Capping layer material, organic electroluminescent element, and amine compound

Abstract

Provided are a novel capping layer material for an organic thin film element; a novel organic electroluminescent element; and a novel amine compound.　The amine compound is represented by formula (2).　In formula (2), A moieties are each independently: a trivalent to tetravalent monocyclic, linked ring or condensed ring aromatic hydrocarbon group having 6-13 carbon atoms, which may be substituted with a fluorine atom; a trivalent to tetravalent monocyclic, linked ring or condensed ring heteroaromatic group having 3-11 carbon atoms, which may be substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group or a fluorine atom; or a trivalent to tetravalent cyclic aliphatic hydrocarbon group having 3-18 carbon atoms, which may be substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group or a fluorine atom.　In formula (2), B moieties are each independently: a divalent to trivalent monocyclic, linked ring or condensed ring aromatic hydrocarbon group having 6-13 carbon atoms; a divalent to trivalent monocyclic, linked ring or condensed ring heteroaromatic group having 3-11 carbon atoms; or a divalent to trivalent cyclic aliphatic hydrocarbon group having 3-18 carbon atoms.　In formula (2), E moieties are each independently: a monovalent monocyclic, linked ring or condensed ring aromatic hydrocarbon group having 6-26 carbon atoms; a monovalent monocyclic, linked ring or condensed ring heteroaromatic group having 3-26 carbon atoms; or a monovalent cyclic aliphatic hydrocarbon group having 3-18 carbon atoms.　In formula (2), l is an integer between 1 and 4.　In formula (2), m is an integer between 0 and 2.　In formula (2), n is 1 or 2.　In formula (2), at least one E moiety is a moiety in which an aromatic hydrocarbon group, heteroaromatic group or aliphatic hydrocarbon group that constitutes E is substituted with one or more fluorine atoms.　In formula (2), B and E moieties may each independently be substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group or a fluorine atom, and substituent groups on B and E moieties may be further substituted with one or more groups selected from the group consisting of these groups.

Description

Capping layer material, organic electroluminescence device, amine compound

[0001] The present disclosure relates to a capping layer material, an organic electroluminescent device, and an amine compound.

[0002] In recent years, organic thin-film devices such as organic electroluminescence (EL), organic thin-film solar cells, organic transistors, and organic sensors have been widely developed. In such organic thin-film devices, when light emitted from the light-emitting portion enters another film at an angle greater than a certain value, it is totally reflected at the interface between the light-emitting portion and the other film. As a result, only a portion of the emitted light can be utilized. In organic thin-film devices, in order to improve device efficiency, it is necessary to improve the light extraction efficiency by using a capping layer. In particular, in recent years, the extraction efficiency has been improved by stacking two or more layers of materials with different refractive indices (i.e., high and low refractive indexes) on the capping layer.

[0003] As materials used in the capping layer (capping layer materials), Patent Document 1 discloses inorganic materials such as silicon oxide and magnesium fluoride.

[0004] However, since the material disclosed in Patent Document 1 is an inorganic material, it is difficult to control the film thickness by vacuum deposition, making it difficult to improve the light extraction efficiency. In addition, the high deposition temperature may adversely affect the surrounding organic material layers.

[0005] Japanese Patent Application Publication No. 2018-139262

[0006] Therefore, one aspect of the present disclosure is directed to providing a novel capping layer material for an organic thin film device, a novel organic electroluminescent device, and a novel amine compound.

[0007] As a result of extensive research into solving the above problems, the present inventors have discovered a novel capping layer material for an organic thin-film device, a novel organic electroluminescence device, and a novel amine compound, thereby completing the present invention.

[0008] That is, the present disclosure includes the following embodiments.

[0009] [1] An amine compound represented by the following formula (2):

[0010]

[0011] In formula (2), each A independently represents a monocyclic, linked, or fused ring tri- or tetravalent aromatic hydrocarbon group having 6 to 13 carbon atoms which may be substituted with a fluorine atom; a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a monocyclic, linked, or fused ring tri- or tetravalent heteroaromatic group having 3 to 11 carbon atoms which may be substituted with a fluorine atom; or a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a cyclic tri- or tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted with a fluorine atom.

[0012] In formula (2), each B independently represents a divalent or trivalent aromatic hydrocarbon group having 6 to 13 carbon atoms, a divalent or trivalent monocyclic, linked ring, or fused ring aromatic group having 3 to 11 carbon atoms, or a divalent or trivalent aliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0013] In formula (2), each E independently represents a monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, a monovalent heteroaromatic group having 3 to 26 carbon atoms, a monovalent heteroaromatic group having 3 to 26 carbon atoms, or a cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0014] In formula (2), l represents an integer of 1 to 4.

[0015] In formula (2), m represents an integer of 0 to 2.

[0016] In formula (2), n represents 1 or 2.

[0017] In formula (2), at least one E is an aromatic hydrocarbon group, a heteroaromatic group, or an aliphatic hydrocarbon group that constitutes E, and is substituted with one or more fluorine atoms.

[0018] In formula (2), B and E may each independently be substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom, or the substituents of B and E may be further substituted with one or more groups selected from the group consisting of these groups.

[0019] [2] The amine compound according to [1] above, wherein the compounds A in the formula (2) that provide a monocyclic, linked, or fused ring trivalent or tetravalent aromatic hydrocarbon group having 6 to 13 carbon atoms are each independently: (A1) benzene, biphenyl, naphthalene, or fluorene; or (A1') the compound represented by (A1) substituted with one or more fluorine atom groups.

[0020] [3] In the above formula (2), the compounds which provide a monocyclic, linked, or fused trivalent to tetravalent heteroaromatic group having 3 to 11 carbon atoms, represented by A, are each independently: (A5) pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole; or (A5') the compound represented by (A5) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom, according to the above [1].

[0021] [4] The amine compound according to [1] above, wherein the compounds which provide the cyclic trivalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by A in the above formula (2), are each independently: (A10) adamantane, diamantane, norbornene, or cyclohexane; or (A10') the compound represented by (A10) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom.

[0022] [5] The amine compound according to any one of [1] to [4] above, wherein the compounds which provide a monocyclic, linked ring, or fused ring divalent or trivalent aromatic hydrocarbon group having 6 to 13 carbon atoms, represented by B in the above formula (2), are each independently: (B1) benzene, biphenyl, naphthalene, or fluorene; or (B1') the compound represented by (B1) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents possessed by the compound represented by (B1) may be further substituted with one or more groups selected from the group consisting of the above groups).

[0023] [6] In the above formula (2), the compounds which provide a monocyclic, linked ring, or fused ring divalent or trivalent heteroaromatic group having 3 to 11 carbon atoms, represented by B, are each independently selected from the following: (B5) pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole; (B5') The compound represented by (B5) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituent possessed by the compound represented by (B5) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), according to any one of the above-mentioned [1] to [4].

[0024] [7] The amine compound according to any one of the above [1] to [4], wherein the compounds which provide a cyclic divalent or trivalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by B in the above formula (2), are each independently: (B10) adamantane, diamantane, norbornene, or cyclohexane; or (B10') the compound represented by (B10) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents possessed by the compound represented by (B10) may be further substituted with one or more groups selected from the group consisting of the above groups).

[0025] [8] In the above formula (2), the compounds which provide a monovalent aromatic hydrocarbon group of 6 to 26 carbon atoms, represented by E, are each independently selected from the following: (E1) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or a structure in which these compounds are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; or (E1') The amine compound according to any one of the above [1] to [7], wherein the compound represented by (E1) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituent possessed by the compound represented by (E1) may be further substituted with one or more groups selected from the group consisting of the above groups).

