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

Abstract

Provided is an organic compound which is capable of providing an organic semiconductor device, a light-emitting device, and an electronic device that have excellent hole transport properties and high reliability. Provided is an organic compound represented by general formula (G1). In general formula (G1), X represents a sulfur atom or an oxygen atom; r1 to R22 each independently represent any one of hydrogen (including deuterium), halogen, a nitrile group, an alkenyl group, a vinyl group, an alkynyl group, a linear alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms. At least one of R16 to R22 represents a naphthyl group, n represents an integer of 0 to 4, and Ar1 represents a fluorenyl group or a spirofluorenyl group. # imgabs0 #

Description

Technical Field

[0001] One embodiment of the present invention relates to an organic compound, an organic electronic device, a light-emitting device, and an electronic device.

[0002] Note that one embodiment of the present invention is not limited to the above-mentioned technical field. As an example of the technical field of one embodiment of the present invention, a compound, a light-emitting device, a semiconductor device, a display device, a light-emitting device, a power storage device, a storage device, an electronic device, a lighting device, an input device (e.g., a touch sensor), an input-output device (e.g., a touch panel), and a driving method or a manufacturing method of the above-mentioned device can be cited. Background Art

[0003] In recent years, display devices are expected to be used in various applications. For example, as a large display device, there are household television devices (also called televisions or television receivers), digital signage (Digital Signage: electronic billboards) and public information displays (PID: Public Information Display). In addition, as portable information terminals, research and development of smartphones and tablet terminals including touch panels is underway.

[0004] In addition, there is a demand for higher-definition display devices. Devices that require high-definition display devices include those for virtual reality (VR), augmented reality (AR), alternative reality (SR), and mixed reality (MR).

[0005] As display devices, light-emitting devices including light-emitting devices (also called light-emitting elements) using organic compounds have been developed. Light-emitting devices using the electroluminescence (hereinafter referred to as EL) phenomenon (also called organic "EL devices" or "light-emitting devices") have the characteristics of being easy to achieve thinness and lightness; being able to respond to input signals at high speed; and being able to be driven using a DC constant voltage power supply, etc., and have been applied to display devices.

[0006] Displays and lighting devices using light-emitting devices are applicable to various electronic devices. However, in pursuit of light-emitting devices with better characteristics, research and development of both materials and devices is still ongoing (for example, see Patent Document 1).

[0007] [Patent Document 1] International Patent Application Publication No. 2021 / 132995 Summary of the invention

[0008] The purpose of one embodiment of the present invention is to provide a novel organic compound. In addition, the purpose of one embodiment of the present invention is to provide a novel carrier transport material. In addition, the purpose of one embodiment of the present invention is to provide a novel hole transport material. In addition, the purpose of one embodiment of the present invention is to provide a carrier transport material or hole transport material with high heat resistance.

[0009] Another aspect of the present invention provides a light emitting device with low driving voltage. Another aspect of the present invention provides a light emitting device, a light emitting device, an electronic device, and a display device with low power consumption.

[0010] Note that the description of these objectives does not prevent the existence of other objectives. One embodiment of the present invention does not need to achieve all of the above objectives. Objectives other than the above objectives can be extracted from the description of the specification, drawings, and claims.

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

[0012] [Chemical formula 1]

[0013] Note that in the general formula (G1), X represents a sulfur atom or an oxygen atom, and R 1 To R 22 each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted linear alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, and R 16 To R 22 At least one of them represents a substituted or unsubstituted naphthyl group, n represents an integer from 0 to 4, and when n is 2 or more, a plurality of R 12 To R 15 They may also be the same or different from each other. 1 It is represented by the following general formula (g1-1) or the following general formula (g1-2).

[0014] [Chemical formula 2]

[0015] Note that in the general formula (g1-1) and the general formula (g1-2), R 23 To R 30 Any one or R33 To R 48 Any one of them is bonded to the nitrogen of the amine in the general formula (G1), and the others and R 31 , R 32 Each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.

[0016] Another embodiment of the present invention is an organic compound wherein 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] [Chemical formula 3]

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

[0020] [Chemical formula 4]

[0021] Note that in the general formula (g1-1) and the general formula (g1-2), R 23 To R 30 Any one or R 33 To R 48Any one of them is bonded to the nitrogen of the amine in the general formula (G2), and the others and R 31 , R 32 Each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl 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] [Chemical formula 5]

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

[0025] [Chemical formula 6]

[0026] Note that in the general formula (g1-1) and the general formula (g1-2), R 23 To R 30 Any one or R 33 To R 48 Any one of is bonded to the nitrogen of the amine in the general formula (G3), and the others and R 31 , R 32Each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.

[0027] Another embodiment of the present invention is that in the above structure, R 16 To R 22 Any one of them is an organic compound represented by the following general formula (g2).

[0028] [Chemical formula 7]

[0029] Note that in general formula (g2), R 49 To R 55 Each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl 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] [Chemical formula 8]

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

[0033] [Chemical formula 9]

[0034] Note that in the general formula (g1-1) and the general formula (g1-2), R 23 To R 30 Any one or R 33 To R 48 Any one of is bonded to the nitrogen of the amine in the general formula (G4), and the other and R 31 , R 32 Each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl 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] [Chemical formula 10]

[0037] Note that in the general formula (G5), X represents a sulfur atom or an oxygen atom, and R 1 To R 11 and R 16 , R 17 , R 19 To R 28 , R 30 To R 32 and R 49 To R 55Each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl 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] [Chemical formula 11]

[0040] Note that in the general formula (G6), X represents a sulfur atom or an oxygen atom, and R 1 To R 11 and R 16 , R 17 , R 19 To R 22 and R 33 To R 38 , R 40 To R 55 Each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.

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

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

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

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

[0045] Another embodiment of the present invention is an organic electronic device using any one of the above-mentioned organic compounds for a cover layer.

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

[0047] According to one embodiment of the present invention, a novel organic compound can be provided. In addition, according to one embodiment of the present invention, a novel carrier transport material can be provided. In addition, according to one embodiment of the present invention, a novel hole transport material can be provided. In addition, according to one embodiment of the present invention, a carrier transport material or hole transport material with high 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] According to 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 prevent the existence of other effects. One embodiment of the present invention does not necessarily have all of the above effects. Effects other than the above effects can be extracted from the description of the specification, drawings, and claims. BRIEF DESCRIPTION OF THE DRAWINGS

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

[0052] The embodiments are described in detail with reference to the accompanying drawings. Note that the present invention is not limited to the following description, and a person skilled in the art can easily understand that the method and details can be transformed into various forms without departing from the purpose and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the contents described in the embodiments shown below.

[0053] Implementation Method 1 In this embodiment, an organic compound which is one embodiment of the present invention is described.

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

[0055] [Chemical formula 12]

[0056] In the organic compound represented by the above general formula (G1), R 16 To R 22 At least one of them represents a substituted or unsubstituted naphthyl group, and the others and R 1 To R 15Respectively independently represent hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted linear alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, and particularly preferably represent hydrogen (including deuterium), substituted or unsubstituted linear alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, because a material having high heat resistance and low sublimation temperature can be provided. When using a material having high heat resistance, an organic semiconductor device (light-emitting device, light-receiving device, etc.) having high heat resistance can be provided, which can be appropriately used for vehicle-mounted applications requiring high heat resistance. Furthermore, when a material having a low sublimation temperature is used, when an organic semiconductor device is manufactured by vapor deposition, thermal decomposition occurring in the heating step required for vapor deposition can be prevented or reduced, so that a high-purity film can be provided, and as a result, a highly reliable organic semiconductor device can be provided, which is preferred. Furthermore, when a material having an alkyl group or a cycloalkyl group is used, a film having a low refractive index can be formed, and thus, when the material of the present invention is used in a transmission layer of a light-emitting device, a device having high light extraction efficiency can be provided, which is preferred. Furthermore, R other than a naphthyl group 16 To R 22 and R 1 To R 15 Hydrogen is preferred because synthesis is easy.

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

[0058] R 16 To R 22 At least one of them is a substituted or unsubstituted naphthyl group, and R 16 To R 22 One or two of them are substituted or unsubstituted naphthyl groups, so that a device with small voltage fluctuation when the device is continuously driven can be realized, and an organic semiconductor device with stable voltage when driven can be provided, so it is preferred. Moreover, since only one of them is substituted or unsubstituted naphthyl groups, the evaporation temperature will not be too high, and it has high hole transport properties, so it is preferred.

[0059] In the organic compound represented by the above general formula (G1), n ​​represents an integer from 0 to 4. When n is 2 or more, a plurality of R 12 To R15 They may be the same or different from each other. Note that when n is 0 or 1, the evaporation temperature will not be too high, the hole transport property is improved, and an organic semiconductor device with high reliability and small voltage change during driving is provided, so it is preferred. In addition, in order to improve the hole transport property, the phenylene bonded to the amine is preferably a p-phenylene, but when three or more phenylenes are bonded to the para position, the effective conjugation length is extended, so the absorption wavelength may be extended to visible light, in which case the light extraction efficiency of the light-emitting device may be reduced. Therefore, n is preferably 0 or 1, and when n is 2 or more, it is preferred to bond in the meta position where the effective conjugation length is not easily extended or in the ortho position due to the generation of stereo distortion, compared with the para position.

[0060] In the above-mentioned organic compound represented by the general formula (G1), X is a sulfur atom or an oxygen atom. Since when X is an oxygen atom, the refractive index is lower than that of the compound containing a sulfur atom, and the device of the compound with a low refractive index produces an effect of improving the light extraction efficiency, a high-efficiency light-emitting device can be provided, so it is preferred. In addition, when X is a sulfur atom, the heat resistance is improved compared to the compound containing an oxygen atom, so a device resistant to high-temperature driving can be provided, so it is preferred. In addition, when sulfur is used, the refractive index is improved, so by depositing a film as a high-refractive-index film on the upper part of the cathode, a light-emitting device with high light extraction efficiency can be provided.

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

[0062] [Chemical formula 13]

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

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

[0065] An organic compound having such a structure can realize a material having both excellent hole transport properties and high heat resistance. In addition, since the film quality changes little in a thin film containing an organic compound having such a structure, a device that is stable to heat or driving can be provided, so it is preferred. In addition, a device using an organic compound having such a structure can be a device that has a low driving voltage and small voltage variation during driving, so it has high reliability to voltage, and has high reliability in high-temperature driving. In addition, a low-power device can be realized, so it is preferred. In addition, since an organic compound having such a structure has high sublimation and does not decompose during the evaporation process, a high-purity film can be deposited, so a highly reliable organic semiconductor device can be provided, so it is preferred, and stable production can be achieved, so it is preferred in terms of manufacturing cost.

[0066] Among the organic compounds represented by the general formula (G1), when n is 0, the evaporation temperature is not too high, the hole transport property is improved, and a highly reliable organic semiconductor device is provided, and a highly reliable organic semiconductor device with a small voltage change during driving is provided, so it is preferred. 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] [Chemical formula 14]

[0068] In the above general formula (G2), R 1 To R 11 , R 16 To R 22 and Ar 1 Since it is the same as the above-mentioned general formula (G1), repeated description is omitted.

[0069] In addition, in the organic compound represented by the above general formula (G2), the naphthyl group bonded to the p-phenylene group is preferably bonded to the p-phenylene group at the 2-position to achieve high hole transport properties and high reliability during driving, so it is preferred. 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] [Chemical formula 15]

[0071] In the above general formula (G3), R 1 To R 11 , R 16 To R 22 and Ar 1 Since it is the same as the above-mentioned general formula (G1), repeated description is omitted.

[0072] In the organic compounds represented by the above general formula (G1) to the above general formula (G3), R 16 To R 22 At least one of them is a substituted or unsubstituted naphthyl group. When the substituted or unsubstituted naphthyl group is a substituted or unsubstituted 2-naphthyl group represented by the following general formula (g2), high hole transport properties and high reliability during driving are achieved, which is preferred.

[0073] [Chemical formula 16]

[0074] In the above general formula (g2), R 49 To R 55Each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted linear alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms. In addition, in R 49 To R 55 When each independently represents any one of hydrogen (including deuterium), halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted linear alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, and substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, it has high hole transport properties, high heat resistance, and high stability of the thin film, so it is preferred. 49 To R 55 When hydrogen (including deuterium) and any one of a substituted or unsubstituted straight-chain alkyl group having 1 to 6 carbon atoms are represented independently, the sublimation temperature and the vapor deposition temperature can be lowered, and thermal decomposition during vapor deposition can be inhibited, so it is more preferred. When hydrogen (including deuterium) is represented, the synthesis cost can be reduced, so it is further preferred.

[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 p-phenylene group, and when the binaphthyl group is a substituted or unsubstituted 2,2'-binaphthyl-6-yl group, the driving voltage of an organic semiconductor device using the organic compound of one embodiment of the present invention is reduced, the voltage variation for driving is small, the power consumption is small, the device has high heat resistance, or the reliability for driving is improved, so it is preferred. 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] [Chemical formula 17]

[0077] In the above general formula (G4), R 1 To R 11 , R 16 , R 17 , R 19 To R 22 Same as the above general formula (G1) and R 49 To R 55 Since it is the same as the above-mentioned general formula (g2), repeated description is omitted.

[0078] In the above structure in another embodiment of the present invention, in Ar 1 When it is a substituted or unsubstituted fluorene-2-yl group, the highest occupied molecular orbital energy level (HOMO energy level) is high, and it becomes an organic compound with high hole transport properties. Therefore, when used in a light-emitting device, a light-emitting device with low driving voltage can be provided, a light-emitting device with high luminous efficiency can be provided, and a device with high reliability can be provided, so it is preferred. 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] [Chemical formula 18]

[0080] In the above general formula (G5), R 1 To R 11 , R 16 , R 17 , R 19 To R 22 As in the above general formula (G1), R 23 To R 28 , R 30 To R 32 As in the above general formula (g1-1), R 49 To R 55 Since it is the same as the above-mentioned general formula (g2), repeated description is omitted.

[0081] Another embodiment of the present invention is an organic compound of the above structure, wherein Ar 1 It is a substituted or unsubstituted 9,9'-spirodi[9H-fluorene]-2-yl, whereby the HOMO energy level is relatively high, and thus an organic compound with high hole transport properties can be provided. In addition, since the HOMO energy level of the organic compound is relatively high, the hole injection property of the phosphorescent device for the light-emitting layer comprising the organic compound with a high HOMO energy level, especially the mixed host of the bipolar-host or the hole transport host and the electron transport host is good. Therefore, by using the organic compound as a material for the hole transport layer in contact with the light-emitting layer in a phosphorescent light-emitting device, especially in a green phosphorescent light-emitting device and a red phosphorescent light-emitting device, a phosphorescent light-emitting device with high reliability and low driving voltage during high temperature driving can be provided. In addition, a light-emitting device with high luminous efficiency can be provided. In addition, a device with high reliability can be provided.

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

[0083] [Chemical formula 19]

[0084] In the above general formula (G6), R 1 To R 11 , R 16 , R 17 , R 19 To R 22 As in the above general formula (G1), R 33 To R 38 , R 40 To R 48 As in the above general formula (g1-2), R 49 To R 55 Since it is the same as the above-mentioned general formula (g2), repeated description is omitted.

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

[0086] In addition, in the general formulas (G1) to (G6), the general formula (g1-1), the general formula (g1-2) and the general formula (g2), as the alkenyl group, for example, vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, sec-butenyl, isobutenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, isopentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 5-octenyl, 6-octenyl and 7-octenyl can be mentioned.

[0087] In addition, in the general formulas (G1) to (G6), the general formula (g1-1), the general formula (g1-2) and the general formula (g2), as the alkynyl group, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, sec-butynyl, isobutynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, isopentinyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-heptynyl, 2-heptynyl, 3-heptynyl, 4-heptynyl, 5-heptynyl, 6-heptynyl, 1-octynyl, 2-octynyl, 3-octynyl, 4-octynyl, 5-octynyl, 6-octynyl and 7-octynyl can be mentioned.

[0088] In general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), specific examples of the straight-chain alkyl group having 1 to 6 carbon atoms include methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl. Note that when the straight-chain 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 general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), specific examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, bicyclo[2.2.1]heptyl, tricyclo[5.2.1.0(2,6)]decyl and noradamantyl. Note that 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 general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), specific examples of the alkoxy group having 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, pentyloxy, octyloxy, allyloxy, cyclohexyloxy, phenoxy, benzyloxy, vinyloxy, propenyloxy, butenyloxy, pentenyloxy and hexenyloxy. Note that 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 the general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), examples of the alkylsilyl group having 3 to 12 carbon atoms include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, triisopropylsilyl, tri-tert-butylsilyl and tributylsilyl. Note that 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 general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), examples of the aryl group having 6 to 30 carbon atoms include phenyl, tolyl, benzyl, biphenyl, indenyl, naphthyl, fluorenyl, spirofluorenyl, phenanthryl, triphenylene, anthracene, fluoranthenyl and the like. Note that 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 pyridyl, pyrimidinyl, triazine, phenanthroline, carbazolyl, pyrrolyl, thienyl, furanyl, imidazolyl, bipyridyl, bipyrimidinyl, pyrazinyl, bipyrazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, benzoquinoxalinyl, dibenzoquinoxalinyl, azofluorenyl, disazofluorenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzocarbazolyl, Benzofuranyl, benzonaphthofuranyl, dinaphthofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, dinaphthothiophenyl, benzofuranopyridyl, benzofuranopyrimidyl, benzothiophenopyridyl, benzothiophenopyrimidyl, naphthofuranopyridyl, naphthofuranopyrimidyl, naphthothiophenopyrimidyl, dibenzoquinoxalinyl, acridinyl, xanthyl, phenothiazinyl, phenoxazinyl, phenazinyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, benzimidazolyl, or pyrazolyl. Note that 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] In addition, hydrogen contained in the general formulas (G1) to (G6), the general formula (g1-1), the general formula (g1-2) and the general formula (g2) includes deuterium.

[0095] In addition, when the above-mentioned alkenyl, vinyl, alkynyl, cycloalkyl, alkoxy, alkylsilyl, aryl, heteroaryl are bases with substituents, as the substituent, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl having 6 to 12 carbon atoms can also be selected. As the alkyl having 1 to 6 carbon atoms, specifically, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl and n-hexyl can be mentioned. In addition, as the cycloalkyl having 3 to 6 carbon atoms, specifically, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl can be mentioned. In addition, as a specific example of the aryl having 6 to 12 carbon atoms, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl can be mentioned.

[0096] When the straight-chain 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. Specifically, the cycloalkyl group having 3 to 6 carbon atoms includes, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. In addition, 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, a substituted or unsubstituted biphenyl group, etc.

[0097] Among the organic compounds represented by the above-mentioned general formulae (G1) to (G6), (g1-1), (g1-2) and (g2), as the organic compounds that can be used as R 1 To R 55 Specific examples of the element or group include groups represented by the following structural formulae (1-1) to (1-35) and (2-1) to (2-60). Note that as a group without a bond, a monovalent group in which any of the hydrogen atoms contained in the group is detached can be used.

[0098] [Chemical formula 20]

[0099] [Chemical formula 21]

[0100] [Chemical formula 22]

[0101] [Chemical formula 23]

[0102] An organic compound of one embodiment of the present invention having the above structure can realize a material having both excellent hole transport properties and high heat resistance. In addition, since the film quality changes little in the thin film containing the organic compound having such a structure, a device that is stable to heat or driving time can be provided, so it is preferred. In addition, the device using the compound having such a structure can be a device as follows: the driving voltage is low and the voltage variation during driving is small, so it has high reliability to voltage and has high reliability in high-temperature driving. In addition, a low-power device can be realized. In addition, the organic compound having such a structure has high sublimation, does not decompose in the evaporation process, and can achieve stable production, so it is preferred from the perspective of manufacturing cost.

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

[0104] [Chemical formula 24]

[0105] In the above general formula (G1), R 1 To R 22 , X, n, Ar 1 The same as in this embodiment.

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

[0107] [Chemical formula 25]

[0108] [Chemical formula 26]

[0109] In the synthesis schemes (a-1) and (a-2), Q 1 and Q 2 Each independently represents chlorine, bromine, iodine, or trifluoromethanesulfonate. 1 To R 22 , X, n, Ar 1 The same as the organic compound represented by the general formula (G1).

[0110] As an organic compound represented by the general formula (G1), first, as in the above-mentioned synthesis scheme (a-1), by making a 1 The compound having a fluorene skeleton represented by ((g1-1) or (g1-2)) (Compound 1) is cross-coupled with an amine compound having a dibenzofuran skeleton or a dibenzothiophene skeleton (Compound 2) to obtain a 1 A dibenzofuranylamine or dibenzothienylamine compound having a fluorene skeleton (Compound 3) is represented.

[0111] Next, according to the above synthesis scheme (a-2), a 1 The dibenzofuranylamine or dibenzothienylamine compound (compound 3) having a fluorene skeleton represented by the cross coupling with the compound (compound 4) having a binaphthyl skeleton can obtain a compound having a binaphthyl skeleton and composed of Ar 1 An organic compound of one embodiment of the present invention represented by the general formula (G1) having a fluorene skeleton represented by and a dibenzofuran skeleton or a dibenzothiophene skeleton.

