Organic compound

Abstract

To provide an organic compound which enables production of a light-emitting device having favorable hole transportability and high reliability.SOLUTION: There is provided an organic compound expressed by the general formula (G1) below. In the general formula (G1), one of R1 to R16 is a group represented by the general formula (g1). In the general formula (g1), Ar1 is a group represented by the general formula (Ar1-1), and Ar2 denotes a phenyl group or a phenyl group having at least one naphthyl group. In the general formula (Ar1-1), any one of R17 and R24 to R26 is a bonding hand, and X and Y independently represent an oxygen atom or a sulfur atom.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] One aspect 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 technical field. Examples of the technical field of one embodiment of the present invention include a compound, a light-emitting device, a semiconductor device, a display device, a light-emitting device, a power storage device, a memory device, an electronic device, a lighting device, an input device (for example, a touch sensor), an input / output device (for example, a touch panel), a driving method thereof, or a manufacturing method thereof. [Background technology]

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

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

[0005] Light-emitting devices using organic compounds (also called light-emitting elements) have been developed as display devices. Light-emitting devices using electroluminescence (hereinafter referred to as EL) (also called organic EL devices or light-emitting devices) have features such as being easily thin and lightweight, being capable of high-speed response to input signals, and being able to be driven by a DC constant voltage power supply, and are therefore used in display devices.

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

[0007] [Patent Document 1] Japanese Patent Application Publication No. 2023-99506 Summary of the Invention [Problem to be solved by the invention]

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

[0009] Another embodiment of the present invention has an object to provide a light-emitting device with low driving voltage. Another embodiment of the present invention has an object to provide a light-emitting device, a light-emitting apparatus, an electronic device, and a display device with low power consumption. Another embodiment of the present invention has an object to provide a light-emitting device with small voltage fluctuations due to driving. Another embodiment of the present invention has an object to provide a light-emitting device with long driving lifetime.

[0010] Note that the description of these problems does not preclude the existence of other problems. One embodiment of the present invention does not necessarily have to solve all of these problems. Problems other than these can be extracted from the description in the specification, drawings, and claims. [Means for solving the problem]

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

[0012] [ka]

[0013] In the general formula (G1), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms.

[0014] [ka]

[0015] In the group represented by general formula (g1), Ar 1 is represented by the following general formula (Ar 1 -1), and Ar 2 represents a substituted or unsubstituted phenyl group or a phenyl group having at least a substituted or unsubstituted naphthyl group. 1 ~R 16 It binds to one of the following:

[0016] [ka]

[0017] General formula (Ar 1 In the group represented by formula (1), Y represents an oxygen atom or a sulfur atom, and R 17 ~R 26 each independently represents any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, provided that R 17 , R 24 ~R 26 Any one of the above is a bond bonded to the nitrogen atom in general formula (g1).

[0018] Another aspect of the present invention is the above-mentioned structure, 2 is represented by the following structural formula (Ar 2 -1) to the following structural formula (Ar 2 -20) is an organic compound represented by the following structural formula (Ar 2 -1) to the following structural formula (Ar 2 -20), the asterisk indicates the bond to the nitrogen in general formula (g1).

[0019] [ka]

[0020] [ka]

[0021] Alternatively, another embodiment of the present invention is a compound represented by the general formula (g1) in the above structure, wherein R 6 ~R 8 and R 13 ~R 16 It is an organic compound that bonds to one of the following:

[0022] Alternatively, another aspect of the present invention is a compound represented by the general formula (Ar 1 -1) in the group represented by R 17 is an organic compound in which the bond bonded to the nitrogen atom of general formula (g1) is

[0023] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the group represented by General Formula (g1) is a group represented by General Formula (G1), 7 or R 15 It is an organic compound that binds to

[0024] Alternatively, another aspect of the present invention is a compound represented by the general formula (Ar 1 -1) in the group represented by R 17 is an organic compound in which the bond bonded to the nitrogen atom of general formula (g1) is

[0025] Another embodiment of the present invention is an organic compound represented by General Formula (G1).

[0026] [ka]

[0027] In the general formula (G1), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16is a group represented by general formula (g2), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms.

[0028] [ka]

[0029] In the group represented by general formula (g2), Ar 2 represents a substituted or unsubstituted phenyl group or a phenyl group having at least a substituted or unsubstituted naphthyl group, Y represents an oxygen atom or a sulfur atom, R 18 ~R 26 each independently represents any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. 1 ~R 16 It binds to one of the following:

[0030] In addition, Ar 2 When the phenyl group or naphthyl group in the formula (I) has a substituent, the substituent can be selected from an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aromatic hydrocarbon group having 1 to 12 carbon atoms and being unsubstituted or having 1 to 4 alkyl groups having 1 to 4 carbon atoms, and the multiple alkyl groups may be the same or different.

[0031] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device according to the present invention, wherein Ar 2 is represented by the following structural formula (Ar 2 -1) to the following structural formula (Ar 2 -20) is an organic compound represented by the following structural formula (Ar 2 -1) to the following structural formula (Ar 2 -20), the asterisk indicates the bond to the nitrogen in general formula (g2).

[0032] [ka]

[0033] [ka]

[0034] Alternatively, another embodiment of the present invention is a compound according to the above structure, wherein the group represented by general formula (g2) is R 6 ~R 8 and R 13 ~R 16 It is an organic compound that bonds to one of the following:

[0035] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the group represented by General Formula (g2) is a group represented by General Formula (G1), 7 or R 15 It is an organic compound that binds to

[0036] Another embodiment of the present invention is an organic electronic device including any of the organic compounds described above.

[0037] Another embodiment of the present invention is a light-emitting device including any of the above organic compounds.

[0038] Another embodiment of the present invention is a light-receiving device including any of the organic compounds described above.

[0039] Another embodiment of the present invention is an organic electronic device having a light-emitting device and a light-receiving device, each of which includes any of the organic compounds described above, on the same plane.

[0040] Another aspect of the present invention is an organic electronic device using any of the organic compounds described above in a capping layer.

[0041] Another aspect of the present invention is an electronic device including the organic electronic device.

[0042] Another embodiment of the present invention is a light-emitting device including an EL layer between a pair of electrodes, the EL layer including at least a light-emitting layer and a carrier-transport layer, and the carrier-transport layer including an organic compound represented by the following general formula (G0):

[0043] [ka]

[0044] In the general formula (G0), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms.

[0045] [ka]

[0046] In the group represented by general formula (g1), Ar 1is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted bisnaphthofuranyl group, or a substituted or unsubstituted bisnaphthothiophenyl group, and Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms, and the bond marked with an asterisk is R 1 ~R 16 It binds to one of the following:

[0047] Another embodiment of the present invention is a light-emitting device including an EL layer between a pair of electrodes, the EL layer including at least a light-emitting layer and a carrier-transport layer, and the light-emitting layer including an organic compound represented by the following general formula (G0):

[0048] [ka]

[0049] In the general formula (G0), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms.

[0050] [ka]

[0051] In the group represented by general formula (g1), Ar 1is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted bisnaphthofuranyl group, or a substituted or unsubstituted bisnaphthothiophenyl group, and Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms, and the bond marked with an asterisk is R 1 ~R 16 It binds to one of the following:

[0052] Another embodiment of the present invention is a light-emitting device including an EL layer between a pair of electrodes, the EL layer including at least a light-emitting layer and a carrier-transporting layer, and both the light-emitting layer and the carrier-transporting layer containing an organic compound represented by the following general formula (G0):

[0053] [ka]

[0054] In the general formula (G0), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms.

[0055] [ka]

[0056] In the group represented by general formula (g1), Ar1 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted bisnaphthofuranyl group, or a substituted or unsubstituted bisnaphthothiophenyl group, and Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms, and the bond marked with an asterisk is R 1 ~R 16 It binds to one of the following:

[0057] Another embodiment of the present invention is an organic semiconductor device including an EL layer between a pair of electrodes, the EL layer including at least a light-emitting layer and a carrier transport layer, the carrier transport layer not in contact with the carrier transport layer of an EL layer included in an adjacent light-emitting device formed on the same plane, and the carrier transport layer including an organic compound represented by the following general formula (G0):

[0058] [ka]

[0059] In the general formula (G0), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms.

[0060] [ka]

[0061] In the group represented by general formula (g1), Ar 1 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted bisnaphthofuranyl group, or a substituted or unsubstituted bisnaphthothiophenyl group, and Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms, and the bond marked with an asterisk is R 1 ~R 16 It binds to one of the following:

[0062] Another embodiment of the present invention is a light-emitting device including an EL layer between a pair of electrodes and a capping layer in contact with one of the electrodes, the one of the electrodes being an electrode through which light emitted from the EL layer is extracted, and the capping layer includes an organic compound represented by the following general formula (G0):

[0063] [ka]

[0064] In the general formula (G0), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms.

[0065] [ka]

[0066] In the group represented by general formula (g1), Ar 1 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted bisnaphthofuranyl group, or a substituted or unsubstituted bisnaphthothiophenyl group, and Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms, and the bond marked with an asterisk is R 1 ~R 16 It binds to one of the following:

[0067] Another embodiment of the present invention is an organic semiconductor device including an EL layer between a pair of electrodes, the EL layer including a first layer, and the first layer including an organic compound represented by the following general formula (G0) and a material having an acceptor property for the organic compound represented by the general formula (G0):

[0068] [ka]

[0069] In the general formula (G0), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms.

[0070] [ka]

[0071] In the group represented by general formula (g1), Ar 1 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted bisnaphthofuranyl group, or a substituted or unsubstituted bisnaphthothiophenyl group, and Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms, and the bond marked with an asterisk is R 1 ~R 16 It binds to one of the following:

[0072] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device according to the present invention, wherein Ar 1 is represented by the following general formula (Ar 1 -1), and Ar 2 is a substituted or unsubstituted phenyl group or a substituted phenyl group having a substituted or unsubstituted naphthyl group.

[0073] [ka]

[0074] General formula (Ar 1 In the group represented by formula (1), Y represents an oxygen atom or a sulfur atom, and R 17 ~R 26each independently represents any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, provided that R 17 , R 24 ~R 26 Any one of the above is a bond bonded to the nitrogen atom in general formula (G0).

[0075] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 2 is represented by the following structural formula (Ar 2 -1) to the following structural formula (Ar 2 -20) is an organic compound represented by any one of the groups.

[0076] [ka]

[0077] [ka]

[0078] However, the above structural formula (Ar 2 -1) to structural formula (Ar 2 -20), the asterisk indicates the bond to nitrogen in the general formula (GO).

[0079] Another embodiment of the present invention is a light-receiving device including a light-receiving layer between a pair of electrodes, the light-receiving layer including at least an active layer and a carrier-transporting layer, and the carrier-transporting layer including an organic compound represented by the following general formula (G0):

[0080] [ka]

[0081] In the general formula (G0), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms.

[0082] [ka]

[0083] In the group represented by general formula (g1), Ar 1 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted bisnaphthofuranyl group, or a substituted or unsubstituted bisnaphthothiophenyl group, and Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms, and the bond marked with an asterisk is R 1 ~R 16 It binds to one of the following:

[0084] Another embodiment of the present invention is a semiconductor device including the above-described light-receiving device and the light-emitting device on the same plane.

[0085] Another aspect of the present invention is a semiconductor device having the above-described light-receiving device and a light-emitting device on the same plane, the light-receiving device and the light-emitting device sharing a carrier transport layer. [Effects of the Invention]

[0086] According to one embodiment of the present invention, a novel organic compound can be provided. Alternatively, according to one embodiment of the present invention, a novel carrier-transporting material can be provided. Alternatively, according to one embodiment of the present invention, a novel hole-transporting material can be provided. Alternatively, according to one embodiment of the present invention, a carrier-transporting material or a hole-transporting material having good heat resistance can be provided.

[0087] 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 with small driving voltage fluctuation can be provided. According to another embodiment of the present invention, a light-emitting device with long driving lifetime can be provided. According to another embodiment of the present invention, a light-emitting device, a light-emitting apparatus, an electronic device, and a display device with low power consumption can be provided.

[0088] According to one 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.

[0089] Note that the description of these effects does not preclude the existence of other effects. One embodiment of the present invention does not necessarily have all of these effects. Effects other than these can be extracted from the description in the specification, drawings, and claims. [Brief explanation of the drawings]

[0090] [Figure 1] 1A to 1C are diagrams showing a light-emitting device. [Figure 2] 2(A) and 2(B) are a top view and a cross-sectional view of the light-emitting device. [Figure 3] 3A to 3E are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 4] 4A and 4B are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 5]5A to 5D are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 6] 6A to 6C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 7] 7A to 7C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 8] 8A to 8C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 9] 9A and 9B are perspective views showing configuration examples of a display module. [Figure 10] 10(A) and 10(B) are cross-sectional views showing examples of the configuration of a display device. [Figure 11] FIG. 11 is a perspective view showing an example of the configuration of a display device. [Figure 12] FIG. 12 is a cross-sectional view showing an example of the configuration of a display device. [Figure 13] FIG. 13 is a cross-sectional view showing an example of the configuration of a display device. [Figure 14] 14A to 14C are diagrams showing configuration examples of display devices. [Figure 15] FIG. 15 is a cross-sectional view showing an example of the configuration of a display device. [Figure 16] 16A to 16C are diagrams showing configuration examples of display devices. [Figure 17] 17(A) to 17(D) are diagrams illustrating an example of a wearable device. [Figure 18] 18A to 18F are diagrams showing examples of electronic devices. [Figure 19] 19A to 19G are diagrams showing examples of electronic devices. [Figure 20] FIG. 20 is a diagram illustrating a photosensor. [Figure 21] Figures 21(A) and 21(B) are the 1H NMR spectra of tert-butyl (6-phenyl-benzo[b]naphtho[1,2-d]furanyl)-8-carbamate. [Figure 22] Figures 22(A) and 22(B) are the 1H NMR spectra of N-(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine. [Figure 23] Figures 23(A) and 23(B) are 1H NMR spectra of SFxBiBnf. [Figure 24] 24(A) and 24(B) are the absorption and emission spectra of SFxBiBnf. [Figure 25] Figures 25(A) and 25(B) are 1H NMR spectra of SFx(2)BiBnf. [Figure 26] 26(A) and 26(B) are the absorption and emission spectra of SFx(2)BiBnf. [Figure 27] FIG. 27 is a graph showing the luminance-current density characteristics of the light-emitting device 1 and the light-emitting device 2. As shown in FIG. [Figure 28] FIG. 28 is a graph showing the current efficiency-luminance characteristics of the light-emitting device 1 and the light-emitting device 2. As shown in FIG. [Figure 29] FIG. 29 is a diagram showing the luminance-voltage characteristics of the light-emitting device 1 and the light-emitting device 2. As shown in FIG. [Figure 30] FIG. 30 is a graph showing the current density-voltage characteristics of the light-emitting device 1 and the light-emitting device 2. As shown in FIG. [Figure 31] FIG. 31 is a graph showing the external quantum efficiency-luminance characteristics of the light-emitting device 1 and the light-emitting device 2. In FIG. [Figure 32] FIG. 32 shows the electroluminescence spectra of Light-Emitting Device 1 and Light-Emitting Device 2. As shown in FIG. [Figure 33] Figures 33(A) and 33(B) are the 1H NMR spectra of N-biphenyl-4-yl(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine. DETAILED DESCRIPTION OF THE INVENTION

[0091] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it will be readily understood by those skilled in the art that various changes can be made in form and detail without departing from the spirit and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the description of the embodiments shown below.

[0092] (Embodiment 1) In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0093] An organic compound according to one embodiment of the present invention is represented by the following general formula (G1).

[0094] [ka]

[0095] In the organic compound represented by the general formula (G1), X represents an oxygen atom or a sulfur atom. When X is an oxygen atom, the refractive index is lower than that of a compound having a sulfur atom, and elements using a compound with a low refractive index have the effect of increasing light extraction efficiency, which is preferable because it can provide a highly efficient light-emitting device. Furthermore, when X is a sulfur atom, the heat resistance is improved compared to a compound having an oxygen atom, which is preferable because it can provide a device that can withstand high-temperature operation. Furthermore, when sulfur is used, the refractive index is high, so by forming a cap film with a high refractive index on the cathode, it is possible to provide a light-emitting element with high light extraction efficiency.

[0096] Also, R 1 ~R 16One of the groups represented by general formula (g1) is a group represented by general formula (g1), and the remaining groups each independently represent any one of hydrogen (including deuterium), a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. In particular, hydrogen (including deuterium) and a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms are preferred because they enhance sublimation properties and enable the formation of a high-purity film of the organic EL material when a process for forming a film of the organic EL material by vacuum deposition is used in the device fabrication process. Devices formed from high-purity films are preferred because they result in highly reliable devices. Hydrogen is also preferred because it simplifies synthesis and reduces manufacturing costs.

[0097] [ka]

[0098] In the group represented by general formula (g1), Ar 1 is represented by the following general formula (Ar 1 -1), and Ar 2 represents a substituted or unsubstituted phenyl group or a phenyl group having at least a substituted or unsubstituted naphthyl group. 1 ~R 16 It binds to one of the following:

[0099] Ar 2 is represented by the following structural formula (Ar 2 -1) to the following structural formula (Ar 2 -20) is preferable because it can provide a compound with high hole transport properties and is also preferable because it can provide a compound with high resistance to repeated oxidation-reduction reactions. 2 -1) to structural formula (Ar 2 -4), structural formula (Ar 2-8) to structural formula (Ar 2 -11) is preferred because it can provide an organic film having high stability and a highly reliable device, and more preferably, it can provide a highly reliable device by using the structural formula (Ar 2 -8) to structural formula (Ar 2 -11) is preferred, and in terms of lower production costs, the structural formula (Ar 2 -1) to structural formula (Ar 2 -4) is preferred. 2 -4) and structural formula (Ar 2 The compound represented by the following structural formula (Ar-8) is preferred because it can maintain a high glass transition temperature while preventing a decrease in solubility, and therefore can be expected to be highly purified during synthesis, thereby providing highly reliable devices. 2 -1) to the following structural formula (Ar 2 -20), the asterisk indicates the bond to nitrogen in the general formula (g1).

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] General formula (Ar 1In the group represented by formula (1), Y represents an oxygen atom or a sulfur atom. When Y is an oxygen atom, the refractive index is lower than that of a compound having a sulfur atom, and elements using compounds with a low refractive index have the effect of increasing the light extraction efficiency, which is preferable because a highly efficient light-emitting device can be provided. Furthermore, when Y is a sulfur atom, the heat resistance is improved compared to compounds having an oxygen atom, which is preferable because a device that can withstand high-temperature operation can be provided. Furthermore, when sulfur is used, the refractive index is high, so by forming a cap film with a high refractive index on the cathode, a light-emitting element with high light extraction efficiency can be provided.

[0104] Also, R 17 ~R 26 are each independently any one of hydrogen (including deuterium), a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. In particular, when a process for forming a film of an organic EL material by vacuum deposition is used in the process for fabricating a device, hydrogen (including deuterium) and a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms are preferred because they enhance sublimation properties, enabling the formation of a film of a high-purity organic EL material. Furthermore, hydrogen is preferred because it simplifies synthesis. However, R 17 , R 24 ~R 26 Any one of the above is a bond bonded to the nitrogen atom in general formula (g1).

[0105] In addition, the general formula (Ar 1 In the group represented by formula (1), R 17is preferably a bond bonded to the nitrogen atom in general formula (g1), since this can provide a compound with high hole transporting properties and high redox resistance. That is, the group represented by general formula (g1) is preferably a group represented by the following general formula (g2), since this can provide a compound with high hole transporting properties and high redox resistance.

[0106] [ka]

[0107] The group represented by the general formula (g2) is a bond indicated by an asterisk, and R 1 ~R 16 In addition, in the group represented by general formula (g2), R 18 ~R 26 are each independently any one of hydrogen (including deuterium), a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. In particular, when a process for forming an organic EL material by vacuum deposition is used in the device fabrication process, hydrogen (including deuterium) or a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms is preferred because it increases sublimation properties, enabling the formation of a high-purity film of the organic EL material. Hydrogen is also preferred because it simplifies synthesis. However, R 18 is preferably a phenyl group for ease of synthesis.

[0108] In an organic compound according to one embodiment of the present invention having such a structure, the xanthene skeleton and the benzonaphthofuran skeleton are each directly (without a substituent) bonded to the nitrogen of the amine, and a phenyl group or a phenyl group having a naphthyl group is further bonded to the nitrogen of the amine, thereby providing an organic compound with high heat resistance and high hole transport properties. When the material of the present invention is used in an organic semiconductor device, it is preferable because a device with a low driving voltage can be provided, and as a result, an organic semiconductor device with low power consumption can be provided.

[0109] The group represented by general formula (g1) or the group represented by general formula (g2) is R 6 ~R 8 and R 13 ~R 16 It is preferable to bond to one of the above groups, since this provides a compound with high hole transport properties.

[0110] That is, organic compounds represented by the following general formula (G2) and general formula (G3) are preferred.

[0111] [ka]

[0112] [ka]

[0113] In the above general formula (G2) and general formula (G3), R 30 or R 31each independently represents any one of hydrogen (including deuterium), a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. In particular, when a process for forming an organic EL material by vacuum deposition is used in the device fabrication process, hydrogen (including deuterium) and a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms are preferred because they enhance sublimation properties, enabling the formation of a high-purity film of the organic EL material. Devices made of high-purity films are preferred because they result in highly reliable devices. Hydrogen is also preferred because it simplifies synthesis, leading to reduced manufacturing costs.

[0114] In addition, in the general formula (G2) and the general formula (G3), R 18 ~R 26 are each independently any one of hydrogen (including deuterium), a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 1 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. In particular, when a process for forming an organic EL material by vacuum deposition is used in the device fabrication process, hydrogen (including deuterium) or a substituted or unsubstituted linear alkyl group having 1 to 6 carbon atoms is preferred because it increases sublimation properties, enabling the formation of a high-purity film of the organic EL material. Hydrogen is also preferred because it simplifies synthesis. However, R 18 is preferably a phenyl group for ease of synthesis.

[0115] In the above general formula (G2) and general formula (G3), X, Ar 2 , and R 1 ~R 16is the same as the general formula (G1) above, so repeated explanation will be omitted.

[0116] In particular, the group represented by general formula (g1) or the group represented by general formula (g2) is R 7 or R 15 is preferable because it can provide a compound with high hole transport properties.

[0117] That is, organic compounds represented by the following general formula (G4) and general formula (G5) are preferred.

[0118] [ka]

[0119] [ka]

[0120] In addition, the general formulae (G1) to (G5) and the general formula (Ar 1 In formula (g2), specific examples of halogen include fluorine, chlorine, bromine, and iodine, and fluorine is particularly preferred because the molecular weight does not become too large.