[0026] [9] In the above formula (2), the compounds which provide a monocyclic, linked, or fused monovalent heteroaromatic group having 6 to 26 carbon atoms, represented by E, are each independently selected from the following: (E8) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or a structure in which one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these compounds; or (E8') The compound represented by (E8) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituent possessed by the compound represented by (E8) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), according to any one of the above-mentioned [1] to [7].

[0027]

[10] The amine compound according to any one of the above [1] to [7], wherein the compounds which provide a cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by E in the above formula (2), are each independently: (E14) adamantane, diamantane, norbornene, or cyclohexane; or (E14') the compound represented by (E14) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents possessed by the compound represented by (E14) may be further substituted with one or more groups selected from the group consisting of the above groups).

[0028]

[11] A capping layer material for an organic thin film element, comprising at least one compound selected from the group consisting of a compound represented by the following formula (1) and the amine compound described in any one of [1] to [9] above:

[0029]

[0030] In formula (1), each X independently represents an optionally substituted tri- to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; an optionally substituted tri- to tetravalent heteroaromatic group having 3 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; or an optionally substituted cyclic tri- to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0031] In formula (1), each Y independently represents an optionally substituted di- or trivalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; an optionally substituted di- or trivalent monocyclic, linked ring, or fused ring aromatic group having 3 to 26 carbon atoms, which is a heteroaromatic group having 2 or 3 heteroatoms; or an optionally substituted cyclic di- or trivalent aliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0032] In formula (1), each Z independently represents an optionally substituted monovalent aromatic hydrocarbon group of 6 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; an optionally substituted monovalent heteroaromatic group of 3 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; or an optionally substituted cyclic monovalent aliphatic hydrocarbon group of 3 to 18 carbon atoms.

[0033] In formula (1), a represents an integer of 1 to 4.

[0034] In formula (1), b represents an integer of 0 to 2.

[0035] In formula (1), c represents 1 or 2.

[0036] In formula (1), at least one E is substituted with a fluorine atom.

[0037]

[12] The capping layer material according to the above

[11] , wherein the organic thin film element is an organic electroluminescence element.

[0038]

[13] An organic electroluminescence device having at least an anode, an emitting layer, a cathode, and a capping layer in this order, wherein the capping layer contains the capping layer material according to

[11] above or the amine compound according to any one of [1] to [9] above.

[0039]

[14] An organic electroluminescence device having at least an anode, an emitting layer, a cathode, and a capping layer in this order, the capping layer being composed of at least a high refractive index layer and a low refractive index layer, and the low refractive index layer containing the capping layer material according to the above

[11] or the amine compound according to any one of the above [1] to [9].

[0040] According to one aspect of the present disclosure, there are provided a novel capping layer material for an organic thin film device, a novel organic electroluminescent device including the capping layer material, and a novel amine compound.

[0041] Fig. 1 is a schematic cross-sectional view showing an example of the configuration of an organic electroluminescence element according to the present disclosure. Fig. 2 is a schematic cross-sectional view showing an example of the configuration of an organic electroluminescence element according to the present disclosure. Fig. 3 is a view showing the results of refractive index measurement for compound (A010). Fig. 4 is a view showing the results of transmittance measurement for compound (A010). Fig. 5 is a view showing the results of refractive index measurement for compound (X1). Fig. 6 is a schematic cross-sectional view showing an example of the configuration of an organic electroluminescence element according to the present disclosure.

[0042] Hereinafter, the capping layer material, the organic electroluminescence device, and the amine compound according to one embodiment of the present disclosure will be described in detail.

[0043] [Capping layer material for organic thin film device] A capping layer material for an organic thin film device according to one embodiment of the present disclosure includes at least one compound selected from the group consisting of a compound represented by formula (1) described below and an amine compound represented by formula (2) described below.

[0044] [Substrate] Examples of the substrate on which the thin film of the capping layer material is formed include substrates made of metal, glass, ceramic, organic polymer, etc. As these substrates, substrates having a shape such as a plate, cylinder, sphere, rod, block, plate, convex lens, concave lens, etc., and further substrates having a fine structure on the surface on the order of nanometers to micrometers can be used.

[0045] The method for forming and processing the substrate is not particularly limited and any known method can be used. Furthermore, a transparent conductive film, metal wiring, etc. may be provided on the surface of the substrate.

[0046] In the present disclosure, in order to improve adhesion to the thin film of the capping layer material, the substrate surface may be subjected to a surface treatment in advance before forming the thin film of the capping layer material. Examples of the surface treatment include known methods such as surface treatment with a silane coupling agent or a primer treatment agent, oxidation treatment with an acid such as sulfuric acid or hydrofluoric acid or ozone, surface treatment with plasma, photocleaning treatment with UV light, polishing with an abrasive, and physical cleaning treatment such as buffing or wet blasting. Only one of the above surface treatments may be used, or two or more may be used in combination.

[0047] Furthermore, a thin film made of one or more organic and inorganic materials other than the capping layer material may be formed between the substrate and the capping layer material.

[0048] [Film formation] As a film formation method of the capping layer material, known methods such as vacuum deposition, spin coating, casting, dip coating, die coating, bar code coating, offset coating, spray coating, inkjet coating, screen coating, offset coating, flexography, gravure coating, and microcontact coating can be applied. After the film formation of the capping layer material, the film may be annealed in a temperature environment higher than room temperature. There are no particular restrictions on the film thickness of the organic material pattern. From the viewpoint of forming a uniform amorphous film, vacuum deposition is preferred as the film formation method.

[0049] [Vacuum Vapor Deposition Method] The capping layer material can be formed into a film by vacuum vapor deposition, which allows the formation of a uniform thin film.

[0050] Vacuum deposition methods can be further divided into resistance heating, electron beam heating, high-frequency induction heating, reactive vapor deposition, molecular beam epitaxy, hot wall deposition, ion plating, cluster ion beam deposition, etc. Any of these methods can be used to form a film of the capping layer material. From the viewpoints of suppressing decomposition of the capping layer material and simplifying the equipment, resistance heating and high-frequency induction heating are preferred, and resistance heating is more preferred.

[0051] The conditions for forming the thin film vary depending on the type of vacuum deposition method. In the case of the resistance heating method, the degree of vacuum is 1 x 10 －３ Pa or less, and more preferably 1×10 －４ Pa or less.

[0052] The heating temperature of the vapor deposition source is not particularly limited as long as it is a temperature at which the capping layer material does not decompose and the capping layer material vapor deposition source has sufficient vapor pressure. Specifically, 100°C to 400°C is preferred. If the heating temperature is close to the decomposition temperature of the capping layer material, the performance of the capping layer material-containing thin film may be reduced. Therefore, the difference between the vapor deposition temperature and the decomposition temperature is preferably 20°C or more, more preferably 30°C or more, even more preferably 40°C or more, and even more preferably 50°C or more.

[0053] During vacuum deposition, the substrate temperature is preferably in the range of room temperature to 200° C. If the substrate temperature exceeds 200° C., problems may occur, such as limitations on the materials that can be used for the substrate, a decrease in the film formation rate, and thermal expansion of the substrate, which may cause defects such as wrinkles and crystallization in the substrate and the thin film of the capping layer material during cooling. The substrate temperature is more preferably 150° C. or less, and even more preferably 100° C. or less.