[0112] The above-mentioned synthesis schemes (a-1) and (a-2) can utilize the Buchwald-Hartwig reaction using a palladium catalyst. In this case, as the palladium catalyst, palladium compounds such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium(0), and allylpalladium(II) chloride dimer can be used, and as the ligand, tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(o-tolyl)phosphine, (S)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diisopropylphosphine) (abbreviated as: cBRIDP) and the like can be used.

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

[0114] In the above-mentioned synthesis schemes (a-1) and (a-2), a compound in which an organic tin group is bonded to the amino group of compound 2 or compound 3 may be used instead of compound 2 or compound 3.

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

[0116] [Chemical formula 27]

[0117] In the synthesis scheme (a-1-1), Q 3 represents chlorine, bromine, iodine, or trifluoromethanesulfonate. 1 To R 7 , X, Ar 1 The same as the organic compound represented by the general formula (G1). In addition, similar to the synthesis schemes (a-1) and (a-2), the Buchwald-Hartwig reaction using a palladium catalyst can be performed in the above synthesis scheme (a-1-1).

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

[0119] [Chemical formula 28]

[0120] [Chemical formula 29]

[0121] In the synthesis schemes (a-3) and (a-4), Q 2 and Q 3 Each independently represents chlorine, bromine, iodine, or trifluoromethanesulfonate. 1 To R 22 , X, n, Ar 1 The same as the organic compound represented by the general formula (G1). In addition, similar to the synthesis schemes (a-1) and (a-2), the Buchwald-Hartwig reaction using a palladium catalyst can be performed in the above synthesis schemes (a-3) and (a-4).

[0122] As an organic compound represented by the general formula (G1), first, as shown in the above-mentioned synthesis scheme (a-3), by making a 1 The amine compound (compound 5) having a fluorene skeleton represented by the cross coupling with the compound (compound 4) having a binaphthyl skeleton can obtain a compound having Ar 1 The amine compound having a fluorene skeleton and a binaphthyl skeleton (Compound 7) is represented.

[0123] Next, according to the synthesis scheme (a-4), a 1 The amine compound (compound 7) having a fluorene skeleton and a binaphthyl skeleton represented by the cross coupling with the compound (compound 6) having a dibenzofuran skeleton or a dibenzothiophene skeleton can obtain a compound having a binaphthyl skeleton and Ar 1 An organic compound of one embodiment of the present invention represented by the general formula (G1) having a fluorene skeleton represented by and a dibenzofuran skeleton or a dibenzothiophene skeleton.

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

[0125] [Chemical formula 30]

[0126] [Chemical formula 31]

[0127] In the synthesis schemes (a-3-1) and (a-3-2), Q 1 and Q 4 Each independently represents chlorine, bromine, iodine, or triflate. 8 To R 22 Each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms, R 8 To R 22They may also be bonded to each other to form a ring, and examples of the boron compound in this case include borane. 8 To R 22 , X, n, Ar 1 The same as the organic compound represented by the general formula (G1).

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

[0129] Next, as in the above-mentioned synthesis scheme (a-3-2), an amine compound having a binaphthyl skeleton (Compound 10) and a 1 Compound 7 can be obtained by cross-coupling the compound having a fluorene skeleton represented by (compound 1).

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

[0131] In this reaction, organic bases such as sodium tert-butoxide or inorganic bases such as potassium carbonate or sodium carbonate can be used as alkali. In addition, in this reaction, as solvent, a mixed solvent of toluene and water, a mixed solvent of dimethylbenzene and water, a mixed solvent of benzene and water, ethylene glycol dimethyl ether or 1,4-dioxane and a mixed solvent of ethers and water can be used. The higher the solubility of boric acid or boron compound to the water layer, the faster the reaction speed, the effect of yield improvement can be expected, so it is preferred to add water, but when ethers are used as solvent, it can be expected that the same effect can be obtained even if water is not added. In addition, a mixed solvent of alcohols such as toluene, water, ethanol, a mixed solvent of alcohols such as dimethylbenzene, water, ethanol, benzene, water, ethanol, etc. can be used as a reaction solvent. Particularly preferred are mixed solvents of ethers and water such as a mixed solvent of toluene and water, a mixed solvent of toluene and water and ethanol, and ethylene glycol dimethyl ether.

[0132] Alternatively, an organoaluminum compound, an organozirconium compound, an organozinc compound, an organotin compound or the like may be used in place of the organoboron compound or boric acid in the cross-coupling reaction with a compound having a halide or trifluoromethanesulfonate group.

[0133] In addition, in the above-mentioned synthesis scheme (a-3-2), a Buchwald-Hartwig reaction using a palladium catalyst can be carried out in the same manner as in the synthesis schemes (a-1) and (a-2).

[0134] In addition, the compound 10 synthesized in the above-mentioned synthesis scheme (a-3-1) can also be synthesized by the following synthesis scheme (a-3-1-1).

[0135] [Chemical formula 32]

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

[0137] In the above synthesis scheme (a-3-1-1), the boron compound having an aniline skeleton (Compound 11) and the compound having a binaphthyl skeleton (Compound 4) are cross-coupled to produce an aniline compound having a binaphthyl skeleton (Compound 10).

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

[0139] [Chemical formula 33]

[0140] [Chemical formula 34]

[0141] In the synthesis schemes (a-3-2-1) and (a-3-2-2), Q 1 and Q 4 Each independently represents chlorine, bromine, iodine, or triflate. 8 To R 22 Each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms, R 8 To R 22They may also be bonded to form a ring, and examples of the boron compound in this case include borane. In addition, R 8 To R 22 , X, n, Ar 1 The same as the organic compound represented by the general formula (G1).

[0142] First, as in the above-mentioned synthesis scheme (a-3-2-1), by making a 1 The compound having a fluorene skeleton represented by (compound 1) is cross-coupled with an aniline compound (compound 8) to obtain a phenyl group and a 1 An amine compound having a fluorene skeleton (Compound 12) is represented.

[0143] Next, as in the above-mentioned synthesis scheme (a-3-2-2), by making a phenyl group and Ar 1 The amine compound (compound 12) having a fluorene skeleton represented by the cross coupling with the boron compound (compound 9) having a binaphthyl skeleton can obtain a compound having a binaphthyl skeleton and Ar 1 The amine compound having a fluorene skeleton is represented (Compound 7).

[0144] In addition, similarly to the synthesis schemes (a-1) and (a-2), the Buchwald-Hartwig reaction using a palladium catalyst can be performed in the above synthesis scheme (a-3-2-1). In addition, similarly to the synthesis scheme (a-3-1), the Suzuki-Miyaura reaction using a palladium catalyst can be performed in the above synthesis scheme (a-3-2-2).

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

[0146] [Chemical formula 35]

[0147] [Chemical formula 36]

[0148] In the synthesis schemes (a-3) and (a-4), Q 1 and Q 2 Each independently represents chlorine, bromine, iodine, or trifluoromethanesulfonate. 1 To R 22 , X, n, Ar 1The same as the organic compound represented by the general formula (G1). In addition, similar to the synthesis schemes (a-1) and (a-2), the Buchwald-Hartwig reaction using a palladium catalyst can be performed in the above synthesis schemes (a-5) and (a-6).

[0149] In this synthesis scheme, first, as shown in the above-mentioned synthesis scheme (a-5), an amine compound (compound 2) having a dibenzofuran or dibenzothiophene skeleton is cross-coupled with a compound (compound 4) having a binaphthyl skeleton to obtain an amine compound (compound 16) having a binaphthyl skeleton and a dibenzofuranylamine skeleton or a dibenzothiophene skeleton.

[0150] Next, according to the synthesis scheme (a-6), an amine compound (compound 16) having a binaphthyl skeleton and a dibenzofuranylamine skeleton or a dibenzothiophene skeleton is reacted with a 1 The compound having a fluorene skeleton represented by (compound 1) can be cross-coupled to obtain a compound having a binaphthyl skeleton and Ar 1 An organic compound of one embodiment of the present invention represented by the general formula (G1) having a fluorene skeleton represented by and a dibenzofuran skeleton or a dibenzothiophene skeleton.

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

[0152] [Chemical formula 37]

[0153] In the synthesis scheme (a-5-1), Q 3 represents chlorine, bromine, iodine, or trifluoromethanesulfonate. 1 To R 22 , X, and n are the same as the organic compound represented by the general formula (G1). In addition, similarly to the synthesis schemes (a-1) and (a-2), the Buchwald-Hartwig reaction using a palladium catalyst can be performed in the above synthesis scheme (a-5-1).

[0154] In the synthesis scheme (a-5-1), an amine compound (compound 16) having a binaphthyl skeleton and a dibenzofuranylamine skeleton or a dibenzothiophene skeleton can be obtained by cross-coupling a compound having a dibenzofuran skeleton or a dibenzothiophene skeleton (compound 6) with an amine compound having a binaphthyl skeleton (compound 10).

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

[0156] [Chemical formula 38]

[0157] [Chemical formula 39]

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

[0159] First, as in the above-mentioned synthesis scheme (a-5-2), by cross-coupling an amine compound having a dibenzofuran skeleton or a dibenzothiophene skeleton (compound 2) with a boron compound having a phenyl group (compound 13), a dibenzofuranyl or dibenzothiophene amine compound (compound 17) having a phenyl group bonded to boron can be obtained.

[0160] Next, as in the above-mentioned synthesis scheme (a-5-3), by cross-coupling compound 17 with a boron compound having a binaphthyl skeleton (compound 15), an amine compound (compound 16) having a binaphthyl skeleton and a dibenzofuranylamine skeleton or a dibenzothiophene skeleton can be obtained.

[0161] In the above synthesis scheme (a-5-2), a Buchwald-Hartwig reaction using a palladium catalyst can be performed, as in the synthesis scheme (a-1) and (a-2). In addition, in the above synthesis scheme (a-5-3), a Suzuki-Miyaura reaction using a palladium catalyst can be performed, 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] [Chemical formula 40]

[0164] In the synthesis scheme (a-5-2-1), Q 3 represents chlorine, bromine, iodine, or trifluoromethanesulfonate.1 To R 11 Each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms, R 1 To R 11 They may also be bonded to each other to form a ring, and examples of the boron compound in this case include borane. 1 To R 11 , X is the same as the organic compound represented by the general formula (G1). In addition, similarly to the synthesis schemes (a-1) and (a-2), the Buchwald-Hartwig reaction using a palladium catalyst can be performed in the above synthesis scheme (a-5-2-1).

[0165] In the synthesis scheme (a-5-2-1), a dibenzofuran or dibenzothiophene amine compound (compound 17) having a phenyl group bonded to boron 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] As the organic compound represented by the general formula (G1), the organic compound having Ar 1 The dibenzofuranylamine or dibenzothienylamine compound having a fluorene skeleton (Compound 3) can be synthesized by the following synthesis schemes (a-7) and (a-8).

[0167] [Chemical formula 41]

[0168] [Chemical formula 42]

[0169] In the synthesis schemes (a-7) and (a-8), Q 8 and Q 9 Each independently represents chlorine, bromine, iodine, or triflate. 1 To R 22 Each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms, R 1 To R 22 They may also be bonded to each other to form a ring, and examples of the boron compound in this case include borane. 1 To R 22 , X, n, Ar 1 The same as the organic compound represented by the general formula (G1).

[0170] First, as in the above-mentioned synthesis scheme (a-7), by making a1 The dibenzofuranylamine or dibenzothiopheneylamine compound (Compound 3) having a fluorene skeleton represented by the cross coupling with the benzene compound (Compound 18) can obtain a dibenzofuranylamine or dibenzothiophene skeleton and Ar 1 The amine compound having a fluorene skeleton is represented (Compound 19).

[0171] Next, by cross-coupling compound 19 with a boron compound having a binaphthyl skeleton (compound 9) according to the above synthesis scheme (a-8), a compound having a binaphthyl skeleton and composed of Ar 1 An organic compound of one embodiment of the present invention represented by the general formula (G1) having a fluorene skeleton represented by and a dibenzofuran skeleton or a dibenzothiophene skeleton.

[0172] In addition, similarly to the synthesis schemes (a-1) and (a-2), the Buchwald-Hartwig reaction using a palladium catalyst can be performed in the above synthesis scheme (a-7). In addition, similarly to the synthesis scheme (a-3-1), the Suzuki-Miyaura reaction using a palladium catalyst can be utilized in the above synthesis scheme (a-8).

[0173] As the organic compound represented by the general formula (G1), the organic compound having Ar 1 The dibenzofuranylamine or dibenzothienylamine compound having a fluorene skeleton (Compound 3) can be synthesized according to the following synthesis schemes (a-9) and (a-10).

[0174] [Chemical formula 43]

[0175] [Chemical formula 44]

[0176] In the synthesis schemes (a-9) and (a-10), Q 6 and Q 7 Each independently represents chlorine, bromine, iodine, or triflate. 1 To R 22 Each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms, R 1 To R 22 They may also be bonded to each other to form a ring, and examples of the boron compound in this case include borane. 1 To R 22 , X, n, Ar 1 The same as the organic compound represented by the general formula (G1).

[0177] First, as in the above-mentioned synthesis scheme (a-9), by making a 1 The dibenzofuranylamine or dibenzothienylamine compound having a fluorene skeleton represented by (Compound 3) is cross-coupled with a boron compound having a phenyl group (Compound 13) to obtain a dibenzofuranylamine or dibenzothienylamine compound having a phenyl group bonded to boron (Compound 20).

[0178] Next, by cross-coupling compound 20 with a boron compound having a binaphthyl skeleton (compound 15) according to the above synthesis scheme (a-10), a compound having a binaphthyl skeleton and composed of Ar 1 An organic compound of one embodiment of the present invention represented by the general formula (G1) having a fluorene skeleton represented by and a dibenzofuran skeleton or a dibenzothiophene skeleton.

[0179] In addition, similarly to the synthesis schemes (a-1) and (a-2), the Buchwald-Hartwig reaction using a palladium catalyst can be performed in the above synthesis scheme (a-9). In addition, similarly to the synthesis scheme (a-3-1), the Suzuki-Miyaura reaction using a palladium catalyst can be performed in the above synthesis scheme (a-10).

[0180] As described above, the organic compound of one embodiment of the present invention represented by the general formula (G1) can be obtained.

[0181] Specifically, an organic compound that can be used as a secondary amine is shown as compound 3 in the above synthesis scheme.

[0182] [Chemical formula 45]

[0183] [Chemical formula 46]

[0184] [Chemical formula 47]

[0185] [Chemical formula 48]

[0186] [Chemical formula 49]

[0187] [Chemical formula 50]

[0188] [Chemical formula 51]

[0189] [Chemical formula 52]

[0190] Furthermore, the organic compound that can be used as the secondary amine shown as compound 7 in the above synthesis scheme is specifically shown.

[0191] [Chemical formula 53]

[0192] [Chemical formula 54]

[0193] [Chemical formula 55]

[0194] [Chemical formula 56]

[0195] [Chemical formula 57]

[0196] In addition, the organic compound that can be used as the secondary amine shown as compound 16 in the above synthesis scheme is specifically shown.

[0197] [Chemical formula 58]

[0198] [Chemical formula 59]

[0199] [Chemical formula 60]

[0200] [Chemical formula 61]

[0201] In addition, specific examples of the organic compound of one embodiment of the present invention described in this embodiment include organic compounds represented by structural formula (100) to structural formula (247) and structural formula (300) to structural formula (447).

[0202] [Chemical formula 62]

[0203] [Chemical formula 63]

[0204] [Chemical formula 64]

[0205] [Chemical formula 65]

[0206] [Chemical formula 66]

[0207] [Chemical formula 67]

[0208] [Chemical formula 68]

[0209] [Chemical formula 69]

[0210] [Chemical formula 70]

[0211] [Chemical formula 71]

[0212] [Chemical formula 72]

[0213] [Chemical formula 73]

[0214] [Chemical formula 74]

[0215] [Chemical formula 75]

[0216] [Chemical formula 76]

[0217] [Chemical formula 77]

[0218] [Chemical formula 78]

[0219] [Chemical formula 79]

[0220] [Chemical formula 80]

[0221] [Chemical formula 81]

[0222] [Chemical formula 82]

[0223] [Chemical formula 83]

[0224] [Chemical formula 84]

[0225] [Chemical formula 85]

[0226] [Chemical formula 86]

[0227] [Chemical formula 87]

[0228] [Chemical formula 88]

[0229] [Chemical formula 89]

[0230] [Chemical formula 90]

[0231] [Chemical formula 91]

[0232] [Chemical formula 92]

[0233] [Chemical formula 93]

[0234] [Chemical formula 94]

[0235] [Chemical formula 95]

[0236] [Chemical formula 96]

[0237] [Chemical formula 97]

[0238] [Chemical formula 98]

[0239] [Chemical formula 99]

[0240] [Chemical formula 100]

[0241] [Chemical Formula 101]

[0242] [Chemical formula 102]

[0243] [Chemical formula 103]

[0244] [Chemical formula 104]

[0245] [Chemical formula 105]

[0246] Implementation Method 2 In this embodiment, an organic semiconductor device which is one embodiment of the present invention is described in detail.

[0247] Figures 1A to 1C Schematic diagram of a light-emitting device of one embodiment of the present invention. The first electrode 101 of the light-emitting device is provided on an insulator 100, and an organic compound layer 103 is included between the first electrode 101 and the second electrode 102. The organic compound layer 103 contains at least one of the organic compounds represented by general formula (G1) to general formula (G6) in Embodiment 1. In addition, the organic semiconductor device of 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 photoelectric sensor, etc.). The light-emitting layer 113 in the light-emitting device contains a light-emitting center substance, and the light-emitting center substance emits light by applying a voltage between the first electrode 101 and the second electrode 102.

[0248] Preferably, if Figure 1A As shown, the organic compound layer 103 includes 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 in addition to the light-emitting layer 113. Note that the organic compound layer 103 may 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 generation layer. Conversely, any of the above-mentioned layers may not be provided.

[0249] In Embodiment 1, the organic compound represented by General Formula (G1) to General Formula (G6) is preferably included in a hole transport layer. Examples of the hole transport layer include a hole injection layer, a hole transport layer, an electron blocking layer, and a light emitting layer.

[0250] In this embodiment, the first electrode 101 is recorded as an electrode including an anode and the second electrode 102 is recorded as an electrode including a cathode, but the reverse may be true. The first electrode 101 and the second electrode 102 are formed in a single-layer structure or a stacked-layer structure. When the stacked-layer structure is used, the layer in contact with the organic compound layer 103 is used as the anode or the cathode. When the electrode has a stacked-layer structure, there is no restriction on the work function of the layer other than the layer in contact with the organic compound layer 103, and the material can be selected according to the required characteristics such as resistance value, processing convenience, reflectivity, 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). Specifically, examples include indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide (ITSO: Indium Tin Silicon Oxide), indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide (IWZO), and the like. Although these conductive metal oxide films are usually formed by sputtering, they can also be formed by a sol-gel method. As an example of a formation method, a method of forming indium oxide-zinc oxide by sputtering using a target material having 1 wt% to 20 wt% of zinc oxide added to indium oxide can be cited. In addition, indium oxide (IWZO) containing tungsten oxide and zinc oxide can be formed by sputtering using a target material having 0.5 wt% to 5 wt% of tungsten oxide and 0.1 wt% to 1 wt% of zinc oxide added to indium oxide. In addition, as materials for the anode, 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) can be cited. In addition, the anode can also be a layer in which the above materials are stacked. For example, a film of Al, Ti, and ITSO stacked in sequence on Ti has high efficiency due to good reflectivity and can achieve a high resolution of thousands of ppi, so it is preferred. In addition, graphene can also be used as a material for the anode. In addition, by using a composite material that can constitute the hole injection layer 111 described later for a layer in contact with the anode (typically a hole injection layer), it is possible to select an electrode material without taking into account the work function.

[0252] The hole injection layer 111 is in contact with the anode and has the function of facilitating hole injection into the organic compound layer 103. Phthalocyanine compounds and phthalocyanine complex compounds such as phthalocyanine (abbreviated as H) can be used. 2 Pc), copper phthalocyanine (CuPc), etc.; aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as: DNTPD), etc.; or polymer compounds such as poly(3,4-ethylenedioxythiophene) / (polystyrene sulfonic acid) (abbreviated as: PEDOT / PSS), etc. to form the hole injection layer 111.

[0253] In addition, the hole injection layer 111 may be composed of a substance having electron acceptor properties. As the substance having electron acceptor properties, an organic compound having an electron withdrawing group (halogen group, cyano group, etc.) may be used, and examples thereof include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), and 2-(7-dicyanomethylidene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile. In particular, compounds such as HAT-CN in which an electron-withdrawing group is bonded to a fused aromatic ring having multiple heteroatoms are thermally stable and therefore are preferred. In addition, [3] axial ene derivatives containing electron-withdrawing groups (especially halogen groups such as fluorine groups, cyano groups, etc.) are particularly preferred because they have very high electron acceptor properties. Specifically, examples include: α, α', α"-1,2,3-cyclopropane trimethylene tris[4-cyano-2,3,5,6-tetrafluorophenylacetonitrile], α, α', α"-1,2,3-cyclopropane trimethylene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenylacetonitrile], α, α', α"-1,2,3-cyclopropane trimethylene tris[2,3,4,5,6-pentafluorophenylacetonitrile], etc. As a substance having acceptor properties, in addition to the above-mentioned organic compounds, transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide can be used.

[0254] In addition, the hole injection layer 111 is preferably formed of a composite material including the above-mentioned material having an acceptor property and an organic compound having a hole transport property.

