Organic compound and method for synthesizing same

Abstract

To provide a 1,10 - phenanthroline derivative or a 2,2' - bipyridine derivative which has substituents at symmetrical positions and in which the substituents are different from each other.SOLUTION: Organic compounds represented by General Formula (G1) or General Formula (G2) are provided. In the formula, any one of X2 to X5 and X6 to X9 represents a halogen or a trifluoromethanesulfonyl group, and the others represent hydrogen. Any one of R2 to R5 and R6 to R9 represents an aliphatic cyclic amino group. Note that the position of a carbon atom to which a halogen or a trifluoromethanesulfonyl group is bonded and the position of a carbon atom to which an aliphatic cyclic amino group is bonded are line-symmetric in the main skeleton (1,10 phenanthroline skeleton or 2,2 ' - bipyridine skeleton).SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] One aspect of the present invention relates to an organic compound, an organic electronic device, a light-emitting device, an organic EL device, an electronic device, and a method for synthesizing an organic compound.

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

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

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

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

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

[0007] [Patent Document 1] Chinese Patent No. 111943949 [Non-patent literature]

[0008] [Non-Patent Document 1] Abel Anton S et al, “1,10-Phenanthroline Carboxylic Acids for Preparation of Functionalized Metal-Organic Frameworks”, Asian Journal of Organic Chemistry ,2019,8(11),pp.2128-2142 Summary of the Invention [Problem to be solved by the invention]

[0009] An object of one aspect of the present invention is to provide a synthetic method for easily introducing different substituents into symmetric positions of a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative.

[0010] Another aspect of the present invention is to provide an organic compound in which different substituents are introduced at symmetric positions of a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative.Another aspect of the present invention is to provide an organic compound in which an aliphatic cyclic amino group is introduced at one of symmetric positions of a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative and a substituent different from the aliphatic cyclic amino group (hereinafter also referred to as substituent A) is introduced at the other symmetric position.

[0011] Another object of the present invention is to provide a novel phenanthroline derivative or bipyridine derivative, or a method for synthesizing the novel phenanthroline derivative or bipyridine derivative.

[0012] Note that the description of these problems does not preclude the existence of other problems. One embodiment of the present invention does not necessarily have to solve all of these problems. Problems other than these can be extracted from the description in the specification, drawings, and claims. [Means for solving the problem]

[0013] One embodiment of the present invention is an organic compound represented by general formula (G1) or general formula (G2).

[0014] [ka]

[0015] However, in the above general formula (G1) or general formula (G2), X 2 ~X 5 or X 6 ~X 9 One of the groups is a halogen or a trifluoromethanesulfonyl group, and the rest are hydrogen. 2 ~R 5 or R 6 ~R 9one of which represents an aliphatic cyclic amino group represented by the following general formula (g1), and the rest represent hydrogen, provided that the position of the carbon substituted with a halogen or trifluoromethanesulfonyl group and the position of the carbon substituted with a group represented by the following general formula (g1) are positioned in line symmetry in the main skeleton (1,10-phenanthroline skeleton or 2,2'-bipyridine skeleton).

[0016] [ka]

[0017] In the above general formula (g1), R 11 ~R 18 each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18 Any two of these may be bonded to each other to form a ring.

[0018] Another embodiment of the present invention is an organic compound represented by any one of General Formulas (G1-1) to (G1-4).

[0019] [ka]

[0020] In the above general formulae (G1-1) to (G1-4), X represents a halogen or a trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the following general formula (g1).

[0021] [ka]

[0022] In the above general formula (g1), R 11 ~R 18 each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18 Any two of these may be bonded to each other to form a ring.

[0023] Another embodiment of the present invention is an organic compound represented by any one of General Formulas (G2-1) to (G2-4).

[0024] [ka]

[0025] In the above general formulae (G2-1) to (G2-4), X represents a halogen or a trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the following general formula (g1).

[0026] [ka]

[0027] In the above general formula (g1), R 11 ~R 18each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18 Any two of these may be bonded to each other to form a ring.

[0028] Another embodiment of the present invention is an organic compound represented by General Formula (G3).

[0029] [ka]

[0030] In the general formula (G3), R is a group represented by the following general formula (g1), and A is a group represented by the following general formula (g2) or (g3). In the general formula (G3), the substituent A and the substituent R are different substituents.

[0031] [ka]

[0032] In the above general formulas (g1) and (g2), R 11 ~R 18 , R 21 ~R 28each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p, q, s, and t each independently represent 0 to 3. 11 ~R 18 Any two of, and R 21 ~R 28 Any two of these may be bonded to each other to form a ring. Furthermore, the aliphatic cyclic amino group represented by the general formula (g2) may be condensed with an aromatic ring having 6 to 10 carbon atoms. In the general formula (g3), Z represents any one of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted monovalent heteroaromatic ring group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and m represents an integer of 1 to 3. When m is 2 or greater, the multiple Zs may be the same or different groups. Furthermore, L represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, and n represents an integer of 0 to 3. When n is 2 or more, multiple Ls may be the same group or different groups.

[0033] Another embodiment of the present invention is an organic compound represented by general formula (G3-1).

[0034] [ka]

[0035] However, in the above general formula (G3-1), R 11 ~R 18 and R 21 ~R 28 each independently represents any one of hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p, q, s, and t each independently represent 0 to 3. 11 ~R 18 Any two of, and R 21 ~R 28 Any two of these may be bonded to each other to form a ring. In addition, one of the aliphatic cyclic amino groups in the general formula (G3-1) may be condensed with an aromatic ring having 6 to 10 carbon atoms. In the general formula (G3-1), the substituents bonded to the 4-position and the 7-position of the 1,10-phenanthroline skeleton are different from each other.

[0036] Another embodiment of the present invention is an organic compound represented by general formula (G3-2).

[0037] [ka]

[0038] In the above general formula (G3-2), R 11 ~R 18each independently represents any one of hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18 Any two of these may be bonded to each other to form a ring. Z represents any one of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted monovalent heteroaromatic ring group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, or a carbonyl group, and m represents an integer of 1 to 3. When m is 2 or more, the multiple Zs may be the same or different groups. Furthermore, L represents a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, and n represents an integer of 0 to 3. When n is 2 or more, multiple Ls may be the same group or different groups.

[0039] Another aspect of the present invention is a method for synthesizing a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative having substituents at two symmetrical carbon atoms, each of which is different from the other, the method comprising the step of reacting a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative having a halogen or a trifluoromethanesulfonyl group at two symmetrical carbon atoms, respectively, with an aliphatic cyclic amine, using an inorganic base and a solvent.

[0040] Another embodiment of the present invention is a method for synthesizing a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative having different substituents on two symmetric carbon atoms, the method comprising the step of heating a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative having a halogen or a triflate group on each of two symmetric carbon atoms with an aliphatic cyclic amine using potassium carbonate or potassium acetate as a solvent to cause the derivative to react with the 1,10-phenanthroline derivative or the 2,2′-bipyridine derivative.

[0041] Alternatively, another aspect of the present invention is a method for synthesizing a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative having a substituent at each of two symmetric carbons, each of which is different from the other, the method including: a first step of reacting a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative having a halogen or a triflate group at two symmetric carbons with an aliphatic cyclic amine using potassium carbonate or potassium acetate as a solvent to obtain a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative in which an aliphatic cyclic amine is bonded to one of the symmetric carbons and a halogen or a triflate group is bonded to the other of the symmetric carbons; and a second step of introducing another substituent to the other of the symmetric carbons.

[0042] Another embodiment of the present invention is a method for synthesizing a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative having different substituents on two carbon atoms at symmetrical positions, using N-methyl-2-pyrrolidone as a solvent in the above configuration.

[0043] Another embodiment of the present invention is an organic semiconductor device including any one of the organic compounds described above.

[0044] Another embodiment of the present invention is a light-emitting device including any of the above organic compounds.

[0045] Another embodiment of the present invention is a light-receiving device including any one of the organic compounds described above.

[0046] Another aspect of the present invention is an organic electronic device using any one of the organic compounds described above in a capping layer.

[0047] Another aspect of the present invention is an electronic device including the organic electronic device. [Effects of the Invention]

[0048] In one embodiment of the present invention, a synthetic method can be provided for easily introducing different substituents into symmetric positions of a 1,10-phenanthroline derivative or a 2,2′-bipyridine derivative.

[0049] Alternatively, in another embodiment of the present invention, an organic compound can be provided in which different substituents are introduced into two carbon atoms at line-symmetric positions of a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative. Alternatively, in another embodiment of the present invention, an organic compound can be provided in which an aliphatic cyclic amino group is introduced into one carbon atom of two line-symmetric positions of a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative, and a substituent different from the aliphatic cyclic amino group (hereinafter also referred to as substituent A) is introduced into the other carbon atom.

[0050] Alternatively, in another aspect of the present invention, a novel phenanthroline derivative or bipyridine derivative can be provided, or a method for synthesizing the novel phenanthroline derivative or bipyridine derivative can be provided.

[0051] According to one embodiment of the present invention, a novel light-emitting device, a novel display device, a novel display module, and a novel electronic device can be provided.

[0052] Note that the description of these effects does not preclude the existence of other effects. One embodiment of the present invention does not necessarily have all of these effects. Effects other than these can be extracted from the description in the specification, drawings, and claims. [Brief explanation of the drawings]

[0053] [Figure 1] 1A to 1C are diagrams showing a light-emitting device. [Figure 2] 2(A) and 2(B) are a top view and a cross-sectional view of the light-emitting device. [Figure 3] 3A and 3B are perspective views showing configuration examples of a display module. [Figure 4] 4(A) and 4(B) are cross-sectional views showing examples of the configuration of a display device. [Figure 5] FIG. 5 is a perspective view showing an example of the configuration of a display device. [Figure 6] FIG. 6 is a cross-sectional view showing an example of the configuration of a display device. [Figure 7] FIG. 7 is a cross-sectional view showing an example of the configuration of a display device. [Figure 8] FIG. 8 is a cross-sectional view showing an example of the configuration of a display device. [Figure 9] 9A to 9D are diagrams showing examples of electronic devices. [Figure 10] 10A to 10F are diagrams showing examples of electronic devices. [Figure 11] 11A to 11G are diagrams showing examples of electronic devices. [Figure 12] 12(A) to 12(C) are diagrams showing 1H NMR charts of 4Cl7HidPhen. [Figure 13] 13(A) to 13(C) are diagrams showing 1H NMR charts of Hid2Phen. [Figure 14] 14(A) to 14(C) are diagrams showing 1H NMR charts of 4Cl7PrdPhen. [Figure 15]15(A) to 15(C) are diagrams showing 1H NMR charts of 4Br7HidPhen. [Figure 16] 16(A) to 16(C) are diagrams showing 1H NMR charts of 4Br7PrdPhen. [Figure 17] 17(A) to 17(C) are diagrams showing 1H NMR charts of 2Cl9HidPhen. [Figure 18] 18(A) to 18(C) are diagrams showing 1H NMR charts of 4Cl4'HidBpy. [Figure 19] 19(A) to 19(C) are diagrams showing 1H NMR charts of Hid-DPPrdPhen. [Figure 20] 20(A) to 20(C) are diagrams showing 1H NMR charts of Hid-αNPrdPhen. [Figure 21] 21(A) to 21(C) are diagrams showing the 1H NMR charts of Hid-αNPPhen. [Figure 22] 22(A) to 22(C) are diagrams showing 1H NMR charts of Hid-ceHBazPhen. [Figure 23] FIG. 23 is a graph showing the luminance-current density characteristics of the light-emitting device 1-1, the light-emitting device 1-2, and the comparative light-emitting device 1. In FIG. [Figure 24] FIG. 24 is a graph showing the current efficiency-luminance characteristics of the light-emitting device 1-1, the light-emitting device 1-2, and the comparative light-emitting device 1. In FIG. [Figure 25] FIG. 25 is a graph showing the luminance-voltage characteristics of the light-emitting device 1-1, the light-emitting device 1-2, and the comparative light-emitting device 1. In FIG. [Figure 26] FIG. 26 is a graph showing the current density-voltage characteristics of the light-emitting device 1-1, the light-emitting device 1-2, and the comparative light-emitting device 1. In FIG. [Figure 27] FIG. 27 shows electroluminescence spectra of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1. As shown in FIG. [Figure 28]FIG. 28 is a graph showing the luminance-current density characteristics of the light-emitting device 2-1, the light-emitting device 2-2, and the comparative light-emitting device 2. In FIG. [Figure 29] FIG. 29 is a graph showing the current efficiency-luminance characteristics of the light-emitting device 2-1, the light-emitting device 2-2, and the comparative light-emitting device 2. In FIG. [Figure 30] FIG. 30 is a graph showing the luminance-voltage characteristics of the light-emitting device 2-1, the light-emitting device 2-2, and the comparative light-emitting device 2. In FIG. [Figure 31] FIG. 31 is a graph showing the current density-voltage characteristics of the light-emitting device 2-1, the light-emitting device 2-2, and the comparative light-emitting device 2. In FIG. [Figure 32] FIG. 32 shows electroluminescence spectra of light-emitting device 2-1, light-emitting device 2-2, and comparative light-emitting device 2. As shown in FIG. [Figure 33] Figures 33(A) to 33(C) show the 1H NMR charts of Hid-AcuPhen. DETAILED DESCRIPTION OF THE INVENTION

[0054] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it will be readily understood by those skilled in the art that various changes can be made in form and detail without departing from the spirit and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the description of the embodiments shown below.

[0055] Furthermore, ordinal numbers such as "first" and "second" used in this specification are used to avoid confusion between components, and do not indicate any order or ranking, such as the order of processes or stacking. Even if a term does not have an ordinal number in this specification, an ordinal number may be used in the claims to avoid confusion between components. Even if a term has an ordinal number in this specification, a different ordinal number may be used in the claims. Even if a term has an ordinal number in this specification, the ordinal number may be omitted in the claims.

[0056] In this specification and the like, a photoluminescence (PL) spectrum refers to a spectrum obtained in fluorometry by fixing the excitation wavelength of excitation light and scanning the emission wavelength to measure the emission intensity. It may also be called an emission spectrum. The emission spectrum may contain fluorescent components and phosphorescent components. In this specification and the like, an emission spectrum consisting of fluorescent components may be particularly called a fluorescence spectrum, and an emission spectrum consisting of phosphorescent components may be particularly called a phosphorescent spectrum.

[0057] (Embodiment 1) 1,10-Phenanthroline derivatives and 2,2'-bipyridine derivatives have good electron transport properties and are therefore widely used as materials for organic semiconductor devices such as organic electroluminescent devices (synonymous with light-emitting devices in this specification). For example, 1,10-phenanthroline derivatives such as bathophenanthroline (abbreviated as BPhen) and 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as NBPhen) have high electron transport properties and have been widely used for a long time.

[0058] Furthermore, 1,10-phenanthroline derivatives having electron-donating groups at the 4 and 7 positions, such as 4,7-di-1-pyrrolidinyl-1,10-phenanthroline (abbreviated as Pyrrd-Phen), can increase the electron density of the nitrogen atoms at the 1 and 10 positions of 1,10-phenanthroline. Therefore, composite materials co-deposited with metals or metal compounds can be suitably used as electron injection layers in light-emitting devices and n-type layers in intermediate layers in tandem light-emitting devices. In particular, the composite materials are preferred because they suppress increases in driving voltage when used in light-emitting devices whose EL layers have been processed by photolithography.

[0059] Conventionally used 1,10-phenanthroline derivatives, particularly those with substituents at the 4 and 7 positions, as described above, are so-called C2-symmetric organic compounds, in which the 1,10-phenanthroline backbone has a symmetric structure and the substituents at the 4 and 7 positions are identical. To introduce substituents into two symmetric carbon atoms of a 1,10-phenanthroline derivative (e.g., the 2 and 9 positions, the 3 and 8 positions, the 4 and 7 positions, and the 5 and 6 positions), the substituents can be introduced by, for example, nucleophilic substitution or Buchwald-Hartwig reaction of a 1,10-phenanthroline derivative substituted with a halogen, triflate, or other group at the corresponding carbon atom. Furthermore, 1,10-phenanthroline derivatives substituted with a halogen, triflate, or other group at the corresponding carbon atom are readily available.

[0060] However, it was difficult to introduce different substituents at the 2,9-, 3,8-, 4,7-, and 5,6-positions using this method because the 2,9-, 3,8-, 4,7-, and 5,6-positions are equivalent in terms of chemical reactivity, and similarly, it was difficult to introduce different substituents at the symmetric positions of 2,2'-bipyridine.

[0061] As mentioned above, when introducing an asymmetric substituent, for example, in the case of 1,10-phenanthroline, it may be possible to synthesize it using the Skraup reaction, but this requires the use of highly hazardous reagents such as concentrated sulfuric acid, and the reaction has poor selectivity, making it an impractical method. Even if synthesis were possible, multiple analogs would be produced simultaneously, making it unclear whether they could be purified, and it cannot be said to be an appropriate method for supplying asymmetric 1,10-phenanthroline derivatives.

[0062] Similarly, 2,2'-bipyridine derivatives can also be synthesized by cross-coupling reactions by preparing two pyridine derivatives with different substituents at the 4-position and a halogen or pinacolboron at the 2-position. However, pyridine compounds with borylated 2-position pyridines are generally known to be unstable and difficult to prepare and store. Furthermore, homocoupling can occur as a side reaction in coupling reactions, resulting in a mixture of at least three reaction products. Therefore, isolating and purifying the desired compound from three compounds with similar properties requires a significant purification process. Additionally, cross-coupling reactions generally require expensive transition metal catalysts, resulting in high costs. While there are several options for transition metal catalysts, including relatively inexpensive transition metal catalysts such as nickel, nickel is not widely used due to its carcinogenicity and the need for safe and hygienic environments in research and production facilities. Furthermore, establishing an environment in which these catalysts can be used is costly. In other words, with the technology that was conceivable before the invention of the technology we have developed, obtaining the above-mentioned asymmetric 1,10-phenanthroline or 2,2'-bipyridine derivatives would have required at least a great deal of time and cost, and moreover, it was not necessarily clear whether the compounds could be synthesized and provided using the technology that had been available up to that point.

[0063] However, the present inventors have found that a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having a symmetric structure in which a halogen or a trifluoromethanesulfonyl group is attached to each of the two symmetric carbon atoms can be reacted with an aliphatic cyclic amine using an inorganic base and a solvent to obtain a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having an asymmetric structure in which an aliphatic cyclic amine is bonded to one of the two symmetric carbon atoms.

[0064] This method can be said to be a technology that can stably synthesize and provide asymmetric 1,10-phenanthroline derivatives or 2,2'-bipyridine derivatives by using symmetrical 1,10-phenanthroline derivatives or 2,2'-bipyridine derivatives that are commercially available at relatively low cost.

[0065] By substituting the remaining halogen or trifluoromethanesulfonyl group of the asymmetric 1,10-phenanthroline derivative or 2,2'-bipyridine derivative obtained by this reaction with an arbitrary substituent, it is possible to obtain a 1,10-phenanthroline derivative or 2,2'-bipyridine derivative having different substituents at symmetric positions.

[0066] In this reaction, the inorganic base may be a salt containing an alkali metal or alkaline earth metal element, or a hydroxide or hydride of the metal element, and potassium carbonate or potassium acetate is preferred because it provides a good yield. As the solvent, a highly polar solvent such as N-methyl-2-pyrrolidone or ethanol may be used, with N-methyl-2-pyrrolidone being particularly preferred because it provides a good yield.

[0067] Furthermore, this reaction can produce a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative in which an aliphatic cyclic amine is bonded to one of the two symmetric carbon atoms in high yield, even when two or more equivalents of an aliphatic cyclic amine are added to the remaining halogen or trifluoromethanesulfonyl group possessed by the 1,10-phenanthroline derivative or the 2,2'-bipyridine derivative. Therefore, even in mass production processes, there is a wide margin for conditions such as the amount of raw materials, reaction temperature, and reaction time, and a stable supply system can be established.

[0068] One of the important factors for selectivity in the reaction to obtain this asymmetric 1,10-phenanthroline derivative or 2,2'-bipyridine derivative is the combination of solvent and base. As will be described in detail below, as disclosed in Non-Patent Document 1, it has been found that using an amine that dissolves in an organic solvent as a base selectively yields a symmetric disubstituted 1,10-phenanthroline derivative. Therefore, if the reaction system remains strongly basic, it becomes difficult to obtain an asymmetric monosubstituted 1,10-phenanthroline.

[0069] On the other hand, in the synthesis method of one embodiment of the present invention, by using an inorganic base such as potassium carbonate, which has low solubility in organic solvents, the basicity in the reaction system can be maintained in the optimal pH range for obtaining an asymmetric monosubstituted 1,10-phenanthroline, which contributes to the selectivity of the reaction. Similarly, since acetate, a salt of a weak acid, also affects the selectivity, polybasic acid salts such as phosphate, which have easy solubility in solvents and pH control, can also be used as the base in the synthesis method of one embodiment of the present invention. The use of such a base makes it possible to selectively obtain an asymmetric 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative.

[0070] By using the above synthesis method, an organic compound represented by the following general formula (G1) can be obtained.

[0071] [ka]

[0072] In the above general formula (G1), X 2 ~X 5 One of the groups is a halogen or a trifluoromethanesulfonyl group, and the rest are hydrogen. 2 ~R 5 represents an aliphatic cyclic amino group represented by the following general formula (g1), and the rest represent hydrogen.

[0073] [ka]

[0074] In the above general formula (g1), R 11 ~R 18 each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18 Any two of these may be bonded to each other to form a ring.