[0054] In the present disclosure, after forming a thin film of the capping layer material, an annealing treatment is performed as necessary. The annealing conditions vary depending on the type of substrate, the type of capping layer material, and the type of functional group, but it is preferably performed in an inert gas or air atmosphere at 50°C or higher and 200°C or lower. By setting the annealing temperature to 50°C or higher, a sufficient annealing effect can be obtained. On the other hand, if the annealing temperature exceeds 200°C, the thin film may soften, resulting in a loss of flatness.

[0055] [Transparency] The thin film of the capping layer material preferably has a transmittance of 90% or more, 91% or more, 92% or more, 93% or more, 94% or more, or 95% or more in the range of 450 nm to 900 nm.

[0056] [Refractive Index] The thin film of the capping layer material preferably has a refractive index of less than 1.70, less than 1.69, less than 1.68, less than 1.67, less than 1.66, less than 1.65, less than 1.64, less than 1.63, less than 1.62, less than 1.61, less than 1.60, less than 1.59, less than 1.58, less than 1.57, less than 1.56, or less than 1.55 in the range of 450 nm to 900 nm.

[0057] [Glass Transition Temperature] The capping layer material preferably has a glass transition temperature of 60°C or higher, 70°C or higher, 80°C or higher, 90°C or higher, or 100°C or higher, from the viewpoint of rigidifying the molecules and increasing the thermal stability of the thin film.

[0058] [Organic Electroluminescence Device] An organic electroluminescence device according to one embodiment of the present disclosure has at least an anode, an emitting layer, a cathode, and a capping layer in this order, and the capping layer contains the above-described capping layer material or the above-described amine compound.

[0059] [Capping Layer] The capping layer contains the above-described capping layer material or the above-described amine compound. In addition to the capping layer material or the amine compound, the capping layer may optionally contain other organic molecules, inorganic molecules, polymers, etc., as long as the performance of the capping layer is not impaired.

[0060] The thickness of the capping layer is not particularly limited, but is preferably 30 nm to 500 nm, 30 nm to 400 nm, 30 nm to 350 nm, 30 nm to 300 nm, 40 nm to 250 nm, 50 nm to 250 nm, or 60 nm to 200 nm.

[0061] The capping layer may have a laminated structure including a plurality of layers. When the capping layer has a laminated structure, the number of layers is not particularly limited, but is preferably 2 to 6, 2 to 5, 2 to 4, or 2 to 3, and more preferably 2 types of layers.

[0062] When the capping layer is formed of a laminated structure, at least one layer forming the laminated structure is a low refractive index layer. It is also preferable that at least one layer is a high refractive index layer. That is, an organic electroluminescence element is preferred that has at least an anode, an emitting layer, a cathode, and a capping layer in this order, the capping layer is composed of at least a high refractive index layer and a low refractive index layer, and the low refractive index layer contains the above-mentioned capping layer material or an amine compound.

[0063] Examples of the laminate structure of the capping layer include the following structures (1) to (4): (1) high refractive index layer / low refractive index layer (2) low refractive index layer / high refractive index layer (3) low refractive index layer / high refractive index layer / low refractive index layer (4) high refractive index layer / medium refractive index layer / low refractive index layer.

[0064] Here, the relationship of the refractive indexes of the low refractive index layer, the medium refractive index layer, and the high refractive index layer in the range of 450 nm to 900 nm is low refractive index layer≦medium refractive index layer≦high refractive index layer.

[0065] [Low Refractive Index Layer] The low refractive index layer contains the above-mentioned capping layer material or the above-mentioned amine compound.

[0066] The thickness of the low refractive index layer is not particularly limited, but is preferably 20 nm to 200 nm, 20 nm to 160 nm, 20 nm to 140 nm, or 30 nm to 120 nm.

[0067] [High Refractive Index Layer] The high refractive index layer preferably has a light transmittance of 90% or more in the range of 450 nm to 900 nm and a refractive index of 1.70 or more.

[0068] The refractive index of the high refractive index layer is more preferably 1.71 or more, 1.72 or more, 1.73 or more, 1.74 or more, 1.75 or more, 1.76 or more, 1.77 or more, 1.78 or more, 1.79 or more, or 1.80 or more in the range of 450 nm to 900 nm.

[0069] The thickness of the high refractive index layer is not particularly limited, but is preferably 20 nm to 200 nm, 20 nm to 160 nm, 20 nm to 140 nm, or 30 nm to 120 nm.

[0070] [High refractive index material] The high refractive index layer contains a high refractive index material. The high refractive index material is not particularly limited as long as it exhibits the high refractive index described above, and an organic compound, an inorganic compound, a polymer compound, or the like can be used. Alternatively, the high refractive index material may be a mixture of an organic compound, an inorganic compound, and a polymer compound.

[0071] The high refractive index material preferably contains an organic compound, from the viewpoints that the film thickness can be easily controlled by a vacuum deposition method and the deposition temperature can be lowered.

[0072] Examples of the high refractive index material include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, carbazole compounds, styrylamine compounds, triazine derivatives, and pyrimidine derivatives, because of their excellent thin film stability and durability. Among these, carbazole compounds, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred because of their excellent durability, and carbazole compounds and aromatic tertiary amine compounds are particularly preferred.

[0073] [Medium Refractive Index Layer] The medium refractive index layer has a light transmittance of 90% or more in the range of 450 nm to 900 nm, and a refractive index of 1.60 or more.

[0074] The refractive index of the medium refractive index layer is preferably 1.61 or more, 1.61 or more, 1.62 or more, 1.63 or more, 1.64 or more, 1.65 or more, 1.66 or more, 1.67 or more, 1.68 or more, or 1.69 or more in the range of 450 nm to 900 nm.

[0075] The thickness of the medium refractive index layer is not particularly limited, but is preferably 20 nm to 200 nm, 20 nm to 160 nm, 20 nm to 140 nm, or 30 nm to 120 nm.

[0076] [Medium Refractive Index Material] The medium refractive index layer contains a medium refractive index material. The medium refractive index material is not particularly limited as long as it exhibits the medium refractive index described above, and an organic compound, an inorganic compound, a polymer compound, or the like can be used. Alternatively, the medium refractive index material may be a mixture of an organic compound, an inorganic compound, and a polymer compound.

[0077] The medium refractive index material preferably contains an organic compound, from the viewpoints of facilitating film thickness control by vacuum deposition and enabling a lower deposition temperature.

[0078] [Organic Electroluminescence Device] An organic electroluminescence device according to one aspect of the present disclosure has at least an anode, an emitting layer, a cathode, and a capping layer in this order, wherein the capping layer contains the capping layer material described above or the amine compound represented by formula (2) described below. The organic electroluminescence device preferably has at least an anode, an emitting layer, a cathode, and a capping layer in this order, wherein the capping layer is composed of at least a high-refractive index layer and a low-refractive index layer, wherein the low-refractive index layer contains the capping layer material described above or the amine compound represented by formula (2) described below.

[0079] [Overall Configuration of Organic Electroluminescence Device] The configuration of the organic electroluminescence device is not particularly limited, but examples thereof include the following configurations (i) to (vi).

[0080] (i) anode / light-emitting layer / cathode / capping layer (ii) anode / light-emitting layer / electron-injection layer / cathode / capping layer (iii) anode / hole-transporting layer / light-emitting layer / electron-injection layer / cathode / capping layer (iv) anode / light-emitting layer / electron-transporting layer / electron-injection layer / cathode / capping layer (v) anode / hole-transporting layer / light-emitting layer / electron-transporting layer / electron-injection layer / cathode / capping layer (vi) anode / hole-injection layer / hole-transporting layer / light-emitting layer / electron-transporting layer / electron-injection layer / cathode / capping layer.