[0121] In addition, the general formulas (G1) to (G5) and the general formula (Ar 1 In formula (g1), (g2), and general formula (g3), examples of the chain alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group.

[0122] In addition, the general formulas (G1) to (G5) and the general formula (Ar 1In formula (g1), (g2), and general formula (g3), specific examples of the branched alkyl group having 3 to 8 carbon atoms include an isopropyl group, a tert-butyl group, a sec-butyl group, an isobutyl group, a 2-methylhexyl group, a 2-ethylhexyl group, a 2-propylbutyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a neohexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group, and a 2,3-dimethylbutyl group.

[0123] In addition, the general formulae (G1) to (G5) and the general formula (Ar 1 In formula (g1), (g2), and general formula (g3), examples of the haloalkyl group having 1 to 6 carbon atoms include groups in which one or more hydrogen atoms of the above-mentioned linear alkyl group having 1 to 6 carbon atoms and branched alkyl group having 3 to 8 carbon atoms are substituted with fluorine, chlorine, bromine, and iodine, and alkyl groups substituted with fluorine are particularly preferred because they can provide highly reliable devices.

[0124] In addition, the general formulas (G1) to (G5) and the general formula (Ar 1 In formula (g1), (g2), specific examples of the saturated cyclic hydrocarbon group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. When the saturated cyclic hydrocarbon group having 3 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 aromatic hydrocarbon group having 6 to 13 carbon atoms.

[0125] In addition, the general formulas (G1) to (G5) and the general formula (Ar 1In formula (g1), (g2), and general formula (g3), specific examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a tert-butoxy group, a sec-butoxy group, an isobutoxy group, a pentyloxy group, an octyloxy group, an allyloxy group, a cyclohexyloxy group, a phenoxy group, and alkenyloxy groups such as a benzyloxy group, a vinyloxy group, a propenyloxy group, a butenyloxy group, a pentenyloxy group, and a hexenyloxy group.

[0126] In addition, the general formulas (G1) to (G5) and the general formula (Ar 1 In formula (g1-1) and general formula (g2), examples of the aromatic hydrocarbon group having 6 to 30 carbon atoms include a phenyl group, a tolyl group, a xylyl group, a biphenyl group, an indenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, an anthracenyl group, and a fluoranthenyl group. When the aromatic hydrocarbon 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 aromatic hydrocarbon group having 6 to 13 carbon atoms. In addition, Ar 2 When the phenyl group and / or naphthyl group contained in the formula (I) 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 aromatic hydrocarbon group having 6 to 13 carbon atoms.

[0127] In addition, the general formulas (G1) to (G5) and the general formula (Ar 1 In formula (g2), examples of the heteroaromatic hydrocarbon group having 1 to 30 carbon atoms include a carbazolyl group, an indolyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, etc. When the heteroaromatic hydrocarbon group having 1 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 aromatic hydrocarbon group having 6 to 13 carbon atoms.

[0128] In addition, the general formulae (G1) to (G5) and the general formula (Ar1 -1), the hydrogen contained in the general formula (g1) and the general formula (g2) includes deuterium.

[0129] The general formulae (G1) to (G5), the general formula (Ar 1 -1), in the organic compounds or groups represented by general formula (g1) and general formula (g2), R 1 ~R 26 Specific examples of elements or groups that can be used as the substituent include groups represented by the following structural formulae (1-1) to (1-25) and structural formulae (2-1) to (2-25). For groups that do not specify a bond, a monovalent group in which one of the hydrogen atoms has been eliminated can be used.

[0130] [ka]

[0131] [ka]

[0132] The organic compound of one embodiment of the present invention having the above structure can be a material with excellent hole-transport properties and high heat resistance. Furthermore, a thin film including a compound having such a structure is preferable because it has little change in film quality and can provide a device that is stable against heat or the passage of driving time. Furthermore, a device using a compound having such a structure can be a device that has high reliability against voltage because it has low driving voltage and small voltage fluctuation during driving, and also has excellent reliability when driven at high temperatures. Furthermore, a device with low power consumption can be provided. Furthermore, an organic compound having such a structure is preferable in terms of manufacturing cost because it has high sublimability and does not decompose during a vapor deposition process, allowing for stable production.

[0133] Specific examples of the organic compounds of one embodiment of the present invention described in this embodiment include organic compounds represented by the following structural formulas (100) to (224).

[0134]

change

[0135]

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[0136]

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[0137]

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[0138]

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[0139]

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[0140]

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[0141]

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[0142]

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[0143]

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[0144]

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[0145] [ka]

[0146] [ka]

[0147] [ka]

[0148] [ka]

[0149] [ka]

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] Here, the organic compound represented by the general formula (G1) will be described using the organic compound represented by the general formula (G4) as an example.

[0155] In addition, X and R in the following general formula (G4), reaction schemes (A-1a), (A-1b), (A-2), (B-1a), (B-1b), (B-2), (C-1a), (C-1b), and (C-2) 1 ~R 26 , Ar 2 Since the description of is the same as that of the general formula (G1) above, the description thereof will be omitted.

[0156] [ka]

[0157] Various reactions can be applied as a method for synthesizing the organic compound represented by the general formula (G4). For example, the organic compound represented by the general formula (G4) can be synthesized by carrying out the following synthesis methods 1 to 3.

[0158] <Method 1 for synthesizing organic compounds represented by general formula (G4)> The organic compound represented by general formula (G4) of the present invention can be synthesized as shown in the following synthesis schemes (A-1a), (A-1b) and (A-2).

[0159] First, we will explain the synthesis scheme (A-1a). That is, by coupling an aryl compound (compound 1) with an arylamine compound (compound 2), an arylamine compound (compound 3) can be obtained. The synthesis scheme (A-1a) is shown below.

[0160] [ka]

[0161] The arylamine compound (compound 3) can also be obtained by synthetic scheme (A-1b), which is another example of synthetic scheme (A-1a). That is, the arylamine compound (compound 3) can be obtained by coupling the arylamine compound (compound 4) with the aryl compound (compound 5). The synthetic scheme (A-1b) is shown below.

[0162] [ka]

[0163] Next, the synthesis scheme (A-2) will be explained. The target organic compound represented by general formula (G4) can be obtained by coupling an arylamine compound (compound 3) with an aryl compound (compound 6). The synthesis scheme (A-2) is shown below.

[0164] [ka]

[0165] <Method 2 for synthesizing organic compounds represented by general formula (G4)> The organic compound represented by general formula (G4) of the present invention can be synthesized according to the following synthesis schemes (B-1a), (B-1b) and (B-2).

[0166] First, we will explain the synthesis scheme (B-1a). That is, by coupling an arylamine compound (compound 7) with an aryl compound (compound 1), an arylamine compound (compound 8) can be obtained. The synthesis scheme (B-1a) is shown below.

[0167] [ka]

[0168] The arylamine compound (compound 8) can also be obtained by synthetic scheme (B-1b), which is another example of synthetic scheme (B-1a). That is, the arylamine compound (compound 8) can be obtained by coupling the aryl compound (compound 6) with the arylamine compound (compound 4). Synthetic scheme (B-1b) is shown below.

[0169] [ka]

[0170] Next, the synthesis scheme (B-2) will be explained. The target organic compound represented by general formula (G4) can be obtained by coupling an arylamine compound (compound 8) with an aryl compound (compound 5). The synthesis scheme (B-2) is shown below.

[0171] [ka]

[0172] <Method 3 for synthesizing organic compounds represented by general formula (G4)> The organic compound represented by general formula (G4) of the present invention can be synthesized as shown in the following synthesis schemes (C-1a), (C-1b) and (C-2).

[0173] First, we will explain the synthesis scheme (C-1a). That is, by coupling an arylamine compound (compound 7) with an aryl compound (compound 5), an arylamine compound (compound 9) can be obtained. The synthesis scheme (C-1a) is shown below.

[0174] [ka]

[0175] The arylamine compound (compound 9) can also be obtained by synthetic scheme (C-1b), which is another example of synthetic scheme (C-1a). That is, the arylamine compound (compound 9) can be obtained by coupling the aryl compound (compound 7) with the arylamine compound (compound 2). Synthetic scheme (C-1b) is shown below.

[0176] [ka]

[0177] Next, the synthesis scheme (C-2) will be explained. The target organic compound represented by general formula (G4) can be obtained by coupling an arylamine compound (compound 9) with an aryl compound (compound 1). The synthesis scheme (C-2) is shown below.

[0178] [ka]

[0179] In the above synthesis schemes (A-1a), (A-1b), (A-2), (B-1a), (B-1b), (B-2), (C-1a), (C-1b), and (C-2), Z 1 ~Z 3 each independently represents chlorine, bromine, iodine, or a triflate group, and the halogen is preferably chlorine, bromine, or iodine, more preferably bromine or iodine in consideration of reactivity, and more preferably chlorine or bromine in consideration of cost.

[0180] In the synthesis schemes (A-1a), (A-1b), (A-2), (B-1a), (B-1b), (B-2), (C-1a), (C-1b), and (C-2), when the Buchwald-Hartwig reaction is carried out using a palladium catalyst, bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), and allylpalladium(II) Palladium compounds such as palladium chloride (dimer) and ligands such as tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, and (S)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diisopropylphosphine) (abbreviation: cBRIDP) can be used. In this reaction, organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate, cesium carbonate, and sodium carbonate can be used. In this reaction, solvents such as toluene, xylene, benzene, tetrahydrofuran, and dioxane can be used. Reagents that can be used in this reaction are not limited to those listed above.

[0181] In addition, in the synthetic schemes (A-1a), (A-1b), (A-2), (B-1a), (B-1b), (B-2), (C-1a), (C-1b), and (C-2), an amination reaction can also be carried out using copper or a copper compound. Examples of the base used include inorganic bases such as potassium carbonate. Examples of solvents that can be used in this reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), toluene, xylene, and benzene. In this reaction, a reaction temperature of 100°C or higher allows the target product to be obtained in a shorter time and with a higher yield, so it is preferable to use DMPU or xylene, which have high boiling points. Furthermore, a reaction temperature of 150°C or higher is even more preferable, so DMPU is more preferably used. Reagents that can be used in this reaction are not limited to those listed above.

[0182] Although the synthesis method of the organic compound represented by general formula (G4) has been described above, the method for synthesizing the organic compound is not limited to the synthesis schemes (A-1a), (A-1b), (A-2), (B-1a), (B-1b), (B-2), (C-1a), (C-1b), and (C-2). Organic compounds with different substituents, substitution positions, skeletons, etc. can be synthesized by changing the raw materials so that the organic compound in question can be obtained.

[0183] Note that in another organic compound of one embodiment of the present invention (for example, an organic compound represented by general formula (G5)) that is bonded at a substitution position different from that of general formula (G4), Z 1 ~Z 3 The compound can be synthesized in the same manner by using a raw material substituted with a group represented by any one of the following formulas or an amino group:

[0184] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments.

[0185] (Embodiment 2) In this embodiment, an organic semiconductor device according to one embodiment of the present invention will be described in detail. The organic semiconductor device according to one embodiment of the present invention includes an active layer (such as the light-emitting layer 113 in a light-emitting device or a photoelectric conversion layer in a photosensor).

[0186] 1 is a schematic diagram of a light-emitting device according to one embodiment of the present invention. The light-emitting device includes a first electrode 101 provided over an insulator 1000, and an organic compound layer 103 between the first electrode 101 and a second electrode 102. The organic compound layer 103 includes an organic compound represented by the following general formula (G0), preferably at least one of the organic compounds represented by the general formula (G1) in Embodiment 1. The light-emitting layer 113 in the light-emitting device includes a luminescent center substance, and the luminescent center substance emits light when a voltage is applied between the first electrode 101 and the second electrode 102.

[0187] [ka]

[0188] In the general formula (G0), X represents an oxygen atom or a sulfur atom, and R 1 ~R 16 is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms.

[0189] [ka] In the group represented by general formula (g1), Ar 1is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted bisnaphthofuranyl group, or a substituted or unsubstituted bisnaphthothiophenyl group, and Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 1 to 30 carbon atoms, and the bond marked with an asterisk is R 1 ~R 16 It binds to one of the following:

[0190] In the above general formulae (G0) and (g1), examples of the heteroaromatic group having 1 to 30 carbon atoms include a pyridinyl group, a pyrimidinyl group, a triazinyl group, a phenanthroline-yl group, a carbazolyl group, a pyrrolyl group, a thiophenyl group, a furan-yl group, an imidazolyl group, a bipyridinyl group, a bipyrimidinyl group, a pyrazinyl group, a bipyrazinyl group, a quinolin-yl group, an isoquinolin-yl group, a benzoquinolin-yl group, a quinoxalin-yl group, a benzoquinoxalin-yl group, a dibenzoquinoxalin-yl group, an azofluoren-yl group, a diazofluoren-yl group, a benzocarbazol-yl group, a dibenzocarbazol-yl group, a dibenzofuran-yl group, a benzonaphthofuran-yl group, a dinaphthofuran-yl group, a dibenzofuran ... Examples thereof include a ran-yl group, a dibenzothiophen-yl group, a benzonaphthothiophen-yl group, a dinaphthothiophen-yl group, a benzofuropyridin-yl group, a benzofuropyrimidin-yl group, a benzothiopyridin-yl group, a benzothiopyrimidin-yl group, a naphthofuropyridin-yl group, a naphthofuropyrimidin-yl group, a naphthothiopyridin-yl group, a naphthothiopyrimidin-yl group, a dibenzoquinoxalin-yl group, an acridine-yl group, a xanthene-yl group, a phenothiazin-yl group, a phenoxazin-yl group, a phenazin-yl group, a triazol-yl group, an oxazol-yl group, an oxadiazol-yl group, a thiazol-yl group, a thiadiazol-yl group, a benzimidazol-yl group, or a pyrazol-yl group. When the heteroaromatic group having 1 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.

[0191] In addition, Ar in the above general formula (g1) 1 In the formula (I), when the dibenzofuranyl group, or the dibenzothiophenyl group, or the benzonaphthofuranyl group, or the benzonaphthothiophenyl group, or the bisnaphthofuranyl group, or the bisnaphthothiophenyl group 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.

[0192] In the organic compound represented by the general formula (G0), X, R 1 ~R 16 , Ar 1 and Ar 2 Among these, the structure common to general formula (G1) in the first embodiment can follow the structure of general formula (G1) in the first embodiment.

[0193] 1(A), the organic compound layer 103 preferably 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. The organic compound layer 103 may also include functional layers other than those described above, such as a hole blocking layer, an electron blocking layer, an exciton blocking layer, and a charge generating layer. Conversely, any of the layers described above may not be provided.

[0194] The organic compound represented by the general formula (G0) or the organic compound represented by the general formula (G1) in Embodiment 1 is preferably contained in a layer through which holes travel. Examples of the layer through which holes travel include a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting layer.

[0195] Although this embodiment describes the first electrode 101 as an electrode including an anode and the second electrode 102 as an electrode including a cathode, this may be reversed. The first electrode 101 and the second electrode 102 are formed as a single-layer structure or a stacked-layer structure. In the case of a stacked-layer structure, the layer in contact with the organic compound layer 103 functions as an anode or a cathode. In the case of a stacked-layer structure, there are no restrictions on the work function of layers other than the layer in contact with the organic compound layer 103, and materials may be selected depending on required characteristics such as resistance, ease of processing, reflectance, light transmittance, and stability.

[0196] The anode is preferably formed using a metal, alloy, conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or higher). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide (ITSO), indium oxide-zinc oxide, and indium oxide containing tungsten oxide and zinc oxide (IWZO). These conductive metal oxide films are usually formed by sputtering, but they may also be prepared by applying a sol-gel method. For example, indium oxide-zinc oxide can be formed by sputtering using a target in which 1 to 20 wt % of zinc oxide is added to indium oxide. Indium oxide containing tungsten oxide and zinc oxide (IWZO) can also be formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide. Other materials that can be used for the anode include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), aluminum (Al), and nitrides of metal materials (e.g., titanium nitride). A layer formed by stacking these materials can also be used as the anode. For example, a film formed by stacking Al, Ti, and ITSO on Ti in this order is preferred because of its high reflectivity, high efficiency, and the ability to achieve high resolution of several thousand ppi. Graphene can also be used as the anode material. In addition, by using a composite material capable of forming the hole injection layer 111 described later as a layer in contact with the anode (typically the hole injection layer), it becomes possible to select an electrode material regardless of the work function.

[0197] The hole injection layer 111 is provided in contact with the anode and has the function of facilitating the injection of holes into the organic compound layer 103. The hole injection layer 111 can be formed of a phthalocyanine compound such as phthalocyanine (abbreviation: HPc) or copper phthalocyanine (abbreviation: CuPc), a phthalocyanine complex compound, an aromatic amine compound such as 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB) or 4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), or a polymer compound such as poly(3,4-ethylenedioxythiophene) / polystyrenesulfonic acid (abbreviation: PEDOT / PSS).

[0198] Alternatively, the hole injection layer 111 may be formed of a substance having electron acceptor properties. Examples of the substance having acceptor properties include organic compounds having an electron-withdrawing group (such as a halogen group or a cyano group), such as 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-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile. In particular, compounds in which an electron-withdrawing group is bonded to a fused aromatic ring having multiple heteroatoms, such as HAT-CN, are preferred because of their thermal stability. Radialene derivatives having electron-withdrawing groups (especially halogen groups such as fluoro groups, cyano groups, etc.) are also preferred because of their extremely high electron-accepting properties. Specific examples include α,α',α''-1,2,3-cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenetris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropanetriylidenetris[2,3,4,5,6-pentafluorobenzeneacetonitrile]. As the substance having acceptor properties, in addition to the organic compounds described above, transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide can be used.

[0199] The hole-injection layer 111 is preferably formed using a composite material containing the above-mentioned material having an acceptor property and an organic compound having a hole-transport property.

[0200] As the organic compound having hole transport properties used in the composite material, various organic compounds can be used, such as aromatic amine compounds, heteroaromatic compounds, aromatic hydrocarbons, and polymer compounds (oligomers, dendrimers, polymers, etc.). Note that the organic compound having hole transport properties used in the composite material can be 1×10 -6 cm 2 Preferably, the organic compound has a hole mobility of 1 / Vs or more. The organic compound having hole transport properties used in the composite material is preferably a compound having a fused aromatic hydrocarbon ring or a π-electron-rich heteroaromatic ring. As the fused aromatic hydrocarbon ring, an anthracene ring, a naphthalene ring, or the like is preferred. Furthermore, 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 an aromatic ring or a heteroaromatic ring is further fused to the above ring is preferred.

[0201] Such organic compounds having hole-transporting properties preferably have a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, or an anthracene skeleton. In particular, aromatic amines having a substituent containing a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group may be used. It is preferable that these organic compounds having hole-transporting properties are substances having an N,N-bis(4-biphenyl)amino group, since this allows the fabrication of light-emitting devices with long lifetimes.

[0202] Specific examples of organic compounds having hole transport properties as described above include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzylamine (abbreviation: BnfBB1BP), and N,N-bis(4-biphenyl)benzylamine (abbreviation: BnfBB1BP). N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-4-amino-p-terphenyl] ]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβ NB-03), 4,4'-diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-Diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl] 4'-[4'-(3-phenyl-9H-carbazol-9-yl)biphenyl-4-yl]-4''-phenyltriphenylamine (abbreviated as TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviated as αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviated as αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviated as YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)furan N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N- Bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4' -[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'- Di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluoren]-2-amine (abbreviation: PCBASF), N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), N,N-bis( Examples of such amines include N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-2-amine, and N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-1-amine.

[0203] Other aromatic amine compounds that can be used as the hole-transporting material include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B). The organic compound represented by the general formula (G0) and the organic compound represented by the general formula (G1) in Embodiment 1 can also be suitably used.

[0204] By forming the hole injection layer 111, the hole injection property becomes good, and a light emitting device with a low driving voltage can be obtained.

[0205] Among substances having acceptor properties, organic compounds having acceptor properties are easy to use because they can be easily vapor-deposited and formed into a film.

[0206] The hole transport layer 112 is formed by containing an organic compound having a hole transport property. -6 cm 2 It is preferable that the hole mobility is / Vs or more.

[0207] Examples of the material having hole transport properties include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3-methylphenyl-4,4'-diaminobiphenyl (abbreviation: 4,4'-bis(9H-fluoren-2-yl)triphenylamine) ... '-(9-Phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl) Compounds with an aromatic amine skeleton, such as 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di( N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviation: BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,3'-Bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: βNCCP), 9-(3-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCmBP), 9-(4-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCBP), 9,9'-di-2-naphthyl-3,3'-9H,9'H-bicarbazole (abbreviation: BisβNCz), 9-(2-naphthyl)-9'-[1,1':4',1"-terf phenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-5'-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':4',1"-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-4-yl-3,3 '-9H,9'H-Bicarbazole, 9-(2-naphthyl)-9'-(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole, 9-phenyl-9'-(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole (abbreviation: PCCzTp), 9,9'-bis(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(4-biphenyl)-9'-(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(triphenylen-2-yl)-9'-[1,1':3',1"-taphe compounds having a carbazole skeleton such as [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-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV);Examples of the compounds include compounds having a furan skeleton, such as 4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among the compounds mentioned above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferable because they have good reliability, high hole-transporting properties, and contribute to reducing driving voltage. Note that the substances listed as materials having hole-transporting properties used in the composite material of the hole-injection layer 111 can also be suitably used as materials for the hole-transport layer 112. Note that the organic compound represented by the above general formula (G0) and the organic compound shown as general formula (G1) in Embodiment 1 can also be suitably used.

[0208] The luminescent center substance may be a fluorescent substance, a phosphorescent substance, a substance exhibiting thermally activated delayed fluorescence (TADF), or any other luminescent substance.

[0209] Examples of materials that can be used as fluorescent materials in the light-emitting layer include the following: In addition, fluorescent materials other than these can also be used.

[0210] 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-( 10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis(N,N',N'-triphenyl-1,4-phenylenediamine) (abbreviation: DPABPA), N,9 -diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (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 (abbreviated as DBC1), Coumarin 30, N-(9,10-diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA) , 9,10-bis(biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyra N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhTD), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhTD), Name: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB),6-Bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), N,N'-diphenyl-N,N'-(1,6-pyren-diyl)bis[(6-phenylbenzo[b]naphtho]] Examples include N,N'-diphenyl-N,N'-bis(9-phenyl-9H-carbazol-2-yl)naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviated as 3,10PCA2Nbf(IV)-02), and 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10FrA2Nbf(IV)-02). In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred due to their high hole-trapping properties and excellent luminous efficiency and reliability.

