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

Abstract

To provide a new organic compound having excellent thermophysical properties.SOLUTION: The present disclosure provides an organic compound represented by the following general formula. In the formula, X1 and X2 each independently represent a secondary or tertiary alkyl group having 3 to 6 carbon atoms and having a branched carbon atom which is bonded to a phenyl group. In addition, Ar1 represents a substituted or unsubstituted condensed aromatic ring skeleton having 10 to 60 carbon atoms and composed of two or more rings or a substituted or unsubstituted condensed heteroaromatic ring skeleton having 8 to 60 carbon atoms and composed of two or more rings. Furthermore, Ar2 represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Moreover, n represents any of 1 to 3, and in the case where n is 2 or more, the two or more groups bonded to Ar1 may be identical or different.SELECTED DRAWING: None

Description

[Technical Field]

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, a display module, a lighting module, a display device, a light-emitting device, an electronic device, and a lighting device. Note that one embodiment of the present invention is not limited to the above technical field. The technical field of one embodiment of the invention disclosed in this specification etc. relates to an object, a method, or a manufacturing method. Alternatively, one embodiment of the present invention relates to a process, a machine, manufacture, or a composition of matter. Therefore, more specific examples of the technical field of one embodiment of the present invention disclosed in this specification include semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, memory devices, imaging devices, driving methods thereof, and manufacturing methods thereof. [Background technology]

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

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

[0004] Furthermore, these light-emitting devices can emit light continuously in two dimensions, making it possible to obtain surface light emission. This is a feature that is difficult to obtain with point light sources such as incandescent bulbs and LEDs, or linear light sources such as fluorescent lamps, making them highly useful as surface light sources for lighting applications.

[0005] Displays and lighting devices using such light-emitting devices are suitable for use in a variety of electronic devices, but research and development is ongoing to find light-emitting devices with better characteristics (see Patent Document 1). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 2019-085387 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of one embodiment of the present invention is to provide a novel organic compound. Alternatively, an object of one embodiment of the present invention is to provide an organic compound having good thermal properties. Alternatively, an object of one embodiment of the present invention is to provide an organic compound having high solubility. Alternatively, an object of one embodiment of the present invention is to provide an organic compound having good color purity and a low deposition temperature.

[0008] Another object of one embodiment of the present invention is to provide a novel blue light-emitting material, a blue light-emitting material with good thermal properties, or a blue light-emitting material with good color purity and a low deposition temperature.

[0009] Another object of one embodiment of the present invention is to provide an organic compound that can be deposited at a low temperature and that can provide a light-emitting device with good characteristics, or to provide an organic compound that can be deposited at a low temperature and that can provide a light-emitting device with good lifetime.

[0010] Another object of one embodiment of the present invention is to provide a blue light-emitting material that can be deposited at a low deposition temperature and that can provide a light-emitting device with good characteristics.Another object of one embodiment of the present invention is to provide a blue light-emitting material that can be deposited at a low deposition temperature and that can provide a light-emitting device with good lifetime.Another object of one embodiment of the present invention is to provide a blue light-emitting material that has good initial characteristics and lifetime and can be deposited at a low deposition temperature.Another object of one embodiment of the present invention is to provide a light-emitting device with good operating lifetime at high temperatures.

[0011] Another object of one embodiment of the present invention is to provide a light-emitting device, a light-emitting apparatus, an electronic device, and a display device that have a long lifetime and are easy to manufacture.

[0012] Note that the description of these problems does not preclude the existence of other problems. Note that one embodiment of the present invention does not necessarily need to solve all of these problems. Note that problems other than these will become apparent from the description in the specification, drawings, claims, etc., and it is possible to extract other problems from the description in the specification, drawings, claims, etc.

[0013] The present invention is intended to solve any one of the above problems. [Means for solving the problem]

[0014] One embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0015] [ka]

[0016] However, in the above general formula (G1), X 1 and X 2 each independently represents a secondary or tertiary alkyl group having 3 to 6 carbon atoms, and the carbon atom bonded to the phenyl group is branched. 1 represents a substituted or unsubstituted fused aromatic ring skeleton having 10 to 60 carbon atoms and two or more rings, or a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and two or more rings, Ar 2 represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. 1 ~R 7 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. In addition, n is any one of 1 to 3, and when n is 2 or more, Ar 1 The two or more groups bonded to may be the same or different.

[0017] Another aspect of the present invention is, in the above-mentioned configuration, 1 is a substituted or unsubstituted fused aromatic ring skeleton having 10 to 60 carbon atoms and 3 to 9 rings, or a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and 3 to 9 rings.

[0018] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 1 is a substituted or unsubstituted organic compound having a fused heteroaromatic ring skeleton with 8 to 60 carbon atoms and 3 to 7 rings.

[0019] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the X 1 or X 2 are organic compounds each independently having 3 or 4 carbon atoms and a secondary or tertiary alkyl group in which the carbon atom bonded to the phenyl group is branched.

[0020] Another embodiment of the present invention is an organic compound having the above structure, wherein n is 2.

[0021] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 1 is an organic compound having a heteroaromatic ring skeleton represented by any one of the following general formulas (B1) to (B4).

[0022] [ka]

[0023] However, in the formula, Q 1 and Q 2 Each of R independently represents an oxygen atom or a sulfur atom. 10 ~R 21 In the above general formula (B2), one or two of R represents a single bond, and the remaining R each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. 30 ~R 41 In the above general formula (B3), one or two of R represents a single bond, and the remaining R each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. 50 ~R 61 In the above general formula (B4), one or two of R represents a single bond, and the remaining R each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. 70 ~R 81One or two of the groups represented by the formula (I) represent a single bond, and the remaining groups each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms.

[0024] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 1 is an organic compound having a heteroaromatic ring skeleton represented by the following general formula (B1-1) or (B3-1).

[0025] [ka]

[0026] However, in the formula, Q 1 and Q 2 Each independently represents an oxygen atom or a sulfur atom. 12 , R 18 , R 52 and R 58 represents a single bond.

[0027] Another embodiment of the present invention is an organic compound represented by the following general formula (G1-1).

[0028] [ka]

[0029] However, in the above general formula (G1-1), X 3 ~X 6 are each independently a secondary or tertiary alkyl group having 3 to 6 carbon atoms, and the carbon atom bonded to the phenyl group is branched. 21 and Ar 22 each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0030] Another embodiment of the present invention is a light-emitting device including any of the above organic compounds.

[0031] Another embodiment of the present invention is an electronic device including any of the above light-emitting devices and a sensor, an operation button, a speaker, or a microphone.

[0032] Another embodiment of the present invention is a light-emitting device including the above light-emitting device and a transistor or a substrate.

[0033] Another embodiment of the present invention is a lighting device including the above-described light-emitting device and a housing.

[0034] In this specification, the term "light-emitting device" includes an image display device using a light-emitting device. The term "light-emitting device" may also include a module in which a connector, such as an anisotropic conductive film or TCP (Tape Carrier Package), is attached to a light-emitting device, a module in which a printed wiring board is provided at the end of the TCP, or a module in which an IC (integrated circuit) is directly mounted on a light-emitting device using a COG (Chip On Glass) method. Furthermore, lighting fixtures and the like may include a light-emitting device. [Effects of the Invention]

[0035] According to one embodiment of the present invention, a novel organic compound can be provided. Alternatively, according to one embodiment of the present invention, an organic compound having good thermal properties can be provided. Alternatively, according to one embodiment of the present invention, an organic compound having good color purity and a low deposition temperature can be provided.

[0036] Alternatively, one embodiment of the present invention can provide a novel blue light-emitting material, a blue light-emitting material with good thermal properties, or a blue light-emitting material with good color purity and a low deposition temperature.

[0037] Alternatively, one embodiment of the present invention can provide an organic compound that can be deposited at a low temperature and that can provide a light-emitting device with good characteristics. Alternatively, one embodiment of the present invention can provide an organic compound that can be deposited at a low temperature and that can provide a light-emitting device with good lifetime. Alternatively, one embodiment of the present invention can provide an organic compound that can be deposited at a low temperature and that has good initial characteristics and lifetime.

[0038] Alternatively, one embodiment of the present invention can provide a light-emitting device with good characteristics and a blue light-emitting material that can be deposited at a low temperature. Alternatively, one embodiment of the present invention can provide a light-emitting device with good lifetime and a blue light-emitting material that can be deposited at a low temperature. Alternatively, one embodiment of the present invention can provide a blue light-emitting material that has good initial characteristics and lifetime and can be deposited at a low temperature.

[0039] According to another embodiment of the present invention, a light-emitting device, a light-emitting apparatus, an electronic device, and a display device that have a long lifetime and are easy to manufacture can be provided. Alternatively, according to another embodiment of the present invention, a light-emitting device that has a long operating lifetime at high temperatures can be provided.

[0040] Note that the description of these effects does not preclude the existence of other effects. Note that one embodiment of the present invention does not necessarily have all of these effects. Note that effects other than these will become apparent from the description in the specification, drawings, claims, etc., and it is possible to extract other effects from the description in the specification, drawings, claims, etc. [Brief explanation of the drawings]

[0041] [Figure 1] 1(A), 1(B) and 1(C) are schematic diagrams of light-emitting devices. [Figure 2] 2(A) and 2(B) are conceptual diagrams of an active matrix light emitting device. [Figure 3] 3(A) and 3(B) are conceptual diagrams of an active matrix light emitting device. [Figure 4]FIG. 4 is a conceptual diagram of an active matrix light emitting device. [Figure 5] 5(A) and 5(B) are conceptual diagrams of a passive matrix light emitting device. [Figure 6] 6(A) and 6(B) are diagrams showing the lighting device. [Figure 7] 7(A), 7(B1), 7(B2) and 7(C) are diagrams showing electronic devices. [Figure 8] 8(A), 8(B) and 8(C) are diagrams showing electronic devices. [Figure 9] FIG. 9 is a diagram showing a lighting device. [Figure 10] FIG. 10 is a diagram showing a lighting device. [Figure 11] FIG. 11 is a diagram showing an in-vehicle display device and a lighting device. [Figure 12] 12(A) and 12(B) are diagrams showing electronic devices. [Figure 13] 13(A), 13(B) and 13(C) are diagrams showing electronic devices. [Figure 14] Figure 14(A) and Figure 14(B) are 1H NMR charts of N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-amine. [Figure 15] Figures 15(A) and 15(B) are 1H NMR charts of 3,10mmtBuPCA2Nbf(IV)-02. [Figure 16] Figure 16 shows the absorption and emission spectra of 3,10mmtBuPCA2Nbf(IV)-02 in a toluene solution. [Figure 17] Figure 17 shows the absorption and emission spectra of 3,10mmtBuPCA2Nbf(IV)-02 in a thin film state. [Figure 18] FIG. 18 shows the luminance-current density characteristics of the light-emitting device 1, the comparative light-emitting device 1-1, and the comparative light-emitting device 1-2. [Figure 19]FIG. 19 shows the current efficiency-luminance characteristics of the light-emitting device 1, the comparative light-emitting device 1-1, and the comparative light-emitting device 1-2. [Figure 20] FIG. 20 shows the luminance-voltage characteristics of the light-emitting device 1, the comparative light-emitting device 1-1, and the comparative light-emitting device 1-2. [Figure 21] FIG. 21 shows the current-voltage characteristics of the light-emitting device 1, the comparative light-emitting device 1-1, and the comparative light-emitting device 1-2. [Figure 22] FIG. 22 shows the external quantum efficiency-luminance characteristics of the light-emitting device 1, the comparative light-emitting device 1-1, and the comparative light-emitting device 1-2. [Figure 23] FIG. 23 shows the emission spectra of the light-emitting device 1, the comparative light-emitting device 1-1, and the comparative light-emitting device 1-2. [Figure 24] Figure 24 shows the emission spectra of 3,10mmtBuPCA2Nbf(IV)-02, 3,10mmEtPCA2Nbf(IV)-02, 3,10mmHexPCA2Nbf(IV)-02, and 3,10PCA2Nbf(IV)-02 in the solution state. [Figure 25] Figure 25 shows the relationship between weight and temperature in thermogravimetry-differential thermal analysis of 3,10mmtBuPCA2Nbf(IV)-02, 3,10mmEtPCA2Nbf(IV)-02, 3,10mmHexPCA2Nbf(IV)-02, and 3,10PCA2Nbf(IV)-02. [Figure 26] FIG. 26 is a graph showing the change in luminance with respect to the driving time of the light-emitting device 1, the comparative light-emitting device 1-1, and the comparative light-emitting device 1-2. [Figure 27] FIG. 27 shows the luminance-current density characteristics of the light-emitting device 2 and the comparative light-emitting device 2. [Figure 28] FIG. 28 shows the current efficiency-luminance characteristics of the light-emitting device 2 and the comparative light-emitting device 2. [Figure 29] FIG. 29 shows the luminance-voltage characteristics of the light-emitting device 2 and the comparative light-emitting device 2. [Figure 30] FIG. 30 shows the current-voltage characteristics of the light-emitting device 2 and the comparative light-emitting device 2. [Figure 31]FIG. 31 shows the external quantum efficiency-luminance characteristics of the light-emitting device 2 and the comparative light-emitting device 2. [Figure 32] FIG. 32 shows the emission spectra of the light-emitting device 2 and the comparative light-emitting device 2. [Figure 33] FIG. 33 is a graph showing the change in luminance of the light-emitting device 2 and the comparative light-emitting device 2 with respect to the driving time. [Figure 34] FIG. 34 shows the luminance-current density characteristics of the light-emitting device 3. [Figure 35] FIG. 35 shows the current efficiency-luminance characteristics of the light-emitting device 3. [Figure 36] FIG. 36 shows the luminance-voltage characteristics of the light-emitting device 3. [Figure 37] FIG. 37 shows the current-voltage characteristics of the light-emitting device 3. [Figure 38] FIG. 38 shows the external quantum efficiency vs. luminance characteristics of the light-emitting device 3. [Figure 39] FIG. 39 shows the emission spectrum of the light-emitting device 3. [Figure 40] FIG. 40 is a graph showing the change in luminance of the light-emitting device 3 with respect to the driving time. [Figure 41] Figure 41 shows the absorption and emission spectra of 3,10 mm EtPCA2Nbf(IV)-02 in toluene solution. [Figure 42] Figure 42 shows the absorption and emission spectra of 3,10 mm EtPCA2Nbf(IV)-02 in a thin film state. [Figure 43] Figure 43(A) and Figure 43(B) are 1H NMR charts of mmtBuPCA-03. [Figure 44] Figure 44(A) and Figure 44(B) are 1H NMR charts of 1,6mmtBuPCAPrn-03. [Figure 45] Figure 45 shows the absorption spectrum and emission spectrum of 1,6mmtBuPCAPrn-03 in toluene solution. [Figure 46] Figure 46 shows the absorption and emission spectra of 1,6mmtBuPCAPrn-03 in a thin film state. [Figure 47] Figure 47(A) and Figure 47(B) are 1H NMR charts of 5,9mmtBuPCA2PcgDBC-03. [Figure 48] Figure 48 shows the absorption and emission spectra of 5,9mmtBuPCA2PcgDBC-03 in a toluene solution. [Figure 49] Figure 49 shows the absorption and emission spectra of 5,9mmtBuPCA2PcgDBC-03 in a thin film state. [Figure 50] Figure 50(A) and Figure 50(B) are 1H NMR charts of mmtBuPCFA. [Figure 51] Figure 51(A) and Figure 51(B) are 1H NMR charts of FrFAmmtBuPC. [Figure 52] FIG. 52 shows the absorption spectrum and emission spectrum of FrFAmmtBuPC in a toluene solution. [Figure 53] Figure 53 shows the absorption and emission spectra of FrFAmmtBuPC in a thin film state. [Figure 54] Figure 54(A) and Figure 54(B) are 1H NMR charts of mmtBuPCzPCFL. [Figure 55] FIG. 55 shows the absorption spectrum and emission spectrum of mmtBuPCzPCFL in a toluene solution. [Figure 56] FIG. 56 shows the absorption and emission spectra of mmtBuPCzPCFL in a thin film state. [Figure 57] FIG. 57 shows the luminance-current density characteristics of the light-emitting device 4. [Figure 58] FIG. 58 shows the current efficiency-luminance characteristics of the light-emitting device 4. [Figure 59] FIG. 59 shows the luminance-voltage characteristics of the light-emitting device 4. [Figure 60] FIG. 60 shows the current-voltage characteristics of the light-emitting device 4. [Figure 61] FIG. 61 shows the external quantum efficiency vs. luminance characteristics of the light-emitting device 4. [Figure 62]FIG. 62 shows the emission spectrum of the light-emitting device 4. [Figure 63] FIG. 63 shows the luminance-current density characteristics of the light-emitting device 5. [Figure 64] FIG. 64 shows the current efficiency-luminance characteristics of the light-emitting device 5. [Figure 65] FIG. 65 shows the luminance-voltage characteristics of the light-emitting device 5. [Figure 66] FIG. 66 shows the current-voltage characteristics of the light-emitting device 5. [Figure 67] FIG. 67 shows the external quantum efficiency-luminance characteristics of the light-emitting device 5. [Figure 68] FIG. 68 shows the emission spectrum of the light-emitting device 5. [Figure 69] FIG. 69 shows the luminance-current density characteristics of the light-emitting device 6 and the light-emitting device 7. [Figure 70] FIG. 70 shows the current efficiency-luminance characteristics of the light-emitting device 6 and the light-emitting device 7. [Figure 71] FIG. 71 shows the luminance-voltage characteristics of the light-emitting device 6 and the light-emitting device 7. [Figure 72] FIG. 72 shows the current-voltage characteristics of the light-emitting device 6 and the light-emitting device 7. [Figure 73] FIG. 73 shows the external quantum efficiency-luminance characteristics of the light-emitting device 6 and the light-emitting device 7. [Figure 74] FIG. 74 shows the emission spectra of light-emitting device 6 and light-emitting device 7. DETAILED DESCRIPTION OF THE INVENTION

[0042] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it will be readily understood by those skilled in the art that various changes in form and details can be made 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.

[0043] (Embodiment 1) In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0044] An organic compound according to one embodiment of the present invention is represented by the following general formula (G1).

[0045] [ka]

[0046] The organic compound represented by the general formula (G1) is X 1 and X 2 That is, the two meta positions of the phenyl group bonded to the 9-position of the carbazolyl group are independently substituted with alkyl groups having 3 to 6 carbon atoms, thereby improving sublimability and solubility in solvents. This makes film formation and purification easier, leading to improved productivity and reliability. In addition, X 1 and X 2 are each independently an alkyl group having 3 or 4 carbon atoms, which can be synthesized inexpensively and has good sublimation properties, and is therefore preferred.