[0081] Note that the configurations (i) to (vi) described above have a so-called top-emission type element configuration, but the organic electroluminescent element according to one embodiment of the present disclosure is not limited to the top-emission type element configuration. In other words, the organic electroluminescent element according to one embodiment of the present disclosure may have any other known element configuration.

[0082] FIG. 1 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescence element according to one embodiment of the present disclosure.

[0083] The organic electroluminescence device 100 includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8, and a capping layer 9, in this order. The capping layer 9 includes a high-refractive index layer 91 and a low-refractive index layer 92, in this order. However, some of these layers, except for the capping layer 9, may be omitted, or other layers may be added. For example, a hole blocking layer may be provided between the emitting layer 5 and the electron transport layer 6, or the hole injection layer 3 may be omitted and the hole transport layer 4 may be provided directly on the anode 2. For example, the electron transport layer 6 may be omitted and the electron injection layer 7 may be provided directly on the emitting layer 5. Furthermore, for example, the single-layer hole transport layer 4 and the single-layer electron transport layer 6 may each be composed of multiple layers.

[0084] [Substrate 1] Examples of the substrate 1 include a glass plate, a quartz plate, a plastic plate, and a plastic film. Among these, a glass plate, a quartz plate, and a light-transmitting plastic film are preferred.

[0085] Examples of the light-transmitting plastic film include films made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

[0086] In the case where light is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of the light.

[0087] [Anode 2] An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side).

[0088] Examples of materials for the anode 2 include metals, alloys, electrically conductive compounds, and mixtures thereof, each having a large work function (for example, 4 eV or more). Specific examples of materials for the anode 2 include metals such as Au, CuI, indium tin oxide (ITO), and SnO. ２, ZnO, and other conductive transparent materials.

[0089] In the case of an organic electroluminescent element having a configuration in which light emitted is extracted through the anode, the anode 2 is formed of a conductive transparent material that is transparent or substantially transparent to the light emitted.

[0090] [Hole Injection Layer 3, Hole Transport Layer 4] Between the anode 2 and the light-emitting layer 5 described below, the hole injection layer 3 and the hole transport layer 4 are provided in this order from the anode 2 side.

[0091] The hole injection layer 3 and the hole transport layer 4 have the function of transporting holes injected from the anode 2 to the light-emitting layer. By interposing the hole injection layer 3 and the hole transport layer 4 between the anode 2 and the light-emitting layer 5, a large number of holes can be injected into the light-emitting layer with a lower electric field.

[0092] The hole injection layer 3 and the hole transport layer 4 also function as electron barrier layers. That is, electrons injected from the cathode and transported from the electron injection layer 7 and / or the electron transport layer 6 to the light-emitting layer 5 are prevented from leaking to the hole injection layer 3 and / or the hole transport layer 4 by the electron barrier present at the interface between the light-emitting layer 5 and the hole injection layer 3 and / or the hole transport layer 4. As a result, the electrons accumulate at the interface within the light-emitting layer 5, which brings about effects such as improved light-emitting efficiency, and an organic electroluminescence device with excellent light-emitting performance is obtained.

[0093] The material of the hole injection layer 3 and the hole transport layer 4 has at least one of hole injection property, hole transport property, and electron barrier property. The material of the hole injection layer 3 and the hole transport layer 4 may be either organic or inorganic.

[0094] Specific examples of materials for the hole injection layer 3 and the hole transport layer 4 include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, styrylamine compounds, etc. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred, with aromatic tertiary amine compounds being particularly preferred, in terms of the good performance of the organic electroluminescence device.

[0095] Specific examples of the aromatic tertiary amine compound and the styrylamine compound include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(m-tolyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N' -di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), 4,4',4''-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA), and the like.

[0096] Furthermore, inorganic compounds such as p-type Si and p-type SiC can also be given as examples of materials for the hole injection layer and the hole transport layer.

[0097] The hole injection layer 3 and the hole transport layer 4 may have a single structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0098] [Light-emitting layer 5] The light-emitting layer 5 is provided between the hole-transporting layer 4 and the electron-transporting layer 6 described below.

[0099] Examples of materials for the light-emitting layer 5 include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer 5, electron-hole pairs recombine, resulting in light emission.

[0100] The light-emitting layer 5 may consist of a single small molecule material or a single polymer material, but more commonly consists of a host material doped with a guest compound. Light emission comes primarily from the dopant and can be of any color.

[0101] Examples of the host material include compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specific examples include DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)1,1'-biphenyl), TBADN (2-tertiarybutyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, 3-(10-phenyl-9-anthryl)-dibenzofuran, and the like.

[0102] Among the guest compounds, examples of fluorescent dopants include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyril compounds, boron compounds, and cyclic amine compounds. The fluorescent dopant may be a combination of two or more selected from these.

[0103] Among the guest compounds, examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0104] Specific examples of fluorescent dopants and phosphorescent dopants include Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, 2,7-bis[N,N-di-(4-tert-butylphenyl)]amino-bisbenzofurano-9,9'-spirofluorene, bis[2-(4-n-hexylphenyl)quinoline] ( acetylacetonato)iridium(III), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)), and FIrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))), 5,9-diphenyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene, and the like.

[0105] Furthermore, the light-emitting material is not limited to being contained only in the light-emitting layer 5. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer 5 (the hole transport layer 4 or the electron transport layer 6). This may further increase the luminous efficiency of the organic electroluminescence device.

[0106] The light-emitting layer 5 may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0107] [Electron Transport Layer 6] The electron transport layer 6 is provided between the light emitting layer 5 and the electron injection layer 7 described below.

[0108] The electron transport layer 6 has a function of transporting electrons injected from the cathode to the light-emitting layer 5. By interposing the electron transport layer 6 between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer 5 at a lower electric field.

[0109] Specific examples of materials for the electron transport layer 6 include tris(8-quinolinolato)aluminum derivatives, imidazole derivatives, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoline derivatives, quinoxaline derivatives, oxadiazole derivatives, phosphole derivatives, silole derivatives, phosphine oxide derivatives, etc. Among these, triazine derivatives and pyrimidine derivatives are preferred in terms of the good performance of the organic electroluminescence device.

[0110] The electron transport layer 6 may further contain, in addition to the materials listed above, one or more types of electron transport materials selected from conventionally known electron transport materials.

[0111] [Electron Injection Layer 7] The electron injection layer 7 has a function of transferring electrons injected from the cathode to the light-emitting layer 5. By interposing the electron injection layer 6 between the cathode 8 and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0112] The electron injection layer 7 preferably contains at least one element selected from the group consisting of alkali metals, alkaline earth metals, metal halides, metal oxides, rare earth metals, and organometallic complexes, provided that the organometallic complexes contain at least one element selected from the group consisting of alkali metals, alkaline earth metals, and Group 13 metal elements.

[0113] The electron injection layer 7 preferably contains one or more elements selected from the group consisting of lithium, rubidium, cesium, sodium, calcium, barium, lithium fluoride, potassium fluoride, cesium fluoride, magnesium fluoride, calcium fluoride, barium fluoride, magnesium oxide, lithium oxide, ytterbium, samarium, europium, thulium, and 8-hydroxyquinolinatolithium (Liq), because this allows the driving voltage to be further reduced.

[0114] [Cathode 8] The cathode 8 is provided on the electron injection layer 7.

[0115] In the case of an organic electroluminescence element having a configuration in which only light emitted through the anode 2 is extracted, the cathode can be made of any conductive material.