[0075] In the organic compound represented by the general formula (G1), the position of the carbon atom substituted with the halogen or trifluoromethanesulfonyl group is symmetrical to the position of the carbon atom substituted with the group represented by the general formula (g1). 2 is a halogen or trifluoromethanesulfonyl group, R 2 represents an aliphatic cyclic amino group represented by the above general formula (g1). 3 is a halogen or trifluoromethanesulfonyl group, R 3 But X 4 is a halogen or trifluoromethanesulfonyl group, R 4 But X 5 is a halogen or trifluoromethanesulfonyl group, R 5 represents an aliphatic cyclic amino group represented by the above general formula (g1).

[0076] That is, one embodiment of the present invention is an organic compound represented by any one of the following general formulas (G1-1) to (G1-4).

[0077] [ka]

[0078] In the above general formulae (G1-1) to (G1-4), X represents a halogen or a trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the above general formula (g1).

[0079] Similarly, by using the above synthesis method, an organic compound represented by the following general formula (G2) can be obtained.

[0080] [ka]

[0081] In the above general formula (G2), X 6 ~X 9 One of the groups is a halogen or a trifluoromethanesulfonyl group, and the rest are hydrogen. 6 ~R 9 represents an aliphatic cyclic amino group represented by the above general formula (g1), and the rest represent hydrogen.

[0082] In the organic compound represented by the general formula (G2), the position of the carbon atom substituted with the halogen or trifluoromethanesulfonyl group is symmetrical to the position of the carbon atom substituted with the group represented by the general formula (g1). 6 is a halogen or trifluoromethanesulfonyl group, R 6 represents an aliphatic cyclic amino group represented by the above general formula (g1). 7 is a halogen or trifluoromethanesulfonyl group, R 7 But X 8 is a halogen or trifluoromethanesulfonyl group, R 8 But X 9 is a halogen or trifluoromethanesulfonyl group, R 9 represents an aliphatic cyclic amino group represented by the above general formula (g1).

[0083] That is, one embodiment of the present invention is an organic compound represented by any one of the following general formulas (G2-1) to (G2-4).

[0084] [ka]

[0085] In the above general formulae (G2-1) to (G2-4), X represents a halogen or a trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the above general formula (g1).

[0086] The organic compounds represented by the general formula (G1), the general formula (G2), the general formula (G1-1) to the general formula (G1-4), and the general formula (G2-1) to the general formula (G2-4) are 2 ~X 9 or X is a halogen or a trifluoromethanesulfonyl group, various substituents can be introduced into one of the halogen or trifluoromethanesulfonyl groups by performing a nucleophilic substitution reaction using these. An example of an organic compound that can be synthesized using the organic compound of one embodiment of the present invention is an organic compound represented by the following general formula (G3).

[0087] [ka]

[0088] In the general formula (G3), R is a group represented by the following general formula (g1), and A is a group represented by the following general formula (g2) or (g3). In the general formula (G3), the substituent A and the substituent R are different substituents.

[0089] [ka]

[0090] In the above general formula (g1), R 11 ~R 18 each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18 Any two of these may be bonded to each other to form a ring.

[0091] [ka]

[0092] However, in the above general formula (g2), R 21 ~R 28 each independently represents any one of hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and s and t each independently represent 0 to 3. 21 ~R 28Any two of these may be bonded to each other to form a ring. The aliphatic cyclic amino group represented by general formula (g2) may be condensed with an aromatic ring having 6 to 10 carbon atoms. In general formula (g3), Z represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted monovalent heteroaromatic ring group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, or a carbonyl group, and m represents an integer of 1 to 3. When m is 2 or greater, the multiple Zs may be the same or different. Furthermore, L represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, and n represents an integer of 0 to 3. When n is 2 or more, multiple Ls may be the same group or different groups.

[0093] In the organic compound represented by the general formula (G3), it is preferable that A is an organic compound represented by the general formula (g2) because electrons are donated to the 1,10-phenanthroline ring by the resonance effect, thereby improving the electron density of the 1,10-phenanthroline ring moiety. That is, one embodiment of the present invention is an organic compound represented by the following general formula (G3-1).

[0094] [ka]

[0095] In the above general formula (G3-1), R 11 ~R 18 and R 21 ~R 28each independently represents any one of hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p, q, s, and t each independently represent 0 to 3. 11 ~R 18 Any two of, and R 21 ~R 28 Any two of these may be bonded to each other to form a ring. In addition, one of the aliphatic cyclic amino groups in the general formula (G3-1) may be condensed with an aromatic ring having 6 to 10 carbon atoms. In the general formula (G3-1), the substituents bonded to the 4-position and the 7-position of the 1,10-phenanthroline skeleton are different from each other.

[0096] Furthermore, in the organic compound represented by the general formula (G3), when A is an organic compound represented by the general formula (g3), the substituents of 1,10-phenanthroline are different between (g1) and (g3), which facilitates adjustment of parameters such as electron donating property, affinity or exclusivity to solvents including water, and heat resistance. That is, one embodiment of the present invention is preferably an organic compound represented by the following general formula (G3-2).

[0097] [ka]

[0098] In the above general formula (G3-2), R 11 ~R 18each independently represents any one of hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amido group, and a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18 Any two of these may be bonded to each other to form a ring. Furthermore, Z represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted monovalent heteroaromatic ring group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, and m represents an integer of 1 to 3. Note that when m is 2 or greater, multiple Zs may be the same or different groups. Furthermore, L represents a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic ring group having 1 to 25 carbon atoms, and n represents an integer of 0 to 3. When n is 2 or more, the plural Ls may be the same group or different groups.

[0099] As the group represented by the above general formula (g1) or general formula (g2), for example, groups represented by the following structural formulae (Am-1) to (Am-49) are preferred.

[0100] [ka]

[0101] [ka]

[0102] Examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl, heptyl, octyl, 3-methylpentyl, 2-methylpentyl, 2-ethylbutyl, 1,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylhexyl, 1-ethylpropyl, nonyl, 3,7-dimethyl-1-octyl, 3,7-dimethyl-2-octyl, and decyl groups. Among these, tert-butyl and cyclohexyl groups are preferred because they can reduce the refractive index. When the alkyl group having 1 to 10 carbon atoms has a substituent, examples of the substituent include a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 13 carbon atoms, a halogen, or a cyano group.

[0103] Examples of the cycloalkyl group having 3 to 10 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a tricyclo[5.2.1.0(2,6)]decyl group, a noradamantyl group, a 1-methylcyclohexyl group, a bicyclo[2,2,2]octyl group, a norbornyl group, etc. When the cycloalkyl group having 3 to 10 carbon atoms has a substituent, the substituent can be an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 13 carbon atoms, a halogen atom, a cyano group, etc.

[0104] Examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group, an n-pentyloxy group, an isopentyloxy group, a sec-pentyloxy group, a tert-pentyloxy group, a neopentyloxy group, an n-hexyloxy group, an isohexyloxy group, a sec-hexyloxy group, a tert-hexyloxy group, a neohexyloxy group, and a cyclohexyloxy group.

[0105] Examples of monovalent aromatic hydrocarbon groups having 6 to 30 carbon atoms include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, a biphenyl-2-yl group (an o-biphenyl group), a biphenyl-3-yl group (an m-biphenyl group), a biphenyl-4-yl group (an p-biphenyl group), a 1-naphthyl group, a 2-naphthyl group, a phenylnaphthyl group, a naphthylphenyl group, a terphenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a quaterphenyl group, a spirobifluorenyl group, a phenanthryl group, an anthryl group, a binaphthylphenyl group, a fluoranthenyl group, a triphenylenyl group, etc. When an aryl group having 6 to 30 carbon atoms has a substituent, the substituent can be an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 13 carbon atoms, a halogen, a cyano group, etc.

[0106] Specific examples of the heteroaryl group having 1 to 30 carbon atoms include a 1,3,5-triazin-2-yl group, a 1,2,4-triazin-3-yl group, a pyrimidin-4-yl group, a pyrazin-2-yl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, an indenocarbazolyl group, a dibenzocarbazolyl group, an indolyl group, a pyrrolyl group, a 1,2,3-triazolyl group, and a 1,2,4-triazolyl group. When the heteroaryl group having 1 to 30 carbon atoms has a substituent, examples of the substituent include an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 13 carbon atoms, a halogen atom, or a cyano group.

[0107] Examples of alkylene groups having 1 to 3 carbon atoms include methylene, ethylene, and propylene groups. Examples of cycloalkylene groups having 3 to 10 carbon atoms include divalent groups obtained by removing one hydrogen atom from the above-mentioned cycloalkyl groups having 3 to 10 carbon atoms.

[0108] Examples of the divalent heterocyclic group having 1 to 25 carbon atoms include a pyrimidine-diyl group, a pyrazine-diyl group, a pyridazine-diyl group, a triazine-diyl group, a bipyridine-diyl group, a phenanthroline-diyl group, a quinoxaline-diyl group, a dibenzoquinoxaline-diyl group, a quinazoline-diyl group, a benzoquinazoline-diyl group, a dibenzoquinazoline-diyl group, an imidazole-diyl group, a triazole-diyl group, an oxadiazole-diyl group, a benzimidazole-diyl group, a furodiazine-diyl group, a benzofuropyrimidine-diyl group, a thiophene-diyl group, and a furan-diyl group. Examples of the heterocyclic group include a benzothiophene-diyl group, a benzofuran-diyl group, a dibenzothiophene-diyl group, a dibenzofuran-diyl group, a benzonaphthothiophene-diyl group, a benzonaphthofuran-diyl group, a dinaphthothiophene-diyl group, a dinaphthofuran-diyl group, a piperazine-diyl group, a hexahydropyrimidine-diyl group, a hexahydrotriazine-diyl group, a decahydroquinoxaline-diyl group, a decahydronaphthyridine-diyl group, an imidazolidine-diyl group, an octahydropyrrolopyridine-diyl group, and an octahydropyrrolopyrrole-diyl group. When the divalent heterocyclic group having 1 to 25 carbon atoms has a substituent, examples of the substituent include an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

[0109] Examples of divalent aromatic hydrocarbon groups having 6 to 25 carbon atoms include phenylene, biphenyl-diyl, naphthalene-diyl, fluorene-diyl, acenaphthene-diyl, anthracene-diyl, phenanthrene-diyl, terphenyl-diyl, triphenylene-diyl, tetracene-diyl, benzanthracene-diyl, pyrene-diyl, and spirobi[9H-fluorene]-diyl groups. When an arylene group having 6 to 30 carbon atoms has a substituent, examples of the substituent include an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and an aryl group having 6 to 13 carbon atoms.

[0110] The organic compound represented by General Formula (G3) preferably has one or two alkyl groups, since this does not interfere with the electron-transporting property. The presence of alkyl groups can reduce the refractive index of a film made of the organic compound, and the greater the number of alkyl groups, the lower the refractive index of the evaporated film and the higher the luminous efficiency of the light-emitting device. On the other hand, it is also known that alkyl groups tend to reduce the electron-transporting property. The organic compound of one embodiment of the present invention can be used to form a film with a low refractive index even if the organic compound has only a small number of hydrocarbon groups, thereby achieving both electron-transporting property and a low refractive index of the film.

[0111] Furthermore, when the organic compound represented by general formula (G3) is an organic compound having an alkyl group, it is preferable that at least one alkyl group is bonded to a phenyl group. That is, it is preferable that the organic compound represented by general formula (G3) has a phenyl group having an alkyl group. Furthermore, when the phenyl group has two alkyl groups, it is preferable that the two alkyl groups are substituted at the 3- and 5-positions of the terminal phenyl group, in order to facilitate the availability of synthetic raw materials. Note that, as the phenyl group having an alkyl group, a 4-cyclohexylphenyl group, a 3',5'-ditertiarybutylbiphenyl group, a 3',5'-dicyclohexylbiphenyl group, etc. are particularly preferable.

[0112] The secondary amino group having 2 to 10 carbon atoms is preferably a cyclic secondary amine, such as a pyrrolidin-1-yl group, an isoindole-2-yl group, a dihydroisoindol-2-yl group, a tetrahydroisoindol-2-yl group, a hexahydroisoindol-2-yl group, a hexahydroisoindolin-2-yl group, a piperidin-1-yl group, an aziridin-1-yl group, an azetidin-1-yl group, an octahydrocyclopenta[c]pyrrol-2-yl group, an octahydro-4,7-methano-1H-isoindol-2-yl group, a 2-azabicyclo[3.1.0]pyrrol ... ]hexan-2-yl group, 3-azabicyclo[3.1.0]hexan-2-yl group, 3-azabicyclo[3.2.0]heptan-2-yl group, 5-azaspiro[3.4]octan-5-yl group, 8-azabicyclo[3.2.1]octan-8-yl group, 7-azabicyclo[2.2.1]heptan-7-yl group, 5-azaspiro[2.4]heptan-5-yl group, 5-azabicyclo[2.1.1]hexan-5-yl group, dimethylamino group, diethylamino group, diisopropylamino group, diphenylamino group, dicyclohexylamino group, etc. When the cyclic secondary amino group having 2 to 10 carbon atoms has a substituent, the substituent can be an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

[0113] Examples of the organic compounds represented by the general formula (G1) and the general formula (G2) include organic compounds represented by the following structural formulas (200) to (275).

[0114] [ka]

[0115] [ka]

[0116] [ka]

[0117] [ka]

[0118] In addition, examples of the organic compound represented by the general formula (G3) that can be synthesized using the organic compound represented by the general formula (G1) include organic compounds represented by the following structural formulas (100) to (135).

[0119] [ka]

[0120] [ka]

[0121] [ka]

[0122] The synthesis methods of the organic compounds represented by General Formulas (G1) to (G3), which are organic compounds according to embodiments of the present invention, will be described in detail below.

[0123] First, a method for synthesizing the organic compounds represented by the general formula (G1) and the general formula (G2), which are organic compounds according to one embodiment of the present invention, will be described using the synthesis of an organic compound represented by the following general formula (G1-3-1) as an example. Note that the following general formula (G1-3-1) is a general formula in which R in the general formula (G1-3) is replaced with (g1). Note that X and R in the general formula (G1-3-1) 11 ~R 18 , p and q are the same as in (G1-3), so repeated descriptions will be omitted.

[0124] [ka]

[0125] The organic compound represented by general formula (G1-3-1) can be synthesized by a simple synthesis scheme such as the following synthesis scheme (A-1).

[0126] [ka]

[0127] In the above compound (a1), X represents a halogen or a trifluoromethanesulfonyl group.

[0128] In the above compound (a2), R 11 ~R 18 , p and q are the same as in general formula (g1).

[0129] In the synthesis scheme (A-1), a phenanthroline intermediate having an aliphatic cyclic amino group represented by general formula (G1-3) can be obtained by subjecting a phenanthroline derivative (a1) and an aliphatic cyclic amine derivative (a2) to a nucleophilic substitution reaction using an appropriate solvent and an inorganic base.

[0130] Examples of inorganic bases that can be used in the nucleophilic substitution reaction represented by the above synthesis scheme (A-1) include carbonates such as potassium carbonate, cesium carbonate, sodium carbonate, and potassium hydrogencarbonate, acetates such as potassium acetate and sodium acetate, and phosphates such as tripotassium phosphate and trisodium phosphate. Potassium carbonate and potassium acetate, and particularly potassium carbonate, are preferred because they provide good yields.

[0131] Examples of solvents that can be used in the nucleophilic substitution reaction represented by the above synthesis scheme (A-1) include N-methyl-2-pyrrolidone, N,N-dimethylformamide, tetrahydrofuran, dioxane, ethanol, ethyl acetate, toluene, etc. However, the solvents that can be used are not limited to these.

[0132] Although the synthesis method of the organic compound represented by general formula (G1-3-1) has been described above, the compounds represented by general formulas (G1-1), (G1-2), (G1-4), and general formulas (G2-1) to (G2-4) can also be synthesized by changing the phenanthroline derivative (a1) to the corresponding raw material.

[0133] Next, a method for synthesizing an organic compound represented by general formula (G3) will be described using an organic compound represented by general formula (3-1) as an example.

[0134] In the organic compound represented by the above general formula (G3), an organic compound represented by general formula (G3-1) in which the substituent of A is a group represented by the above general formula (g2) can be synthesized by a simple synthesis scheme such as the above synthesis scheme (A-1) or the following synthesis scheme (A-2).

[0135] [ka]

[0136] In the above compound (a3), R 21 ~R 28 , s, and t are the same as in general formula (g2). Note that a compound different from the compound used in (a2) is used.

[0137] In the synthesis scheme (A-2), an organic compound represented by the general formula (G3-1) can be obtained by subjecting a phenanthroline intermediate having an aliphatic cyclic amino group represented by the general formula (G1-3) to a nucleophilic substitution reaction with an aliphatic cyclic amine derivative (a3) ​​using an appropriate solvent and a base.

[0138] Examples of the base that can be used in the nucleophilic substitution reaction represented by the above synthesis scheme (A-2) include organic bases such as diazabicycloundecene (DBU), triethylamine, and potassium tert-butoxide, and inorganic bases such as potassium carbonate, cesium carbonate, sodium carbonate, sodium hydrogencarbonate, potassium acetate, sodium acetate, tripotassium phosphate, and trisodium phosphate.

[0139] Examples of solvents that can be used in the nucleophilic substitution reaction represented by the above synthesis scheme (A-2) include N-methyl-2-pyrrolidone, N,N-dimethylformamide, toluene, tetrahydrofuran, dioxane, and ethanol. However, the solvents that can be used are not limited to these. When an organic base is used, it may be used as both a base and a solvent.

[0140] Furthermore, the reaction carried out in the above synthesis scheme (A-2) is not limited to a nucleophilic substitution reaction, and a Buchwald-Hartwig reaction, a coupling reaction using copper or a copper compound, or the like can also be used.

[0141] In the organic compound represented by the above general formula (G3), an organic compound represented by general formula (G3-2) in which the substituent of A is a group represented by the above general formula (g3) can be synthesized by a simple synthesis scheme such as the above synthesis scheme (A-1) or the following synthesis scheme (A-3).

[0142] [ka]

[0143] In the above compound (a4), Q represents a boronyl group (-B(OH)2), and Z, L, n, and m are the same as in general formula (g3). When Q represents a boronyl group in compound (a4), a boronate ester or a cyclic triol borate salt may be used. However, Q is not necessarily limited to a boronyl group. It may also be a nucleophile that can generally perform a wide range of coupling reactions, such as magnesium or zinc. From the viewpoints of environmental impact and ease of procurement of raw materials, a boronyl group is preferred.

[0144] Examples of palladium catalysts that can be used in the coupling reaction represented by the synthetic scheme (A-3) include palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palladium(II) dichloride, etc. Examples of the ligand for the palladium catalyst include di(1-adamantyl)-n-butylphosphine, (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, tri(ortho-tolyl)phosphine, triphenylphosphine, tricyclohexylphosphine, etc.

[0145] Examples of the base that can be used in the coupling reaction represented by the above synthesis scheme (A-3) include organic bases such as potassium tert-butoxide, and inorganic bases such as cesium carbonate, potassium carbonate, sodium carbonate, and tripotassium phosphate.

[0146] Solvents that can be used in the coupling reaction represented by the above synthesis scheme include 1,2-dimethoxyethane, toluene, xylene, mesitylene, benzene, tetrahydrofuran, dioxane, etc. However, the solvents that can be used are not limited to these.

[0147] The reaction performed in the above synthesis scheme (A-3) is not limited to the Suzuki-Miyaura reaction, but may also be a Migita-Kosugi-Still coupling reaction using an organotin compound, a coupling reaction using a Grignard reagent, a Negishi reaction, a coupling reaction using copper or a copper compound, a nucleophilic substitution reaction, or the like.

[0148] Furthermore, various types of the above-mentioned compounds (a1), (a2), (a3) ​​and (a4) are commercially available or can be synthesized.

[0149] Although the organic compound of one embodiment of the present invention can be synthesized as described above, the present invention is not limited thereto, and the compound may be synthesized by other synthesis methods.

[0150] This embodiment mode can be used in any combination with other embodiment modes and examples.

[0151] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate.

[0152] (Embodiment 2) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described in detail.

[0153] 1 is a schematic diagram of a light-emitting device according to one embodiment of the present invention. The light-emitting device includes a first electrode 101 provided over an insulator 100, and an organic compound layer 103 between the first electrode 101 and a second electrode 102. The organic compound layer 103 includes at least one of the organic compounds represented by the general formula (G3) in Embodiment 1. The light-emitting layer 113 in the light-emitting device includes a luminescent center substance, and the luminescent center substance emits light when a voltage is applied between the first electrode 101 and the second electrode 102.

[0154] 1(A), the organic compound layer 103 preferably includes functional layers such as a hole injection layer 111, a hole transport layer 112, an electron transport layer 114, and an electron injection layer 115 in addition to the light-emitting layer 113. The organic compound layer 103 may also include functional layers other than those described above, such as a hole blocking layer, an electron blocking layer, an exciton blocking layer, and a charge generating layer. Conversely, any of the layers described above may not be provided.

[0155] In addition, the organic compound represented by general formula (G3) in Embodiment 1 is preferably contained in a layer that uses electrons as carriers because it exhibits high electron transporting and electron injecting properties. Examples of layers that use electrons as carriers include an electron injecting layer, an electron transporting layer, a hole blocking layer, a light-emitting layer, and an intermediate layer, and the organic compound represented by general formula (G3) is particularly preferably used in the electron injecting layer and the intermediate layer.

[0156] In this embodiment, the first electrode 101 is described as an electrode including an anode, and the second electrode 102 is described as an electrode including a cathode, but this may be reversed. The first electrode 101 and the second electrode 102 are formed as a single-layer structure or a stacked-layer structure. In the case of a stacked-layer structure, the layer in contact with the organic compound layer 103 functions as an anode or a cathode. In the case of a stacked-layer structure, there is no restriction on the work function of layers other than the layer in contact with the organic compound layer 103, and materials may be selected depending on required characteristics such as resistance, ease of processing, reflectance, light transmittance, and stability.