[0047] In addition, the bonding position of the alkyl group is X 1 and X 2 Therefore, one of the characteristics of the organic compound represented by General Formula (G1) is that the HOMO level and the LUMO level are hardly affected by the bonding of the alkyl group. Therefore, the organic compound represented by General Formula (G1), which is an organic compound according to one embodiment of the present invention, can be obtained by 1 and X 2 By having the alkyl group, the sublimability and solubility can be improved without substantially affecting the HOMO level, LUMO level, emission spectrum, or band gap.

[0048] In addition, a secondary or tertiary alkyl group in which the carbon bonded to the phenyl group at the 9th position of the carbazolyl group is branched, i.e., an alkyl group in which the carbon bonded directly to the phenyl group is branched, is preferred because it improves the reliability of light-emitting devices using the organic compound.

[0049] From these facts, X of the organic compound represented by the general formula (G1) 1 and X 2 It is more preferable that the carbazolyl group is a secondary or tertiary alkyl group having 3 to 6 carbon atoms and having a branched carbon bonded to the phenyl group, because this can be synthesized inexpensively and has good sublimability. In other words, by having a branched carbon bonded to the phenyl group at the 9th position of the carbazolyl group, it is possible to suppress intermolecular interactions. Furthermore, this can be achieved by placing the carbazolyl group at a position where the molecule is not distorted too much (two meta positions, i.e., X 1 and X 2 By substituting both the carbazolyl group and the alkyl group at both positions, intermolecular interactions can be further suppressed compared to placing the carbazolyl group at only one of the two meta positions. Furthermore, since conjugation is unlikely to extend from the carbazolyl group to the phenyl group at the 9th position of the carbazolyl group, even if an alkyl group is introduced into the phenyl group, the emission spectrum and absorption spectrum are unlikely to change. Furthermore, introducing an alkyl group into the phenyl group is preferable because it improves the heat resistance of the organic compound.

[0050] In addition, X of the organic compound represented by the general formula (G1) 1 and X 2 is more preferably a secondary or tertiary alkyl group having 3 or 4 carbon atoms and in which the carbon atom bonded to the phenyl group is branched.

[0051] As the secondary or tertiary alkyl group having 3 to 6 carbon atoms and having a branched carbon atom bonded to the phenyl group, specifically, groups represented by the following structural formulas (X-1) to (X-9) can be used.

[0052] [ka]

[0053] Also, R 1 ~R 7 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms.

[0054] Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Specific examples of the cycloalkyl group having 3 to 12 carbon atoms include a cyclopropyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group. Specific examples of the unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms include a phenyl group, a biphenyl group, a naphthyl group, and a dimethylfluorenyl group.

[0055] In addition, n is any one of 1 to 3, and when n is 2 or more, Ar 1 The two or more groups bonded to Ar may be the same or different. 1 may have a plurality of the same substituents bonded thereto, or may have a plurality of substituents each having a different constitution bonded thereto.

[0056] Also, Ar 1 represents a substituted or unsubstituted fused aromatic ring skeleton having 10 to 60 carbon atoms and two or more rings, or a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and two or more rings.

[0057] The above Ar 1 Specific examples of the substituted or unsubstituted fused aromatic ring skeleton having 10 to 60 carbon atoms and two or more rings or the substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and two or more rings, which are exemplified as the group represented by the following structural formula (Ar1 -1)~(Ar 1 -56) and the like.

[0058] [ka]

[0059] [ka]

[0060] In addition, Ar 1 is preferably a substituted or unsubstituted fused aromatic ring skeleton having 10 to 60 carbon atoms and 3 to 9 rings, or a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and 3 to 9 rings, because of its high sublimability, and is more preferably a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and 3 to 7 rings, because of its high heat resistance.

[0061] Among them, the Ar 1 is any one of the heteroaromatic ring skeletons represented by the following general formulas (B1) to (B4), is more preferred because it exhibits good blue light emission.

[0062] [ka]

[0063] In the above general formulas (B1) to (B4), Q 1 and Q 2 Each of R independently represents an oxygen atom or a sulfur atom. 10 ~R 21 In the above general formula (B2), one or two of R represents a single bond, and the remaining R each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. 30 ~R41 In the above general formula (B3), one or two of R represents a single bond, and the remaining R each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. 50 ~R 61 In the above general formula (B4), one or two of R represents a single bond, and the remaining R each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. 70 ~R 81 One or two of the groups represented by the formula (I) represent a single bond, and the remaining groups each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms.

[0064] Specific examples of alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, and hexyl groups. Examples of cycloalkyl groups having 3 to 10 carbon atoms include cyclopropyl, cyclohexyl, norbornyl, decahydronaphthyl, and adamantyl groups. Examples of aryl groups having 6 to 13 carbon atoms include phenyl, biphenyl, naphthyl, and fluorenyl groups.

[0065] Among the general formulae (B1) to (B4), the heteroaromatic ring skeleton represented by the general formula (B1) or (B3) is more preferred because it exhibits blue light emission, and the heteroaromatic ring skeleton represented by the following general formula (B1-1) or (B3-1) is even more preferred because it has a high luminescence quantum yield. 1 and Q 2 Each independently represents an oxygen atom or a sulfur atom. 12 , R 18 , R 52 and R58 represents a single bond.

[0066] [ka]

[0067] Also, Ar 2 represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Examples of the substituted or unsubstituted aryl group having 6 to 25 carbon atoms include a phenyl group, a tolyl group, a dimethylphenyl group, a trimethylphenyl group, a propylphenyl group, a dipropylphenyl group, a butylphenyl group, a dibutylphenyl group, a cyclohexylphenyl group, a naphthyl group, a naphthylphenyl group, a phenylnaphthyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a phenanthryl group, a 9,9-diphenylfluorenyl group, a spirofluorenyl group, a triphenylenyl group, a pyrenyl group, an anthryl group, and a 9-phenylanthryl group. Specific examples of the substituted or unsubstituted aryl group having 6 to 25 carbon atoms include a phenyl group, a phenyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a phenanthryl group, a 9,9-diphenylfluorenyl group, a spirofluorenyl group, a triphenylenyl group, a pyrenyl group, an anthryl group, and a 9-phenylanthryl group. 2 -1)~(Ar 2 -49) and the like.

[0068] [ka]

[0069] [ka]

[0070] In addition, in the organic compound represented by the general formula (G1), Ar 1 is preferably a heteroaromatic ring skeleton represented by the above general formula (B3-1), since this results in an organic compound that exhibits high color purity and good blue light emission. 1 ~R 7 is preferably hydrogen because synthesis is easy. That is, the organic compound of one embodiment of the present invention is preferably an organic compound represented by the following general formula (G1-1).

[0071] [ka]

[0072] However, in the above general formula (G1-1), X 3 ~X 6 each independently represents a secondary or tertiary alkyl group having 3 to 6 carbon atoms, and the carbon atom bonded to the phenyl group is branched; and X in the above general formula (G1) 1 and X 2 The same groups as those in Ar can be selected. 21 and Ar 22 each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and Ar 2 The same groups as those shown in the above can be selected.

[0073] The organic compound represented by the general formula (G1-1) above is an organic compound that exhibits good blue light emission. 3 ~X 6 By having the above, the sublimation property is improved.

[0074] From the organic compound represented by the general formula (G1-1), X 3 ~X 6 The organic compounds other than X have a large molecular weight and have multiple amine skeletons or furan rings in the molecule, so the temperature for sublimation purification is close to 400°C. If the heating temperature is about 400°C, the organic compound may burn before sublimation. On the other hand, the organic compound of one embodiment of the present invention is 3 ~X 6 By having the above structure, the interaction between molecules can be reduced, and the sublimation temperature can be lowered. This can prevent scorching during sublimation purification. In addition, the evaporation temperature can be lowered, improving productivity.

[0075] In addition, X is an organic compound represented by the general formula (G1-1). 3 ~X 6The organic compounds except for X were difficult to produce because they were poorly soluble in solvents. 3 ~X 6 The organic compound of one embodiment of the present invention having the formula (I) also has increased solubility in a solvent, and therefore can be easily purified using a solvent.

[0076] In the above description, when a group or ring described as "substituted or unsubstituted" has a substituent, the substituent can be an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. More preferred are alkyl groups having 1 to 6 carbon atoms and cycloalkyl groups having 3 to 12 carbon atoms, and even more preferred are alkyl groups having 1 to 6 carbon atoms. From the viewpoint of ease of synthesis and ease of availability of raw materials, it is preferable that a group or ring described as "substituted or unsubstituted" be unsubstituted.

[0077] Furthermore, preferred examples of the alkyl group having 1 to 6 carbon atoms mentioned above include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Preferred examples of the cycloalkyl group having 3 to 12 carbon atoms include a cyclopropyl group, a cyclohexyl group, a norbornyl group, a decahydronaphthyl group, and an adamantyl group. Preferred examples of the aryl group having 6 to 13 carbon atoms include a phenyl group, a biphenyl group, a naphthyl group, and a fluorenyl group.

[0078] Specific examples of organic compounds having the above structure are shown below.

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[0099] Next, an example of a method for synthesizing the organic compound of the present invention as described above will be explained. The organic compound represented by general formula (G1) is shown below.

[0100] [ka]

[0101] However, in the above general formula (G1), X 1 and X 2each independently represents a secondary or tertiary alkyl group having 3 to 6 carbon atoms, and the carbon atom bonded to the phenyl group is branched. 1 represents a substituted or unsubstituted fused aromatic ring skeleton having 10 to 60 carbon atoms and two or more rings, or a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and two or more rings, Ar 2 represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. 1 ~R 7 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. n is any one of 1 to 3, and when n is 2 or more, Ar 1 The two or more groups bonded to may be the same or different.

[0102] The organic compound represented by general formula (G1) can be obtained by cross-coupling reaction of compound (a1) with arylamine compound (a2), as shown in the synthesis scheme below. 1 Examples of B include halogens such as chlorine, bromine, and iodine, and triflate groups. 2 Examples of the group include hydrogen and organotin groups.

[0103] [ka]

[0104] This reaction can proceed under various conditions, including metal-catalyzed synthesis in the presence of a base, such as the Ullmann coupling or the Hartwig-Buchwald reaction.

[0105] Here, n equivalents of compound (a2) are reacted with compound (a1). However, if n is 2 or more, that is, if compound (G1) has two or more substituents in parentheses bonded thereto and the substituents are not the same, compound (a2) may be reacted with compound (a1) one by one.

[0106] When n is 1, the organic compound represented by general formula (g1) can be obtained by cross-coupling reaction between compound (a3) and arylamine compound (a4), or between compound (a5) and arylamine compound (a6), as shown in the synthesis scheme below. 1 Examples of B include halogens such as chlorine, bromine, and iodine, and triflate groups. 2 Examples of the group include hydrogen and organotin groups.

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[0109] In the above manner, the organic compound of one embodiment of the present invention can be synthesized.

[0110] (Embodiment 2) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described.

[0111] 1A illustrates a light-emitting device according to one embodiment of the present invention. The light-emitting device according to one embodiment of the present invention includes a first electrode 101, a second electrode 102, and an EL layer 103. The EL layer 103 includes the organic compound described in Embodiment 1.

[0112] The EL layer 103 has a light-emitting layer 113, which contains a light-emitting material. A hole-injection layer 111 and a hole-transport layer 112 are provided between the light-emitting layer 113 and the first electrode 101. The organic compound described in Embodiment 1 is preferably used as the light-emitting material because it efficiently emits blue fluorescence.

[0113] The light-emitting layer 113 may also contain a host material together with the light-emitting material. The host material is an organic compound having carrier-transporting properties. The host material may contain one or more types of host materials. In this case, it is preferable that the multiple organic compounds include an organic compound having electron-transporting properties and an organic compound having hole-transporting properties, because this allows for the carrier balance in the light-emitting layer 113 to be adjusted. The multiple organic compounds may all have electron-transporting properties, but by varying the electron-transporting properties, it is possible to adjust the electron-transporting properties in the light-emitting layer 113. By appropriately adjusting the carrier balance, a light-emitting device with a long lifetime can be provided. An exciplex may also be formed between the multiple organic compounds serving as host materials or between the host material and the light-emitting material. By forming an exciplex having an appropriate emission wavelength, effective energy transfer to the light-emitting material can be achieved, thereby providing a light-emitting device with high efficiency and a long lifetime.

[0114] 1(A) illustrates the EL layer 103 including the light-emitting layer 113, the hole injection layer 111, the hole transport layer 112, the electron transport layer 114, and the electron injection layer 115. However, the configuration of the light-emitting device is not limited to these. Any of these layers may not be formed, or a layer having another function may be included.

[0115] Next, examples of the detailed structure and materials of the above-described light-emitting device will be described. As described above, the light-emitting device of one embodiment of the present invention includes the EL layer 103 composed of multiple layers between a pair of electrodes, the first electrode 101 and the second electrode 102, and any part of the EL layer 103 contains the organic compound disclosed in Embodiment 1.

[0116] The first electrode 101 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 tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium 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 formed by applying a sol-gel method. For example, indium zinc oxide may be formed by sputtering using a target containing indium oxide and 1 to 20 wt% zinc oxide. Indium oxide containing tungsten oxide and zinc oxide (IWZO) may also be formed by sputtering using a target containing indium oxide and 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), and nitrides of metal materials (e.g., titanium nitride). Graphene can also be used. By using a composite material (described later) in the layer of the EL layer 103 that is in contact with the first electrode 101, it becomes possible to select an electrode material regardless of the work function.

[0117] The EL layer 103 preferably has a stacked layer structure, but the stacked layer structure is not particularly limited, and various layer structures such as a hole-injection layer, a hole-transport layer, a light-emitting layer, an electron-transport layer, an electron-injection layer, a carrier-blocking layer, an exciton-blocking layer, and a charge-generation layer can be applied. In this embodiment, two types of structures will be described: a structure including an electron-transport layer 114 and an electron-injection layer 115 in addition to a hole-injection layer 111, a hole-transport layer 112, and a light-emitting layer 113 as shown in FIG. 1A; and a structure including an electron-transport layer 114 and a charge-generation layer 116 in addition to a hole-injection layer 111, a hole-transport layer 112, and a light-emitting layer 113 as shown in FIG. 1B. Materials constituting each layer are specifically described below.

[0118] The hole-injection layer 111 is a layer containing a substance having acceptor properties. As the substance having acceptor properties, either an organic compound or an inorganic compound can be used.

[0119] As the acceptor substance, a compound having an electron-withdrawing group (a halogen group or a cyano group) can be used, and examples thereof include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), 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 thermally stable and preferred. Radialene derivatives having electron-withdrawing groups (especially halogen groups such as fluoro groups or cyano groups) are also preferred because of their extremely high electron-accepting properties. Specific examples include α,α',α''-1,2,3-cyclopropanetriylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropanetriylidene tris[2,3,4,5,6-pentafluorobenzeneacetonitrile]. In addition to the organic compounds described above, other materials having acceptor properties can include molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. The hole injection layer 111 can also be formed from phthalocyanine complex compounds such as phthalocyanine (abbreviated as HPc) and copper phthalocyanine (CuPc), aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as DNTPD), or polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS).A substance having acceptor properties can extract electrons from an adjacent hole transport layer (or hole transport material) when an electric field is applied.

[0120] Alternatively, a composite material in which a material having a hole-transporting property contains the above-mentioned acceptor substance can be used for the hole-injection layer 111. Note that by using a composite material in which a material having a hole-transporting property contains an acceptor substance, a material for forming an electrode can be selected regardless of the work function. That is, not only a material with a high work function but also a material with a low work function can be used for the first electrode 101.

[0121] As a material having hole transport properties to be used in the composite material, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, and polymer compounds (oligomers, dendrimers, polymers, etc.) can be used. Note that as a material having hole transport properties to be used in the composite material, -6 cm 2 A substance having a hole mobility of 1 / Vs or more is preferred. Specific examples of organic compounds that can be used as a material having a hole transport property in a composite material are listed below.

[0122] Examples of aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B). Specific examples of the carbazole derivative include 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole, and Examples of compounds that can be used include tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (abbreviation: CzPA), and 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene.Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), 2-tert- Examples of suitable anthracene include butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, and 2,5,8,11-tetra(tert-butyl)perylene. Pentacene and coronene may also be used. It may have a vinyl skeleton. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi) and 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA).

[0123] In addition, polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used.

[0124] The hole-transporting material used in the composite material preferably has 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. Note that these second organic compounds are preferably substances having an N,N-bis(4-biphenyl)amino group, since this allows the fabrication of light-emitting devices with long lifetimes. Specific examples of the second organic compound include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8 -yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d] Furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: : BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-Diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4''-(5;2'- (binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine nylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tris(1,1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyl Triphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spiro-bi[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-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)trimethylamine 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 (abbreviated as PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviated as PCBASF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviated as PCBASF), )phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluorene]-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluorene]-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluorene]-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,Examples include 9'-spirobi[9H-fluorene]-1-amine.

[0125] Note that the material having hole-transporting properties used in the composite material is more preferably a substance having a relatively deep HOMO level of −5.7 eV or more and −5.4 eV or less. When the material having hole-transporting properties used in the composite material has a relatively deep HOMO level, injection of holes into the hole-transport layer 112 becomes easy, and a light-emitting device with a long lifetime can be easily obtained.

[0126] The refractive index of the layer can be reduced by further mixing an alkali metal or alkaline earth metal fluoride into the composite material (preferably with an atomic ratio of fluorine atoms of 20% or more in the layer), which also allows a layer with a low refractive index to be formed inside the EL layer 103, thereby improving the external quantum efficiency of the light-emitting device.

[0127] By forming the hole injection layer 111, the hole injection property is improved, and a light-emitting device with a low driving voltage can be obtained. In addition, organic compounds having acceptor properties are easy to use because they can be easily vapor-deposited and formed into films.