[0116] Examples of materials for the cathode 8 include metals with a low work function (hereinafter also referred to as "electron injection metals"), alloys, electrically conductive compounds, and mixtures thereof. Here, the metals with a low work function are, for example, metals with a work function of 4 eV or less.

[0117] Specific examples of the material of the cathode 8 include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, and aluminum / aluminum oxide (Al ２ O ３ ) mixture, indium, lithium / aluminum mixture, rare earth metals, etc.

[0118] Among these, from the viewpoints of electron injection properties and durability against oxidation, etc., mixtures of an electron injecting metal and a second metal which has a larger and more stable work function than the electron injecting metal, such as magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (AlO) mixtures, and lithium / aluminum mixtures are preferred.

[0119] The cathode 8 may also be patterned with a patterning material.

[0120] [Capping Layer 9] The capping layer 9 has been described above.

[0121] [Method of Forming Each Layer] Each layer except for the electrodes (anode and cathode) described above can be formed by forming a thin film using a known method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc. The material for each layer may be used alone or, if necessary, may be used together with a material such as a binder resin or a solvent.

[0122] There are no particular limitations on the thickness of each layer formed in this way, and it can be selected appropriately depending on the situation, but it is usually in the range of 5 nm to 5 μm.

[0123] The anode 2 and the cathode 8 can be formed by thinning an electrode material by a method such as vapor deposition or sputtering. A pattern may be formed through a mask of a desired shape during vapor deposition or sputtering, or a pattern of a desired shape may be formed by photolithography after forming a thin film by vapor deposition or sputtering.

[0124] The thickness of the anode 2 and the cathode 8 is preferably 1 μm or less, and more preferably 10 nm to 200 nm.

[0125] In the present disclosure, the organic electroluminescent element may be used as a type of lamp for illumination, exposure light source, etc., or as a projection device that projects an image onto a screen, etc., or as a display device (display) that directly views still images or moving images. When an organic electroluminescent element is used as a display device for playing moving images, the driving method may be a simple matrix (passive matrix) method or an active matrix method. Furthermore, by using two or more organic electroluminescent elements that emit light of different colors, a full-color display device can be produced.

[0126] [Compound Represented by Formula (1)] The capping layer material for the organic thin film device described above contains a compound represented by the following formula (1).

[0127]

[0128] In formula (1), each X independently represents an optionally substituted tri- to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; an optionally substituted tri- to tetravalent heteroaromatic group having 3 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; or an optionally substituted cyclic tri- to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0129] In formula (1), each Y independently represents an optionally substituted di- or trivalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; an optionally substituted di- or trivalent monocyclic, linked ring, or fused ring aromatic group having 3 to 26 carbon atoms, which is a heteroaromatic group having 2 or 3 heteroatoms; or an optionally substituted cyclic di- or trivalent aliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0130] In formula (1), each Z independently represents an optionally substituted monovalent aromatic hydrocarbon group of 6 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; an optionally substituted monovalent heteroaromatic group of 3 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring; or an optionally substituted cyclic monovalent aliphatic hydrocarbon group of 3 to 18 carbon atoms.

[0131] In formula (1), a represents an integer of 1 to 4.

[0132] In formula (1), b represents an integer of 0 to 2.

[0133] In formula (1), c represents 1 or 2.

[0134] In formula (1), at least one E is substituted with a fluorine atom.

[0135] The capping layer material for an organic thin film device can be deposited on a substrate to form a film.

[0136] [Regarding X: Substituents] In the above formula (1), when X is an aromatic hydrocarbon group having a substituent, a heteroaromatic group having a substituent, or an aliphatic hydrocarbon group having a substituent, examples of these substituents (hereinafter referred to as "substituents of X") include, each independently, a linear, branched (branched), or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a structure represented by a cyano group, a fluorine atom, or a deuterium atom.

[0137] The substituents of X are preferably each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of X may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0138] [Regarding X: Aromatic Hydrocarbon Group] In the above formula (1), the compound that provides the monovalent aromatic hydrocarbon group of 6 to 26 carbon atoms, represented by X, is preferably a compound having a structure in which phenyl or multiple benzene rings are linked or fused.

[0139] The compound providing the monovalent heteroaromatic group having 6 to 26 carbon atoms and being a single ring, linked ring, or fused ring may be substituted with the substituent of X.

[0140] The compound that provides the monovalent aromatic hydrocarbon group of a single ring, a linked ring, or a fused ring having 6 to 26 carbon atoms is preferably: (X1) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or a structure in which one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these compounds; or (X1') the compound represented by (X1) is substituted with the substituent of X, (X2) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, triptycene, and a structure in which these compounds are condensed with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene, or (X2') it is more preferable that the compound represented by (X2) is substituted with the substituent of X, (X3) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, triptycene, and a structure in which these compounds are condensed with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene, or (X3') the compound represented by (X3) is more preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of X3 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (X4) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, or triptycene, or (X4') the compound represented by (X4) is more preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of X4 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (X5) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, or triptycene, or (X5') it is even more preferable that the compound represented by (X5) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of X5 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (X6) benzene, biphenyl, terphenyl, naphthalene, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, or phenanthrene, or (X6') It is most preferable that the compound represented by (X6) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of X6 may each independently be further substituted with one or more groups selected from the group consisting of the above groups); (X7) benzene, biphenyl, naphthalene, or fluorene, or (X7') It is particularly preferred that the compound represented by (X7) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of X7 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0141] [Regarding X: Heteroaromatic Group] In the above formula (1), the compound that provides the monovalent heteroaromatic group of a single ring, a linked ring, or a fused ring having 3 to 26 carbon atoms, represented by X, preferably has a heteroatom of C, O, or S, and a 5-membered ring, a 6-membered ring, or a fused structure thereof.

[0142] The compound providing the monovalent heteroaromatic group having 6 to 26 carbon atoms and being a single ring, linked ring, or fused ring may be substituted with the substituent of X.

[0143] The compound that provides the monovalent heteroaromatic group of a single ring, a linked ring, or a fused ring having 6 to 26 carbon atoms is preferably: (X8) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole, as well as a structure in which these compounds are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; or (X8') the compound represented by (X8) is substituted with the substituent of X. (X9) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, or (X9') it is more preferable that the compound represented by (X9) is substituted with the substituent of X, (X10) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine or benzothiazole, or (X10') the compound represented by (X10) is more preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of X10 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (X11) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, or (X11') It is even more preferable that the compound represented by (X11) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of X11 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (X12) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, or dibenzo-1,4-dioxin, or (X12') it is most preferable that the compound represented by (X12) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of X12 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0144] [Regarding X: Aliphatic Hydrocarbon Group] In the above formula (1), the compound that provides the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by X, is preferably adamantane, diamantane, norbornene, or cyclohexane.

[0145] The compound providing the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms may be substituted with the substituent X.

[0146] The compound that provides the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms is preferably: (X13) adamantane, diamantane, norbornene, or cyclohexane; or (X13') the compound represented by (X13) is preferably substituted with the substituent of X; (X14) adamantane, diamantane, norbornene, or cyclohexane; (X14') It is more preferable that the compound represented by (X14) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of X14 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (X15) adamantane, diamantane, norbornene, or cyclohexane, or (X15') It is more preferable that the compound represented by (X15) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of X15 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (X16) adamantane, diamantane, or cyclohexane, or (X16') It is most preferable that the compound represented by (X16) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of X16 may each independently be further substituted with one or more groups selected from the group consisting of the above groups).