[0157] The anode is preferably formed using a metal, alloy, conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or higher). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide (ITSO), indium oxide-zinc oxide, and indium oxide containing tungsten oxide and zinc oxide (IWZO). These conductive metal oxide films are usually formed by sputtering, but they may also be prepared by applying a sol-gel method. For example, indium oxide-zinc oxide can be formed by sputtering using a target in which 1 to 20 wt % of zinc oxide is added to indium oxide. Indium oxide containing tungsten oxide and zinc oxide (IWZO) can also be formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide. Other materials that can be used for the anode include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), aluminum (Al), and nitrides of metal materials (e.g., titanium nitride). A layer formed by stacking these materials can also be used as the anode. For example, a film formed by stacking Al, Ti, and ITSO on Ti in this order is preferred because of its high reflectivity, high efficiency, and the ability to achieve high resolution of several thousand ppi. Graphene can also be used as the anode material. In addition, by using a composite material capable of forming the hole injection layer 111 described later as a layer in contact with the anode (typically the hole injection layer), it becomes possible to select an electrode material regardless of the work function.

[0158] The hole injection layer 111 is provided in contact with the anode and has the function of facilitating the injection of holes into the organic compound layer 103. The hole injection layer 111 can be formed of a phthalocyanine compound such as phthalocyanine (abbreviation: HPc) or copper phthalocyanine (abbreviation: CuPc), a phthalocyanine complex compound, an aromatic amine compound such as 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB) or 4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), or a polymer compound such as poly(3,4-ethylenedioxythiophene) / (polystyrenesulfonic acid) (abbreviation: PEDOT / PSS).

[0159] Alternatively, the hole injection layer 111 may be formed of a substance having electron acceptor properties. Examples of the substance having acceptor properties include organic compounds having an electron-withdrawing group (such as a halogen group or a cyano group), such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), and 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile. In particular, compounds in which an electron-withdrawing group is bonded to a fused aromatic ring having multiple heteroatoms, such as HAT-CN, are preferred because of their thermal stability. Radialene derivatives having electron-withdrawing groups (especially halogen groups such as fluoro groups, cyano groups, etc.) are also preferred because of their extremely high electron-accepting properties. Specific examples include α,α',α''-1,2,3-cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenetris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropanetriylidenetris[2,3,4,5,6-pentafluorobenzeneacetonitrile]. As the substance having acceptor properties, in addition to the organic compounds described above, transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide can be used.

[0160] The hole-injection layer 111 is preferably formed using a composite material containing the above-mentioned material having an acceptor property and an organic compound having a hole-transport property.

[0161] As the organic compound having hole transport properties used in the composite material, various organic compounds can be used, such as aromatic amine compounds, heteroaromatic compounds, aromatic hydrocarbons, and polymer compounds (oligomers, dendrimers, polymers, etc.). Note that the organic compound having hole transport properties used in the composite material can be 1×10 -6 cm 2 Preferably, the organic compound has a hole mobility of 1 / Vs or more. The organic compound having hole transport properties used in the composite material is preferably a compound having a fused aromatic hydrocarbon ring or a π-electron-rich heteroaromatic ring. As the fused aromatic hydrocarbon ring, an anthracene ring, a naphthalene ring, or the like is preferred. Furthermore, as the π-electron-rich heteroaromatic ring, a fused aromatic ring containing at least one of a pyrrole skeleton, a furan skeleton, and a thiophene skeleton is preferred, and specifically, a carbazole ring, a dibenzothiophene ring, or a ring in which an aromatic ring or a heteroaromatic ring is further fused to the above ring is preferred.

[0162] Such organic compounds having hole-transporting properties preferably have at least one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, aromatic amines having a substituent containing a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group may be used. It is preferable that these organic compounds having hole-transporting properties are substances having an N,N-bis(4-biphenyl)amino group, since this allows the fabrication of light-emitting devices with long lifetimes.

[0163] Specific examples of organic compounds having hole transport properties as described above include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-yl, and N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-yl. 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-biphen nilamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-([2,1'-binaphthyl]-6-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-([2,1'-binaphthyl]-7-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-diphenyl -4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-([2,2'-binaphthyl]-6-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-([2,2'-binaphthyl]-7-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-([1,2'-binaphthyl]-4-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4''-([1,2'-binaphthyl]-5-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''-phenyl Triphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tris (Biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis( Biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4' -[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'- Di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluoren]-2-amine (abbreviation: PCBASF), N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), N,N-bis( Examples of such amines include N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-2-amine, and N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-1-amine.

[0164] Other aromatic amine compounds that can be used as materials having hole transport properties include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B).

[0165] By forming the hole injection layer 111, the hole injection property becomes good, and a light emitting device with a low driving voltage can be obtained.

[0166] Among substances having acceptor properties, organic compounds having acceptor properties are easy to use because they can be easily vapor-deposited and formed into a film.

[0167] The hole transport layer 112 is formed by containing an organic compound having a hole transport property. -6 cm 2 It is preferable that the hole mobility is / Vs or more.

[0168] Examples of the material having hole transport properties include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3-methylphenyl-4,4'-diaminobiphenyl (abbreviation: 4,4'-bis(9H-fluoren-2-yl)triphenylamine) ... '-(9-Phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl) Compounds with an aromatic amine skeleton, such as 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di( N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviation: BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,3'-Bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: βNCCP), 9-(3-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCmBP), 9-(4-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCBP), 9,9'-di-2-naphthyl-3,3'-9H,9'H-bicarbazole (abbreviation: BisβNCz), 9-(2-naphthyl)-9'-[1,1':4',1"-terf phenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-5'-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':4',1"-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1"-terphenyl]-4-yl-3,3 '-9H,9'H-Bicarbazole, 9-(2-naphthyl)-9'-(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole, 9-phenyl-9'-(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole (abbreviation: PCCzTp), 9,9'-bis(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(4-biphenyl)-9'-(triphenylen-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(triphenylen-2-yl)-9'-[1,1':3',1"-taphe compounds having a carbazole skeleton such as [4-yl-3,3'-9H,9'H-bicarbazole]; compounds having a thiophene skeleton such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV);Examples of the compounds include compounds having a furan skeleton, such as 4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among the compounds mentioned above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are 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.

[0169] The luminescent center substance may be a fluorescent substance, a phosphorescent substance, a substance exhibiting thermally activated delayed fluorescence (TADF), or any other luminescent substance.

[0170] Examples of materials that can be used as fluorescent materials in the light-emitting layer include the following: In addition, fluorescent materials other than these can also be used.

[0171] 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-( 10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis(N,N',N'-triphenyl-1,4-phenylenediamine) (abbreviation: DPABPA), N,9 -diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviated as 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPPA), N,N,N',N',N'',N'',N''',N'''-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviated as DBC1), Coumarin 30, N-(9,10-diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA) , 9,10-bis(biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyra N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhTD), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhTD), Name: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB),6-Bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), N,N'-diphenyl-N,N'-(1,6-pyren-diyl)bis[(6-phenylbenzo[b]naphtho]] Examples include N,N'-diphenyl-N,N'-bis(9-phenyl-9H-carbazol-2-yl)naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviated as 3,10PCA2Nbf(IV)-02), and 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10FrA2Nbf(IV)-02). In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred due to their high hole-trapping properties and excellent luminous efficiency and reliability.

[0172] In addition, 5,9-diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: DABNA-1), 9-(diphenyl-3-yl)-N,N,5,11-tetraphenyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracen-3-amine (abbreviation: DABNA-2), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-N,N-diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: DABNA-3), Phosphorus-7-amine (abbreviation: DPhA-tBu4DABNA), 2,12-di(tert-butyl)-N,N,5,9-tetra(4-tert-butylphenyl)-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin-7-amine (abbreviation: tBuDPhA-tBu4DABNA), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-7-methyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin (abbreviation: Me-tBu4DABNA), N 7 ,N 7 ,N 13 ,N 13 Fused heteroaromatic compounds containing nitrogen and boron, such as 5,9,11,15-octaphenyl-5H,9H,11H,15H-[1,4]benzazaborino[2,3,4-kl][1,4]benzazaborino[4',3',2':4,5][1,4]benzazaborino[3,2-b]phenazaborine-7,13-diamine (abbreviation: ν-DABNA) and 2-(4-tert-butylphenyl)benz[5,6]indolo[3,2,1-jk]benzo[b]carbazole (abbreviation: tBuPBibc), are particularly suitable for use as compounds having a diazaboranaphthoanthracene skeleton, since they have a narrow emission spectrum and can emit blue light with good color purity.

[0173] In addition to these, 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: BBCz-G), 9,11-bis[3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: BBCz-Y) and the like can be preferably used.

[0174] When a phosphorescent material is used as the light-emitting material in the light-emitting layer, the phosphorescent material is preferably a metal complex, particularly an iridium complex or a platinum complex, and examples thereof include the following materials.

[0175] Organometallic iridium complexes with a 4H-triazole skeleton, such as tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]) and tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]). , organometallic iridium complexes with a 1H-triazole skeleton, such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), fac-tris[1-(2,6-di [Ir(iPrpim)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), tris(2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazol-2-yl-κN3}-4-cyano organometallic iridium complexes with an imidazole skeleton, such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC2)phenyl-κC]iridium(III) (abbreviation: CNImIr), organometallic complexes with a benzimidazolidene skeleton, such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC2)phenyl-κC]iridium(III) (abbreviation: [Ir(cb)3]), and organometallic complexes with a benzimidazolidene skeleton, such as bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ] Organometallic iridium complexes with phenylpyridine derivatives containing electron-withdrawing groups as ligands, such as iridium(III) acetylacetonate (abbreviated as FIracac), are compounds that exhibit blue phosphorescence and have an emission peak in the wavelength range from 450 nm to 520 nm.

[0176] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6- Organometallic iridium complexes with a pyrimidine skeleton, such as (2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]) and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and tris(2-phenylpyridinato-N,C 2’) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C 2’) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mbfpypy-d3)]), {2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofuro[2,3-b]pyridin-7-yl-κC}bis{5-(methyl-d3 )-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviated as Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-(methyl-d3)-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviated as [Ir(ppy)2(mbfpypy-d3)]), [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl [Ir(ppy)2(mdppy)]), [2-(4-d3-methyl-5-phenyl-2-pyridinyl-κN2)phenyl-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mdppy-d3)]), [2-methyl-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2( In addition to organometallic iridium complexes with a pyridine skeleton, such as (2-{1-(5-tert-butylbiphenyl-2-yl)-4-[3-tert-butyl-5-(4-phenyl-2-pyridinyl-κN)phenyl-κC6]-2-benzimidazolyl-κN3}-4,6-di-tert-butylphenolato-κO)platinum(II) (abbreviated as Pt(tBudppymmtBubiz-tBubp)), [2-(4-(3,5-di-tert-butylphenyl)-6-{3-[4-(5'-tert-butyl[1,1':3',Examples include organometallic platinum complexes such as [(1'-terphenyl)-2'-yl)-2-pyridinyl-κN]phenyl-κC2}-2-pyridinyl-κN)phenolato-κO]platinum(II) (abbreviation: Pt(4tButpppypyp-mmtBup)), and rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]). These compounds primarily exhibit green phosphorescence, with an emission peak in the wavelength range of 500 nm to 600 nm. Organometallic iridium complexes with a pyrimidine skeleton are particularly preferred because of their outstanding reliability and luminous efficiency.

[0177] and organometallic iridium complexes having a pyrimidine skeleton, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), and bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]). Organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’) iridium(III) acetylacetonate (abbreviated as [Ir(piq)2(acac)]), (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolinyl-κN]phenyl-κC]iridium(III), and (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolinyl-κN]phenyl-κC]iridium(III). In addition to iridium complexes, platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP) and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviated as [Eu(DBM)3(Phen)]) and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviated as [Eu(TTA)3(Phen)]) are compounds that exhibit red phosphorescence, with peak emission in the wavelength range from 600 to 700 nm. Organometallic iridium complexes with a pyrazine skeleton also exhibit excellent red chromaticity.

[0178] In addition to the phosphorescent compounds described above, known phosphorescent compounds may be selected and used.

[0179] 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.

[0180] [ka]

[0181] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), and Heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, such as 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA), can also be used. The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, and therefore has high electron transport and hole transport properties, and is therefore preferred. Among the skeletons having a π-electron-deficient heteroaromatic ring, pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferred because they are stable and reliable. In particular, benzofuropyrimidine skeleton, benzothienopyrimidine skeleton, benzofuropyrazine skeleton, and benzothienopyrazine skeleton are preferred because they have high acceptor properties and good reliability. Furthermore, among the skeletons having a π-electron-rich heteroaromatic ring, acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are preferred because they are stable and reliable.The furan skeleton is preferably a dibenzofuran skeleton, and the thiophene skeleton is preferably a dibenzothiophene skeleton. The pyrrole skeleton is particularly preferably an indole skeleton, a carbazole skeleton, an indolocarbazole skeleton, a bicarbazole skeleton, or a 3-(9-phenyl-9H-carbazol-3-yl)-9H-carbazole skeleton. Substances in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded are particularly preferred because the electron-donating ability of the π-electron-rich heteroaromatic ring and the electron-accepting ability of the π-electron-deficient heteroaromatic ring are both enhanced, thereby reducing the energy difference between the S1 level and the T1 level, thereby enabling efficient thermally activated delayed fluorescence. Instead of the π-electron-deficient heteroaromatic ring, an aromatic ring bonded to an electron-withdrawing group such as a cyano group may be used. The π-electron-rich skeleton may be, for example, an aromatic amine skeleton or a phenazine skeleton. Examples of usable π-electron-deficient skeletons include a xanthene skeleton, a thioxanthene dioxide skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or boranthrene, an aromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a heteroaromatic ring, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, etc. In this way, a π-electron-deficient skeleton and a π-electron-rich skeleton can be used in place of at least one of a π-electron-deficient heteroaromatic ring and a π-electron-rich heteroaromatic ring.

[0182] [ka]

[0183] 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.

[0184] 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.

[0185] Note that the T1 level can be measured using a phosphorescence spectrum observed at low temperatures (for example, 77 K to 10 K). For a TADF material, when a tangent line is drawn at the base of the fluorescence spectrum on the short wavelength side and the energy of the wavelength of the extrapolated line is taken as the S1 level, and a tangent line is drawn at the base of the phosphorescence spectrum on the short wavelength side and the energy of the wavelength of the extrapolated line is taken as the T1 level, the difference between S1 and T1 is preferably 0.3 eV or less, and more preferably 0.2 eV or less.

[0186] 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.

[0187] As the host material of the light-emitting layer, various carrier transport materials such as a material having an electron transport property and / or a material having a hole transport property, and the above-mentioned TADF material can be used.

[0188] Preferred materials having hole transport properties include organic compounds having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton. The π-electron-rich heteroaromatic ring is preferably a fused aromatic ring containing at least one of an acridine skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a furan skeleton, a thiophene skeleton, and a pyrrole skeleton, and more specifically, a carbazole ring, a dibenzothiophene ring, or a ring in which an aromatic ring or a heteroaromatic ring is further fused to the carbazole ring, a dibenzothiophene ring, or the like.

[0189] Such organic compounds having hole-transporting properties preferably have at least one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, aromatic amines having a substituent containing a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group may be used. It is preferable that these organic compounds having hole-transporting properties are substances having an N,N-bis(4-biphenyl)amino group, since this allows the fabrication of light-emitting devices with long lifetimes.

[0190] Examples of such organic compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: :BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1BP), Aromatic compounds such as PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviated as PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviated as PCBASF) Compounds with an aromatic amine skeleton, compounds with a carbazole skeleton such as 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), and 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,Examples of suitable materials include compounds having a thiophene skeleton, such as 8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), and compounds having a furan skeleton, such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among the above, compounds having an aromatic amine skeleton or a carbazole skeleton are preferred because they have good reliability, high hole transport properties, and contribute to reducing driving voltage. The organic compounds listed as examples of materials having hole transport properties for the hole transport layer can also be used.

[0191] Materials with electron transport properties have an electron mobility of 1×10 at a square root of the electric field strength [V / cm] of 600. -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2 A substance having an electron mobility of 1 / Vs or more is preferred. Note that other substances can also be used as long as they have a higher electron transporting property than holes.

[0192] Preferred examples of the material having electron transport properties include metal complexes such as bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and organic compounds having a π-electron-deficient heteroaromatic ring. Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include organic compounds containing a heteroaromatic ring having an azole skeleton, organic compounds containing a heteroaromatic ring having a pyridine skeleton, organic compounds containing a heteroaromatic ring having a diazine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton.

[0193] Among these, organic compounds containing a heteroaromatic ring having a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), organic compounds containing a heteroaromatic ring having a pyridine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton are preferred because of their high reliability. In particular, organic compounds containing a heteroaromatic ring having a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing a heteroaromatic ring having a triazine skeleton have high electron transport properties and contribute to reduced driving voltage. In addition, benzofuropyrimidine skeletons, benzothienopyrimidine skeletons, benzofuropyrazine skeletons, and benzothienopyrazine skeletons are preferred because of their high acceptor properties and high reliability.

[0194] Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole- Organic compounds with an azole skeleton, such as 2-[3-(dibenzothiophen-4-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), 3,5-bis[3-(9H-carbazole-9-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), (phenyl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P), 2-[3-(2-triphenylenyl)phenyl]-1, Organic compounds containing heteroaromatic rings with a pyridine skeleton, such as 1,10-phenanthroline (abbreviated as mTpPPhen), 2-phenyl-9-(2-triphenylenyl)-1,10-phenanthroline (abbreviated as Ph-TpPhen), 2-[4-(9-phenanthryl)-1-naphthyl]-1,10-phenanthroline (abbreviated as PnNPhen), and 2-[4-(2-triphenylenyl)phenyl]-1,10-phenanthroline (abbreviated as pTpPPhen), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 2-[4-(3,6-diphenyl phenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 6mDBTPDBq-II), 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as 9mDBtBPNf pr), 9-[3'-(dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as 9pmDBtBPNfpr), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviated as 4,6mPnP2Pm), 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviated as 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviated as 4,6mCzP2Pm), 9,9'-[pyrimidinyl benzofuro[3,2-d]pyrimidine (abbreviated as 8BP-4mDBtPBfpm), 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3-b]pyrazine (abbreviated as 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), 8-([2,2'-binaphthalen]-6-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm), 8-(p-terphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]- [1] Benzofuro[3,2-d]pyrimidine (abbreviation: 8mpTP-4mDBtPBfpm), 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2,2'-([2,2'-bipyridine]-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 6,6'(P-Bqn)2BPy), 2,2'-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm)2Py), 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 2,6-bis(4-naphthalen-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 7-[4-(9-phenyl-9H-carbazol-2-yl)ki Organic compounds with diazine skeletons such as 11-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazine (abbreviation: 11mDBtBPPnfpr), 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluoren]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn ), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviated as mPCCzPTzn-02), 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviated as mFBPTzn), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole ( abbreviation: mINc(II)PTzn), 2-{3-[3-(dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mDBtBPTzn), 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: TmPPPyTz), 2,4,6-tris(2-pyridyl)-1,3,5-triazine (abbreviation: 2Py3Tzn), 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthryl)phenyl]phenyl]-4,6-diphenyl-1,3,5-triazine nyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazin-2-yl]-11,12-dihydro-12-phenyl-indolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), 2-[3'-(triphenylen-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 3-[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-(biphenyl-3-yl)-4-phenyl-6-[8-([1,1':4',1''-terphenyl]-4-yl)-1-dibenzofuranyl]-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 2-[4-(2-naphthyl)phenyl]-4-phenyl-6-spiro[9H-fluorene-9,9'-[9H]oxazole] Examples of suitable organic compounds include organic compounds containing a heteroaromatic ring with a triazine skeleton, such as [3-(triphenylsilyl)phenyl]-4-yl-1,3,5-triazine (abbreviated as βNP-SFx(4)Tzn), 2-phenyl-4,6-bis[3-(triphenylsilyl)phenyl]-1,3,5-triazine (abbreviated as mSiTrz), and 9,9'-{6-[3-(triphenylsilyl)phenyl]-1,3,5-triazine-2,4-diyl}bis(9H-carbazole) (abbreviated as SiTrzCz2). Organic compounds containing a heteroaromatic ring with a diazine skeleton, organic compounds containing a heteroaromatic ring with a pyridine skeleton, and organic compounds containing a heteroaromatic ring with a triazine skeleton are preferred due to their high reliability. In particular, organic compounds containing a heteroaromatic ring with a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing a heteroaromatic ring with a triazine skeleton have high electron transport properties and contribute to reduced driving voltage.

[0195] In addition, in Embodiment 1, the organic compound represented by the general formula (G3) is also an organic compound having a pyridine skeleton and a π-electron-deficient heteroaromatic ring skeleton, and therefore can be suitably used as a material having an electron-transport property.

[0196] 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.

[0197] 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.

[0198] 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.

[0199] Furthermore, to efficiently generate singlet excitation energy from triplet excitation energy through reverse intersystem crossing, carrier recombination is preferred in the TADF material. Furthermore, it is preferable that the triplet excitation energy generated in the TADF material does not transfer to triplet excitation energy in the fluorescent material. To achieve this, the fluorescent material preferably has a protecting group around the luminophore (the skeleton responsible for light emission) of the fluorescent material. The protecting group is preferably a substituent without a π bond, and is preferably a saturated hydrocarbon. Specific examples include alkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, and trialkylsilyl groups with 3 to 10 carbon atoms. Multiple protecting groups are even more preferred. Substituents without a π bond have poor carrier transport properties, allowing for increased distance between the TADF material and the luminophore of the fluorescent material without significantly affecting carrier transport or carrier recombination. Here, the term "luminophore" refers to the atomic group (skeleton) responsible for light emission in the fluorescent material. The luminophore preferably has a skeleton having a π bond, preferably contains an aromatic ring, and preferably has a fused aromatic ring or a fused heteroaromatic ring. Examples of such luminophores include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, and a naphthobisbenzofuran skeleton. In particular, fluorescent materials having a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, or a naphthobisbenzofuran skeleton are preferred because of their high fluorescence quantum yield.