[0255] As the organic compound with hole transport property used in the composite material, various organic compounds such as aromatic amine compounds, heteroaromatic compounds, aromatic hydrocarbons, high molecular weight compounds (oligomers, dendrimers, polymers, etc.) can be used. As the organic compound with hole transport property used in the composite material, it is preferred to use an organic compound with a hole mobility of 1×10 -6 cm 2 / Vs or more organic compounds. The organic compound with hole transport properties used in the composite material is preferably a compound containing a fused aromatic hydrocarbon ring or a π-electron-rich heteroaromatic ring. As the fused aromatic hydrocarbon ring, an anthracene ring, a naphthalene ring, etc. are preferred. In addition, as the π-electron-rich heteroaromatic ring, a fused aromatic ring containing at least one of a pyrrole skeleton, a furan skeleton and a thiophene skeleton is preferred, and specifically a carbazole ring, a dibenzothiophene ring or a ring in which these rings are also fused with an aromatic ring or a heteroaromatic ring is preferred.

[0256] Such an organic compound having hole transport properties preferably has any one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton and an anthracene skeleton. In particular, it can be an aromatic amine having a substituent including a dibenzofuran ring or a dibenzothiophene ring, an aromatic monoamine including a naphthalene ring, or an aromatic monoamine in which a 9-fluorenyl group is bonded to the nitrogen of the amine through an arylene group. Note that when these organic compounds having hole transport properties are substances including N, N-bis(4-biphenyl)amino groups, a light-emitting device with a long life can be manufactured, so it is preferred.

[0257] Specific examples of the organic compound having a hole transport property include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4"-phenyltriphenylamine (abbreviated as BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviated as BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1 ,2-d]furan-8-amine (abbreviated as BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviated as BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviated as DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl-4-benzidine (abbreviated as ThBA1BP), 4-(2-naphthyl)-4',4"-diphenyltriphenylamine (abbreviated as BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4"-diphenyltriphenylamine (abbreviated as BBAβNBi), 4,4'-diphenyl Phenyl-4"-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBAαNβNB), 4,4'-diphenyl-4"-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBAαNβNB-03), 4,4'-diphenyl-4"-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviated as: BBAPβNB-03), 4,4'-diphenyl-4"-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBA(βN2)B), 4,4'-diphenyl-4"-(7;2'-binaphthyl-2-yl)-triphenylamine (abbreviated as: BBA(βN2)B-03), 4,4'-diphenyl-4"-(4;2'-binaphthyl- 1-yl) triphenylamine (abbreviated as: BBAβNαNB), 4,4'-diphenyl-4"-(5;2'-binaphthyl-1-yl) triphenylamine (abbreviated as: BBAβNαNB-02), 4-(4-biphenyl)-4'-(2-naphthyl)-4"-phenyltriphenylamine (abbreviated as: TPBiAβNB), 4-(3-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4"-phenyltriphenylamine (abbreviated as: mTPBiAβNBi), 4-(4-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4"-phenyltriphenylamine (abbreviated as: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviated as: 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)phenyl]tri(biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4"-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNB SF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviated as: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviated as: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviated as: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzofuran-4-amine (abbreviated as: 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-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 9H-fluorene-2-amine (abbreviated as: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi[9H-fluorene-4-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi[9H-fluorene-4-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi-9H-fluorene-3-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi-9H-fluorene-2-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi-9H-fluorene-1-amine, etc.

[0258] In addition, as a material having a hole transport property, as other aromatic amine compounds, N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviated as DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B), etc. can also be used. In addition, the organic compounds represented by general formula (G1) to general formula (G6) in embodiment 1 can also be appropriately used.

[0259] By forming the hole injection layer 111, hole injection properties can be improved, so that a light-emitting device with a low driving voltage can be obtained.

[0260] Furthermore, among substances having acceptor properties, organic compounds having acceptor properties can be easily formed by vapor deposition and are therefore easy-to-use materials.

[0261] The hole transport layer 112 is formed of an organic compound having a hole transport property. The organic compound having a hole transport property preferably has a 1×10 -6 cm 2 / Vs and above hole mobility.

[0262] Examples of the hole-transporting material include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviated as TPD), N,N'-bis(9,9'-spirobi[9H-fluorene]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as mBPAFLP), and 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBA1BP). , 4,4'-diphenyl-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluorene-2-amine (abbreviated as PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviated as PCBASF), etc.;1,3-Bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-bis(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviated as BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviated as BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H -3,3'-bicarbazole (abbreviated as: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviated as: βNCCP), 9-(3-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviated as: βNCCmBP), 9-(4-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviated as: βNCCBP), 9,9'-di-2-naphthyl-3,3'-9H,9'H-bicarbazole (abbreviated as: 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':3',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 Compounds having a carbazole skeleton such as oxazole, 9-(2-naphthyl)-9'-(triphenyl-2-yl)-3,3'-9H,9'H-bicarbazole, 9-phenyl-9'-(triphenyl-2-yl)-3,3'-9H,9'H-bicarbazole (abbreviated as PCCzTp), 9,9'-bis(triphenyl-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(4-biphenyl)-9'-(triphenyl-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(triphenyl-2-yl)-9'-[1,1':3',1"-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole;Compounds having a thiophene skeleton, such as 4,4',4"-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluorene-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-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among them, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferred because they have high reliability and excellent hole transport properties and contribute to lowering the driving voltage. Note that as the material constituting the hole transport layer 112, the substances listed as the materials having hole transport properties as the composite materials for the hole injection layer 111 can also be appropriately used. In addition, the organic compounds represented by the general formula (G1) to the general formula (G6) in Embodiment 1 can also be appropriately used. ;

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

[0264] In the light-emitting layer, materials that can be used as the fluorescent substance include, for example, the following substances. Note that other fluorescent substances can also be used.

[0265] Examples thereof include 5,6-bis[4-(10-phenyl-9-anthracenyl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthracenyl)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-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviated as: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2- triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert-butyl perylene (abbreviation: TBP), 4-(10-phenyl-9-anthracenyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), N,N"-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene )bis(, N', N'-triphenyl-1,4-phenylenediamine) (abbreviated as: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviated as: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 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-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9 , 10-bis(biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated as: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as: DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviated as: DPQd), rubrene, 5,12-bis(biphenyl-4-yl)-6,11-diphenylnaphthacene (abbreviated as: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]vinyl}-6-methyl-4H-pyran-4-ylidene)malononitrile (abbreviated as: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-9- 1,2-diaminobenzene (abbreviated as: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)naphthocene-5,11-diamine (abbreviated as: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated as: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl -2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]vinyl}-4H-pyran-4-ylidene)malononitrile (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)vinyl]-4H-pyran-4-ylidene}malononitrile (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-carbazole-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 represented by pyrene diamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 are preferred because they have high hole-trapping properties, high luminous efficiency, and high reliability. ,

[0266] In addition, 5,9-diphenyl-5,9-diaza-13b-borazinahpatho[3,2,1-de]anthracene (abbreviation: DABNA1), 9-(diphenyl-3-yl)-N,N,5,11-tetraphenyl-5,9-dihydro-5,9-diaza-13b-borazinahpatho[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]benzazaboro[2,3,4-kl]phenazepine can be used as appropriate. Boron-7-amine (abbreviation: DPhA-tBu4DABNA), 2,12-di(tert-butyl)-N,N,5,9-tetrakis(4-tert-butylphenyl)-5H,9H-[1,4]benzoazaboro[2,3,4-kl]benzoazaboro-7-amine (abbreviation: tBuDPhA-tBu4DABNA), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-7-methyl-5H,9H-[1,4]benzoazaboro[2,3,4-kl]phenazineboro (abbreviation: Me-tBu4DABNA), N 7 , N 7 , N 13 , N13,5,9,11,15-octaphenyl-5H,9H,11H,15H-[1,4]benzazaboro[2,3,4-kl][1,4]benzazaboro[4',3',2':4,5][1,4]benzazaboro[3,2-b]phenazaboro-7,13-diamine (abbreviation: ν-DABNA), 2-(4-tert-butylphenyl)benzo[5,6]indole[3,2,1-jk]benzo[b]carbazole (abbreviation: tBuPBibc) and other condensed heteroaromatic compounds containing nitrogen and boron, especially compounds having a diaza-borazine-naphtho-anthracene skeleton, have a narrow emission spectrum and can obtain blue light emission with good color purity, so they can be appropriately used.

[0267] In addition to the above, 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazole-9-yl]-2,5,15,18-tetra(1,1-dimethylethyl)indol[3,2,1-de]indol[3',2',1':8,1][1,4]benzazaboro[2,3,4-kl]phenazoneboro (abbreviation: BBCz-G), 9,11-bis[3,6-bis(1,1-dimethylethyl)-9H-carbazole-9-yl]-2,5,15,18-tetra(1,1-dimethylethyl)indol[3,2,1-de]indol[3',2',1':8,1][1,4]benzazaboro[2,3,4-kl]phenazoneboro (abbreviation: BBCz-Y), etc. can also be appropriately 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] Examples include tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviated as [Ir(mpptz-dmp) 3 ]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazole)iridium(III) (abbreviated as: [Ir(Mptz) 3 ]) and other organic metal iridium complexes with a 4H-triazole skeleton; tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole]iridium(III) (abbreviated as: [Ir(Mptz1-mp) 3 ]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazole)iridium(III) (abbreviated as: [Ir(Prptz1-Me) 3 ]) and other organometallic iridium complexes with a 1H-triazole skeleton; fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviated as: [Ir(iPrpim) 3 ), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviated as: [Ir(dmpimpt-Me) 3]), tris(2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazol-2-yl-κN3}-4-cyanophenyl-κC)iridium(III) (abbreviated as CNImIr), etc.; tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC2)phenyl-κC]iridium(III) (abbreviated as [Ir(cb) 3 ]) and other organic metal complexes having a benzimidazole skeleton; and bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2 '] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviated as FIr6), bis [2-(4', 6'-difluorophenyl) pyridinium-N, C 2 '] iridium (III) picolinate (abbreviated as FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinium-N,C 2 '}Iridium(III) picolinate (abbreviated as: [Ir(CF 3 ppy) 2 (pic)]), bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2 '] Iridium (III) acetylacetonate (abbreviated as FIracac) and other organic metal iridium complexes with phenylpyridine derivatives having electron withdrawing groups as ligands. The above substances are compounds that emit blue phosphorescence and have a luminescence peak in the wavelength region of 450nm to 520nm.

[0270] In addition, tris(4-methyl-6-phenylpyrimidinyl)iridium(III) (abbreviated as [Ir(mppm) 3 ]), tri(4-tert-butyl-6-phenylpyrimidinyl)iridium(III) (abbreviated as: [Ir(tBuppm) 3 ]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviated as: [Ir(mppm) 2 (acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviated as [Ir(tBuppm) 2 (acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviated as: [Ir(nbppm) 2 (acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviated as: [Ir(mpmppm) 2 (acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviated as: [Ir(dppm)2 (acac)]) and other organic metal iridium complexes with pyrimidine skeletons; (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazine)iridium(III) (abbreviated as: [Ir(mppr-Me) 2 (acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazine)iridium(III) (abbreviated as: [Ir(mppr-iPr) 2 (acac)]) and other organic metal iridium complexes with pyrazine skeletons; tris(2-phenylpyridinium-N,C 2’ )Iridium(III) (abbreviation: [Ir(ppy) 3 ]), bis(2-phenylpyridinium-N,C 2’ )iridium(III) acetylacetonate (abbreviated as: [Ir(ppy) 2 (acac)]), bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as: [Ir(bzq) 2 (acac)]), tris(benzo[h]quinoline)iridium(III) (abbreviated as: [Ir(bzq) 3 ]), tris(2-phenylquinoline-N,C 2’ )iridium(III) (abbreviation: [Ir(pq) 3 ]), bis(2-phenylquinoline-N,C 2’ )iridium(III) acetylacetonate (abbreviated as: [Ir(pq) 2 (acac)]), [2-d3-methyl-8-(2-pyridyl-κN)benzofurano[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridyl-κN 2 )phenyl-κC]iridium(III) (abbreviated as: [Ir(5mppy-d3) 2 (mbfpypy-d3)]), [2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofurano[2,3-b]pyridin-7-yl-κC]bis[5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC]iridium(III) (abbreviated as: [Ir(5mtpy-d6) 2 (mbfpypy-iPr-d4)]), [2-d3-methyl-(2-pyridyl-κN)benzofurano[2,3-b]pyridine-κC]bis[2-(2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviated as: [Ir(ppy) 2(mbfpypy-d3)]), [2-(4-methyl-5-phenyl-2-pyridyl-κN)phenyl-κC]bis[2-(2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviated as: [Ir(ppy) 2 (mdppy)]), [2-(4-d3-methyl-5-phenyl-2-pyridyl-κN2)phenyl-κC]bis[2-(5-d3-methyl-2-pyridyl-κN2)phenyl-κC]iridium(III) (abbreviated as: [Ir(5mppy-d3) 2 (mdppy-d3)]), [2-methyl-(2-pyridyl-κN)benzofurano[2,3-b]pyridine-κC]bis[2-(2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviated as: [Ir(ppy) 2 (mbfpypy)]) and other organometallic iridium complexes with a pyridine skeleton; and tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviated as: [Tb(acac) 3 (Phen)]) and other rare earth metal complexes. The above substances are mainly compounds that exhibit green phosphorescence and have a luminescence peak in the wavelength region of 500nm to 600nm. In addition, since organic metal iridium complexes having a pyrimidine skeleton have particularly excellent reliability or luminous efficiency, they are particularly preferred.

[0271] In addition, (diisobutyrylmethane)bis[4,6-bis(3-methylphenyl)pyrimidinyl]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinyl](dipivaloylmethanyl)iridium(III) (abbreviated as: [Ir(5mdppm) 2 (dpm)]), bis[4,6-di(naphthalene-1-yl)pyrimidinyl](dipivaloylmethano)iridium(III) (abbreviated as: [Ir(d1npm) 2 (dpm)]) and other organometallic iridium complexes with a pyrimidine skeleton; (acetylacetonato)bis(2,3,5-triphenylpyrazine)iridium(III) (abbreviated as: [Ir(tppr) 2 (acac)]), bis(2,3,5-triphenylpyrazine)(dipivaloylmethano)iridium(III) (abbreviated as [Ir(tppr) 2 (dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as: [Ir(Fdpq) 2 (acac)]) and other organic metal iridium complexes with pyrazine skeletons; tris(1-phenylisoquinoline-N,C 2’ )iridium(III) (abbreviation: [Ir(piq)3 ]), bis(1-phenylisoquinoline-N,C 2’ )iridium(III) acetylacetonate (abbreviated as: [Ir(piq) 2 Organometallic iridium complexes having a pyridine skeleton, such as (acac)], (3,7-diethyl-4,6-nonanedione-κO4,κO6)bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolyl-κN]phenyl-κC]iridium(III), (3,7-diethyl-4,6-nonanedione-κO4,κO6)bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolyl-κN]phenyl-κC]iridium(III); platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP); and tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviated as [Eu(DBM) 3 (Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetone](monophenanthroline)europium(III) (abbreviated as: [Eu(TTA) 3 (Phen)]) and other rare earth metal complexes. The above substances are compounds that exhibit red phosphorescence and have a luminescence peak in the wavelength region of 600nm to 700nm. In addition, organic metal iridium complexes having a pyrazine skeleton can obtain red luminescence with good chromaticity.

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

[0273] As TADF materials, fullerene and its derivatives, acridine and its derivatives, and eosin derivatives can be used. In addition, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can also be cited. As the metal-containing porphyrin, for example, a protoporphyrin-tin fluoride complex (SnF 2 (Proto IX)), mesoporphyrin-tin fluoride complex (SnF 2 (Meso IX)), hematoporphyrin-tin fluoride complex (SnF 2 (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF 2 (Copro III-4Me), octaethylporphyrin-tin fluoride complex (SnF 2 (OEP)), protoporphyrin-tin fluoride complex (SnF 2 (Etio I)) and octaethylporphyrin-platinum chloride complex (PtCl2 OEP) etc.

[0274] [Chemical formula 106]

[0275] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindol[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), and 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) represented by the following structural formula can also be used. Heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, such as 3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-oxanthene-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridinium)phenyl]sulfone (abbreviation: DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracenes]-10'-one (abbreviation: ACRSA). Such heterocyclic compounds having a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring have high electron transport properties and hole transport properties, and are therefore preferred. Among them, in the skeleton with a π-electron-deficient heteroaromatic ring, the pyridine skeleton, the diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton) and the triazine skeleton are stable and have good reliability, so they are preferred. In particular, the benzofuranopyrimidine skeleton, the benzothiophenopyrimidine skeleton, the benzofuranopyrazine skeleton, and the benzothiophenopyrazine skeleton have high acceptor properties and good reliability, so they are preferred. In addition, in the skeleton with 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 stable and have good reliability, so it is preferred to have at least one of the above skeletons. In addition, as a furan skeleton, a dibenzofuran skeleton is preferably used, and as a thiophene skeleton, a dibenzothiophene skeleton is preferably used. As a pyrrole skeleton, an indole skeleton, a carbazole skeleton, an indolecarbazole skeleton, a bicarbazole skeleton, and a 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole skeleton are particularly preferably used. In the case of a substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded, 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 high, while S 1Energy Level and T 1 The energy difference between the energy levels becomes smaller, and thermally activated delayed fluorescence can be efficiently obtained, so it is particularly preferred. Note that an aromatic ring bonded with an electron-withdrawing group such as a cyano group can also be used instead of a π-electron-deficient heteroaromatic ring. In addition, as a π-electron-rich skeleton, an aromatic amine skeleton, a phenazine skeleton, etc. can be used. In addition, as a π-electron-deficient skeleton, a xanthene skeleton, a thioxanthene dioxide skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or boranthrene, an aromatic ring or heteroaromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, etc. can be used. In this way, a π-electron-deficient heteroaromatic ring and a π-electron-rich heteroaromatic ring can be replaced with a π-electron-deficient skeleton and a π-electron-rich skeleton.

[0276] [Chemical formula 107]

[0277] TADF material refers to S 1 Energy Level and T 1 A material having a small difference in energy levels and having the function of converting triplet excitation energy into singlet excitation energy by anti-intersystem crossing. Therefore, the triplet excitation energy can be up-converted into singlet excitation energy (anti-intersystem crossing) by a small amount of thermal energy and a singlet excited state can be efficiently generated. In addition, the triplet excitation energy can be converted into luminescence.

[0278] The two substances form an excited state exciplex (Exciplex) due to S 1 Energy Level and T 1 The difference in energy levels is extremely small, and it has the function of a TADF material that can convert triplet excitation energy into singlet excitation energy.

[0279] Note that as T 1 As an indicator of the energy level, the phosphorescence spectrum observed at low temperature (e.g., 77K to 10K) can be used. Regarding the TADF material, it is preferred that when the wavelength energy of the extrapolated line obtained by drawing a tangent line at the tail of the short wavelength side of the fluorescence spectrum is S 1 The energy level is calculated by taking the wavelength energy of the extrapolated line obtained by drawing a tangent line at the tail of the short wavelength side of the phosphorescence spectrum as T. 1 When the energy level is S 1 With T 1 The difference is 0.3 eV or less, and more preferably 0.2 eV or less.

[0280] In addition, when using TADF materials as light-emitting substances, the S 1 The energy level is preferred over the S of TADF materials 1In addition, the T 1 The energy level is preferred over the T of TADF materials. 1 High energy level.

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

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

[0283] Such an organic compound having hole transport properties preferably has any one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton and an anthracene skeleton. In particular, it can be an aromatic amine having a substituent including a dibenzofuran ring or a dibenzothiophene ring, an aromatic monoamine including a naphthalene ring, or an aromatic monoamine in which a 9-fluorenyl group is bonded to the nitrogen of the amine through an arylene group. Note that when these organic compounds having hole transport properties are substances including N, N-bis(4-biphenyl)amino groups, a light-emitting device with a long life can be manufactured, so it is preferred.

[0284] Examples of such organic compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviated as TPD), N,N'-bis(9,9'-spirobi[9H-fluorene]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4 ... -(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N- Compounds having an aromatic amine skeleton, such as phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviated as PCBASF); compounds having a carbazole skeleton, such as 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-bis(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as PCCP); 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as DBT3 P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviated as: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as: DBTFLP-IV) and other compounds having a thiophene skeleton; and 4,4',4"-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviated as: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as: mmDBFFLBi-II) and other compounds having a furan skeleton. Among them, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton have good reliability and high hole transport properties and help to reduce the driving voltage, so they are preferred. In addition, organic compounds listed as examples of materials having hole transport properties as a hole transport layer can also be used.In addition, the organic compounds represented by General Formula (G1) to General Formula (G6) in Embodiment 1 can also be used as appropriate.

[0285] As a material having electron transport properties, it is preferable to use a material having an electron mobility of 1×10 -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2 In addition, any substance other than the above may be used as long as it has a higher electron-transporting property than a hole-transporting property.

