the charts in Figures 34(A) and (B). Note that Figure 34(B) is an enlarged chart showing the range from 6.60 ppm to 8.40 ppm in Figure 34(A). This shows that FrF(4)A(βN2)B was obtained in this step.

[0639] [ka]

[0640] 1 H NMR (dichloromethane-d2, 500MHz, 20℃): δ=8.17(d, J=9.0 Hz, 2H), δ=8.03(s, 1H), δ=7.99-7.86(m, 8H), δ=7.77(d, J=7.5 Hz, 3H), δ=7.59(d, J=8.5Hz, 2H), δ=7.52-7.46(m, 2H), δ=7.44-7.39(m, 4H), δ=7.37-7.32(m, 2H), δ=7.26-7.19(m, 4H), δ=7.02(td, J=7.5 Hz, 1.0 Hz, 1H), δ=6.92(d, J=9 Hz, 2H), δ=1.51(s, 6H)

[0641] The results of measuring the physical properties of FrF(4)A(βN2)B are shown in the table below. The measurements of each physical property were performed in the same manner as described in Example 1. As a result, no absorption band was observed for FrF(4)A(βN2)B at wavelengths longer than 440 nm, and it is believed that there will be no decrease in the luminous efficiency of light-emitting devices due to absorption in the visible light wavelength region, making it suitable for use. It was also shown to be a substance with high heat resistance.

[0642] [Table 4] EXAMPLES

[0643] Synthesis Example 5 In this synthesis example, N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-1-amine (abbreviation: Fr(1)FA(βN2)B) shown as structural formula (154) in the first embodiment was synthesized. Fr(1)FA(βN2)B was synthesized in the same manner as FrFA(βN2)B synthesized in Example 2. The structural formula, synthesis scheme (s5) and 1 The H NMR values ​​are as follows: 1 The H NMR charts are shown in Figures 35(A) and (B). Note that Figure 35(B) is an enlarged chart showing the range from 6.80 ppm to 8.40 ppm in Figure 35(A). This shows that Fr(1)FA(βN2)B was obtained in this synthesis example.

[0644] [ka]

[0645] [ka]

[0646] 1 H NMR (dichloromethane-d2, 500MHz, 20℃): δ=8.19(s, 2H), δ=8.07(d, J=1.5 Hz, 1H), δ=7.99-7.87(m, 7H), δ=7.79(dd, J=8.5 Hz, 2.0Hz, 1H), δ=7.67(dt, J=9.0 Hz, 5.0 Hz, 2H), δ=7.61(d, J=7.5Hz, 1H), δ=7.58(d, J=8.5 Hz, 1H), δ=7.53-7.44(m, 5H), δ=7.37(d, J=7.0 Hz, 1H), δ=7.34-7.21(m, 7H), δ=7.14-7.11(m, 1H), δ=7.05(dd, J=8.0 Hz, 2.0Hz, 1H), δ=7.00(t, J=2.5Hz, 1H), δ=1.35(s, 6H)

[0647] The results of measuring the physical properties of Fr(1)FA(βN2)B are shown in the table below. The measurements of each physical property were performed in the same manner as described in Example 1. As a result, no absorption band was observed for Fr(1)FA(βN2)B at wavelengths longer than 440 nm, and it is believed that there will be no decrease in the luminous efficiency of light-emitting devices due to absorption in the visible light wavelength region, making it suitable for use. It was also shown to be a substance with high heat resistance.

[0648] [Table 5] EXAMPLES

[0649] Synthesis Example 6 In this synthesis example, N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9'-diphenyl-9H-fluoren-2-yl)dibenzofuran-2-amine (abbreviation: Fr(2)FLP(2)A(βN2)B) was synthesized, which is shown as structural formula (123) in the first embodiment. The structural formula of Fr(2)FLP(2)A(βN2)B is shown below.

[0650] [ka]

[0651] <Step 1: Synthesis of N-(chlorophenyl-4-yl)-N-(9,9'-diphenyl-9H-fluoren-2-yl)dibenzofuran-2-amine> The synthesis was carried out in the same manner as in step 2 of Example 1. The synthesis scheme (s6-1) of step 1 is shown below. 1 H NMR was measured, and the values ​​are shown below, and the charts are shown in Figures 36(A) and (B). Note that Figure 36(B) is a chart showing an enlarged range from 6.80 ppm to 7.80 ppm in Figure 36(A). This shows that N-(chlorophenyl-4-yl)-N-(9,9-diphenyl-9H-fluoren-2-yl)dibenzofuran-2-amine was obtained in this step.