[0200] When a fluorescent emitting substance is used as the emitting substance, a material having an acene skeleton, particularly an anthracene skeleton, is suitable as the host material. Using a substance having an anthracene skeleton as a host material for a fluorescent emitting substance enables the realization of an emitting layer with both excellent luminous efficiency and durability. As a 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 fused to the carbazole skeleton, are even more preferred because their HOMO level is approximately 0.1 eV higher than that of host materials having a carbazole skeleton, making them more likely to introduce holes. In particular, host materials containing a dibenzocarbazole skeleton are preferred because their HOMO level is approximately 0.1 eV higher than that of host materials having a carbazole skeleton, making them more likely to introduce holes, as well as providing 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. Furthermore, a dibenzofuran skeleton is preferable because it can ensure reliability without lowering the T1 level.

[0201] Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4' -yl]anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracen-9-yl)dibenzofuran, 2-(10-phenyl-9-anthryl)benzo Examples include zo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-{4-[10-(biphenyl-4-yl)-9-anthryl]phenyl}-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), etc. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred choices because they exhibit very good properties.

[0202] The host material may be a mixture of multiple substances, and when a mixture of host materials is used, it is preferable to mix a material having electron-transporting properties with a material having hole-transporting properties. By mixing a material having electron-transporting properties with a material having hole-transporting properties, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region can also be easily controlled. The weight ratio of the content of the material having hole-transporting properties to the material having electron-transporting properties may be 1:19 to 19:1 (material having hole-transporting properties:material having electron-transporting properties).

[0203] 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.

[0204] 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.

[0205] At least one of the materials forming the exciplex may be a phosphorescent material, which allows triplet excitation energy to be efficiently converted into singlet excitation energy by reverse intersystem crossing.

[0206] 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).

[0207] 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.

[0208] The electron transport layer 114 is a layer containing a material having an electron transport property. The material having an electron transport property is a material having an electron mobility of 1×10 at a square root of an electric field strength [V / cm] of 600. -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2 A substance having an electron mobility of 1 / Vs or more is preferred. Note that other substances can be used as long as they have a higher electron transporting property than holes. Note that the organic compound is preferably an organic compound having a π-electron-deficient heteroaromatic ring. The organic compound having a π-electron-deficient heteroaromatic ring is preferably one or more of, for example, an organic compound having a heteroaromatic ring with an azole skeleton, an organic compound having a heteroaromatic ring with a pyridine skeleton, an organic compound having a heteroaromatic ring with a diazine skeleton, and an organic compound having a heteroaromatic ring with a triazine skeleton.

[0209] The organic compounds having electron transport properties that can be used in the electron transport layer 114 can be similar to the organic compounds that can be used in the light-emitting layer 113. Among these, organic compounds containing a heteroaromatic ring with a diazine skeleton, an organic compound containing a heteroaromatic ring with a pyridine skeleton, and an organic compound containing a heteroaromatic ring with a triazine skeleton are preferred because of their excellent reliability. In particular, organic compounds containing a heteroaromatic ring with a diazine (pyrimidine or pyrazine) skeleton and an organic compound containing a heteroaromatic ring with a triazine skeleton have high electron transport properties and contribute to reduced driving voltage. Organic compounds having a phenanthroline skeleton, such as mTpPPhen, PnNPhen, and mPPhen2P, are particularly preferred, with organic compounds having a phenanthroline dimer structure, such as mPPhen2P, being more preferred due to their excellent stability.

[0210] In addition, in Embodiment 1, the organic compound represented by the general formula (G3) is also an organic compound having a π-electron-deficient heteroaromatic ring skeleton, and therefore can be suitably used as a material having an electron-transporting property.

[0211] The electron transport layer 114 may have a laminated structure. A layer in the electron transport layer 114 having a laminated structure that is in contact with the light-emitting layer 113 may function as a hole-blocking layer. When the electron transport layer in contact with the light-emitting layer is made to function as a hole-blocking layer, it is preferable to use a material whose HOMO level is lower than the HOMO level of the material contained in the light-emitting layer 113 by 0.5 eV or more.

[0212] The electron-injection layer 115 may be a layer containing a compound or complex of an alkali metal or alkaline earth metal such as 8-hydroxyquinolinato-lithium (abbreviation: Liq), 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviation: hpp2Py), or the organic compound represented by general formula (G3) in Embodiment 1. The electron-injection layer 115 may be a layer made of a substance having an electron-transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof.

[0213] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1B). The charge generation layer 116 is a layer that can inject 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. The charge generation layer 116 includes at least a second layer 117 that is a p-type layer. The second layer 117 is preferably formed using the composite material listed above as a material that can form the hole injection layer 111. The second layer 117 may also be formed by stacking a film containing an acceptor material and a film containing a hole transport material, which are listed above as materials that form the composite material. By applying a potential to the second layer 117, electrons are injected into the electron transport layer 114 and holes are injected into the cathode, thereby operating the light-emitting device. Furthermore, since the organic compound of one embodiment of the present invention has a low refractive index, its use in the second layer 117 allows a light-emitting device with high external quantum efficiency to be obtained.

[0214] In addition, the charge generation layer 116 preferably has, in addition to the second layer 117 which is a p-type layer, either or both of a first layer 119 which is an electron injection buffer layer and a third layer 118 which is an electron relay layer.

[0215] The first layer 119 can be made of a substance with high electron injection properties, such as an alkali metal, an alkaline earth metal, a rare earth metal, or a compound thereof (an alkali metal compound (including an oxide such as lithium oxide, a halide, or a carbonate such as lithium carbonate or cesium carbonate), an alkaline earth metal compound (including an oxide, a halide, or a carbonate), or a rare earth metal compound (including an oxide, a halide, or a carbonate)).

[0216] When the first layer 119 is formed containing a substance having an electron-transporting property 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 an electron-transporting property can be formed using the same material as the material for forming the electron-transporting layer 114 described above.

[0217] When the first layer 119 is formed containing a substance having an electron-transporting property and a donor substance, it is preferable that the first layer 119 further contains the organic compound of one embodiment of the present invention represented by the general formula (G3) because this can suppress an increase in driving voltage when the EL layer is processed by photolithography.

[0218] The third layer 118 contains at least a substance having an electron-transporting property and has a function of smoothly transferring electrons by preventing interaction between the first layer 119 and the second layer 117. The LUMO level of the substance having an electron-transporting property contained in the third layer 118 is preferably between the LUMO level of the acceptor substance in the second layer 117 and the LUMO level of the substance contained in the layer of the electron-transporting layer 114 that is in contact with the charge-generating layer 116. The specific energy level of the LUMO level of the substance having an electron-transporting property used in the third 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 an electron-transporting property used in the third layer 118 is preferably a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0219] The second electrode 102 is an electrode including a cathode. The second electrode 102 may have a laminated structure, in which case the layer in contact with the organic compound layer 103 functions as the cathode. Materials that form the cathode include metals, alloys, electrically conductive compounds, and mixtures thereof, each having a low work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include alkali metals such as lithium (Li) or cesium (Cs), elements belonging to Group 1 or Group 2 of the periodic table such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys (MgAg, AlLi), and compounds (lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), etc.) containing these elements, rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these elements. However, by providing the electron injection layer 115 or a thin film of the above-mentioned material with a small work function between the second electrode 102 and the electron transport layer, various conductive materials, such as Al, Ag, ITO, indium oxide-tin oxide containing silicon or silicon oxide, can be used as the cathode regardless of the magnitude of the work function.

[0220] When the second electrode 102 is formed using a material that is transparent to visible light, a light-emitting device that emits light from the second electrode 102 side can be obtained.

[0221] These conductive materials can be formed into films by dry methods such as vacuum deposition or sputtering, inkjet methods, spin coating, etc. Alternatively, they may be formed by wet methods using a sol-gel method, or by wet methods using a paste of a metal material.

[0222] In addition, various methods, whether dry or wet, can be used to form the organic compound layer 103. For example, vacuum deposition, gravure printing, offset printing, screen printing, inkjet printing, spin coating, or the like may be used.

[0223] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0224] Next, an embodiment of a light-emitting device having a structure in which multiple light-emitting units are stacked (also referred to as a stacked element or a tandem element) will be described with reference to FIG. 1(C). This light-emitting device has multiple light-emitting units between an anode and a cathode. One light-emitting unit has a structure substantially similar to that of the organic compound layer 103 shown in FIG. 1(A). In other words, the light-emitting device shown in FIG. 1(C) is a light-emitting device having multiple light-emitting units, and the light-emitting device shown in FIG. 1(A) or 1(B) can be said to be a light-emitting device having one light-emitting unit.

[0225] 1(C), a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between a first electrode 501 and a second electrode 502, and an intermediate layer 513 is provided between the first light-emitting unit 511 and the second light-emitting unit 512. The first electrode 501 and the second electrode 502 correspond to the first electrode 101 and the second electrode 102 in FIG. 1(A), respectively, and the same elements as those described in the description of FIG. 1(A) can be applied to them. The first light-emitting unit 511 and the second light-emitting unit 512 may have the same structure or different structures.

[0226] The intermediate layer 513 has a function of injecting electrons into one light-emitting unit and injecting holes into the other light-emitting unit when a voltage is applied between the first electrode 501 and the second electrode 502. That is, in FIG. 1C, when a voltage is applied so that the potential of the anode is higher than the potential of the cathode, the intermediate layer 513 only needs to inject electrons into the first light-emitting unit 511 and inject holes into the second light-emitting unit 512.

[0227] The intermediate layer 513 is preferably formed to have the same structure as the charge generation layer 116 described in FIG. 1B. A composite material of an organic compound and a metal oxide has excellent carrier injection and carrier transport properties, and therefore can realize low-voltage driving and low-current driving.

[0228] In particular, the first layer 119 in the intermediate layer 513 preferably contains the organic compound represented by general formula (G3) disclosed in Embodiment 1. By containing the organic compound represented by general formula (G3) disclosed in Embodiment 1, electron injection properties are improved, and a light-emitting device with a low driving voltage can be obtained.

[0229] Furthermore, the first layer 119 containing the organic compound represented by general formula (G3) disclosed in embodiment 1 can improve the donor property of the metal or metal compound by coordinating the organic compound represented by general formula (G3) to the metal or metal compound. This can prevent the function of the first layer 119 in the intermediate layer 513 from being impaired even when the organic compound layer 503 is exposed to the air atmosphere, thereby preventing an increase in driving voltage and providing a light-emitting device with good characteristics.

[0230] In other words, a tandem light-emitting device having an intermediate layer 513 having a first layer 119 containing an organic compound represented by general formula (G3) disclosed in embodiment 1 and a metal or metal compound can be made into a light-emitting device with low driving voltage and good characteristics.

[0231] Furthermore, a tandem light-emitting device having an intermediate layer 513 having a first layer 119 containing an organic compound represented by general formula (G3) disclosed in embodiment 1, a metal or a metal compound, and an organic compound having electron transport properties can be fabricated into a light-emitting device with good characteristics without a significant increase in driving voltage even when processed by a photolithography method including an atmospheric exposure step.

[0232] When the anode side surface of the light-emitting unit is in contact with the intermediate layer 513, the intermediate layer 513 can also serve as the hole injection layer of the light-emitting unit, so that the light-emitting unit does not need to be provided with a hole injection layer.

[0233] Furthermore, when the first layer 119 is provided in the intermediate layer 513, the first layer 119 plays the role of an electron injection layer in the light-emitting unit on the anode side, so it is not necessarily necessary to form an electron injection layer in the light-emitting unit on the anode side.

[0234] 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 an intermediate layer 513, as in the light-emitting device according to this embodiment, high-luminance light emission can be achieved while maintaining a low current density, and an element with a long life can be realized. Furthermore, a light-emitting device that can be driven at a low voltage and consumes low power can be realized.

[0235] 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.

[0236] Each layer and electrode, such as the organic compound layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and the intermediate layer 513, can be formed by, for example, an evaporation method (including a vacuum evaporation method), a droplet discharge method (also called an inkjet 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.

[0237] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate.

[0238] (Embodiment 3) In this embodiment, an example in which a light-emitting device according to one embodiment of the present invention is used as a display element of a display device will be described. Note that although the light-emitting device is shown in this embodiment as being formed by a photolithography method, it may be formed by a method using a fine metal mask or the like.

[0239] As shown in FIG. 2B, a plurality of light-emitting devices 130 are formed on an insulating layer 175 to form a display device.

[0240] The display device has a pixel section 177 in which a plurality of pixels 178 are arranged in a matrix. The pixel 178 has a sub-pixel 110R, a sub-pixel 110G, and a sub-pixel 110B.

[0241] In this specification and the like, when describing matters common to, for example, the subpixels 110R, 110G, and 110B, they may be referred to as the subpixels 110. When describing matters common to other components distinguished by alphabets, they may also be described using symbols without the alphabets.

[0242] The sub-pixel 110R emits red light, the sub-pixel 110G emits green light, and the sub-pixel 110B emits blue light. This allows an image to be displayed in the pixel unit 177. In this embodiment, sub-pixels of three colors, red (R), green (G), and blue (B), are described as an example, but combinations of sub-pixels of other colors may also be used. The number of sub-pixels is not limited to three, and may be four or more. Examples of four sub-pixels include sub-pixels of four colors: R, G, B, and white (W); sub-pixels of four colors: R, G, B, and yellow (Y); and sub-pixels of R, G, B, and infrared (IR).

[0243] In this specification, the row direction may be referred to as the X direction, and the column direction may be referred to as the Y direction. The X direction and the Y direction intersect, for example, perpendicularly.

[0244] 2A shows an example in which sub-pixels of different colors are arranged side by side in the X direction, and sub-pixels of the same color are arranged side by side in the Y direction. Note that sub-pixels of different colors may also be arranged side by side in the Y direction, and sub-pixels of the same color may also be arranged side by side in the X direction.

[0245] A connection portion 140 may be provided outside the pixel portion 177, and a region 141 may be provided. The region 141 is provided between the pixel portion 177 and the connection portion 140. The region 141 is provided with an organic compound layer 103. Furthermore, the connection portion 140 is provided with a conductive layer 151C.

[0246] 2A shows an example in which the region 141 and the connection portion 140 are located on the right side of the pixel portion 177, but the positions of the region 141 and the connection portion 140 are not particularly limited. The region 141 and the connection portion 140 may be singular or plural.

[0247] 2(B) is an example of a cross-sectional view taken along dashed line A1-A2 in FIG. 2(A). As shown in FIG. 2(B), the display device includes an insulating layer 171, a conductive layer 172 on the insulating layer 171, an insulating layer 173 on the insulating layer 171 and on the conductive layer 172, an insulating layer 174 on the insulating layer 173, and an insulating layer 175 on the insulating layer 174. The insulating layer 171 is provided on a substrate (not shown). The insulating layer 175, the insulating layer 174, and the insulating layer 173 have openings that reach the conductive layer 172, and a plug 176 is provided to fill the opening.

[0248] In the pixel section 177, the light-emitting device 130 is provided on the insulating layer 175 and the plug 176. A protective layer 131 is provided to cover the light-emitting device 130. The substrate 120 is bonded to the protective layer 131 by a resin layer 122. Preferably, an inorganic insulating layer 125 and an insulating layer 127 on the inorganic insulating layer 125 are provided between adjacent light-emitting devices 130.

[0249] 2B shows multiple cross sections of the inorganic insulating layer 125 and the insulating layer 127, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are connected to one another when the display device is viewed from above. That is, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are insulating layers having openings over the first electrodes.

[0250] FIG. 2B shows light-emitting device 130 as light-emitting device 130R, light-emitting device 130G, and light-emitting device 130B. Light-emitting device 130R, light-emitting device 130G, and light-emitting device 130B emit light of different colors. For example, light-emitting device 130R can emit red light, light-emitting device 130G can emit green light, and light-emitting device 130B can emit blue light. Light-emitting device 130R, light-emitting device 130G, or light-emitting device 130B may also emit other visible light or infrared light. Note that in FIG. 2B, light-emitting device 130R and light-emitting device 130G, and light-emitting device 130G and light-emitting device 130B can be considered adjacent light-emitting devices.

[0251] The display device of one embodiment of the present invention can be, for example, a top-emission type that emits light in the direction opposite to the substrate on which the light-emitting device is formed. Note that the display device of one embodiment of the present invention may also be a bottom-emission type.

[0252] Light-emitting device 130R is a light-emitting device that emits red light (preferably phosphorescence) and preferably has the configuration shown in Embodiment 2. It has a first electrode (pixel electrode) composed of conductive layer 151R and conductive layer 152R, a first layer 135R on the first electrode, a common layer 104 on first layer 135R, and a second electrode (common electrode) 102 on common layer 104. Common layer 104 is preferably an electron injection layer or a stack of an electron transport layer and an electron injection layer.

[0253] Light-emitting device 130G is a light-emitting device that emits green light (preferably phosphorescence) and preferably has the configuration shown in Embodiment 2. It has a first electrode (pixel electrode) composed of conductive layers 151G and 152G, a first layer 135G on the first electrode, a common layer 104 on first layer 135G, and a second electrode (common electrode) 102 on common layer 104. Common layer 104 is preferably an electron injection layer or a stack of an electron transport layer and an electron injection layer.

[0254] The light-emitting device 130B is a light-emitting device that emits blue light (preferably fluorescence) and preferably has the structure described in Embodiment 2. It includes a first electrode (pixel electrode) including a conductive layer 151B and a conductive layer 152B, a first layer 135B on the first electrode, a common layer 104 on the first layer 135B, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 is preferably an electron injection layer or a stack of an electron transport layer and an electron injection layer. The stack of the first layer 135 and the common layer 104 corresponds to the organic compound layer 103 in FIG. 1A and the like.

[0255] When the common layer 104 is not provided, the first layer 135 corresponds to the organic compound layer 103 .

[0256] One of the pixel electrode (first electrode) and the common electrode (second electrode) of the light-emitting device functions as an anode, and the other functions as a cathode. In this embodiment, unless otherwise specified, the pixel electrode functions as an anode and the common electrode functions as a cathode.

[0257] The first layers 135R, 135G, and 135B are independent and island-like for each light-emitting device or each emitted color. Preferably, the first layers 135R, 135G, and 135B do not overlap with each other. The first layers 135R, 135G, and 135B, which are included in multiple light-emitting devices 130 formed in a light-emitting device, are sometimes collectively referred to as the first layer group 135A. By providing the first layer group 135A in an island-like configuration for each light-emitting device 130, leakage current between adjacent light-emitting devices 130 can be suppressed even in high-resolution display devices. This prevents crosstalk and enables the realization of a display device with extremely high contrast. In particular, a display device with high current efficiency at low luminance can be realized.

[0258] The island-shaped first layer group 135A is formed by depositing an EL film for each emitted color and processing the EL film using photolithography.

[0259] The first layer 135 is preferably provided so as to cover the top and side surfaces of the first electrode 101 (pixel electrode) of the light-emitting device 130. This makes it easier to increase the aperture ratio of the display device compared to a configuration in which the end of the first layer 135 is located inside the end of the pixel electrode. Furthermore, covering the side surfaces of the pixel electrode of the light-emitting device 130 with the first layer 135 prevents the first electrode 101 and the second electrode 102 from coming into contact with each other, thereby preventing short circuits in the light-emitting device 130.

[0260] In the display device of one embodiment of the present invention, the first electrode 101 (pixel electrode) of the light-emitting device preferably has a stacked-layer structure. For example, in the example shown in FIG. 2B, the first electrode 101 of the light-emitting device 130 has a stacked-layer structure of a conductive layer 151 provided on the insulating layer 171 side and a conductive layer 152 provided on the organic compound layer side.

[0261] For example, a metal material can be used for the conductive layer 151. Specifically, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd), etc., and alloys containing appropriate combinations of these metals can also be used.

[0262] The conductive layer 152 can be formed using an oxide containing one or more selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon. For example, it is preferable to use a conductive oxide containing one or more of indium oxide, indium tin oxide, indium zinc oxide, zinc oxide, zinc oxide containing gallium, titanium oxide, indium zinc oxide containing gallium, indium zinc oxide containing aluminum, indium tin oxide containing silicon, and indium zinc oxide containing silicon. In particular, indium tin oxide containing silicon has a large work function, for example, a work function of 4.0 eV or more, and therefore can be suitably used for the conductive layer 152.

[0263] The conductive layer 151 may have a stacked structure of multiple layers containing different materials, and the conductive layer 152 may have a stacked structure of multiple layers containing different materials. In this case, the conductive layer 151 may include a layer containing a material that can be used for the conductive layer 152, such as a conductive oxide, or the conductive layer 152 may include a layer containing a material that can be used for the conductive layer 151, such as a metal material. For example, when the conductive layer 151 has a stacked structure of two or more layers, a layer in contact with the conductive layer 152 can be a layer containing a material that can be used for the conductive layer 152.

[0264] Note that the conductive layer 151 preferably has a tapered edge. Specifically, the conductive layer 151 preferably has a tapered edge with a taper angle of less than 90°. In this case, the conductive layer 152 provided along the side surface of the conductive layer 151 also has a tapered edge. By tapering the side surface of the conductive layer 152, coverage of the first layer 135 provided along the side surface of the conductive layer 152 can be improved.

[0265] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate.

[0266] (Fourth embodiment) In this embodiment, a display device according to one embodiment of the present invention will be described.

[0267] The display device of the present embodiment can be a high-definition display device, and can therefore be used as a display unit for information terminals (wearable devices) such as wristwatches and bracelets, as well as for wearable devices that can be worn on the head, such as VR devices such as head-mounted displays (HMDs) and AR devices such as glasses.

[0268] The display device of the present embodiment can be a high-resolution display device or a large-sized display device. Therefore, the display device of the present embodiment can be used in electronic devices having relatively large screens, such as television devices, desktop or notebook personal computers, computer monitors, digital signage, and large game machines such as pachinko machines, as well as in the display units of digital cameras, digital video cameras, digital photo frames, mobile phones, portable game machines, personal digital assistants, and sound reproducing devices.