[0286] As a material having electron transport properties, for example, bis(10-hydroxybenzo[h]quinolinolato)beryllium(II) (abbreviated as BeBq 2 ), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ), and other metal complexes, and organic compounds containing a π-electron-deficient heteroaromatic ring. Examples of organic compounds containing a π-electron-deficient heteroaromatic 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 heteroaromatic rings having a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), organic compounds containing heteroaromatic rings having a pyridine skeleton, or organic compounds containing heteroaromatic rings having a triazine skeleton have good reliability, so they are preferred. 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, which helps to reduce the driving voltage. In addition, benzofuranopyrimidine skeletons, benzothiophenopyrimidine skeletons, benzofuranopyrazine skeletons, and benzothiophenopyrazine skeletons have high acceptor properties and high reliability, so they are preferred.

[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-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3- organic compounds having an azole skeleton, such as 1-phenyl-1H-benzimidazole (mDBTBIm-II), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (BzOs); 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (35DCzPPy), 1,3,5-tris[3-(3-pyridyl)phenyl]benzene (TmPyPB), bathophenanthroline (Bphen), bathocuproin (BCP), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,2'-(1,3-phenylene)bis(9-phenylene)pyridine (35DCzPPy), 1,3,5-tris[3-(3-pyridyl)phenyl]benzene (TmPyPB), bathophenanthroline (Bphen), bathocuproin (BCP), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), -1,10-phenanthroline) (abbreviation: mPPhen2P), 2-[3-(2-triphenylene)phenyl]-1,10-phenanthroline (abbreviation: mTpPPhen), 2-phenyl-9-(2-triphenylene)-1,10-phenanthroline (abbreviation: Ph-TpPhen), 2-[4-(9-phenanthrenyl)-1-naphthyl]-1,10-phenanthroline (abbreviation: PnNPhen), 2-[4-(2-triphenylene)phenyl]-1,10-phenanthroline (abbreviation: pTpPPhen); 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-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazole-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 2-[4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), 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: 9mDBtBPNfpr), 9-[3'-(dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn P2Pm), 4,6-bis[3-(dibenzothiophene-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 9,9'-[pyrimidine-4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 8-(biphenyl-4-yl)-4-[3-(dibenzothiophene-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviation: 8BP-4mDBtPBfpm), 3,8-bis[3-(dibenzothiophene-4-yl)phenyl] ]benzofurano[2,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)(1,1'-biphenyl-3-yl)]naphtho[1',2':4,5]furano[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), 8-[(2,2'-binaphthyl)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviation: 8(βN2)-4m DBtPBfpm), 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-naphthyl-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidineorganic compounds having a diazine skeleton, such as 5-bis(9H-carbazole-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 7-[4-(9-phenyl-9H-carbazole-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz); 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluorene]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPT zn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviated as mBnfBPTzn-02), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviated as PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviated as 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-triazine-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (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-diphenyl-1,3,5 -triazine (abbreviation: mPn-mDMePyPTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine-2-yl]-11,12-dihydro-12-phenyl-indolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), 2-[3'-(triphenylene-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 3-[9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-(biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',An organic compound containing a heteroaromatic ring having a triazine skeleton, such as [1-(1-(1-terphenyl)-4-yl)-1-dibenzofuranyl]-1,3,5-triazine (abbreviation: mBP-TPDBfTzn). In addition, an organic compound containing a heteroaromatic ring having a diazine skeleton, an organic compound containing a heteroaromatic ring having a pyridine skeleton, or an organic compound containing a heteroaromatic ring having a triazine skeleton has high reliability and is therefore preferred. In particular, an organic compound containing a heteroaromatic ring having a diazine (pyrimidine or pyrazine) skeleton and an organic compound containing a heteroaromatic ring having a triazine skeleton have high electron transport properties, which contribute to reducing the driving voltage.

[0289] As a TADF material that can be used as a host material, the same material as the material cited above as a TADF material can be used. When a TADF material is used as a host material, the triplet excitation energy generated by the TADF material is converted into singlet excitation energy through reverse intersystem crossing and further energy is transferred to the luminescent material, thereby improving the luminous efficiency of the light-emitting device. At this time, the TADF material is used as an energy donor and the luminescent material is used as an energy acceptor.

[0290] This is particularly effective when the luminescent material is a fluorescent material. 1 The energy level is preferably higher than that of the fluorescent material S 1 In addition, the T 1 The energy level is preferably higher than that of the fluorescent material S 1 Therefore, the T 1 The energy level is preferably higher than the T 1 High energy level.

[0291] In addition, it is preferable to use a TADF material that emits light at a wavelength overlapping with the absorption band on the lowest energy side of the fluorescent material. This is preferable because the excitation energy is smoothly transferred from the TADF material to the fluorescent material, and light emission can be obtained efficiently.

[0292] In order to efficiently generate singlet excitation energy from triplet excitation energy by anti-intersystem crossing, carrier recombination is preferably generated in TADF material. In addition, it is preferred that the triplet excitation energy generated in TADF material is not transferred to the triplet excitation energy of fluorescent material. For this reason, the fluorescent material preferably has a protecting group around the luminophore (the skeleton that becomes the cause of luminescence) possessed by the fluorescent material. As the protecting group, it is preferably a substituent without a π bond, preferably a saturated hydrocarbon, specifically, an alkyl group having a carbon number of more than 3 and less than 10, a substituted or unsubstituted cycloalkyl group having a carbon number of more than 3 and less than 10, and a trialkylsilyl group having a carbon number of more than 3 and less than 10, more preferably having a plurality of protecting groups. The substituent without a π bond has almost no function of transmitting carriers, so it has almost no effect on carrier transmission or carrier recombination, and the luminophore of the TADF material and the fluorescent material can be kept away from each other. Here, the luminophore refers to the atomic group (skeleton) that becomes the cause of luminescence in the fluorescent material. The luminophore preferably has a π-bond skeleton, preferably contains an aromatic ring, and preferably has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of the 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, In particular, the naphthalene skeleton, the anthracene skeleton, the fluorene skeleton, the Fluorescent substances having a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, or a naphthobisbenzofuran skeleton are preferred because they have high fluorescence quantum yields.

[0293] In the case where a fluorescent luminescent substance is used as a luminescent substance, as a main material, it is preferred to use a material having a paraben skeleton, especially a material having an anthracene skeleton. By using a substance having an anthracene skeleton as a main material of a fluorescent luminescent substance, a light-emitting layer with high luminous efficiency and durability can be achieved. Among the substances having an anthracene skeleton used as a main material, substances having a diphenylanthracene skeleton, especially a 9,10-diphenylanthracene skeleton, are chemically stable, so they are preferred. In addition, in the case where the main material has a carbazole skeleton, the injection / transport properties of holes are improved, so it is preferred. In the case of a benzocarbazole skeleton having a benzene ring fused to a carbazole skeleton, its HOMO energy level is about 0.1eV higher than that of the main material having a carbazole skeleton, and holes are easily injected, so it is more preferred. In particular, in the case where the main material has a dibenzocarbazole skeleton, its HOMO energy level is about 0.1eV higher than that of the main material having a carbazole skeleton, not only are holes easily injected, but also hole transport properties and heat resistance are improved, so it is preferred. Therefore, a more preferred host material is one having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). Note that 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-anthracenyl)phenyl]-9H-carbazole (abbreviated as PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthracenyl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviated as 2mBnfPPA), 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]- biphenyl-4'-yl]-anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α, βADN), 2-(10-phenylanthracene-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracenyl)-benzo[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), and the like. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred because they exhibit very good properties.

[0295] In addition, the host material may also be a material mixed with multiple substances. When a mixed host material is used, it is preferred to mix a material having an electron transport property and a material having a hole transport property. By mixing a material having an electron transport property and a material having a hole transport property, it is easier to adjust the transport property of the light-emitting layer 113, and it is also easier to control the recombination area. The weight ratio of the content of the material having a hole transport property and the material having an electron transport property may be 1:19 to 19:1.

[0296] Note that as part of the above mixed material, a phosphorescent substance may be used. When a fluorescent substance is used as a light-emitting substance, the phosphorescent substance may be used as an energy donor for supplying excitation energy to the fluorescent substance.

[0297] In addition, these mixed materials can also be used to form an exciplex. By selecting a mixed material in a manner to form an exciplex that emits light overlapping the wavelength of the absorption band on the lowest energy side of the luminescent substance, energy transfer can be smoothed, thereby efficiently obtaining luminescence, so it is preferred. In addition, by adopting this structure, the driving voltage can be reduced, so it is preferred.

[0298] Note that at least one of the materials forming the exciplex may be a phosphorescent substance. This allows efficient conversion of triplet excitation energy into singlet excitation energy via anti-intersystem crossing.

[0299] Regarding the combination of materials that efficiently form an exciplex, the HOMO energy level of the material having hole transport properties is preferably higher than the HOMO energy level of the material having electron transport properties. In addition, the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the material having hole transport properties is preferably higher than the LUMO energy level of the material having electron transport properties. Note that the LUMO energy level and HOMO energy level of the material can be obtained from the electrochemical properties (reduction potential and oxidation potential) of the material measured by cyclic voltammetry (CV) measurement.

[0300] Note that the formation of an exciplex can be confirmed, for example, by comparing the emission spectra of a material having hole transport properties, the emission spectra of a material having electron transport properties, and the emission spectra of a mixed film formed by mixing these materials. When the emission spectrum of the mixed film is observed to drift toward the long wavelength side compared to the emission spectrum of each material (or to have a new peak on the long wavelength side), it indicates that an exciplex has been formed. Alternatively, 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 formed by mixing these materials are compared. When the transient response is different, such as the ratio of the transient PL lifetime of the mixed film to the transient PL lifetime of each material is increased, it indicates that an exciplex has been formed. In addition, the above-mentioned transient PL can be referred to as transient electroluminescence (EL). In other words, the formation of an exciplex can 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 of 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. As the electron transport material, it is preferable to use a material having an electron mobility of 1×10 -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2 / Vs or more. In addition, as long as the electron transport property is higher than the hole transport property, substances other than the above may also be used. As the above-mentioned organic compound, it is preferred to use an organic compound containing a π-electron-deficient heteroaromatic ring. As an organic compound containing a π-electron-deficient heteroaromatic ring, for example, it is preferred to use any one or more of an organic compound containing a heteroaromatic ring having a polyazole skeleton, an organic compound containing a heteroaromatic ring having a pyridine skeleton, an organic compound containing a heteroaromatic ring having a diazine skeleton, and an organic compound containing a heteroaromatic ring having a triazine skeleton.

[0302] As an organic compound with electron transport properties that can be used for the above-mentioned electron transport layer 114, an organic compound that can be used as an organic compound with electron transport properties in the above-mentioned light-emitting layer 113 can also be used. Among them, organic compounds containing heteroaromatic rings with a diazine skeleton, organic compounds containing heteroaromatic rings with a pyridine skeleton, and organic compounds containing heteroaromatic rings with a triazine skeleton have good reliability, so they are preferred. In particular, organic compounds containing heteroaromatic rings with a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing heteroaromatic rings with a triazine skeleton have high electron transport properties, which helps to reduce the driving voltage. In particular, organic compounds with a phenanthroline skeleton such as mTpPPhen, PnNPhen and mPPhen2P are preferred, and organic compounds with a phenanthroline dimer structure such as mPPhen2P have excellent stability, so they are more preferred.

[0303] Note that the electron transport layer 114 may also have a stacked structure. The layer in contact with the light-emitting layer 113 in the electron transport layer 114 having a stacked structure may also be used as a hole blocking layer. When the electron transport layer in contact with the light-emitting layer is used as a hole blocking layer, it is preferable to use a material whose HOMO energy level is lower than the HOMO energy level of the material in the light-emitting layer 113 by 0.5 eV or more.

[0304] As the electron injection layer 115, a layer containing a compound or complex of an alkali metal or alkaline earth metal such as 8-hydroxyquinoline-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) or the like may be provided. As the electron injection layer 115, an alkali metal or alkaline earth metal or a compound thereof may be contained in a layer formed using a substance having an electron transport property.

[0305] Alternatively, the charge generation layer 116 may be provided instead of the electron injection layer 115 ( Figure 1B). The charge generation layer 116 is a layer that can inject holes into the layer in contact with the cathode side of the layer and inject electrons into the 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 above-mentioned composite material constituting the hole injection layer 111. In addition, the P-type layer 117 can also be formed by stacking a film containing the above-mentioned acceptor material and a film containing a hole transport material as a material constituting the composite material. By applying a potential to the P-type layer 117, electrons and holes are injected into the electron transport layer 114 and the cathode, respectively, so that the light-emitting device works. In addition, the organic compound of one embodiment of the present invention is an organic compound with a low refractive index. By using it for the P-type layer 117, a light-emitting device with good external quantum efficiency can be obtained.

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

[0307] The electron relay layer 118 contains at least a substance with electron transport properties, and can prevent the interaction between the electron injection buffer layer 119 and the P-type layer 117, and smoothly transfer electrons. The LUMO energy level of the substance with electron transport properties contained in the electron relay layer 118 is preferably set between the LUMO energy level of the acceptor substance in the P-type layer 117 and the LUMO energy level of the substance contained in the layer in the electron transport layer 114 that contacts the charge generation layer 116. Specifically, the LUMO energy level of the substance with electron transport properties in the electron relay layer 118 is above -5.0 eV, preferably above -5.0 eV and below -3.0 eV. In addition, as the substance with electron transport properties in the electron relay layer 118, it is preferred to use a phthalocyanine material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0308] The electron injection buffer layer 119 can use substances with high electron injection properties such as alkali metals, alkaline earth metals, rare earth metals and compounds of these substances (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates)).

[0309] In addition, when the electron injection buffer layer 119 contains a substance having an electron transport property and a donor substance, as a donor substance, in addition to alkali metals, alkaline earth metals, rare earth metals and compounds of these substances (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates)), tetrathianaphthacene (abbreviated as: TTN), nickelocene, decamethylnickelocene and other organic compounds can also be used. In addition, as a substance having an electron transport property, the same material as the material for the electron transport layer 114 described above can be used.

[0310] The second electrode 102 is an electrode including a cathode. The second electrode 102 may also have a stacked structure, in which case the layer in contact with the organic compound layer 103 is used as a cathode. As a substance forming the cathode, a metal, an alloy, a conductive compound, and a mixture thereof with a small work function (specifically, less than 3.8 eV) can be used. Specific examples of such cathode materials 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), or strontium (Sr), alloys containing them (MgAg, AlLi), compounds (lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ) etc.), rare earth metals such as europium (Eu), ytterbium (Yb) and alloys containing them, etc. However, by providing an 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, etc. can be used as the cathode regardless of the size of the work function.

[0311] In the case where the second electrode 102 is formed of a material that is transparent to visible light, a light-emitting device that emits light from the second electrode 102 side can be formed.

[0312] These conductive materials can be formed by dry methods such as vacuum deposition and sputtering, inkjet, spin coating, etc. Alternatively, they can be formed by wet methods such as sol-gel or by wet methods using a paste of a metal material.

[0313] The organic compound layer 103 can be formed by any of a variety of methods, whether dry or wet, such as vacuum deposition, gravure printing, offset printing, screen printing, inkjet, or spin coating.

[0314] Furthermore, the electrodes or layers described above may also be formed by using different deposition methods.

[0315] Next, refer to Figure 1C A method of describing a light-emitting device having a structure in which a plurality of light-emitting units are stacked (also referred to as a stacked device or a tandem device). The light-emitting device is a light-emitting device having a plurality of light-emitting units between an anode and a cathode. Figure 1A The structure of the organic compound layer 103 shown in FIG. Figure 1C The light emitting device shown is a light emitting device having a plurality of light emitting units. Figure 1A or Figure 1B The light-emitting device shown is a light-emitting device having one light-emitting unit.

[0316] exist Figure 1C In the embodiment, a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between the first electrode 501 and the 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 are respectively equivalent to Figure 1A The first electrode 101 and the second electrode 102 in the embodiment of the present invention can be applied to Figure 1A 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 to the first electrode 501 and the second electrode 502. Figure 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 preferably has Figure 1B The charge generation layer 116 shown in FIG. 1 has the same structure as the charge generation layer 116 shown in FIG. Since the composite material of the organic compound and the metal oxide has good carrier injection and carrier transport properties, low voltage driving and low current driving can be achieved. Note that when the surface on the anode side of the light-emitting unit is in contact with the charge generation layer 513, the charge generation layer 513 can have the function of the hole injection layer of the light-emitting unit, so the light-emitting unit may not be provided with a hole injection layer.

[0319] When the electron injection buffer layer 119 is provided in the charge generation layer 513, since the electron injection buffer layer 119 has the function of an electron injection layer in the light emitting unit on the anode side, an electron injection layer is not necessarily provided in the light emitting unit on the anode side.

[0320] Although in Figure 1C , a light-emitting device having two light-emitting units is described, but a light-emitting device having three or more light-emitting units stacked can be applied in the same manner. As in the light-emitting device according to this embodiment, by separating and arranging a plurality of light-emitting units between a pair of electrodes using the charge generation layer 513, the device can achieve high-brightness light emission while maintaining a low current density, and can achieve a device with a long life. In addition, a light-emitting device that can be driven at a low voltage and has low power consumption can be achieved.

[0321] Furthermore, by making the emission colors of each light-emitting unit different, the desired color of light can be obtained in the entire light-emitting device. For example, by obtaining red and green emission colors from the first light-emitting unit and blue emission color from the second light-emitting unit in a light-emitting device having two light-emitting units, a light-emitting device that emits white light in the entire light-emitting device can be obtained.

[0322] In addition, the organic compound layer 103, the first light-emitting unit 511, the second light-emitting unit 512, the charge generation layer and other layers and electrodes can be formed by, for example, evaporation (including vacuum evaporation), droplet jetting (also known as inkjet), coating, gravure printing, etc. In addition, it can also include low molecular weight materials, medium molecular weight materials (including oligomers, dendritic polymers) or high molecular weight materials.

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

[0324] Fig.18 Schematic diagram of a photoelectric sensor of one embodiment of the present invention. In the photoelectric sensor, a first electrode 101S is provided on an insulating layer 100S, and an organic compound layer 103S is included between the first electrode 101S and the second electrode 102S. The organic compound layer 103S includes at least a photoelectric conversion layer 123, and may also include a layer having other functions. In addition, the organic compound layer 103S includes the organic compound represented by the 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. Light 124 incident on the photoelectric conversion layer 123 can generate charges and extract them as current.

[0326] like Fig.18 As shown, the organic compound layer 103S preferably includes 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 in addition to the photoelectric conversion layer 123. Note that the organic compound layer 103S may include functional layers other than the above functional layers. Conversely, any of the above layers may not be provided.

[0327] In Embodiment 1, the organic compound represented by the general formula (G1) is preferably included in a layer for hole migration. Examples of the layer for hole migration include a hole injection layer, a hole transport layer, an electron blocking layer, and a photoelectric conversion layer.

[0328] Note that in this embodiment, the first electrode 101S and the second electrode 102S are formed to have a single-layer structure or a stacked-layer structure. When the stacked-layer structure is used, the layer in contact with the organic compound layer 103 is used as an anode or a cathode. When the electrode has a stacked-layer structure, there is no restriction on the work function of the layer other than the layer in contact with the organic compound layer 103, and the material can be selected based on the required characteristics such as resistance value, processing convenience, reflectivity, 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. Note that the light-trapping electrode is preferably formed using a material that transmits light of a wavelength that can be photoelectrically converted in the photoelectric conversion layer, and the transmittance is more preferably 50% or more, and further preferably 70% or more. As the first electrode 101S and the second electrode 102S, the hole-accepting electrode is preferably a material listed as a material preferably used as an anode of a light-emitting device, and the electron-accepting electrode is preferably a material listed as a material preferably used as a cathode of a light-emitting device.

[0329] The hole injection layer 111S, hole transport layer 112S, electron transport layer 114S, electron injection layer 115S and other functional layers may use the same materials as those listed as the materials for each functional layer constituting the light-emitting device. The functional layer that transports holes preferably contains the organic compound of one embodiment of the present invention.

[0330] The photoelectric conversion layer 123 is a layer that generates carriers according to the incident light and includes a semiconductor. As the semiconductor, inorganic semiconductors such as silicon and organic semiconductors including organic compounds can be cited. In this embodiment, an example of using an organic semiconductor as a semiconductor contained in 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 (such as vacuum evaporation method), and the manufacturing equipment can be used together, so it is preferred.

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

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

[0333] In addition, as p-type semiconductor materials, carbazole derivatives, thiophene derivatives, furan derivatives, compounds having an aromatic amine skeleton, etc. can be cited. Furthermore, as p-type semiconductor materials, naphthalene derivatives, anthracene derivatives, pyrene derivatives, triphenylene derivatives, fluorene derivatives, pyrrole derivatives, benzofuran derivatives, benzothiophene derivatives, indole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, indolecarbazole derivatives, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, quinacridone derivatives, polyphenylene vinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives or polythiophene derivatives can be cited.

[0334] Examples of n-type semiconductor materials include fullerene (e.g., C 60 , C 70 etc.), fullerene derivatives and other electron acceptor organic semiconductor materials. Fullerene has a soccer ball shape, which is energetically stable. Both the HOMO level and the LUMO level of fullerene are deep (low). Because the LUMO level of fullerene is deep, the electron acceptor property (acceptor property) is extremely high. Generally, when the π electron conjugation (resonance) is extended on a plane like benzene, the electron donor property (donor type) becomes higher. On the other hand, fullerene has a spherical shape, and although the π electron conjugation is extended, the electron acceptor property becomes higher. When the electron acceptor property is high, charge separation is caused at a high speed and efficiency, so it is beneficial for photoelectric conversion devices. C 60 , C 70 All of them have broad absorption bands in the visible light region, especially C 70 With C 60 Compared with fullerene, it has a larger π electron conjugated system and a wider absorption band in the long wavelength region, so it is preferred. In addition, as a fullerene derivative, [6,6]-phenyl-C 71 -Butyric acid methyl ester (abbreviation: PC71BM), [6,6]-phenyl-C 61 -Butyric acid methyl ester (abbreviated as: PC61BM), 1',1",4',4"-tetrahydro-di[1,4]methano-naphtho[1,2:2',3',56,60:2",3"][5,6]fullerene-C 60 (Abbreviation: ICBA) etc.