[0652] [ka]

[0653] 1 H NMR (dichloromethane-d2, 500MHz, 20℃): δ=7.76(d, J=7.5 Hz, 1H), δ=7.67(d, J=8.5 Hz, 1H), δ=7.66(d, J=2.5 Hz, 1H), δ=7.62(d, J=8.0 Hz, 1H), δ=7.54(d, J=8.0 Hz, 1H), δ=7.45-7.42(m, 2H), δ=7.34-7.27(m, 3H), δ=7.20(d, J=7.5 Hz, 1H), δ=7.18-7.14(m, 9H), δ=7.13(d, J=2.0Hz, 1H), δ=7.10-7.08(m, 4H), δ=7.01(dd, J=8.5 Hz, 2.0 Hz, 1H), δ=7.00-6.97(m, 2H)

[0654] <Step 2: Synthesis of Fr(2)FLP(2)A(βN2)B> The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 4. The synthesis scheme (s6-2) of Step 2 is shown below. 1 H NMR was measured, and the values ​​are shown below in the charts in Figures 37(A) and (B). Note that Figure 37(B) is a chart showing an enlarged range from 7.00 ppm to 8.40 ppm in Figure 37(A). This shows that Fr(2)FLP(2)A(βN2)B was obtained in this synthesis example.

[0655] [ka]

[0656] 1H NMR (dichloromethane-d2, 500MHz, 20℃): δ=8.20(s, 2H), δ=8.06(s, 1H), δ=8.01-7.87(m, 7H), δ=7.80-7.77(m, 2H), δ=7.76(d, J=2.5 Hz, 2H), δ=7.70(d, J=7.5Hz, 1H), δ=7.65(d, J=8.0 Hz, 1H), δ=7.62(d, J=7.0 Hz, 2H), δ=7.55(d, J=8.0 Hz, 1H), δ=7.53-7.43(m, 4H), δ=7.36-7.25(m, 5H), δ=7.22(d, J=7.0 Hz, 1H), δ=7.19-7.10(m, 12H)

[0657] The results of measuring the physical properties of Fr(2)FLP(2)A(βN2)B are shown in the table below. The measurements of each physical property were performed in the same manner as described in Example 1. As a result, no absorption band was observed for Fr(2)FLP(2)A(βN2)B at wavelengths longer than 440 nm, and it is considered that there is no decrease in the luminous efficiency of light-emitting devices due to absorption in the visible light wavelength region, and therefore it can be suitably used. It was also shown to be a substance with high heat resistance.

[0658] [Table 6] EXAMPLES

[0659] Synthesis Example 7 In this synthesis example, N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9'-diphenyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrFLP(2)A(βN2)B) was synthesized, which is shown as structural formula (148) in the first embodiment. The structural formula of FrFLP(2)A(βN2)B is shown below.

[0660] [ka]

[0661] <Step 1: Synthesis of N-(chlorophenyl-4-yl)-N-(9,9-diphenyl-9H-fluoren-2-yl)dibenzofuran-4-amine> The synthesis was carried out in the same manner as in step 2 of Example 1. The synthesis scheme (s7-1) of step 1 is shown below. 1 H NMR was measured, and the values ​​are shown below, and the charts are shown in Figures 38(A) and (B). Note that Figure 38(B) is a chart showing an enlarged range from 6.80 ppm to 8.20 ppm in Figure 38(A). This shows that N-(chlorophenyl-4-yl)-N-(9,9-diphenyl-9H-fluoren-2-yl)dibenzofuran-4-amine was obtained in this step.

[0662] [ka]

[0663] 1 H NMR (dichloromethane-d2,500MHz, 20℃): δ=7.98(d, J=7.5 Hz, 1H), δ=7.78(dd, J=7.5 Hz, 1.0Hz, 1H), δ=7.72(d, J=7.5 Hz, 1H), δ=7.68(d, J=8.5 Hz, 1H), δ=7.42-7.34(m, 4H), δ=7.32-7.17(m, 7H), δ=7.14-7.09(m, 7H), δ=7.06-7.01(m, 6H)

[0664] <Step 2: Synthesis of FrFLP(2)A(βN2)B> The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 4. The synthesis scheme (s7-2) of Step 2 is shown below. 1 H NMR was measured, and the values ​​are shown below in the charts in Figures 39(A) and (B). Note that Figure 39(B) is a chart showing an enlarged range from 6.80 ppm to 8.40 ppm in Figure 39(A). This shows that FrFLP(2)A(βN2)B was obtained in this synthesis example.