[0269] [Display module] 3A shows a perspective view of a display module 280. The display module 280 includes a display device 100A and an FPC 290. Note that the display device included in the display module 280 is not limited to the display device 100A, and may be any of display devices 100B to 100E described later.

[0270] The display module 280 has a substrate 291 and a substrate 292. The display module 280 has a display unit 281. The display unit 281 is a region that displays an image in the display module 280, and is a region where light from each pixel provided in a pixel unit 284 (described later) can be viewed.

[0271] 3(B) is a perspective view schematically showing the configuration on the substrate 291 side. A circuit portion 282, a pixel circuit portion 283 on the circuit portion 282, and a pixel portion 284 on the pixel circuit portion 283 are stacked on the substrate 291. A terminal portion 285 for connecting to an FPC 290 is provided in a portion of the substrate 291 that does not overlap with the pixel portion 284. The terminal portion 285 and the circuit portion 282 are electrically connected by a wiring portion 286 composed of a plurality of wirings.

[0272] The pixel section 284 has a plurality of periodically arranged pixels 284a. An enlarged view of one pixel 284a is shown on the right side of Fig. 3(B). The various configurations described in the previous embodiments can be applied to the pixel 284a. Fig. 3(B) shows an example in which the pixel 284a has the same configuration as the pixel 178 shown in Fig. 2.

[0273] The pixel circuit section 283 has a plurality of pixel circuits 283a arranged periodically.

[0274] One pixel circuit 283a is a circuit that controls the driving of a plurality of elements included in one pixel 284a.

[0275] The circuit portion 282 includes a circuit for driving each pixel circuit 283a of the pixel circuit portion 283. For example, it is preferable that the circuit portion 282 includes one or both of a gate line driver circuit and a source line driver circuit. In addition, the circuit portion 282 may include at least one of an arithmetic circuit, a memory circuit, a power supply circuit, and the like.

[0276] The FPC 290 functions as wiring for supplying a video signal, a power supply potential, or the like from the outside to the circuit section 282. An IC may be mounted on the FPC 290.

[0277] The display module 280 can be configured such that one or both of the pixel circuit unit 283 and the circuit unit 282 are stacked below the pixel unit 284, thereby making it possible to extremely increase the aperture ratio (effective display area ratio) of the display unit 281.

[0278] Such a display module 280 has extremely high resolution and can therefore be suitably used in VR devices such as HMDs or glasses-type AR devices. For example, even in a configuration in which the display unit of the display module 280 is viewed through lenses, the display module 280 has an extremely high-resolution display unit 281, so that even if the display unit is enlarged with the lenses, the pixels are not visible, allowing for a highly immersive display. Furthermore, the display module 280 is not limited to this and can be suitably used in electronic devices having relatively small display units.

[0279] [Display device 100A] The display device 100A shown in FIG. 4A includes a substrate 301, a light-emitting device 130R, a light-emitting device 130G, a light-emitting device 130B, a capacitor 240, and a transistor 310.

[0280] The substrate 301 corresponds to the substrate 291 in FIGS. 3A and 3B. The transistor 310 has a channel formation region in the substrate 301. The substrate 301 can be a semiconductor substrate such as a single crystal silicon substrate. The transistor 310 includes a part of the substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 functions as a gate electrode. The insulating layer 313 is located between the substrate 301 and the conductive layer 311 and functions as a gate insulating layer. The low-resistance region 312 is a region in which the substrate 301 is doped with impurities and functions as a source or drain. The insulating layer 314 is provided to cover a side surface of the conductive layer 311.

[0281] Furthermore, an element isolation layer 315 is provided between two adjacent transistors 310 so as to be embedded in the substrate 301 .

[0282] In addition, an insulating layer 261 is provided to cover the transistor 310 , and a capacitor 240 is provided on the insulating layer 261 .

[0283] Capacitor 240 has conductive layer 241, conductive layer 245, and insulating layer 243 located therebetween. Conductive layer 241 functions as one electrode of capacitor 240, conductive layer 245 functions as the other electrode of capacitor 240, and insulating layer 243 functions as a dielectric of capacitor 240.

[0284] The conductive layer 241 is provided over the insulating layer 261 and is buried in the insulating layer 254. The conductive layer 241 is electrically connected to one of the source and drain of the transistor 310 by a plug 271 buried in the insulating layer 261. The insulating layer 243 is provided to cover the conductive layer 241. The conductive layer 245 is provided in a region overlapping with the conductive layer 241 with the insulating layer 243 interposed therebetween.

[0285] An insulating layer 255 is provided to cover the capacitor 240, an insulating layer 174 is provided on the insulating layer 255, and an insulating layer 175 is provided on the insulating layer 174. Light-emitting device 130R, light-emitting device 130G, and light-emitting device 130B are provided on the insulating layer 175. An insulator is provided in the region between adjacent light-emitting devices.

[0286] Insulating layer 156R is provided to have a region overlapping with a side surface of conductive layer 151R, insulating layer 156G is provided to have a region overlapping with a side surface of conductive layer 151G, and insulating layer 156B is provided to have a region overlapping with a side surface of conductive layer 151B. Furthermore, conductive layer 152R is provided to cover conductive layer 151R and insulating layer 156R, conductive layer 152G is provided to cover conductive layer 151G and insulating layer 156G, and conductive layer 152B is provided to cover conductive layer 151B and insulating layer 156B. Sacrificial layer 158R is located on first layer 135R, sacrificial layer 158G is located on first layer 135G, and sacrificial layer 158B is located on first layer 135B.

[0287] The conductive layer 151R, the conductive layer 151G, and the conductive layer 151B are electrically connected to one of the source and drain of the transistor 310 via an insulating layer 243, an insulating layer 255, an insulating layer 174, a plug 256 embedded in the insulating layer 175, a conductive layer 241 embedded in the insulating layer 254, and a plug 271 embedded in the insulating layer 261. Various conductive materials can be used for the plug.

[0288] Furthermore, a protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. A substrate 120 is bonded to the protective layer 131 via a resin layer 122. For details of the components from the light-emitting devices 130 to the substrate 120, refer to Embodiment 3. The substrate 120 corresponds to the substrate 292 in FIG. 3(A).

[0289] Fig. 4(B) is a modified example of the display device 100A shown in Fig. 4(A). The display device shown in Fig. 4(B) has a colored layer 132R, a colored layer 132G, and a colored layer 132B, and the light-emitting device 130 has an area where it overlaps with one of the colored layers 132R, 132G, and 132B. In the display device shown in Fig. 4(B), the light-emitting device 130 can emit, for example, white light. Furthermore, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light.

[0290] [Display device 100B] FIG. 5 shows a perspective view of the display device 100B, and FIG. 6 shows a cross-sectional view of the display device 100C.

[0291] The display device 100B has a configuration in which a substrate 352 and a substrate 351 are bonded together. In Fig. 5, the substrate 352 is indicated by a dashed line.

[0292] The display device 100B has a pixel unit 177, a connection unit 140, a circuit 356, wiring 355, etc. Fig. 5 shows an example in which an IC 354 and an FPC 353 are mounted on the display device 100B. Therefore, the configuration shown in Fig. 5 can also be called a display module having the display device 100B, an IC (integrated circuit), and an FPC. Here, a display device having a connector such as an FPC attached to a substrate, or a display device having an IC mounted on the substrate, is called a display module.

[0293] The connection section 140 is provided outside the pixel section 177. There may be one or more connection sections 140. The connection section 140 electrically connects the common electrode of the light-emitting device and the conductive layer, and can supply a potential to the common electrode.

[0294] The circuit 356 can be, for example, a scanning line driver circuit.

[0295] The wiring 355 has a function of supplying signals and power to the pixel portion 177 and the circuit 356. The signals and power are input to the wiring 355 from the outside via the FPC 353 or from the IC 354.

[0296] 5 shows an example in which an IC 354 is provided on a substrate 351 by a COG (Chip On Glass) method or a COF (Chip on Film) method. The IC 354 may be, for example, an IC having a scanning line driver circuit or a signal line driver circuit. The display device 100B and the display module may not include an IC. Alternatively, the IC may be mounted on an FPC by, for example, a COF method.

[0297] Figure 6 shows an example of a cross section of the display device 100B, where a portion of the area including the FPC 353, a portion of the circuit 356, a portion of the pixel section 177, a portion of the connection section 140, and a portion of the area including the end portion are cut away.

[0298] [Display device 100C] The display device 100C shown in Figure 6 has, between a substrate 351 and a substrate 352, a transistor 201, a transistor 205, a light-emitting device 130R that emits red light, a light-emitting device 130G that emits green light, and a light-emitting device 130B that emits blue light, etc.

[0299] For details of the light emitting devices 130R, 130G, and 130B, see the second embodiment.

[0300] Light-emitting device 130R has conductive layer 224R, conductive layer 151R on conductive layer 224R, and conductive layer 152R on conductive layer 151R. Light-emitting device 130G has conductive layer 224G, conductive layer 151G on conductive layer 224G, and conductive layer 152G on conductive layer 151G. Light-emitting device 130B has conductive layer 224B, conductive layer 151B on conductive layer 224B, and conductive layer 152B on conductive layer 151B.

[0301] The conductive layer 224R is connected to the conductive layer 222b of the transistor 205 through an opening provided in the insulating layer 214. An end of the conductive layer 151R is located outside an end of the conductive layer 224R. An insulating layer 156R is provided to have a region in contact with a side surface of the conductive layer 151R, and a conductive layer 152R is provided to cover the conductive layer 151R and the insulating layer 156R.

[0302] Conductive layer 224G, conductive layer 151G, conductive layer 152G, and insulating layer 156G in light-emitting device 130G, and conductive layer 224B, conductive layer 151B, conductive layer 152B, and insulating layer 156B in light-emitting device 130B are similar to conductive layer 224R, conductive layer 151R, conductive layer 152R, and insulating layer 156R in light-emitting device 130R, and therefore detailed description thereof will be omitted.

[0303] Recesses are formed in the conductive layers 224R, 224G, and 224B so as to cover the openings provided in the insulating layer 214. A layer 128 is buried in the recesses.

[0304] Layer 128 has the function of planarizing the recesses of conductive layer 224R, conductive layer 224G, and conductive layer 224B. Conductive layers 151R, 151G, and 151B, which are electrically connected to conductive layer 224R, conductive layer 224G, and conductive layer 224B, are provided on conductive layer 224R, conductive layer 224G, and conductive layer 224B and layer 128. Therefore, the regions overlapping with the recesses of conductive layer 224R, conductive layer 224G, and conductive layer 224B can also be used as light-emitting regions, thereby increasing the aperture ratio of the pixel.

[0305] The layer 128 may be an insulating layer or a conductive layer. Various inorganic insulating materials, organic insulating materials, and conductive materials can be used for the layer 128 as appropriate. In particular, the layer 128 is preferably formed using an insulating material, and is particularly preferably formed using an organic insulating material. For example, the organic insulating materials that can be used for the insulating layer 127 described above can be used for the layer 128.

[0306] A protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. The protective layer 131 and the substrate 352 are bonded via an adhesive layer 142. A light-shielding layer 157 is provided on the substrate 352. A solid sealing structure, a hollow sealing structure, or the like can be applied to seal the light-emitting device 130. In FIG. 6, the space between the substrates 352 and 351 is filled with the adhesive layer 142, and a solid sealing structure is applied. Alternatively, the space may be filled with an inert gas (nitrogen, argon, etc.), and a hollow sealing structure may be applied. In this case, the adhesive layer 142 may be provided so as not to overlap with the light-emitting devices. Alternatively, the space may be filled with a resin different from the frame-shaped adhesive layer 142.

[0307] 6 shows an example in which connecting portion 140 has conductive layer 224C obtained by processing the same conductive film as conductive layers 224R, 224G, and 224B, conductive layer 151C obtained by processing the same conductive film as conductive layers 151R, 151G, and 151B, and conductive layer 152C obtained by processing the same conductive film as conductive layers 152R, 152G, and 152B. Also, FIG. 6 shows an example in which insulating layer 156C is provided so as to have an area overlapping with a side surface of conductive layer 151C.

[0308] The display device 100B is a top-emission type. Light emitted by the light-emitting device is emitted toward the substrate 352. The substrate 352 is preferably made of a material that is highly transparent to visible light. When the light-emitting device emits infrared or near-infrared light, it is preferably made of a material that is highly transparent to such light. The first electrode (pixel electrode) contains a material that reflects visible light, and the second electrode (counter electrode) contains a material that transmits visible light.

[0309] An insulating layer 211, an insulating layer 213, an insulating layer 215, and an insulating layer 214 are provided over the substrate 351 in this order. A part of the insulating layer 211 functions as a gate insulating layer for each transistor. A part of the insulating layer 213 functions as a gate insulating layer for each transistor. The insulating layer 215 is provided to cover the transistor. The insulating layer 214 is provided to cover the transistor and functions as a planarization layer. Note that the number of gate insulating layers and the number of insulating layers covering the transistors are not limited, and each may be a single layer or two or more layers.

[0310] The insulating layers 211, 213, and 215 are each preferably formed using an inorganic insulating film.

[0311] The insulating layer 214, which functions as a planarizing layer, is preferably an organic insulating layer.

[0312] The transistor 201 and the transistor 205 each include a conductive layer 221 functioning as a gate, an insulating layer 211 functioning as a gate insulating layer, a conductive layer 222a and a conductive layer 222b functioning as a source and a drain, a semiconductor layer 231, an insulating layer 213 functioning as a gate insulating layer, and a conductive layer 223 functioning as a gate.

[0313] A connection portion 204 is provided in a region of the substrate 351 where the substrate 352 does not overlap. In the connection portion 204, a wiring 355 is electrically connected to the FPC 353 via a conductive layer 166 and a connection layer 242. The conductive layer 166 has an example of a laminated structure including a conductive film obtained by processing the same conductive film as the conductive layers 224R, 224G, and 224B, a conductive film obtained by processing the same conductive film as the conductive layers 151R, 151G, and 151B, and a conductive film obtained by processing the same conductive film as the conductive layers 152R, 152G, and 152B. The conductive layer 166 is exposed on the upper surface of the connection portion 204. This allows the connection portion 204 and the FPC 353 to be electrically connected via the connection layer 242.

[0314] It is preferable to provide a light-shielding layer 157 on the surface of the substrate 352 facing the substrate 351. The light-shielding layer 157 can be provided between adjacent light-emitting devices, on the connection section 140, on the circuit 356, etc. Also, various optical members can be arranged on the outside of the substrate 352.

[0315] The substrate 351 and the substrate 352 can be made of the same material as can be used for the substrate 120 .

[0316] The adhesive layer 142 can be made of a material that can be used for the resin layer 122 .

[0317] The connection layer 242 may be an anisotropic conductive film (ACF), an anisotropic conductive paste (ACP), or the like.

[0318] [Display device 100D] The display device 100D shown in FIG. 7 differs from the display device 100C shown in FIG. 6 mainly in that it is a bottom-emission display device.

[0319] Light emitted from the light emitting device is emitted toward the substrate 351. It is preferable that a material with high transparency to visible light is used for the substrate 351. On the other hand, the light transparency of the material used for the substrate 352 is not an issue.

[0320] It is preferable to form a light-shielding layer between the substrate 351 and the transistor 201 and between the substrate 351 and the transistor 205. Figure 7 shows an example in which a light-shielding layer 157 is provided over the substrate 351, an insulating layer 153 is provided over the light-shielding layer 157, and the transistors 201, 205, etc. are provided over the insulating layer 153.

[0321] Light emitting device 130R includes conductive layer 112R, conductive layer 126R on conductive layer 112R, and conductive layer 129R on conductive layer 126R.

[0322] Light emitting device 130B includes conductive layer 112B, conductive layer 126B on conductive layer 112B, and conductive layer 129B on conductive layer 126B.

[0323] A material that is highly transparent to visible light is used for each of the conductive layers 112R, 112B, 126R, 126B, 129R, and 129B. It is preferable to use a material that reflects visible light for the second electrode.

[0324] Although the light emitting device 130G is not shown in FIG. 7, the light emitting device 130G is also provided.

[0325] In addition, although FIG. 7 and other figures show an example in which the top surface of the layer 128 has a flat portion, the shape of the layer 128 is not particularly limited.

[0326] [Display device 100E] The display device 100E shown in FIG. 8 is a modified example of the display device 100C shown in FIG. 6, and differs from the display device 100C mainly in that it has colored layers 132R, 132G, and 132B.

[0327] In the display device 100E, the light-emitting device 130 has an area that overlaps one of the colored layer 132R, the colored layer 132G, and the colored layer 132B. The colored layer 132R, the colored layer 132G, and the colored layer 132B can be provided on the surface of the substrate 352 facing the substrate 351. An end of the colored layer 132R, an end of the colored layer 132G, and an end of the colored layer 132B can overlap the light-shielding layer 157.

[0328] In the display device 100E, the light-emitting device 130 can emit, for example, white light. Furthermore, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light. The display device 100E may be configured such that the colored layers 132R, 132G, and 132B are provided between the protective layer 131 and the adhesive layer 142.

[0329] Although FIGS. 6 and 8 show an example in which the top surface of the layer 128 has a flat portion, the shape of the layer 128 is not particularly limited.

[0330] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate.

[0331] (Embodiment 5) In this embodiment, an electronic device according to one embodiment of the present invention will be described.

[0332] The electronic devices of this embodiment include the display device of one embodiment of the present invention in their display portions. The display device of one embodiment of the present invention consumes low power and can therefore be used in the display portions of various electronic devices.

[0333] Examples of electronic devices include electronic devices with relatively large screens such as television sets, desktop or notebook personal computers, computer monitors, digital signage, large game machines such as pachinko machines, as well as digital cameras, digital video cameras, digital photo frames, mobile phones, portable game machines, personal digital assistants, and sound playback devices.

[0334] In particular, the display device of one embodiment of the present invention has low power consumption and can be suitably used in relatively small electronic devices. Examples of such electronic devices include wristwatch-type and bracelet-type information terminals (wearable devices), and head-mounted wearable devices such as VR devices (head-mounted displays), eyeglass-type AR devices, and MR devices.

[0335] The electronic device of this embodiment may have a sensor (including a function to measure 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 rays).

[0336] An example of a wearable device that can be worn on the head will be described with reference to FIGS. 9(A) to 9(D).

[0337] The electronic device 700A shown in FIG. 9(A) and the electronic device 700B shown in FIG. 9(B) each have a pair of display panels 751, a pair of housings 721, a communication unit (not shown), a pair of mounting units 723, a control unit (not shown), an imaging unit (not shown), a pair of optical members 753, a frame 757, and a pair of nose pads 758.

[0338] The display device of one embodiment of the present invention can be applied to the display panel 751. Therefore, the electronic device can have low power consumption and can be driven for a long time.

[0339] The electronic device 700A and the electronic device 700B can each project an image displayed on the display panel 751 onto a display area 756 of the optical member 753. Because the optical member 753 is translucent, the user can see the image displayed in the display area superimposed on a transmitted image visible through the optical member 753.

[0340] Electronic device 700A and electronic device 700B may be provided with a camera capable of capturing an image in front of them as an imaging unit. Furthermore, electronic device 700A and electronic device 700B may each be provided with an acceleration sensor such as a gyro sensor, thereby detecting the orientation of the user's head and displaying an image corresponding to that orientation in display area 756.

[0341] The communication unit has a wireless communication device, and can supply, for example, a video signal via the wireless communication device. Note that instead of or in addition to the wireless communication device, a connector to which a cable through which a video signal and a power supply potential can be connected may be provided.

[0342] Furthermore, the electronic device 700A and the electronic device 700B are provided with batteries, which can be charged wirelessly and / or by wire.

[0343] The housing 721 may be provided with a touch sensor module.

[0344] Various touch sensors can be used as the touch sensor module. For example, various types of touch sensors can be used, such as a capacitance type, a resistive film type, an infrared type, an electromagnetic induction type, a surface acoustic wave type, or an optical type. In particular, it is preferable to use a capacitance type or an optical type sensor in the touch sensor module.

[0345] The electronic device 800A shown in Figure 9(C) and the electronic device 800B shown in Figure 9(D) each have a pair of display units 820, a housing 821, a communication unit 822, a pair of mounting units 823, a control unit 824, a pair of imaging units 825, and a pair of lenses 832.

[0346] The display device of one embodiment of the present invention can be applied to the display portion 820. Therefore, the electronic device can have low power consumption and can be driven for a long time.

[0347] Display unit 820 is provided inside housing 821 at a position that can be viewed through lens 832. Also, by displaying different images on the pair of display units 820, it is possible to perform a three-dimensional display using parallax.

[0348] It is preferable that electronic device 800A and electronic device 800B each have a mechanism that allows the left and right positions of lens 832 and display unit 820 to be adjusted so that they are optimally positioned according to the position of the user's eyes.

[0349] The wearing part 823 allows the user to wear the electronic device 800A or the electronic device 800B on the head.

[0350] The imaging unit 825 has a function of acquiring external information. Data acquired by the imaging unit 825 can be output to the display unit 820. An image sensor can be used for the imaging unit 825. Furthermore, multiple cameras may be provided to support multiple angles of view, such as telephoto and wide angle.

[0351] The electronic device 800A may have a vibration mechanism that functions as a bone conduction earphone.

[0352] The electronic device 800A and the electronic device 800B may each have an input terminal to which a cable can be connected for supplying a video signal from a video output device or the like and power for charging a battery provided in the electronic device.

[0353] The electronic device of one embodiment of the present invention may have a function of wirelessly communicating with the earphone 750 .

[0354] 9B includes an earphone unit 727. A part of a wiring connecting the earphone unit 727 and a control unit may be disposed inside the housing 721 or the attachment unit 723.

[0355] 9(D) includes an earphone unit 827. For example, the earphone unit 827 and the control unit 824 can be configured to be connected to each other by wire.