[0211] In addition, 5,9-diphenyl-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (abbreviation: DABNA1), 9-(biphenyl-3-yl)-N,N,5,11-tetraphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin-3-amine (abbreviation: DABNA2), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-N,N-diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin-7-amine (abbreviation: DABNA3), Amine (abbreviation: DPhA-tBu4DABNA), 2,12-di(tert-butyl)-N,N,5,9-tetra(4-tert-butylphenyl)-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin-7-amine (abbreviation: tBuDPhA-tBu4DABNA), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-7-methyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin (abbreviation: Me-tBu4DABNA), N 7 ,N 7 ,N 13 ,N 13 Fused heteroaromatic compounds containing nitrogen and boron, such as 5,9,11,15-octaphenyl-5H,9H,11H,15H-[1,4]benzazaborino[2,3,4-kl][1,4]benzazaborino[4',3',2':4,5][1,4]benzazaborino[3,2-b]phenazaborine-7,13-diamine (abbreviation: ν-DABNA) and 2-(4-tert-butylphenyl)benz[5,6]indolo[3,2,1-jk]benzo[b]carbazole (abbreviation: tBuPBibc), are particularly suitable for use as compounds having a diazaboranaphthoanthracene skeleton, since they have a narrow emission spectrum and can emit blue light with good color purity.

[0212] In addition to these, 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: BBCz-G), 9,11-bis[3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: BBCz-Y) and the like can be preferably used.

[0213] When a phosphorescent material is used as the light-emitting material in the light-emitting layer, examples of the phosphorescent material include the following materials.

[0214] Organometallic iridium complexes with a 4H-triazole skeleton, such as tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]) and tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]). , organometallic iridium complexes with a 1H-triazole skeleton, such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), fac-tris[1-(2,6-di [Ir(iPrpim)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), tris(2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazol-2-yl-κN3}-4-cyano organometallic iridium complexes with an imidazole skeleton, such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC2)phenyl-κC]iridium(III) (abbreviation: CNImIr), organometallic complexes with a benzimidazolidene skeleton, such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC2)phenyl-κC]iridium(III) (abbreviation: [Ir(cb)3]), and organometallic complexes with a benzimidazolidene skeleton, such as bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ] Organometallic iridium complexes with phenylpyridine derivatives containing electron-withdrawing groups as ligands, such as iridium(III) acetylacetonate (abbreviated as FIracac), are compounds that exhibit blue phosphorescence and have an emission peak in the wavelength range from 450 nm to 520 nm.

[0215] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6- Organometallic iridium complexes with a pyrimidine skeleton, such as (2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]) and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and tris(2-phenylpyridinato-N,C 2’) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C 2’) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mbfpypy-d3)]), {2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzo furo[2,3-b]pyridin-7-yl-κC}bis{5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: [Ir(5mtpy-d6)2(mbfpypy-iPr-d4)]), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfp ypy-d3)]), [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mdppy)]), [2-(4-d3-methyl-5-phenyl-2-pyridinyl-κN2)phenyl-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mdp Examples include organometallic iridium complexes with a pyridine backbone, such as [2-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviated as [Ir(ppy)2(mbfpypy)]), and rare earth metal complexes, such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviated as [Tb(acac)3(Phen)]). These compounds primarily exhibit green phosphorescence, with peak emission in the wavelength range of 500 to 600 nm. Organometallic iridium complexes with a pyrimidine backbone are particularly preferred due to their outstanding reliability and luminous efficiency.

[0216] and organometallic iridium complexes having a pyrimidine skeleton, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), and bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]). Organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’) iridium(III) acetylacetonate (abbreviated as [Ir(piq)2(acac)]), (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolinyl-κN]phenyl-κC]iridium(III), and (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolinyl-κN]phenyl-κC]iridium(III). In addition to iridium complexes, platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP) and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviated as [Eu(DBM)3(Phen)]) and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviated as [Eu(TTA)3(Phen)]) are compounds that exhibit red phosphorescence, with peak emission in the wavelength range from 600 to 700 nm. Organometallic iridium complexes with a pyrazine skeleton also exhibit excellent red chromaticity.

[0217] In addition to the phosphorescent compounds described above, known phosphorescent compounds may be selected and used.

[0218] TADF materials include fullerene and its derivatives, acridine and its derivatives, eosin derivatives, etc. Also available are metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of the metal-containing porphyrin include protoporphyrin-tin fluoride complex (SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), etioporphyrin-tin fluoride complex (SnF2(Etio I)), and octaethylporphyrin-platinum chloride complex (PtCl2OEP), all of which are shown in the following structural formulas.

[0219] [ka]

[0220] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), and Heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, such as 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA), can also be used. The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, and therefore has high electron transport and hole transport properties, and is therefore preferred. Among the skeletons having a π-electron-deficient heteroaromatic ring, pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferred because they are stable and reliable. In particular, benzofuropyrimidine skeleton, benzothienopyrimidine skeleton, benzofuropyrazine skeleton, and benzothienopyrazine skeleton are preferred because they have high acceptor properties and good reliability. Furthermore, among the skeletons having a π-electron-rich heteroaromatic ring, acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are preferred because they are stable and reliable.The furan skeleton is preferably a dibenzofuran skeleton, and the thiophene skeleton is preferably a dibenzothiophene skeleton. The pyrrole skeleton is particularly preferably an indole skeleton, a carbazole skeleton, an indolocarbazole skeleton, a bicarbazole skeleton, or a 3-(9-phenyl-9H-carbazol-3-yl)-9H-carbazole skeleton. Substances in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded are particularly preferred because the electron-donating ability of the π-electron-rich heteroaromatic ring and the electron-accepting ability of the π-electron-deficient heteroaromatic ring are both enhanced, thereby reducing the energy difference between the S1 level and the T1 level, thereby enabling efficient thermally activated delayed fluorescence. Instead of the π-electron-deficient heteroaromatic ring, an aromatic ring bonded to an electron-withdrawing group such as a cyano group may be used. The π-electron-rich skeleton may be, for example, an aromatic amine skeleton or a phenazine skeleton. Examples of usable π-electron-deficient skeletons include a xanthene skeleton, a thioxanthene dioxide skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or boranthrene, an aromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a heteroaromatic ring, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, etc. In this way, a π-electron-deficient skeleton and a π-electron-rich skeleton can be used in place of at least one of a π-electron-deficient heteroaromatic ring and a π-electron-rich heteroaromatic ring.

[0221] [ka]

[0222] TADF materials are materials with a small difference between the S1 and T1 levels, and have the ability to convert triplet excitation energy to singlet excitation energy through reverse intersystem crossing. Therefore, triplet excitation energy can be upconverted to singlet excitation energy (reverse intersystem crossing) using a small amount of thermal energy, allowing for efficient generation of a singlet excited state. Triplet excitation energy can also be converted into light emission.

[0223] Furthermore, exciplexes (also known as exciplexes), which form an excited state with two types of substances, have an extremely small difference between the S1 and T1 levels and function as TADF materials that can convert triplet excitation energy into singlet excitation energy.

[0224] Note that the T1 level can be measured using a phosphorescence spectrum observed at low temperatures (for example, 77 K to 10 K). For a TADF material, when a tangent line is drawn at the base of the fluorescence spectrum on the short wavelength side and the energy of the wavelength of the extrapolated line is taken as the S1 level, and a tangent line is drawn at the base of the phosphorescence spectrum on the short wavelength side and the energy of the wavelength of the extrapolated line is taken as the T1 level, the difference between S1 and T1 is preferably 0.3 eV or less, and more preferably 0.2 eV or less.

[0225] When a TADF material is used as a light-emitting material, the S1 level of the host material is preferably higher than the S1 level of the TADF material, and the T1 level of the host material is preferably higher than the T1 level of the TADF material.

[0226] 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.

[0227] Preferred materials having hole transport properties include organic compounds having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton. The π-electron-rich heteroaromatic ring is preferably a fused aromatic ring containing at least one of an acridine skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a furan skeleton, a thiophene skeleton, and a pyrrole skeleton, and more specifically, a carbazole ring, a dibenzothiophene ring, or a ring in which an aromatic ring or a heteroaromatic ring is fused to one of these rings.

[0228] Such organic compounds having hole-transporting properties preferably have a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, or an anthracene skeleton. In particular, aromatic amines having a substituent containing a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group may be used. It is preferable that these organic compounds having hole-transporting properties are substances having an N,N-bis(4-biphenyl)amino group, since this allows the fabrication of light-emitting devices with long lifetimes.

[0229] Examples of such organic compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: :BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1BP), Aromatic compounds such as PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviated as PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviated as PCBASF) Compounds with an aromatic amine skeleton, compounds with a carbazole skeleton such as 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), and 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,Examples of suitable materials include compounds having a thiophene skeleton, such as 8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), and compounds having a furan skeleton, such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among these, compounds having an aromatic amine skeleton or a carbazole skeleton are preferred because of their excellent reliability, high hole transport properties, and reduced driving voltage. The organic compounds listed as examples of materials having hole transport properties for the hole transport layer can also be used. The organic compound represented by the general formula (G0) and the organic compound shown as the general formula (G1) in Embodiment 1 can also be suitably used.

[0230] Materials with electron transport properties have an electron mobility of 1×10 at a square root of the electric field strength [V / cm] of 600. -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2 A substance having an electron mobility of 1 / Vs or more is preferred. Note that other substances can also be used as long as they have a higher electron transporting property than holes.

[0231] Preferred examples of the material having electron transport properties include metal complexes such as bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and organic compounds having a π-electron-deficient heteroaromatic ring. Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include organic compounds containing a heteroaromatic ring having a polyazole skeleton, organic compounds containing a heteroaromatic ring having a pyridine skeleton, organic compounds containing a heteroaromatic ring having a diazine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton.

[0232] Among these, organic compounds containing a heteroaromatic ring having a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), organic compounds containing a heteroaromatic ring having a pyridine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton are preferred because of their high reliability. In particular, organic compounds containing a heteroaromatic ring having a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing a heteroaromatic ring having a triazine skeleton have high electron transport properties and contribute to reduced driving voltage. In addition, benzofuropyrimidine skeletons, benzothienopyrimidine skeletons, benzofuropyrazine skeletons, and benzothienopyrazine skeletons are preferred because of their high acceptor properties and high reliability.

[0233] Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole- Organic compounds with an azole skeleton, such as 2-[3-(dibenzothiophen-4-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), 3,5-bis[3-(9H-carbazole-9-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), )phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P), 2-[3-(2-triphenylenyl)phenyl]-1,10 -phenanthroline (abbreviation: mTpPPhen), 2-phenyl-9-(2-triphenylenyl)-1,10-phenanthroline (abbreviation: Ph-TpPhen), 2-[4-(9-phenanthrenyl)-1-naphthalenyl]-1,10-phenanthroline (abbreviation: PnNPhen), 2-[4-(2-triphenylenyl)phenyl]-1,10-phenanthroline (abbreviation: pTpPPhen), and other organic compounds containing heteroaromatic rings with a pyridine skeleton, such as 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 2-[4-(3,6-diphenyl phenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 6mDBTPDBq-II), 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as 9mDBtBPNf pr), 9-[3'-(dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as 9pmDBtBPNfpr), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviated as 4,6mPnP2Pm), 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviated as 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviated as 4,6mCzP2Pm), 9,9'-[pyrimidinyl benzofuro[3,2-d]pyrimidine (abbreviated as 8BP-4mDBtPBfpm), 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3-b]pyrazine (abbreviated as 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)(biphenyl-3-yl)]naphtho[1',2':4,5]furo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), 8-[(2,2'-binaphthalen)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm), 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2, 6(P-Bqn)2Py), 2,2'-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviated as 2,6(NP-PPm)2Py), 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviated as 6mBP-4Cz2PPm), 2,6-bis(4-naphthalen-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviated as 2,4NP-6PyPPm), 4-[3,5-bis(9H-carbazol-9 -yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 7-[4-(9-phenyl-9H-carbazol-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz), and other organic compounds with a diazine skeleton, such as 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluoren]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d] 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole Rubazole (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 Phenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazin-2-yl]-11,12-dihydro-12-phenyl-indolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), 2-[3'-(triphenylen-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 3 Examples of suitable organic compounds include those containing a heteroaromatic ring with a triazine skeleton, such as -[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn) and 2-(biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',1''-terphenyl)-4-yl]-1-dibenzofuranyl}-1,3,5-triazine (abbreviation: mBP-TPDBfTzn). Organic compounds containing a heteroaromatic ring with a diazine skeleton, organic compounds containing a heteroaromatic ring with a pyridine skeleton, and organic compounds containing a heteroaromatic ring with a triazine skeleton are preferred due to their high reliability. In particular, organic compounds containing a heteroaromatic ring with a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing a heteroaromatic ring with a triazine skeleton have high electron transport properties and contribute to reduced driving voltage.

[0234] The TADF materials that can be used as host materials are the same as those listed above. When a TADF material is used as a host material, the triplet excitation energy generated in the TADF material is converted to singlet excitation energy through reverse intersystem crossing, and the energy is then transferred to the light-emitting material, thereby improving the luminous efficiency of the light-emitting device. In this case, the TADF material functions as an energy donor, and the light-emitting material functions as an energy acceptor.

[0235] This is very effective when the luminescent material is a fluorescent luminescent material. In this case, in order to obtain high luminous efficiency, the S1 level of the TADF material is preferably higher than the S1 level of the fluorescent luminescent material. In addition, the T1 level of the TADF material is preferably higher than the S1 level of the fluorescent luminescent material. Therefore, the T1 level of the TADF material is preferably higher than the T1 level of the fluorescent luminescent material.

[0236] It is also preferable to use a TADF material that emits light that overlaps with the wavelength of the lowest-energy absorption band of the fluorescent material, as this allows for smooth transfer of excitation energy from the TADF material to the fluorescent material, resulting in efficient light emission.

[0237] Furthermore, to efficiently generate singlet excitation energy from triplet excitation energy through reverse intersystem crossing, carrier recombination is preferred in the TADF material. Furthermore, it is preferable that the triplet excitation energy generated in the TADF material does not transfer to triplet excitation energy in the fluorescent material. To achieve this, the fluorescent material preferably has a protecting group around the luminophore (the skeleton responsible for light emission) of the fluorescent material. The protecting group is preferably a substituent without a π bond, and is preferably a saturated hydrocarbon. Specific examples include alkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, and trialkylsilyl groups with 3 to 10 carbon atoms. Multiple protecting groups are even more preferred. Substituents without a π bond have poor carrier transport properties, allowing for increased distance between the TADF material and the luminophore of the fluorescent material without significantly affecting carrier transport or carrier recombination. Here, the term "luminophore" refers to the atomic group (skeleton) responsible for light emission in the fluorescent material. The luminophore preferably has a skeleton having a π bond, preferably contains an aromatic ring, and preferably has a fused aromatic ring or a fused heteroaromatic ring. Examples of such luminophores include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, and a naphthobisbenzofuran skeleton. In particular, fluorescent materials having a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, or a naphthobisbenzofuran skeleton are preferred because of their high fluorescence quantum yield.

[0238] When a fluorescent emitting substance is used as the emitting substance, a material having an acene skeleton, particularly an anthracene skeleton, is suitable as the host material. Using a material having an anthracene skeleton as a host material for a fluorescent emitting substance enables the realization of an emitting layer with both excellent luminous efficiency and durability. As a material having an anthracene skeleton to be used as a host material, a material having a diphenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton, is preferred due to its chemical stability. Furthermore, host materials having a carbazole skeleton are preferred because of their enhanced hole injection and transport properties. However, host materials containing a benzocarbazole skeleton, in which a benzene ring is further condensed to the carbazole skeleton, are even more preferred because their HOMO level is approximately 0.1 eV higher than that of host materials having a carbazole skeleton, facilitating hole intrusion. In particular, host materials containing a dibenzocarbazole skeleton are preferred because their HOMO level is approximately 0.1 eV higher than that of host materials having a carbazole skeleton, facilitating hole intrusion, excellent hole transport properties, and high heat resistance. Therefore, a more preferable host material is a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). 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.

[0239] Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'- 9-(1-naphthyl)-10-(4-(2-naphthyl)phenyl)anthracene (abbreviation: αN-βNPAnth), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracen-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracenyl)benzo Examples include zo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-{4-[10-(biphenyl-4-yl)-9-anthracenyl]phenyl}-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), etc. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred choices because they exhibit very good properties.

[0240] The host material may be a mixture of multiple substances, and when a mixture of host materials is used, it is preferable to mix a material having electron-transporting properties with a material having hole-transporting properties. By mixing a material having electron-transporting properties with a material having hole-transporting properties, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region can also be easily controlled. The weight ratio of the content of the material having hole-transporting properties to the material having electron-transporting properties may be 1:19 to 19:1 (material having hole-transporting properties:material having electron-transporting properties).

[0241] A phosphorescent material can be used as part of the mixed material. The phosphorescent material can be used as an energy donor that provides excitation energy to a fluorescent material when the fluorescent material is used as a light-emitting material.

[0242] Furthermore, these mixed materials may form an exciplex. It is preferable to select a combination that forms an exciplex that emits light that overlaps with the wavelength of the lowest-energy absorption band of the light-emitting material, because this allows for smooth energy transfer and efficient light emission. Furthermore, using this structure is also preferable because it reduces the driving voltage.

[0243] At least one of the materials forming the exciplex may be a phosphorescent material, which allows efficient conversion of triplet excitation energy into singlet excitation energy through reverse intersystem crossing.

[0244] As a combination of materials that efficiently form an exciplex, it is preferable that the HOMO level of the hole-transporting material is equal to or higher than the HOMO level of the electron-transporting material. It is also preferable that the LUMO level of the hole-transporting material is equal to or higher than the LUMO level of the electron-transporting material. The LUMO and HOMO levels of the materials can be derived from the electrochemical properties (reduction potential and oxidation potential) of the materials measured by cyclic voltammetry (CV).

[0245] The formation of exciplexes can be confirmed by, for example, comparing the emission spectra of a hole-transporting material, an electron-transporting material, and a mixed film of these materials and observing the phenomenon that the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each material (or has a new peak at longer wavelengths). Alternatively, it can be confirmed by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and a mixed film of these materials and observing differences in transient response, such as the transient PL lifetime of the mixed film having a longer-lived component or a larger proportion of delayed components than the transient PL lifetimes of the individual materials. The above-mentioned transient PL can also be interpreted as transient electroluminescence (EL). In other words, the formation of exciplexes can also be confirmed by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and a mixed film of these materials and observing differences in transient response.

[0246] In the light-emitting device of one embodiment of the present invention, both the light-emitting layer and the hole-transport layer preferably contain the organic compound represented by General Formula (G0) and the organic compound shown as General Formula (G1) in Embodiment 1. Note that the organic compound represented by General Formula (G0) and the organic compound shown as General Formula (G1) in Embodiment 1 contained in the light-emitting layer and the hole-transport layer are preferably different organic compounds.

[0247] The electron transport layer 114 is a layer containing a material having an electron transport property. The material having an electron transport property is a material having an electron mobility of 1×10 at a square root of an electric field strength [V / cm] of 600. -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2A substance having an electron mobility of 1 / Vs or more is preferred. Note that other substances can be used as long as they have a higher electron transporting property than holes. Note that the organic compound is preferably an organic compound having a π-electron-deficient heteroaromatic ring. The organic compound having a π-electron-deficient heteroaromatic ring is preferably one or more of, for example, an organic compound having a heteroaromatic ring with a polyazole skeleton, an organic compound having a heteroaromatic ring with a pyridine skeleton, an organic compound having a heteroaromatic ring with a diazine skeleton, and an organic compound having a heteroaromatic ring with a triazine skeleton.

[0248] The organic compounds having electron transport properties that can be used in the electron transport layer 114 can be similar to the organic compounds that can be used in the light-emitting layer 113. Among these, organic compounds containing a heteroaromatic ring with a diazine skeleton, an organic compound containing a heteroaromatic ring with a pyridine skeleton, and an organic compound containing a heteroaromatic ring with a triazine skeleton are preferred because of their excellent reliability. In particular, organic compounds containing a heteroaromatic ring with a diazine (pyrimidine or pyrazine) skeleton and an organic compound containing a heteroaromatic ring with a triazine skeleton have high electron transport properties and contribute to reduced driving voltage. Organic compounds having a phenanthroline skeleton, such as mTpPPhen, PnNPhen, and mPPhen2P, are particularly preferred, with organic compounds having a phenanthroline dimer structure, such as mPPhen2P, being more preferred due to their excellent stability.

[0249] The electron transport layer 114 may have a laminated structure. A layer in the electron transport layer 114 having a laminated structure that is in contact with the light-emitting layer 113 may function as a hole-blocking layer. When the electron transport layer in contact with the light-emitting layer is made to function as a hole-blocking layer, it is preferable to use a material whose HOMO level is lower than the HOMO level of the material contained in the light-emitting layer 113 by 0.5 eV or more.

[0250] The electron-injection layer 115 may be a layer containing a compound or complex of an alkali metal or alkaline earth metal such as 8-hydroxyquinolinato-lithium (abbreviation: Liq), or 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviation: hpp2Py). The electron-injection layer 115 may be a layer made of a substance having electron-transporting properties containing an alkali metal, an alkaline earth metal, or a compound thereof.

[0251] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1(B)). The charge generation layer 116 is a layer capable of injecting holes into a layer in contact with the cathode side of the charge generation layer 116 and electrons into a layer in contact with the anode side of the charge generation layer 116 by applying a potential thereto. The charge generation layer 116 includes at least a P-type layer 117. The P-type layer 117 is preferably formed using the composite material listed above as a material that can be used to form the hole injection layer 111. The P-type layer 117 may also be formed by stacking a film containing an acceptor material and a film containing a hole transport material, both of which are materials that can be used to form the composite material. By applying a potential to the P-type layer 117, electrons are injected into the electron transport layer 114 and holes are injected into the cathode, thereby operating the light-emitting device. Furthermore, since the organic compound according to one embodiment of the present invention has a low refractive index, its use in the P-type layer 117 allows for a light-emitting device with excellent external quantum efficiency to be obtained.

[0252] It is preferable that the charge generating layer 116 be provided with either or both of an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117 .

[0253] The electron relay layer 118 contains at least a substance having electron transport properties and has the function of preventing interaction between the electron injection buffer layer 119 and the P-type layer 117 and smoothly transferring electrons. The LUMO level of the substance having electron transport properties contained in the electron relay layer 118 is preferably between the LUMO level of the acceptor substance in the P-type layer 117 and the LUMO level of the substance contained in the layer of the electron transport layer 114 that is in contact with the charge generation layer 116. The specific energy level of the LUMO level of the substance having electron transport properties used in the electron relay layer 118 is −5.0 eV or higher, preferably −5.0 eV or higher and −3.0 eV or lower. Note that the substance having electron transport properties used in the electron relay layer 118 is preferably a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0254] The electron injection buffer layer 119 can be made of a material with high electron injection properties, such as alkali metals, alkaline earth metals, rare earth metals, and compounds thereof (alkali metal compounds (including oxides such as lithium oxide, halides, and carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (including oxides, halides, and carbonates), or rare earth metal compounds (including oxides, halides, and carbonates)).