[0335] As n-type semiconductor materials, there can be mentioned 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, quinone derivatives, and the like.

[0336] In addition, the photoelectric conversion layer 123 is preferably a stacked film of a first layer including a p-type semiconductor material and a second layer including an n-type semiconductor material.

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

[0338] Furthermore, the HOMO level of the electron donor organic semiconductor material is preferably shallower (higher) than the HOMO level of the electron acceptor organic semiconductor material. The LUMO level of the electron donor organic semiconductor material is preferably shallower (higher) than the LUMO level of the electron acceptor organic semiconductor material.

[0339] In addition, spherical fullerenes can be used as electron acceptor organic semiconductor materials, and organic semiconductor materials with a shape similar to a plane can be used as electron donor organic semiconductor materials. Molecules with similar shapes tend to aggregate easily, and when the same molecules aggregate, the energy levels of the molecular orbitals are close, which can improve carrier transport properties.

[0340] In the light-emitting device and photoelectric sensor of one embodiment of the present invention having the above structure, the organic compound represented by the general formula (G1) is a material having excellent hole transport properties and high heat resistance, so by using the organic compound to manufacture the device, a device having a low driving voltage and high reliability in high-temperature driving can be provided. In addition, since the film quality changes little in the thin film containing the organic compound having such a structure, a device that is stable to heat or driving can be provided, so it is preferred. In addition, the device using the organic compound having such a structure can provide the following device: the driving voltage is low and the voltage variation during driving is small, so it has high reliability to voltage and high reliability in high-temperature driving. In addition, a low-power consumption device can be provided, so it is preferred. In addition, the organic compound having such a structure has high sublimation, does not decompose in the evaporation process, and can achieve stable production, so it is preferred from the perspective of manufacturing cost.

[0341] Implementation 3 In this embodiment, a case where 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 is described. In this embodiment, a pattern of an organic compound layer of a light-emitting device is formed by photolithography, but the light-emitting device can also be formed by conventional methods such as mask evaporation.

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

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

[0344] In this specification, for example, when describing common contents among sub-pixel 110R, sub-pixel 110G, and sub-pixel 110B, sub-pixel 110 may be referred to as sub-pixel 110. Similarly, when describing common contents among other components distinguished by letters, symbols without letters may be used for description.

[0345] Sub-pixel 110R emits red light, sub-pixel 110G emits green light, and sub-pixel 110B emits blue light. Thus, an image can be displayed on pixel portion 177. In the present embodiment, sub-pixels of three colors, red (R), green (G), and blue (B), are used as examples for description, but a combination of sub-pixels of other colors may also be used. In addition, the number of sub-pixels is not limited to three, and four or more may also be used. As four sub-pixels, for example, there may be: 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 four colors, R, G, B, and infrared light (IR); and the like.

[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 intersect.

[0347] exist Figure 2A In the example shown, sub-pixels of different colors are arranged in the X direction, and sub-pixels of the same color are arranged in the Y direction. Note that sub-pixels of different colors may be arranged in the Y direction, and sub-pixels of the same color may be arranged in the X direction.

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

[0349] exist Figure 2A In the example shown, the region 141 and the connection portion 140 are located on the right side of the pixel portion 177, but there is no particular limitation on the positions of the region 141 and the connection portion 140. In addition, the region 141 and the connection portion 140 may be one or more.

[0350] Figure 2B It is along Figure 2A An example of a cross-sectional view along the dot-dash line A1-A2 in FIG. Figure 2B As shown, the display device includes 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 disposed on a substrate (not shown). The insulating layer 175, the insulating layer 174, and the insulating layer 173 are provided with openings that reach the conductive layer 172, and a plug 176 is provided in a manner of being embedded in the opening.

[0351] In the pixel portion 177, the light emitting device 130 is provided on the insulating layer 175 and the plug 176. In addition, a protective layer 131 is provided so as to cover the light emitting device 130. The substrate 120 is bonded to the protective layer 131 by the 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] Figure 2B Although the cross sections of the plurality of inorganic insulating layers 125 and the plurality of insulating layers 127 are shown, the inorganic insulating layers 125 and the insulating layers 127 are preferably formed as connected layers when the display device is viewed from above. That is, the inorganic insulating layers 125 and the insulating layers 127 are preferably insulating layers having openings on the first electrodes.

[0353] exist Figure 2B 130R, 130G, and 130B are shown as the light emitting device 130. The light emitting device 130R, 130G, and 130B can emit light of different colors from each other. 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. In addition, the light emitting device 130R, the light emitting device 130G, or the light emitting device 130B can also emit other visible light or infrared light. Note that in Figure 2B In the embodiment, the light emitting device 130R and the light emitting device 130G, and the light emitting device 130G and the light emitting device 130B may be respectively referred to as light emitting devices adjacent to each other.

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

[0355] The light-emitting device 130R is a light-emitting device that emits red light (preferably phosphorescence), and preferably has the structure described in Embodiment 1 or Embodiment 2. The light-emitting device 130R includes 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] The light-emitting device 130G is a light-emitting device that emits green light (preferably phosphorescence), and preferably has the structure described in Embodiment 1 or Embodiment 2. The light-emitting device 130G includes a first electrode 101G (pixel electrode) composed of a conductive layer 151G and a 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. The common layer 136 is preferably an electron injection layer.

[0357] The light-emitting device 130B is a light-emitting device that emits blue light (preferably fluorescence), and preferably has the structure described in Embodiment 1 or Embodiment 2. The light-emitting device 130B includes a first electrode 101B (pixel electrode) composed of a conductive layer 151B and a 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 the pixel electrode (first electrode) and the common electrode (second electrode) included in the light emitting device is used as an anode, and the other is used as a cathode. In this embodiment, unless otherwise specified, it is sometimes assumed that the pixel electrode is used as an anode and the common electrode is used as a cathode.

[0359] The first layer 135R, the first layer 135G, and the first layer 135B are independent in the shape of islands for each light-emitting device or each light-emitting color. Note that the first layer 135R, the first layer 135G, and the first layer 135B preferably do not overlap with each other. Sometimes the first layer 135R, the first layer 135G, and the first layer 135B formed by a plurality of light-emitting devices 130 in the light-emitting device are collectively referred to as the first layer group 135A. By setting the first layer group 135A in the shape of an island for each light-emitting device 130, the leakage current between adjacent light-emitting devices 130 can be suppressed even in a high-definition display device. As a result, crosstalk can be prevented to realize a display device with extremely high contrast. In particular, a display device with high current efficiency at low brightness can be realized.

[0360] The island-shaped first layer group 135A is formed by depositing an EL film in accordance with the emission color and processing the EL film by photolithography.

[0361] The first layer 135 is preferably provided in a manner covering the top surface and the side surface of the first electrode 101 (pixel electrode) of the light-emitting device 130. Thus, compared with a structure in which the end of the first layer 135 is located inside the end of the pixel electrode, it is easy to increase the aperture ratio of the display device. In addition, by covering the side surface of the pixel electrode of the light-emitting device 130 with the first layer 135, the first electrode 101 can be prevented from contacting the second electrode 102, so that a short circuit 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. Figure 2B In the illustrated example, the first electrode 101 of the light emitting device 130 has a stacked-layer 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, for example, 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 obtained by appropriately combining these metals can be used.

[0364] As the conductive layer 152, an oxide containing any one or more selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon can be used. For example, it is preferable to use a conductive oxide containing any 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, 4.0 eV or more, so it can be preferably used as the conductive layer 152.

[0365] Each of the conductive layer 151 and the conductive layer 152 may have a stacked structure including a plurality of layers of different materials. In this case, the conductive layer 151 may include a layer using a material that can be used for the conductive layer 152 such as a conductive oxide, and the conductive layer 152 may include 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, the layer in contact with the conductive layer 152 may be a layer using a material that can be used for the conductive layer 152.

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

[0367] Next, refer to FIG. 3A to FIG. 8C Description Figure 2A An example of a method for manufacturing a display device having the structure shown.

[0368] [Production method example] Thin films (insulating films, semiconductor films, conductive films, etc.) constituting the display device can be formed by sputtering, chemical vapor deposition (CVD), vacuum evaporation, pulsed laser deposition (PLD), ALD, etc.

[0369] In addition, thin films (insulating films, semiconductor films, conductive films, etc.) that constitute the display device can be formed using wet deposition methods such as spin coating, dipping, spraying, inkjet, dispenser, screen printing, offset printing, doctor knife, slit coating, roll coating, curtain coating or doctor knife coating.

[0370] In addition, when processing a thin film constituting the display device, it is possible to perform processing using, for example, photolithography.

[0371] In the photolithography method, as the light used for exposure, for example, i-line (wavelength 365nm), g-line (wavelength 436nm), h-line (wavelength 405nm) or a mixture of these lights can be used. In addition, ultraviolet light, KrF laser or ArF laser, etc. can also be used. In addition, exposure can also be performed using liquid immersion exposure technology. In addition, as the light used for exposure, extreme ultraviolet (EUV: Extreme Ultra-violet) light or X-rays can also be used. In addition, instead of the light used for exposure, an electron beam can also be used.

[0372] For etching of the thin film, dry etching, wet etching, sand blasting, or the like can be used.

[0373] First, if Figure 3A As shown in the figure, 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] As the substrate, a substrate having heat resistance at least enough to withstand the subsequent heat treatment can be used. For example, a glass substrate; a quartz substrate; a sapphire substrate; a ceramic substrate; an organic resin substrate; or a semiconductor substrate such as a single crystal semiconductor substrate or a polycrystalline semiconductor substrate made of silicon or silicon carbide, a compound semiconductor substrate such as silicon germanium, an SOI substrate, etc. can be used.

[0375] Then, if Figure 3A As shown in FIG. 1 , openings reaching the conductive layer 172 are formed in the insulating layer 175, the insulating layer 174, and the insulating layer 173. Next, the plug 176 is formed so as to be embedded in the opening.

[0376] Then, if Figure 3A As shown in FIG. 1 , a conductive film 151f, which will later become the conductive layer 151R, the conductive layer 151G, the conductive layer 151B, and the conductive layer 151C, is formed on the plug 176 and the insulating layer 175. As the conductive film 151f, for example, a metal material can be used.

[0377] Then, if Figure 3A As shown in FIG. 1 , a resist mask 191 is formed on the conductive film 151f. The resist mask 191 can be formed by applying a photosensitive material (photoresist), exposing it to light, and developing it.

[0378] Then, if Figure 3B As shown, for example, the conductive film 151f is removed in a region that does not overlap with the resist mask 191. Thus, the conductive layer 151 is formed.

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

[0380] Then, if Figure 3D As shown, an insulating film 156f, which will later become the insulating layer 156R, the insulating layer 156G, the insulating layer 156B and the insulating layer 156C, is formed on the conductive layer 151R, the conductive layer 151G, the conductive layer 151B, the conductive layer 151C and the insulating layer 175.

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

[0382] Then, if Figure 3E As shown, by processing the insulating film 156f, the insulating layer 156R, the insulating layer 156G, the insulating layer 156B and the insulating layer 156C are formed.

[0383] Then, if Figure 4A As shown, 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] As the conductive film 152f, for example, a conductive oxide can be used. The conductive film 152f can also have a stacked-layer structure.

[0385] Then, if Figure 4B As shown, 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] Then, if Figure 4C As shown in FIG. 1 , an organic compound film 103Rf is formed on the conductive layer 152R, the conductive layer 152G, the conductive layer 152B, and the insulating layer 175. Figure 4C As shown, the organic compound film 103Rf is not formed on the conductive layer 152C.

[0387] Then, if Figure 4C As shown, 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 large etching selectivity ratio with the organic compound film 103Rf. The mask film 159Rf is made of a film having a large etching selectivity ratio with the sacrificial film 158Rf.

[0390] In addition, the sacrificial film 158Rf and the mask film 159Rf are formed at a temperature lower than the heat resistance 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. to 200° C., preferably 100° C. to 150° C., and more preferably 100° C. to 120° C.

[0391] As the sacrificial film 158Rf and the mask film 159Rf, a film that can be removed by a wet etching method or a dry etching method is preferably used.

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

[0393] As the sacrificial film 158Rf and the mask film 159Rf, for example, 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 can be used.

[0394] As the sacrificial film 158Rf and the mask film 159Rf, for example, metal materials such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, and tantalum, or alloy materials containing the metal materials can be used. In particular, low melting point materials such as aluminum and silver are preferably used. By using a metal material that can shield ultraviolet rays as one or both of the sacrificial film 158Rf and the mask film 159Rf, it is possible to suppress ultraviolet rays from irradiating the organic compound film 103Rf during pattern exposure and suppress the degradation of the organic compound film 103Rf, which is preferred.

[0395] In addition, as 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), indium tin oxide containing silicon, etc. can be used respectively.

[0396] Note that element M (M is one or more of aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten and magnesium) can also be used in the above-mentioned metal oxides instead of the above-mentioned gallium.

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

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

[0399] Then, if Figure 4C As shown, a resist mask 190R is formed. The resist mask 190R can be formed by applying a photosensitive material (photoresist), exposing and developing the same.

[0400] Resist mask 190R is provided at a position overlapping conductive layer 152R. Resist mask 190R is preferably provided also at a position overlapping conductive layer 152C. This can prevent conductive layer 152C from being damaged during the manufacturing process of the display device.

[0401] Then, if Figure 4D As shown, a portion of the mask film 159Rf is removed using the resist mask 190R to form a mask layer 159R. The mask layer 159R remains on the conductive layer 152R and the conductive layer 152C. Then, the resist mask 190R is removed. Next, a portion of the sacrificial film 158Rf is removed using the mask layer 159R as a mask (also referred to as a hard mask) to form a sacrificial layer 158R.

[0402] By using the wet etching method, the damage to the organic compound film 103Rf during the 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 the wet etching method is used, for example, it is preferable to use an acidic aqueous solution such as a developer, an alkaline aqueous solution such as a tetramethylammonium hydroxide (TMAH) aqueous solution, a dilute hydrofluoric acid, oxalic acid, phosphoric acid, acetic acid, nitric acid, or a mixed liquid thereof.

[0403] In addition, when dry etching is used in processing the sacrificial film 158Rf, degradation 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 by the same method as the resist mask 191 .

[0405] Then, if Figure 4D As shown, the organic compound film 103Rf is processed to form the first layer 135R. For example, the mask layer 159R and the sacrificial layer 158R are used as a hard mask and a portion of the organic compound film 103Rf is removed, thereby forming the first layer 135R.

[0406] Therefore, if Figure 4D As shown, the stacked structure of the first layer 135R, the sacrificial layer 158R and the mask layer 159R remains on the conductive layer 152R. In addition, the conductive layer 152G and the conductive layer 152B are exposed.

[0407] The processing of the organic compound film 103Rf is preferably performed using anisotropic etching, and anisotropic dry etching is particularly preferred. Alternatively, wet etching may be used.

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

[0409] In addition, an oxygen-containing gas may be used as the etching gas. When the etching gas contains oxygen, the etching rate can be increased. Therefore, etching can be performed under low power conditions while maintaining a sufficient etching rate. Therefore, damage to the organic compound film 103Rf can be suppressed. In addition, defects such as adhesion of reaction products generated during etching can be suppressed.

[0410] When a dry etching method is used, for example, it is preferable to use a 2 CF 4 , C 4 F 8 , SF 6 , CHF 3 , Cl 2 , H 2 O、BCl 3 , He, Ar and other Group 18 elements as the etching gas. Alternatively, it is preferred to use a gas containing one or more of the above gases and oxygen as the etching gas. Alternatively, oxygen gas may also be used as the etching gas.

[0411] Then, if Figure 5A As shown, an organic compound film 103Gf which will later become a first layer 135G is formed.

[0412] The organic compound film 103Gf can be formed using the same method as that which can be used for forming the organic compound film 103Rf. In addition, the organic compound film 103Gf can have the same structure as that of the organic compound film 103Rf.

[0413] Then, if Figure 5AAs shown in FIG. 1 , a sacrificial film 158Gf and a mask film 159Gf are sequentially formed. 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 of the sacrificial film 158Rf and the mask film 159Rf. The materials and forming methods of the resist mask 190G are the same as those of the resist mask 190R.

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

[0415] Then, if Figure 5B As shown, a portion of the mask film 159Gf is removed using the resist mask 190G, thereby forming a mask layer 159G. The mask layer 159G remains on the conductive layer 152G. Then, the resist mask 190G is removed. Next, using the mask layer 159G as a mask, a portion of the sacrificial film 158Gf is removed, thereby forming a sacrificial layer 158G. Next, the organic compound film 103Gf is processed to form the first layer 135G.

[0416] Then, if Figure 5C As shown, an organic compound film 103Bf is formed.

[0417] The organic compound film 103Bf can be formed using the same method as that which can be used for forming the organic compound film 103Rf. In addition, the organic compound film 103Bf can have the same structure as that of the organic compound film 103Rf.

[0418] Then, if Figure 5C As shown, a sacrificial film 158Bf and a mask film 159Bf are sequentially formed. Then, a resist mask 190B is formed. The materials and forming methods of the sacrificial film 158Bf and the mask film 159Bf are the same as those of the sacrificial film 158Rf and the mask film 159Rf. The materials and forming methods of the resist mask 190B are the same as those of the resist mask 190R.

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

[0420] Then, if Figure 5D As shown, a portion of the mask film 159Bf is removed using the resist mask 190B, thereby forming the mask layer 159B. The mask layer 159B remains on the conductive layer 152B. Then, the resist mask 190B is removed. Next, using the mask layer 159B as a mask, a portion of the sacrificial film 158Bf is removed, thereby forming the sacrificial layer 158B. Next, the organic compound film 103Bf is processed to form the first layer 135B. For example, using the mask layer 159B and the sacrificial layer 158B as a hard mask, a portion of the organic compound film 103Bf is removed, thereby forming the first layer 135B.

[0421] Therefore, if Figure 5D As shown, the stacked structure of the first layer 135B, the sacrificial layer 158B and the mask layer 159B remains on the conductive layer 152B. In addition, the mask layer 159R and the mask layer 159G are exposed.

[0422] Note that the side surfaces of the first layer 135R, the first layer 135G, and the first layer 135B are preferably perpendicular or substantially perpendicular to the formed surface. For example, the angle formed by the formed surface and these side surfaces is preferably not less than 60 degrees and not more than 90 degrees.

[0423] As described above, the distance between two adjacent layers of the first layer 135R, the first layer 135G, and the first layer 135B formed using photolithography can be reduced to less than 8μm, less than 5μm, less than 3μm, less than 2μm, or less than 1μm. Here, for example, the distance can be specified based on the distance between the relative ends of two adjacent layers of the first layer 135R, the first layer 135G, and the first layer 135B. In this way, by reducing the distance between the island-shaped organic compound layers, a display device with high clarity and a large aperture ratio can be provided. In addition, the distance between the first electrodes of adjacent light-emitting devices can be reduced, for example, to less than 10μm, less than 8μm, less than 5μm, less than 3μm, or less than 2μm. In addition, the distance between the first electrodes of adjacent light-emitting devices is preferably greater than 2μm and less than 5μm.

[0424] Then, if Fig. 6A As shown, mask layer 159R, mask layer 159G and mask layer 159B are preferably removed.

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

[0426] Alternatively, the mask layer may be removed by dissolving it in a polar solvent such as water or alcohol. Examples of the alcohol include ethanol, methanol, isopropyl alcohol (IPA), and glycerin.

[0427] After removing the mask layer, a drying treatment may be performed to remove water attached to the surface. For example, a heat treatment may be performed in an inert gas atmosphere or a reduced pressure atmosphere. The heat treatment may 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. By adopting a reduced pressure atmosphere, drying can be performed at a lower temperature, so it is preferred.

[0428] Then, if Figure 6B As shown, an inorganic insulating film 125f is formed.

[0429] Then, if Figure 6C As shown in FIG. 1 , an insulating film 127 f which will later become an insulating layer 127 is formed on the inorganic insulating film 125 f.

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

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

[0432] The inorganic insulating film 125f is preferably formed by, for example, the ALD method. The ALD method is preferred because it can reduce deposition damage and deposit a film with high coverage. 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 the wet deposition method described above. The insulating film 127f is preferably formed by, for example, a photosensitive material by spin coating, and more specifically, is preferably formed by using a photosensitive resin composition containing an acrylic resin.

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

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

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

[0437] Then, if Fig. 7A As shown, development is performed to remove the exposed region in the insulating film 127f, thereby forming the insulating layer 127a.

[0438] Then, if Figure 7BAs shown, the insulating layer 127a is used as a mask to perform etching to remove a portion of the inorganic insulating film 125f, thereby reducing the thickness of a portion of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B. As a result, the inorganic insulating layer 125 is formed under the insulating layer 127a. In addition, the surface of the thin portion of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B is exposed. Hereinafter, the etching process using the insulating layer 127a as a mask is sometimes referred to as the first etching process.