[0356] As described above, the electronic devices of one embodiment of the present invention are preferably either glasses-type devices (such as the electronic devices 700A and 700B) or goggle-type devices (such as the electronic devices 800A and 800B).

[0357] An electronic device 6500 shown in FIG. 10A is a portable information terminal that can be used as a smartphone.

[0358] The electronic device 6500 includes a housing 6501, a display portion 6502, a power button 6503, a button 6504, a speaker 6505, a microphone 6506, a camera 6507, and a light source 6508. The display portion 6502 has a touch panel function.

[0359] The display device of one embodiment of the present invention can be applied to the display portion 6502. Therefore, the electronic device can have low power consumption and can be driven for a long time.

[0360] FIG. 10B is a schematic cross-sectional view including the end portion of the housing 6501 on the microphone 6506 side.

[0361] A light-transmitting protective member 6510 is provided on the display surface side of the housing 6501, and a display panel 6511, optical members 6512, a touch sensor panel 6513, a printed circuit board 6517, a battery 6518, etc. are arranged in the space surrounded by the housing 6501 and the protective member 6510.

[0362] A display panel 6511, an optical member 6512, and a touch sensor panel 6513 are fixed to the protective member 6510 by adhesive layers (not shown).

[0363] In an area outside the display unit 6502, a part of the display panel 6511 is folded back, and an FPC 6515 is connected to the folded back part. An IC 6516 is mounted on the FPC 6515. The FPC 6515 is connected to a terminal provided on a printed circuit board 6517.

[0364] The display device of one embodiment of the present invention can be applied to the display panel 6511. Therefore, an extremely lightweight electronic device can be realized. Furthermore, since the display panel 6511 is extremely thin, a large-capacity battery 6518 can be mounted thereon while keeping the thickness of the electronic device small. Furthermore, by folding back a part of the display panel 6511 and arranging a connection portion with the FPC 6515 on the back side of the pixel portion, an electronic device with a narrow frame can be realized.

[0365] 10C shows an example of a television set. A television set 7100 includes a display portion 7000 built in a housing 7171. Here, the housing 7171 is supported by a stand 7173.

[0366] The display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can have low power consumption and can be driven for a long time.

[0367] The television set 7100 shown in FIG. 10C can be operated using an operation switch provided on a housing 7171 and a separate remote control 7151.

[0368] 10D shows an example of a laptop personal computer 7200. The laptop personal computer 7200 includes a housing 7211, a keyboard 7212, a pointing device 7213, and an external connection port 7214. A display portion 7000 is incorporated in the housing 7211.

[0369] The display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can have low power consumption and can be driven for a long time.

[0370] 10(E) and 10(F) show an example of digital signage.

[0371] 10E includes a housing 7301, a display portion 7000, and a speaker 7303. The digital signage 7300 may further include an LED lamp, operation keys (including a power switch or an operation switch), a connection terminal, various sensors, a microphone, and the like.

[0372] 10F shows a digital signage 7400 attached to a cylindrical pillar 7401. The digital signage 7400 has a display unit 7000 provided along the curved surface of the pillar 7401.

[0373] 10E and 10F, the display device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can have high reliability.

[0374] The larger the display unit 7000, the more information can be provided at one time. Also, the larger the display unit 7000, the more easily it will attract people's attention, which can increase the advertising effectiveness of, for example, advertisements.

[0375] Furthermore, as shown in Figures 10(E) and 10(F), it is preferable that the digital signage 7300 or the digital signage 7400 be able to wirelessly communicate with an information terminal 7311 or an information terminal 7411 such as a smartphone carried by a user.

[0376] The electronic devices shown in Figures 11(A) to 11(G) have a housing 9000, a display portion 9001, a speaker 9003, operation keys 9005 (including a power switch or an operation switch), a connection terminal 9006, a sensor 9007 (including a function to measure force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), a microphone 9008, etc.

[0377] 11(A) to 11(G) have various functions, such as a function to display various information (still images, videos, text images, etc.) on a display unit, a touch panel function, a function to display a calendar, date, time, etc., a function to control processing by various software (programs), a wireless communication function, a function to read and process programs or data recorded on a recording medium, etc.

[0378] The electronic devices shown in FIGS. 11A to 11G will be described in detail below.

[0379] FIG. 11A is a perspective view showing a mobile information terminal 9171. The mobile information terminal 9171 can be used as, for example, a smartphone. Note that the mobile information terminal 9171 may be provided with a speaker 9003, a connection terminal 9006, a sensor 9007, or the like. The mobile information terminal 9171 can display text and image information on multiple surfaces thereof. FIG. 11A shows an example in which three icons 9050 are displayed. Information 9051 indicated by a dashed rectangle can also be displayed on another surface of the display unit 9001. Examples of the information 9051 include notifications of incoming emails, SNS messages, phone calls, etc., the title of the email or SNS message, the sender's name, the date and time, the remaining battery level, and radio wave intensity. Alternatively, the icon 9050 or the like may be displayed in the position where the information 9051 is displayed.

[0380] 11B is a perspective view of a mobile information terminal 9172. The mobile information terminal 9172 has a function of displaying information on three or more surfaces of the display portion 9001. Here, an example is shown in which information 9052, information 9053, and information 9054 are displayed on different surfaces. For example, a user can check information 9053 displayed in a position where the mobile information terminal 9172 can be observed from above while the mobile information terminal 9172 is placed in a breast pocket of clothes.

[0381] 11C is a perspective view of a tablet terminal 9173. The tablet terminal 9173 is capable of executing various applications such as mobile phone calls, e-mails, document browsing and creation, music playback, internet communication, and computer games. The tablet terminal 9173 has a display portion 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front side of a housing 9000, operation keys 9005 as operation buttons on the left side of the housing 9000, and a connection terminal 9006 on the bottom.

[0382] FIG. 11D is a perspective view showing a wristwatch-type mobile information terminal 9200. The mobile information terminal 9200 can be used as, for example, a smart watch (registered trademark). The display surface of the display portion 9001 is curved, and display can be performed along the curved display surface. The mobile information terminal 9200 can also perform hands-free conversation by communicating with, for example, a headset capable of wireless communication. The mobile information terminal 9200 can also perform data transmission and reception with another information terminal and charge itself through a connection terminal 9006. Note that charging may be performed by wireless power supply.

[0383] 11(E) to 11(G) are perspective views showing a foldable mobile information terminal 9201. FIG. 11(E) shows the mobile information terminal 9201 in an unfolded state, FIG. 11(G) shows it in a folded state, and FIG. 11(F) is a perspective view showing a state in the process of changing from one of FIG. 11(E) and FIG. 11(G) to the other. The mobile information terminal 9201 is highly portable when folded, and has a seamless, wide display area when unfolded, providing excellent viewability of the display. A display portion 9001 of the mobile information terminal 9201 is supported by three housings 9000 connected by hinges 9055. For example, the display portion 9001 can be bent with a curvature radius of 0.1 mm to 150 mm.

[0384] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate. [Example]

[0385] Synthesis Example 1 This synthesis example describes a method for synthesizing 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: 4Cl7HidPhen), an organic compound of the present invention represented by structural formula (259) in Embodiment 1. The structure of 4Cl7HidPhen is shown below.

[0386] [ka]

[0387] A 100 mL three-neck flask was charged with 2.9 g (12 mmol) of 4,7-dichloro-1,10-phenanthroline, 2.8 mL (24 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 4.9 g (35 mmol) of potassium carbonate (K2CO3), and 24 mL of N-methylpyrrolidone (NMP). The mixture was stirred at 80 °C for 5 hours. After cooling to room temperature, 50 mL of water and 50 mL of chloroform were added to the flask, and the mixture was separated using a separatory funnel. Extraction was performed three times with chloroform, and the resulting organic layer was washed once with purified water. The organic layer was gravity filtered, and the filtrate was concentrated to obtain a solid. A small amount of acetone was added to the solid to obtain a suspension of the target product. The suspension was then suction filtered to obtain 3.6 g (92% yield) of the target pale yellow solid. The synthesis scheme (s1-1) is shown below.

[0388] [ka]

[0389] The resulting pale yellow solid 1 The results of the H NMR measurements are shown in Figures 12(A) to 12(C). Figure 12(B) shows an enlarged view of the range from 6.5 ppm to 9.0 ppm in Figure 12(A), and Figure 12(C) shows an enlarged view of the range from 1 ppm to 4.0 ppm. 1 The results of the HNMR measurements are shown below.

[0390] 1 H NMR (CD2Cl2,500MHz): δ=8.89(1H,d,J=5.0Hz), 8.64(1H,d,J=5.5Hz), 8.35(1H,d,J=10Hz), 7.95(1H,d,J=1 0Hz), 7.63(1H,d,J=4.5Hz), 6.73(1H,d,J=5.0Hz), 3.75-3.60(4H,m), 2.41-2.34(2H,m), 1.70-1.38(8H,m).

[0391] Furthermore, the molecular weight of the resulting pale yellow solid was measured using liquid chromatography mass spectrometry (LC / MS analysis).

[0392] LC / MS analysis was performed using a Waters Acquity UPLC for LC separation and a Waters Xevo G2 Tof MS for MS analysis. The column used for LC separation was an Acquity UPLC BEH C8 (2.1 x 100 mm, 1.7 μm), and the column temperature was 40°C. The mobile phases were acetonitrile (mobile phase A) and 0.1% formic acid (mobile phase B). The sample was prepared by placing 2.0 mg of 4Cl7HidPhen in a sample bottle and adding 1.0 mL of dichloromethane using a micropipette to dissolve the solution (1.0 mL). To this solution, 9.0 mL of acetonitrile was added using a micropipette to adjust the concentration of 4Cl7HidPhen to 200 ppm. The sample injection volume was 5.0 μL.

[0393] A gradient method was used for LC separation, changing the mobile phase composition. From 0 to 1 minute after the start of measurement, the ratio of mobile phase A to mobile phase B was set to 30:70. The composition was then changed so that at 10 minutes, the ratio of mobile phase A to mobile phase B was 95:5. The composition was changed linearly.

[0394] In the MS analysis, ionization was performed by electrospray ionization (ESI), with a capillary voltage of 3.01075 kV, a sample cone voltage of 30 V, and positive mode detection. The mass range measured was m / z = 100 to 1200.

[0395] As a result of LC / MS analysis, a peak showing m / z 338 was observed, which corresponds to the calculated mass of 4Cl7HidPhen, 337. This is thought to be the peak of a proton adduct of 4Cl7HidPhen.

[0396] 1 The results of 1 H NMR and LC / MS analysis showed that 4Cl7HidPhen was obtained in this synthesis example.

[0397] Here, we will explain the results of a synthesis similar to that in the examples, using the synthesis method disclosed in Non-Patent Document 1. The synthesis method disclosed in Non-Patent Document 1 uses diisopropylethylamine as a base.

[0398] A 24 mm diameter glass standard reaction vessel was charged with 1.0 g (4.0 mmol) of 4,7-dichloro-1,10-phenanthroline, 1.0 g (8.1 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 1.6 g (12 mmol) of diisopropylethylamine, and 8 mL of N-methylpyrrolidone (NMP), and the mixture was stirred at 80 °C for 5 hours. After cooling to room temperature, the solid precipitated in the reaction vessel was filtered, yielding 0.13 g of a yellow solid. The synthesis scheme (s1-2) of this synthesis example is shown below.

[0399] [ka]

[0400] The resulting yellow solid 1 The results of the H NMR measurements are shown in Figures 13(A) to 13(C). Figure 13(B) shows an enlarged view of the range from 6.5 ppm to 9.0 ppm in Figure 13(A), and Figure 13(C) shows an enlarged view of the range from 1 ppm to 4.0 ppm. 1 The results of the HNMR measurements are shown below.

[0401] 1 H NMR (CD2Cl2,500MHz): δ=8.58(2H,d,J=5.5Hz), 7.98(2H,s), 6.65(2H,d,J=5.0), 3.80-3.60(8H,m), 2.45-2.30(4H,m), 1.85-1.35(16H,m).

[0402] The resulting yellow solid was analyzed by LC / MS and its mass was measured. The chromatogram showed a peak at m / z 427. This peak is believed to be the peak of a proton adduct of 4,7-di(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (Hid2Phen) (calculated mass: 426), an organic compound in which two 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl groups are bonded to 1,10-phenanthroline.

[0403] 1 The results of H NMR and LC / MS analysis confirmed that the synthesis method disclosed in Non-Patent Document 1 yielded Hid2Phen. This synthesis method selectively affords only 4,7-di(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as Hid2Phen). Conventionally, in compounds with two or more symmetric functional groups, when the functional groups exhibit essentially the same reactivity or reaction selectivity, it has been difficult to selectively react only one of them. While it is not uncommon to improve reaction selectivity in coupling reactions, for example, by modifying the ligand of the transition metal catalyst, there are very few examples of controlling reactivity using a simple, classical nucleophilic substitution reaction like this method. Therefore, this application can be considered an excellent method for asymmetrically modifying symmetric functional groups in compounds.

[0404] From the above results, it was found that the target compound, 4Cl7HidPhen, was hardly obtained when using diisopropylethylamine, which is used in the synthesis method disclosed in Non-Patent Document 1. As described above, it becomes difficult to synthesize an asymmetric 1,10-phenanthroline derivative simply by changing the type of base used, and therefore the synthesis method of one embodiment of the present invention was found to be a very useful synthesis method for obtaining an asymmetric 1,10-phenanthroline derivative. [Example]

[0405] Synthesis Example 2 Example 1 This example describes a synthesis method of 4-chloro-7-(1-pyrrolidinyl)-1,10-phenanthroline (abbreviation: 4Cl7PrdPhen) represented by the structural formula (200) in Embodiment 1. The structure of 4Cl7PrdPhen is shown below.

[0406] [ka]

[0407] 30 g (0.12 mol) of 4,7-dichloro-1,10-phenanthroline, 8.5 g (0.12 mol) of 1H-pyrrolidine, 50 g (0.36 mol) of potassium carbonate, and 0.24 L of 1-methyl-2-pyrrolidone (NMP) were added to a 1000 mL three-neck flask and stirred at 100°C for 5 hours under a nitrogen atmosphere. After stirring, the mixture was allowed to cool to room temperature. Insoluble matter was removed by suction filtration, and the resulting filtrate was extracted with dichloromethane. The extract was concentrated to obtain an oil. Hexane was added to the oil and stirred at 0°C. The precipitated solid was collected by suction filtration. Ethyl acetate and hexane were added to the solid, and the mixture was subjected to ultrasonic irradiation. The solid was collected by suction filtration, yielding the target pale brown solid (19 g, 56% yield). The synthesis scheme of this synthesis example is shown in formula (s2-1) below.

[0408] [ka]

[0409] The resulting light brown solid 1 The HNMR spectra are shown in Figures 14(A) to 14(C). Figure 14(B) shows an enlarged view of the range from 6.5 ppm to 9.5 ppm in Figure 14(A), and Figure 14(C) shows an enlarged view of the range from 1 ppm to 4.0 ppm. 1 The results of HNMR measurement are shown below, and it was confirmed that 4Cl7PrdPhen was obtained.

[0410] 1 HNMR(CDCl3,300MHz):δ=8.99(1H,d,J=4.8Hz),8.77(1H,d,J=5.5Hz),8.29(1H,d,J=9.5Hz),7.97( 1H,d,J=9.5Hz),7.65(1H,d,J=4.8Hz),6.77(1H,d,J=5.5Hz),3.73-3.69(4H,m),2.10-2.05(4H,m).

[0411] Thus, it was demonstrated that the synthesis method according to one embodiment of the present invention is a method that does not lose selectivity even when scaled up. [Example]

[0412] Synthesis Example 3 Example 1 This example describes a synthesis method of 4-bromo-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: 4Br7HidPhen) represented by structural formula (202) in Embodiment 1. The structure of 4Br7HidPhen is shown below.

[0413] [ka]

[0414] 10 g (30 mmol) of 4,7-dibromo-1,10-phenanthroline, 3.7 g (30 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 12 g (87 mmol) of potassium carbonate, and 0.10 L of 1-methyl-2-pyrrolidone (NMP) were added to a 1000 mL three-neck flask and stirred at 100 °C for 7 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. Insoluble matter was removed by suction filtration, and the resulting filtrate was extracted with dichloromethane. The extract was concentrated to obtain an oil. This oil was purified by silica gel column chromatography (eluent: ethyl acetate, then chloroform, then methanol). The resulting fraction was concentrated to obtain an oil. A small amount of chloroform and ethyl acetate were added to this oil, and the mixture was subjected to ultrasonic irradiation. The precipitated solid was collected by suction filtration to obtain the target yellow solid (7.6 g, yield 69%). The synthesis scheme of this synthesis example is shown in the following formula (s3-1).

[0415] [ka]

[0416] The resulting yellow solid 1 The HNMR spectra are shown in Figures 15(A) to 15(C). Figure 15(B) shows an enlarged view of the range from 6.5 ppm to 9.0 ppm in Figure 15(A), and Figure 15(C) shows an enlarged view of the range from 1 ppm to 4.0 ppm. 1 The results of HNMR measurement are shown below, and it was confirmed that 4Br7HidPhen was obtained.

[0417] 1 HNMR(CDCl3,300MHz):δ=8.88(1H,d,J=4.8Hz),8.76(1H,d,J=5.9Hz),8.32(1H,d,J=9.5Hz),7.93(1H,d,J =9.5Hz),7.84(1H,d,J=4.8Hz),6.73(1H,d,J=5.9Hz),3.77-3.62(4H,m),2.40(2H,br),1.62-1.45(8H,m). [Example]

[0418] Synthesis Example 4 Example 1 This example describes a synthesis method of 4-bromo-7-(1-pyrrolidinyl)-1,10-phenanthroline (abbreviation: 4Br7PrdPhen) represented by the structural formula (201) in Embodiment 1. The structure of 4Br7PrdPhen is shown below.

[0419] [ka]

[0420] 1.5 g (4.4 mmol) of 4,7-dibromo-1,10-phenanthroline, 0.32 g (4.5 mmol) of 1H-pyrrolidine, 1.8 g (13 mmol) of potassium carbonate, and 10 mL of 1-methyl-2-pyrrolidone (NMP) were added to a 50 mL three-neck flask and stirred at 100 °C for 7 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. Insoluble matter from the mixture was filtered off by suction. Water was added to the filtrate, which was then extracted with dichloromethane. The extract was concentrated to obtain an oil. This oil was purified by silica gel column chromatography (eluent: ethyl acetate, then chloroform, then methanol). The resulting fraction was concentrated to obtain an oil. A small amount of chloroform and ethyl acetate were added to the oil, and the mixture was subjected to ultrasonic irradiation. The precipitated solid was collected by suction filtration, yielding the desired yellow solid (0.77 g, 51% yield). The synthesis scheme of this synthesis example is shown in formula (s4-1) below.

[0421] [ka]

[0422] The resulting yellow solid 1 The H NMR spectra are shown in Figures 16(A) to 16(C). Figure 16(B) shows an enlarged view of the range from 6.5 ppm to 9.0 ppm in Figure 16(A), and Figure 16(C) shows an enlarged view of the range from 1 ppm to 4.0 ppm. 1The results of HNMR measurement are shown below, and it was confirmed that 4Br7PrdPhen was obtained.

[0423] 1 HNMR(CDCl3,300MHz):δ=8.88(1H,d,J=4.8Hz),8.78(1H,d,J=5.5Hz),8.30(1H,d,J=9.5Hz),7.94( 1H,d,J=9.5Hz),7.85(1H,d,J=4.8Hz),6.77(1H,d,J=5.9Hz),3.74-3.70(4H,m),2.11-2.07(4H,m). [Example]

[0424] Synthesis Example 5 This synthesis example describes a method for synthesizing 2-chloro-9-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: 2Cl9HidPhen), an organic compound of the present invention represented by structural formula (203) in Embodiment 1. The structure of 2Cl9HidPhen is shown below.

[0425] [ka]

[0426] A 24 mm diameter glass standard reaction vessel was charged with 1.0 g (4.0 mmol) of 2,9-dichloro-1,10-phenanthroline, 1.1 mL (8.4 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 1.7 g (12 mmol) of potassium carbonate (K2CO3), and 8 mL of N-methylpyrrolidone (NMP), and the mixture was stirred at 80 °C for 4 hours. The mixture was cooled to room temperature, water was added, and then extraction with chloroform was performed. This extract was washed once with saturated brine. After separation, the organic layer was gravity filtered, and the resulting filtrate was concentrated to precipitate a yellow solid. Suction filtration yielded 1.3 g of a yellow solid containing the target compound. This solid was purified by silica gel column chromatography (eluent: chloroform) to obtain the target yellow solid (0.67 g, 50% yield). The synthesis scheme (s5-1) of this synthesis example is shown below.

[0427] [ka]

[0428] The resulting yellow solid 1 The results of the H NMR measurements are shown in Figures 17(A) to 17(C). Figure 17(B) shows an enlarged view of the range from 6.5 ppm to 8.5 ppm in Figure 17(A), and Figure 17(C) shows an enlarged view of the range from 1 ppm to 4.0 ppm. 1 The results of the HNMR measurements are shown below.

[0429] 1 H NMR (CD2Cl2,500MHz): δ=8.11(1H,d,J=8.5Hz), 7.94(1H,d,J=9.5Hz), 7.64(1H,d,J=8.5Hz), 7.47(1H,d,J=8.0 Hz), 7.42(1H,d,J=8.5Hz), 6.75(1H,d,J=9.0Hz), 4.20-3.00(8H,br), 2.50-2.35(4H,br), 1.76-1.35(16H,m).

[0430] The molecular weight of the resulting yellow solid was measured using LC / MS analysis. As a result, a peak showing m / z 338 was observed, while the calculated mass of the target substance was 337. This peak is thought to be a peak indicating a proton adduct of 2Cl9HidPhen.