[0255] When the electron-injection buffer layer 119 is formed to contain a substance having electron-transporting properties and a donor substance, the donor substance can be an alkali metal, an alkaline earth metal, a rare earth metal, or a compound thereof (an alkali metal compound (including an oxide such as lithium oxide, a halide, or a carbonate such as lithium carbonate or cesium carbonate), an alkaline earth metal compound (including an oxide, a halide, or a carbonate), or a rare earth metal compound (including an oxide, a halide, or a carbonate)), or an organic compound such as tetrathianaphthacene (abbreviation: TTN), nickelocene, or decamethylnickelocene. Note that the substance having electron-transporting properties can be formed using the same material as the material for forming the electron-transporting layer 114 described above.

[0256] The second electrode 102 is an electrode including a cathode. The second electrode 102 may have a laminated structure, in which case the layer in contact with the organic compound layer 103 functions as the cathode. Materials that form the cathode include metals, alloys, electrically conductive compounds, and mixtures thereof, each having a low work function (specifically, 3.8 eV or less). 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), and strontium (Sr), alloys (MgAg, AlLi), and compounds (lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), etc.) containing these elements, rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these elements. However, by providing the electron injection layer 115 or a thin film of the above-mentioned material with a small work function between the second electrode 102 and the electron transport layer, various conductive materials, such as Al, Ag, ITO, indium oxide-tin oxide containing silicon or silicon oxide, can be used as the cathode regardless of the magnitude of the work function.

[0257] Note that when the second electrode 102 is formed using a material that is transparent to visible light, a light-emitting device that emits light from the second electrode 102 side can be obtained. In this case, by forming a capping layer in contact with the second electrode 102, it is possible to improve the light extraction efficiency. The capping layer is preferably an organic compound with a high refractive index. As the organic compound, an organic compound having a hole-transporting property is preferable, an organic compound represented by the above general formula (G0) is more preferable, and the organic compound represented by the general formula (G1) in Embodiment 1 is particularly preferable. The capping layer may have a stacked structure of layers using materials with different refractive indexes.

[0258] These conductive materials can be formed into films by dry methods such as vacuum deposition or sputtering, inkjet methods, spin coating, etc. Alternatively, they may be formed by a wet method using a sol-gel method, or by a wet method using a paste of a metal material.

[0259] In addition, various methods, whether dry or wet, can be used to form the organic compound layer 103. For example, vacuum deposition, gravure printing, offset printing, screen printing, inkjet printing, spin coating, or the like may be used.

[0260] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0261] Next, an embodiment of a light-emitting device having a structure in which multiple light-emitting units are stacked (also referred to as a stacked element or a tandem element) will be described with reference to FIG. 1(C). This light-emitting device has multiple light-emitting units between an anode and a cathode. One light-emitting unit has a structure substantially similar to that of the organic compound layer 103 shown in FIG. 1(A). In other words, the light-emitting device shown in FIG. 1(C) is a light-emitting device having multiple light-emitting units, and the light-emitting device shown in FIG. 1(A) or 1(B) can be said to be a light-emitting device having one light-emitting unit.

[0262] 1(C), a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between a first electrode 501 and a second electrode 502, and a charge generation layer 513 is provided between the first light-emitting unit 511 and the second light-emitting unit 512. The first electrode 501 and the second electrode 502 correspond to the first electrode 101 and the second electrode 102 in FIG. 1(A), respectively, and the same elements as those described in the description of FIG. 1(A) can be applied to them. The first light-emitting unit 511 and the second light-emitting unit 512 may have the same structure or different structures.

[0263] The charge generation layer 513 has a function of injecting electrons into one light-emitting unit and injecting holes into the other light-emitting unit when a voltage is applied between the first electrode 501 and the second electrode 502. That is, in FIG. 1C, when a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the charge generation layer 513 may inject electrons into the first light-emitting unit 511 and inject holes into the second light-emitting unit 512.

[0264] The charge generation layer 513 is preferably formed to have the same structure as the charge generation layer 116 described in FIG. 1B. A composite material of an organic compound and a metal oxide has excellent carrier injection and carrier transport properties, and therefore can achieve low-voltage driving and low-current driving. Note that when the anode side surface of the light-emitting unit is in contact with the charge generation layer 513, the charge generation layer 513 can also serve as a hole injection layer for the light-emitting unit, and therefore the light-emitting unit does not need to be provided with a hole injection layer.

[0265] Furthermore, when the electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer layer 119 plays the role of an electron injection layer in the light-emitting unit on the anode side, so that it is not necessarily necessary to form an electron injection layer in the light-emitting unit on the anode side.

[0266] 1C illustrates a light-emitting device having two light-emitting units, but the present invention can also be applied to a light-emitting device having three or more stacked light-emitting units. By disposing a plurality of light-emitting units between a pair of electrodes and separating them with a charge-generating layer 513, as in the light-emitting device according to this embodiment, high-luminance light emission can be achieved while maintaining a low current density, and an element with a long life can be realized. Furthermore, a light-emitting device that can be driven at a low voltage and consumes low power can be realized.

[0267] Furthermore, by making each light-emitting unit emit a different light color, the light-emitting device as a whole can emit light of a desired color. For example, in a light-emitting device having two light-emitting units, it is possible to obtain a light-emitting device that emits white light as a whole by obtaining red and green light from the first light-emitting unit and blue light from the second light-emitting unit.

[0268] The organic compound layer 103, the first light-emitting unit 511, the second light-emitting unit 512, the charge generation layer, and the electrodes can be formed by, for example, evaporation (including vacuum evaporation), droplet discharge (also called ink-jet), coating, gravure printing, etc. They may also contain low-molecular-weight materials, medium-molecular-weight materials (including oligomers and dendrimers), or polymer materials.

[0269] Next, an organic semiconductor device according to one embodiment of the present invention will be described.

[0270] 20 is a schematic diagram of a photosensor of one embodiment of the present invention. The photosensor includes a first electrode 101S over an insulator 1000S and an organic compound layer 103S between the first electrode 101S and a second electrode 102S. The organic compound layer 103S includes at least a photoelectric conversion layer 123 and may further include a layer having a different function. The organic compound layer 103S includes the organic compound represented by the general formula (G1) in Embodiment 1.

[0271] The photoelectric conversion layer 123 is a layer that generates carriers and includes a p-type semiconductor and an n-type semiconductor. Charges are generated by light 124 incident on the photoelectric conversion layer 123, and can be extracted as a current.

[0272] In addition to the photoelectric conversion layer 123, the organic compound layer 103S preferably has functional layers such as a hole injection layer 111S, a hole transport layer 112S, an electron transport layer 114S, and an electron injection layer 115S, as shown in Fig. 20. The organic compound layer 103S may also include functional layers other than the functional layers described above. Conversely, any of the layers described above may not be provided.

[0273] Note that the organic compound represented by the general formula (G1) in Embodiment 1 is preferably contained in a layer through which holes are transported, such as a hole injection layer, a hole transport layer, an electron blocking layer, and a photoelectric conversion layer.

[0274] In this embodiment, the first electrode 101S and the second electrode 102S are formed as a single layer or a stacked layer. In the case of a stacked layer, the layer in contact with the organic compound layer 103S functions as an anode or a cathode. When the electrodes have a stacked layer, there are no restrictions on the work function of layers other than the layer in contact with the organic compound layer 103S, and materials may be selected according to required characteristics such as resistance, ease of processing, reflectance, light transmittance, and stability. The first electrode 101S and the second electrode 102S may be formed using the same material as the first electrode 101 and the second electrode 102. However, the electrode that captures light is preferably formed using a material that transmits light of a wavelength that can be photoelectrically converted in the photoelectric conversion layer, more preferably with a transmittance of 50% or more, and even more preferably with a transmittance of 70% or more. For the first electrode 101S and the second electrode 102S, the electrode that receives holes is preferably made of a material listed as being preferably used as an anode in a light-emitting device, and for the electrode that receives electrons, it is preferably made of a material listed as being preferably used as a cathode in a light-emitting device.

[0275] The hole-injection layer 111S, the hole-transport layer 112S, the electron-transport layer 114S, the electron-injection layer 115S, and other functional layers can be made of the same materials as those listed as the functional layers constituting the light-emitting device. Note that the layer having a hole-transporting function preferably contains the organic compound of one embodiment of the present invention.

[0276] The photoelectric conversion layer 123 is a layer that generates carriers based on incident light and is a layer that includes a semiconductor. Examples of the semiconductor include inorganic semiconductors such as silicon and organic semiconductors that include organic compounds. In this embodiment, an example in which an organic semiconductor is used as the semiconductor included 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 (for example, vacuum deposition), which is preferable because a common manufacturing device can be used.

[0277] Furthermore, the photoelectric conversion layer 123 contains at least a p-type semiconductor material and an n-type semiconductor material.

[0278] Examples of p-type semiconductor materials include electron-donating organic semiconductor materials such as copper(II) phthalocyanine (CuPc), tetraphenyldibenzoperiflanthene (DBP), zinc phthalocyanine (ZnPc), tin phthalocyanine (SnPc), and quinacridone.

[0279] Examples of p-type semiconductor materials include carbazole derivatives, thiophene derivatives, furan derivatives, compounds having an aromatic amine skeleton, etc. Examples of p-type semiconductor materials include naphthalene derivatives, anthracene derivatives, pyrene derivatives, triphenylene derivatives, fluorene derivatives, pyrrole derivatives, benzofuran derivatives, benzothiophene derivatives, indole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, indolocarbazole derivatives, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, quinacridone derivatives, polyphenylenevinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, polythiophene derivatives, etc.

[0280] As n-type semiconductor materials, fullerenes (e.g., C 60 , C 70 Examples of suitable materials include electron-accepting organic semiconductor materials such as fullerene derivatives, etc. Fullerenes have a soccer ball-like shape, which is energetically stable. Fullerenes have deep (low) highest occupied molecular orbital (HOMO) and LUMO levels. Because fullerenes have a deep LUMO level, they have extremely high electron-accepting (acceptor) properties. Normally, when the π-electron conjugation (resonance) spreads on a plane, as in benzene, the electron-donating (donor) properties increase, but because fullerenes have a spherical shape, they have high electron-accepting properties despite the wide spread π-electron conjugation. High electron-accepting properties allow charge separation to occur quickly and efficiently, making them useful as photoelectric conversion devices. C 60 , C 70 Both have a wide absorption band in the visible light region, especially C 70 is C 60 It is preferable because it has a larger π-electron conjugated system and a wide absorption band in the long wavelength region compared to [6,6]-Phenyl-C 71 -butyric acid methyl ester (abbreviation: PC71BM), [6,6]-Phenyl-C 61-butyric acid methyl ester (abbreviation: PC61BM), 1',1'',4',4''-Tetrahydro-di[1,4]methanonaphthaleno[1,2:2',3',56,60:2'',3''][5,6]fulrerene-C 60 (abbreviated as ICBA) and others.

[0281] Examples of n-type semiconductor materials include metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline derivatives, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, naphthalene derivatives, anthracene derivatives, coumarin derivatives, rhodamine derivatives, triazine derivatives, and quinone derivatives.

[0282] Moreover, the photoelectric conversion layer 123 is preferably a laminated film of a first layer having a p-type semiconductor material and a second layer having an n-type semiconductor material.

[0283] In the light-emitting devices having the above configurations, the photoelectric conversion layer 123 is preferably a mixed film containing a p-type semiconductor material and an n-type semiconductor material.

[0284] The HOMO level of the electron-donating organic semiconductor material is preferably shallower (higher) than the HOMO level of the electron-accepting organic semiconductor material, and the LUMO level of the electron-donating organic semiconductor material is preferably shallower (higher) than the LUMO level of the electron-accepting organic semiconductor material.

[0285] Note that a spherical fullerene may be used as the electron-accepting organic semiconductor material, and a planar organic semiconductor material may be used as the electron-donating organic semiconductor material. Molecules with similar shapes tend to aggregate together, and when molecules of the same type aggregate, the energy levels of their molecular orbitals become close, which can improve carrier transport properties.

[0286] In the light-emitting device and photosensor according to one embodiment of the present invention having the above-described structure, the organic compound represented by the general formula (G0) and the organic compound represented by the general formula (G1) in Embodiment 1 have excellent hole-transport properties and high heat resistance. Therefore, by fabricating a device using the organic compound, a device can be provided that operates at a low driving voltage and has excellent reliability when operated at high temperatures. Furthermore, a thin film including an organic compound having such a structure is preferable because it can provide a device that is stable against heat or operation due to minimal changes in film quality. Furthermore, a device using an organic compound having such a structure can provide a device that operates at a low driving voltage and has high reliability against voltage due to small voltage fluctuations during operation, and that has excellent reliability when operated at high temperatures. Furthermore, it is preferable because it can provide a device that consumes low power. Furthermore, an organic compound having such a structure is preferable in terms of manufacturing cost because it has high sublimability and does not decompose during a vapor deposition process, allowing for stable production.

[0287] (Embodiment 3) 2A and 2B, a display device is formed by forming a plurality of light-emitting devices 130 over an insulating layer 175. In this embodiment, a display device according to another embodiment of the present invention will be described in detail.

[0288] The display device 100 has a pixel section 177 in which a plurality of pixels 178 are arranged in a matrix. The pixel 178 has a sub-pixel 110R, a sub-pixel 110G, and a sub-pixel 110B.

[0289] In this specification and the like, when describing matters common to, for example, the subpixels 110R, 110G, and 110B, they may be referred to as the subpixels 110. When describing matters common to other components distinguished by alphabets, they may also be described using symbols without the alphabets.

[0290] The sub-pixel 110R emits red light, the sub-pixel 110G emits green light, and the sub-pixel 110B emits blue light. This allows an image to be displayed in the pixel unit 177. In this embodiment, sub-pixels of three colors, red (R), green (G), and blue (B), are described as an example, but combinations of sub-pixels of other colors may also be used. The number of sub-pixels is not limited to three, and may be four or more. Examples of four sub-pixels include sub-pixels of four colors, R, G, B, and white (W), sub-pixels of four colors, R, G, B, and Y, and sub-pixels of R, G, B, and infrared (IR).

[0291] In this specification, 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.

[0292] 2A shows an example in which sub-pixels of different colors are arranged side by side in the X direction, and sub-pixels of the same color are arranged side by side in the Y direction. Note that sub-pixels of different colors may also be arranged side by side in the Y direction, and sub-pixels of the same color may also be arranged side by side in the X direction.

[0293] A connection section 140 may be provided outside the pixel section 177, and a region 141 may also be provided. When the region 141 is provided, the region 141 is provided between the pixel section 177 and the connection section 140. When the region 141 is provided, an organic compound layer is provided in the region 141. Furthermore, a conductive layer 151C is provided in the connection section 140.

[0294] 2A shows an example in which the region 141 and the connection portion 140 are located on the right side of the pixel portion 177, but the positions of the region 141 and the connection portion 140 are not particularly limited. The region 141 and the connection portion 140 may be singular or plural.

[0295] 2(B) is an example of a cross-sectional view taken along dashed line A1-A2 in FIG. 2(A). As shown in FIG. 2(B), the display device 100 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 provided on a substrate (not shown). The insulating layer 175, the insulating layer 174, and the insulating layer 173 have openings that reach the conductive layer 172, and a plug 176 is provided to fill the opening.

[0296] In the pixel section 177, the light-emitting device 130 is provided on the insulating layer 175 and the plug 176. A protective layer 131 is provided to cover the light-emitting device 130. The substrate 120 is bonded to the protective layer 131 by a resin layer 122. Preferably, an inorganic insulating layer 125 and an insulating layer 127 on the inorganic insulating layer 125 are provided between adjacent light-emitting devices 130.

[0297] Although multiple cross sections of the inorganic insulating layer 125 and the insulating layer 127 are shown in FIG. 2B, when the display device 100 is viewed from above, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are each connected into one.

[0298] 2(B) shows light emitting device 130R, light emitting device 130G, and light emitting device 130B. Light emitting device 130R, light emitting device 130G, and light emitting device 130B emit light of different colors. For example, light emitting device 130R can emit red light, light emitting device 130G can emit green light, and light emitting device 130B can emit blue light. Light emitting device 130R, light emitting device 130G, or light emitting device 130B may also emit other visible light or infrared light.

[0299] The display device of one embodiment of the present invention can be, for example, a top-emission type that emits light in the direction opposite to the substrate on which the light-emitting device is formed. Note that the display device of one embodiment of the present invention may also be a bottom-emission type.

[0300] The light-emitting device 130R has a first electrode 101R (pixel electrode) composed of a conductive layer 151R and a conductive layer 152R, an organic compound layer 103R on the first electrode, a common layer 104 on the organic compound layer 103R, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but is preferably provided because it can reduce damage to the organic compound layer 103R during processing.

[0301] The light-emitting device 130G has a first electrode 101G (pixel electrode) composed of a conductive layer 151G and a conductive layer 152G, an organic compound layer 103G on the first electrode, a common layer 104 on the organic compound layer 103G, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but is preferably provided because it can reduce damage to the organic compound layer 103G during processing.

[0302] The light-emitting device 130B has the same configuration as that described in Embodiment 1. It includes a first electrode 101B (pixel electrode) including a conductive layer 151B and a conductive layer 152B, an organic compound layer 103B on the first electrode, a common layer 104 on the organic compound layer 103B, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but is preferably provided because it can reduce damage to the organic compound layer 103B during processing. When the common layer 104 is provided, the stacked structure of the organic compound layer 103B and the common layer 104 corresponds to the organic compound layer 103 in Embodiment 1. When the common layer 104 is not provided, the organic compound layer 103B corresponds to the organic compound layer 103 in Embodiment 1.

[0303] The common layer 104 is preferably an electron transport layer. When the common layer 104 is an electron transport layer, the electron transport layer preferably has a laminated structure, and it is more preferable that the layer on the second electrode side is the common layer 104 and the layer on the light-emitting layer side is the organic compound layer 103.

[0304] The light emitting devices 130R and 130G are also light emitting devices fabricated through a photolithography process.

[0305] One of the pixel electrode and the common electrode of the light-emitting device 130 functions as an anode, and the other functions as a cathode. In the following description, unless otherwise specified, the pixel electrode functions as an anode and the common electrode functions as a cathode.

[0306] The organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B are independent island-shaped layers for each light-emitting device or each emitted color. By providing the organic compound layer 103 in an island shape for each light-emitting device 130, leakage current between adjacent light-emitting devices 130 can be suppressed even in a high-resolution display device. This makes it possible to prevent crosstalk and realize a display device with extremely high contrast. In particular, a display device with high current efficiency at low brightness can be realized.

[0307] The island-shaped organic compound layer 103 is formed by depositing an organic compound film and processing the organic compound film using a photolithography method.

[0308] The organic compound layer 103 is preferably provided so as to cover the top and side surfaces of the first electrode (pixel electrode) of the light-emitting device 130. This makes it easier to increase the aperture ratio of the display device 100 compared to a configuration in which the end of the organic compound layer 103 is located inside the end of the pixel electrode. Furthermore, covering the side surfaces of the pixel electrode of the light-emitting device 130 with the organic compound layer 103 prevents the pixel electrode from coming into contact with the second electrode 102, thereby preventing short circuits in the light-emitting device 130.

[0309] In the display device of one embodiment of the present invention, the first electrode (pixel electrode) of the light-emitting device preferably has a stacked-layer structure. For example, in the example shown in FIG. 2B, the first electrode of the light-emitting device 130 has a stacked-layer structure of a conductive layer 151 and a conductive layer 152.

[0310] For example, a metal material can be used for the conductive layer 151. Specifically, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd), etc., and alloys containing appropriate combinations of these metals can also be used.

[0311] The conductive layer 152 can be formed using an oxide containing one or more selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon. For example, it is preferable to use a conductive oxide containing one or more of indium oxide, indium tin oxide, indium zinc oxide, zinc oxide, zinc oxide containing gallium, titanium oxide, indium zinc oxide containing gallium, indium zinc oxide containing aluminum, indium tin oxide containing silicon, and indium zinc oxide containing silicon. In particular, indium tin oxide containing silicon has a large work function, for example, a work function of 4.0 eV or more, and therefore can be suitably used for the conductive layer 152.

[0312] The conductive layer 151 may have a stacked structure of multiple layers containing different materials, and the conductive layer 152 may have a stacked structure of multiple layers containing different materials. In this case, the conductive layer 151 may include a layer containing a material that can be used for the conductive layer 152, such as a conductive oxide, or the conductive layer 152 may include a layer containing a material that can be used for the conductive layer 151, such as a metal material. For example, when the conductive layer 151 has a stacked structure of two or more layers, a layer in contact with the conductive layer 152 can be a layer containing a material that can be used for the conductive layer 152.

[0313] Next, an example of a method for manufacturing the display device 100 having the structure shown in FIG. 2A will be described with reference to FIGS.

[0314] [Production method example 1] The thin films (insulating films, semiconductor films, conductive films, etc.) that make up the display device can be formed using a sputtering method, a chemical vapor deposition (CVD) method, a vacuum deposition method, a pulsed laser deposition (PLD) method, an ALD method, etc.

[0315] Furthermore, thin films (insulating films, semiconductor films, conductive films, etc.) that constitute the display device can be formed by wet film formation methods such as spin coating, dipping, spray coating, inkjet, dispensing, screen printing, offset printing, doctor knife method, slit coating, roll coating, curtain coating, or knife coating.

[0316] Furthermore, when processing the thin films that constitute the display device, they can be processed using, for example, photolithography.

[0317] In photolithography, the light used for exposure may be, for example, i-line (wavelength 365 nm), g-line (wavelength 436 nm), h-line (wavelength 405 nm), or a mixture of these. Other light sources that can be used include ultraviolet light, KrF laser light, and ArF laser light. Exposure may also be performed using immersion exposure techniques. Extreme ultraviolet (EUV) light or X-rays may also be used as light for exposure. An electron beam may also be used instead of light for exposure.

[0318] The thin film can be etched by dry etching, wet etching, sandblasting, or the like.

[0319] 3A, an insulating layer 171 is formed on a substrate (not shown). Subsequently, conductive layers 172 and 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 layers 172 and 179. Subsequently, an insulating layer 174 is formed on the insulating layer 173, and an insulating layer 175 is formed on the insulating layer 174.