[0128] The hole transport layer 112 is formed by including a material having a hole transport property. -6 cm 2The hole transporting material preferably has a hole mobility of 1 / Vs or more. Examples of the hole transporting material include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPA), and the like. FLP), 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 PCB Aromatic amines such as 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 a benzophenone 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), and compounds with a benzophenone skeleton such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,Examples of suitable compounds include compounds having a thiophene skeleton, such as 8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), and compounds having a furan skeleton, such as 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among the above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferred because they have good reliability, high hole transport properties, and contribute to reducing driving voltage. Note that the substances listed as materials having hole transport 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. The organic compounds described in Embodiment 1 have high hole transport properties and are therefore very suitable for use as materials for the hole transport layer 112. Furthermore, because the organic compounds described in Embodiment 1 have high hole transport properties, even if the hole transport layer 112 is formed to a thickness of 100 nm or more, a light-emitting device can be provided that exhibits only a small increase in driving voltage and has good device characteristics. By thickening the hole transport layer 112, the optical path length between electrodes can be easily adjusted, which makes it easy to appropriately configure a microcavity structure.

[0129] The organic compound described in Embodiment 1 has a low refractive index and a bulky alkyl group bonded thereto, so that a film having a low refractive index can be obtained. Therefore, when used in a light-emitting element, the light extraction efficiency is increased, and an element having high luminous efficiency can be obtained.

[0130] The light-emitting layer 113 contains a light-emitting substance and a host material. The light-emitting layer 113 may also contain other materials. The light-emitting layer 113 may also be a stack of two layers with different compositions.

[0131] The light-emitting material may be a fluorescent material, a phosphorescent material, a material that exhibits thermally activated delayed fluorescence (TADF), or any other light-emitting material.

[0132] Examples of materials that can be used as fluorescent emitting substances in the light emitting layer 113 include 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2′-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4′-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2′-bipyridine (abbreviation: PAPP2BPy), N,N′-diphenyl-N,N′-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N′-bis(3-methylphenyl) N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4- phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N',N'',N'',N''',N'''-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetrahydrofuran N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl- N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,N,N'-(5H-benzo[ij]quinolizin-9-yl)ethenyl)-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02), and the like. In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds like 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred because they have high hole-trapping properties, excellent luminous efficiency, and reliability. Other fluorescent materials can also be used.

[0133] The organic compound described in Embodiment 1 can also be used as a fluorescent substance. A light-emitting device according to one embodiment of the present invention preferably uses the organic compound described in Embodiment 1. The organic compound described in Embodiment 1 is an organic compound that can be easily purified and vapor-deposited; therefore, a highly reliable light-emitting device can be provided. Furthermore, since the thermal properties can be improved while maintaining high color purity, a light-emitting device with good color purity and high reliability can be provided. Furthermore, a light-emitting device with good operating life at high temperatures can be provided.

[0134] When a phosphorescent material is used as the light-emitting material in the light-emitting layer 113, examples of materials that can be used include tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1, Organometallic iridium complexes with a 4H-triazole skeleton, such as tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz)3]) and tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]), and tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1 Organometallic iridium complexes with a 1H-triazole skeleton, such as [Ir(Mptz1-mp)3]tris(1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) and tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), and fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl]- Organometallic iridium complexes with an imidazole skeleton, such as [Nyl-1H-imidazole]iridium(III) (abbreviated as [Ir(iPrpmi)3]) and tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviated as [Ir(dmpimpt-Me)3]), and bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’] Organometallic iridium complexes with phenylpyridine derivatives containing electron-withdrawing groups as ligands, such as iridium(III) acetylacetonate (abbreviated as FIr(acac)), are compounds that exhibit blue phosphorescence, with an emission spectrum peak between 440 nm and 520 nm.

[0135] 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 (acetylacetonato)bis(4,6-diphenylpyrimidinato)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-pyridyl-κN2)phenyl-κ]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mbfpypy-d3)]), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridyl-κN2)phenyl-κ]iridium(III) Examples include organometallic iridium complexes with a pyridine backbone, such as [zofro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviated as [Ir(ppy)2(mbfpypy-d3)]), 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 an emission spectrum peak between 500 and 600 nm. Organometallic iridium complexes with a pyrimidine backbone are particularly preferred due to their outstanding reliability and luminous efficiency.

[0136] In addition, organometallic iridium complexes having a pyrimidine skeleton, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), and bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), Organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), and tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ Examples include organometallic iridium complexes with a pyridine skeleton, such as iridium(III) acetylacetonate (abbreviated as [Ir(piq)2(acac)]), platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(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)]). These compounds exhibit red phosphorescence, with an emission peak between 600 and 700 nm. Furthermore, organometallic iridium complexes having a pyrazine skeleton can emit red light with good chromaticity.

[0137] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting substances may be selected and used.

[0138] 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.

[0139] [ka]

[0140] 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 either 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 or heteroaromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, etc. In this way, a π-electron-deficient skeleton or 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.

[0141] [ka]

[0142] 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.

[0143] 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.

[0144] The phosphorescence spectrum observed at low temperatures (for example, 77 K to 10 K) can be used as an indicator of the T1 level. 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 defined 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 defined 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.

[0145] 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.

[0146] As the host material of the light-emitting layer, various carrier transporting materials such as a material having an electron transporting property, a material having a hole transporting property, or the above-mentioned TADF material can be used.

[0147] As a material having hole transport properties, an organic compound having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton is preferable. For example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP ... mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (PCBANB), 4, Aromatic amine skeletons such as 4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF) and 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), as well as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,Examples of suitable compounds include compounds having a thiophene skeleton, such as 8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), and compounds having a furan skeleton, such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among the above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferred because they have good reliability, high hole transport properties, and contribute to reducing driving voltage.

[0148] Examples of materials having electron transport properties include metal complexes such as bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), as well as organic compounds having a π-electron-deficient heteroaromatic ring skeleton.Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1, Heterocyclic compounds with polyazole skeletons such as 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoline, 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoline, and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoline. quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl) Examples of heterocyclic compounds include heterocyclic compounds having a diazine skeleton, such as 4,6mDBTP2Pm-II (bis[3-(dibenzothiophen-4-yl)phenyl]-benzo[h]quinazoline (abbreviation: 4,8mDBtP2Bqn), and heterocyclic compounds having a pyridine skeleton, such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) and 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB). Among the above, heterocyclic compounds having a diazine skeleton and heterocyclic compounds having a pyridine skeleton are preferred due to their high reliability.In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties and contribute to reducing the driving voltage.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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 the distance between the TADF material and the luminophore of the fluorescent material to be increased 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 the fused aromatic ring or the fused heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, and a phenothiazine skeleton. In particular, fluorescent substances having a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, or a naphthobisbenzofuran skeleton are preferred because of their high fluorescence quantum yield.

[0153] When a fluorescent emitting substance is used as the emitting substance, a material having an anthracene skeleton is suitable as the host material. Using a substance having an anthracene skeleton as the host material for a fluorescent emitting substance makes it possible to realize an emitting layer with both excellent luminous efficiency and durability. As a substance having an anthracene skeleton to be used as a host material, 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 carbazole, are even more preferred because their HOMO is approximately 0.1 eV shallower than that of carbazole, facilitating hole insertion. In particular, host materials containing a dibenzocarbazole skeleton are preferred because their HOMO is approximately 0.1 eV shallower than that of carbazole, facilitating hole insertion, and also exhibiting excellent hole transport properties and high heat resistance. Therefore, a more preferable host material is a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). From the viewpoint of the hole injection / transport property, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton. Examples of such a substance include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), and 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole. Examples include benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: FLPPA), and 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth).In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferable choices because they exhibit very good properties.

[0154] The host material may be a mixture of a plurality of substances. When a mixture of host materials is used, it is preferable to mix a material having an electron-transporting property with a material having a hole-transporting property. By mixing a material having an electron-transporting property with a material having a hole-transporting property, the transport property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The weight ratio of the content of the material having a hole-transporting property to the material having an electron-transporting property may be 1:19 to 19:1. The organic compound described in Embodiment 1 can be preferably used as the material having an electron-transporting property in the mixed host material.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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).

[0159] 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.

[0160] The electron-transporting layer 114 is a layer containing a substance having an electron-transporting property. As the substance having an electron-transporting property, any of the substances exemplified above as the substance having an electron-transporting property that can be used as the host material can be used.

[0161] The electron transport layer 114 has an electron mobility of 1×10 when the square root of the electric field strength [V / cm] is 600. -7 cm 2 / Vs or more 5×10 -5 cm 2 / Vs or less. By reducing the electron transport property of the electron-transport layer 114, the amount of electrons injected into the light-emitting layer can be controlled, and the light-emitting layer can be prevented from becoming electron-excessive. The electron-transport layer 114 preferably contains a material having electron-transport properties and an element, compound, or complex of an alkali metal or alkaline earth metal. These structures are particularly preferable because they improve the lifetime when the hole-injection layer is formed as a composite material and the material having hole-transport properties in the composite material has a relatively deep HOMO level of −5.7 eV or more and −5.4 eV or less. In this case, the material having electron-transport properties preferably has a HOMO level of −6.0 eV or more. The material having electron-transport properties is preferably an organic compound having an anthracene skeleton, and more preferably an organic compound having both an anthracene skeleton and a heterocyclic skeleton. The heterocyclic skeleton is preferably a nitrogen-containing five-membered ring skeleton or a nitrogen-containing six-membered ring skeleton, and particularly preferably a nitrogen-containing five-membered ring skeleton or a nitrogen-containing six-membered ring skeleton containing two heteroatoms in the ring, such as a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazine ring, a pyrimidine ring, or a pyridazine ring. Furthermore, the alkali metal or alkaline earth metal simple substance, compound, or complex preferably contains an 8-hydroxyquinolinato structure. Specific examples include 8-hydroxyquinolinato-lithium (abbreviated as Liq) and 8-hydroxyquinolinato-sodium (abbreviated as Naq). In particular, monovalent metal ion complexes, especially lithium complexes, are preferred, with Liq being more preferred. When the 8-hydroxyquinolinato structure is contained, its methyl-substituted derivatives (e.g., 2-methyl-substituted derivatives or 5-methyl-substituted derivatives) can also be used. In addition, it is preferable that the alkali metal or alkaline earth metal simple substance, compound, or complex in the electron transport layer has a concentration difference (including zero) in the thickness direction.

[0162] Between the electron transport layer 114 and the second electrode 102, a layer containing an alkali metal or alkaline earth metal, such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), or 8-hydroxyquinolinato-lithium (abbreviated as Liq), or a compound thereof, may be provided as the electron injection layer 115. The electron injection layer 115 may be a layer made of a substance having electron transport properties containing an alkali metal or alkaline earth metal or a compound thereof, or an electride. Examples of the electride include a substance in which electrons are highly concentrated in a mixed oxide of calcium and aluminum.

[0163] Note that a layer containing a fluoride of the alkali metal or alkaline earth metal in a concentration (50 wt % or more) sufficient to form a microcrystalline state in a substance having an electron transport property (preferably an organic compound having a bipyridine skeleton) can also be used as the electron-injection layer 115. Since this layer has a low refractive index, it is possible to provide a light-emitting device with better external quantum efficiency.

[0164] 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 second electrode 102, which is 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 the production of a light-emitting device with excellent external quantum efficiency.

[0165] 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 .

[0166] 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.

[0167] 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)).

[0168] 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 constituting the electron-transport layer 114 described above.

[0169] The second electrode 102 can be formed from a metal, alloy, electrically conductive compound, or mixture thereof with a low work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs), elements belonging to Group 1 or Group 2 of the periodic table such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these metals (MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these metals. However, by providing an electron injection layer between the second electrode 102 and the electron transport layer, various conductive materials, such as Al, Ag, ITO, and indium tin oxide containing silicon or silicon oxide, can be used for the second electrode 102, regardless of the magnitude of the work function. These conductive materials can be formed into films using dry methods such as vacuum deposition and sputtering, inkjet printing, spin coating, or the like. Alternatively, the layer may be formed by a wet method using a sol-gel method, or by a wet method using a paste of a metal material.

[0170] In addition, various methods, whether dry or wet, can be used to form the EL layer 103. For example, vacuum deposition, gravure printing, offset printing, screen printing, inkjet printing, or spin coating may be used.

[0171] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0172] The configuration of the layers provided between the first electrode 101 and the second electrode 102 is not limited to the above. However, a configuration in which a light-emitting region where holes and electrons recombine is provided at a location away from the first electrode 101 and the second electrode 102 is preferable so as to suppress quenching caused by the proximity of the light-emitting region to the metals used in the electrodes and the carrier injection layer.

[0173] Furthermore, the hole transport layer and electron transport layer in contact with the light-emitting layer 113, particularly the carrier transport layer close to the recombination region in the light-emitting layer 113, are preferably made of a material having a band gap larger than the band gap of the light-emitting material constituting the light-emitting layer or the light-emitting material contained in the light-emitting layer, in order to suppress energy transfer from excitons generated in the light-emitting layer.

[0174] Next, an embodiment of a light-emitting device having a configuration 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 configuration substantially similar to that of the EL 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.

[0175] 1(C), a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between an anode 501 and a cathode 502, and a charge generation layer 513 is provided between the first light-emitting unit 511 and the second light-emitting unit 512. The anode 501 and the cathode 502 correspond to the first electrode 101 and the second electrode 102 in FIG. 1(A), respectively, and the same electrodes as those described in the description of FIG. 1(A) can be applied. The first light-emitting unit 511 and the second light-emitting unit 512 may have the same structure or different structures.

[0176] The charge generation layer 513 has a function of injecting electrons into one light-emitting unit and injecting holes into the other light-emitting unit when a voltage is applied between the anode 501 and the cathode 502. That is, in FIG. 1C, when a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the charge generation layer 513 may inject electrons into the first light-emitting unit 511 and inject holes into the second light-emitting unit 512.

[0177] 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.

[0178] 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.

[0179] 1C illustrates a light-emitting device having two light-emitting units, but the present invention can 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, a device can be realized that emits high-luminance light while maintaining a low current density and has a long life. Furthermore, a light-emitting device that can be driven at a low voltage and consumes low power can be realized.

[0180] 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.

[0181] Each layer and electrode, such as the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and the charge generation layer 513, can be formed by, for example, an evaporation method (including a vacuum evaporation method), a droplet discharge method (also called an ink-jet method), a coating method, a gravure printing method, etc. They may also contain a low-molecular-weight material, a medium-molecular-weight material (including an oligomer and a dendrimer), or a polymer material.

[0182] (Embodiment 3) In this embodiment, a light-emitting device using the light-emitting device described in Embodiment 2 will be described.

[0183] In this embodiment, a light-emitting device manufactured using the light-emitting device described in Embodiment 2 will be described with reference to FIG. 2. FIG. 2(A) is a top view showing the light-emitting device, and FIG. 2(B) is a cross-sectional view taken along lines AB and CD in FIG. 2(A). This light-emitting device includes a driver circuit section (source line driver circuit) 601, a pixel section 602, and a driver circuit section (gate line driver circuit) 603, all of which are shown by dotted lines, to control light emission from the light-emitting device. 604 is a sealing substrate, 605 is a sealant, and the inside surrounded by the sealant 605 is a space 607.

[0184] The routing wiring 608 is wiring for transmitting signals input to the source line driver circuit 601 and the gate line driver circuit 603, and receives video signals, clock signals, start signals, reset signals, etc. from an FPC (flexible printed circuit) 609, which serves as an external input terminal. Although only the FPC is shown here, a printed wiring board (PWB) may be attached to this FPC. In this specification, the light-emitting device includes not only the light-emitting device itself, but also a state in which an FPC or PWB is attached to it.

[0185] Next, the cross-sectional structure will be described with reference to Fig. 2(B) . A driver circuit portion and a pixel portion are formed on an element substrate 610, and here, a source line driver circuit 601, which is the driver circuit portion, and one pixel in the pixel portion 602 are shown.

[0186] The element substrate 610 may be made of a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, acrylic resin, or the like.

[0187] The structure of the transistors used in the pixels and driver circuits is not particularly limited. For example, they may be inverted staggered transistors or staggered transistors. Furthermore, they may be top-gate or bottom-gate transistors. The semiconductor material used for the transistors is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and gallium nitride. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In-Ga-Zn-based metal oxide, may be used.

[0188] The crystallinity of a semiconductor material used for a transistor is not particularly limited, and any of an amorphous semiconductor and a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a crystalline region in part) may be used. The use of a crystalline semiconductor is preferable because it can suppress deterioration of transistor characteristics.

[0189] Here, it is preferable to use an oxide semiconductor for semiconductor devices such as transistors provided in the pixels and driver circuits, as well as transistors used in touch sensors, which will be described later. In particular, it is preferable to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor having a wider band gap than silicon, the current in the off state of the transistor can be reduced.

[0190] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn), and more preferably contains an oxide represented by In-M-Zn oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0191] In particular, it is preferable to use, as the semiconductor layer, an oxide semiconductor film having a plurality of crystal parts whose c-axes are oriented perpendicular to the surface where the semiconductor layer is formed or the top surface of the semiconductor layer and which has no grain boundaries between adjacent crystal parts.

[0192] By using such a material for the semiconductor layer, fluctuations in electrical characteristics are suppressed, and a highly reliable transistor can be realized.

[0193] Furthermore, a transistor having the above-described semiconductor layer can retain charge stored in a capacitor through the transistor for a long period of time due to its low off-state current. By applying such a transistor to a pixel, it is possible to stop the driver circuit while maintaining the gray level of an image displayed in each display region. As a result, an electronic device with extremely low power consumption can be realized.

[0194] To stabilize the characteristics of the transistor, it is preferable to provide an underlayer film. The underlayer film can be formed as a single layer or a multilayer using an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film. The underlayer film can be formed by a sputtering method, a CVD (Chemical Vapor Deposition) method (such as a plasma CVD method, a thermal CVD method, or a MOCVD (Metal Organic CVD) method), an ALD (Atomic Layer Deposition) method, a coating method, a printing method, or the like. Note that the underlayer film need not be provided if it is not necessary.

[0195] Note that FET 623 represents one of the transistors formed in the drive circuit section 601. The drive circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In addition, although this embodiment shows a driver-integrated type in which the drive circuit is formed on a substrate, this is not necessarily required, and the drive circuit may also be formed externally rather than on the substrate.

[0196] Furthermore, the pixel portion 602 is formed by a plurality of pixels each including a switching FET 611, a current control FET 612, and a first electrode 613 electrically connected to the drain of the FET, but is not limited to this, and the pixel portion may be formed by combining three or more FETs and a capacitive element.

[0197] An insulator 614 is formed to cover an end portion of the first electrode 613. Here, the insulator 614 can be formed using a positive photosensitive acrylic resin film.