[0431] 1 The results of 1 H NMR and LC / MS analysis showed that 2Cl9HidPhen was obtained by this synthesis example. [Example]

[0432] Synthesis Example 6 This synthesis example describes a method for synthesizing 4-chloro-4'-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-2,2'-bipyridine (abbreviation: 4Cl4'HidBpy), an organic compound of the present invention represented by structural formula (204) in Embodiment 1. The structure of 4Cl4'HidBpy is shown below.

[0433] [ka]

[0434] A 24 mm diameter glass standard reaction vessel was charged with 1.0 g (4.4 mmol) of 4,4'-dichloro-2,2'-bipyridine, 1.1 mL (9.0 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 1.8 g (13 mmol) of potassium carbonate (KCO), and 9 mL of N-methylpyrrolidone (NMP), and the mixture was stirred at 80°C for 6 hours. The mixture was cooled to room temperature, water was added, and then extracted with chloroform. The resulting extract was gravity filtered, and the filtrate was concentrated to obtain an oil. This oil was purified by silica gel column chromatography (eluent: ethyl acetate, then chloroform, then ethanol). The resulting fraction was concentrated to obtain an oil. A small amount of chloroform and hexane was added to this oil, and the mixture was subjected to ultrasonic irradiation. The precipitated solid was collected by suction filtration to obtain the target white solid (0.45 g, yield 32%). The synthesis scheme (s6-1) of this synthesis example is shown below.

[0435] [ka]

[0436] The resulting white solid 1 The results of the H NMR measurements are shown in Figures 18(A) to 18(C). Figure 18(B) shows an enlarged view of the range from 6.0 ppm to 9.0 ppm in Figure 18(A), and Figure 18(C) shows an enlarged view of the range from 1 ppm to 4.0 ppm. 1 The results of the HNMR measurements are shown below.

[0437] 1 H NMR (CD2Cl2,500MHz): δ=8.49(1H,d,J=5.0Hz), 8.43(1H,d,J=2.5Hz), 8.20(1H,d,J=5.0Hz), 7.52(1H,d,J=2.0Hz) , 7.27(1H,dd,J=5.3Hz,2.0Hz), 6.39(1H,dd,J=6.0Hz,3.0Hz), 3.46-3.20(4H,m),2.35(2H,m),1.70-1.34(8H,m).

[0438] The molecular weight of the resulting white solid was measured using LC / MS analysis. As a result, a peak showing m / z 314 was observed, while the calculated mass of the target substance was 313. This is thought to be the peak of a proton adduct of 4Cl4'HidBpy.

[0439] 1 H NMR and LC / MS analysis indicated that 4Cl4'HidBpy was obtained. [Example]

[0440] Synthesis Example 7 Example 1 This example describes a synthesis method for 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-(3,4-diphenyl-1-pyrrolidinyl)-1,10-phenanthroline (abbreviation: Hid-DPPrdPhen) represented by structural formula (100) in Embodiment 1. The structure of Hid-DPPrdPhen is shown below.

[0441] [ka]

[0442] A 50 mL three-neck flask was charged with 2.8 g (8.3 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 2.0 g (9.0 mmol) of rac trans-3,4-diphenylpyrrolidine, and 3.7 g (24 mmol) of diazabicycloundecene (DBU). The mixture was stirred at 100 °C for 8 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. Water was added to the mixture, followed by extraction with chloroform. The extract was concentrated to obtain an oil. Ethyl acetate and hexane were added to the oil, and the mixture was subjected to ultrasonic irradiation. The solid was collected by suction filtration, yielding the target pale brown solid (2.5 g, 58% yield). The synthetic scheme of this synthesis example is shown in formula (s7-1) below.

[0443] [ka]

[0444] Of the resulting 2.5 g of light brown solid, 1.3 g was purified by train sublimation. The sublimation purification was carried out under an argon flow rate of 0 mL / min and a pressure of 2.8 × 10 -2 The reaction was carried out for 24 hours under the conditions of Pa and a heating temperature of 255° C. As a result, a yellow solid (0.53 g, recovery rate 41%) was obtained as the target product.

[0445] The resulting yellow solid 1 The H NMR spectra are shown in Figures 19(A) to 19(C). Figure 19(B) shows an enlarged view of the range from 6.5 ppm to 9.0 ppm in Figure 19(A), and Figure 19(C) shows an enlarged view of the range from 1 ppm to 4.0 ppm. 1 The results of H NMR measurement are shown below, and it was confirmed that Hid-DPPrdPhen was obtained by this synthesis example.

[0446] 1 H NMR (CD2Cl2,300MHz):δ=8.68(1H,d,J=5.1Hz),8.62(1H,d,J=5.5Hz),8.02-7.92(2H,m),7.33-7.21(10H,m),6.77(1H,d,J=5.1Hz),6.68(1H,d,J =5.5Hz),4.17-4.02(4H,m),3.83-3.71(4H,m),3.63-3.57(1H,m),3.52 -3.47(1H,m),2.44-2.37(1H,m),2.33-2.27(1H,m),1.63-1.32(8H,m).

[0447] The glass transition temperature (Tg) of Hid-DPPrdPhen was measured. Tg was measured using a differential scanning calorimeter (DSC8500, manufactured by PerkinElmer Japan Co., Ltd.) by placing the powder in an aluminum cell and raising the temperature at a rate of 40°C / min. As a result, the Tg of Hid-DPPrdPhen was found to be 129°C, indicating that it has good heat resistance.

[0448] Next, a solubility test of Hid-DPPrdPhen was conducted. This test was carried out at 1 atm and room temperature (RT).

[0449] <Solubility Test of Hid-DPPrdPhen by LC / MS Analysis> For LC / MS analysis, LC (liquid chromatography) separation was performed using an Acquity UPLC manufactured by Waters, and MS analysis (mass spectrometry) was performed using an Xevo G2 Tof MS manufactured by Waters. For LC separation, an Acquity UPLC BEH C8 (2.1×100 mm 1.7 μm) column was used. The mobile phase A was acetonitrile, and the mobile phase B was an aqueous solution of 0.1% formic acid. The sample injection volume was 5.0 μL. The analysis was carried out using a wavelength of 254 nm ± 1 nm for the photodiode array detector.

[0450] ​​​​​​​​​​​​​​​​​​This synthesis example describes a method for synthesizing 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-[3-(1-naphthyl)-1-pyrrolidinyl]-1,10-phenanthroline (abbreviation: Hid-αNPrdPhen), which is represented by structural formula (101) in Embodiment 1. The structure of Hid-αNPrdPhen is shown below.

[0454] [ka]

[0455] A 50 mL three-neck flask was charged with 2.6 g (7.7 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 2.0 g (8.6 mmol) of 3-(naphthalen-1-yl)pyrrolidine hydrochloride, and 3.6 g (24 mmol) of diazabicycloundecene (DBU). The mixture was stirred at 100 °C for 8 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. Water was added to the mixture, followed by extraction with chloroform. The extract was concentrated to obtain an oil. Acetone was added to the oil, and the mixture was subjected to ultrasonic irradiation. The solid was collected by suction filtration, yielding the target pale red solid (3.6 g, 92% yield). The synthetic scheme of this synthesis example is shown in formula (s8-1) below.

[0456] [ka]

[0457] Of the resulting pale red solid (3.6 g), 2.1 g was purified by train sublimation under conditions of argon flow rate of 0 mL / min and pressure of 4.5 × 10 -2 The reaction was carried out for 24 hours under the conditions of Pa and a heating temperature of 255° C. As a result, a yellow solid (0.20 g, recovery rate 9.5%) was obtained as the target product.

[0458] The resulting yellow solid 1The 1H NMR spectra are shown in FIGS. 20(A) to 20(C). FIG. 20(B) is an enlarged view of the range from 6.5 ppm to 9.0 ppm in FIG. 20(A), and FIG. 20(C) is an enlarged view of the range from 1.0 ppm to 4.5 ppm. Also, 1 The measurement results by 1H NMR are shown below. From these results, it was confirmed that Hid-αNPrdPhen was obtained by this synthesis example.

[0459] 1 1H NMR (CDCl3, 300 MHz): δ = 8.79 (1H, d, J = 5.5 Hz), 8.73 (1H, d, J = 5.5 Hz), 8.16 (1H, d, J = 7.7 Hz), 7.99 - 7.89 (3H, m), 7.80 (1H, t, J = 4.6 Hz), 7.58 - 7.45 (4H, m), 6.79 (1H, d, J = 5.5 Hz), 6.67 (1H, d, J = 5.5 Hz), 4.38 - 4.25 (2H, m), 3.98 - 3.82 (3H, m), 3.76 - 3.55 (4H, m), 2.59 - 2.32 (4H, m), 1.63 - 1.39 (8H, m).

[0460] The glass transition temperature (Tg) of Hid-αNPrdPhen was measured. Tg was measured using a differential scanning calorimeter (DSC8500 manufactured by PerkinElmer Japan Co., Ltd.), placing the powder in an aluminum cell, and heating at a rate of 40 °C / min. As a result, the Tg of Hid-αNPrdPhen was 125 °C.

[0461] Next, a solubility test of Hid-αNPrdPhen was conducted. This test was carried out at 1 atm and room temperature (RT).

[0462] <Solubility Test of Hid-αNPrdPhen by LC / MS Analysis> LC / MS analysis was performed using a Waters Acquity UPLC for LC (liquid chromatography) separation and a Waters Xevo G2 Tof MS for MS (mass spectrometry). The column used for LC separation was an Acquity UPLC BEH C8 (2.1 x 100 mm, 1.7 μm). The mobile phases were acetonitrile (mobile phase A) and 0.1% formic acid (mobile phase B). The sample injection volume was 5.0 μL. The photodiode array detector wavelength was 254 nm ± 1 nm.

[0463] 1 mg of Hid-αNPrdPhen was placed in a 5 mL sample bottle, 2 mL of chloroform was added, and the mixture was sonicated for 10 minutes. After confirming that the solid was completely dissolved, the solution was diluted 2.5 times with acetonitrile to prepare a solution with a concentration of 0.20 g / L. This solution was then diluted with acetonitrile to prepare solutions with concentrations of 2.5 mg / L and 0.5 mg / L. LC / MS analysis was performed using the prepared solution, and a calibration curve was created using the peak area values ​​derived from Hid-αNPrdPhen obtained in the solutions of each concentration.

[0464] Next, the solubility of Hid-αNPrdPhen in water was measured.

[0465] 1 mg of Hid-αNPrdPhen was placed in a 5 mL sample bottle, 1 mL of water was added, and ultrasonic irradiation was performed for 5 minutes. This mixture was filtered using a membrane filter to remove solids, and the resulting filtrate was diluted 5 times with acetonitrile. The resulting solution was subjected to LC / MS analysis.

[0466] From the calibration curve and the signal intensity obtained by LC / MS analysis, it was found that 0.0023 mg of Hid-αNPrdPhen dissolves in 1 mL of water. The solubility of Hid-αNPrdPhen in water is 2.3 × 10 in weight fraction. -6 This indicates that Hid-αNPrdPhen has low solubility in water.

[0467] Therefore, it was found that Hid-αNPrdPhen, one embodiment of the present invention, has low solubility in water and can be suitably used in light-emitting devices whose manufacturing process includes treatment with water or chemical solutions containing water as a solvent (i.e., light-emitting devices processed using lithography methods). [Example]

[0468] Synthesis Example 9 This synthesis example describes a method for synthesizing 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-[4-(1-naphthyl)phenyl]-1,10-phenanthroline (abbreviation: Hid-αNPPhen), which is represented by structural formula (103) in Embodiment 1. The structure of Hid-αNPPhen is shown below.

[0469] [ka]

[0470] A 100 mL three-neck flask was charged with 2.4 g (6.3 mmol) of 4-bromo-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 1.7 g (6.9 mmol) of 4-(1-naphthyl)phenylboronic acid, 0.16 g (0.45 mmol) of di(1-adamantyl)-n-butylphosphine, 3.4 g (10 mmol) of cesium carbonate, 36 mL of 1,4-dioxane, and 13 mL of water, and the mixture was degassed by stirring under reduced pressure. To this mixture was added 0.17 g (0.19 mmol) of tris(dibenzylideneacetone)dipalladium(0), and the mixture was stirred at 100 °C for 30 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. Water was added to this mixture, and then extraction with dichloromethane was carried out. The extract was concentrated to obtain an oily product. This oily product was purified by silica gel column chromatography (developing solvent: chloroform followed by methanol). The obtained fraction was concentrated to obtain an oily product. A small amount of chloroform and ethyl acetate were added to this oily product, and the mixture was irradiated with ultrasound. The precipitated solid was collected by suction filtration to obtain the target pale brown solid (1.2 g, yield 39%). The synthesis scheme of this synthesis example is shown in formula (s9-1) below.

[0471] [ka]

[0472] The resulting light brown solid (1.2 g) was purified by train sublimation under an argon flow rate of 0 mL / min and a pressure of 3.2 × 10 -2 The reaction was carried out for 43 hours under the conditions of Pa and a heating temperature of 240° C. As a result, a yellow solid (0.55 g, recovery rate 46%) was obtained as the target substance.

[0473] The resulting yellow solid 1 The HNMR spectra are shown in Figures 21(A) to 21(C). Figure 21(B) shows an enlarged view of the range from 6.5 ppm to 9.5 ppm in Figure 21(A), and Figure 21(C) shows an enlarged view of the range from 1.0 ppm to 4.0 ppm. 1The results of HNMR measurement are shown below, and it was confirmed that Hid-αNPPhen was obtained.

[0474] 1 HNMR(CDCl3,300MHz):δ=9.20(1H,d,J=4.4Hz),8.79(1H,d,J=5.5Hz),8.23(1H,d,J=9.9Hz),8.04(1H,d,J=7.3Hz),7.97-7.91(2H,m ),7.83(1H,d,J=9.5Hz),7.69(4H,s),7.62-7.48(5H,m),6.75(1H,d,J=5.9Hz),3.77-3.63(4H,m),2.39(2H,br),1.64-1.46(8H,m).

[0475] The glass transition temperature (Tg) of Hid-αNPPhen was measured. Tg was measured using a differential scanning calorimeter (DSC8500, manufactured by PerkinElmer Japan Co., Ltd.) by placing the powder in an aluminum cell and heating it at a rate of 40°C / min. As a result, the Tg of Hid-αNPPhen was found to be 124°C, indicating good heat resistance. [Example]

[0476] Synthesis Example 10 This synthesis example describes a method for synthesizing 4-(6,7-dihydro-5H-dibenzo[c,e]azepin-5-yl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: Hid-ceHBazPhen), which is represented by structural formula (102) in Embodiment 1. The structure of Hid-ceHBazPhen is shown below.

[0477] [ka]

[0478] A 100 mL three-neck flask was charged with 3.4 g (10 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 2.6 g (11 mmol) of 6,7-dihydro-5H-dibenzo[c,e]azepine hydrochloride, and 4.6 g (30 mmol) of diazabicycloundecene (DBU), and the mixture was stirred at 100°C for 32 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. Water was added to the mixture, followed by extraction with chloroform. The extract was concentrated to obtain an oil. Ethyl acetate was added to the oil, and the mixture was subjected to ultrasonic irradiation. The precipitated solid was filtered off by suction filtration, and the filtrate was concentrated to obtain an oil. A small amount of ethyl acetate was added to this oil and the mixture was subjected to ultrasonic irradiation. The precipitated solid was collected by suction filtration to obtain the target pale brown solid (2.1 g, yield 42%). The synthesis scheme of this synthesis example is shown in the following formula (s10-1).

[0479] [ka]

[0480] The resulting light brown solid 1 The H NMR spectra are shown in Figures 22(A) to 22(C). Figure 22(B) shows an enlarged view of the range from 6.5 ppm to 9.0 ppm in Figure 22(A), and Figure 22(C) shows an enlarged view of the range from 1.0 ppm to 4.5 ppm. 1 The results of H NMR measurement are shown below, and it was confirmed that Hid-ceHBazPhen was obtained.

[0481] 1H NMR(CDCl3,300MHz):δ=8.87(1H,d,J=5.1Hz),8.75(1H,d,J=5.5Hz),8.14(1H, d,J=9.5Hz),7.83(1H,d,J=9.5Hz),7.60(2H,d,J=7.3Hz),7.51(2H,t,J=7.5Hz ),7.36(2H,t,J=7.3Hz),7.22(2H,d,J=7.3Hz),7.00(1H,d,J=5.1Hz),6.71(1H ,d,J=5.5Hz),4.27(4H,s),3.78-3.63(4H,m),2.39(2H,br),1.61-1.44(8H,m). [Example]

[0482] Example 1 In this example, a light-emitting device according to one embodiment of the present invention will be described in detail. The structural formulae of main organic compounds used in this example are shown below.

[0483] [ka]

[0484] (Method for fabricating light-emitting device 1-1) First, a silver, palladium, and copper alloy (APC: Ag-Pd-Cu) was formed on the substrate by sputtering to a thickness of 100 nm as a reflective electrode, and then indium tin oxide containing silicon oxide (ITSO) was deposited by sputtering to a thickness of 50 nm as a transparent electrode, forming a 2 mm x 2 mm first electrode 101. The transparent electrode functions as an anode, and is considered to be the first electrode 101 together with the reflective electrode.

[0485] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water and baked at 200°C for 1 hour.

[0486] Then, about 1 × 10 -4 The substrate was introduced into a vacuum deposition apparatus whose internal pressure had been reduced to 100 Pa, and after vacuum baking at 170° C. for 30 minutes in a heating chamber within the vacuum deposition apparatus, the substrate was allowed to cool for approximately 30 minutes.

[0487] Next, the substrate was fixed to a holder installed in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward, and N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBBiF) represented by the above structural formula (i) and a material (OCHD-003) having a molecular weight of 672 and electron acceptor properties, which contained fluorine, were co-deposited on the first electrode 101 by a deposition method at a weight ratio of 1:0.03 (= PCBBiF:OCHD-003) to a film thickness of 10 nm, thereby forming a hole injection layer 111.

[0488] On the hole injection layer 111, PCBBiF was evaporated to a film thickness of 110 nm to form a first hole transport layer.

[0489] Subsequently, on the first hole transport layer, 8-(p-terphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8mpTP-4mDBtPBfpm) represented by the above structural formula (ii), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: βNCCP) represented by the above structural formula (iii), and [2-d3-methyl-8-( The first light-emitting layer was formed by co-evaporation of [2-pyridinyl-κN]benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)) and [8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)] in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) to a thickness of 40 nm.

[0490] After this, 2-{3-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq) represented by the above structural formula (v) was evaporated to a film thickness of 10 nm to form a first electron transport layer.

[0491] After the formation of the first electron transport layer, 2,2'-([2,2'-bipyridine]-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 6,6'(P-Bqn)2BPy) represented by the above structural formula (vi), 4-(3,4-diphenyl-1-pyrrolidinyl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: Hid-DPPrdPhen) represented by the above structural formula (vii), and lithium oxide (LiO) were mixed. The first layer was formed by co-depositing the above compounds in a volume ratio of 0.5:0.5:0.02 (=6,6'(P-Bqn)BPy:Hid-DPPrdPhen:LiO) to a thickness of 5 nm, and the third layer was formed by co-depositing copper phthalocyanine (abbreviation: CuPc) represented by the above structural formula (viii) to a thickness of 2 nm. Furthermore, the second layer was formed by co-depositing PCBBiF and OCHD-003 in a weight ratio of 1:0.15 (=PCBBiF:OCHD-003) to a thickness of 10 nm, and an intermediate layer was formed.

[0492] On the intermediate layer, PCBBiF was evaporated to a thickness of 50 nm to form a second hole transport layer.

[0493] A second light-emitting layer was formed on the second hole-transporting layer by co-deposition of 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d3)2(mbfpypy-d3) in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) to a thickness of 40 nm.

[0494] Then, 2mPCCzPDBq was deposited to a thickness of 20 nm, and then 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P) represented by the above structural formula (ix) was deposited to a thickness of 20 nm to form a second electron transport layer.

[0495] Then, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited at a volume ratio of 1:0.5 (=LiF:Yb) to a film thickness of 1.5 nm to form an electron injection layer, and then silver (Ag) and magnesium (Mg) were co-deposited at a volume ratio of 1:0.1 to a film thickness of 15 nm to form the second electrode 102. In addition, 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) represented by the above structural formula (x) was deposited on the second electrode 102 as a cap layer at a film thickness of 70 nm to improve light extraction efficiency.

[0496] Next, in a glove box with a nitrogen atmosphere, the light-emitting device was sealed with a glass substrate to prevent it from being exposed to the atmosphere (a UV-curable sealant was applied around the element, UV was irradiated only onto the sealant without irradiating the light-emitting device, and heat treatment was performed at 80°C under atmospheric pressure for 1 hour), thereby forming light-emitting device 1-1.

[0497] (Method for fabricating light-emitting device 1-2) Light-emitting device 1-2 was fabricated in the same manner as light-emitting device 1-1, except that Hid-DPPrdPhen used in the first layer of light-emitting device 1-1 was replaced with 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-[3-(1-naphthyl)-1-pyrrolidinyl]-1,10-phenanthroline (abbreviation: Hid-αNPrdPhen) represented by the above structural formula (xi).

[0498] (Method for producing comparative light-emitting device 1) Comparative light-emitting device 1 was fabricated in the same manner as light-emitting device 1-1, except that Hid-DPPrdPhen used in the first layer in light-emitting device 1-1 was replaced with 4,7-di(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: Hid2Phen) represented by the above structural formula (xii).

[0499] The device structures of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1 are shown below.

[0500] [Table 1]

[0501] [Table 2]

[0502] The luminance-current density characteristics of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1 are shown in Figure 23, their current efficiency-luminance characteristics in Figure 24, their luminance-voltage characteristics in Figure 25, their current density-voltage characteristics in Figure 26, and their electroluminescence spectra in Figure 27. In addition, the luminance of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1 was 1000 cd / m 2 The main characteristics in this range are shown in Table 3. The luminance, CIE chromaticity, and electroluminescence spectrum were measured at room temperature using a spectroradiometer (SR-UL1R, manufactured by Topcon Corporation).