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

[0440] When dry etching is performed, it is preferred to use a chlorine-based gas. As a chlorine-based gas, Cl 2 , BCl 3 、SiCl 4 and CCl 4 One gas or a mixture of two or more gases among the above. In addition, one gas or a mixture of two or more gases among oxygen gas, hydrogen gas, helium gas, argon gas, etc. can be appropriately added to the above chlorine-based gas. By utilizing dry etching, the thin thickness areas of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B can be formed with excellent in-plane uniformity.

[0441] As a dry etching device, a dry etching device having a high-density plasma source can be used. As a dry etching device having a high-density plasma source, for example, an inductively coupled plasma (ICP: Inductively Coupled Plasma) etching device can be used. Alternatively, a capacitively coupled plasma (CCP: Capacitively Coupled Plasma) etching device including parallel plate electrodes can be used.

[0442] In addition, it is preferred to perform the first etching process using wet etching. By using the wet etching method, the 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, an alkaline solution can be used for wet etching. For example, TMAH can be used as an alkaline solution in the wet etching of an aluminum oxide film. In addition, an acidic solution containing a fluoride can also be used. In this case, wet etching can be performed using a puddle method. Note that when the inorganic insulating film 125f is deposited using the same material as the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B, it is preferred because the above-mentioned etching process can be performed together.

[0443] In the first etching process, the sacrificial layers 158R, 158G, and 158B are not completely removed, and the etching process is stopped in a state where the thickness is reduced. In this way, 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 subsequent process.

[0444] Next, the entire substrate is preferably exposed to visible light or ultraviolet light to irradiate the insulating layer 127a. The energy density of this exposure is preferably greater than 0 mJ / cm 2 And 800mJ / cm 2 Below, more preferably greater than 0 mJ / cm 2 And 500mJ / cm 2 By performing such exposure after development, the transparency of the insulating layer 127a can be improved. In addition, the substrate temperature required for heat treatment in a later step for deforming the insulating layer 127a into a tapered shape can be reduced.

[0445] Here, by providing an oxygen blocking insulating layer (for example, an aluminum oxide film) as the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B, diffusion of hydrogen into the first layer 135R, the first layer 135G, and the first layer 135B can be suppressed.

[0446] Next, a heat treatment (also called post-baking) is performed. By performing the heat treatment, the insulating layer 127a can be deformed into an insulating layer 127 having a tapered shape on its side. Figure 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, and more preferably 70°C to 130°C. The heating atmosphere can be either an air atmosphere or an inert gas atmosphere. In addition, the heating atmosphere can be either an air atmosphere or a reduced pressure atmosphere. Thus, the adhesion between the insulating layer 127 and the inorganic insulating layer 125 can be improved, and the corrosion resistance of the insulating layer 127 can also be improved.

[0447] In the first etching process, the sacrificial layers 158R, 158G, and 158B are not completely removed, but the sacrificial layers 158R, 158G, and 158B are left thin, so that the first layers 135R, 135G, and 135B can be prevented from being damaged and deteriorated during the heating process. Thus, the reliability of the light-emitting device can be improved.

[0448] Then, if Fig. 8AAs shown, the insulating layer 127 is used as a mask to perform etching to remove a portion of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B. As a result, an opening is formed in each of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B, and the top surface of the first layer 135R, the first layer 135G, the first layer 135B, and the conductive layer 152C is exposed. Note that this etching process may be referred to as a second etching process below.

[0449] The end of the inorganic insulating layer 125 is covered with the insulating layer 127. Fig. 8A An example is shown in which a portion 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, the damage to the first layer 135R, the first layer 135G, and the first layer 135B can be reduced compared with the case of using the dry etching method. For example, the wet etching can be performed using an alkaline solution or an acidic solution. In order to prevent the first layer 135 from dissolving, it is preferable to use an aqueous solution.

[0451] Then, if Figure 8B As shown in FIG. 1 , 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 using a method such as sputtering or vacuum evaporation. Figure 2A and Figure 2B As shown, the first layer 135 may be formed as a stacked structure of the first layer 135 and the common layer 136 , and the second electrode 102 may be formed thereon.

[0452] Then, if Figure 8C As shown, a protective layer 131 is formed on the second electrode 102. The protective layer 131 can be formed by vacuum evaporation, sputtering, CVD, ALD or other methods.

[0453] Next, the substrate 120 is bonded to the protective layer 131 using the resin layer 122, whereby a display device can be manufactured. As described above, in the method for manufacturing a display device according to one embodiment of the present invention, the insulating layer 156 is provided so as to include a region overlapping with the 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. Thus, the yield of the display device can be improved, and the occurrence of defects can be suppressed.

[0454] As described above, in a method for manufacturing a display device of one embodiment of the present invention, the island-shaped first layer 135R, the island-shaped first layer 135G, and the island-shaped first layer 135B are not formed using a high-precision metal mask but are formed by depositing a film on one surface and then processing it, so that the island layer can be formed with a uniform thickness. In addition, a high-definition display device or a display device with a high aperture ratio can be realized. In addition, even if the clarity or aperture ratio is high and the distance between sub-pixels 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 sub-pixels. Therefore, leakage current can be suppressed between sub-pixels. Thus, crosstalk can be prevented and a display device with extremely high contrast can be realized. In addition, even a display device including a series-type light-emitting device manufactured using a photolithography method can provide a display device with good characteristics.

[0455] Implementation 4 In this embodiment, a display device which is one embodiment of the present invention is described.

[0456] The display device of this embodiment can be a high-definition display device. Therefore, for example, the display device of this embodiment can be used as a display unit of information terminal devices (wearable devices) such as watch-type and bracelet-type devices, and a display unit of wearable devices that can be worn on the head such as VR devices such as head-mounted displays (HMDs) and glasses-type AR devices.

[0457] In addition, the display device of this embodiment can be a high-resolution display device or a large display device. Therefore, for example, the display device of this embodiment can be used as a display portion of the following devices: electronic devices with large screens such as television devices, desktop or notebook personal computers, displays for computers, etc., digital signage and large game machines such as pinball machines, etc.; digital cameras; digital video cameras; digital photo frames; mobile phones; portable game consoles; portable information terminals; and sound reproduction devices.

[0458] [Display module] Fig.9A 2 is 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 one of the display devices 100B to 100E to be described later.

[0459] The display module 280 includes a substrate 291 and a substrate 292. The display module 280 includes a display portion 281. The display portion 281 is an image display region in the display module 280, and light from each pixel provided in a pixel portion 284 described below can be viewed.

[0460] Fig. 9B2 is a perspective view of a structure on one side of a substrate 291. 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. In addition, a terminal portion 285 for connecting to the FPC 290 is provided on a portion of the substrate 291 that is not overlapped by the pixel portion 284. The terminal portion 285 is electrically connected to the circuit portion 282 via a wiring portion 286 composed of a plurality of wirings.

[0461] The pixel portion 284 includes a plurality of pixels 284 a arranged periodically. Fig. 9B An enlarged view of a pixel 284a is shown on the right side of FIG. The pixel 284a can adopt various structures described in the above embodiments. Fig. 9B , the pixel 284a is shown to have Figure 2A and Figure 2B The pixel 178 shown has the same structure.

[0462] The pixel circuit portion 283 includes a plurality of pixel circuits 283 a arranged periodically.

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

[0464] The circuit unit 282 includes a circuit for driving each pixel circuit 283a of the pixel circuit unit 283. For example, it preferably includes one or both of a gate line driving circuit and a source line driving circuit. In addition, it may include at least one of a calculation circuit, a storage circuit, and a power supply circuit.

[0465] The FPC 290 is used as wiring for supplying video signals, power supply potential, and the like from the outside to the circuit portion 282. Alternatively, an IC may be mounted on the FPC 290.

[0466] The display module 280 may have a structure in which one or both of the pixel circuit portion 283 and the circuit portion 282 are stacked on the lower side of the pixel portion 284 , so that the display portion 281 may have an extremely high aperture ratio (effective display area ratio).

[0467] This high-definition display module 280 is suitable for use in VR devices such as HMD or glasses-type AR devices. For example, because the display module 280 has a very high-definition display unit 281, in a structure where the display unit of the display module 280 is viewed through a lens, even if the display unit is magnified by a lens, the user cannot see the pixels, thereby achieving a highly immersive display. In addition, the display module 280 is not limited to this, and can also be applied to electronic devices with a relatively small display unit.

[0468] [Display device 100A] Fig. 10AThe display device 100A shown 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] Substrate 301 is equivalent to Fig.9A and Fig. 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 portion 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 is used as a gate electrode. The insulating layer 313 is located between the substrate 301 and the conductive layer 311 and is used as a gate insulating layer. The low resistance region 312 is a region doped with impurities in the substrate 301 and is used as a source or a drain. The insulating layer 314 covers the side of the conductive layer 311.

[0470] Furthermore, 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 the capacitor 240 is provided over the insulating layer 261 .

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

[0473] The conductive layer 241 is provided on the insulating layer 261 and 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 through the plug 271 embedded in the insulating layer 261. The insulating layer 243 is provided in a manner covering the conductive layer 241. The conductive layer 245 is provided in a region overlapping with the conductive layer 241 via the insulating layer 243.

[0474] An insulating layer 255 is provided to cover 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. The light emitting devices 130R, 130G, and 130B are provided on the insulating layer 175. An insulator is provided in a region between adjacent light emitting devices.

[0475] The insulating layer 156R is provided so as to include a region overlapping with the side surface of the conductive layer 151R, the insulating layer 156G is provided so as to include a region overlapping with the side surface of the conductive layer 151G, and the insulating layer 156B is provided so as to include a region overlapping with the side surface of the conductive layer 151B. In addition, the conductive layer 152R is provided so as to cover the conductive layer 151R and the insulating layer 156R, the conductive layer 152G is provided so as to cover the conductive layer 151G and the insulating layer 156G, and the conductive layer 152B is provided so as to cover the conductive layer 151B and the insulating layer 156B. The sacrificial layer 158R is located on the first layer 135R, the sacrificial layer 158G is located on the first layer 135G, and the sacrificial layer 158B is located on the first layer 135B.

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

[0477] In addition, a protective layer 131 is provided on the light emitting device 130R, the light emitting device 130G, and the light emitting device 130B. The substrate 120 is bonded to the protective layer 131 via a resin layer 122. The details of the components of the light emitting device 130 to the substrate 120 can be referred to Embodiment 3. The substrate 120 corresponds to Fig.9A substrate 292.

[0478] Fig. 10B Show Fig. 10A A modified example of the display device 100A shown. Fig. 10B The display device shown includes a coloring layer 132R, a coloring layer 132G, and a coloring layer 132B, and the light emitting device 130 has a region overlapping one of the coloring layer 132R, the coloring layer 132G, and the coloring layer 132B. Fig. 10B In the display device shown, the light emitting device 130 can emit white light, for example. In addition, for example, the coloring layer 132R, the coloring layer 132G, and the coloring layer 132B can transmit red light, green light, and blue light, respectively.

[0479] [Display device 100B] Fig.11 A perspective view showing a display device 100B is shown. Fig.12 A cross-sectional view of the display device 100C is shown.

[0480] The display device 100B has a structure in which a substrate 352 and a substrate 351 are bonded together. Fig.11 In FIG. 3 , the substrate 352 is indicated by a dotted line.

[0481] The display device 100B includes a pixel portion 177 , a connection portion 140 , a circuit 356 , a wiring 355 , and the like. Fig.11 FIG. 1 shows an example in which the display device 100B is equipped with the IC 354 and the FPC 353. Fig.11 The structure shown is called a display module including the display device 100B, IC (integrated circuit) and FPC. Here, the substrate of the display device with a connector such as FPC mounted thereon or the substrate with IC mounted thereon is called a display module.

[0482] The connection part 140 is disposed outside the pixel part 177. There may be one or more connection parts 140. In the connection part 140, the common electrode of the light emitting device is electrically connected to the conductive layer, and power can be supplied to the common electrode.

[0483] As the circuit 356, for example, a scan line driver circuit can be used.

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

[0485] Fig.11 An example of providing IC354 on substrate 351 by COG (Chip On Glass) method or COF (Chip On Film) method is shown. As IC354, for example, an IC including a scanning line driving circuit or a signal line driving circuit can be used. Note that the display device 100B and the display module do not necessarily have to be provided with an IC. In addition, for example, the IC can also be mounted on an FPC by using a COF method.

[0486] Fig.12 An example of a cross section of 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 of the display device 100C is shown.

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

[0488] For details of the light emitting device 130R, the light emitting device 130G, and the light emitting device 130B, reference may be made to Embodiment 1.

[0489] The light emitting device 130R includes a conductive layer 224R, a conductive layer 151R on the conductive layer 224R, and a conductive layer 152R on the conductive layer 151R. The light emitting device 130G includes a conductive layer 224G, a conductive layer 151G on the conductive layer 224G, and a conductive layer 152G on the conductive layer 151G. The light emitting device 130B includes a conductive layer 224B, a conductive layer 151B on the conductive layer 224B, and a conductive layer 152B on the conductive layer 151B.

[0490] The conductive layer 224R is connected to the conductive layer 222b included in 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. The insulating layer 156R is provided so as to include a region in contact with a side surface of the conductive layer 151R, and the conductive layer 152R is provided so as to cover the conductive layer 151R and the insulating layer 156R.

[0491] The conductive layer 224G, conductive layer 151G, conductive layer 152G, and insulating layer 156G in the light-emitting device 130G and the conductive layer 224B, conductive layer 151B, conductive layer 152B, and insulating layer 156B in the light-emitting device 130B are the same as the conductive layer 224R, conductive layer 151R, conductive layer 152R, and insulating layer 156R in the light-emitting device 130R, so detailed description is omitted.

[0492] Concave portions are formed in conductive layer 224R, conductive layer 224G, and conductive layer 224B so as to cover the openings provided in insulating layer 214. The concave portions are filled with layer 128.

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

[0494] Layer 128 may be an insulating layer or a conductive layer. Layer 128 may be formed of various inorganic insulating materials, organic insulating materials, and conductive materials as appropriate. In particular, layer 128 is preferably formed of an insulating material, and more preferably formed of an organic insulating material. Layer 128 may be formed of, for example, the organic insulating material that can be used for insulating layer 127.

[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 by an adhesive layer 142. The substrate 352 is provided with a light shielding layer 157. The sealing of the light emitting device 130 may adopt a solid sealing structure or a hollow sealing structure. Fig.12 In the embodiment, the space between the substrate 352 and the substrate 351 is filled with the adhesive layer 142, that is, a solid sealing structure is adopted. Alternatively, the space may be filled with an inert gas (nitrogen or argon, etc.), that is, a hollow sealing structure is adopted. In this case, the adhesive layer 142 may also be arranged in a manner that does not overlap with the light-emitting device. In addition, a resin different from the adhesive layer 142 arranged in a frame shape may be used to fill the space.

[0496] Fig.12 The following example is shown: the connection portion 140 includes a conductive layer 224C processed from the same conductive film as the conductive layers 224R, 224G, and 224B, a conductive layer 151C processed from the same conductive film as the conductive layers 151R, 151G, and 151B, and a conductive layer 152C processed from the same conductive film as the conductive layers 152R, 152G, and 152B. In addition, Fig.12 An example is shown in which the insulating layer 156C is provided so as to include a region overlapping with the side surface of the conductive layer 151C.

[0497] The display device 100C is a top emission type display device. The light emitting device emits light to the substrate 352 side. The substrate 352 preferably uses a material with high transmittance to visible light. When the light emitting device emits infrared light or near-infrared light, it is preferred to use a material with high transmittance to the above light. The first electrode (pixel electrode) includes a material that reflects visible light, and the second electrode (counter electrode) 155 includes 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 sequentially provided on the substrate 351. A portion of the insulating layer 211 is used as a gate insulating layer of each transistor. A portion of the insulating layer 213 is used as a gate insulating layer of each transistor. The insulating layer 215 is provided in a manner covering the transistor. The insulating layer 214 is provided in a manner covering the transistor and is used as a planarization layer. In addition, there is no particular limitation on the number of gate insulating layers and the number of insulating layers covering the transistor, and it can be one or more than two.

[0499] As the insulating layer 211 , the insulating layer 213 , and the insulating layer 215 , an inorganic insulating film is preferably used.

[0500] As the insulating layer 214 serving as a planarizing layer, an organic insulating layer is preferably used.

[0501] The transistor 201 and the transistor 205 include: a conductive layer 221 used as a gate; an insulating layer 211 used as a gate insulating layer; a conductive layer 222a and a conductive layer 222b used as a source and a drain; a semiconductor layer 231; an insulating layer 213 used as a gate insulating layer; and a conductive layer 223 used as a gate.

[0502] A connection portion 204 is provided in a region of the substrate 351 that is not overlapped by the substrate 352. In the connection portion 204, the wiring 355 is electrically connected to the FPC 353 through the conductive layer 166 and the connection layer 242. The following example is shown: the conductive layer 166 has a laminated structure of a conductive film obtained by processing the same conductive film as the conductive layer 224R, the conductive layer 224G, and the conductive layer 224B, a conductive film obtained by processing the same conductive film as the conductive layer 151R, the conductive layer 151G, and the conductive layer 151B, and a conductive film obtained by processing the same conductive film as the conductive layer 152R, the conductive layer 152G, and the conductive layer 152B. The conductive layer 166 is exposed on the top surface of the connection portion 204. Therefore, the connection portion 204 can be electrically connected to the FPC 353 through the connection layer 242.

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

[0504] The substrate 351 and the substrate 352 can each adopt a material that can be used for the substrate 120 .

[0505] As the adhesive layer 142 , a material that can be used for the resin layer 122 can be used.

[0506] As the connection layer 242 , an anisotropic conductive film (ACF: Anisotropic Conductive Film), anisotropic conductive paste (ACP: Anisotropic Conductive Paste), or the like can be used.

[0507] [Display device 100D] Fig.13 The display device 100D shown in FIG. Fig.12 The main difference of the illustrated display device 100C is 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 to use a material having high transmittance to visible light for the substrate 351. On the other hand, there is no limitation on the transmittance of the material used for the substrate 352.

[0509] A light shielding layer 157 is preferably formed between the substrate 351 and the transistor 201 and between the substrate 351 and the transistor 205 . Fig.13 An example is shown in which a light-shielding layer 157 is provided over a substrate 351 , an insulating layer 153 is provided over the light-shielding layer 157 , and transistors 201 , 205 , and the like are provided over the insulating layer 153 .

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

[0511] The light emitting device 130B includes a conductive layer 112B, a conductive layer 126B on the conductive layer 112B, and a conductive layer 129B on the conductive layer 126B.

[0512] The conductive layers 112R, 112B, 126R, 126B, 129R, and 129B are all made of a material having high transmittance to visible light. It is preferable to use a material that reflects visible light as the second electrode.

[0513] Note that although Fig.13 Although the light emitting device 130G is not shown in the figure, the light emitting device 130G is also provided.

[0514] in addition, Fig.13 The example in which the top surface of the layer 128 has a flat portion is shown, but the shape of the layer 128 is not particularly limited.

[0515] [Display device 100E] Fig.14 The display device 100E shown is Fig.12 The display device 100E is a variation of the display device 100C shown in FIG. 1 . The display device 100E is different from the display device 100C mainly in that it includes a coloring layer 132R, a coloring layer 132G, and a coloring layer 132B.

[0516] In the display device 100E, the light emitting device 130 has a region overlapping one of the coloring layer 132R, the coloring layer 132G, and the coloring layer 132B. The coloring layer 132R, the coloring layer 132G, and the coloring layer 132B may be provided on a surface of the substrate 352 on the substrate 351 side. An end portion of the coloring layer 132R, an end portion of the coloring layer 132G, and an end portion of the coloring layer 132B may overlap the light shielding layer 157.

[0517] In the display device 100E, the light emitting device 130 may emit white light, for example. In addition, for example, the coloring layer 132R, the coloring layer 132G, and the coloring layer 132B may transmit red light, green light, and blue light, respectively. In addition, the display device 100E may also adopt a structure in which the coloring layer 132R, the coloring layer 132G, and the coloring layer 132B are provided between the protective layer 131 and the adhesive layer 142.

[0518] Fig.12 and Fig.14 The example in which the top surface of the layer 128 has a flat portion is shown, but 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 this specification, when a plurality of configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate.

[0520] Implementation method 5 In this embodiment, an electronic device which is one embodiment of the present invention is described.

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

[0522] Electronic devices include, for example, television sets, desktop or notebook personal computers, displays for computers, etc., digital signage, large-scale game consoles such as pinball machines, and other electronic devices with larger screens, as well as digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, portable information terminals, sound reproduction devices, and the like.

[0523] In particular, since the display device of one embodiment of the present invention can improve the clarity, it can be appropriately used in electronic devices including a smaller display unit. Examples of such electronic devices include watch-type and bracelet-type information terminal devices (wearable devices), wearable devices that can be worn on the head, VR devices such as head-mounted displays, glasses-type AR devices, and MR devices.

[0524] The electronic device of this embodiment may also include a sensor (the sensor has the function of measuring the following factors: force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electricity, radiation, flow, humidity, inclination, vibration, smell or infrared).

[0525] Reference FIG. 15A to FIG. 15DAn example of a wearable device that can be worn on the head is described.