[0198] Furthermore, in order to improve the coverage of an EL layer or the like to be formed later, a curved surface having a curvature is formed at the upper or lower end of the insulator 614. For example, when a positive photosensitive acrylic resin is used as the material for the insulator 614, it is preferable that only the upper end of the insulator 614 has a curved surface having a radius of curvature (0.2 μm to 3 μm). Furthermore, either a negative photosensitive resin or a positive photosensitive resin can be used as the insulator 614.

[0199] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. The material used for the first electrode 613, which functions as an anode, is preferably a material with a large work function. For example, a single-layer film such as an ITO film, an indium tin oxide film containing silicon, an indium oxide film containing 2 to 20 wt % zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, or a Pt film can be used. It is also possible to use a laminated structure of a titanium nitride film and a film mainly composed of aluminum, or a three-layer structure of a titanium nitride film, a film mainly composed of aluminum, and a titanium nitride film. The laminated structure provides low wiring resistance, good ohmic contact, and the first electrode 613 can function as an anode.

[0200] The EL layer 616 is formed by various methods such as a vapor deposition method using a vapor deposition mask, an inkjet method, or a spin coating method. The EL layer 616 includes the components described in Embodiment 2. Other materials constituting the EL layer 616 may be low-molecular compounds or high-molecular compounds (including oligomers and dendrimers).

[0201] Furthermore, the second electrode 617, which is formed on the EL layer 616 and functions as a cathode, is preferably made of a material with a small work function (such as Al, Mg, Li, or Ca, or an alloy or compound thereof (MgAg, MgIn, AlLi, etc.)). When light generated in the EL layer 616 is to be transmitted through the second electrode 617, the second electrode 617 is preferably made of a laminate of a thin metal thin film and a transparent conductive film (such as ITO, indium oxide containing 2 to 20 wt % zinc oxide, indium tin oxide containing silicon, or zinc oxide (ZnO)).

[0202] Note that a light-emitting device is formed with the first electrode 613, the EL layer 616, and the second electrode 617. The light-emitting device is the light-emitting device described in Embodiment 2. Note that a pixel portion is formed with a plurality of light-emitting devices, but the light-emitting device in this embodiment may include both the light-emitting device described in Embodiment 2 and light-emitting devices having other structures.

[0203] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with a sealing material 605, a structure is formed in which a light-emitting device 618 is provided in a space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. The space 607 is filled with a filler, and in some cases, it is filled with an inert gas (nitrogen, argon, etc.), or with a sealing material. A recess is formed in the sealing substrate, and by providing a desiccant there, deterioration due to the influence of moisture can be suppressed, which is a preferable configuration.

[0204] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is also desirable that these materials are as moisture and oxygen impermeable as possible. In addition to glass and quartz substrates, plastic substrates made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, acrylic resin, etc. can be used for the sealing substrate 604.

[0205] Although not shown in FIG. 2, a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. The protective film may also be formed so as to cover the exposed portion of the sealing material 605. The protective film may also be provided so as to cover the surfaces and side surfaces of the pair of substrates, the exposed side surfaces of the sealing layer, the insulating layer, etc.

[0206] The protective film can be made of a material that is impermeable to impurities such as water, and therefore can effectively prevent impurities such as water from diffusing from the outside to the inside.

[0207] The protective film may be made of an oxide, a nitride, a fluoride, a sulfide, a ternary compound, a metal, a polymer, or the like. For example, a material containing aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide, titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide, cerium oxide, scandium oxide, erbium oxide, vanadium oxide, indium oxide, or the like; a material containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, gallium nitride, or the like; a nitride containing titanium and aluminum; an oxide containing titanium and aluminum; an oxide containing aluminum and zinc; a sulfide containing manganese and zinc; a sulfide containing cerium and strontium; an oxide containing erbium and aluminum; or an oxide containing yttrium and zirconium.

[0208] The protective film is preferably formed using a film formation method that provides good step coverage. One such method is atomic layer deposition (ALD). It is preferable to use a material that can be formed using the ALD method for the protective film. By using the ALD method, it is possible to form a dense protective film with reduced defects such as cracks and pinholes, or with a uniform thickness. In addition, it is possible to reduce damage to the workpiece when forming the protective film.

[0209] For example, by forming a protective film using the ALD method, it is possible to form a uniform protective film with few defects on surfaces with complex uneven shapes, as well as on the top, side, and back surfaces of a touch panel.

[0210] In this manner, a light-emitting device manufactured using the light-emitting device described in Embodiment 2 can be obtained.

[0211] The light-emitting device in this embodiment can have favorable characteristics because it uses the light-emitting device described in Embodiment 2. Specifically, the light-emitting device described in Embodiment 2 has favorable luminous efficiency, and therefore can have low power consumption.

[0212] 3 shows an example of a full-color light-emitting device in which a light-emitting device that emits white light is formed and a colored layer (color filter) is provided, etc. Fig. 3(A) shows a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, and 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driver circuit portion 1041, first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting device, a sealing substrate 1031, a sealant 1032, etc.

[0213] In FIG. 3A, the colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) are provided on a transparent base material 1033. A black matrix 1035 may also be provided. The transparent base material 1033 on which the colored layers and the black matrix are provided is aligned and fixed to the substrate 1001. The colored layers and the black matrix 1035 are covered with an overcoat layer 1036. In FIG. 3A, there are light-emitting layers from which light does not pass through the colored layers and exits to the outside, and light-emitting layers from which light passes through the colored layers of each color and exits to the outside. Light that does not pass through the colored layers is white, and light that passes through the colored layers is red, green, and blue, so that an image can be displayed using four color pixels.

[0214] 3B shows an example in which colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. In this way, the colored layers may be provided between the substrate 1001 and the sealing substrate 1031.

[0215] Furthermore, the light-emitting device described above has a structure in which light is extracted from the substrate 1001 side on which the FET is formed (bottom emission type), but it may also have a structure in which light is extracted from the sealing substrate 1031 side (top emission type). A cross-sectional view of a top emission type light-emitting device is shown in FIG. 4. In this case, a light-opaque substrate can be used as the substrate 1001. The process is the same as for a bottom emission type light-emitting device up to the formation of a connection electrode that connects the FET and the anode of the light-emitting device. Thereafter, a third interlayer insulating film 1037 is formed to cover the electrode 1022. This insulating film may also serve as a planarizing film. The third interlayer insulating film 1037 can be formed using the same material as the second interlayer insulating film, as well as other known materials.

[0216] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device are anodes in this example, but may be cathodes. In the case of a top-emission light-emitting device as shown in FIG. 4, the first electrodes are preferably reflective electrodes. The EL layer 1028 has the same structure as that of the EL layer 103 in the second embodiment, and has an element structure that allows white light emission.

[0217] In the top-emission structure shown in FIG. 4, sealing can be performed using a sealing substrate 1031 provided with colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B). The sealing substrate 1031 may be provided with a black matrix 1035 positioned between pixels. The colored layers (the red colored layer 1034R, the green colored layer 1034G, and the blue colored layer 1034B) and the black matrix 1035 may be covered with an overcoat layer 1036. Note that a light-transmitting substrate is used as the sealing substrate 1031. In addition, although an example of full-color display using four colors, red, green, blue, and white, is shown here, this is not particularly limited, and full-color display using four colors, red, yellow, green, and blue, or three colors, red, green, and blue, may also be performed.

[0218] A microcavity structure is suitable for use in top-emission light-emitting devices. A light-emitting device with a microcavity structure can be obtained by using a reflective electrode as the first electrode and a semi-transmissive / semi-reflective electrode as the second electrode. At least an EL layer is provided between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least an emissive layer that serves as the light-emitting region is provided.

[0219] The reflectance of the reflective electrode to visible light is 40% to 100%, preferably 70% to 100%, and the resistivity is 1×10 -2 The semi-transmitting and semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1×10 -2 It is assumed that the film has a resistance of Ωcm or less.

[0220] The light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transmissive and semi-reflective electrode, causing resonance.

[0221] In this light-emitting device, the optical distance between the reflective electrode and the semi-transparent / semi-reflective electrode can be changed by changing the thickness of the transparent conductive film, the composite material described above, the carrier transport material, etc. This makes it possible to intensify light with resonant wavelengths and attenuate light with non-resonant wavelengths between the reflective electrode and the semi-transparent / semi-reflective electrode.

[0222] Note that, since the light reflected by the reflective electrode and returned (first reflected light) significantly interferes with the light (first incident light) that directly enters the semi-transmissive-semi-reflective electrode from the light-emitting layer, it is preferable to adjust the optical distance between the reflective electrode and the light-emitting layer to (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the wavelength of the emitted light to be amplified). By adjusting this optical distance, the phases of the first reflected light and the first incident light can be matched, thereby further amplifying the light emitted from the light-emitting layer.

[0223] In the above configuration, the EL layer may have a structure having multiple light-emitting layers or a structure having a single light-emitting layer. For example, it may be combined with the above-mentioned tandem light-emitting device configuration, in which multiple EL layers are provided in one light-emitting device with a charge-generating layer sandwiched therebetween, and one or more light-emitting layers are formed in each EL layer.

[0224] The microcavity structure makes it possible to increase the light emission intensity of specific wavelengths in the front direction, thereby reducing power consumption. In the case of a light-emitting device that displays images using four sub-pixels of red, yellow, green, and blue, not only is the yellow light emitted effective in improving brightness, but the microcavity structure that matches the wavelength of each color can be applied to all sub-pixels, resulting in a light-emitting device with good characteristics.

[0225] The light-emitting device in this embodiment can have favorable characteristics because it uses the light-emitting device described in Embodiment 2. Specifically, the light-emitting device described in Embodiment 2 has favorable luminous efficiency, and therefore can have low power consumption.

[0226] Up to this point, active matrix light-emitting devices have been described. From here on, passive matrix light-emitting devices will be described. FIG. 5 shows a passive matrix light-emitting device manufactured by applying the present invention. FIG. 5(A) is a perspective view showing the light-emitting device, and FIG. 5(B) is a cross-sectional view taken along the XY line in FIG. 5(A). In FIG. 5, an EL layer 955 is provided between an electrode 952 and an electrode 956 on a substrate 951. An end of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided on the insulating layer 953. The sidewalls of the partition layer 954 are inclined such that the distance between one sidewall and the other sidewall becomes narrower as the sidewall approaches the substrate surface. That is, the cross section of the partition layer 954 in the short side direction is trapezoidal, and the bottom side (the side facing the same direction as the surface of the insulating layer 953 and in contact with the insulating layer 953) is shorter than the top side (the side facing the same direction as the surface of the insulating layer 953 and not in contact with the insulating layer 953). By providing the partition layer 954 in this manner, defects in the light-emitting device due to static electricity or the like can be prevented. Furthermore, the light-emitting device described in Embodiment 2 is used in a passive matrix light-emitting device, and the light-emitting device can be highly reliable or consumes less power.

[0227] The light emitting device described above is capable of individually controlling a large number of minute light emitting devices arranged in a matrix, and is therefore suitable for use as a display device for displaying images.

[0228] This embodiment mode can be freely combined with other embodiment modes.

[0229] (Fourth embodiment) In this embodiment, an example in which the light-emitting device described in Embodiment 2 is used as a lighting device will be described with reference to Fig. 6. Fig. 6B is a top view of the lighting device, and Fig. 6A is a cross-sectional view taken along line ef in Fig. 6B.

[0230] In the lighting device of this embodiment, a first electrode 401 is formed over a light-transmitting substrate 400, which serves as a support. The first electrode 401 corresponds to the first electrode 101 in Embodiment 2. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.

[0231] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0232] An EL layer 403 is formed on the first electrode 401. The EL layer 403 corresponds to the structure of the EL layer 103 in Embodiment 2, or a structure in which the light-emitting units 511 and 512 and the charge generation layer 513 are combined, or the like. For details of these structures, see the descriptions therein.

[0233] A second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in Embodiment 2. When light is extracted from the first electrode 401 side, the second electrode 404 is formed of a material with high reflectivity. The second electrode 404 is connected to a pad 412 to supply a voltage.

[0234] As described above, the lighting device described in this embodiment includes a light-emitting device having the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting device has high emission efficiency, the lighting device in this embodiment can be a lighting device with low power consumption.

[0235] The lighting device is completed by bonding and sealing the substrate 400 on which the light-emitting device having the above structure is formed and a sealing substrate 407 using sealants 405 and 406. Either one of the sealants 405 and 406 may be used. Also, a desiccant may be mixed into the inner sealant 406 (not shown in FIG. 6(B)), which can absorb moisture and improve reliability.

[0236] Furthermore, the pad 412 and a part of the first electrode 401 can be extended outside the sealing materials 405 and 406 to serve as an external input terminal. An IC chip 420 equipped with a converter or the like may also be provided thereon.

[0237] As described above, the lighting device described in this embodiment uses the light-emitting device described in Embodiment 2 as its EL element, and can be a lighting device with low power consumption.

[0238] (Embodiment 5) In this embodiment, an example of an electronic device including the light-emitting device described in Embodiment 2 as a part thereof will be described. The light-emitting device described in Embodiment 2 has good luminous efficiency and low power consumption. As a result, the electronic device described in this embodiment can be an electronic device having a light-emitting portion with low power consumption.

[0239] Examples of electronic devices to which the light-emitting devices are applied include television sets (also called televisions or television receivers), computer monitors, digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), portable game machines, personal digital assistants, sound players, large game machines such as pachinko machines, etc. Specific examples of these electronic devices are shown below.

[0240] 7A illustrates an example of a television set. The television set includes a display portion 7103 in a housing 7101. Here, the housing 7101 is supported by a stand 7105. The display portion 7103 can display images, and the light-emitting devices described in Embodiment 2 are arranged in a matrix.

[0241] The television set can be operated using operation switches provided on the housing 7101 or a separate remote control 7110. Operation keys 7109 provided on the remote control 7110 can be used to operate the channel and volume, and to control the image displayed on the display portion 7103. The remote control 7110 may be provided with a display portion 7107 that displays information output from the remote control 7110.

[0242] The television device is configured to include a receiver, a modem, etc. The receiver can receive general television broadcasts, and by connecting to a wired or wireless communication network via the modem, it is also possible to perform one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.

[0243] FIG. 7B1 shows a computer including a main body 7201, a housing 7202, a display portion 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like. Note that this computer is manufactured by using the light-emitting devices described in Embodiment 2 arranged in a matrix for the display portion 7203. The computer in FIG. 7B1 may have a configuration as shown in FIG. 7B2. The computer in FIG. 7B2 is provided with a second display portion 7210 instead of the keyboard 7204 and the pointing device 7206. The second display portion 7210 has a touch panel, and input can be performed by operating an input display displayed on the second display portion 7210 with a finger or a dedicated pen. The second display portion 7210 can display not only an input display but also other images. The display portion 7203 may also be a touch panel. The two screens are connected by a hinge, which can prevent the screens from being scratched or broken during storage or transportation.

[0244] 7C shows an example of a mobile terminal. The mobile phone includes a display portion 7402 incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. Note that the mobile phone includes the display portion 7402 in which the light-emitting devices described in Embodiment 2 are arranged in a matrix.

[0245] 7C can be configured so that information can be input by touching the display portion 7402 with a finger or the like. In this case, operations such as making a call or creating an e-mail can be performed by touching the display portion 7402 with a finger or the like.

[0246] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images, the second is an input mode that mainly inputs information such as characters, and the third is a display+input mode that combines the display mode and the input mode.

[0247] For example, when making a call or creating an e-mail, the display portion 7402 may be set to a character input mode mainly for inputting characters, and characters displayed on the screen may be input. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402.

[0248] Furthermore, by providing a detection device having a sensor for detecting tilt, such as a gyroscope or an acceleration sensor, inside the mobile terminal, the orientation of the mobile terminal (portrait or landscape) can be determined and the screen display of the display portion 7402 can be automatically switched.

[0249] The screen mode can be switched by touching the display portion 7402 or by operating the operation buttons 7403 on the housing 7401. The screen mode can also be switched depending on the type of image displayed on the display portion 7402. For example, if the image signal to be displayed on the display portion is moving image data, the display mode is selected, and if it is text data, the input mode is selected.

[0250] In addition, in the input mode, a signal detected by an optical sensor of the display portion 7402 may be detected, and if there is no input by touch operation on the display portion 7402 for a certain period of time, the screen mode may be controlled to switch from the input mode to the display mode.

[0251] The display portion 7402 can also function as an image sensor. For example, personal authentication can be performed by touching the display portion 7402 with a palm or a finger to capture an image of a palm print, fingerprint, or the like. Furthermore, by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light for the display portion, finger veins, palm veins, or the like can also be captured.

[0252] FIG. 8(A) is a schematic diagram showing an example of a cleaning robot.

[0253] The cleaning robot 5100 has a display 5101 arranged on its top surface, multiple cameras 5102 arranged on its side, a brush 5103, and an operation button 5104. Although not shown, the cleaning robot 5100 is also provided with tires, a suction port, and the like on its bottom surface. The cleaning robot 5100 also has various other sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezoelectric sensor, an optical sensor, and a gyro sensor. The cleaning robot 5100 also has wireless communication means.

[0254] The cleaning robot 5100 can move by itself, detect dust 5120, and suck up the dust from a suction port provided on the bottom surface.

[0255] Furthermore, the cleaning robot 5100 can analyze the image captured by the camera 5102 to determine whether there are any obstacles such as walls, furniture, or steps. Furthermore, if the image analysis detects an object that may become tangled in the brush 5103, such as a wire, the rotation of the brush 5103 can be stopped.

[0256] The display 5101 can display the remaining battery level, the amount of dust that has been sucked up, etc. The path traveled by the cleaning robot 5100 may be displayed on the display 5101. The display 5101 may also be a touch panel, and an operation button 5104 may be provided on the display 5101.

[0257] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. Images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can know the state of the room even when he or she is away from home. In addition, the display on the display 5101 can be confirmed on the portable electronic device 5140 such as a smartphone.

[0258] The light-emitting device according to one embodiment of the present invention can be used for the display 5101 .

[0259] The robot 2100 shown in FIG. 8(B) includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0260] The microphone 2102 has a function of detecting the user's speaking voice, environmental sounds, etc. The speaker 2104 has a function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104.

[0261] The display 2105 has a function of displaying various information. The robot 2100 can display information desired by the user on the display 2105. The display 2105 may be equipped with a touch panel. The display 2105 may also be a detachable information terminal, which can be installed in a fixed position on the robot 2100 to enable charging and data transfer.