[0503] [Table 3]

[0504] 23 to 27 and Table 2 show that all the devices exhibit high current efficiency and function as tandem light-emitting devices.

[0505] From the above results, it was found that the light-emitting device in which the organic compound represented by general formula (G1) in the first layer of the tandem light-emitting device in embodiment 1 is a light-emitting device with good characteristics. [Example]

[0506] Example 1 In this example, a light-emitting device according to one embodiment of the present invention will be described in detail. The structural formulae of main organic compounds used in this example are shown below.

[0507] [ka]

[0508] (Method for fabricating light-emitting device 2-1) First, a silver-palladium-copper alloy (APC: Ag-Pd-Cu) film was formed on the substrate by sputtering to a thickness of 100 nm, and then a transparent electrode made of indium tin oxide containing silicon oxide (ITSO) was deposited by sputtering to a thickness of 50 nm. This laminated film was then patterned by photolithography to form the first electrode. The patterned first electrode consisted of multiple electrodes arranged in a 2 mm x 2 mm area with a resolution of 508 ppi, constituting the first electrode group.

[0509] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water and baked at 200°C for 1 hour.

[0510] Then, about 1 × 10 -4 The substrate was introduced into a vacuum deposition apparatus whose internal pressure had been reduced to 100 Pa, and after vacuum baking at 170° C. for 30 minutes in a heating chamber within the vacuum deposition apparatus, the substrate was allowed to cool for approximately 30 minutes.

[0511] Next, the substrate was fixed to a holder installed in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed faced downward, and N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBBiF) represented by the above structural formula (i) and a material (OCHD-003) having a molecular weight of 672 and electron acceptor properties, which contained fluorine, were co-deposited on the first electrode 101 by a deposition method at a weight ratio of 1:0.03 (= PCBBiF:OCHD-003) to a film thickness of 10 nm, thereby forming a hole injection layer 111.

[0512] On the hole injection layer 111, PCBBiF was evaporated to a film thickness of 110 nm to form a first hole transport layer.

[0513] Subsequently, on the first hole transport layer, 8-(p-terphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8mpTP-4mDBtPBfpm) represented by the above structural formula (ii), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: βNCCP) represented by the above structural formula (iii), and [2-d3-methyl-8-( The first light-emitting layer was formed by co-evaporation of [2-pyridinyl-κN]benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)) and [8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)] in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) to a thickness of 40 nm.

[0514] After this, 2-{3-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq) represented by the above structural formula (v) was evaporated to a film thickness of 10 nm to form a first electron transport layer.

[0515] After the formation of the first electron transport layer, 2,2'-([2,2'-bipyridine]-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 6,6'(P-Bqn)2BPy) represented by the above structural formula (vi), 4-(3,4-diphenyl-1-pyrrolidinyl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: Hid-DPPrdPhen) represented by the above structural formula (vii), and lithium oxide (LiO) were mixed. The first layer was formed by co-depositing the above compounds in a volume ratio of 0.5:0.5:0.02 (=6,6'(P-Bqn)BPy:Hid-DPPrdPhen:LiO) to a thickness of 5 nm, and the third layer was formed by co-depositing copper phthalocyanine (abbreviation: CuPc) represented by the above structural formula (viii) to a thickness of 2 nm. Furthermore, the second layer was formed by co-depositing PCBBiF and OCHD-003 in a weight ratio of 1:0.15 (=PCBBiF:OCHD-003) to a thickness of 10 nm, and an intermediate layer was formed.

[0516] On the intermediate layer, PCBBiF was evaporated to a thickness of 50 nm to form a second hole transport layer.

[0517] A second light-emitting layer was formed on the second hole-transporting layer by co-deposition of 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d3)2(mbfpypy-d3) in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) to a thickness of 40 nm.

[0518] Then, 2mPCCzPDBq was deposited to a thickness of 20 nm, and then 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P) represented by the above structural formula (ix) was deposited to a thickness of 20 nm to form a second electron transport layer.

[0519] Subsequently, tris(8-quinolinolato)aluminum (abbreviation: Alq3) was evaporated to a thickness of 10 nm to form a first protective layer.

[0520] After this, the substrate on which the first protective layer had been formed was removed from the vacuum deposition apparatus and exposed to the atmosphere. Then, using trimethylaluminum (abbreviation: TMA) as a precursor and water vapor as an oxidizing agent, an aluminum oxide film was formed by the ALD method to a thickness of 30 nm, forming the aluminum oxide film as the second protective layer.

[0521] A molybdenum film having a thickness of 50 nm was formed on the second protective layer by sputtering to form a third protective layer.

[0522] A photoresist was applied onto the third protective layer, and then exposed and developed to correspond to each of the multiple first electrodes, and each electrode was made independent, resulting in a resolution of 508 ppi.

[0523] Using the photoresist as a mask, the third protective layer was processed using an etching gas containing SF6 and oxygen (O2), and the processed third protective layer was used as a hard mask to process the second protective layer using an etching gas containing fluoroform (CHF3) and helium (He).Then, the hole injection layer, first hole transport layer, first emissive layer, first electron transport layer, intermediate layer, second hole transport layer, second emissive layer, and second electron transport layer were processed using an etching gas containing oxygen (O2).

[0524] After processing the organic compound layer, the third protective layer was removed using an etching gas containing SF6 and oxygen (O2), leaving the second protective layer. Then, an aluminum oxide film was deposited by ALD to a thickness of 15 nm to form a fourth protective layer.

[0525] Next, a photosensitive polymer material was formed on the first electrode on the fourth protective layer using photolithography. After heating at 100°C for 10 minutes in an air atmosphere, unnecessary portions of the first protective layer, second protective layer, and fourth protective layer were removed using a mixed acid solution containing hydrofluoric acid (HF), exposing the second electron transport layer. In this process, the photosensitive polymer material functions as a resist.

[0526] The substrate with the second electron transport layer exposed was then heated to 1×10 -4 The mixture was introduced into a vacuum deposition apparatus whose internal pressure had been reduced to about Pa, and then vacuum-baked at 100°C for 60 minutes in a heating chamber within the vacuum deposition apparatus.

[0527] Then, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited at a volume ratio of 1:0.5 (=LiF:Yb) to a film thickness of 1.5 nm to form an electron injection layer, and then silver (Ag) and magnesium (Mg) were co-deposited at a volume ratio of 1:0.1 to a film thickness of 15 nm to form a second electrode 102. In addition, 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) represented by the above structural formula (x) was deposited on the second electrode 102 as a cap layer at a film thickness of 70 nm to improve light extraction efficiency.

[0528] Next, in a glove box with a nitrogen atmosphere, the light-emitting device was sealed with a glass substrate to prevent it from being exposed to the atmosphere (a UV-curable sealant was applied around the element, UV was irradiated only onto the sealant without irradiating the light-emitting device, and heat treatment was performed at 80°C under atmospheric pressure for 1 hour), thereby forming light-emitting device 2-1.

[0529] (Method for fabricating light-emitting device 2-2) Light-emitting device 2-2 was fabricated in the same manner as light-emitting device 2-1, except that Hid-DPPrdPhen used in the first layer of light-emitting device 2-1 was replaced with 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-[3-(1-naphthyl)-1-pyrrolidinyl]-1,10-phenanthroline (abbreviation: Hid-αNPrdPhen) represented by the above structural formula (xi).

[0530] (Method for producing comparative light-emitting device 2) Comparative light-emitting device 2 was fabricated in the same manner as light-emitting device 2-1, except that Hid-DPPrdPhen used in the first layer in light-emitting device 2-1 was replaced with 4,7-di(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: Hid2Phen) represented by the above structural formula (xii).

[0531] The device structures of light-emitting device 2-1, light-emitting device 2-2, and comparative light-emitting device 2 are shown below.

[0532] [Table 4]

[0533] [Table 5]

[0534] The luminance-current density characteristics of light-emitting device 2-1, light-emitting device 2-2, and comparative light-emitting device 2 are shown in Figure 28, their current efficiency-luminance characteristics in Figure 29, their luminance-voltage characteristics in Figure 30, their current density-voltage characteristics in Figure 31, and their electroluminescence spectra in Figure 32. In addition, the luminance of light-emitting device 2-1, light-emitting device 2-2, and comparative light-emitting device 2 was 1000 cd / m 2 The main characteristics in this region are shown in Table 6. The luminance, CIE chromaticity, and electroluminescence spectrum were measured using a spectroradiometer (SR-UL1R, manufactured by Topcon Corporation) at room temperature.

[0535] [Table 6]

[0536] 28 to 32 and Table 6 show that all of the devices exhibited high current efficiency and functioned as tandem light-emitting devices, despite having undergone photolithography processing involving exposure to air during the formation of the light-emitting devices.

[0537] From the above results, it was found that the light-emitting device in which the organic compound represented by general formula (G1) in embodiment 1 is used in the first layer of the tandem light-emitting device has good characteristics even when processed by photolithography. [Example]

[0538] Synthesis Example 11 Example 1 This example describes a synthesis method for 4-(4-azatricyclo[5.2.2.0,2,6]undecan-4-yl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: Hid-AcuPhen) represented by structural formula (122) in Embodiment 1. The structure of Hid-AcuPhen is shown below.

[0539] [ka]

[0540] A 50 mL three-neck flask was charged with 1.00 g (2.96 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 0.69 g (3.68 mmol) of 4-azatricyclo[5.2.2.0,2,6]undecane hydrochloride, and 2.00 g (13.1 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU). The mixture was stirred at 100 °C for 32 hours under a nitrogen atmosphere. After stirring, the mixture was allowed to cool to room temperature. Water was added to the mixture, followed by extraction with dichloromethane. The extract was concentrated to obtain the crude product (1.07 g). The synthetic scheme for this synthesis example is shown in formula (s11-1) below.

[0541] [ka]

[0542] Synthesized Hid-AcuPhen 1 The HNMR spectra are shown in Figures 33(A) to 33(C). Note that Figure 33(B) is a graph showing an enlarged view of the range from 6.5 ppm to 9.0 ppm in Figure 33(A), and Figure 33(C) is a graph showing an enlarged view of the range from 1.0 ppm to 4.0 ppm. 1 The results of HNMR measurement are shown below, and it was confirmed that Hid-AcuPhen was obtained.

[0543] 1 H-NMR (500MHz, CHLOROFORM-D): δ=8.85(d,J=5.3Hz,1H),8.72(d,J=5.4Hz,1H),8.08(d,J=9.6Hz,1H),7.93(d,J=9.7Hz,1H),6.92(d,J=5.3Hz,1H),6.67 (d,J=5.4Hz,1H),3.75-3.64(m,4H),3.54-3.48(m,4H),2.54-2.48(m,2H),2 .41-2.35(m,2H),1.99-1.89(m,2H),1.74-1.53(m,12H),1.49-1.39(m,4H). [Example]

[0544] Synthesis Example 12 Example 1 This example describes a synthesis method for 4-(4-azatricyclo[5.2.1.0,2,6]decan-4-yl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviation: Hid-AccPhen), an organic compound of one embodiment of the present invention. The structure of Hid-AccPhen is shown below.

[0545] [ka]

[0546] A 50 mL three-neck flask was charged with 1.0 g (3.0 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 0.64 g (3.7 mmol) of 4-azatricyclo[5.2.1.0,2,6]decane hydrochloride, and 1.1 g (7.2 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene (abbreviation: DBU), and the mixture was stirred at 100 °C for 8 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. Water was added to the mixture, and the mixture was extracted with dichloromethane. The extract was concentrated to obtain the desired product. The synthesis scheme for Hid-AccPhen is shown in formula (s12-1) below.

[0547] [ka]

[0548] The mass of the target product was measured using GC-MS. As a result, a signal at m / z 438 was observed, which corresponds to the calculated mass of the target product of 438. This indicated that 4-(4-azatricyclo[5.2.1.0,2,6]decan-4-yl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline was obtained.

[0549] The GC-MS analysis was performed using a Thermo Fisher Scientific DEP-ISQ7610 instrument, with MS analysis (mass spectrometry) performed using the DEP (Direct Exposure Probe) method. The ion source temperature was set to 200°C. The initial probe current was set to 0 mA and held for 30 seconds. After that, the probe current was increased to 800 mA at a rate of 20 mA / s for 30 seconds. [Explanation of symbols]

[0550] 100A display device 100B display device 100C display device 100E display device 100D display device 100 Insulator 101 first electrode 102 second electrode 103 Organic compound layer 104 Common layer 110B subpixel 110G subpixel 110R subpixel 110 subpixels 111 Hole injection layer 112 Hole transport layer 112B Conductive layer 112R conductive layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 116 Charge generation layer 117 Second Layer 118 Third Layer 119 First Layer 120 boards 122 Resin layer 125 Inorganic insulating layer 126R conductive layer 126B Conductive layer 127 Insulating Layer 128 layers 129R conductive layer 129B Conductive layer 130B Light-emitting devices 130G Light Emitting Device 130R Light Emitting Device 130 Light-emitting devices 131 Protective layer 132B Colored layer 132G colored layer 132R colored layer 135 First Layer 135A First Group 135R First layer 135G 1st layer 135B First Layer 140 Connection 141 areas 142 Adhesive layer 151B Conductive layer 151C conductive layer 151G conductive layer 151R conductive layer 151 Conductive layer 152B Conductive layer 152C conductive layer 152G Conductive layer 152R Conductive layer 152 Conductive layer 153 Insulating Layer 156B Insulating layer 156C Insulation layer 156G Insulation layer 156R Insulation layer 157 Light blocking layer 158B Sacrificial Layer 158G Sacrificial Layer 158R Sacrificial Layer 166 Conductive Layer 171 Insulating layer 172 Conductive layer 173 Insulating Layer 174 Insulating Layer 175 Insulating Layer 176 Plug 177 Pixel section 178 pixels 201 Transistor 204 Connection 205 Transistor 211 Insulating layer 213 Insulating Layer 214 Insulating layer 215 Insulating Layer 221 Conductive layer 222a conductive layer 222b Conductive layer 223 Conductive Layer 224B Conductive layer 224C conductive layer 224G conductive layer 224R conductive layer 231 Semiconductor layer 240 capacity 241 Conductive Layer 242 Connection Layer 243 Insulating Layer 245 Conductive Layer 254 Insulating Layer 255 insulating layer 256 plug 261 Insulating Layer 271 Plug 280 Display Module 281 Display section 282 Circuit section 283a Pixel circuit 283 Pixel circuit section 284a pixels 284 pixel section 285 Terminal section 286 Wiring section 290 FPC 291 Circuit Board 292 PCB 301 Substrate 310 Transistor 311 Conductive layer 312 Low resistance region 313 Insulating Layer 314 Insulating Layer 315 Element isolation layer 351 Circuit Board 352 Circuit Board 353 FPC 354 IC 355 Wiring 356 circuits 501 first electrode 502 Second electrode 503 Organic compound layer 513 Middle Class 700A electronic equipment 700B Electronic equipment 721 Case 723 Mounting part 727 Earphones 750 earphones 751 Display Panel 753 Optical Components 756 Display area 757 frames 758 Nose pad 800A electronic equipment 800B Electronic equipment 820 Display section 821 Case 822 Communications Department 823 Mounting part 824 Control Unit 825 Imaging unit 827 Earphones 832 Lens 6500 Electronic equipment 6501 Housing 6502 Display section 6503 Power button 6504 Button 6505 Speaker 6506 Microphone 6507 Camera 6508 Light source 6510 Protective materials 6511 Display Panel 6512 Optical components 6513 Touch Sensor Panel 6515 FPC 6516 IC 6517 Printed Circuit Board 6518 Battery 7000 Display 7100 Television equipment 7151 Remote Controlled Machine 7171 Case 7173 Stand 7200 Notebook Personal Computer 7211 Case 7212 keyboard 7213 Pointing Device 7214 External connection port 7300 Digital Signage 7301 Housing 7303 Speaker 7311 Information terminals 7400 Digital Signage 7401 Pillar 7411 Information terminals 9000 chassis 9001 Display section 9002 Camera 9003 Speaker 9005 Operation key 9006 Connection terminal 9007 Sensor 9008 Microphone 9050 Icon 9051 Information 9052 Information 9053 Information 9054 Information 9055 Hinge 9171 Mobile Information Terminal 9172 Mobile Information Terminal 9173 Tablet Devices 9200 Mobile Information Terminal 9201 Mobile Information Terminal

Claims

1. An organic compound represented by general formula (G1) or general formula (G2): 【Chemistry 1】 (In the above general formula (G1) or general formula (G2), X ２ ~X ５ or X ６ ~X ９ One of R represents a halogen or a trifluoromethanesulfonyl group, and the rest represent hydrogen. ２ ~R ５ or R ６ ~R ９ one of which represents an aliphatic cyclic amino group represented by the following general formula (g1), and the rest represent hydrogen, provided that the position of the carbon substituted with a halogen or trifluoromethanesulfonyl group and the position of the carbon substituted with a group represented by the following general formula (g1) are positioned in line symmetry in the main skeleton (1,10-phenanthroline skeleton or 2,2'-bipyridine skeleton). 【Chemistry 2】 (In the above general formula (g1), R １１ ~R １８ each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amide group, and a carbonyl group, and p and q each independently represent 0 to 3. １１ ~R １８ Any two of may be bonded to each other to form a ring.)

2. An organic compound represented by any one of general formulas (G1-1) to (G1-4): 【Transformation 3】 (In the above general formulae (G1-1) to (G1-4), X represents a halogen or a trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the following general formula (g1).) 【Chemistry 4】 (In the above general formula (g1), R １１ ~R １８ each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amide group, and a carbonyl group, and p and q each independently represent 0 to 3. １１ ~R １８ Any two of may be bonded to each other to form a ring.)

3. An organic compound represented by any one of general formulas (G2-1) to (G2-4): 【Transformation 5】 (In the above general formulae (G2-1) to (G2-4), X represents a halogen or a trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the following general formula (g1).) 【Transformation 6】 (In the above general formula (g1), R １１ ~R １８ each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amide group, and a carbonyl group, and p and q each independently represent 0 to 3. １１ ~R １８ Any two of may be bonded to each other to form a ring.)

4. An organic compound represented by general formula (G3): 【Transformation 7】 (In the above general formula (G3), R is a group represented by the following general formula (g1), and A is a group represented by the following general formula (g2) or (g3). In addition, in the general formula (G3), the substituent A and the substituent R are different substituents.) 【Transformation 8】 (In the above general formulas (g1) and (g2), R １１ ~R １８ , R ２１ ~R ２８ each independently represents hydrogen (including deuterium) or any one of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amide group, and a carbonyl group, and p, q, s, and t each independently represent 0 to 3. １１ ~R １８ Any two of the above, and R ２１ ~R ２８ Any two of these may be bonded to each other to form a ring. Furthermore, the aliphatic cyclic amino group represented by the general formula (g2) may be condensed with an aromatic ring having 6 to 10 carbon atoms. In the general formula (g3), Z represents any one of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted monovalent heteroaromatic ring group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amide group, or a carbonyl group, and m represents an integer of 1 to 3. When m is 2 or greater, the multiple Zs may be the same or different groups. Furthermore, L represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, and n represents an integer of 0 to 3. Note that when n is 2 or more, a plurality of Ls may be the same group or different groups.

5. An organic compound represented by general formula (G3-1): 【Chemistry 9】 (In the above general formula (G3-1), R １１ ~R １８ and R ２１ ~R ２８ each independently represents any one of hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amide group, and a carbonyl group, and p, q, s, and t each independently represent 0 to 3. １１ ~R １８ Any two of the above, and R ２１ ~R ２８ Any two of the above may be bonded to each other to form a ring. In addition, one of the aliphatic cyclic amino groups in the general formula (G3-1) may be condensed with an aromatic ring having 6 to 10 carbon atoms. In addition, in the general formula (G3-1), the substituents bonded to the 1,10-phenanthroline skeleton and the 4- and 7-positions are different from each other.

6. An organic compound represented by general formula (G3-2): 【Chemistry 10】 (In the above general formula (G3-2), R １１ ~R １８ each independently represents any one of hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amide group, and a carbonyl group, and p and q each independently represent 0 to 3. １１ ~R １８ Any two of these may be bonded to each other to form a ring. Z represents any one of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted monovalent heteroaromatic ring group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms, a cyano group, a halogen atom, a hydroxy group, an amide group, or a carbonyl group, and m represents an integer of 1 to 3. When m is 2 or more, the multiple Zs may be the same or different groups. Furthermore, L represents a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, and n represents an integer of 0 to 3. Note that when n is 2 or more, a plurality of Ls may be the same group or different groups.

7. A method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having substituents at two symmetrical carbon atoms, each of which has a halogen or a trifluoromethanesulfonyl group, on two symmetrical carbon atoms, and an aliphatic cyclic amine, using an inorganic base and a solvent.

8. A method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having substituents on two symmetric carbon atoms, each of which has a halogen or a trifluoromethanesulfonyl group, and an aliphatic cyclic amine, using potassium carbonate or potassium acetate as a solvent, to cause the derivative to react with each other.

9. A method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having a substituent at each of two symmetrical carbon atoms, each of which is different from the other, comprising: a first step of reacting a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having a halogen or a trifluoromethanesulfonyl group at two symmetrical carbon atoms with an aliphatic cyclic amine using potassium carbonate or potassium acetate as a solvent to obtain a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative in which the aliphatic cyclic amine is bonded to the carbon to which one of the two halogens or trifluoromethanesulfonyl groups is bonded; and a second step of introducing another substituent to the carbon to which the other of the two halogens or trifluoromethanesulfonyl groups is bonded.

10. In any one of claims 7 to 9, The method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative, which has substituents at two symmetrical carbon atoms, each of which is different from the other, uses N-methyl-2-pyrrolidone as the solvent.

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