[0526] Fig.15A The electronic device 700A shown and Fig. 15B The electronic devices 700B shown include 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 components 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, a highly reliable electronic device can be realized.

[0528] Both electronic devices 700A and 700B can project the image displayed by display panel 751 onto display region 756 in optical member 753. Since optical member 753 is light-transmissive, the user can see the image displayed on the display region superimposed on the transmitted image seen through optical member 753.

[0529] The electronic device 700A and the electronic device 700B may also be provided with a camera capable of photographing the front as an imaging unit. In addition, by providing an acceleration sensor such as a gyro sensor on the electronic device 700A and the electronic device 700B, the user's head orientation can be detected and an image corresponding to the direction can be displayed on the display area 756.

[0530] The communication unit includes a wireless communication device, through which, for example, a video signal can be supplied. In addition, the communication unit may include a connector to which a cable for supplying the video signal and the power supply potential can be connected, instead of or in addition to the wireless communication device.

[0531] Furthermore, electronic device 700A and electronic device 700B are provided with batteries, and can be charged wirelessly or by wire, or both.

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

[0533] As the touch sensor module, various touch sensors can be used. For example, various methods such as electrostatic capacitance, resistance film, infrared, electromagnetic induction, surface acoustic wave, and optical can be used. In particular, it is preferred to use electrostatic capacitance or optical sensors in the touch sensor module.

[0534] Fig. 15C The electronic device 800A shown and Fig.15DThe electronic devices 800B shown each include a pair of display portions 820 , a housing 821 , a communication portion 822 , a pair of mounting portions 823 , a control portion 824 , a pair of imaging portions 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. This makes it possible to realize an electronic device with high reliability.

[0536] The display unit 820 is provided at a position visible through the lens 832 inside the housing 821. In addition, by displaying different images on each of the pair of display units 820, three-dimensional display using parallax can be performed.

[0537] The electronic device 800A and the electronic device 800B preferably have a mechanism that can adjust the left and right positions of the lens 832 and the display unit 820 so that the lens 832 and the display unit 820 are located at the most appropriate positions according to the position of the user's eyes.

[0538] The user can wear the electronic device 800A or the electronic device 800B on the head using the mounting portion 823 .

[0539] The imaging unit 825 has a function of acquiring external information. The data acquired by the imaging unit 825 can be output to the display unit 820. An image sensor can be used in the imaging unit 825. In addition, a plurality of cameras can be provided to be able to correspond to various viewing angles such as telephoto and wide angle.

[0540] The electronic device 800A may also include a vibration mechanism for use as a bone conduction headset.

[0541] Electronic device 800A and electronic device 800B may both include input terminals. Cables for supplying video signals from a video output device or the like, power for charging a battery provided in the electronic device, and the like may be connected to the input terminals.

[0542] The electronic device according to one embodiment of the present invention may have a function of wirelessly communicating with the earphone 750 .

[0543] In addition, the electronic device may include an earphone unit. Fig. 15B The electronic device 700B shown includes an earphone unit 727. A part of the wiring connecting the earphone unit 727 and the control unit may be arranged inside the housing 721 or the mounting unit 723.

[0544] Likewise, Fig.15D The electronic device 800B shown includes an earphone unit 827. For example, a structure in which the earphone unit 827 and the control unit 824 are connected in a wired manner may be adopted.

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

[0546] Fig.16A The electronic device 6500 shown is a portable information terminal device 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, a light source 6508, and the like. The display portion 6502 has a touch panel function.

[0548] The display device of one embodiment of the present invention can be used as the display portion 6502. Thus, a highly reliable electronic device can be achieved.

[0549] Fig. 16B 65 is a schematic cross-sectional view of an end portion of a housing 6501 on a side of a microphone 6506 .

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

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

[0552] In a region outside the display portion 6502, a portion of the display panel 6511 is folded back, and the folded back portion 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 panel 6511 can use a display device of one embodiment of the present invention. Thus, 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 installed while suppressing the thickness of the electronic device. In addition, by folding a portion of the display panel 6511 to provide a connection portion with the FPC 6515 on the back of the pixel portion, an electronic device with a narrow frame can be realized.

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

[0555] The display device of one embodiment of the present invention can be used as the display portion 7000. Thus, a highly reliable electronic device can be realized.

[0556] The operation can be performed by utilizing the operation switch included in the housing 7171 and the remote control operation machine 7151 provided separately. Fig. 16C The operation of television device 7100 is shown.

[0557] Fig.16D 1 shows an example of a notebook personal computer. The notebook personal computer 7200 includes a housing 7211 , a keyboard 7212 , a pointing device 7213 , an external connection port 7214 , and the like. A display portion 7000 is incorporated in the housing 7211 .

[0558] The display device of one embodiment of the present invention can be used as the display portion 7000. Thus, a highly reliable electronic device can be realized.

[0559] Fig.16E and Fig.16F An example of digital signage is shown.

[0560] Fig.16E The digital signage 7300 shown includes a housing 7301, a display unit 7000, a speaker 7303, etc. In addition, an LED lamp, operation keys (including a power switch or an operation switch), a connection terminal, various sensors, a microphone, etc. may be included.

[0561] Fig.16F The digital signage 7400 is shown to be disposed on a cylindrical pillar 7401. The digital signage 7400 includes a display unit 7000 disposed along a curved surface of the pillar 7401.

[0562] exist Fig.16E and Fig.16F In the embodiment of the present invention, the display device according to one embodiment of the present invention can be used for the display portion 7000. Thus, a highly reliable electronic device can be achieved.

[0563] The larger the display unit 7000 is, the more information can be provided at one time. The larger the display unit 7000 is, the easier it is to attract people's attention, for example, the advertising effect can be improved.

[0564] like Fig.16E and Fig.16F As shown, the digital signage 7300 or the digital signage 7400 can preferably be linked with the information terminal device 7311 or the information terminal device 7411 such as a smart phone carried by the user through wireless communication.

[0565] FIG. 17A to FIG. 17GThe electronic device shown includes a housing 9000, a display portion 9001, a speaker 9003, operation keys 9005 (including a power switch or an operation switch), a connecting terminal 9006, a sensor 9007 (the sensor has the function of measuring the following factors: force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electricity, radiation, flow, humidity, inclination, vibration, smell or infrared), a microphone 9008, etc.

[0566] FIG. 17A to FIG. 17G The electronic device shown has various functions. For example, it may have the following functions: a function of displaying various information (static images, dynamic images, or text images, etc.) on a display unit; a function of a touch panel; a function of displaying a calendar, date, or time, etc.; a function of being controlled and processed by various software (programs); a function of wireless communication; a function of reading out programs or data stored in a storage medium and processing them; etc.

[0567] Below, we explain in detail FIG. 17A to FIG. 17G Electronic equipment shown.

[0568] Fig.17A 9171 is a perspective view showing a portable information terminal 9171. The portable information terminal 9171 can be used as a smart phone, for example. Note that a speaker 9003, a connection terminal 9006, a sensor 9007, and the like can also be provided in the portable information terminal 9171. In addition, as the portable information terminal 9171, text or image information can be displayed on multiple surfaces. Fig.17A 9050. In addition, information 9051 indicated by a dotted rectangle may be displayed on another surface of the display unit 9001. Examples of information 9051 include information indicating that an email, SNS, or phone call has been received; a title of the email or SNS; a sender's name of the email or SNS; a date; a time; a remaining battery level; and radio wave strength. Alternatively, icon 9050 may be displayed at a location where information 9051 is displayed.

[0569] Fig. 17B 9172. The portable information terminal 9172 has a function of displaying information on three or more surfaces of the display unit 9001. Here, an example is shown in which information 9052, information 9053, and information 9054 are displayed on different surfaces. For example, when the portable information terminal 9172 is placed in a jacket pocket, the user can check the information 9053 displayed at a position viewed from above the portable information terminal 9172.

[0570] Fig. 17C9173 is a perspective view showing a tablet terminal 9173. The tablet terminal 9173 can execute various application software such as mobile phone, reading and editing of e-mails and articles, playing music, network communication, computer games, etc. The tablet terminal 9173 includes a display portion 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front of the housing 9000, an operation key 9005 used as an operation button on the left side of the housing 9000, and a connection terminal 9006 on the bottom.

[0571] Fig.17D 9001 is a stereoscopic diagram showing a watch-type portable information terminal 9200. The portable information terminal 9200 can be used, for example, as a smart watch (registered trademark). In addition, the display surface of the display unit 9001 is curved, and a display can be performed along its curved display surface. In addition, the portable information terminal 9200 can perform hands-free calls, for example, by communicating with a headset capable of wireless communication. In addition, by using the connection terminal 9006, the portable information terminal 9200 can perform data transmission or charging with other information terminals. Charging can also be performed by wireless power supply.

[0572] FIG. 17E to FIG. 17G 9201 is a perspective view showing a foldable portable information terminal. Fig.17E is a perspective view of the portable information terminal 9201 in an unfolded state. Figure 17G This is a three-dimensional diagram of the folded state. Fig.17F is from Fig.17E Status and Figure 17G The portable information terminal 9201 is easy to carry in the folded state, and has a large display area that is seamlessly spliced ​​in the unfolded state, so the display is easy to browse. The display unit 9001 included in the portable information terminal 9201 is supported by three housings 9000 connected by hinges 9055. The display unit 9001 can be bent within a range of a curvature radius of 0.1 mm or more and 150 mm or less, for example.

[0573] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when a plurality of configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate. Example 1

[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 (abbreviated as: Fr(2)F(4)A(βN2)B) represented by structural formula (162) in the embodiment is described. The structural formula of Fr(2)F(4)A(βN2)B is shown below.

[0575] [Chemical formula 108]

[0576] <Step 1: Synthesis of N-(chlorophenyl-4-yl)dibenzofuran-2-amine> Place 4.2 g (4.0 mmol) of 4-chloroaniline and 10 g (40 mmol) of 2-bromodibenzofuran in a 500 mL three-necked flask. Replace the air in the flask with nitrogen, then add 7.8 g (81 mmol) of sodium tert-butoxide and 202 mL of toluene. Stir the mixture under reduced pressure to deaerate. Add 2.4 mL (0.81 mmol) of tri(tert-butyl)phosphine (10 wt% hexane solution) to the mixture, heat to 60°C and stir. After stirring, add 0.23 g (0.40 mmol) of bis(dibenzylideneacetone)palladium (0), heat to 120°C and stir for 1 hour. After stirring, the reaction solution was filtered through alumina, diatomaceous earth (Fujifilm Wako Pure Chemical Industries, Ltd., catalog number: 537-02305), and magnesium silicate (Fujifilm Wako Pure Chemical Industries, Ltd., catalog number: 066-05265). The solid obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane: toluene = 9:1) to obtain 5.4 g of a light yellow solid containing the target substance. Hexane was added to an ethyl acetate solution of the obtained solid, and the precipitated solid was collected by filtration to obtain 5.2 g of the target substance as a white solid with a yield of 44%. The synthesis scheme of step 1 is shown below (s1-1). In addition, Fig.29A and Fig.29B The white solid 1 H NMR measurement results. In addition, Fig.29B Is magnification Fig.29A The graph shows that the concentration of N-(chlorophenyl-4-yl)dibenzofuran-2-amine is within the range of 5.5 ppm to 7.8 ppm.

[0577] [Chemical formula 109]

[0578] <Step 2: Synthesis of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-2-amine> In a 300 mL three-necked flask, place 5.0 g (17 mmol) of N-(chlorophenyl-4-yl)dibenzofuran-2-amine synthesized by step 1 and 4.7 g (17 mmol) of 4-bromo-9,9'-dimethylfluorene. Replace the air in the flask with nitrogen, and then add 3.3 g (34 mmol) of sodium tert-butoxide and 85 mL of toluene. Stir the mixture under reduced pressure to deaerate. Add 1.0 mL (0.34 mmol) of tri(tert-butyl)phosphine (10 wt% hexane solution) to the mixture, heat to 60°C and stir. After stirring, add 98 mg (0.17 mmol) of bis(dibenzylideneacetone)palladium(O), heat to 120°C and stir for 1 hour. After stirring, the reaction solution was filtered through alumina, diatomaceous earth (Fujifilm Wako Pure Chemical Industries, Ltd., catalog number: 537-02305), and magnesium silicate (Fujifilm Wako Pure Chemical Industries, Ltd., catalog number: 066-05265). The solid obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane), thereby obtaining 4.5 g of the target white solid with a yield of 65%. The synthesis scheme of step 2 (s1-2) is shown below. In addition, Fig. 30A and Fig. 30B The white solid 1 HNMR measurement results. In addition, Fig. 30B Is magnification Fig. 30A The figure shows that the concentration of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-2-amine was obtained.

[0579] [Chemical formula 110]

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

[0581] [Chemical formula 111]

[0582] 1.4 g of the obtained solid was purified by sublimation by gradient sublimation. In the sublimation purification, the solid was heated at 310° C. for 45 hours under the conditions of argon flowing at a flow rate of 10 mL / min and a pressure of 2.3 Pa. After sublimation purification, 910 mg of the target solid was obtained at a recovery rate of 65%.

[0583] Fig.19A , Fig.19B The following shows the obtained solid 1 H NMR measurement results. In addition, Fig.19B Is magnification Fig.19A This is a graph showing the range of 7.00 ppm to 8.25 ppm in FIG. 1. As can be seen from this, Fr(2)F(4)A(βN2)B was obtained in this synthesis example.

[0584] 1 H NMR (dichloromethane-d 2, 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 referred to as “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] In the measurement of the absorption spectrum, an ultraviolet visible spectrophotometer (V-770DS manufactured by JASCO Corporation) was used. In addition, a fluorescence spectrophotometer (FP-8600DS manufactured by JASCO Corporation) was used to measure the PL spectrum.

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

[0588] The absorption spectrum and PL spectrum of the thin film were measured using a sample in which FrFA(βN2)B was deposited on a quartz substrate by vacuum evaporation and a quartz substrate was used as a counter substrate for sealing. In addition, the PL spectrum was measured for the sealed sample, and the absorption spectrum was measured for the sample in which the counter substrate was removed by peeling off the seal. The absorption spectrum was obtained by subtracting the absorption spectrum of the quartz substrate from the absorption spectrum of FrFA(βN2)B deposited on the quartz substrate.

[0589] Fig. 20A The measurement results of toluene solution are shown. Fig. 20BThe measurement results of the thin film are shown. From the measurement results, it can be seen that the toluene solution of Fr(2)F(4)A(βN2)B has an absorption spectrum peak (absorption peak) near 360nm, and the thin film of Fr(2)F(4)A(βN2)B has an absorption peak near 361nm. No absorption band on the longer wavelength side than 430nm is observed in the toluene solution and the thin film. Therefore, when Fr(2)F(4)A(βN2)B is used in a light-emitting device, it can be used appropriately because the light-emitting efficiency does not decrease due to absorption at the wavelength of light used for display. In addition, the toluene solution of Fr(2)F(4)A(βN2)B has an emission wavelength peak near 418nm (excitation wavelength: 359nm), and the thin film of Fr(2)F(4)A(βN2)B has an emission spectrum peak (luminescence peak) near 441nm (excitation wavelength: 369nm). The HOMO level and LUMO level of Fr(2)F(4)A(βN2)B were calculated by cyclic voltammetry (CV) measurement. The calculation method is shown below.

[0590] As a measuring device, an electrochemical analyzer (ALS model 600A or 600C manufactured by BAS Co., Ltd.) was used. In the solution for CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (abbreviated as: n-Bu 4 NClO 4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) was dissolved at a concentration of 100 mmol / L, and the object to be measured was dissolved at a concentration of 2 mmol / L.

[0591] In addition, a platinum electrode (manufactured by BAS Inc., PTE platinum electrode) was used as a working electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 (5 cm)) was used as an auxiliary electrode, and an Ag / Ag electrode was used as a reference electrode. +Electrode (manufactured by BAS Inc., RE7 non-aqueous solvent type reference electrode). In addition, the measurement is carried out at room temperature (above 20°C and below 25°C). The scanning speed during CV measurement is unified to 0.1V / sec, and the oxidation potential Ea[V] and reduction potential Ec[V] relative to the reference electrode are measured. Ea is the middle potential of the oxidation-reduction wave, and Ec is the middle potential of the reduction-oxidation wave. Here, it is known that the potential energy of the reference electrode used in this embodiment relative to the vacuum energy level is -4.94[eV], so the HOMO energy level [eV] = -4.94-Ea, LUMO energy level [eV] = -4.94-Ec can be used to calculate the HOMO energy level and the LUMO energy level respectively.

[0592] Furthermore, CV measurement was repeated 100 times, and the oxidation-reduction wave in the measurement of the 100th cycle was compared with the oxidation-reduction wave in the measurement of the 1st cycle to investigate the electrical stability of the compound.

[0593] From this result, it can be seen that in the measurement of the oxidation potential Ea [V] of Fr(2)F(4)A(βN2)B, the HOMO energy level is -5.51 eV. On the other hand, in the measurement of the reduction potential Ec [V], it can be seen that the LUMO energy level is -2.45 eV. In addition, by comparing the waveforms after the first cycle and the 100th cycle in the repeated measurement of the oxidation-reduction wave, 92% of the peak intensity is maintained in the Ea measurement, and 99% of the peak intensity is maintained in the Ec measurement, which shows that Fr(2)F(4)A(βN2)B has excellent resistance to repeated oxidation and repeated reduction.

[0594] In addition, differential scanning calorimetry (DSC measurement) of Fr(2)F(4)A(βN2)B was performed using DSC8500 manufactured by PerkinElmer, Inc. In the differential scanning calorimetry, the following operation was performed twice in succession: the temperature was raised from -10°C to 320°C at a heating rate of 40°C / min, the temperature was maintained for 3 minutes, and then the temperature was cooled to -10°C at a cooling rate of 40°C / min, and then the temperature was maintained for 3 minutes. From the DSC measurement results of the second cycle, it can be seen that the glass transition point (Tg) of Fr(2)F(4)A(βN2)B is 133°C, and the crystallization temperature and melting point are not observed. Therefore, it can be seen that Fr(2)F(4)A(βN2)B is a substance with very high heat resistance and can maintain a thermally stable film quality.

[0595] Fr(2)F(4)A(βN2)B was subjected to thermogravimetry-differential thermal analysis (TG-DTA). A high-sensitivity differential thermogravimetric analyzer (STA2500Regulus manufactured by NETZSCH Japan Co., Ltd.) was used for the measurement. The measurement was performed under the conditions of atmospheric pressure, a heating rate of 10°C / min, and a nitrogen flow (flow rate of 200 mL / min). From the results of the thermogravimetric-differential thermal analysis, it can be seen that the temperature (decomposition temperature) at which the weight obtained from the thermogravimetric measurement becomes -5% of the weight at the start of the measurement is 472°C or above, indicating that Fr(2)F(4)A(βN2)B has high heat resistance. Example 2

[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-fluorene-2-yl)dibenzofuran-4-amine (abbreviated as: FrFA(βN2)B) represented by structural formula (152) in the embodiment is described. The structural formula of FrFA(βN2)B is shown below.

[0597] [Chemical formula 112]

[0598] <Step 1: Synthesis of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine> In a 200mL three-necked flask, 4.8g (13.1mmol) of N-(4-bromophenyl)-9,9-dimethyl-9H-fluorene-2-amine, 5.0g (13.1mmol) of 2-[(2,2'-binaphthyl)-6-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborane, 160mg of tri(o-tolyl)phosphine, 5.5g of potassium carbonate, 40mL of toluene, 10mL of ethanol, and 10mL of pure water were placed. Stir under reduced pressure to degas, then heat to 60°C and stir 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, then filtered and washed with ethanol to obtain 6.0g of gray-brown solid. The gray-brown solid was dissolved in dichloromethane and gravity filtered to obtain 5.1g of yellow solid. The yellow solid was dissolved in hot toluene, and then the solution was cooled to room temperature and recrystallized to obtain 4.4 g of the target thin yellow solid with a yield of 63%. The synthesis scheme (s2-1) of step 1 is shown below. In addition, Fig.31A and Fig.31B The yellow solid 1H NMR measurement results. In addition, Fig.31B Is magnification Fig.31A The above graph shows that the concentration of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine was obtained.

[0599] [Chemical formula 113]

[0600] <Step 2: Synthesis of FrFA(βN2)B> In a 50 mL three-necked flask, 1.0 g (1.8 mmol) of N-[4-(2,2'-binaphthyl-6-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine and 500 mg (1.8 mmol) of 4-bromodibenzofuran were placed. The air in the flask was replaced with nitrogen, and then 360 mg (3.7 mmol) of sodium tert-butoxide and 18 mL of toluene were added. The mixture was stirred under reduced pressure to deaerate. 37 μL (37 μmol) of tri(tert-butyl)phosphine (10 wt% hexane solution) was added dropwise to the mixture, the temperature was raised to 60°C and stirred, and then 11 mg (18 μmol) of bis(dibenzylideneacetone)palladium (0) was added and stirred at 120°C for 1 hour. After stirring, the reaction solution was filtered through alumina, diatomaceous earth (Fujifilm Wako Pure Chemical Industries, Ltd., catalog number: 537-02305), and magnesium silicate (Fujifilm Wako Pure Chemical Industries, Ltd., catalog number: 066-05265). The solid obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane: toluene = 7: 1) to obtain 675 mg of the target white solid at a yield of 52%. The synthesis scheme of step 2 (s2-2) is shown below.