[0262] The upper camera 2103 and the lower camera 2106 have a function of capturing images of the surroundings of the robot 2100. In addition, the obstacle sensor 2107 can detect the presence or absence of an obstacle in the moving direction when the robot 2100 moves forward using the moving mechanism 2108. The robot 2100 can recognize the surrounding environment and move safely using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107. The light-emitting device of one embodiment of the present invention can be used for the display 2105.

[0263] 8(C) is a diagram showing an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, a connection terminal 5006, a sensor 5007 (including a function for measuring force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared ray), a microphone 5008, a display unit 5002, a support unit 5012, and earphones 5013.

[0264] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the display portion 5002 .

[0265] 9 shows an example in which the light-emitting device described in Embodiment 2 is used in a desk lamp, which is a lighting device. The desk lamp shown in FIG. 9 includes a housing 2001 and a light source 2002, and the lighting device described in Embodiment 3 may be used as the light source 2002.

[0266] FIG. 10 shows an example in which the light-emitting device described in Embodiment 2 is used as an indoor lighting device 3001. The light-emitting device described in Embodiment 2 has high emission efficiency and can therefore be used as a lighting device with low power consumption. In addition, the light-emitting device described in Embodiment 2 can be made large in area and can therefore be used as a large-area lighting device. In addition, the light-emitting device described in Embodiment 2 is thin and can therefore be used as a thin lighting device.

[0267] The light-emitting device described in Embodiment 2 can also be mounted on a windshield or dashboard of an automobile. Figure 11 shows one mode in which the light-emitting device described in Embodiment 2 is used on a windshield or dashboard of an automobile. Display regions 5200 to 5203 are display regions provided using the light-emitting device described in Embodiment 2.

[0268] The display region 5200 and the display region 5201 are display devices equipped with the light-emitting device described in Embodiment 2, which is provided on the windshield of an automobile. The light-emitting device described in Embodiment 2 can be a so-called see-through display device, in which the opposite side can be seen through, by fabricating the first electrode and the second electrode using light-transmitting electrodes. A see-through display can be installed on the windshield of an automobile without obstructing the view. Note that when a transistor or the like is provided for driving the device, a light-transmitting transistor such as an organic transistor made of an organic semiconductor material or a transistor using an oxide semiconductor is preferably used.

[0269] The display area 5202 is a display device provided on a pillar and incorporating the light-emitting device described in Embodiment 2. By displaying an image from an imaging means provided on the vehicle body in the display area 5202, the view blocked by the pillar can be complemented. Similarly, the display area 5203 provided on the dashboard can complement the view blocked by the vehicle body by displaying an image from an imaging means provided on the outside of the vehicle, thereby compensating for blind spots and improving safety. By displaying an image to complement the invisible parts, safety can be confirmed more naturally and without discomfort.

[0270] The display area 5203 can also provide various other information such as navigation information, speed, and number of revolutions. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in the display areas 5200 to 5202. The display areas 5200 to 5203 can also be used as lighting devices.

[0271] 12A and 12B show a foldable mobile information terminal 5150. The foldable mobile information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 5153. FIG. 12A shows the mobile information terminal 5150 in an unfolded state. FIG. 12B shows the mobile information terminal in a folded state. Although the mobile information terminal 5150 has a large display area 5152, it is compact and highly portable when folded.

[0272] Display area 5152 can be folded in half by bending portion 5153. Bending portion 5153 is composed of an expandable member and multiple support members, and when folding, the expandable member stretches and bending portion 5153 is folded with a curvature radius of 2 mm or more, preferably 3 mm or more.

[0273] Note that the display region 5152 may be a touch panel (input / output device) equipped with a touch sensor (input device). The light-emitting device of one embodiment of the present invention can be used for the display region 5152.

[0274] 13(A) to 13(C) show a foldable mobile information terminal 9310. Fig. 13(A) shows the mobile information terminal 9310 in an unfolded state. Fig. 13(B) shows the mobile information terminal 9310 in a state in the process of changing from either the unfolded state or the folded state to the other. Fig. 13(C) shows the mobile information terminal 9310 in a folded state. The mobile information terminal 9310 has excellent portability in the folded state, and has excellent display visibility in the unfolded state due to its wide, seamless display area.

[0275] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. Note that the display panel 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). The display panel 9311 can be reversibly transformed from an unfolded state of the mobile information terminal 9310 to a folded state by bending the two housings 9315 via the hinges 9313. The light-emitting device of one embodiment of the present invention can be used for the display panel 9311.

[0276] Note that the structure described in this embodiment mode can be used by appropriately combining the structures described in any of Embodiment Modes 1 to 4.

[0277] As described above, the light-emitting device having the light-emitting device described in Embodiment 2 has a very wide range of application, and this light-emitting device can be applied to electronic devices in a variety of fields. By using the light-emitting device described in Embodiment 2, electronic devices with low power consumption can be obtained. [Example]

[0278] <Synthesis Example 1> This synthesis example describes a method for synthesizing N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmtBuPCA2Nbf(IV)-02), which is shown as structural formula 100 in Embodiment 1. The structural formula of 3,10mmtBuPCA2Nbf(IV)-02 is shown below.

[0279] [ka]

[0280] <Step 1: Synthesis of N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-amine> A 200 mL three-neck flask was charged with 5.5 g (14 mmol) of 2-chloro-9-(3,5-di-tert-butylphenyl)-9H-carbazole, 1.9 g (21 mmol) of aniline, 4.0 g (41 mmol) of sodium tert-butoxide, and 0.25 g (0.69 mmol) of di(1-adamantyl)-n-butylphosphine. 90 mL of xylene was added to the mixture, and the mixture was degassed by stirring under reduced pressure. 79 mg (0.14 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the mixture was heated and stirred at 150 °C for 6 hours under a nitrogen stream. After stirring, toluene was added to the mixture, and the mixture was suction-filtered through Florisil, Celite, and alumina. The filtrate was concentrated to obtain a solid. The solid was purified by silica gel column chromatography (eluent: toluene:hexane = 3:7). Ethanol was added to the resulting solid, and after ultrasonic irradiation, the solid was filtered to obtain 5.2 g of a white solid in an 83% yield. The synthesis scheme for Step 1 is shown below.

[0281] [ka]

[0282] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 1 above ( 1 The measurement results by H-NMR are shown in Figures 14(A) and (B). The numerical data are shown below. This shows that N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-amine was obtained in Step 1. 1 H NMR(DMSO-d6,300MHz):δ=1.36(s,18H),6.83(tt,J1=6.9Hz,J2=1.5Hz,1H),6.97(dd,J1=8.4Hz,J2=1.8Hz,1H),7.07 (d,J1=1.8Hz,1H),7.13-7.33(m,7H),7.39(d,J1=1.8Hz,2H),7.50(t,J1=1.8Hz,1H),8.03-8.07(m,2H),8.37(s,1H).

[0283] <Step 2: Synthesis of 3,10mmtBuPCA2Nbf(IV)-02> A 200 mL three-neck flask was charged with 0.79 g (2.1 mmol) of 3,10-dichloronaphtho[2,3-b;6,7-b']bisbenzofuran, 2.2 g (6.4 mmol) of N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-amine, 75 mg (0.21 mmol) of di(1-adamantyl)-n-butylphosphine, and 1.2 g (13 mmol) of sodium tert-butoxide. 20 mL of xylene was added to the mixture. The mixture was degassed by stirring under reduced pressure. 24 mg (42 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture and stirred at 150 °C for 14 hours under a nitrogen stream. After stirring, the mixture was filtered, and the solid was collected. The resulting solid was washed with ethanol and water. The washed solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 1:4, then toluene:hexane = 3:7) to obtain a solid. The obtained solid was recrystallized with toluene to obtain 1.6 g of a yellow solid in a yield of 66%. 1.0 g of the obtained solid was purified by train sublimation. The sublimation purification was carried out at a pressure of 2.2 × 10 -2 The reaction was carried out at 375°C under conditions of 0 Pa and 0 mL / min argon flow rate, and 0.94 g of a yellow solid was obtained with a recovery rate of 91%. The synthesis scheme for Step 2 is shown below.

[0284] [ka]

[0285] The obtained solid 1 The numerical data of H-NMR are shown below. 1 The H-NMR charts are shown in Figures 15(A) and 15(B), which demonstrate that 3,10mmtBuPCA2Nbf(IV)-02 was obtained by this synthesis example. 1H NMR(CD2Cl2,300MHz):δ=1.21(s,36H),7.05-7.16(m,6H),7.19-7.33(m,18H),7.35 -7.45(m,6H),7.89(d,J1=8.4Hz,2H),7.98(s,2H),8.05-8.11(m,4H),8.37(s,2H).

[0286] Next, the absorption and emission spectra of the toluene solution of 3,10mmtBuPCA2Nbf(IV)-02 were measured. The results are shown in Figure 16. The absorption and emission spectra of the thin film are shown in Figure 17. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (V550, JASCO Corporation). The spectrum measured with toluene alone in a quartz cell was subtracted from the absorption spectrum. The thin film was fabricated on a quartz substrate by vacuum deposition. The absorption spectrum of the thin film was measured using a spectrophotometer (U4100, Hitachi High-Technologies Corporation). The emission spectrum was measured using a fluorometer (FS920, Hamamatsu Photonics Co., Ltd.). The quantum yield was measured using an absolute PL quantum yield measurement system (Quantaurus-QY, Hamamatsu Photonics Co., Ltd.).

[0287] As shown in Figure 16, the toluene solution of 3,10mmtBuPCA2Nbf(IV)-02 exhibited absorption peaks at 433 nm, 411 nm, 384 nm, and 348 nm, with emission spectrum peaks at 450 nm and 479 nm (excitation wavelength 410 nm). Also, as shown in Figure 17, the thin film of 3,10mmtBuPCA2Nbf(IV)-02 exhibited absorption peaks at 434 nm, 414 nm, 350 nm, and 266 nm, with emission spectrum peaks at 468 nm and 494 nm (excitation wavelength 410 nm). These results confirmed that 3,10mmtBuPCA2Nbf(IV)-02 emits blue light, suggesting its potential as a host for luminescent materials and visible-light fluorescent materials.

[0288] Furthermore, the quantum yield of 3,10mmtBuPCA2Nbf(IV)-02 in a toluene solution was measured and found to be very high at 90%, indicating that it is suitable as a light-emitting material. [Example]

[0289] Example 1 In this example, a light-emitting device using an organic compound according to one embodiment of the present invention and a comparative light-emitting device not using the organic compound will be described. The structural formulae of the organic compounds used in Light-Emitting Device 1, Comparative Light-Emitting Device 1-1, and Comparative Light-Emitting Device 1-2 are shown below.

[0290] [ka]

[0291] (Method for fabricating light-emitting device 1) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the electrode area was 2 mm×2 mm.

[0292] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0293] Then, 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.

[0294] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward, and N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf) represented by the above structural formula (i) and an electron acceptor material (OCHD-001) were co-deposited on the first electrode 101 by a deposition method using resistance heating to a thickness of 10 nm in a weight ratio of 1:0.1 (=BBABnf:OCHD-001), thereby forming a hole injection layer 111.

[0295] Next, BBABnf was deposited on the hole injection layer 111 to a thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0296] Subsequently, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the structural formula (iii) above and N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmtBuPCA2Nbf(IV)-02) represented by the structural formula (iv) above were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10mmtBuPCA2Nbf(IV)-02) to form the light-emitting layer 113.

[0297] Then, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) represented by the above structural formula (v) was formed to a thickness of 15 nm on the light-emitting layer 113, and then 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) represented by the above structural formula (vi) was evaporated to a thickness of 10 nm to form the electron-transporting layer 114.

[0298] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 1 of this example.

[0299] (Method for producing comparative light-emitting device 1-1) Comparative light-emitting device 1-1 was fabricated in the same manner as light-emitting device 1, except that 3,10mmtBuPCA2Nbf(IV)-02 in light-emitting device 1 was replaced with 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02) represented by the above structural formula (vii).

[0300] (Method for producing comparative light-emitting device 1-2) Comparative light-emitting device 1-2 was fabricated in the same manner as light-emitting device 1, except that 3,10mmtBuPCA2Nbf(IV)-02 in light-emitting device 1 was replaced with N,N'-bis[9-(3,5-diethylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmEtPCA2Nbf(IV)-02) represented by the above structural formula (viii).

[0301] The device structure of the above light-emitting device is summarized in the table below.

[0302] [Table 1]

[0303] The above light-emitting device was sealed with a glass substrate in a nitrogen atmosphere glove box to prevent the light-emitting device from being exposed to the atmosphere (a sealant was applied around the element, and UV treatment and heat treatment at 80°C for 1 hour were performed during sealing), and then the initial characteristics were measured.

[0304] The luminance-current density characteristics of light-emitting device 1, comparative light-emitting device 1-1, and comparative light-emitting device 1-2 are shown in Figure 18, their current efficiency-luminance characteristics in Figure 19, their luminance-voltage characteristics in Figure 20, their current-voltage characteristics in Figure 21, their external quantum efficiency-luminance characteristics in Figure 22, and their emission spectra in Figure 23. 2 The main characteristics of the vicinity are listed below.

[0305] [Table 2]

[0306] 18 to 23 show that the light-emitting device 1 of one embodiment of the present invention, the comparative light-emitting device 1-1, and the comparative light-emitting device 1-2 are all EL devices with high emission efficiency.

[0307] Here, the emission spectra and thermal properties of 3,10mmtBuPCA2Nbf(IV)-02, an organic compound according to one embodiment of the present invention, used as the light-emitting material of light-emitting device 1, 3,10PCA2Nbf(IV)-02 used as the light-emitting material of comparative light-emitting device 1-1, 3,10mmEtPCA2Nbf(IV)-02 used as the light-emitting material of comparative light-emitting device 1-2, and N,N'-bis[9-(3,5-dihexylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmHexPCA2Nbf(IV)-02) represented by the following structural formula (ix) were investigated.

[0308] [ka]

[0309] 3,10mmtBuPCA2Nbf(IV)-02, an organic compound represented by the structural formula (iv) above, is a substance in which two tert-butyl groups are substituted at the meta-position on the phenyl group substituted at the 9-position of the carbazolyl group in 3,10PCA2Nbf(IV)-02, an organic compound represented by the structural formula (vii) above. 3,10mmEtPCA2Nbf(IV)-02, an organic compound represented by the structural formula (viii) above, is a substance in which an ethyl group is substituted at the same position. 3,10mmHexPCA2Nbf(IV)-02, an organic compound represented by the structural formula (ix) above, is a substance in which an n-hexyl group is substituted.

[0310] First, the emission spectra of these four substances in toluene solution are shown in Figure 24. As can be seen from Figure 24, the peaks in the emission spectra of these four substances are all at similar positions, and the spectral shapes are almost identical. This means that even if the above-mentioned substituents are introduced into the phenyl group substituted at the 9-position of the carbazolyl group in these four substances, it does not affect the conjugation of the substance itself, nor does it affect the emission color.

[0311] Specifically, 3,10PCA2Nbf(IV)-02 exhibits blue emission with good color purity, while 3,10mmtBuPCA2Nbf(IV)-02, 3,10mmEtPCA2Nbf(IV)-02, and 3,10mmHexPCA2Nbf(IV)-02 exhibit blue emission with good color purity, with the introduction of substituents having little effect on the emission or absorption spectra. On the other hand, 3,10PCA2Nbf(IV)-02 also contains an arylamine bonded to the main backbone, which is the luminophore. However, the introduction of a similar substituent to the phenyl group of this arylamine shifts the emission spectrum to longer wavelengths, resulting in a decrease in color purity.

[0312] Next, thermogravimetry-differential thermal analysis (TG-DTA) was performed on these four substances. A high-vacuum differential thermobalance (TG-DTA2410SA, manufactured by Bruker AXS) was used for the measurements. Figure 25 shows the relationship between weight loss and temperature (thermogravimetry) measured under conditions of 10 Pa and a heating rate of 10°C / min. Table 3 also shows the temperatures (weight loss temperatures) at which the weights of the above organic compounds were -5%, -10%, and -50% of the charged amount.

[0313] [Table 3]

[0314] Table 3 shows that the weight loss temperature of 3,10PCA2Nbf(IV)-02, in which two alkyl groups are substituted at the meta-position on the phenyl group at the 9-position of the carbazolyl group, tends to decrease, indicating improved sublimation. In particular, 3,10mmtBuPCA2Nbf(IV)-02, in which two tBu groups are substituted at the meta-position, showed the greatest improvement in sublimation.

[0315] In addition, the current density is 50mA / cm 2 A graph showing the change in luminance with respect to the driving time in the comparative light-emitting device 1-1 and the light-emitting device 1 according to one embodiment of the present invention both exhibited better characteristics than the comparative light-emitting device 1-2.

[0316] Since 3,10mmHexPCA2Nbf(IV)-02 was decomposed during purification by sublimation, a light-emitting device using 3,10mmHexPCA2Nbf(IV)-02 could not be fabricated, and therefore no device data is available.

[0317] As described above, the organic compound of one embodiment of the present invention has a secondary or tertiary alkyl group, the carbon of which is branched and bonded to the phenyl group, bonded to the meta position of the phenyl group bonded to the 9-position of the carbazolyl group, and thereby has good sublimation properties and enables the fabrication of a highly reliable light-emitting device.

[0318] The results of measuring the solubility of 3,10PCA2Nbf(IV)-02 and 3,10mmtBuPCA2Nbf(IV)-02 in solvents are shown below. The table shows the results of examining the solubility in toluene at 25°C. As described above, the organic compound of one embodiment of the present invention was found to have improved solubility in solvents due to the attachment of two branched secondary or tertiary alkyl groups having 3 to 6 carbon atoms to the meta-position of the phenyl group attached to the 9-position of the carbazolyl group, making it an organic compound that is easy to purify and produce.

[0319] [Table 4]

[0320] The melting points and glass transition temperatures of 3,10mmtBuPCA2Nbf(IV)-02 and 3,10PCA2Nbf(IV)-02 were measured using a differential scanning calorimeter (DSC, PerkinElmer Pyris1). The measurement results indicated that the melting point of 3,10mmtBuPCA2Nbf(IV)-02 was 391°C and the glass transition temperature was 201°C. The melting point of 3,10PCA2Nbf(IV)-02 was 366°C and the glass transition temperature was 184°C. Thus, the organic compound of one embodiment of the present invention exhibits a high melting point and a high glass transition temperature, and has good heat resistance, due to the attachment of two branched secondary or tertiary alkyl groups having 3 to 6 carbon atoms to the meta-position of the phenyl group attached to the 9-position of the carbazolyl group. [Example]

[0321] In this example, a light-emitting device 2 using an organic compound of one embodiment of the present invention and a comparative light-emitting device 2 not using the organic compound will be described. The structural formulae of the organic compounds used in the light-emitting device 2 and the comparative light-emitting device 2 are shown below.