[0320] The substrate may be a substrate having heat resistance at least sufficient to withstand subsequent heat treatment, such as a glass substrate, a quartz substrate, a sapphire substrate, a ceramic substrate, an organic resin substrate, a single crystal semiconductor substrate made of silicon or silicon carbide, a polycrystalline semiconductor substrate, a compound semiconductor substrate made of silicon germanium, or an SOI substrate.

[0321] 3A, openings are formed in the insulating layers 175, 174, and 173, reaching the conductive layer 172. Then, plugs 176 are formed to fill the openings.

[0322] 3A, a conductive film 151f, which will later become the conductive layers 151R, 151G, 151B, and 151C, and a conductive film 152f, which will later become the conductive layers 152R, 152G, 152B, and 152C, are formed on the plug 176 and the insulating layer 175. The conductive film 151f can be formed of, for example, a metal material. The conductive film 152f can be formed of, for example, an oxide containing one or more elements selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon.

[0323] 3A, a resist mask 191 is formed over the conductive film 152f. The resist mask 191 can be formed by applying a photosensitive material (photoresist), exposing it to light, and developing it.

[0324] 3B, for example, the conductive film 151f and the conductive film 152f are removed from regions that do not overlap with the resist mask 191. As a result, the conductive layer 151 and the conductive layer 152 are formed.

[0325] 3(C), the resist mask 191 is removed. The resist mask 191 can be removed by ashing using oxygen plasma, for example.

[0326] Next, as shown in FIG. 3(D), an insulating film 156f, which will later become insulating layers 156R, 156G, 156B, and 156C, is formed on conductive layer 152R, conductive layer 152G, conductive layer 152B, conductive layer 152C, and insulating layer 175.

[0327] The insulating film 156f can be an inorganic insulating film such as an insulating oxide film, an insulating nitride film, an insulating oxynitride film, or an insulating nitride oxide film, for example, a silicon oxynitride film.

[0328] Subsequently, as shown in FIG. 3(E), the insulating film 156f is processed to form an insulating layer 156R, an insulating layer 156G, an insulating layer 156B, and an insulating layer 156C.

[0329] 4(A), the organic compound film 103Rf is formed on the conductive layer 152R, the conductive layer 152G, the conductive layer 152B, and the insulating layer 175. Note that, as shown in FIG. 4(A), the organic compound film 103Rf is not formed on the conductive layer 152C.

[0330] Subsequently, as shown in FIG. 4(A), a sacrificial film 158Rf and a mask film 159Rf are formed.

[0331] 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.

[0332] The sacrificial film 158Rf is made of a film that is highly resistant to the processing conditions of the organic compound film 103Rf, specifically, a film that has a large etching selectivity with respect to the organic compound film 103Rf.The mask film 159Rf is made of a film that has a large etching selectivity with respect to the sacrificial film 158Rf.

[0333] The sacrificial film 158Rf and the mask film 159Rf are formed at a temperature lower than the heat-resistant temperature of the organic compound film 103Rf. The substrate temperature during the formation of 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. The light-emitting device of one embodiment of the present invention includes the first compound, and therefore can provide a display device with good display quality even after a heating step at a higher temperature.

[0334] It is preferable to use films that can be removed by wet etching or dry etching for the sacrificial film 158Rf and the mask film 159Rf.

[0335] It is preferable that the sacrificial film 158Rf formed on and in contact with the organic compound film 103Rf be formed using a formation method that causes less damage to the organic compound film 103Rf than the mask film 159Rf. For example, the ALD method (Atomic Layer Deposition method) or the vacuum evaporation method is more preferable than the sputtering method.

[0336] The sacrificial film 158Rf and the mask film 159Rf may each be made of one or more of a metal film, an alloy film, a metal oxide film, a semiconductor film, an organic insulating film, an inorganic insulating film, or the like.

[0337] The sacrificial film 158Rf and the mask film 159Rf can be made of 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 such metal materials. It is particularly preferable to use a low-melting-point material such as aluminum or silver. Using a metal material capable of blocking ultraviolet rays for one or both of the sacrificial film 158Rf and the mask film 159Rf is preferable because it can prevent the organic compound film 103Rf from being irradiated with ultraviolet rays during pattern exposure, thereby suppressing deterioration of the organic compound film 103Rf.

[0338] Furthermore, for the sacrificial film 158Rf and the mask film 159Rf, metal oxides such as In-Ga-Zn oxide, indium oxide, In-Zn oxide, In-Sn oxide, indium titanium oxide (In-Ti oxide), indium tin zinc oxide (In-Sn-Zn oxide), indium titanium zinc oxide (In-Ti-Zn oxide), indium gallium tin zinc oxide (In-Ga-Sn-Zn oxide), and indium tin oxide containing silicon can be used, respectively.

[0339] In addition, in the above metal oxide, an element M (wherein M is one or more elements selected from aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium) may be used instead of gallium.

[0340] The sacrificial film 158Rf and the mask film 159Rf are preferably made of a semiconductor material such as silicon or germanium, which has a high affinity with the semiconductor manufacturing process, or a compound containing the semiconductor material.

[0341] Moreover, various inorganic insulating films can be used for the sacrificial film 158Rf and the mask film 159Rf, respectively. In particular, an oxide insulating film is preferable because it has higher adhesion to the organic compound film 103Rf than a nitride insulating film.

[0342] 4A, a resist mask 190R is formed. The resist mask 190R can be formed by applying a photosensitive material (photoresist) and then exposing and developing it.

[0343] The resist mask 190R is provided in a position overlapping with the conductive layer 152R. The resist mask 190R is preferably provided also in a position overlapping with the conductive layer 152C, which can prevent the conductive layer 152C from being damaged during the manufacturing process of the display device.

[0344] 4(B), a resist mask 190R is used to remove a portion of the mask film 159Rf to form a mask layer 159R. The mask layer 159R remains on the conductive layer 152R and the conductive layer 152C. The resist mask 190R is then removed. The mask layer 159R is used as a mask (also referred to as a hard mask) to remove a portion of the sacrificial film 158Rf to form a sacrificial layer 158R.

[0345] By using the wet etching method, damage to the organic compound film 103Rf during processing of the sacrificial film 158Rf and the mask film 159Rf can be reduced compared to when using the dry etching method. When using the wet etching method, it is preferable to use an acid aqueous solution such as a developer, an alkaline aqueous solution such as a tetramethylammonium hydroxide aqueous solution (TMAH), or a chemical solution using dilute hydrofluoric acid, oxalic acid, phosphoric acid, acetic acid, nitric acid, or a mixture of these.

[0346] Furthermore, when dry etching is used to process the sacrificial film 158Rf, deterioration of the organic compound film 103Rf can be suppressed by not using a gas containing oxygen as the etching gas.

[0347] The resist mask 190R can be removed in the same manner as the resist mask 191.

[0348] 4(B), the organic compound film 103Rf is processed to form the organic compound layer 103R. For example, the mask layer 159R and the sacrificial layer 158R are used as a hard mask to remove a part of the organic compound film 103Rf, thereby forming the organic compound layer 103R.

[0349] 4B, a stacked structure of the organic compound layer 103R, the sacrificial layer 158R, and the mask layer 159R remains on the conductive layer 152R. Also, the conductive layers 152G and 152B are exposed.

[0350] The organic compound film 103Rf is preferably processed by anisotropic etching, particularly anisotropic dry etching, or wet etching may be used.

[0351] When dry etching is used, deterioration of the organic compound film 103Rf can be suppressed by not using an oxygen-containing gas as the etching gas.

[0352] Alternatively, an etching gas containing oxygen may be used. The etching rate can be increased by using an etching gas containing oxygen. Therefore, etching can be performed under low power conditions while maintaining a sufficiently high etching rate. This can reduce damage to the organic compound film 103Rf. Furthermore, problems such as adhesion of reaction products generated during etching can be reduced.

[0353] When dry etching is used, it is preferable to use a gas containing one or more of H, CF, C, F, SF, CHF, Cl, H, O, BCl, or Group 18 elements such as He and Ar as the etching gas. Alternatively, it is preferable to use a gas containing one or more of these elements and oxygen as the etching gas. Alternatively, oxygen gas may be used as the etching gas.

[0354] Subsequently, as shown in FIG. 5(A), an organic compound film 103Gf, which will later become the organic compound layer 103G, is formed.

[0355] The organic compound film 103Gf can be formed by the same method as that used to form the organic compound film 103Rf, and can have the same structure as the organic compound film 103Rf.

[0356] Next, as shown in FIG. 5A, a sacrificial film 158Gf and a mask film 159Gf are formed in this order. Then, a resist mask 190G is formed. The materials and forming methods of the sacrificial film 158Gf and the mask film 159Gf are the same as those applicable to the sacrificial film 158Rf and the mask film 159Rf. The materials and forming methods of the resist mask 190G are the same as those applicable to the resist mask 190R.

[0357] The resist mask 190G is provided in a position overlapping with the conductive layer 152G.

[0358] 5(B), a resist mask 190G is used to remove a portion of the mask film 159Gf to form a mask layer 159G. The mask layer 159G remains on the conductive layer 152G. The resist mask 190G is then removed. Next, using the mask layer 159G as a mask, a portion of the sacrificial film 158Gf is removed to form a sacrificial layer 158G. Next, the organic compound film 103Gf is processed to form an organic compound layer 103G.

[0359] Subsequently, as shown in FIG. 5(C), an organic compound film 103Bf is formed.

[0360] The organic compound film 103Bf can be formed by the same method as that used to form the organic compound film 103Rf, and can have the same structure as the organic compound film 103Rf.

[0361] 5(C), a sacrificial film 158Bf and a mask film 159Bf are formed in this order. 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 applicable to the sacrificial film 158Rf and the mask film 159Rf. The materials and forming methods of the resist mask 190B are the same as those applicable to the resist mask 190R.

[0362] The resist mask 190B is provided in a position overlapping with the conductive layer 152B.

[0363] 5(D), a resist mask 190B is used to remove a portion of the mask film 159Bf to form a mask layer 159B. The mask layer 159B remains on the conductive layer 152B. The resist mask 190B is then removed. The mask layer 159B is then used as a mask to remove a portion of the sacrificial film 158Bf to form a sacrificial layer 158B. The organic compound film 103Bf is then processed to form the organic compound layer 103B. For example, the mask layer 159B and the sacrificial layer 158B are used as hard masks to remove a portion of the organic compound film 103Bf to form the organic compound layer 103B.

[0364] 5D, a stacked structure of the organic compound layer 103B, the sacrificial layer 158B, and the mask layer 159B remains on the conductive layer 152B, and the mask layers 159R and 159G are exposed.

[0365] It is preferable that the side surfaces of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B are perpendicular or approximately perpendicular to the surface on which they are formed. For example, it is preferable that the angle formed between the surface on which they are formed and these side surfaces is 60 degrees or more and 90 degrees or less.

[0366] As described above, the distance between adjacent pairs of the organic compound layers 103R, 103G, and 103B formed using photolithography can be narrowed to 8 μm or less, 5 μm or less, 3 μm or less, 2 μm or less, or 1 μm or less. Here, the distance can be defined, for example, as the distance between the opposing ends of adjacent pairs of the organic compound layers 103R, 103G, and 103B. By narrowing the distance between the island-shaped organic compound layers in this manner, a display device with high definition and a large aperture ratio can be provided. Furthermore, the distance between the first electrodes of adjacent light-emitting devices can also be narrowed, for example, to 10 μm or less, 8 μm or less, 5 μm or less, 3 μm or less, or 2 μm or less. The distance between the first electrodes of adjacent light-emitting devices is preferably 2 μm or more and 5 μm or less.

[0367] Subsequently, as shown in FIG. 6(A), it is preferable to remove the mask layers 159R, 159G, and 159B.

[0368] The mask layer removal process can be performed using the same method as the mask film processing process. In particular, by using a wet etching method, damage to the organic compound layer 103 during the mask layer removal can be reduced compared to when a dry etching method is used.

[0369] The mask layer may also be removed by dissolving it in a polar solvent such as water or alcohol, such as ethyl alcohol, methyl alcohol, isopropyl alcohol (IPA), or glycerin.

[0370] After removing the mask layer, a drying treatment may be performed to remove water adsorbed on the surface. For example, a heat treatment can be performed in an inert gas atmosphere or a reduced pressure atmosphere. The heat treatment can be performed at a substrate temperature of 50°C or higher and 200°C or lower, preferably 60°C or higher and 150°C or lower, and more preferably 70°C or higher and 120°C or lower. A reduced pressure atmosphere is preferred because it allows drying at a lower temperature.

[0371] Subsequently, as shown in FIG. 6(B), an inorganic insulating film 125f is formed.

[0372] Subsequently, as shown in FIG. 6(C), an insulating film 127f, which will later become the insulating layer 127, is formed on the inorganic insulating film 125f.

[0373] 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, respectively.

[0374] As the inorganic insulating film 125f, it is preferable to form an insulating film having a thickness of 3 nm or more, 5 nm or more, or 10 nm or more, and 200 nm or less, 150 nm or less, 100 nm or less, or 50 nm or less within the above substrate temperature range.

[0375] The inorganic insulating film 125f is preferably formed by, for example, the ALD method. The ALD method is preferable because it can reduce film formation damage and also allows for the formation of a film with high coverage. The inorganic insulating film 125f is preferably formed as an aluminum oxide film by, for example, the ALD method.

[0376] The insulating film 127f is preferably formed by the wet film formation method described above. The insulating film 127f is preferably formed by, for example, spin coating using a photosensitive material, more specifically, using a photosensitive resin composition containing an acrylic resin.

[0377] Subsequently, exposure is performed to expose a part of the insulating film 127f to visible light or ultraviolet light. The insulating layer 127 is formed in a region sandwiched between any two of the conductive layers 152R, 152G, and 152B, and around the conductive layer 152C.

[0378] The exposed region of the insulating film 127f can control the width of the insulating layer 127 to be formed later. In this embodiment, the insulating layer 127 is processed so as to have a portion overlapping the upper surface of the conductive layer 151.

[0379] The light used for exposure preferably contains i-line (wavelength 365 nm), and may contain at least one of g-line (wavelength 436 nm) and h-line (wavelength 405 nm).

[0380] Subsequently, as shown in FIG. 7(A), development is carried out to remove the exposed area of the insulating film 127f, thereby forming the insulating layer 127a.

[0381] 7(B), an etching process is performed using the insulating layer 127a as a mask to remove a portion of the inorganic insulating film 125f and reduce the thickness of a portion of the sacrificial layers 158R, 158G, and 158B. As a result, the inorganic insulating layer 125 is formed below the insulating layer 127a. Furthermore, the surfaces of the thin portions of the sacrificial layers 158R, 158G, and 158B are exposed. Note that, hereinafter, the etching process using the insulating layer 127a as a mask may be referred to as the first etching process.

[0382] The first etching process can be performed by dry etching or wet etching. Note that, when the inorganic insulating film 125f is formed using the same material as the sacrificial layers 158R, 158G, and 158B, the first etching process can be performed all at once, which is preferable.

[0383] When dry etching is performed, it is preferable to use a chlorine-based gas. Examples of chlorine-based gases that can be used include Cl2, BCl3, SiCl4, and CCl4, either singly or in combination. Furthermore, oxygen gas, hydrogen gas, helium gas, and argon gas can be added to the chlorine-based gas, either singly or in combination. By using dry etching, thin-film regions of the sacrificial layers 158R, 158G, and 158B can be formed with good in-plane uniformity.

[0384] The dry etching apparatus may be a dry etching apparatus having a high-density plasma source, such as an inductively coupled plasma (ICP) etching apparatus, or a capacitively coupled plasma (CCP) etching apparatus having parallel plate electrodes.

[0385] Furthermore, it is preferable to perform the first etching process by wet etching. Using wet etching can reduce damage to the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B compared to using dry etching. For example, wet etching can be performed using an alkaline solution. For example, TMAH, which is an alkaline solution, can be used for wet etching of an aluminum oxide film. Alternatively, an acid solution containing fluoride can also be used. In this case, wet etching can be performed by a puddle method. Note that, if the inorganic insulating film 125f is formed using the same material as the sacrificial layers 158R, 158G, and 158B, the above-mentioned etching processes can be performed simultaneously, which is preferable.

[0386] In the first etching process, the sacrificial layers 158R, 158G, and 158B are not completely removed, and the etching process is stopped when the film thicknesses of the sacrificial layers 158R, 158G, and 158B are reduced. In this manner, by leaving the sacrificial layers 158R, 158G, and 158B on the organic compound layers 103R, 103G, and 103B, respectively, it is possible to prevent the organic compound layers 103R, 103G, and 103B from being damaged in subsequent processes.

[0387] Next, the entire substrate is exposed to visible light or ultraviolet light, and the insulating layer 127a is preferably irradiated with the energy density of 0 mJ / cm. 2 Larger, 800mJ / cm 2 It is preferable that the dose is 0 mJ / cm or less, and 2 Larger, 500mJ / cm 2 It is more preferable to perform the following. By performing such exposure after development, the transparency of the insulating layer 127a can be improved in some cases. Furthermore, the substrate temperature required for heat treatment to transform the insulating layer 127a into a tapered shape in a later step can be reduced in some cases.

[0388] Here, the presence of a barrier insulating layer against oxygen (e.g., an aluminum oxide film, etc.) as the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B can reduce the diffusion of oxygen into the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B.

[0389] Next, heat treatment (also referred to as post-baking) is performed. By performing the heat treatment, the insulating layer 127a can be transformed into the insulating layer 127 having tapered side surfaces (FIG. 7C). The heat treatment is performed at a temperature lower than the upper temperature limit of the organic compound layer. The heat treatment can be performed at a substrate temperature of 50° C. to 200° C., preferably 60° C. to 150° C., more preferably 70° C. to 130° C. The heating atmosphere may be an air atmosphere or an inert gas atmosphere. The heating atmosphere may be an atmospheric pressure atmosphere or a reduced-pressure atmosphere. This can improve adhesion between the insulating layer 127 and the inorganic insulating layer 125 and also improve the corrosion resistance of the insulating layer 127.

[0390] By not completely removing the sacrificial layers 158R, 158G, and 158B in the first etching process and leaving the sacrificial layers 158R, 158G, and 158B in a thinner state, the organic compound layers 103R, 103G, and 103B can be prevented from being damaged and deteriorated in the heat treatment, thereby improving the reliability of the light-emitting device.

[0391] 8(A), an etching process is performed using the insulating layer 127 as a mask to remove portions of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B. As a result, openings are formed in the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B, respectively, and the upper surfaces of the organic compound layer 103R, the organic compound layer 103G, the organic compound layer 103B, and the conductive layer 152C are exposed. Note that, hereinafter, this etching process may be referred to as a second etching process.

[0392] The end of the inorganic insulating layer 125 is covered with the insulating layer 127. Also, Fig. 8(A) shows an example in which part of the end 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.

[0393] The second etching process is performed by wet etching. By using wet etching, damage to the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B can be reduced compared to when dry etching is used. Wet etching can be performed using, for example, an alkaline solution or an acidic solution. It is preferable to use an aqueous solution so that the organic compound layer 103 does not dissolve.

[0394] 8(B), a common electrode 155 is formed on the organic compound layer 103R, the organic compound layer 103G, the organic compound layer 103B, the conductive layer 152C, and the insulating layer 127. The common electrode 155 can be formed by a method such as sputtering or vacuum deposition.

[0395] 8(C), a protective layer 131 is formed on the common electrode 155. The protective layer 131 can be formed by a method such as a vacuum deposition method, a sputtering method, a CVD method, or an ALD method.

[0396] Subsequently, the substrate 120 is attached over 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 of one embodiment of the present invention, the insulating layer 156 is provided so as to have a region overlapping with a side surface of the conductive layer 151, and the conductive layer 152 is formed so as to cover the conductive layer 151 and the insulating layer 156. This can increase the yield of the display device and suppress the occurrence of defects.

[0397] As described above, in the manufacturing method of a display device according to one embodiment of the present invention, the island-shaped organic compound layers 103R, 103G, and 103B are formed by forming films over the entire surface and then processing them, rather than using a fine metal mask. This allows the island-shaped layers to be formed with uniform thicknesses. This allows a high-resolution display device or a display device with a high aperture ratio to be realized. Furthermore, even when the resolution or aperture ratio is high and the distance between subpixels is extremely short, the organic compound layers 103R, 103G, and 103B can be prevented from contacting each other in adjacent subpixels. Therefore, leakage current between subpixels can be suppressed. This prevents crosstalk and realizes a display device with extremely high contrast. Furthermore, even in a display device including tandem light-emitting devices fabricated by photolithography, a display device with excellent characteristics can be provided.

[0398] (Fourth embodiment) In this embodiment, a display device according to one embodiment of the present invention will be described.

[0399] The display device of the present embodiment can be a high-definition display device, and can therefore be used as a display unit for information terminals (wearable devices) such as wristwatches and bracelets, as well as for wearable devices that can be worn on the head, such as VR devices such as head-mounted displays (HMDs) and AR devices such as glasses.

[0400] The display device of the present embodiment can be a high-resolution display device or a large-sized display device. Therefore, the display device of the present embodiment can be used in electronic devices having relatively large screens, such as television devices, desktop or notebook personal computers, computer monitors, digital signage, and large game machines such as pachinko machines, as well as in the display units of digital cameras, digital video cameras, digital photo frames, mobile phones, portable game machines, personal digital assistants, and sound reproducing devices.

[0401] [Display module] 9A shows a perspective view of a display module 280. The display module 280 includes a display device 100A and an FPC 290. Note that the display device included in the display module 280 is not limited to the display device 100A, and may be any of display devices 100B to 100E described later.

[0402] The display module 280 has a substrate 291 and a substrate 292. The display module 280 has a display unit 281. The display unit 281 is a region that displays an image in the display module 280, and is a region where light from each pixel provided in a pixel unit 284 (described later) can be viewed.

[0403] 9(B) is a perspective view schematically showing the configuration on the substrate 291 side. A circuit portion 282, a pixel circuit portion 283 on the circuit portion 282, and a pixel portion 284 on the pixel circuit portion 283 are stacked on the substrate 291. A terminal portion 285 for connecting to an FPC 290 is provided in a portion of the substrate 291 that does not overlap with the pixel portion 284. The terminal portion 285 and the circuit portion 282 are electrically connected by a wiring portion 286 composed of a plurality of wirings.

[0404] The pixel section 284 has a plurality of periodically arranged pixels 284a. An enlarged view of one pixel 284a is shown on the right side of Fig. 9(B). The various configurations described in the previous embodiments can be applied to the pixel 284a.

[0405] The pixel circuit section 283 has a plurality of pixel circuits 283a arranged periodically.

[0406] One pixel circuit 283a is a circuit that controls the driving of a plurality of elements included in one pixel 284a.