[0665] [ka]

[0666] 1 H NMR (dichloromethane-d2,500MHz, 20℃): δ=8.20(s, 2H), δ=8.06(s, 1H), δ=8.00-7.87(m, 8H), δ=7.78(d, J=7.0 Hz, 2H), δ=7.71(d, J=7.5 Hz, 1H), δ=7.69(d, J=8.0 Hz, 1H), δ=7.62(d, J=9.0 Hz, 2H), δ=7.53-7.47(m, 2H), δ=7.41-7.25(m, 7H), δ=7.22-7.15(m, 5H), δ=7.10-7.00(m, 10H)

[0667] The results of measuring the physical properties of FrFLP(2)A(βN2)B are shown in the table below. The measurements of each physical property were performed in the same manner as described in Example 1. As a result, no absorption band was observed for FrFLP(2)A(βN2)B at wavelengths longer than 440 nm, and it is believed that there will be no decrease in the luminous efficiency of light-emitting devices due to absorption in the visible light wavelength region, making it suitable for use. It was also shown to be a substance with high heat resistance.

[0668] [Table 7] EXAMPLES

[0669] Synthesis Example 8 In this synthesis example, N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-[9,9'-spirobi[9H-fluoren]-2-yl]dibenzofuran-4-amine (abbreviation: FrSFA(βN2)B) shown as structural formula (100) in embodiment 1 was synthesized. The structural formula of FrSFA(βN2)B is shown below.

[0670] [ka]

[0671] <Step 1: Synthesis of FrSFA(βN2)B> The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 4. The synthesis scheme (s8) of Step 1 is shown below. 1 H NMR was measured, and the values ​​are shown below in the charts in Figures 40(A) and (B). Note that Figure 40(B) is a chart showing an enlarged range from 6.80 ppm to 8.40 ppm in Figure 40(A). This shows that FrSFA(βN2)B was obtained in this synthesis example.

[0672] [ka]

[0673] 1 H NMR (dichloromethane-d2, 500MHz, 20℃): δ=8.18(d, 6.5 Hz, 2H), δ=8.01(s, 1H), δ=7.98-7.87(m, 8H), δ=7.77(t, J=8.0 Hz, 2H), δ=7.74-7.68(m, 4H), δ=7.54-7.47(m, 4H), δ=7.38(t, J=7.0 Hz, 1H), δ=7.33(d, J=9.5 Hz, 1H), δ=7.31(t, J=8.5 Hz, 2H), δ=7.25(t, J=7.5 Hz, 2H), δ=7.19(t, J=7.5 Hz, 1H), δ=7.18(dd, J=8.5 Hz, 2.0 Hz, 1H), δ=7.13(d, J=7.5 Hz, 1H), δ=7.04-6.97(m, 5H), δ=6.73(d, J=8.5 Hz, 2H), δ=6.58(d, J=7.5 Hz, 1H), δ=6.51(d, J=2.0 Hz, 1H)

[0674] The results of measuring the physical properties of FrSFA(βN2)B are shown in the table below. The measurements of each physical property were performed in the same manner as described in Example 1. As a result, no absorption band was observed for FrSFA(βN2)B at wavelengths longer than 440 nm, and it is believed that there will be no decrease in the luminous efficiency of light-emitting devices due to absorption in the visible light wavelength region, making it suitable for use. It was also shown to be a substance with high heat resistance.