[0322] [ka]

[0323] (Method for fabricating light-emitting device 2) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the electrode area was 2 mm×2 mm.

[0324] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0325] Then, 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.

[0326] 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-(1,1'-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 (x) and an electron acceptor material (OCHD-001) were co-deposited on the first electrode 101 by a deposition method using resistance heating to a thickness of 10 nm so as to have a weight ratio of 1:0.03 (= PCBBiF:OCHD-001) to form a hole injection layer 111.

[0327] Next, PCBBiF was deposited on the hole injection layer 111 to a thickness of 20 nm, and then N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP) represented by the above structural formula (xi) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0328] Subsequently, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the structural formula (iii) above and N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmtBuPCA2Nbf(IV)-02) represented by the structural formula (iv) above were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10mmtBuPCA2Nbf(IV)-02) to form the light-emitting layer 113.

[0329] Then, on the light-emitting layer 113, 6-(1,1'-biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm) represented by the above structural formula (xii) was formed to a thickness of 10 nm, and further, 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) represented by the above structural formula (xiii) and 8-hydroxyquinolinato-lithium (abbreviation: Liq) represented by the above structural formula (xiv) were co-deposited to a thickness of 15 nm so as to give a weight ratio of 1:1 (=mPn-mDMePyPTzn:Liq), to form an electron-transporting layer 114.

[0330] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 2 of this example.

[0331] (Method for producing comparative light-emitting device 2) Comparative light-emitting device 2 was fabricated in the same manner as light-emitting device 2, except that 3,10mmtBuPCA2Nbf(IV)-02 in light-emitting device 2 was replaced with 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02) represented by the above structural formula (vii).

[0332] The device structure of the above light-emitting device is summarized in the table below.

[0333] [Table 5]

[0334] The above light-emitting device was sealed with a glass substrate in a nitrogen atmosphere glove box to prevent the light-emitting device from being exposed to the atmosphere (a sealant was applied around the element, and UV treatment and heat treatment at 80°C for 1 hour were performed during sealing), and then the initial characteristics were measured.

[0335] The luminance-current density characteristics of light-emitting device 2 and comparative 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-voltage characteristics in Figure 30, the external quantum efficiency-luminance characteristics in Figure 31, and the emission spectrum in Figure 32. 2 The main characteristics of the vicinity are listed below.

[0336] [Table 6]

[0337] 27 to 32 show that the light-emitting device 2 of one embodiment of the present invention and the comparative light-emitting device 2 are both EL devices with favorable characteristics.

[0338] Furthermore, a light-emitting device having the same structure as light-emitting device 2 and comparative light-emitting device 2 had a current density of 50 mA / cm 2 The change in luminance with respect to drive time was measured at 25°C and 85°C. The results are shown in Figure 33. The measurements were performed under two conditions, 25°C and 85°C, and Figure 33 shows the results under both conditions. As shown in Figure 33, the results of the measurement at 25°C for Light-emitting Device 2 and Comparative Light-emitting Device 2 were almost similar, with both exhibiting good reliability. However, the results of the measurement at 85°C showed a clear difference between Light-emitting Device 2 and Comparative Light-emitting Device 2, with Light-emitting Device 2, a light-emitting device according to one embodiment of the present invention, exhibiting better reliability.

[0339] These results indicate that the light-emitting device using the organic compound of one embodiment of the present invention has high reliability at high temperatures, and therefore the organic compound of one embodiment of the present invention has high heat resistance. [Example]

[0340] In this example, a light-emitting device 3 including an organic compound according to one embodiment of the present invention will be described. The structural formula of the organic compound used in the light-emitting device 3 is shown below.

[0341] [ka]

[0342] (Method for fabricating light-emitting device 3) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the electrode area was 2 mm×2 mm.

[0343] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0344] Then, 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.

[0345] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward, and N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf) represented by the above structural formula (i) and an electron acceptor material (OCHD-001) were co-deposited on the first electrode 101 by a deposition method using resistance heating to a thickness of 10 nm in a weight ratio of 1:0.1 (=BBABnf:OCHD-001), thereby forming a hole injection layer 111.

[0346] Next, BBABnf was deposited on the hole injection layer 111 to a thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0347] Subsequently, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the structural formula (iii) above and N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmtBuPCA2Nbf(IV)-02) represented by the structural formula (iv) above were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10mmtBuPCA2Nbf(IV)-02) to form the light-emitting layer 113.

[0348] Then, on the light-emitting layer 113, 6-(1,1'-biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm) represented by the above structural formula (xii) was formed to a thickness of 10 nm, and further, 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) represented by the above structural formula (xiii) and 8-hydroxyquinolinato-lithium (abbreviation: Liq) represented by the above structural formula (xiv) were co-deposited to a thickness of 15 nm so as to give a weight ratio of 1:1 (=mPn-mDMePyPTzn:Liq), to form an electron-transporting layer 114.

[0349] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 3 of this example.

[0350] The device structure of the above light-emitting device is summarized in the table below.

[0351] [Table 7]

[0352] The above light-emitting device was sealed with a glass substrate in a nitrogen atmosphere glove box to prevent the light-emitting device from being exposed to the atmosphere (a sealant was applied around the element, and UV treatment and heat treatment at 80°C for 1 hour were performed during sealing), and then the initial characteristics were measured.

[0353] The luminance-current density characteristics of light-emitting device 3 are shown in Figure 34, the current efficiency-luminance characteristics in Figure 35, the luminance-voltage characteristics in Figure 36, the current-voltage characteristics in Figure 37, the external quantum efficiency-luminance characteristics in Figure 38, and the emission spectrum in Figure 39. 2 The main characteristics of the vicinity are listed below.

[0354] [Table 8]

[0355] 34 to 39 show that the light-emitting device 3 of one embodiment of the present invention is an EL device with favorable characteristics.

[0356] Furthermore, a light-emitting device having the same structure as light-emitting device 3 had a current density of 50 mA / cm 2 The change in luminance with respect to the operating time at 25°C and 85°C was measured. The results are shown in Figure 40. The measurements were carried out under two conditions, 25°C and 85°C, and Figure 40 shows the reliability results for both. As shown in Figure 40, Light-Emitting Device 3 showed very good reliability results at both temperatures.

[0357] These results demonstrate that the light-emitting device using the organic compound of one embodiment of the present invention has high reliability. [Example]

[0358] <Synthesis Example 2> In this synthesis example, a synthesis method for N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-yl]-N,N'-diphenyl-pyrene-1,6-diamine (abbreviation: 1,6mmtBuPCAPrn-03), an organic compound of one embodiment of the present invention, is described. The structural formula of 1,6mmtBuPCAPrn-03 is shown below.

[0359] [ka]

[0360] <Step 1: Synthesis of 4-bromo-9-(3,5-di-tert-butylphenyl)-9H-carbazole> A 200 mL three-neck flask was charged with 10 g (41 mmol) of 4-bromo-9H-carbazole, 20 g (73 mmol) of 1-bromo-3,5-di-tert-butylbenzene, 0.77 g (4.1 mmol) of copper(I) iodide, 11 g (81 mmol) of potassium carbonate, 0.32 g (1.2 mmol) of 18-crown-6-ether, and 10 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU). The mixture was stirred at 180 °C for 7 h under a nitrogen stream. After stirring, 100 mL of toluene was added to the mixture. The precipitate was removed by suction filtration. The filtrate was washed sequentially with dilute hydrochloric acid, water, and saturated aqueous sodium bicarbonate. The organic and aqueous layers were separated, and the organic layer was dried over magnesium sulfate. The mixture was filtered, and the filtrate was concentrated to give an oil. This oil was purified by silica gel column chromatography (eluent: hexane). Methanol was added to the resulting solid, and after ultrasonic irradiation, the solid was collected to obtain 19 g of a white solid. The synthesis scheme of Step 1 is shown below.

[0361] [ka]

[0362] <Step 2: Synthesis of N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-amine (abbreviation: mmtBuPCA-03)> A 200 mL three-neck flask was charged with 6.0 g (14 mmol) of 4-bromo-9-(3,5-di-tert-butylphenyl)-9H-carbazole, 1.9 g (21 mmol) of aniline, and 4.0 g (15 mmol) of sodium tert-butoxide. To this mixture was added 70 mL of toluene and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine. The mixture was degassed by stirring under reduced pressure. To this mixture was added 79 mg (0.14 mmol) of bis(dibenzylideneacetone)palladium(0), and the mixture was heated and stirred at 120 °C for 7 hours under a nitrogen stream. After stirring, toluene was added to the mixture, which was then suction filtered through Florisil, Celite, and alumina. The filtrate was concentrated to obtain a solid. This solid was purified by silica gel column chromatography (developing solvent: toluene:hexane=1:5, then toluene:hexane=1:3) to obtain 5.1 g of a white solid in an 82% yield. The synthesis scheme of Step 2 is shown below.

[0363] [ka]

[0364] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 The results of H-NMR are shown in Figures 43(A) and (B). Figure 43(B) is a graph showing an enlarged view of the range from 6.5 ppm to 8.5 ppm in Figure 43(A). Numerical data is shown below. This shows that N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-amine was obtained in Step 2. 1H NMR(DMSO-d6,300MHz):δ=1.38(s,18H),6.79(tt,J1=7.2Hz,1H),6.98(d,J1=7.8Hz,2H),7.06(dd,J1=5.1Hz,J2 =7.8Hz,2H),7.11-7.22(m,3H),7.31-7.42(m,5H),7.56(t,J1=1.8Hz,1H),7.96(d,J1=7.8Hz,1H),8.26(s,1H).

[0365] <Step 3: Synthesis of 1,6mmtBuPCAPrn-03> A 200 mL three-neck flask was charged with 0.99 g (2.8 mmol) of 1,6-dibromopyrene, 3.1 g (6.9 mmol) of N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-amine, and 1.9 g (19 mmol) of sodium tert-butoxide. To this mixture, 30 mL of toluene and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine were added and degassed by stirring under reduced pressure. 32 mg (55 μmol) of bis(dibenzylideneacetone)palladium(0) was added and heated and stirred at 120 °C for 20.5 hours under a nitrogen stream. After stirring, toluene was added to the mixture, which was then suction filtered through Florisil, Celite, and alumina to obtain the filtrate. The resulting filtrate was concentrated to obtain a solid. This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene = 7:3) to obtain a solid. The obtained solid was recrystallized with toluene to obtain 1.1 g of a yellow solid in a yield of 38%. The obtained 1.1 g of solid was purified by train sublimation (conditions: pressure 4.0 × 10 -2 The reaction mixture was heated to 355°C (Pa, argon flow rate 0 mL / min, 355°C). After purification by sublimation, 1.0 g of a yellow solid was obtained with a recovery rate of 88%. The synthesis scheme for Step 3 is shown below.

[0366] [ka]

[0367] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 above ( 1The results of H-NMR are shown in Figures 44(A) and (B). Figure 44(B) is a graph showing an enlarged view of the range from 6.5 ppm to 8.5 ppm in Figure 44(A). Numerical data are shown below. This demonstrates that 1,6mmtBuPCAPrn-03 was obtained by this synthesis example. 1 H NMR(CDCl3,300MHz):δ=1.41(s,36H),6.77-6.89(m,6H),6.96-7.05(m,4H),7.10(t,J1=7.8Hz,2H),7.17-7.23(m,6H),7.32-7.42(m,4H), 7.45(d,J1=1.8Hz,4H),7.52(t,J1=1.8Hz,2H),7.80-7.85(m,4H),7.95(d,J1=7.8Hz,2H),8.02(d,J1=8.1Hz,2H),8.26(d,J1=9.3Hz,2H).

[0368] Next, the absorption and emission spectra of the toluene solution of 1,6mmtBuPCAPrn-03 were measured, and the results are shown in Figure 45. The absorption and emission spectra of the thin film are also shown in Figure 46. The solid thin film was prepared on a quartz substrate by vacuum deposition. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (V550, manufactured by JASCO Corporation) and the spectrum measured with only toluene in a quartz cell was subtracted. The absorption spectrum of the thin film was measured using a spectrophotometer (U4100, manufactured by Hitachi High-Technologies Corporation). The emission spectrum was measured using a fluorometer (FP-8600, manufactured by JASCO Corporation). The quantum yield was measured using an absolute PL quantum yield measurement system (Quantaurus-QY, manufactured by Hamamatsu Photonics K.K.).

[0369] As shown in Figure 45, the toluene solution of 1,6mmtBuPCAPrn-03 exhibited absorption peaks at 425 nm, 355 nm, and 282 nm, with an emission spectrum peak at 456 nm (excitation wavelength 400 nm). Furthermore, as shown in Figure 46, the thin film of 1,6mmtBuPCAPrn-03 exhibited absorption peaks at 430 nm, 398 nm, 335 nm, 315 nm, 295 nm, and 265 nm, with emission spectrum peaks at 470 nm, 491 nm, and 535 nm (excitation wavelength 400 nm). These results confirmed that 1,6mmtBuPCAPrn-03 emits blue light, demonstrating its potential as a host for luminescent materials and fluorescent materials in the visible region.

[0370] Furthermore, when the quantum yield in a toluene solution was measured, it was found to be extremely high at 86%, indicating that the compound is suitable as a light-emitting material. [Example]

[0371] <Synthesis Example 3> This synthesis example describes a synthesis method for N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-yl]-N,N'-diphenyl-7-phenyl-7H-dibenzo[c,g]carbazole-5,9-diamine (abbreviation: 5,9mmtBuPCA2PcgDBC-03), an organic compound of one embodiment of the present invention. The structural formula of 5,9mmtBuPCA2PcgDBC-03 is shown below.

[0372] [ka]

[0373] <Step 1: Synthesis of 4-bromo-9-(3,5-di-tert-butylphenyl)-9H-carbazole> The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 2 in Example 5.

[0374] <Step 2: Synthesis of N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-amine> The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 2 in Example 5.

[0375] <Step 3: Synthesis of 5,9mmtBuPCA2PcgDBC-03> A 200 mL three-neck flask was charged with 0.81 g (1.6 mmol) of 5,9-dibromo-7-phenyldibenzo[c,g]carbazole, 1.7 g (3.9 mmol) of N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-amine, and 0.93 g (9.7 mmol) of sodium tert-butoxide. To this mixture was added 20 mL of toluene and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine. The mixture was degassed by stirring under reduced pressure. To this mixture was added 19 mg (32 μmol) of bis(dibenzylideneacetone)palladium(0), and the mixture was heated and stirred at 110 °C for 14.5 hours under a nitrogen stream. After stirring, toluene was added to the mixture, which was then suction filtered through Florisil, Celite, and alumina to obtain the filtrate. The resulting filtrate was concentrated to obtain a solid. This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene = 3:1, then hexane:toluene = 3:2). The obtained solid was recrystallized with ethyl acetate / ethanol to obtain 1.7 g of a yellow solid in 83% yield. 1.4 g of the obtained solid was purified by train sublimation. -2 The reaction was carried out at 350°C under conditions of 0 Pa and 0 mL / min argon flow rate. After purification by sublimation, 1.2 g of a yellow solid was obtained with a recovery rate of 86%. The synthesis scheme for Step 3 is shown below.

[0376] [ka]

[0377] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 above ( 1The results of H-NMR are shown in Figures 47(A) and (B). Figure 47(B) is a graph showing an enlarged view of the range from 6.5 ppm to 9.5 ppm in Figure 47(A). Numerical data are shown below. This demonstrates that 5,9mmtBuPCA2PcgDBC-03 was obtained by this synthesis example. 1 H NMR(DMSO-d6,300MHz):δ=1.38(s,36H),6.60(d,J1=6.9Hz,2H),6.83-6.88(m,4H),6.95-7.09(m,6H),7.1 9-7.45(m,23H),7.57(t,J1=1.5Hz,2H),7.67-7.75(m,4H),8.26(d,J1=8.4Hz,2H),9.18(d,J1=8.4Hz,2H).

[0378] Next, the absorption and emission spectra of the toluene solution of 5,9mmtBuPCA2PcgDBC-03 were measured, and the results are shown in Figure 48. The absorption and emission spectra of the thin film are also shown in Figure 49. The solid thin film was prepared on a quartz substrate by vacuum deposition. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (V550, manufactured by JASCO Corporation) and the spectrum measured with only toluene in a quartz cell was subtracted. The absorption spectrum of the thin film was measured using a spectrophotometer (U4100, manufactured by Hitachi High-Technologies Corporation). The emission spectrum was measured using a fluorometer (FP-8600, manufactured by JASCO Corporation). The quantum yield was measured using an absolute PL quantum yield measurement system (Quantaurus-QY, manufactured by Hamamatsu Photonics K.K.).

[0379] As shown in Figure 48, the toluene solution of 5,9mmtBuPCA2PcgDBC-03 exhibited absorption peaks at 422 nm, 352 nm, and 282 nm, with emission spectrum peaks at 455 nm and 480 nm (excitation wavelength 422 nm). Furthermore, as shown in Figure 49, the thin film of 5,9mmtBuPCA2PcgDBC-03 exhibited absorption peaks at 422 nm, 356 nm, and 275 nm, with emission spectrum peaks at 471 nm and 495 nm (excitation wavelength 400 nm). These results confirmed that 5,9mmtBuPCA2PcgDBC-03 emits blue light, demonstrating its potential as a host for luminescent materials and visible-light-emitting fluorescent materials.

[0380] Furthermore, when the quantum yield in a toluene solution was measured, it was found to be extremely high at 82%, indicating that the compound is suitable as a light-emitting material. [Example]

[0381] <Synthesis Example 4> This synthesis example describes a synthesis method for N-(dibenzofuran-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-(3,5-di-tert-butylphenyl)-9H-carbazol-3-amine (abbreviation: FrFAmmtBuPC), which is an organic compound of one embodiment of the present invention and is represented by structural formula (166) in Embodiment 1. The structural formula of FrFAmmtBuPC is shown below.