[0147] [Regarding Y: Substituents] In the above formula (1), when Y is an aromatic hydrocarbon group having a substituent, a heteroaromatic group having a substituent, or an aliphatic hydrocarbon group having a substituent, these substituents (hereinafter referred to as "substituents of Y") are preferably each independently a linear, branched (branched), or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a structure represented by a cyano group, a fluorine atom, or a deuterium atom.

[0148] The substituents of Y are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, and a benzothiazolyl group (wherein the substituents of Y are each independently optionally further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0149] [Regarding Y: Aromatic Hydrocarbon Group] In the above formula (1), the compound that provides the monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, represented by Y, is preferably a compound having a structure in which phenyl or multiple benzene rings are linked or fused.

[0150] The compound providing the monovalent heteroaromatic group having 6 to 26 carbon atoms and being a single ring, linked ring, or fused ring may be substituted with the substituent for Y.

[0151] The compound that provides the monovalent aromatic hydrocarbon group of a single ring, a linked ring, or a fused ring having 6 to 26 carbon atoms is preferably: (Y1) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or a structure in which one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these groups; or (Y1') the compound represented by (Y1) is substituted with the substituent of Y, (Y2) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, triptycene, and a structure in which these groups are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene, or (Y2') it is more preferable that the compound represented by (Y2) is substituted with the substituent of Y, (Y3) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, triptycene, and a structure in which these groups are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene, or (Y3') It is more preferable that the compound represented by (Y3) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Y3 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups); (Y4) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, or triptycene, or (Y4') the compound represented by (Y4) is even more preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Y4 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (Y5) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, or triptycene, or (Y5') the compound represented by (Y5) is most preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Y5 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Y6) benzene, biphenyl, terphenyl, naphthalene, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene or phenanthrene, or (Y6') it is even more preferable that the compound represented by (Y6) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Y6 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (Y7) benzene, biphenyl, naphthalene, or fluorene, or (Y7') It is particularly preferred that the compound represented by (Y7) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Y6 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0152] [Regarding Y: Heteroaromatic Group] In the above formula (1), the compound that provides the monovalent heteroaromatic group of a single ring, a linked ring, or a fused ring having 3 to 26 carbon atoms, represented by Y, preferably has a heteroatom of C, O, or S, and has a 5-membered ring, a 6-membered ring, or a structure in which these are fused.

[0153] The compound providing the monovalent heteroaromatic group having 6 to 26 carbon atoms and being a single ring, linked ring, or fused ring may be substituted with the substituent for Y.

[0154] The compound that provides the monovalent heteroaromatic group of a single ring, a linked ring, or a fused ring having 6 to 26 carbon atoms is preferably: (Y8) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole, as well as a structure in which one or more selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these groups; or (Y8') the compound represented by (Y8) is substituted with the substituent of Y, (Y9) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, or (Y9') it is more preferable that the compound represented by (Y9) is substituted with the substituent of Y, (Y10) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine or benzothiazole, or (Y10') the compound represented by (Y10) is more preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Y10 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (Y11) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, or (Y11') It is even more preferable that the compound represented by (Y11) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Y11 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Y12) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, or dibenzo-1,4-dioxin, or (Y12') it is most preferable that the compound represented by (Y12) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Y12 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0155] [Regarding Y: Aliphatic Hydrocarbon Group] In the above formula (1), the compound that provides the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by Y, is preferably adamantane, diamantane, norbornene, or cyclohexane.

[0156] The compound providing the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms may be substituted with the substituent for Y.

[0157] The compound that provides the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms is preferably: (Y13) adamantane, diamantane, norbornene, or cyclohexane; or (Y13') the compound represented by (Y13) is preferably substituted with the substituent of Y; (Y14) adamantane, diamantane, norbornene, or cyclohexane; (Y14') It is more preferable that the compound represented by (Y14) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Y14 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Y15) adamantane, diamantane, norbornene, or cyclohexane, or (Y15') It is more preferable that the compound represented by (Y15) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Y15 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Y16) adamantane, diamantane, or cyclohexane, or (Y16') It is most preferable that the compound represented by (Y16) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Y16 may each independently be further substituted with one or more groups selected from the group consisting of the above groups).

[0158] [Regarding Z: Substituents] In the above formula (1), when Z is an aromatic hydrocarbon group having a substituent, a heteroaromatic group having a substituent, or an aliphatic hydrocarbon group having a substituent, these substituents (hereinafter referred to as "substituents of Z") are preferably each independently a linear, branched (branched), or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a structure represented by a cyano group, a fluorine atom, or a deuterium atom.

[0159] The substituents of Z are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Z are each independently optionally further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0160] [Regarding Z: Aromatic Hydrocarbon Group] In the above formula (1), the compound that provides the monovalent aromatic hydrocarbon group of 6 to 26 carbon atoms, represented by Z, is preferably a phenyl or a structure in which multiple benzene rings are linked or fused.

[0161] The compound providing the monovalent heteroaromatic group having 6 to 26 carbon atoms and being a single ring, linked ring, or fused ring may be substituted with the substituent Z described above.

[0162] The compound that provides the monovalent aromatic hydrocarbon group of a single ring, a linked ring, or a fused ring having 6 to 26 carbon atoms is preferably: (Z1) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or a structure in which one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these groups; or (Z1') the compound represented by (Z1) is substituted with the substituent of Z, (Z2) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, triptycene, and a structure in which these groups are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene, or (Z2') it is more preferable that the compound represented by (Z2) is substituted with the substituent of Z, (Z3) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, triptycene, and a structure in which these groups are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene, or (Z3') It is more preferable that the compound represented by (Z3) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Z3 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Z4) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, or triptycene, or (Z4') the compound represented by (Z4) is even more preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Z4 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (Z5) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, or triptycene, or (Z5') the compound represented by (Z5) is most preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Z5 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Z6) benzene, biphenyl, terphenyl, naphthalene, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene or phenanthrene, or (Z6') it is even more preferable that the compound represented by (Z6) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Z6 may each independently be further substituted with one or more groups selected from the group consisting of the above groups), (Z7) benzene, biphenyl, naphthalene, or fluorene, or (Z7') It is particularly preferred that the compound represented by (Z7) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Z7 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0163] [Regarding Z: Heteroaromatic Group] In the above formula (1), the compound that provides the monovalent heteroaromatic group of a single ring, a linked ring, or a fused ring having 3 to 26 carbon atoms, represented by Z, preferably has a heteroatom of C, O, or S, and a structure of a 5-membered ring, a 6-membered ring, or a fused structure thereof.

[0164] The compound providing the monovalent heteroaromatic group having 6 to 26 carbon atoms and being a single ring, linked ring, or fused ring may be substituted with the substituent Z described above.

[0165] The compound that provides the monovalent heteroaromatic group of a single ring, a linked ring, or a fused ring having 6 to 26 carbon atoms is preferably: (Z8) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and a structure in which one or more selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these groups; or (Z8') the compound represented by (Z8) is substituted with the substituent of Z, (Z9) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, or (Z9') it is more preferable that the compound represented by (Z9) is substituted with the substituent of Z, (Z10) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine or benzothiazole, or (Z10') the compound represented by (Z10) is more preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Z10 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Z11) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, or (Z11') It is even more preferable that the compound represented by (Z11) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Z11 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Z12) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, or dibenzo-1,4-dioxin, or (Z12') the compound represented by (Z12) is most preferably substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Z11 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0166] [Regarding Z: Aliphatic Hydrocarbon Group] In the above formula (1), the compound that provides the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms represented by Z is preferably adamantane, diamantane, norbornene, or cyclohexane.