[0407] The circuit portion 282 includes a circuit for driving each pixel circuit 283a of the pixel circuit portion 283. For example, it is preferable that the circuit portion 282 includes one or both of a gate line driver circuit and a source line driver circuit. In addition, the circuit portion 282 may include at least one of an arithmetic circuit, a memory circuit, a power supply circuit, and the like.

[0408] The FPC 290 functions as wiring for supplying a video signal, a power supply potential, or the like from the outside to the circuit section 282. An IC may be mounted on the FPC 290.

[0409] The display module 280 can be configured such that one or both of the pixel circuit unit 283 and the circuit unit 282 are stacked below the pixel unit 284, thereby making it possible to extremely increase the aperture ratio (effective display area ratio) of the display unit 281.

[0410] Such a display module 280 has extremely high resolution and can therefore be suitably used in VR devices such as HMDs or glasses-type AR devices. For example, even in a configuration in which the display unit of the display module 280 is viewed through lenses, the display module 280 has an extremely high-resolution display unit 281, so that even if the display unit is enlarged with the lenses, the pixels are not visible, allowing for a highly immersive display. Furthermore, the display module 280 is not limited to this and can be suitably used in electronic devices having relatively small display units.

[0411] [Display device 100A] The display device 100A shown in FIG. 10A includes a substrate 301, a light-emitting device 130R, a light-emitting device 130G, a light-emitting device 130B, a capacitor 240, and a transistor 310.

[0412] The substrate 301 corresponds to the substrate 291 in FIGS. 10A and 10B. The transistor 310 has a channel formation region in the substrate 301. The substrate 301 can be, for example, a semiconductor substrate such as a single crystal silicon substrate. The transistor 310 includes a part of the substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 functions as a gate electrode. The insulating layer 313 is located between the substrate 301 and the conductive layer 311 and functions as a gate insulating layer. The low-resistance region 312 is a region in which the substrate 301 is doped with impurities and functions as a source or drain. The insulating layer 314 is provided to cover a side surface of the conductive layer 311.

[0413] Furthermore, an element isolation layer 315 is provided between two adjacent transistors 310 so as to be embedded in the substrate 301 .

[0414] In addition, an insulating layer 261 is provided to cover the transistor 310 , and a capacitor 240 is provided on the insulating layer 261 .

[0415] Capacitor 240 has conductive layer 241, conductive layer 245, and insulating layer 243 located therebetween. Conductive layer 241 functions as one electrode of capacitor 240, conductive layer 245 functions as the other electrode of capacitor 240, and insulating layer 243 functions as a dielectric of capacitor 240.

[0416] The conductive layer 241 is provided over the insulating layer 261 and is buried in the insulating layer 254. The conductive layer 241 is electrically connected to one of the source and drain of the transistor 310 by a plug 271 buried in the insulating layer 261. The insulating layer 243 is provided to cover the conductive layer 241. The conductive layer 245 is provided in a region overlapping with the conductive layer 241 with the insulating layer 243 interposed therebetween.

[0417] 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. Light-emitting device 130R, light-emitting device 130G, and light-emitting device 130B are provided on the insulating layer 175. An insulator is provided in the region between adjacent light-emitting devices.

[0418] An insulating layer 156R is provided to have a region overlapping with a side surface of the conductive layer 151R, an insulating layer 156G is provided to have a region overlapping with a side surface of the conductive layer 151G, and an insulating layer 156B is provided to have a region overlapping with a side surface of the conductive layer 151B. Furthermore, a conductive layer 152R is provided to cover the conductive layer 151R and the insulating layer 156R, a conductive layer 152G is provided to cover the conductive layer 151G and the insulating layer 156G, and a conductive layer 152B is provided to cover the conductive layer 151B and the insulating layer 156B. A sacrificial layer 158R is located on the organic compound layer 103R, a sacrificial layer 158G is located on the organic compound layer 103G, and a sacrificial layer 158B is located on the organic compound layer 103B.

[0419] The conductive layer 151R, the conductive layer 151G, and the conductive layer 151B are electrically connected to one of the source and drain of the transistor 310 via an insulating layer 243, an insulating layer 255, an insulating layer 174, a plug 256 embedded in the insulating layer 175, a conductive layer 241 embedded in the insulating layer 254, and a plug 271 embedded in the insulating layer 261. Various conductive materials can be used for the plug.

[0420] Furthermore, a protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. A substrate 120 is bonded to the protective layer 131 with a resin layer 122. For details of the components from the light-emitting devices 130 to the substrate 120, refer to Embodiment 3. The substrate 120 corresponds to the substrate 292 in FIG. 9(A).

[0421] Fig. 10(B) is a modified example of the display device 100A shown in Fig. 10(A). The display device shown in Fig. 10(B) has a colored layer 132R, a colored layer 132G, and a colored layer 132B, and the light-emitting device 130 has an area where it overlaps with one of the colored layer 132R, the colored layer 132G, and the colored layer 132B. In the display device shown in Fig. 10(B), the light-emitting device 130 can emit, for example, white light. Furthermore, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light.

[0422] [Display device 100B] FIG. 11 shows a perspective view of the display device 100B, and FIG. 12 shows a cross-sectional view of the display device 100C.

[0423] The display device 100B has a configuration in which a substrate 352 and a substrate 351 are bonded together. In Fig. 11, the substrate 352 is indicated by a dashed line.

[0424] The display device 100B has a pixel unit 177, a connection unit 140, a circuit 356, wiring 355, etc. Fig. 11 shows an example in which an IC 354 and an FPC 353 are mounted on the display device 100B. Therefore, the configuration shown in Fig. 11 can also be called a display module having the display device 100B, an IC (integrated circuit), and an FPC. Here, a display device having a connector such as an FPC attached to a substrate, or a display device having an IC mounted on the substrate, is called a display module.

[0425] The connection section 140 is provided outside the pixel section 177. There may be one or more connection sections 140. The connection section 140 electrically connects the common electrode of the light-emitting device and the conductive layer, and can supply a potential to the common electrode.

[0426] The circuit 356 can be, for example, a scanning line driver circuit.

[0427] The wiring 355 has a function of supplying signals and power to the pixel portion 177 and the circuit 356. The signals and power are input to the wiring 355 from the outside via the FPC 353 or from the IC 354.

[0428] 11 shows an example in which an IC 354 is provided on a substrate 351 by a COG (Chip On Glass) method or a COF (Chip on Film) method. The IC 354 may be, for example, an IC having a scanning line driver circuit or a signal line driver circuit. The display device 100B and the display module may not necessarily include an IC. Alternatively, the IC may be mounted on an FPC by, for example, a COF method.

[0429] Figure 12 shows an example of a cross section of the display device 100B in Figure 11, where part of the area including the FPC 353, part of the circuit 356, part of the pixel section 177, part of the connection section 140, and part of the area including the end portion are cut away, as display device 100C.

[0430] [Display device 100C] The display device 100C shown in Figure 12 has, between substrate 351 and substrate 352, transistor 201, transistor 205, light-emitting device 130R that emits red light, light-emitting device 130G that emits green light, and light-emitting device 130B that emits blue light, etc.

[0431] For details of the light emitting devices 130R, 130G, and 130B, refer to the third embodiment.

[0432] Light-emitting device 130R has conductive layer 224R, conductive layer 151R on conductive layer 224R, and conductive layer 152R on conductive layer 151R. Light-emitting device 130G has conductive layer 224G, conductive layer 151G on conductive layer 224G, and conductive layer 152G on conductive layer 151G. Light-emitting device 130B has conductive layer 224B, conductive layer 151B on conductive layer 224B, and conductive layer 152B on conductive layer 151B.

[0433] The conductive layer 224R is connected to the conductive layer 222b of the transistor 205 through an opening provided in the insulating layer 214. An end of the conductive layer 151R is located outside an end of the conductive layer 224R. An insulating layer 156R is provided to have a region in contact with a side surface of the conductive layer 151R, and a conductive layer 152R is provided to cover the conductive layer 151R and the insulating layer 156R.

[0434] Conductive layer 224G, conductive layer 151G, conductive layer 152G, and insulating layer 156G in light-emitting device 130G, and conductive layer 224B, conductive layer 151B, conductive layer 152B, and insulating layer 156B in light-emitting device 130B are similar to conductive layer 224R, conductive layer 151R, conductive layer 152R, and insulating layer 156R in light-emitting device 130R, and therefore detailed description thereof will be omitted.

[0435] Recesses are formed in the conductive layers 224R, 224G, and 224B so as to cover the openings provided in the insulating layer 214. A layer 128 is buried in the recesses.

[0436] Layer 128 has the function of filling in recesses in conductive layer 224R, conductive layer 224G, and conductive layer 224B and planarizing the surface. Conductive layers 151R, 151G, and 151B, which are electrically connected to conductive layer 224R, conductive layer 224G, and conductive layer 224B, are provided on conductive layer 224R, conductive layer 224G, and conductive layer 224B and layer 128. Therefore, the regions overlapping with the recesses in conductive layer 224R, conductive layer 224G, and conductive layer 224B can also be used as light-emitting regions, thereby increasing the aperture ratio of the pixel.

[0437] The layer 128 may be an insulating layer or a conductive layer. Various inorganic insulating materials, organic insulating materials, and conductive materials can be used for the layer 128 as appropriate. In particular, the layer 128 is preferably formed using an insulating material, and is particularly preferably formed using an organic insulating material. For example, the organic insulating materials that can be used for the insulating layer 127 described above can be used for the layer 128.

[0438] A protective layer 131 is provided on the light-emitting device 130R, the light-emitting device 130G, and the light-emitting device 130B. The protective layer 131 and the substrate 352 are bonded via an adhesive layer 142. A light-shielding layer 157 is provided on the substrate 352. A solid sealing structure, a hollow sealing structure, or the like can be applied to seal the light-emitting device 130. In FIG. 12, the space between the substrate 352 and the substrate 351 is filled with the adhesive layer 142, and a solid sealing structure is applied. Alternatively, the space may be filled with an inert gas (nitrogen, argon, etc.), and a hollow sealing structure may be applied. In this case, the adhesive layer 142 may be provided so as not to overlap with the light-emitting device. Alternatively, the space may be filled with a resin different from the frame-shaped adhesive layer 142.

[0439] 12 shows an example in which connecting portion 140 has conductive layer 224C obtained by processing the same conductive film as conductive layers 224R, 224G, and 224B, conductive layer 151C obtained by processing the same conductive film as conductive layers 151R, 151G, and 151B, and conductive layer 152C obtained by processing the same conductive film as conductive layers 152R, 152G, and 152B. Also shown in FIG. 12 is an example in which insulating layer 156C is provided so as to have a region overlapping with a side surface of conductive layer 151C.

[0440] The display device 100C is a top-emission type. Light emitted by the light-emitting device is emitted toward the substrate 352. The substrate 352 is preferably made of a material that is highly transparent to visible light. The pixel electrodes contain a material that reflects visible light, and the counter electrode (common electrode 155) contains a material that transmits visible light.

[0441] An insulating layer 211, an insulating layer 213, an insulating layer 215, and an insulating layer 214 are provided over the substrate 351 in this order. A part of the insulating layer 211 functions as a gate insulating layer for each transistor. A part of the insulating layer 213 functions as a gate insulating layer for each transistor. The insulating layer 215 is provided to cover the transistor. The insulating layer 214 is provided to cover the transistor and functions as a planarization layer. Note that the number of gate insulating layers and the number of insulating layers covering the transistors are not limited, and each may be a single layer or two or more layers.

[0442] The insulating layers 211, 213, and 215 are each preferably formed using an inorganic insulating film.

[0443] The insulating layer 214, which functions as a planarizing layer, is preferably an organic insulating layer.

[0444] The transistor 201 and the transistor 205 each include a conductive layer 221 functioning as a gate, an insulating layer 211 functioning as a gate insulating layer, a conductive layer 222a and a conductive layer 222b functioning as a source and a drain, a semiconductor layer 231, an insulating layer 213 functioning as a gate insulating layer, and a conductive layer 223 functioning as a gate.

[0445] A connection portion 204 is provided in a region of the substrate 351 where the substrate 352 does not overlap. In the connection portion 204, a source electrode or a drain electrode of the transistor 201 is electrically connected to the FPC 353 via a conductive layer 166 and a connection layer 242. The conductive layer 166 has an example of a stacked structure including a conductive film obtained by processing the same conductive film as the conductive layers 224R, 224G, and 224B, a conductive film obtained by processing the same conductive film as the conductive layers 151R, 151G, and 151B, and a conductive film obtained by processing the same conductive film as the conductive layers 152R, 152G, and 152B. The conductive layer 166 is exposed on the top surface of the connection portion 204. This allows the connection portion 204 and the FPC 353 to be electrically connected via the connection layer 242.

[0446] It is preferable to provide a light-shielding layer 157 on the surface of the substrate 352 facing the substrate 351. The light-shielding layer 157 can be provided between adjacent light-emitting devices, on the connection section 140, on the circuit 356, etc. Also, various optical members can be arranged on the outside of the substrate 352.

[0447] The substrate 351 and the substrate 352 can be made of the same material as can be used for the substrate 120 .

[0448] The adhesive layer 142 can be made of a material that can be used for the resin layer 122 .

[0449] The connection layer 242 may be an anisotropic conductive film (ACF), an anisotropic conductive paste (ACP), or the like.

[0450] [Display device 100D] The display device 100D shown in FIG. 13 differs from the display device 100C shown in FIG. 12 mainly in that it is a bottom-emission display device.

[0451] Light emitted from the light emitting device is emitted toward the substrate 351. It is preferable that a material with high transparency to visible light is used for the substrate 351. On the other hand, the light transparency of the material used for the substrate 352 is not an issue.

[0452] A light-shielding layer 317 is preferably formed between the substrate 351 and the transistor 201 and between the substrate 351 and the transistor 205. Figure 13 shows an example in which the light-shielding layer 317 is provided over the substrate 351, the insulating layer 153 is provided over the light-shielding layer 317, and the transistors 201, 205, etc. are provided over the insulating layer 153.

[0453] Light emitting device 130R includes conductive layer 112R, conductive layer 126R on conductive layer 112R, and conductive layer 129R on conductive layer 126R.

[0454] Light emitting device 130B includes conductive layer 112B, conductive layer 126B on conductive layer 112B, and conductive layer 129B on conductive layer 126B.

[0455] The conductive layers 112R, 112B, 126R, 126B, 129R, and 129B are each made of a material that is highly transparent to visible light. The second electrode 102 is preferably made of a material that reflects visible light.

[0456] Although the light emitting device 130G is not shown in FIG. 13, the light emitting device 130G is also provided.

[0457] Although FIG. 13 and other figures show an example in which the top surface of the layer 128 has a flat portion, the shape of the layer 128 is not particularly limited.

[0458] [Display device 100D2] The display device 100D2 shown in Fig. 14 is an example of a bottom-emission type display device that differs from the display device 100D shown in Fig. 13. The display device 100D2 differs from the display device 100D in that it has an organic resin layer 180. Note that in the drawing, the reference numerals of the same components as those in Fig. 13 may be omitted, and the description in Fig. 13 may be referred to for details.

[0459] 14(B) shows a top view layout of pixel 178 (pixel 178a and pixel 178b) having subpixels 110 (subpixels 110R, 110G, 110B, and 110W), and FIG. 14(C) shows a top view of organic resin layer 180 in a region where subpixels 110R and 110G of pixel 178 are formed. Note that the distance between light-shielding layers 317 is 110Rw in the light-emitting region of subpixel 110R.

[0460] As shown in FIG. 14(A), the organic resin layer 180 is provided on the insulating layer 214. As shown in the region surrounded by the dashed line in FIG. 14(A) and in FIG. 14(C), the organic resin layer 180 has curved recesses 181 (recesses 181a and 181b) at least in the region where the subpixels are formed. Note that the recesses 181 may be provided outside the light-emitting region, such as recess 181c. Providing recess 181c refracts light emitted in the region overlapping with the light-shielding layer 317 or light traveling to the region overlapping with the light-shielding layer 317, allowing it to be extracted from the light-emitting region, thereby improving light-emitting efficiency.

[0461] A plurality of recesses 181 may be formed in a matrix. Recesses 181a and 181b may be provided in contact with each other, or may have a flat surface between them.

[0462] 14, the recess has a hexagonal top surface shape (FIG. 14(C)) and a semicircular cross-sectional shape (FIG. 14(A)), but other shapes may be used as needed. For example, the recess may have a top surface shape such as a triangle, a quadrangle (including a rectangle and a square), a pentagon, or other polygon, a polygon with rounded corners, an ellipse, or a circle.

[0463] An insulating layer containing an organic material can be used as the organic resin layer 180. For example, acrylic resin, polyimide resin, epoxy resin, imide resin, polyamide resin, polyimideamide resin, silicone resin, siloxane resin, benzocyclobutene resin, phenol resin, precursors of these resins, etc. can be used as the organic resin layer 180. Alternatively, organic materials such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerin, pullulan, water-soluble cellulose, or alcohol-soluble polyamide resin can be used as the organic resin layer 180.

[0464] Furthermore, a photosensitive resin can be used as the organic resin layer 180. A photoresist can be used as the photosensitive resin. The photosensitive resin can be a positive type material or a negative type material.

[0465] The organic resin layer 180 may contain a material that absorbs visible light. For example, the organic resin layer 180 itself may be made of a material that absorbs visible light, or the organic resin layer 180 may contain a pigment that absorbs visible light. For example, the organic resin layer 180 may be made of a resin that can be used as a color filter that transmits red, blue, or green light and absorbs other light, or a resin that contains carbon black as a pigment and functions as a black matrix.

[0466] In addition, a first electrode 101 (a first electrode 101R and a first electrode 101W) is provided on the organic resin layer 180, and an organic compound layer 103 is provided on the first electrode 101. Ends of the first electrode 101 and the organic compound layer 103 may be covered with an insulating layer 127.

[0467] Furthermore, the first electrode 101 formed on the organic resin layer 180 has a recess similar to the recess of the organic resin layer 180. Furthermore, the organic compound layer 103 formed on the first electrode 101 has a recess similar to the recess of the first electrode 101. Furthermore, the common layer 104 formed on the organic compound layer 103 has a recess similar to the recess of the organic compound layer 103. Furthermore, the second electrode 102 formed on the common layer 104 has a recess similar to the recess of the common layer 104. That is, the recesses of the organic resin layer 180, the first electrode 101, the organic compound layer 103, the common layer 104, and the second electrode 102 have a structure in which they overlap one another.

[0468] In addition, a common layer 104 is provided over the organic compound layer 103 and the insulating layer 127, and a second electrode 102 is provided over the common layer 104. A protective layer 131 is provided over the second electrode 102, and the second electrode 102 is bonded to a substrate 352 via an adhesive layer 142.

[0469] Although light emitting device 130G and light emitting device 130B are not shown in FIG. 14, light emitting device 130G and light emitting device 130B are also provided.

[0470] The light-emitting device of one embodiment of the present invention having the organic resin layer 180 as described above contains the organic compound represented by general formula (G1) in the organic compound layer 103 as described in Embodiment 1. Therefore, due to the effect of the organic resin layer 180 and the effect of the organic semiconductor device using the organic compound of the present invention being inseparably integrated, an organic semiconductor device with high emission efficiency can be provided. Therefore, an organic semiconductor device with good reliability, low driving voltage, and low power consumption can be provided.

[0471] [Display device 100E] The display device 100E shown in FIG. 15 is a modification of the display device 100C shown in FIG. 12, and differs from the display device 100C mainly in that it has colored layers 132R, 132G, and 132B.

[0472] In the display device 100E, the light-emitting device 130 has an area that overlaps one of the colored layer 132R, the colored layer 132G, and the colored layer 132B. The colored layer 132R, the colored layer 132G, and the colored layer 132B can be provided on the surface of the substrate 352 facing the substrate 351. An end of the colored layer 132R, an end of the colored layer 132G, and an end of the colored layer 132B can overlap the light-shielding layer 157.

[0473] In the display device 100E, the light-emitting device 130 can emit, for example, white light. Furthermore, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light. The display device 100E may be configured such that the colored layers 132R, 132G, and 132B are provided between the protective layer 131 and the adhesive layer 142.

[0474] [Display device 100E2] The display device 100E2 shown in Fig. 16 is a modified example of the display device 100E shown in Fig. 15, and has microlenses 182 on the colored layers 132R, 132G, and 132B. Note that in the figure, the reference numerals of the same components as those in Fig. 15 may be omitted, and for details, the description in Fig. 15 may be referred to.

[0475] 16(B) shows a top view layout of a pixel 178 (pixel 178a and pixel 178b) having subpixels 110 (subpixels 110R, 110G, and 110B), and FIG. 16(C) shows a top view of a microlens 182 in a region where the subpixels 110R and 110G of the pixel 178 are formed. The region where the common electrode 155 and the organic compound layer 103 are in contact has a width 110Gw in the light-emitting region of the subpixel 110G.

[0476] 16(A) has a planarization film 143 on a protective layer 131, and colored layers 132R, 132G, and 132B on the planarization film 144. The planarization film 144 is provided so as to cover the colored layers 132R, 132G, and 132B. A microlens 182 is provided on the planarization film 144.

[0477] As shown in FIG. 16C, the microlens 182 may be provided for each sub-pixel in a region where the sub-pixel is formed.

[0478] 16(C), the top surface shape of the microlens 182 is shown as a hexagon, but other shapes may be used as needed. For example, the top surface shape of the recess may be a polygon such as a triangle, a quadrangle (including a rectangle and a square), a pentagon, or any of these polygons with rounded corners, an ellipse, or a circle.

[0479] The microlenses 182 can be formed using the same material as the organic resin layer 180 .

[0480] The light-emitting device of one embodiment of the present invention having the above-described microlens 182 contains the organic compound represented by the general formula (G1) in the organic compound layer 103 as described in Embodiment 1. Therefore, an organic semiconductor device with high emission efficiency can be provided due to the effect of the microlens 182 and the effect of the organic semiconductor device using the organic compound of the present invention being inseparably integrated. Therefore, an organic semiconductor device with good reliability, low driving voltage, and low power consumption that is optimal for a mobile display can be provided.

[0481] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate.

[0482] (Embodiment 5) In this embodiment, an electronic device according to one embodiment of the present invention will be described.

[0483] The electronic devices of this embodiment include the display device of one embodiment of the present invention in a display portion. The display device of one embodiment of the present invention has low power consumption and high reliability. Therefore, the display device of one embodiment of the present invention can be used in the display portion of various electronic devices.

[0484] Examples of electronic devices include electronic devices with relatively large screens such as television sets, desktop or notebook personal computers, computer monitors, digital signage, large game machines such as pachinko machines, as well as digital cameras, digital video cameras, digital photo frames, mobile phones, portable game machines, personal digital assistants, and sound playback devices.

[0485] An example of a wearable device that can be worn on the head will be described with reference to FIGS. 17(A) to 17(D).