[0382] [ka]

[0383] <Step 1: Synthesis of N-(9,9-dimethylfluoren-2-yl)-9-(3,5-di-tert-butylphenyl)-9H-carbazol-3-amine> A 1000 mL three-neck flask was charged with 15 g (35 mmol) of 3-bromo-9-(3,5-di-tert-butylphenyl)-9H-carbazole, 11 g (52 mmol) of 2-amino-9,9-dimethylfluorene, and 10 g (0.10 mol) of sodium tert-butoxide. To this mixture, 175 mL of toluene and 0.4 mL of a 10% hexane solution of tri(tert-butyl)phosphine were added, and the mixture was degassed by stirring under reduced pressure. 0.20 g (0.35 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the mixture was heated and stirred at 110 °C for 7 hours under a nitrogen stream. After stirring, toluene was added to the mixture, and the mixture was suction-filtered through Florisil, Celite, and alumina to obtain the filtrate. The resulting filtrate was concentrated to an oil. This oil was purified by silica gel column chromatography (eluent: hexane:toluene = 2:1, then hexane:toluene = 3:2) to obtain 4.0 g of a pale brown solid in a yield of 21%. The remaining solid was purified by silica gel column chromatography (eluent: hexane:ethyl acetate = 100:1) to obtain 3.6 g of a pale brown solid in a yield of 18%. The synthesis scheme for Step 1 is shown below.

[0384] [ka]

[0385] Nuclear magnetic resonance spectroscopy of the light brown solid obtained in step 2 above ( 1 The results of H-NMR are shown in Figures 50(A) and 50(B). Note that Figure 50(B) is a graph showing an enlarged view of the range from 6.5 ppm to 8.5 ppm in Figure 50(A). Numerical data is also shown below. This shows that N-(9,9-dimethylfluoren-2-yl)-9-(3,5-di-tert-butylphenyl)-9H-carbazol-3-amine was obtained by Step 1. 1H NMR(DMSO-d6,300MHz):δ=1.38(s,18H),1.41(s,6H),7.03(dd,J1=8.4Hz,J2=2.1Hz,1H),7.16-7.30(m,5H),7.37-7.4 7(m,6H),7.54(t,J1=1.5Hz,1H),7.63(d,J1=8.1Hz,2H),8.01(d,J1=1.8Hz,1H),8.17(d,J1=7.8Hz,1H),8.23(s,1H).

[0386] <Step 2: Synthesis of FrFAmmtBuPC> A 200 mL three-neck flask was charged with 3.7 g (6.2 mmol) of N-(9,9-dimethylfluoren-2-yl)-9-(3,5-di-tert-butylphenyl)-9H-carbazol-3-amine, 1.1 g (4.1 mmol) of 4-bromodibenzofuran, and 1.2 g (12 mmol) of sodium tert-butoxide. To this mixture, 20 mL of toluene and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine were added, and the mixture was degassed by stirring under reduced pressure. 35 mg (67 μmol) of bis(dibenzylideneacetone)palladium(0) was added and heated and stirred at 110 °C for 6.5 hours under a nitrogen stream. After stirring, toluene was added to the mixture, which was then suction-filtered through Florisil, Celite, and alumina to obtain the filtrate. The resulting filtrate was concentrated to obtain a solid. This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene = 3:1). The resulting solid was recrystallized with ethyl acetate / ethanol to obtain 2.2 g of a white solid in a 72% yield. The filtrate from the recrystallization was concentrated, and the resulting solid was recrystallized with ethyl acetate / ethanol to obtain 0.51 g of a white solid in a 17% yield. 2.6 g of the resulting solid was purified by train sublimation. The process was carried out under conditions of a pressure of 3.7 Pa and an argon flow rate of 15 mL / min at 265 °C. After sublimation purification, 2.3 g of a white solid was obtained in an 89% recovery rate. The synthesis scheme for Step 2 is shown below.

[0387] [ka]

[0388] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 The results of H-NMR are shown in Figures 51(A) and 51(B). Figure 51(B) is a graph showing an enlarged view of the range from 6.5 ppm to 8.5 ppm in Figure 51(A). Numerical data are shown below. This demonstrates that FrFAmmtBuPC was obtained by this synthesis example. 1 H NMR(DMSO-d6,300MHz):δ=1.26(s,6H),1.37(s,18H),6.81(dd,J1=8.4Hz,J2=2.4Hz,1H),7.01(d,J1=1.8Hz,1H),7. 18-7.49(m,15H),7.54(t,J1=1.8Hz,1H),7.63-7.68(m,2H),7.95(dd,J1=7.8Hz,J2=1.2Hz,1H),8.15-8.19(m,3H).

[0389] Next, the absorption and emission spectra of a toluene solution of FrFAmmtBuPC were measured, and the results are shown in Figure 52. The absorption and emission spectra of the thin film are shown in Figure 53. A solid thin film was prepared on a quartz substrate by vacuum deposition. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (V550, manufactured by JASCO Corporation), and the spectrum measured with only toluene in a quartz cell was subtracted from the measured spectrum. The absorption spectrum of the thin film was measured using a spectrophotometer (U4100, manufactured by Hitachi High-Technologies Corporation). The emission spectrum was measured using a fluorometer (FP-8600, manufactured by JASCO Corporation).

[0390] As shown in Figure 52, the toluene solution of FrFAmmtBuPC exhibited absorption peaks at 342 nm, 325 nm, 310 nm, and 282 nm, with an emission spectrum peak at 418 nm (excitation wavelength 325 nm). Also, as shown in Figure 53, the thin film of FrFAmmtBuPC exhibited absorption peaks at 384 nm, 340 nm, and 280 nm, with an emission spectrum peak at 425 nm (excitation wavelength 340 nm). [Example]

[0391] <Synthesis Example 5> This synthesis example describes a synthesis method for N-(9,9-dimethyl-9H-fluoren-2-yl)-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazole]-3,3′-amine (abbreviation: mmtBuPCzPCFL), an organic compound of one embodiment of the present invention, which is represented by structural formula (174) in Embodiment 1. The structural formula of mmtBuPCzPCFL is shown below.

[0392] [ka]

[0393] <Step 1: Synthesis of N-(9,9-dimethylfluoren-2-yl)-9-(3,5-di-tert-butylphenyl)-9H-carbazol-3-amine> The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 4 in Example 7.

[0394] <Step 2: Synthesis of mmtBuPCzPCFL> A 200 mL three-neck flask was charged with 2.8 g (4.9 mmol) of N-(9,9-dimethylfluoren-2-yl)-9-(3,5-di-tert-butylphenyl)-9H-carbazol-3-amine, 1.4 g (3.3 mmol) of 3-bromo-9-(3,5-di-tert-butylphenyl)-9H-carbazole, and 0.94 g (9.8 mmol) of sodium tert-butoxide. To this mixture was added 20 mL of toluene and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine. The mixture was degassed by stirring under reduced pressure. To this mixture was added 19 mg (33 μmol) of bis(dibenzylideneacetone)palladium(0), and the mixture was heated and stirred at 110 °C under a nitrogen stream for 6.5 hours. After stirring, toluene was added to the mixture, which was then suction filtered through Florisil, Celite, and alumina to obtain the filtrate. The filtrate was concentrated to obtain a solid. This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene = 3:1). The obtained solid was recrystallized with ethyl acetate / ethanol to obtain 2.7 g of a white solid in a 91% yield. The obtained 2.7 g of solid was purified by train sublimation. The process was carried out under conditions of a pressure of 3.3 Pa and an argon flow rate of 15 mL / min at 305 °C. After sublimation purification, 2.6 g of a pale yellow solid was obtained in a 95% recovery rate. The synthesis scheme for Step 2 is shown below.

[0395] [ka]

[0396] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 The results of H-NMR are shown in Figures 54(A) and (B). Figure 54(B) is a graph showing an enlarged view of the range from 6.5 ppm to 8.5 ppm in Figure 54(A). Numerical data are shown below. This demonstrates that mmtBuPCzPCFL was obtained by this synthesis example. 1H NMR(DMSO-d6,300MHz):δ=1.30(s,6H),1.36(s,36H),6.86(dd,J1=8.4Hz,J2=2.1Hz,1H),7.14(d,J1=2.1Hz,1H),7.1 6-7.23(m,3H),7.24-7.34(m,3H),7.36-7.45(m,11H),7.54(t,J1=1.8Hz,2H),7.60-7.66(m,2H),8.01-8.14(m,4H).

[0397] Next, the absorption and emission spectra of a toluene solution of mmtBuPCzPCFL were measured, and the results are shown in Figure 55. The absorption and emission spectra of the thin film are shown in Figure 56. A solid thin film was prepared on a quartz substrate by vacuum deposition. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (V550, manufactured by JASCO Corporation), and the spectrum measured by placing only toluene in a quartz cell was subtracted from the measured spectrum. The absorption spectrum of the thin film was measured using a spectrophotometer (U4100, manufactured by Hitachi High-Technologies Corporation). The emission spectrum was measured using a fluorometer (FP-8600, manufactured by JASCO Corporation).

[0398] As shown in Figure 55, the toluene solution of mmtBuPCzPCFL exhibited absorption peaks at 361 nm, 323 nm, and 287 nm, and the emission spectrum peaked at 441 nm (excitation wavelength 323 nm). Also, as shown in Figure 56, the thin film of mmtBuPCzPCFL exhibited absorption peaks at 420 nm, 365 nm, 324 nm, and 294 nm, and the emission spectrum peaked at 444 nm (excitation wavelength 360 nm). [Example]

[0399] In this example, a light-emitting device 4 including an organic compound according to one embodiment of the present invention will be described. The structural formula of the organic compound used in the light-emitting device 4 is shown below.

[0400] [ka]

[0401] (Method for fabricating light-emitting device 4) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the electrode area was 2 mm×2 mm.

[0402] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0403] Then, 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.

[0404] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward, and N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf) represented by the above structural formula (i) and an electron acceptor material (OCHD-001) were co-deposited on the first electrode 101 by a deposition method using resistance heating to a thickness of 10 nm in a weight ratio of 1:0.1 (=BBABnf:OCHD-001), thereby forming a hole injection layer 111.

[0405] Next, BBABnf was deposited on the hole injection layer 111 to a thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0406] Subsequently, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the structural formula (iii) above and N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-yl]-N,N'-diphenyl-pyrene-1,6-diamine (abbreviation: 1,6mmtBuPCAPrn-03) represented by the structural formula (xv) above were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=αN-βNPAnth:1,6mmtBuPCAPrn-03) to form the light-emitting layer 113.

[0407] Thereafter, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (xvi) was formed to a thickness of 10 nm on the light-emitting layer 113, and further, 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) represented by the above structural formula (xiii) and 8-hydroxyquinolinato-lithium (abbreviation: Liq) represented by the above structural formula (xiv) were co-deposited to a thickness of 15 nm so as to give a weight ratio of 1:1 (=mPn-mDMePyPTzn:Liq), to form an electron-transporting layer 114.

[0408] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 4 of this example.

[0409] The device structure of the above light-emitting device is summarized in the table below.

[0410] [Table 9]

[0411] The above light-emitting device was sealed with a glass substrate in a nitrogen atmosphere glove box to prevent the light-emitting device from being exposed to the atmosphere (a sealant was applied around the element, and UV treatment and heat treatment at 80°C for 1 hour were performed during sealing), and then the initial characteristics were measured.

[0412] The luminance-current density characteristics of light-emitting device 4 are shown in Figure 57, the current efficiency-luminance characteristics in Figure 58, the luminance-voltage characteristics in Figure 59, the current-voltage characteristics in Figure 60, the external quantum efficiency-luminance characteristics in Figure 61, and the emission spectrum in Figure 62. 2 The main characteristics of the vicinity are listed below.

[0413] [Table 10]

[0414] 57 to 62 show that the light-emitting device 4 of one embodiment of the present invention is an EL device with favorable characteristics. [Example]

[0415] In this example, a light-emitting device 5 including an organic compound according to one embodiment of the present invention will be described. The structural formula of the organic compound used in the light-emitting device 5 is shown below.

[0416] [ka]

[0417] (Method for fabricating light-emitting device 5) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 70 nm, and the electrode area was 2 mm×2 mm.

[0418] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0419] Then, 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.

[0420] Next, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward, and N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf) represented by the above structural formula (i) and an electron acceptor material (OCHD-001) were co-deposited on the first electrode 101 by a deposition method using resistance heating to a thickness of 10 nm in a weight ratio of 1:0.1 (=BBABnf:OCHD-001), thereby forming a hole injection layer 111.

[0421] Next, BBABnf was deposited on the hole injection layer 111 to a thickness of 20 nm, and then 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) represented by the above structural formula (ii) was deposited to a thickness of 10 nm to form the hole transport layer 112.

[0422] Subsequently, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth) represented by the structural formula (iii) above and N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-4-yl]-N,N'-diphenyl-7-phenyl-7H-dibenzo[c,g]carbazole-5,9-diamine (abbreviation: 5,9mmtBuPCA2PcgDBC-03) represented by the structural formula (xvii) above were co-deposited to a thickness of 25 nm in a weight ratio of 1:0.03 (=αN-βNPAnth:5,9mmtBuPCA2PcgDBC-03) to form the light-emitting layer 113.

[0423] Thereafter, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (xvi) was formed to a thickness of 10 nm on the light-emitting layer 113, and further, 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) represented by the above structural formula (xiii) and 8-hydroxyquinolinato-lithium (abbreviation: Liq) represented by the above structural formula (xiv) were co-deposited to a thickness of 15 nm so as to give a weight ratio of 1:1 (=mPn-mDMePyPTzn:Liq), to form an electron-transporting layer 114.

[0424] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 5 of this example.

[0425] The element structure of the light-emitting device 5 is summarized in the table below.

[0426] [Table 11]

[0427] The above-mentioned light-emitting device 5 was sealed with a glass substrate in a glove box with a nitrogen atmosphere to prevent the light-emitting device from being exposed to the atmosphere (a sealant was applied around the element, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), and then the initial characteristics were measured.

[0428] The luminance-current density characteristics of light-emitting device 5 are shown in Figure 63, the current efficiency-luminance characteristics in Figure 64, the luminance-voltage characteristics in Figure 65, the current-voltage characteristics in Figure 66, the external quantum efficiency-luminance characteristics in Figure 67, and the emission spectrum in Figure 68. In addition, the 1000 cd / m 2 The main characteristics of the vicinity are listed below.

[0429] [Table 12]

[0430] 63 to 68 show that the light-emitting device 5 of one embodiment of the present invention is an EL device with favorable characteristics. [Example]

[0431] In this example, a light-emitting device 6 and a light-emitting device 7 each using an organic compound according to one embodiment of the present invention will be described. The structural formulae of the organic compounds used in the light-emitting device 6 and the light-emitting device 7 are shown below.

[0432] [ka]

[0433] (Method for fabricating light-emitting device 6) First, indium tin oxide containing silicon oxide (ITSO) was formed on a glass substrate by sputtering to form a first electrode 101. The thickness of the first electrode 101 was 110 nm, and the electrode area was 2 mm×2 mm.

[0434] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0435] Then, 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.

[0436] 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-(1,1'-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 (x) and an electron acceptor material (OCHD-001) were co-deposited on the first electrode 101 by a deposition method using resistance heating to a thickness of 10 nm so as to have a weight ratio of 1:0.03 (= PCBBiF:OCHD-001) to form a hole injection layer 111.

[0437] Next, PCBBiF was deposited on the hole injection layer 111 to a thickness of 100 nm, and then N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethylfluoren-2-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: oFBiSF(2)) represented by the above structural formula (xviii) was deposited to a thickness of 90 nm to form the hole transport layer 112.

[0438] Next, 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr) represented by the structural formula (xix), N-(9,9-dimethyl-9H-fluoren-2-yl)-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazole]-3,3'-amine (abbreviation: mmtBuPCzPCFL) which is an organic compound of one embodiment of the present invention represented by the structural formula (xx), and bis{4,6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κN) represented by the structural formula (xxi) were prepared. 2O,O')iridium(III) (abbreviation: [Ir(dmdppr-m5CP)2(dpm)]) was co-deposited at a weight ratio of 0.6:0.4:0.1 (=9mDBtBPNfpr:mmtBuPCzPCFL:[Ir(dmdppr-m5CP)2(dpm)]) to a thickness of 50 nm to form the light-emitting layer 113.

[0439] Thereafter, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (xvi) was formed to a thickness of 10 nm on the light-emitting layer 113, and further, 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) represented by the above structural formula (xiii) and 8-hydroxyquinolinato-lithium (abbreviation: Liq) represented by the above structural formula (xiv) were co-deposited to a thickness of 25 nm so as to give a weight ratio of 1:1 (=mPn-mDMePyPTzn:Liq) to form an electron-transporting layer 114.

[0440] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby producing the light-emitting device 6 of this example.

[0441] (Method for fabricating light-emitting device 7) Light-emitting device 7 was fabricated in the same manner as light-emitting device 6, except that mmtBuPCzPCFL in light-emitting device 6 was changed to N-(dibenzofuran-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-(3,5-di-tert-butylphenyl)-9H-carbazol-3-amine (abbreviation: FrFAmmtBuPC), which is an organic compound according to one embodiment of the present invention and is represented by structural formula (xxii) above.

[0442] The device structures of the light-emitting devices 6 and 7 are summarized in the table below.

[0443] [Table 13]

[0444] The above-mentioned light-emitting devices 6 and 7 were sealed with glass substrates in a glove box with a nitrogen atmosphere to prevent the light-emitting devices from being exposed to the atmosphere (a sealant was applied around the elements, and UV treatment was performed during sealing, followed by heat treatment at 80°C for 1 hour), and then their initial characteristics were measured.

[0445] The luminance-current density characteristics of light-emitting device 6 and light-emitting device 7 are shown in Figure 69, the current efficiency-luminance characteristics in Figure 70, the luminance-voltage characteristics in Figure 71, the current-voltage characteristics in Figure 72, the external quantum efficiency-luminance characteristics in Figure 73, and the emission spectrum in Figure 74. 2 The main characteristics of the vicinity are listed below.

[0446] [Table 14]

[0447] 69 to 74 show that the light-emitting devices 6 and 7 of one embodiment of the present invention are EL devices with favorable characteristics.

[0448] (Reference example 1) ≪Reference synthesis example 1≫ This Reference Synthesis Example describes a method for synthesizing N,N'-bis[9-(3,5-diethylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmEtPCA2Nbf(IV)-02), which was used in Example 2. The structural formula of 3,10mmEtPCA2Nbf(IV)-02 is shown below.