[0167] The compound providing the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms may be substituted with the substituent Z described above.

[0168] The compound that provides the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms is preferably: (Z13) adamantane, diamantane, norbornene, or cyclohexane; or (Z13') the compound represented by (Z13) is preferably substituted with the substituent of Z; or (Z14) adamantane, diamantane, norbornene, or cyclohexane; (Z14') It is more preferable that the compound represented by (Z14) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, or a benzothiazolyl group (wherein the substituents of Z14 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Z15) adamantane, diamantane, norbornene, or cyclohexane, or (Z15') It is more preferable that the compound represented by (Z15) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Z15 may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (Z16) adamantane, diamantane, or cyclohexane, or (Z16') It is most preferable that the compound represented by (Z16) is substituted with a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, or a triazyl group (wherein the substituents of Z16 may each independently be further substituted with one or more groups selected from the group consisting of the above groups).

[0169] [Regarding Z: Substitution with Fluorine Atom] In the above formula (1), at least one Z is substituted with a fluorine atom.

[0170] In the above formula (1), it is preferable that at least two Z's are substituted with a fluorine atom.

[0171] In the above formula (1), the four Z's preferably have a total of four or more fluorine atoms as substituents, more preferably six or more fluorine atoms, and even more preferably eight or more fluorine atoms.

[0172] In the above formula (1), it is preferable that all Z's are substituted with at least one fluorine atom.

[0173] [a, b, c] In the above formula (1), a represents an integer of 1 to 4. a is preferably an integer of 1 to 3, more preferably 1 or 2, and more preferably 1.

[0174] In the above formula (1), b represents an integer of 0 to 2. b is preferably 0 or 1.

[0175] In the above formula (1), c represents 1 or 2. Preferably, c is 1.

[0176] [Amine Compound] The amine compound according to one embodiment of the present disclosure is represented by the following formula (2).

[0177]

[0178] In formula (2), each A independently represents a monocyclic, linked, or fused ring tri- or tetravalent aromatic hydrocarbon group having 6 to 13 carbon atoms which may be substituted with a fluorine atom; a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a monocyclic, linked, or fused ring tri- or tetravalent heteroaromatic group having 3 to 11 carbon atoms which may be substituted with a fluorine atom; or a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a cyclic tri- or tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted with a fluorine atom.

[0179] In formula (2), each B independently represents a divalent or trivalent aromatic hydrocarbon group having 6 to 13 carbon atoms, a divalent or trivalent monocyclic, linked ring, or fused ring aromatic group having 3 to 11 carbon atoms, or a divalent or trivalent aliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0180] In formula (2), each E independently represents a monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, a monovalent heteroaromatic group having 3 to 26 carbon atoms, a monovalent heteroaromatic group having 3 to 26 carbon atoms, or a cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0181] In formula (2), l represents an integer of 1 to 4.

[0182] In formula (2), m represents an integer of 0 to 2.

[0183] In formula (2), n represents 1 or 2.

[0184] In formula (2), at least one E is an aromatic hydrocarbon group, a heteroaromatic group, or an aliphatic hydrocarbon group that constitutes E, and is substituted with one or more fluorine atoms.

[0185] In formula (2), B and E may each independently be substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of B and E may each independently be further substituted with one or more groups selected from the group consisting of the above-mentioned groups).

[0186] [Regarding A: Aromatic Hydrocarbon Group] In the above formula (2), the compound that provides the monocyclic, linked ring, or fused ring trivalent to tetravalent aromatic hydrocarbon group having 6 to 13 carbon atoms, represented by A, is preferably: (A1) benzene, biphenyl, naphthalene, or fluorene; or (A1') the compound represented by (A1) is substituted with one or more fluorine atom groups; (A2) benzene, biphenyl, or naphthalene; or (A2') the compound represented by (A2) is more preferably substituted with one or more fluorine atom groups; (A3) benzene or biphenyl; or (A3') the compound represented by (A3) is even more preferably substituted with one or more fluorine atom groups; (A4) benzene; or (A4') the compound represented by (A4) is even more preferably substituted with one or more fluorine atom groups.

[0187] [Regarding A: Heteroaromatic Group] In the above formula (2), examples of compounds that provide a monocyclic, linked or fused ring trivalent to tetravalent heteroaromatic group having 3 to 11 carbon atoms and optionally substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom, represented by A, include: (A5) pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole; or (A5') the compound represented by (A5) is preferably substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom; (A6) pyridine, pyrimidine, pyrazine, triazine, benzofuran, benzothiophene, benzodioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine or benzothiazole, or (A6') the compound represented by (A6) is more preferably substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom, (A7) pyridine, pyrimidine, pyrazine, triazine, benzofuran, benzothiophene, benzodioxin, or benzothiazole, or (A7') the compound represented by (A7) is even more preferably substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom, (A8) pyridine, pyrimidine, pyrazine, triazine, benzofuran, benzothiophene, benzodioxin, or benzothiazole, or (A8') the compound represented by (A8) is even more preferably substituted with a pentafluorophenyl group, a tetrafluoropyridyl group, or a fluorine atom, (A9) Pyridine, pyrimidine, pyrazine, or triazine, or (A9') the compound represented by (A9) is particularly preferably substituted with a fluorine atom.

[0188] [Regarding A: Aliphatic Hydrocarbon Group] In the above formula (2), the compound that provides the cyclic trivalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by A, is preferably: (A10) adamantane, diamantane, norbornene, or cyclohexane; or (A10') the compound represented by (A10) is preferably substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom; (A11) adamantane, diamantane, or norbornene; or (A11') the compound represented by (A12) is more preferably substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom; (A13) adamantane or diamantane; (A13') It is more preferable that the compound represented by (A13) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, or a fluorine atom, and (A14) it is most preferable that the compound represented by (A14) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, or a fluorine atom.

[0189] [Regarding B: Aromatic Hydrocarbon Group] In the above formula (2), the compound that provides the monocyclic, linked ring, or fused ring divalent or trivalent aromatic hydrocarbon group having 6 to 13 carbon atoms, represented by B, is preferably: (B1) benzene, biphenyl, naphthalene, or fluorene; or (B1') the compound represented by (B1) is preferably substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituent of the compound represented by (B1) may be further substituted with one or more groups selected from the group consisting of the above groups); (B2) benzene, biphenyl, or naphthalene; or (B2') It is more preferable that the compound represented by (B2) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents on the compound represented by (B2) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups); (B3) benzene, biphenyl, or naphthalene; or (B3') It is even more preferable that the compound represented by (B3) is substituted with a phenyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, an adamantyl group, or a fluorine atom; (B4) It is most preferable that the compound represented by (B4) is substituted with a phenyl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, or a fluorine atom.

[0190] [Regarding B: Heteroaromatic Group] In the above formula (2), examples of compounds that provide the monocyclic, linked, or fused trivalent to tetravalent heteroaromatic group having 3 to 11 carbon atoms, represented by B, include: (B5) pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole; or (B5') the compound represented by (B5) is preferably substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (B5) may be further substituted with one or more groups selected from the group consisting of the above groups). (B6) pyridine, pyrimidine, pyrazine, triazine, benzofuran, benzothiophene, benzodioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine or benzothiazole, or (B6') it is more preferable that the compound represented by (B6) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (B6) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (B7) pyridine, pyrimidine, pyrazine, triazine, benzofuran, benzothiophene, benzodioxin, or benzothiazole, or (B7') it is more preferable that the compound represented by (B7) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom, (B8) pyridine, pyrimidine, pyrazine, triazine, benzofuran, benzothiophene, benzodioxin, or benzothiazole, or (B8') It is even more preferable that the compound represented by (B8) is substituted with a pentafluorophenyl group, a tetrafluoropyridyl group, or a fluorine atom; (B9) It is most preferable that the compound represented by (B9) is pyridine, pyrimidine, pyrazine, or triazine; or (B9') It is most preferable that the compound represented by (B9) is substituted with a fluorine atom.