[0486] The electronic device 700A shown in FIG. 17(A) and the electronic device 700B shown in FIG. 17(B) each have a pair of display panels 751, a pair of housings 721, a communication unit (not shown), a pair of mounting units 723, a control unit (not shown), an imaging unit (not shown), a pair of optical members 753, a frame 757, and a pair of nose pads 758.

[0487] The display device of one embodiment of the present invention can be applied to the display panel 751. Therefore, the electronic device can be highly reliable.

[0488] The electronic device 700A and the electronic device 700B can each project an image displayed on the display panel 751 onto a display area 756 of the optical member 753. Because the optical member 753 is translucent, the user can see the image displayed in the display area superimposed on a transmitted image visible through the optical member 753.

[0489] Electronic device 700A and electronic device 700B may be provided with a camera capable of capturing an image in front of them as an imaging unit. Furthermore, electronic device 700A and electronic device 700B may each be provided with an acceleration sensor such as a gyro sensor, thereby detecting the orientation of the user's head and displaying an image corresponding to that orientation in display area 756.

[0490] The communication unit has a wireless communication device, and can supply, for example, a video signal via the wireless communication device. Note that instead of or in addition to the wireless communication device, a connector to which a cable through which a video signal and a power supply potential can be connected may be provided.

[0491] Furthermore, the electronic device 700A and the electronic device 700B are provided with batteries, which can be charged wirelessly and / or by wire.

[0492] The housing 721 may be provided with a touch sensor module.

[0493] Various touch sensors can be used as the touch sensor module. For example, various types of touch sensors can be used, such as a capacitance type, a resistive film type, an infrared type, an electromagnetic induction type, a surface acoustic wave type, or an optical type. In particular, it is preferable to use a capacitance type or an optical type sensor in the touch sensor module.

[0494] The electronic device 800A shown in Figure 17(C) and the electronic device 800B shown in Figure 17(D) each have a pair of display units 820, a housing 821, a communication unit 822, a pair of mounting units 823, a control unit 824, a pair of imaging units 825, and a pair of lenses 832.

[0495] The display device of one embodiment of the present invention can be applied to the display portion 820. Therefore, the electronic device can be highly reliable.

[0496] Display unit 820 is provided inside housing 821 at a position that can be viewed through lens 832. Also, by displaying different images on the pair of display units 820, it is possible to perform a three-dimensional display using parallax.

[0497] It is preferable that electronic device 800A and electronic device 800B each have a mechanism that allows the left and right positions of lens 832 and display unit 820 to be adjusted so that they are optimally positioned according to the position of the user's eyes.

[0498] The wearing part 823 allows the user to wear the electronic device 800A or the electronic device 800B on the head.

[0499] The imaging unit 825 has a function of acquiring external information. Data acquired by the imaging unit 825 can be output to the display unit 820. An image sensor can be used for the imaging unit 825. Furthermore, multiple cameras may be provided to support multiple angles of view, such as telephoto and wide angle.

[0500] The electronic device 800A may have a vibration mechanism that functions as a bone conduction earphone.

[0501] The electronic device 800A and the electronic device 800B may each have an input terminal to which a cable can be connected for supplying a video signal from a video output device or the like and power for charging a battery provided in the electronic device.

[0502] The electronic device of one embodiment of the present invention may have a function of wirelessly communicating with the earphone 750 .

[0503] 17B includes an earphone unit 727. A part of the wiring connecting the earphone unit 727 and a control unit may be disposed inside the housing 721 or the attachment unit 723.

[0504] 17(D) includes an earphone unit 827. For example, the earphone unit 827 and the control unit 824 can be configured to be connected to each other by wire.

[0505] As described above, the electronic devices of one embodiment of the present invention are preferably either glasses-type devices (such as the electronic devices 700A and 700B) or goggle-type devices (such as the electronic devices 800A and 800B).

[0506] An electronic device 6500 shown in FIG. 18A is a portable information terminal that can be used as a smartphone.

[0507] The electronic device 6500 includes a housing 6501, a display portion 6502, a power button 6503, a button 6504, a speaker 6505, a microphone 6506, a camera 6507, and a light source 6508. The display portion 6502 has a touch panel function.

[0508] The display device of one embodiment of the present invention can be applied to the display portion 6502. Therefore, the electronic device can be highly reliable.

[0509] FIG. 18B is a schematic cross-sectional view including the end portion of the housing 6501 on the microphone 6506 side.

[0510] A light-transmitting protective member 6510 is provided on the display surface side of the housing 6501, and a display panel 6511, optical members 6512, a touch sensor panel 6513, a printed circuit board 6517, a battery 6518, etc. are arranged in the space surrounded by the housing 6501 and the protective member 6510.

[0511] A display panel 6511, an optical member 6512, and a touch sensor panel 6513 are fixed to the protective member 6510 by adhesive layers (not shown).

[0512] In an area outside the display unit 6502, a part of the display panel 6511 is folded back, and an FPC 6515 is connected to the folded back part. An IC 6516 is mounted on the FPC 6515. The FPC 6515 is connected to a terminal provided on a printed circuit board 6517.

[0513] The display device of one embodiment of the present invention can be applied to the display panel 6511. Therefore, an extremely lightweight electronic device can be realized. Furthermore, since the display panel 6511 is extremely thin, a large-capacity battery 6518 can be mounted thereon while keeping the thickness of the electronic device small. Furthermore, by folding back a part of the display panel 6511 and arranging a connection portion with the FPC 6515 on the back side of the pixel portion, an electronic device with a narrow frame can be realized.

[0514] 18C shows an example of a television set. A television set 7100 includes a display portion 7000 built in a housing 7171. Here, the housing 7171 is supported by a stand 7173.

[0515] The display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can be highly reliable.

[0516] The television set 7100 shown in FIG. 18C can be operated using an operation switch provided on a housing 7171 and a separate remote control 7151.

[0517] 18D shows an example of a laptop personal computer 7200. The laptop personal computer 7200 includes a housing 7211, a keyboard 7212, a pointing device 7213, and an external connection port 7214. The housing 7211 includes a display portion 7000.

[0518] The display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can be highly reliable.

[0519] 18(E) and 18(F) show an example of digital signage.

[0520] 18E includes a housing 7301, a display portion 7000, and a speaker 7303. The digital signage 7300 may further include an LED lamp, operation keys (including a power switch or an operation switch), a connection terminal, various sensors, a microphone, and the like.

[0521] 18F shows a digital signage 7400 attached to a cylindrical pillar 7401. The digital signage 7400 has a display unit 7000 provided along the curved surface of the pillar 7401.

[0522] 18E and 18F, the display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can have high reliability.

[0523] The larger the display unit 7000, the more information can be provided at one time. Also, the larger the display unit 7000, the more easily it will attract people's attention, which can increase the advertising effectiveness of, for example, advertisements.

[0524] Furthermore, as shown in Figures 18(E) and 18(F), it is preferable that the digital signage 7300 or the digital signage 7400 be able to wirelessly communicate with an information terminal 7311 or an information terminal 7411 such as a smartphone carried by a user.

[0525] The electronic devices shown in Figures 19(A) to 19(G) include a housing 9000, a display portion 9001, a speaker 9003, operation keys 9005 (including a power switch or an operation switch), a connection terminal 9006, a sensor 9007 (including a function to measure force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), a microphone 9008, etc.

[0526] 19(A) to 19(G) have various functions, such as a function to display various information (still images, videos, text images, etc.) on a display unit, a touch panel function, a function to display a calendar, date, time, etc., a function to control processing by various software (programs), a wireless communication function, a function to read and process programs or data recorded on a recording medium, etc.

[0527] The electronic devices shown in FIGS. 19A to 19G will be described in detail below.

[0528] FIG. 19A is a perspective view showing a mobile information terminal 9171. The mobile information terminal 9171 can be used as, for example, a smartphone. The mobile information terminal 9171 may be provided with a speaker 9003, a connection terminal 9006, a sensor 9007, or the like. The mobile information terminal 9171 can display text and image information on multiple surfaces thereof. FIG. 19A shows an example in which three icons 9050 are displayed. Information 9051 indicated by a dashed rectangle can also be displayed on another surface of the display unit 9001. Examples of the information 9051 include notification of an incoming email, SNS, phone call, etc., the title of the email or SNS, the sender's name, the date and time, the remaining battery level, and radio wave intensity. Alternatively, the icon 9050 or the like may be displayed in the position where the information 9051 is displayed.

[0529] 19B is a perspective view of a mobile information terminal 9172. The mobile information terminal 9172 has a function of displaying information on three or more surfaces of the display portion 9001. Here, an example is shown in which information 9052, information 9053, and information 9054 are displayed on different surfaces. For example, a user can check information 9053 displayed in a position where the mobile information terminal 9172 can be observed from above while the mobile information terminal 9172 is placed in a breast pocket of clothes.

[0530] 19(C) is a perspective view of a tablet terminal 9173. The tablet terminal 9173 is capable of executing various applications such as mobile phone calls, e-mails, document browsing and creation, music playback, internet communication, and computer games. The tablet terminal 9173 has a display portion 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front side of a housing 9000, operation keys 9005 as operation buttons on the left side of the housing 9000, and a connection terminal 9006 on the bottom.

[0531] 19(D) is a perspective view showing a wristwatch-type mobile information terminal 9200. The mobile information terminal 9200 can be used as, for example, a smart watch (registered trademark). The display surface of the display portion 9001 is curved, and display can be performed along the curved display surface. The mobile information terminal 9200 can also perform hands-free conversation by communicating with, for example, a headset capable of wireless communication. The mobile information terminal 9200 can also perform data transmission and reception with another information terminal and charge itself through a connection terminal 9006. Note that charging may be performed by wireless power supply.

[0532] 19(E) to 19(G) are perspective views showing a foldable mobile information terminal 9201. FIG. 19(E) shows the mobile information terminal 9201 in an unfolded state, FIG. 19(G) shows it in a folded state, and FIG. 19(F) is a perspective view showing a state in the process of changing from one of FIG. 19(E) and FIG. 19(G) to the other. The mobile information terminal 9201 is highly portable when folded, and has a seamless, wide display area when unfolded, providing excellent viewability of the display. A display portion 9001 of the mobile information terminal 9201 is supported by three housings 9000 connected by hinges 9055. For example, the display portion 9001 can be bent with a curvature radius of 0.1 mm to 150 mm.

[0533] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate. [Example]

[0534] Synthesis Example 1 This synthesis example describes a synthesis method for N-(biphenyl-4-yl)-N-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)spiro[9H-fluorene-9,9'-[9H]xanthene]-2'-amine (abbreviation: SFxBiBnf), shown as structural formula (122) in Embodiment 1. The structural formula of SFxBiBnf is shown below.

[0535] [ka]

[0536] <Step 1: Synthesis of tert-butyl (6-phenyl-benzo[b]naphtho[1,2-d]furanyl)-8-carbamate> A 1 L three-neck flask was charged with 21 g (50 mmol) of 8-iodo-6-phenyl-benzo[b]naphtho[1,2-d]furan, 7.0 g (60 mmol) of tert-butyl carbamate, 0.58 g (1.0 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 33 g (0.10 mol) of cesium carbonate, and 250 mL of 1,4-dioxane. The system was then purged with nitrogen. 0.46 g (0.50 mmol) of tris(dibenzylideneacetone)dipalladium(0) was added and the mixture was heated to reflux for 8 hours. After cooling, the 1,4-dioxane was removed from the resulting mixture by distillation under reduced pressure. 0.40 L of ethyl acetate and 0.60 L of water were added to the resulting solid to dissolve it, and the organic layer was removed and washed twice with water. The organic layer was washed with saturated brine, dried by adding magnesium sulfate, and then removed by gravity filtration. The filtrate obtained by gravity filtration was concentrated under reduced pressure, and the resulting solid was washed with hexane and a small amount of acetone and dried in vacuo. 15 g of a gray solid was obtained in a 72% yield. The synthesis scheme for Step 1 is shown below.

[0537] [ka]

[0538] In addition, the gray solid 1 The H NMR charts are shown in Figures 21(A) and (B), and the numerical data are shown below. Note that Figure 21(B) is an enlarged chart showing the range from 6.80 ppm to 8.50 ppm in Figure 21(A).

[0539] 1H NMR (dichloromethane-d, 500 MHz): δ = 8.66 (d, J = 8.5 Hz, 1H), 8.13-8.09 (m, 3H), 8.05 (s, 1H), 7.98 (dd, J = 8.0 Hz, J = 1.5 Hz, 2H), 7.76 (td, J = 7.5 Hz, J = 1.0 Hz, 1H), 7.63-7.59 (m, 3H), 7.51 (t, J = 7.5 Hz, 1H), 7.47 (t, J = 8.0 Hz, 1H), 7.13 (br, 1H), 1.56 (s, 9H)

[0540] This revealed that tert-butyl (6-phenyl-benzo[b]naphtho[1,2-d]furanyl)-8-carbamate was obtained.

[0541] Step 2: Synthesis of N-(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine A 1-L three-neck flask was charged with 15 g (36 mmol) of tert-butyl (6-phenyl-benzo[b]naphtho[1,2-d]furanyl)-8-carbamate and 0.36 L of dichloromethane and cooled to 0 °C. 5.5 mL (73 mmol) of trifluoroacetic acid was added dropwise to the system, followed by stirring at room temperature for 22 hours. An additional 11 mL (0.14 mol) of trifluoroacetic acid was added and stirred for 24 hours. Water and a dichloromethane solution were added to the system, and a brown solid was collected by suction filtration. The collected solid was dissolved in ethyl acetate. Water was added to the resulting mixture, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed twice with water and neutralized with aqueous sodium bicarbonate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and the magnesium sulfate was removed by gravity filtration. The filtrate obtained by gravity filtration was concentrated under reduced pressure and dried in vacuo. 9.0 g of the target light brown solid was obtained in an 80% yield. The synthesis scheme for Step 2 is shown below.

[0542] [ka]

[0543] In addition, the light brown solid 1The H NMR charts are shown in Figures 22(A) and (B), and the numerical data are shown below. Note that Figure 22(B) is an enlarged chart showing the range from 6.80 ppm to 8.90 ppm in Figure 22(A).

[0544] 1 H NMR (dichloromethane-d2,500MHz): δ=8.64(d, J=8.5Hz, 1H), 8.09(d, J=9.0Hz, 1H), 8.05(s, 1H), 8.02(d, J=7.0Hz, 2H), 7.84(d, J=7.0Hz, 1H), 7 .73(td, J1=7.5Hz, J2=1.0Hz, 1H), 7.61-7.57(m, 3H), 7.49(t, J=7.5Hz, 1H), 7.31(t, J=7.5Hz, 1H), 6.89(d, J=9.0Hz, 1H), 4.19(br, 2H)

[0545] This revealed that N-(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine was obtained.

[0546] Step 3: Synthesis of N-biphenyl-4-yl(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine A 300 mL three-neck flask equipped with a reflux condenser was charged with 6.0 g (19 mmol) of N-(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine and 4.5 g (19 mmol) of 4-bromobiphenyl. The mixture was degassed under reduced pressure and then purged with nitrogen. 0.40 mL (0.40 mmol) of tri(tert-butyl)phosphine, 3.7 g (39 mmol) of sodium tert-butoxide, and 100 mL of xylene were added. The mixture was heated to 60 °C, and 0.11 g (0.19 mmol) of bis(dibenzylideneacetone)palladium(II) was added. The resulting mixture was heated to reflux at 110 °C for 5 hours with stirring. After stirring, the mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. The resulting solid was washed with water, ethanol, and toluene, and then recrystallized from 0.20 L of toluene and 0.80 L of hexane, yielding 3.4 g of a light brown solid. The filtrate obtained by recrystallization was concentrated under reduced pressure, and the resulting solid was purified by silica gel chromatography (the developing solvent was toluene:hexane = 1:3, but was changed to toluene:hexane = 1:2 midway through). 2.0 g of a light brown solid was obtained. Thus, a total of 5.4 g of the target product was obtained in a yield of 60%. The synthesis scheme for Step 3 is shown below.

[0547] [ka]

[0548] In addition, the light brown solid 1 The H NMR charts are shown in Figures 33(A) and (B), and the numerical data are shown below. Note that Figure 33(B) is an enlarged chart showing the range from 6.3 ppm to 8.8 ppm in Figure 33(A).

[0549] 1H NMR (dichloromethane-d2,500MHz): δ=8.68(d, J=8.0Hz, 1H), 8.11(d, J=8.0Hz, 1H), 8.07(s, 1H), 8.05(dd, J1=3.5Hz, J2=1.5Hz, 1H), 7.97-7.95( m, 2H), 7.76(td, J1=8.0Hz, J2=1.5Hz, 1H), 7.64-7.59(m, 5H), 7.51(t, J=7.5Hz, 2H), 7.47-7.42(m, 5H), 7.34-7.29(m, 3H), 6.38(br, 1H)

[0550] This revealed that N-biphenyl-4-yl(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine was obtained.

[0551] <Step 4: Synthesis of N-(biphenyl-4-yl)-N-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)spiro[9H-fluorene-9,9'-[9H]xanthene]-2'-amine (abbreviation: SFxBiBnf)> A 100 mL three-neck flask equipped with a reflux condenser was charged with 2.0 g (4.3 mmol) of N-(1,1'-biphenyl)-4-yl(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine, 1.9 g (4.8 mmol) of 2'-bromospiro[fluorene-9,9'-xanthene] (BLDpharm), and 35 mg (86 μmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviated as Sphos). The mixture was degassed under reduced pressure and then purged with nitrogen. 0.83 g (8.6 mmol) of sodium tert-butoxide and 25 mL of anhydrous xylene were added, followed by further degassing. This mixture was heated to 60°C, and 25 mg (43 μmol) of bis(dibenzylideneacetone)palladium(II) was added. The resulting mixture was heated to reflux at 120°C with stirring for 1.5 hours. After stirring, the mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. Water was added to the system, and the aqueous layer was extracted with toluene. The resulting organic layer was washed twice with water and then with saturated brine, dried over magnesium sulfate, and then filtered to remove the magnesium sulfate. The filtrate obtained by gravity filtration was concentrated under reduced pressure and dried in vacuo, yielding 4.3 g of a brown solid. This brown solid was purified by silica gel chromatography (the developing solvent was set to toluene:hexane = 1:2, but was later changed to toluene:hexane = 1:1). The resulting solid was purified by recrystallization (toluene, hexane) and dried to yield 2.8 g of the target pale yellow solid in 82% yield. The synthesis scheme for Step 4 is shown below.

[0552] [ka]

[0553] The resulting solid was purified by train sublimation. The solid was heated between 316°C and 303°C for 22 hours under a pressure of 3.1 Pa while flowing argon at 10 mL / min, and the precipitated solid was collected at 230°C. 2.4 g of a pale yellow solid was obtained, with a recovery rate of 86%.

[0554] The obtained solid 1 The H NMR charts are shown in Figures 23(A) and (B), and the numerical data are shown below. Note that Figure 23(B) is an enlarged chart showing the range from 5.90 ppm to 8.80 ppm in Figure 23(A). This indicates that SFxBiBnf was obtained in this synthesis example.

[0555] 1 H NMR (dichloromethane-d2,500MHz): δ=8.63(d, J=8.0Hz, 1H), 8.09(t, J=8.5Hz, 2H), 8.04(s, 1H), 7.77(t, J=7 .0Hz, 1H), 7.61(d, J=8.0Hz, 1H), 7.57-7.54(m, 4H), 7.43-7.40(m, 6H), 7.32-7.21(m, 7H), 7.17(td, J 1=7.5Hz, J2=2.0Hz, 1H), 7.13-7.07(m, 3H), 7.02-6.99(m, 3H), 6.95(d, J=7.5Hz, 2H), 6.74(t, J=7.5 Hz, 2H), 6.70(td, J1=7.5Hz, J2=1.0Hz, 1H), 6.24(dd, J1=8.0Hz, J2=2.0Hz, 1H), 6.00(d, J=3.0Hz, 1H)

[0556] <Measurement of physical properties> Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and PL spectrum (photoluminescence spectrum) of the toluene solution and thin film of SFxBiBnf were measured.

[0557] The absorption spectra of the solutions were measured using a UV-visible spectrophotometer (FP-8600 manufactured by JASCO Corporation), and the absorption spectra of the thin films were measured using a UV-visible spectrophotometer (U-4100 manufactured by Hitachi High-Tech Corporation). The PL spectra were measured using a spectrofluorometer (FP-8600DS manufactured by JASCO Corporation).

[0558] The absorption spectrum of the toluene solution was calculated by subtracting the absorption spectrum obtained by measuring toluene alone in a quartz cell from the absorption spectrum obtained by measuring a toluene solution of SFxBiBnf in a quartz cell.

[0559] The absorption and PL spectra of the thin film were measured by depositing SFxBiBnf on a quartz substrate by vacuum deposition and sealing it with another quartz substrate as the counter substrate. The PL spectrum was measured on the sealed sample, while the absorption spectrum was measured on the sample after removing the seal and the counter substrate. The absorption spectrum was obtained by subtracting the absorption spectrum of the quartz substrate from the absorption spectrum of SFxBiBnf deposited on the quartz substrate.

[0560] The measurement results for the toluene solution are shown in Figure 24(A), and the measurement results for the thin film are shown in Figure 24(B). The SFxBiBnf toluene solution exhibited an absorption peak around 394 nm, and the SFxBiBnf thin film exhibited an absorption peak around 393 nm. No absorption bands were observed at wavelengths longer than 430 nm in either the toluene solution or the thin film. This indicates that SFxBiBnf can be used favorably as a light-emitting device, since it is unlikely to experience a decrease in luminous efficiency due to absorption at wavelengths used in displays. Furthermore, the SFxBiBnf toluene solution exhibited an emission wavelength peak around 432 nm (excitation wavelength: 325 nm), and the SFxBiBnf thin film exhibited an emission wavelength peak around 444 nm (excitation wavelength: 330 nm).

[0561] The HOMO and LUMO levels of SFxBiBnf were calculated based on cyclic voltammetry (CV) measurements. The calculation method is shown below.

[0562] The measurement device used was an electrochemical analyzer (manufactured by BAS Inc., model number: ALS Model 600A or 600C). The solution used for CV measurements was prepared by dissolving the supporting electrolyte tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) in dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) to a concentration of 100 mmol / L, and further dissolving the target substance to be measured to a concentration of 2 mmol / L.