[0449] [ka]

[0450] Step 1: Synthesis of 2-chloro-9-(3,5-diethylphenyl)-9H-carbazole A 300 mL three-neck flask was charged with 3.2 g (16 mmol) of 2-chloro-9H-carbazole, 5.0 g (23 mmol) of 1-bromo-3,5-diethylbenzene, and 4.5 g (47 mmol) of sodium tert-butoxide. To this mixture, 80 mL of xylene and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine were added, and the mixture was degassed by stirring under reduced pressure. 90 mg (0.16 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the mixture was heated and stirred at 150 °C for 7 hours under a nitrogen stream. After stirring, toluene was added to the mixture, and the mixture was suction-filtered through Florisil, Celite, and alumina to obtain the filtrate. The resulting filtrate was concentrated to obtain an oil. This oil was purified by silica gel column chromatography (eluent: hexane) to obtain 4.8 g of a colorless, transparent oil in 93% yield. The synthesis scheme for Step 1 is shown below.

[0451] [ka]

[0452] The colorless, transparent oil obtained in step 1 was analyzed by nuclear magnetic resonance spectroscopy ( 1 The results of measurement by H-NMR are shown below, which indicated that 2-chloro-9-(3,5-diethylphenyl)-9H-carbazole was obtained in Step 1. 1 H NMR(CDCl3,300MHz):δ=1.31(t,J1=7.5Hz,6H),2.75(q,J1=7.5Hz,4H),7.12(s,3H),7.22-7.31(m,2H) ,7.36-7.44(m,3H),8.03(dd,J1=8.1Hz,J2=0.3Hz,1H),8.25(ddd,J1=7.8Hz,J2=1.2Hz,J3=0.9Hz,1H).

[0453] <Step 2: Synthesis of N-[9-(3,5-diethylphenyl)-9H-carbazol-2-yl]-N-phenylamine> A 300 mL three-neck flask was charged with 4.8 g (14 mmol) of 2-chloro-9-(3,5-diethylphenyl)-9H-carbazole, 2.0 g (22 mmol) of aniline, 4.2 g (43 mmol) of sodium tert-butoxide, and 0.26 g (0.72 mmol) of di(1-adamantyl)-n-butylphosphine. 75 mL of xylene was added to the mixture, and the mixture was degassed by stirring under reduced pressure. 83 mg (0.14 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the mixture was heated and stirred at 150 °C for 7 hours under a nitrogen stream. After stirring, toluene was added to the mixture, and the mixture was suction-filtered through Florisil, Celite, and alumina. The filtrate was concentrated to obtain a solid. The solid was purified by silica gel column chromatography (eluent: toluene:hexane = 3:7, then toluene:hexane = 2:3). Ethanol and hexane were added to the resulting oil, and after ultrasonic irradiation, the precipitated solid was collected to give 3.9 g of a white solid in 69% yield. The synthetic scheme for Step 2 is shown below.

[0454] [ka]

[0455] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 The results of measurement by H-NMR are shown below, which indicated that N-[9-(3,5-diethylphenyl)-9H-carbazol-2-yl]-N-phenylamine was obtained in Step 2. 1 H NMR (DMSO-d6,300MHz):δ=1.25(t,J1=7.8Hz,6H),2.70(q,J1=7.8Hz,4H),6.82(t,J1=7.2Hz,1H),7.00(d d,J1=8.4Hz,J2=1.8Hz,1H),7.07(d,J1=1.8Hz,1H),7.12-7.31(m,10H),8.02-8.07(m,2H),8.37(s,1H).

[0456] <Step 3: Synthesis of 3,10mM EtPCA2Nbf(IV)-02> A 200 mL three-neck flask was charged with 0.87 g (2.3 mmol) of 3,10-dichloronaphtho[2,3-b;6,7-b']bisbenzofuran, 2.2 g (5.5 mmol) of N-[9-(3,5-diethylphenyl)-9H-carbazol-2-yl]-N-phenylamine, 82 mg (0.23 mmol) of di(1-adamantyl)-n-butylphosphine, and 1.3 g (14 mmol) of sodium tert-butoxide. 25 mL of xylene was added to the mixture. The mixture was degassed by stirring under reduced pressure. 26 mg (46 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture and stirred at 150 °C for 14 hours under a nitrogen stream. After stirring, toluene was added to the mixture, which was then suction filtered through Florisil, Celite, and alumina. The filtrate was concentrated to obtain a solid. The obtained solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 1:2) to obtain a solid. The obtained solid was recrystallized with toluene / ethyl acetate to obtain 1.88 g of a yellow solid in a yield of 75%. 1.2 g of the obtained solid was purified by train sublimation at a pressure of 2.2 × 10 -2 The reaction was carried out at 385°C under conditions of 0 Pa and 0 mL / min argon flow rate. After purification by sublimation, 0.93 g of a yellow solid was obtained with a recovery rate of 78%. The synthesis scheme for Step 3 is shown below.

[0457] [ka]

[0458] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 above ( 1 The results of H-NMR are shown below, which indicate that 3,10mmEtPCA2Nbf(IV)-02 was obtained in step 3. 1H NMR(CD2Cl2,300MHz):δ=1.12(t,J1=7.8Hz,12H),2.60(q,J1=7.8Hz,8H),7.01(s,2H),7.06-7.13 (m,10H),7.20-7.44(m,18H),7.89(d,J1=8.4Hz,2H),7.97(s,2H),8.04-8.10(m,4H),8.36(s,2H).

[0459] Next, the absorption and emission spectra of the toluene solution of 3,10 mm EtPCA2Nbf(IV)-02 were measured. The results are shown in Figure 41. The absorption and emission spectra of the thin film are shown in Figure 42. Solid thin films were prepared on quartz substrates by vacuum deposition. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (V550, JASCO Corporation). The spectrum was obtained by subtracting the spectrum measured with toluene alone in a quartz cell. The absorption spectrum of the thin film was measured using a spectrophotometer (U4100, Hitachi High-Technologies Corporation). The emission spectrum was measured using a fluorometer (FP-8600, JASCO Corporation). The quantum yield was measured using an absolute PL quantum yield measurement system (Quantaurus-QY, Hamamatsu Photonics K.K.).

[0460] As shown in Figure 41, the toluene solution of 3,10mmEtPCA2Nbf(IV)-02 exhibited absorption peaks at 433 nm, 411 nm, 348 nm, 322 nm, and 280 nm, with emission spectrum peaks at 451 nm and 478 nm (excitation wavelength 408 nm). Furthermore, as shown in Figure 42, the thin film of 3,10mmEtPCA2Nbf(IV)-02 exhibited absorption peaks at 436 nm, 418 nm, 348 nm, 322 nm, and 280 nm, with an emission spectrum peak at 480 nm (excitation wavelength 400 nm). These results confirmed that 3,10mmEtPCA2Nbf(IV)-02 emits blue light, suggesting its potential as a host for luminescent materials and visible-light fluorescent materials.

[0461] Furthermore, the quantum yield of 3,10mmEtPCA2Nbf(IV)-02 in toluene solution was measured and found to be very high at 88%, indicating that it is suitable as a light-emitting material.

[0462] (Reference example 2) ≪Reference synthesis example 2≫ This Reference Synthesis Example describes a synthesis method for N,N'-bis[9-(3,5-dihexylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmHexPCA2Nbf(IV)-02), which was used in Example 2. The structural formula of 3,10mmHexPCA2Nbf(IV)-02 is shown below.

[0463] [ka]

[0464] <Step 1: Synthesis of 2-chloro-9-(3,5-dihexylphenyl)-9H-carbazole> A 300 mL three-neck flask was charged with 2.9 g (14 mmol) of 2-chloro-9H-carbazole, 8.4 g (26 mmol) of 1-bromo-3,5-dihexylbenzene, and 4.2 g (43 mmol) of sodium tert-butoxide. To this mixture, 75 mL of xylene and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine were added, and the mixture was degassed by stirring under reduced pressure. To this mixture, 82 mg (10.14 mmol) of bis(dibenzylideneacetone)palladium(0) was added, and the mixture was heated and stirred at 150 °C under a nitrogen stream for 1.5 hours. After stirring, toluene was added to the mixture, and the mixture was suction-filtered through Florisil, Celite, and alumina to obtain the filtrate. The resulting filtrate was concentrated to an oil. This oil was purified by silica gel column chromatography (silica gel, developing solvent: hexane) to obtain 1.4 g of a colorless, transparent oil in a yield of 22%. The synthesis scheme of Step 1 is shown below.

[0465] [ka]

[0466] Nuclear magnetic resonance spectroscopy ( 1 The results of measurement by H-NMR are shown below, which indicated that 2-chloro-9-(3,5-dihexylphenyl)-9H-carbazole was obtained in Step 1. 1 H NMR(CDCl3,300MHz):δ=0.89(t,J1=6.9Hz,6H),1.29-1.43(m,12H),1.68(quin,J1=7.8Hz,4H),2.69(t,J1=7 .8Hz,4H),7.11-7.31(m,5H),7.36-7.44(m,3H),8.03(d,J1=8.4Hz,1H),8.09(dt,J1=7.8Hz,J2=0.9Hz,1H).

[0467] <Step 2: Synthesis of N-[9-(3,5-dihexylphenyl)-9H-carbazol-2-yl]-N-phenylamine> A 200 mL three-neck flask was charged with 1.4 g (3.1 mmol) of 2-chloro-9-(3,5-dihexylphenyl)-9H-carbazole, 0.55 g (5.9 mmol) of aniline, 0.90 g (9.4 mmol) of sodium tert-butoxide, and 56 mg (0.16 mmol) of di(1-adamantyl)-n-butylphosphine. 20 mL of xylene was added to the mixture, and the mixture was degassed by stirring under reduced pressure. 18 mg (31 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the mixture was heated and stirred at 150 °C for 7 hours under a nitrogen stream. After stirring, toluene was added to the mixture, which was then suction filtered through Florisil, Celite, and alumina. The filtrate was concentrated to give a brown oil.

[0468] A 200 mL three-neck flask was charged with 2.7 g (6.1 mmol) of 2-chloro-9-(3,5-dihexylphenyl)-9H-carbazole, 0.85 g (9.1 mmol) of aniline, 1.8 g (18 mmol) of sodium tert-butoxide, and 0.11 g (0.30 mmol) of di(1-adamantyl)-n-butylphosphine. 30 mL of xylene was added to the mixture, and the mixture was degassed by stirring under reduced pressure. 35 mg (61 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the mixture was heated and stirred at 150 °C for 7 hours under a nitrogen stream. After stirring, toluene was added to the mixture, which was then suction filtered through Florisil, Celite, and alumina. The filtrate was concentrated to give a brown oil. The two batches of oil were combined and purified by silica gel column chromatography (eluent: toluene:hexane = 1:4) to give 1.7 g of a yellow solid in a 31% yield. The synthesis scheme for Step 2 is shown below.

[0469] [ka]

[0470] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 2 above ( 1 The results of measurement by H-NMR are shown below, which indicated that N-[9-(3,5-dihexylphenyl)-9H-carbazol-2-yl]-N-phenylamine was obtained in Step 2. 1 H NMR(DMSO-d6,300MHz):δ=0.84(t,J1=7.2Hz,6H),1.23-1.35(m,12H),1.62(quin,J1=7.8Hz,4H),2.66(t,J1=7.8Hz,4H),6.81(tt,J1=6.9Hz,J 2=1.2Hz,1H),6.99(dd,J1=8.7Hz,J2=1.8Hz,1H),7.07(d,J1=1.8Hz,1H ),7.11-7.15(m,3H),7.18-7.32(m,7H),8.02-8.07(m,2H),8.35(s,1H).

[0471] <Step 3: Synthesis of 3,10mmHexPCA2Nbf(IV)-02> A 200 mL three-neck flask was charged with 0.54 g (1.4 mmol) of 3,10-dichloronaphtho[2,3-b;6,7-b']bisbenzofuran, 1.7 g (3.4 mmol) of N-[9-(3,5-dihexylphenyl)-9H-carbazol-2-yl]-N-phenylamine, 51 mg (0.14 mmol) of di(1-adamantyl)-n-butylphosphine, and 0.83 g (8.6 mmol) of sodium tert-butoxide. 15 mL of xylene was added to the mixture. The mixture was degassed by stirring under reduced pressure. 16 mg (29 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture and stirred at 150 °C for 14.5 hours under a nitrogen atmosphere. After stirring, toluene was added to the mixture, which was then suction filtered through Florisil, Celite, and alumina. The filtrate was concentrated to obtain a solid. The resulting solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 1:2). The resulting solid was reprecipitated with ethyl acetate / ethanol to obtain 1.7 g of a yellow solid in 93% yield. The synthesis scheme for Step 3 is shown below.

[0472] [ka]

[0473] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 above ( 1 The results of H-NMR are shown below, which indicate that 3,10mmHexPCA2Nbf(IV)-02 was obtained in step 3. 1 H NMR(CD2Cl2,300MHz):δ=0.83(t,J1=6.6Hz,12H),1.17-1.31(m,24H),1.47-1.57(m,8H),2.55(t,J1=7.8Hz,8H),6.98 (s,2H),7.06-7.13(m,10H),7.20-7.43(m,18H),7.88(d,J1=8.4Hz,2H),7.96(s,2H),8.04-8.09(m,4H),8.35(s,2H). [Explanation of symbols]

[0474] 101 first electrode 102 second electrode 103 EL layer 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 116 Charge generation layer 117 P type layer 118 Electronic Relay Layer 119 Electron injection buffer layer 400 boards 401 First electrode 403 EL layer 404 Second electrode 405 Sealing material 406 Sealing material 407 Sealing substrate 412 Pad 420 IC chip 501 Anode 502 Cathode 511 First Light Emitting Unit 512 Second Light Emitting Unit 513 Charge generation layer 601 Driver circuit section (source line driver circuit) 602 Pixel section 603 Drive circuit section (gate line drive circuit) 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (Flexible Printed Circuit) 610 Element substrate 611 Switching FET 612 Current control FET 613 First electrode 614 Insulators 616 EL layer 617 Second electrode 618 Light-emitting devices 951 PCB 952 Electrode 953 Insulation Layer 954 Partition layer 955 EL layer 956 Electrode 1001 board 1002 Undercoat insulating film 1003 Gate insulating film 1006 Gate electrode 1007 Gate electrode 1008 gate electrode 1020 First interlayer insulating film 1021 Second interlayer insulating film 1022 Electrode 1024W First electrode 1024R First electrode 1024G First electrode 1024B First electrode 1025 Bulkhead 1028 EL layer 1029 Second electrode 1031 Sealing substrate 1032 Sealing material 1033 Transparent substrate 1034R Red color layer 1034G Green color layer 1034B Blue color layer 1035 Black Matrix 1036 Overcoat layer 1037 Third interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Periphery 2001 Case 2002 light source 2100 Robot 2110 Arithmetic equipment 2101 Illuminance sensor 2102 Microphone 2103 Upper Camera 2104 Speaker 2105 Display 2106 Lower Camera 2107 Obstacle Sensor 2108 Moving mechanism 3001 Lighting equipment 5000 cabinets 5001 Display section 5002 Display section 5003 Speaker 5004 LED lamp 5006 Connection terminal 5007 Sensor 5008 Microphone 5012 Support part 5013 Earphones 5100 Cleaning Robot 5101 Display 5102 Camera 5103 Brush 5104 Operation button 5150 Personal Digital Assistant 5151 Case 5152 Display area 5153 Bend 5120 Garbage 5200 display area 5201 Display area 5202 Display area 5203 Display area 7101 Housing 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 keyboard 7205 External connection port 7206 Pointing Device 7210 Second display unit 7401 Housing 7402 Display section 7403 Operation button 7404 External connection port 7405 Speaker 7406 Microphone 9310 Mobile Information Terminal 9311 Display Panel 9313 Hinge 9315 chassis

Claims

1. An organic compound represented by the following general formula (G1): 【Chemical 1】 (However, in the above general formula (G1), X １ and X ２ each independently represents a secondary or tertiary alkyl group having 3 to 6 carbon atoms, and the carbon atom bonded to the phenyl group is branched. １ represents a substituted or unsubstituted fused aromatic ring skeleton having 10 to 60 carbon atoms and three or more rings, or a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and two or more rings, Ar ２ represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. １ ~R ７ are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. n is any one of 1 to 3, and when n is 2 or more, Ar １ The two or more groups bonded to may be the same or different.

2. In claim 1, The Ar １ is a substituted or unsubstituted fused aromatic ring skeleton having 10 to 60 carbon atoms and 3 to 9 rings, or a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and 3 to 9 rings.

3. In claim 1 or claim 2, The Ar １ an organic compound in which the carbon atom is a substituted or unsubstituted fused heteroaromatic ring skeleton having 8 to 60 carbon atoms and 3 to 7 rings.

4. In any one of claims 1 to 3, The X １ Or the X ２ are each independently a secondary or tertiary alkyl group having 3 or 4 carbon atoms and having a branched carbon atom bonded to the phenyl group.

5. In any one of claims 1 to 4, An organic compound in which n is 2.

6. In any one of claims 1 to 5, The Ar １ is any one of the fused heteroaromatic ring skeletons represented by the following general formulas (B1) to (B4): 【Chemistry 2】 (However, in the formula, Q １ and Q ２ Each independently represents an oxygen atom or a sulfur atom. １０ ~R ２１ In the general formula (B2), one or two of R represents a single bond, and the remaining R each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. ３０ ~R ４１ One or two of the groups represented by R represent a single bond, and the remaining groups each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. ５０ ~R ６１ One or two of the following groups represent a single bond, and the remaining groups each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. ７０ ~R ８１ one or two of the above represent a single bond, and the remaining groups each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms.

7. In any one of claims 1 to 5, The Ar １ is a condensed heteroaromatic ring skeleton represented by the following general formula (B1-1) or (B3-1): 【Chemistry 3】 (However, in the formula, Q １ and Q ２ each independently represents an oxygen atom or a sulfur atom. １２ , R １８ , R ５２ and R ５８ represents a single bond.)

8. An organic compound represented by the following general formula (G1-1): 【Chemistry 4】 (However, in the above general formula (G1-1), X ３ ~X ６ Each of Ar and Arg independently represents a secondary or tertiary alkyl group having 3 to 6 carbon atoms, the carbon atom bonded to the phenyl group being branched. ２１ and Ar ２２ each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

9. A light-emitting device comprising an organic compound according to any one of claims 1 to 8.

10. An optical device comprising the organic compound according to any one of claims 1 to 8.

11. A light emitting device according to claim 9; An electronic device having a sensor, an operation button, a speaker, or a microphone.

12. A light emitting device according to claim 9; A light-emitting device having a transistor or a substrate.

13. A lighting device comprising the light-emitting device according to claim 9 and a housing.

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