[0601] [Chemical formula 114]

[0602] 0.67 g of the obtained solid was sublimated and purified by gradient sublimation. In the sublimation purification, the solid was heated at 295° C. for 20 hours under the conditions of argon flowing at a flow rate of 8.0 mL / min and a pressure of 2.9 Pa. After sublimation purification, 0.33 g of the target solid was obtained at a recovery rate of 49%.

[0603] Fig.21A , Fig. 21B The solid obtained is shown below 1 H NMR measurement results. Fig. 21B Is magnification Fig.21AThis is a graph showing the range of 7.00 ppm to 8.30 ppm in FIG. 1. As can be seen from this, FrFA(βN2)B was obtained in this synthesis example.

[0604] 1 H NMR (dichloromethane-d 2 , 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 in the same manner as in Example 1.

[0606] Fig.22A Shows the measurement results of the solution, Fig. 22B The measurement results of the thin film are shown. From the measurement results, it can be seen that the absorption peak of the toluene solution of FrFA(βN2)B is observed near 362nm, and the absorption peak of the thin film of FrFA(βN2)B is observed near 365nm, and no absorption band is observed on the side with a wavelength longer than 440nm. It can be seen that when FrFA(βN2)B is used in a light-emitting device, the luminous efficiency will not be reduced due to absorption at the wavelength of light used for display, so it can be used appropriately. In addition, the peak of the luminous wavelength of the toluene solution of FrFA(βN2)B is observed near 422nm (excitation wavelength: 366nm), and the luminous peak of the thin film of FrFA(βN2)B is observed near 444nm (excitation wavelength: 365nm).

[0607] The HOMO energy level and LUMO energy level of FrFA (βN2) were calculated by cyclic voltammetry (CV) measurement. The calculation method is the same as in Example 1. From the results, it can be seen that in the measurement of the oxidation potential Ea [V] of FrFA (βN2), the HOMO energy level is -5.47 eV. On the other hand, in the measurement of the reduction potential Ec [V], the LUMO energy level is -2.47 eV. In addition, by comparing the waveforms after the first cycle and the 100th cycle in the repeated measurement of the oxidation-reduction wave, it can be seen that 96% of the peak intensity is maintained in the Ea measurement, and 98% of the peak intensity is maintained in the Ec measurement. FrFA (βN2) has excellent resistance to repeated oxidation and repeated reduction.

[0608] In addition, FrFA (βN2) was subjected to DSC measurement. The measurement was performed in the same manner as in Example 1. From the DSC measurement results of the second cycle, it can be seen that the glass transition point of FrFA (βN2) is 128°C, and no crystallization temperature or melting point is observed. This shows that FrFA (βN2) is a substance with very high heat resistance and can maintain a thermally stable film quality.

[0609] In addition, TG-DTA was performed on FrFA (βN2). The measurement was performed in the same manner as in Example 1. From the results, it was found that the decomposition temperature of FrFA (βN2) was 460° C. or higher, and that FrFA (βN2) was a substance having high heat resistance. Example 3

[0610] In this example, a light-emitting device according to one embodiment of the present invention is described in detail. The structural formulas of typical organic compounds used in this example are shown below.

[0611] [Chemical formula 115]

[0612] (Method for manufacturing light emitting device) First, indium tin oxide containing silicon oxide (ITSO) was deposited to a thickness of 110 nm on a glass substrate by a sputtering method, thereby forming the first electrode 101. Note that 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, the substrate is placed inside the chamber and the pressure is reduced to 1×10 -4 Pa in a vacuum deposition apparatus and in a heating chamber in the vacuum deposition apparatus, vacuum baking is performed at 170° C. for 30 minutes, and then the substrate is cooled for about 30 minutes.

[0615] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzofuran-4-amine (abbreviation: FrFA(βN2)B) represented by the above structural formula (i) and an electron acceptor material containing fluorine with a molecular weight of 672 (OCPD-003) are co-evaporated on the first electrode 101 by a resistance heating evaporation method in a weight ratio of 1:0.1 (=FrFA(βN2)B:OCPD-003) and a thickness of 10 nm, thereby forming a hole injection layer 111.

[0616] Next, FrFA(βN2)B was evaporated on 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 (abbreviated as DBfBB1TP) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form a second hole transport layer, thereby forming a hole transport layer 112. In addition, the second hole transport layer is also used as an electron blocking layer.

[0617] Next, on the hole transport layer 112, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviated as αN-βNPAnth) represented by the above structural formula (iii) and 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10PCA2Nbf(IV)-02) represented by the above structural formula (iv) are co-deposited in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) with a thickness of 25 nm, thereby forming a light-emitting layer 113.

[0618] Then, 2-[3'-(9,9-dimethyl-9H-fluorene-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviated as: mFBPTzn) represented by the above structural formula (v) is deposited in a thickness of 10 nm on the light-emitting layer 113 to form a first electron transport layer, and then 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviated as: mPPhen2P) represented by the above structural formula (vi) is deposited in a thickness of 15 nm to form a second electron transport layer, thereby forming an electron transport layer 114.

[0619] Lithium fluoride was deposited on the electron transport layer 114 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 the second electrode 102 , thereby manufacturing a light-emitting device according to one embodiment of the present invention.

[0621] The element structure of the above-mentioned light emitting device is shown below.

[0622] [Table 1]

[0623] In a glove box with a nitrogen atmosphere, each of the light-emitting devices was sealed using a glass substrate in such a manner that the light-emitting devices were not exposed to the atmosphere (the sealing material was applied around the element, UV treatment was performed during sealing, and heat treatment was performed at 80°C for 1 hour), and then the initial characteristics of the light-emitting devices were measured.

[0624] Fig.23 The brightness-current density characteristics of the light emitting device are shown. Fig.24 The current efficiency-brightness characteristics are shown. Fig.25 The brightness-voltage characteristics are shown. Fig.26 The current density-voltage characteristics are shown. Fig. 27 The external quantum efficiency-brightness characteristics are shown. Fig.28 In addition, Table 2 shows the electroluminescence spectrum of the light emitting device at 1000 cd / m 2 Main characteristics near. Note that the brightness, CIE chromaticity and emission spectrum were measured at room temperature using a spectroradiometer (manufactured by Topcon, SR-UL1R). In addition, by using the measured brightness and emission spectrum, the external quantum efficiency was calculated under the assumption that the light distribution characteristics were Lambertian.

[0625] [Table 2]

[0626] Depend on Figure 23 to Figure 28 As can be seen from Table 2, the light-emitting device according to one embodiment of the present invention is a light-emitting device having excellent characteristics. Example 4

[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 (abbreviated as Fr(2)FA(βN2)B) represented by structural formula (153) in Embodiment 1 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 1 The values ​​of H NMR, Fig.32A and Fig.32BShow 1 H NMR spectrum. In addition, Fig.32B Is magnification Fig.32A The graph shows the range of 7.00 ppm to 8.40 ppm in FIG. 1. Thus, Fr(2)FA(βN2)B was obtained.

[0628] [Chemical formula 116]

[0629] [Chemical formula 117]

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

[0631] The table below shows the results of measuring the physical properties of Fr(2)FA(βN2)B. In addition, the physical properties were measured in the same manner as in Example 1. As a result, Fr(2)FA(βN2)B has no absorption band observed on the longer wavelength side than 440nm, and does not cause a decrease in the luminous efficiency of the light-emitting device due to absorption in the visible light wavelength region, so it can be used appropriately. In addition, it is found that the material has high heat resistance.

[0632] [Table 3] Example 5

[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 (abbreviated as: FrF(4)A(βN2)B) represented by structural formula (157) in Embodiment 1 was synthesized. The structural formula of FrF(4)A(βN2)B is shown below.

[0634] [Chemical formula 118]

[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. In addition, the obtained white solid was measured. 1 H NMR. The following shows 1 The values ​​of H NMR, Fig.33A and Fig.33B Show 1 H NMR spectrum. In addition, Fig.33B Is magnification Fig.33A This is a graph showing the range of 6.60 ppm to 8.00 ppm in the present invention. It can be seen that N-(chlorophenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-4-yl)dibenzofuran-4-amine is obtained in this step.

[0636] [Chemical formula 119]

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

[0638] <Step 2: Synthesis of FrF(4)A(βN2)B> In a 200 mL three-necked 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'-binaphthyl-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 placed. The mixture was stirred and degassed under reduced pressure, and then heated to 60° C., and then 56 mg of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (abbreviated as: PEPPSI) was added. TM -IPr), heated to 90°C and stirred for 1 hour. After stirring, cooled to room temperature, concentrated the reaction mixture, and filtered with hot toluene. The yellow solid obtained by concentrating the filtrate was dissolved in toluene, and then ethanol was added for recrystallization to obtain 2.1 g of the target light yellow solid with a yield of 74%. The synthesis scheme of step 2 (s4-2) is shown below. In addition, the light yellow solid obtained was measured. 1 H NMR. The following shows 1 The values ​​of H NMR, Fig.34A and Fig.34B Show 1 HNMR diagram. In addition, Fig.34B Is magnification Fig.34A This is a graph showing the range of 6.60 ppm to 8.40 ppm in FIG. 1. It can be seen that FrF(4)A(βN2)B is obtained in this step.

[0639] [Chemical formula 120]

[0640] 1 H NMR (dichloromethane-d 2 , 500MHz, 20℃): δ=8.17 (d, J=9.0Hz, 2H), δ=8.03 (s, 1H), δ=7.99-7.86 (m, 8H), δ=7.77 (d, J=7.5Hz, 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 = 7.5Hz, 1.0Hz, 1H), δ = 6.92 (d, J = 9Hz, 2H), δ = 1.51 (s, 6H)

[0641] The following table shows the results of measuring the physical properties of FrF(4)A(βN2)B. In addition, the physical properties were measured in the same manner as in Example 1. As a result, FrF(4)A(βN2)B has no absorption band observed on the longer wavelength side than 440nm, and does not cause a decrease in the luminous efficiency of the light-emitting device due to absorption in the visible light wavelength region, so it can be used appropriately. In addition, it is found that the material has high heat resistance.

[0642] [Table 4] Example 6

[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 (abbreviated as Fr(1)FA(βN2)B) represented by structural formula (154) in Embodiment 1 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 values ​​of H NMR, Fig.35A , Fig.35B Show 1 H NMR spectrum. In addition, Fig.35B Is magnification Fig.35A This shows that Fr(1)FA(βN2)B was obtained in this synthesis example.

[0644] [Chemical formula 121]

[0645] [Chemical formula 122]

[0646] 1 H NMR (dichloromethane-d 2, 500MHz, 20℃): δ=8.19 (s, 2H), δ=8.07 (d, J=1.5Hz, 1H), δ=7.99-7.87 (m, 7H), δ=7.79 (dd , J=8.5Hz, 2.0Hz, 1H), δ=7.67 (dt, J=9.0Hz, 5.0Hz, 2H), δ=7.61 (d, J=7.5Hz, 1H), δ=7.58 ( d, J=8.5Hz, 1H), δ=7.53-7.44 (m, 5H), δ=7.37 (d, J=7.0Hz, 1H), δ=7.34-7.21 (m, 7H), δ=7. 14-7.11 (m, 1H), δ = 7.05 (dd, J = 8.0Hz, 2.0Hz, 1H), δ = 7.00 (t, J = 2.5Hz, 1H), δ = 1.35 (s, 6H)

[0647] The following table shows the results of measuring the physical properties of Fr(1)FA(βN2)B. In addition, the physical properties were measured in the same manner as in Example 1. As a result, Fr(1)FA(βN2)B has no absorption band observed on the longer wavelength side than 440nm, and does not cause a decrease in the luminous efficiency of the light-emitting device due to absorption in the visible light wavelength region, so it can be used appropriately. In addition, it is found that the material has high heat resistance.

[0648] [Table 5] Example 7

[0649] <<Synthesis example 6>> In this synthesis example, N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9'-diphenyl-9H-fluorene-2-yl)dibenzofuran-2-amine (abbreviated as: Fr(2)FLP(2)A(βN2)B) represented by structural formula (123) in Embodiment 1 was synthesized. The structural formula of Fr(2)FLP(2)A(βN2)B is shown below.

[0650] [Chemical formula 123]

[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. In addition, the obtained white solid was measured. 1 H NMR, shown below 1 The values ​​of H NMR, Fig.36A and Fig.36B Show1 H NMR spectrum. In addition, Fig.36B Is magnification Fig.36A This shows that N-(chlorophenyl-4-yl)-N-(9,9-diphenyl-9H-fluorene-2-yl)dibenzofuran-2-amine is obtained in this step.

[0652] [Chemical formula 124]

[0653] 1 H NMR (dichloromethane-d 2 , 500MHz, 20℃): δ=7.76 (d, J=7.5Hz, 1H), δ=7.67 (d, J=8.5Hz, 1H), δ=7.66 (d, J=2.5 Hz, 1H), δ=7.62 (d, J=8.0Hz, 1H), δ=7.54 (d, J=8.0Hz, 1H), δ=7.45-7.42 (m, 2H), δ= 7.34-7.27 (m, 3H), δ=7.20 (d, J=7.5Hz, 1H), δ=7.18-7.14 (m, 9H), δ=7.13 (d, J=2.0 Hz, 1H), δ=7.10-7.08 (m, 4H), δ=7.01 (dd, J=8.5Hz, 2.0Hz, 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 of step 2 is shown below (s6-2). In addition, the obtained solid was measured. 1 H NMR, shown below 1 The values ​​of H NMR, Fig.37A and Fig.37B Show 1 H NMR spectrum. In addition, Fig.37B Is magnification Fig.37A This shows that Fr(2)FLP(2)A(βN2)B was obtained in this synthesis example.

[0655] [Chemical formula 125]

[0656] 1 H NMR (dichloromethane-d 2, 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 = 2.5Hz, 2H), δ = 7.70 (d, J = 7.5Hz, 1H), δ = 7.65 (d, J =8.0Hz, 1H), δ=7.62 (d, J=7.0Hz, 2H), δ=7.55 (d, J=8.0Hz, 1H), δ=7.53-7.43 (m, 4H), δ=7.36-7.25 (m, 5H), δ=7.22 (d, J=7.0Hz, 1H), δ=7.19-7.10 (m, 12H)

[0657] The table below shows the results of measuring the physical properties of Fr(2)FLP(2)A(βN2)B. In addition, the physical properties were measured in the same manner as in Example 1. As a result, Fr(2)FLP(2)A(βN2)B had no absorption band observed on the longer wavelength side than 440nm, and the luminous efficiency of the light-emitting device did not decrease due to absorption in the visible light wavelength region, so it can be used appropriately. In addition, it was found that the material has high heat resistance.

[0658] [Table 6] Example 8

[0659] <<Synthesis example 7>> In this synthesis example, N-[4-(2,2'-binaphthyl-6-yl)phenyl]-N-(9,9'-diphenyl-9H-fluorene-2-yl)dibenzofuran-4-amine (abbreviated as: FrFLP(2)A(βN2)B) represented by structural formula (148) in Embodiment 1 was synthesized. The structural formula of FrFLP(2)A(βN2)B is shown below.

[0660] [Chemical formula 126]

[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. In addition, the obtained white solid was measured. 1 H NMR, shown below 1 The values ​​of H NMR, Fig.38A and Fig.38B Show 1 H NMR spectrum. In addition, Fig.38B Is magnification Fig.38A This shows that N-(chlorophenyl-4-yl)-N-(9,9-diphenyl-9H-fluorene-2-yl)dibenzofuran-4-amine is obtained in this step.

[0662] [Chemical formula 127]

[0663] 1 H NMR (dichloromethane-d 2 , 500MHz, 20℃): δ=7.98 (d, J=7.5Hz, 1H), δ=7.78 (dd, J=7.5Hz, 1.0Hz, 1H), δ=7.72 (d, J=7.5Hz, 1H), δ=7. 68 (d, J=8.5Hz, 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 of step 2 is shown below (s7-2). In addition, the obtained solid was measured. 1 H NMR, shown below 1 The values ​​of H NMR, Fig.39A and Fig.39B Show 1 H NMR spectrum. In addition, Fig.39B Is magnification Fig.39A This shows that FrFLP(2)A(βN2)B was obtained in this synthesis example.

[0665] [Chemical formula 128]

[0666] 1 H NMR (dichloromethane-d 2, 500MHz, 20℃): δ=8.20 (s, 2H), δ=8.06 (s, 1H), δ=8.00-7.87 (m, 8H), δ=7.78 (d, J=7.0Hz, 2H), δ=7.71 (d, J=7.5Hz, 1H), δ=7.69 ( d, J=8.0Hz, 1H), δ=7.62 (d, J=9.0Hz, 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 following table shows the results of measuring the physical properties of FrFLP(2)A(βN2)B. In addition, the physical properties were measured in the same manner as in Example 1. As a result, FrFLP(2)A(βN2)B had no absorption band observed on the longer wavelength side than 440nm, and the luminous efficiency of the light-emitting device did not decrease due to absorption in the visible light wavelength region, so it can be used appropriately. In addition, it was found that the material has high heat resistance.

[0668] [Table 7] Example 9

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

[0670] [Chemical formula 129]

[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. In addition, the obtained solid was measured. 1 H NMR, shown below 1 The values ​​of H NMR, Fig.40A and Fig.40B Show 1 H NMR spectrum. In addition, Fig.40B Is magnification Fig.40A This is a graph showing the range of 6.80 ppm to 8.40 ppm in the above-mentioned graph. It can be seen from this that FrSFA(βN2)B was obtained in this synthesis example.

[0672] [Chemical formula 130]

[0673] 1 H NMR (dichloromethane-d 2 , 500MHz, 20℃): δ=8.18 (d, 6.5Hz, 2H), δ=8.01 (s, 1H), δ=7.98-7.87 (m, 8H), δ=7.77 (t, J=8.0Hz, 2H), δ=7. 74-7.68 (m, 4H), δ=7.54-7.47 (m, 4H), δ=7.38 (t, J=7.0Hz, 1H), δ=7.33 (d, J=9.5Hz, 1H), δ=7.31 (t, J=8.5H z, 2H), δ=7.25 (t, J=7.5Hz, 2H), δ=7.19 (t, J=7.5Hz, 1H), δ=7.18 (dd, J=8.5Hz, 2.0Hz, 1H), δ=7.13 (d, J=7 .5Hz, 1H), δ=7.04-6.97 (m, 5H), δ=6.73 (d, J=8.5Hz, 2H), δ=6.58 (d, J=7.5Hz, 1H), δ=6.51 (d, J=2.0Hz, 1H)

[0674] The table below shows the results of measuring the physical properties of FrSFA (βN2) B. In addition, the physical properties were measured in the same manner as in Example 1. As a result, FrSFA (βN2) B has no absorption band observed on the side of wavelengths longer than 440 nm, and does not reduce the luminous efficiency of the light-emitting device due to absorption in the wavelength region of visible light, so it can be used appropriately. In addition, it is known that the material has high heat resistance.

[0675] [Table 8]

Claims

1. An organic compound represented by the general formula (G1): in, X represents a sulfur atom or an oxygen atom, R 1 To R 22 each independently represents any one of hydrogen, halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted linear alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, R 16 To R 22 At least one of represents a substituted or unsubstituted naphthyl group, n represents an integer from 0 to 4, Ar 1 Represented by the general formula (g1-1) or the general formula (g1-2): R 23 To R 30 Any one or R 33 To R 48 Any one of is bonded to the nitrogen of the amine, In addition, R 31 and R 32 Each independently represents any one of hydrogen, halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms. The organic compound according to claim 1 , wherein n is 0 or 1.

3. The organic compound according to claim 1, wherein when n is 2 or more, a plurality of R 12 Same as each other, multiple R 13 Same as each other, multiple R 14 are identical to each other, and multiple R 15 The same as each other.

4. The organic compound according to claim 1, The organic compound is represented by the general formula (G2): And R 16 To R 19 At least one of represents a substituted or unsubstituted naphthyl group.

5. The organic compound according to claim 1, The organic compound is represented by the general formula (G3): And R 16 To R 22 At least one of represents a substituted or unsubstituted naphthyl group.

6. The organic compound according to claim 1, Wherein R 16 To R 22 Any one of them is represented by the general formula (g2): And R 49 To R 55 Each independently represents any one of hydrogen, halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.

7. An organic semiconductor device comprising the organic compound according to claim 1.

8. A light emitting device comprising the organic compound according to claim 1.

9. An electronic device comprising the organic semiconductor device according to claim 7.

10. An organic compound represented by the general formula (G4): in, X represents a sulfur atom or an oxygen atom, R 1 To R 11 , R 16 , R 17 , R 19 To R 22 and R 49 To R 55 each independently represents any one of hydrogen, halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted linear alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, Ar 1 Represented by the general formula (g1-1) or the general formula (g1-2): R 23 To R 30 Any one or R 33 To R 48 Any one of is bonded to the nitrogen of the amine, In addition, R 31 and R 32 Each independently represents any one of hydrogen, halogen, nitrile, substituted or unsubstituted alkenyl, substituted or unsubstituted vinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted straight-chain alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.

11. The organic compound according to claim 10, The organic compound is represented by the general formula (G5):

12. The organic compound according to claim 10, The organic compound is represented by the general formula (G6): 。 13. An organic semiconductor device comprising the organic compound according to claim 10.

14. A light emitting device comprising the organic compound according to claim 10.

15. An electronic device comprising the organic semiconductor device according to claim 13.

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