[0675] [Table 8] [Explanation of symbols]

[0676] 100A display device 100B display device 100C display device 100E display device 100D display device 100 Insulator 100S Insulator 101B First electrode 101G First electrode 101R First electrode 101S First electrode 101 First electrode 102 Second electrode 102S Second electrode 103Bf Organic compound film 103Gf organic compound film 103Rf Organic compound film 103 Organic compound layer 103S organic compound layer 110B subpixel 110G subpixel 110R subpixel 110 subpixels 111 Hole injection layer 111S Hole injection layer 112 Hole transport layer 112S Hole transport layer 112B Conductive layer 112R conductive layer 113 Light-emitting layer 114 Electron transport layer 114S electron transport layer 115 Electron injection layer 115S electron injection layer 116 Charge generation layer 117 P type layer 118 Electronic Relay Layer 119 Electron injection buffer layer 120 Substrate 122 Resin layer 123 Photoelectric conversion layer 124 light 125f Inorganic insulating film 125 Inorganic insulating layer 126R conductive layer 126B Conductive layer 127a Insulating layer 127f Insulating film 127 Insulating Layer 128 layers 129R conductive layer 129B Conductive layer 130B Light Emitting Device 130G Light Emitting Device 130R Light Emitting Device 130 Light Emitting Devices 131 Protective layer 132B Colored layer 132G colored layer 132R colored layer 135 First Layer 135A First Group 135R 1st layer 135G 1st layer 135B First Layer 136 Common layer 140 Connection 141 areas 142 Adhesive layer 151B Conductive layer 151C conductive layer 151f Conductive film 151G conductive layer 151R conductive layer 151 Conductive layer 152B Conductive layer 152C conductive layer 152f Conductive film 152G Conductive layer 152R Conductive layer 152 Conductive layer 153 Insulating Layer 155 Second Electrode 156B Insulating layer 156C Insulating layer 156f Insulating film 156G Insulation layer 156R Insulation layer 156 Insulating Layer 157 Light blocking layer 158B Sacrificial Layer 158Bf sacrificial film 158G Sacrificial Layer 158Gf sacrificial film 158R Sacrificial layer 158Rf Sacrificial film 159B Mask layer 159Bf Mask membrane 159G Mask layer 159Gf Mask Film 159R Mask layer 159Rf Mask Film 166 Conductive Layer 171 Insulating Layer 172 Conductive Layer 173 Insulating Layer 174 Insulating Layer 175 Insulating Layer 176 Plug 177 Pixel section 178 pixels 179 Conductive Layer 190B Resist mask 190G Resist Mask 190R Resist Mask 191 Resist Mask 201 Transistor 204 Connection 205 Transistor 211 Insulating layer 213 Insulating Layer 214 Insulating layer 215 Insulating Layer 221 Conductive Layer 222a conductive layer 222b Conductive layer 223 Conductive Layer 224B Conductive layer 224C conductive layer 224G conductive layer 224R conductive layer 231 Semiconductor Layer 240 capacity 241 Conductive Layer 242 Connection Layer 243 Insulating Layer 245 Conductive Layer 254 Insulating layer 255 Insulation Layer 256 Plug 261 Insulating Layer 271 Plug 280 Display Module 281 Display section 282 Circuit section 283a Pixel circuit 283 Pixel circuit section 284a pixels 284 Pixel section 285 Terminal section 286 Wiring section 290 FPC 291 Substrate 292 Substrate 301 Substrate 310 Transistor 311 Conductive layer 312 Low resistance region 313 Insulating Layer 314 Insulating layer 315 Element isolation layer 351 Substrate 352 Substrate 353 FPC 354 IC 355 Wiring 356 circuits 501 First electrode 502 Second electrode 513 Charge generation layer 700A electronic equipment 700B Electronic equipment 721 Case 723 Mounting Part 727 Earphones 750 Earphones 751 Display Panel 753 Optical Components 756 Display area 757 Frames 758 Nose pad 800A electronic equipment 800B Electronic equipment 820 Display section 821 Case 822 Communications Department 823 Mounting part 824 Control Unit 825 Imaging unit 827 Earphones 832 Lens 6500 Electronic equipment 6501 Case 6502 Display section 6503 Power button 6504 Button 6505 Speaker 6506 Microphone 6507 Camera 6508 Light source 6510 Protective materials 6511 Display Panel 6512 Optical components 6513 Touch Sensor Panel 6515 FPC 6516 IC 6517 Printed Circuit Board 6518 Battery 7000 Display 7100 Television equipment 7151 Remote control device 7171 Case 7173 Stand 7200 Notebook Personal Computer 7211 Case 7212 Keyboard 7213 Pointing Device 7214 External connection port 7300 Digital Signage 7301 Case 7303 Speaker 7311 Information terminal 7400 Digital Signage 7401 Pillar 7411 Information terminal 9000 Chassis 9001 Display section 9002 Camera 9003 Speaker 9005 Operation key 9006 Connection terminal 9007 Sensor 9008 Microphone 9050 Icon 9051 Information 9052 Information 9053 Information 9054 Information 9055 Hinge 9171 Mobile Information Terminal 9172 Mobile Information Terminal 9173 Tablet PC 9200 Mobile Information Terminal 9201 Portable information terminals