[0563] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.), the auxiliary electrode was a platinum electrode (Pt counter electrode (5 cm) for VC-3, manufactured by BAS Co., Ltd.), and the reference electrode was an Ag / Ag + An electrode (RE7 nonaqueous solvent reference electrode manufactured by BAS Inc.) was used. Measurements were performed at room temperature (20 to 25°C). The scan rate during CV measurements was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] relative to the reference electrode were measured. Ea was the midpoint potential of the oxidation-reduction wave, and Ec was the midpoint potential of the reduction-oxidation wave. Here, the potential energy of the reference electrode used in this example relative to the vacuum level is known to be -4.94 [eV], so the HOMO level and LUMO level can be calculated from the equations HOMO level [eV] = -4.94 - Ea and LUMO level [eV] = -4.94 - Ec, respectively.

[0564] In addition, the CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was compared with the oxidation-reduction wave in the first cycle to examine the electrical stability of the compound.

[0565] As a result, the HOMO level of SFxBiBnf was found to be -5.51 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of SFxBiBnf was found to be -2.48 eV in the measurement of the reduction potential Ec [V]. Furthermore, when the waveforms after the first and 100th cycles of the oxidation-reduction wave were compared, the peak intensity was maintained at 93% in the Ea measurement and 88% in the Ec measurement, confirming that SFxBiBnf has good resistance to repeated oxidation and reduction.

[0566] Differential scanning calorimetry (DSC) of SFxBiBnf was also performed using a PerkinElmer DSC8500. The differential scanning calorimetry consisted of heating the sample from -10°C to 310°C at a heating rate of 40°C / min, holding the sample at that temperature for 3 minutes, then cooling the sample to -10°C at a heating rate of 40°C / min, and holding the sample at that temperature for 3 minutes. This cycle was repeated twice. The DSC results for the second cycle showed that SFxBiBnf had a glass transition temperature of 150°C, and neither a crystallization temperature nor a melting point was observed. This indicates that SFxBiBnf is a highly heat-resistant material and can maintain stable film quality against heat.

[0567] Thermogravimetry-differential thermal analysis (TG-DTA) of SFxBiBnf was also performed. A high-vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS) was used for the measurements. The measurements were performed at atmospheric pressure, with a heating rate of 10°C / min and a nitrogen gas flow (flow rate of 200 mL / min). The temperature at which the weight determined by thermogravimetry was -5% of the weight at the start of the measurement (decomposition temperature) was found to be 445°C, indicating that the substance has high heat resistance. In this example, the weight of SFxBiBnf used in thermogravimetry-differential thermal analysis was 4.02 mg. [Example]

[0568] Synthesis Example 2 In this synthesis example, a synthesis method for N-(biphenyl-4-yl)-N-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)spiro[9H-fluorene-9,9'-[9H]xanthene]-2-amine (abbreviation: SFx(2)BiBnf) shown as structural formula (100) in Embodiment 1 will be described. The structural formula of SFx(2)BiBnf is shown below.

[0569] [ka]

[0570] <Step 1: Synthesis of tert-butyl (6-phenyl-benzo[b]naphtho[1,2-d]furanyl)-8-carbamate> tert-Butyl (6-phenyl-benzo[b]naphtho[1,2-d]furanyl)-8-carbamate was synthesized in a similar manner to Step 1 of Example 1.

[0571] Step 2: Synthesis of N-(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine N-(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine was synthesized similarly to Step 2 of Example 1.

[0572] Step 3: Synthesis of N-biphenyl-4-yl(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine N-Biphenyl-4-yl(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine was synthesized similarly to Step 3 of Example 1.

[0573] <Step 4: Synthesis of N-(biphenyl-4-yl)-N-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)spiro[9H-fluorene-9,9'-[9H]xanthene]-2-amine (abbreviation: SFx(2)BiBnf)> A 100 mL three-neck flask equipped with a reflux condenser was charged with 2.0 g (4.3 mmol) of N-(1,1'-biphenyl)-4-yl(6-phenyl-benzo[b]naphtho[1,2-d]furan)-8-amine, 1.9 g (4.8 mmol) of 2-bromospiro[9H-fluorene-9,9'-[9H]xanthene] (Tokyo Chemical Industry Co., Ltd.), and 35 mg (86 μmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviated as Sphos). The mixture was degassed under reduced pressure and then purged with nitrogen. 0.83 g (8.6 mmol) of sodium tert-butoxide and 25 mL of anhydrous xylene were added to the flask, which was then further degassed. This mixture was heated to 60°C, and 25 mg (43 μmol) of bis(dibenzylideneacetone)palladium(II) was added. The resulting mixture was heated to reflux at 120°C with stirring for 1.5 hours. After stirring, the mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. Water was added to the system, and the aqueous layer was extracted with toluene. The resulting organic layer was washed twice with water and then with saturated brine, dried over magnesium sulfate, and then filtered to remove the magnesium sulfate. The filtrate obtained by gravity filtration was concentrated under reduced pressure and dried in vacuo, yielding 4.2 g of a brown solid. This brown solid was purified by silica gel chromatography (the developing solvent was initially toluene:hexane = 1:2, but was later changed to toluene:hexane = 2:3). The resulting solid was reprecipitated with toluene and hexane and dried, yielding 2.3 g of the target pale yellow solid in 67% yield. The synthesis scheme for Step 4 is shown below.

[0574] [ka]

[0575] The obtained solid was purified by train sublimation. The solid was heated between 313°C and 294°C for 45 hours under a pressure of 3.2 Pa while flowing argon at 10 mL / min, and the precipitated solid was collected at 235°C. 1.7 g of a pale yellow solid was obtained with a recovery rate of 74%.

[0576] The obtained solid 1 The H NMR charts are shown in Figures 25(A) and (B), and the numerical data are shown below. Note that Figure 25(B) is an enlarged chart showing the range from 6.20 ppm to 8.90 ppm in Figure 25(A). This indicates that SFx(2)BiBnf was obtained in this synthesis example.

[0577] 1 H NMR (dichloromethane-d2,500MHz): δ=8.63(d, J=8.0Hz, 1H), 8.17(dd, J1=8.0Hz, J2=1.0Hz, 1H), 8.08(d, J=9.0Hz, 1H) , 8.02(s, 1H), 7.82(d, J=8.0Hz, 1H), 7.89(d, J=7.5Hz, 1H), 7.75(td, J1=7.5Hz, J2=1.0Hz, 1H), 7.61-7.57(m, 3 H), 7.49(d, J=9.0Hz, 2H), 7.43-7.29(m, 8H), 7.24-7.11(m, 7H), 7.05(d, J=8.0Hz, 1H), 6.90(dd, J1=8.0Hz, J2= 1.5Hz, 2H), 6.93-6.90(m, 2H), 6.88(d, J=2.5Hz, 1H), 6.54(t, J=8.0Hz, 2H), 6.41(dd, J1=7.5Hz, J2=1.5Hz, 2H)

[0578] <Measurement of physical properties> Next, the absorption and PL spectra of SFx(2)BiBnf in toluene solution and thin film were measured.

[0579] The absorption spectra of the solutions were measured using an ultraviolet-visible spectrophotometer (FP-8600 manufactured by JASCO Corporation), and the absorption spectra of the thin films were measured using an ultraviolet-visible spectrophotometer (U-4100 manufactured by Hitachi High-Tech Corporation). The PL spectra were measured using a spectrofluorometer (FP-8600DS manufactured by JASCO Corporation).

[0580] The absorption spectrum of the toluene solution was calculated by subtracting the absorption spectrum obtained by measuring toluene alone in a quartz cell from the absorption spectrum obtained by measuring a toluene solution of SFx(2)BiBnf in a quartz cell.

[0581] The absorption and PL spectra of the thin film were measured by depositing SFx(2)BiBnf on a quartz substrate by vacuum evaporation and sealing it with a quartz substrate as the counter substrate. The PL spectrum was measured on the sealed sample, while the absorption spectrum was measured on the sample after removing the seal and the counter substrate. The absorption spectrum was obtained by subtracting the absorption spectrum of the quartz substrate from the absorption spectrum of SFx(2)BiBnf deposited on the quartz substrate.

[0582] The measurement results for the solution are shown in Figure 26(A), and the measurement results for the thin film are shown in Figure 26(B). From the measurement results, the SFx(2)BiBnf toluene solution exhibited an absorption peak around 347 nm, and the SFx(2)BiBnf thin film exhibited an absorption peak around 388 nm, with no absorption band observed at wavelengths longer than 440 nm. This indicates that even when SFx(2)BiBnf is used as a light-emitting device, it does not suffer from a decrease in luminous efficiency due to absorption at the wavelengths used in displays, and can be used suitably. Furthermore, the SFx(2)BiBnf toluene solution exhibited an emission wavelength peak around 425 nm (excitation wavelength: 347 nm), and the SFx(2)BiBnf thin film exhibited an emission wavelength peak around 440 nm (excitation wavelength: 330 nm).

[0583] The HOMO and LUMO levels of SFx(2)BiBnf were calculated based on cyclic voltammetry (CV) measurements. The calculation method is the same as in Example 1, so it is omitted here.

[0584] The CV measurements revealed that the HOMO level of SFx(2)BiBnf was -5.52 eV in the oxidation potential Ea [V]. The LUMO level of SFx(2)BiBnf was -2.50 eV in the reduction potential Ec [V]. Furthermore, the comparison of the waveforms after 100 cycles in the repeated oxidation-reduction wave showed that the peak intensity remained at 93% in the Ea measurement and 96% in the Ec measurement, confirming that SFx(2)BiBnf has excellent resistance to repeated oxidation and reduction.

[0585] Differential scanning calorimetry (DSC) of SFx(2)BiBnf was also performed using the same measuring device as in Example 1. The differential scanning calorimetry was performed by heating the sample from -10°C to 330°C at a heating rate of 40°C / min, holding the sample at that temperature for 3 minutes, then cooling the sample to -10°C at a heating rate of 40°C / min, and holding the sample at that temperature for 3 minutes. This procedure was repeated twice in succession. The results of the second DSC cycle showed that SFx(2)BiBnf had a glass transition temperature of 155°C, and neither a crystallization temperature nor a melting point was observed. This indicates that SFx(2)BiBnf is a substance with extremely high heat resistance and can maintain a stable film quality against heat.

[0586] Thermogravimetry-differential thermal analysis (TG-DTA) of SFx(2)BiBnf was also performed using the same apparatus as in Example 1. The measurements were performed at atmospheric pressure, with a heating rate of 10°C / min, and under a nitrogen gas flow (flow rate of 200 mL / min). The thermogravimetry-differential thermal analysis revealed that the temperature at which the weight determined by thermogravimetry was -5% of the weight at the start of the measurement (decomposition temperature) was 457°C, indicating that the substance has high heat resistance. In this example, the weight of SFx(2)BiBnf used in thermogravimetry-differential thermal analysis was 3.67 mg. [Example]

[0587] Example 1 In this example, light-emitting devices 1 and 2, which are light-emitting devices according to one embodiment of the present invention, will be described in detail. The structural formulae of representative organic compounds used in this example are shown below.

[0588] [ka]

[0589] (Method for fabricating a light-emitting device) First, a 110 nm thick film of indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The electrode area was 2 mm×2 mm.

[0590] Next, as a pretreatment for forming a light emitting element on the substrate, the surface of the substrate was washed with water and baked at 200° C. for 1 hour.

[0591] Then 1×10 -4 The substrate was introduced into a vacuum deposition apparatus whose internal pressure had been reduced to about Pa, and after vacuum baking at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus, the substrate was allowed to cool for about 30 minutes.

[0592] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum evaporation apparatus so that the surface on which the first electrode 101 was formed faced downward. N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) represented by the above structural formula (i) and an electron acceptor material (OCHD-003) containing fluorine and having a molecular weight of 672 were co-deposited on the first electrode 101 to a thickness of 10 nm by a vapor deposition method using resistance heating, so that the weight ratio was 1:0.03 (= PCBBiF:OCHD-003). Thus, a hole injection layer 111 was formed.

[0593] Next, PCBBiF was evaporated onto the hole injection layer 111 to a thickness of 90 nm to form a first hole transport layer, and then N-(biphenyl-4-yl)-N-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)spiro[9H-fluorene-9,9'-[9H]xanthene]-2'-amine (abbreviation: SFxBiBnf) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form a second hole transport layer, forming the hole transport layer 112. The second hole transport layer also functions as an electron blocking layer.

[0594] Subsequently, on the hole transport layer 112, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the above structural formula (iii) and N,N'-diphenyl-N,N'-bis(9-phenyl-9H-carbazol-2-yl)naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10PCA2Nbf(IV)-02) represented by the above structural formula (iv) were co-deposited in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) to a film thickness of 25 nm, thereby forming the light-emitting layer 113.

[0595] Then, on the light-emitting layer 113, 2-{3-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq) represented by the above structural formula (v) was formed into a film with a thickness of 10 nm to form a first electron-transporting layer, and subsequently, 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P) represented by the above structural formula (vi) was formed into a film with a thickness of 15 nm to form a second electron-transporting layer, thereby forming the electron-transporting layer 114.

[0596] On the electron transport layer 114, a film of lithium fluoride was formed to a thickness of 1 nm to form the electron injection layer 115.

[0597] Finally, aluminum was evaporated to a thickness of 200 nm to form a second electrode 102, thereby completing the light-emitting device according to one embodiment of the present invention.

[0598] Light-emitting device 2 was fabricated by forming a 10-nm-thick layer of N-(biphenyl-4-yl)-N-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)spiro[9H-fluorene-9,9'-[9H]xanthene]-2-amine (abbreviation: SFx(2)BiBnf) represented by the above structural formula (vii) in place of SFxBiBnf in the hole-transporting layer 112 of light-emitting device 1. The layers other than the hole-transporting layer were the same as those of light-emitting device 1.

[0599] The device structure of the above light-emitting device is summarized in the table below.

[0600] [Table 1]

[0601] The above light-emitting devices were sealed with glass substrates in a nitrogen-atmosphere glove box to prevent exposure to the atmosphere (sealing material was applied around the elements, and UV treatment and heat treatment at 80°C for 1 hour were performed during sealing), and then the initial characteristics of these light-emitting elements were measured.

[0602] The luminance-current density characteristics of light-emitting device 1 and light-emitting device 2 are shown in Figure 27, the current efficiency-luminance characteristics in Figure 28, the luminance-voltage characteristics in Figure 29, the current density-voltage characteristics in Figure 30, the external quantum efficiency-luminance characteristics in Figure 31, and the electroluminescence spectrum in Figure 32. 2 Table 2 shows the main characteristics around this range. The luminance, CIE chromaticity, and emission spectrum were measured using a spectroradiometer (SR-UL1R, manufactured by Topcon Corporation) at room temperature. The external quantum efficiency was calculated using the measured luminance and emission spectrum, assuming that the light distribution characteristics are Lambertian.

[0603] [Table 2]

[0604] 27 to 32 and Table 2 show that the light-emitting device of one embodiment of the present invention has low driving voltage, low power consumption, and favorable light-emitting characteristics. [Explanation of symbols]

[0605] 100A display device 100B display device 100C display device 100D display device 100D2 Display device 100E display device 100E2 Display device 1000 Insulators 1000S Insulator 101S First electrode 101 first electrode 101W First electrode 101G First electrode 101B first electrode 101R First electrode 102 second electrode 102S Second electrode 103Bf Organic compound film 103Gf organic compound film 103Rf Organic compound film 103 Organic compound layer 103B Organic compound layer 103G organic compound layer 103R Organic compound layer 103S organic compound layer 104 Common layer 110B subpixel 110G subpixel 110R subpixel 110W subpixel 110 subpixels 111 Hole injection layer 111S hole injection layer 112 Hole transport layer 112S hole transport layer 112B Conductive layer 112R conductive layer 113 Light-emitting layer 114 Electron transport layer 114S electron transport layer 115 Electron injection layer 115S electron injection layer 116 Charge generation layer 117 P type layer 118 Electronic Relay Layer 119 Electron injection buffer layer 120 boards 122 Resin layer 123 Photoelectric conversion layer 124 light 125f inorganic insulating film 125 Inorganic insulating layer 126R conductive layer 126B Conductive layer 127a Insulating layer 127f insulating film 127 Insulating Layer 128 layers 129R conductive layer 129B Conductive layer 130B Light-emitting devices 130G Light Emitting Device 130R Light Emitting Device 130 Light-emitting devices 131 Protective layer 132B Colored layer 132G colored layer 132R colored layer 140 Connection 141 areas 142 Adhesive layer 151B Conductive layer 151C conductive layer 151f Conductive film 151G conductive layer 151R conductive layer 151 Conductive layer 152B Conductive layer 152C conductive layer 152f Conductive film 152G Conductive layer 152R Conductive layer 152 Conductive layer 153 Insulating Layer 156B Insulating layer 156C Insulation layer 156f insulating film 156G Insulation layer 156R Insulation layer 156 Insulating Layer 157 Light blocking layer 158B Sacrificial Layer 158Bf sacrificial film 158G Sacrificial Layer 158Gf sacrificial film 158R Sacrificial Layer 158Rf sacrificial film 159B Mask layer 159Bf Mask membrane 159G Mask layer 159Gf Mask Film 159R Mask layer 159Rf Mask Film 166 Conductive Layer 171 Insulating layer 172 Conductive layer 173 Insulating Layer 174 Insulating Layer 175 Insulating Layer 176 Plug 177 Pixel section 178 pixels 178a pixels 178b pixels 179 Conductive Layer 190B resist mask 190G resist mask 190R resist mask 191 Resist mask 201 Transistor 204 Connection 205 Transistor 211 Insulating layer 213 Insulating Layer 214 Insulating layer 215 Insulating Layer 221 Conductive layer 222a conductive layer 222b Conductive layer 223 Conductive Layer 224B Conductive layer 224C conductive layer 224G conductive layer 224R conductive layer 231 Semiconductor layer 240 capacity 241 Conductive Layer 242 Connection Layer 243 Insulating Layer 245 Conductive Layer 254 Insulating Layer 255 insulating layer 256 plug 261 Insulating Layer 271 Plug 280 Display Module 281 Display section 282 Circuit section 283a Pixel circuit 283 Pixel circuit section 284a pixels 284 pixel section 285 Terminal section 286 Wiring section 290 FPC 291 Circuit Board 292 PCB 301 Substrate 310 Transistor 311 Conductive layer 312 Low resistance region 313 Insulating Layer 314 Insulating Layer 315 Element isolation layer 317 Light blocking layer 351 Circuit Board 352 Circuit Board 353 FPC 354 IC 355 Wiring 356 circuits 501 first electrode 502 Second electrode 513 Charge generation layer 700A electronic equipment 700B Electronic equipment 721 Case 723 Mounting part 727 Earphones 750 earphones 751 Display Panel 753 Optical Components 756 Display area 757 frames 758 Nose pad 800A electronic equipment 800B Electronic equipment 820 Display section 821 Case 822 Communications Department 823 Mounting part 824 Control Unit 825 Imaging unit 827 Earphones 832 Lens 6500 Electronic equipment 6501 Housing 6502 Display section 6503 Power button 6504 Button 6505 Speaker 6506 Microphone 6507 Camera 6508 Light source 6510 Protective materials 6511 Display Panel 6512 Optical components 6513 Touch Sensor Panel 6515 FPC 6516 IC 6517 Printed Circuit Board 6518 Battery 7000 Display 7100 Television equipment 7151 Remote Controlled Machine 7171 Case 7173 Stand 7200 Notebook Personal Computer 7211 Case 7212 keyboard 7213 Pointing Device 7214 External connection port 7300 Digital Signage 7301 Housing 7303 Speaker 7311 Information terminals 7400 Digital Signage 7401 Pillar 7411 Information terminals 9000 chassis 9001 Display section 9002 Camera 9003 Speaker 9005 Operation key 9006 Connection terminal 9007 Sensor 9008 Microphone 9050 Icon 9051 Information 9052 Information 9053 Information 9054 Information 9055 Hinge 9171 Mobile Information Terminal 9172 Mobile Information Terminal 9173 Tablet Devices 9200 Mobile Information Terminal 9201 Mobile Information Terminal

Claims

1. An organic compound represented by general formula (G1): 【Chemical 1】 (In the general formula (G1), X represents an oxygen atom or a sulfur atom, and R １ ~R １６ is a group represented by general formula (g1), and the rest each independently represent any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. 【Chemistry 2】 (In the group represented by general formula (g1), Ar １ is represented by the following general formula (Ar １ -1), and Ar ２ represents a substituted or unsubstituted phenyl group or a phenyl group having at least a substituted or unsubstituted naphthyl group. １ ~R １６ Binds to one of the following: 【Chemistry 3】 (General formula (Ar １ In the group represented by formula (1), Y represents an oxygen atom or a sulfur atom, and R １７ ~R ３２ each independently represents any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. １７ , R ２４ ~R ２６ is a bond bonding to the nitrogen atom in general formula (g1).

2. 2. The method of claim 1, wherein the Ar ２ is represented by the following structural formula (Ar ２ -1) to the following structural formula (Ar ２ -20) an organic compound represented by any one of the following groups: 【Chemistry 4】 【Chemistry 5】 (However, the above structural formula (Ar ２ -1) to structural formula (Ar ２ In formula (g1), the asterisk indicates the bond to nitrogen in formula (g1).

3. In claim 1 or claim 2, The group represented by the general formula (g1) is R ６ ~R ８ and R １３ ~R １６ An organic compound that bonds to one of the following:

4. In claim 3, General formula (Ar １ -1) R in the group represented by １７ is a bond bonded to the nitrogen atom of general formula (g1).

5. In claim 1 or claim 2, The group represented by the general formula (g1) is R ７ or R １５ An organic compound that binds to

6. In claim 5, General formula (Ar １ -1) in the group represented by １７ is a bond bonded to the nitrogen atom of general formula (g1).

7. An organic compound represented by general formula (G1): 【Chemistry 6】 (In the general formula (G1), X represents an oxygen atom or a sulfur atom, and R １ ~R １６ is a group represented by general formula (g2), and the rest each independently represent hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. 【Chemistry 7】 (In the group represented by general formula (g2), Ar ２ represents a substituted or unsubstituted phenyl group or a phenyl group having at least a substituted or unsubstituted naphthyl group, Y represents an oxygen atom or a sulfur atom, R １８ ~R ２６ each independently represents any one of hydrogen (including deuterium), a chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted cyclic saturated hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. １ ~R １６ Binds to one of the following:

8. 8. The method of claim 7, wherein the Ar ２ is represented by the following structural formula (Ar ２ -1) to the following structural formula (Ar ２ -20) an organic compound represented by any one of the following groups: 【Chemistry 8】 【Chemistry 9】 (However, the above structural formula (Ar ２ -1) to structural formula (Ar ２ In formula (g2), the asterisk indicates the bond to nitrogen in formula (g2).

9. In claim 7 or claim 8, The group represented by the general formula (g2) is R ６ ~R ８ and R １３ ~R １６ An organic compound that bonds to one of the following:

10. In claim 7 or claim 8, The group represented by the general formula (g2) is R ７ or R １５ An organic compound that binds to

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