Claims

1. An organic compound represented by general formula (G1): 【Chemistry 1】 (In the general formula (G1), X represents a sulfur atom or an oxygen atom, and R １ ~R ２２ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R １６ ~R ２２ At least one of R represents a substituted or unsubstituted naphthyl group, n represents an integer of 0 to 4, and when n is 2 or more, a plurality of R １２ ~R １５ may be the same or different. １ is represented by the following general formula (g1-1) or the following general formula (g1-2): 【Chemistry 2】 (In the general formula (g1-1) and the general formula (g1-2), R ２３ ~R ３０ Either one of or R ３３ ~R ４８ Any one of the above is bonded to the nitrogen of the amine in general formula (G1), and the other and R ３１ , R ３２ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

2. In claim 1, The organic compound wherein n is 0 or 1.

3. An organic compound represented by general formula (G2): 【Chemistry 3】 (In the general formula (G2), X represents a sulfur atom or an oxygen atom, and R １ ~R １１ and R １６ ~R ２２ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R １６ ~R １９ At least one of Ar represents a substituted or unsubstituted naphthyl group. １ is represented by the following general formula (g1-1) or the following general formula (g1-2): 【Chemistry 4】 (In the general formula (g1-1) and the general formula (g1-2), R ２３ ~R ３０ Either one of or R ３３ ~R ４８ Any one of the following bonds to the nitrogen atom of the amine in general formula (G2); ３１ , R ３２ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

4. An organic compound represented by general formula (G3): 【Chemistry 5】 (In the general formula (G3), X represents a sulfur atom or an oxygen atom, and R １ ~R １１ and R １６ ~R ２２ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R １６ ~R ２２ At least one of Ar represents a substituted or unsubstituted naphthyl group. １ is represented by the following general formula (g1-1) or the following general formula (g1-2): 【Chemistry 6】 (In the general formula (g1-1) and the general formula (g1-2), R ２３ ~R ３０ Either one of or R ３３ ~R ４８ Any one of the above is bonded to the nitrogen of the amine in general formula (G3), and the other and R ３１ , R ３２ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

5. In any one of claims 1 to 4, The R １６ ~R ２２ any one of the above is a group represented by general formula (g2): 【Chemistry 7】 (However, in general formula (g2), R ４９ ~R ５５ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

6. An organic compound represented by general formula (G4): 【Chemistry 8】 (In the general formula (G4), X represents a sulfur atom or an oxygen atom, and R １ ~R １１ , R １６ , R １７ , R １９ ~R ２２ and R ４９ ~R ５５ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. １ is represented by the following general formula (g1-1) or the following general formula (g1-2): 【Chemistry 9】 (In the general formula (g1-1) and the general formula (g1-2), R ２３ ~R ３０ Either one of or R ３３ ~R ４８ Any one of the following bonds to the nitrogen atom of the amine in general formula (G4); ３１ , R ３２ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

7. An organic compound represented by general formula (G5): 【Chemistry 10】 (In the general formula (G5), X represents a sulfur atom or an oxygen atom, and R １ ~R １１ and R １６ , R １７ , R １９ ~R ２８ , R ３０ ~R ３２ and R ４９ ~R ５５ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

8. An organic compound represented by general formula (G6): 【Chemistry 11】 (In the general formula (G6), X represents a sulfur atom or an oxygen atom, and R １ ~R １１ and R １６ , R １７ , R １９ ~R ２２ and R ３３ ~R ３８ , R ４０ ~R ５５ each independently represents any one of hydrogen (including deuterium), halogen, a nitrile group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

9. An organic semiconductor device comprising the organic compound according to any one of claims 1 to 4.

10. A light emitting device comprising an organic compound according to any one of claims 1 to 4.

11. An electronic device comprising the organic semiconductor device according to claim 9.

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