[0191] [Regarding B: Aliphatic Hydrocarbon Group] In the above formula (2), the compound that provides the cyclic trivalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by B, is preferably: (B10) adamantane, diamantane, norbornene, or cyclohexane; or (B10') the compound represented by (B10) is preferably substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituent of the compound represented by (B10) may be further substituted with one or more groups selected from the group consisting of the above groups); (B11) adamantane, diamantane, or norbornene; or (B11') It is more preferable that the compound represented by (B12) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (B11) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (B12) adamantane or diamantane, or (B12') It is more preferable that the compound represented by (B12) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (B12) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (B13) adamantane or diamantane, or (B13') It is most preferable that the compound represented by (B13) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, or a fluorine atom.

[0192] [Regarding E: Aromatic Hydrocarbon Group] In the above formula (2), examples of compounds that provide the monovalent aromatic hydrocarbon group of a single ring, a linked ring, or a fused ring having 6 to 26 carbon atoms, represented by E, include: (E1) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or a structure in which one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these compounds; (E1') The compound represented by (E1) is preferably substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (here, the substituent possessed by the compound represented by (E1) may be further substituted with one or more groups selected from the group consisting of the above groups); (E2) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, triptycene, or a structure in which these compounds are condensed with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; or (E2') It is more preferable that the compound represented by (E2) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (here, the substituent possessed by the compound represented by (E2) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (E3) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, triptycene, or a structure in which benzene is condensed with these compounds, or (E3') it is more preferable that the compound represented by (E3) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituent of the compound represented by (E3) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (E4) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, or triptycene, or (E4') It is even more preferable that the compound represented by (E4) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (here, the substituents of the compound represented by (E4) may be further substituted with one or more groups selected from the group consisting of the above groups); (E5) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, or triptycene; or (E5') It is most preferable that the compound represented by (E5) is substituted with a phenyl group, a pentafluorophenyl group, a lysyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom; (E6) benzene, biphenyl, terphenyl, naphthalene, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene or phenanthrene, or (E6') the compound represented by (E6) is most preferably substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom, (E7) benzene, biphenyl, naphthalene, or fluorene, or (E7') the compound represented by (E7) is particularly preferably substituted with a pentafluorophenyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom.

[0193] [Regarding E: Heteroaromatic Group] In the above formula (2), examples of compounds that provide the monovalent heteroaromatic group of a single ring, a linked ring, or a fused ring having 6 to 26 carbon atoms represented by E include: (E8) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or a structure in which one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these compounds; (E8') The compound represented by (E8) is preferably substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (E8) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (E9) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine or benzothiazole, or (E9') it is more preferable that the compound represented by (E9) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (E9) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (E10) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, or benzothiazole, or (E10') It is even more preferable that the compound represented by (E10) is a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, a substituent represented by a fluorine atom, or that these groups (substituents) are further substituted with one or more groups selected from the group consisting of these groups (substituents); (E11) pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, thiazole, thiadiazole, benzo-1,4-dioxin, or benzothiazole; or (E12') It is even more preferable that the compound represented by (E12) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (12) may be further substituted with one or more groups selected from the group consisting of the above groups). (E13) pyridine, pyrimidine, pyrazine, triazine, benzofuran, benzothiophene, thiazole, thiadiazole, benzo-1,4-dioxin, or benzothiazole, or (E13') the compound represented by (E13) is most preferably substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom.

[0194] [Regarding E: Aliphatic Hydrocarbon Group] In the above formula (2), the compound that provides the cyclic trivalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by E, is preferably: (E14) adamantane, diamantane, norbornene, or cyclohexane; or (E14') the compound represented by (E14) is preferably substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, a fluorine atom, or a fluorine atom (wherein the substituent of the compound represented by (E14) may be further substituted with one or more groups selected from the group consisting of the above groups); (E15) adamantane, diamantane, or norbornene; or (E15') It is more preferable that the compound represented by (E15) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (E15) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (E16) adamantane or diamantane, or (E16') It is more preferable that the compound represented by (E16) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents of the compound represented by (E16) may be further substituted with one or more groups selected from the group consisting of the above-mentioned groups), (E17) adamantane or diamantane, or (E17') It is most preferable that the compound represented by (E17) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, or a fluorine atom.

[0195] [Regarding E: Substitution by Fluorine Atom] In the above formula (2), at least one E is substituted by a fluorine atom.

[0196] In the above formula (2), it is preferable that at least two E's are substituted with fluorine atoms.

[0197] In the above formula (2), the four E's preferably have a total of four or more fluorine atoms as substituents, more preferably six or more fluorine atoms, and even more preferably eight or more fluorine atoms.

[0198] [Regarding E: Number of Carbon Atoms] In the above formula (2), the number of carbon atoms in the fused aromatic hydrocarbon group is preferably 6 to 20. Specifically, it is preferably 6 to 20, more preferably 6 to 15, and even more preferably 6 to 13.

[0199] In the above formula (2), the number of carbon atoms in the fused heteroaromatic hydrocarbon group is preferably 3 to 20. Specifically, it is preferably 3 to 20, more preferably 3 to 15, even more preferably 3 to 13, and even more preferably 3 to 11.

[0200] [l, m, n] In the above formula (2), l represents an integer of 1 to 4. l is preferably an integer of 1 to 3, more preferably 1 or 2, and more preferably 1.

[0201] In the above formula (2), m represents an integer of 0 to 2. m is preferably 0 or 1.

[0202] In the above formula (2), n represents 1 or 2. Preferably, n is 1.

[0203] [Preferable specific examples of compounds] As preferred specific examples of the amine compounds represented by the above formula (1) and the amine compounds represented by the above formula (2), the following compounds (A001) to (A120) are exemplified, but the present disclosure is not limited to these compounds.

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples.

[0214] The analytical instruments used in this example are listed below.

[0215] [Transmittance Measurement] Measuring device: V-750 manufactured by JASCO Corporation, Measurement range: 450 to 900 nm.

[0216] [Refractive index measurement] Measurement device: J.A. Woollam's multi-angle spectroscopic ellipsometry M-2000U, measurement range: 450 to 900 nm.

[0217] [Measurement of Light Emitting Properties] Measuring device: Luminance meter BM-9 manufactured by Topcon Technohouse, Measurement environment: 25°C environment.

[0218] Example 1A Synthesis of Compound (A010) Synthesis 1-1 Synthesis of Intermediate (I1)

[0219]

[0220] Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), 1-adamantyl-4-phenylboronic acid (pinacol) (12.0 mmol), and 1-bromo-3,5-dinitrobenzene (12.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the solution was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target intermediate (I1) as a white solid (yield 68%).

[0221] The compound was identified by FDMS measurement (FDMS: 378).

[0222] Synthesis 1-2 Synthesis of intermediate (I2)

[0223]

[0224] Intermediate I1 (6.0 mmol) and palladium / carbon (12.0 mmol) were dissolved in THF (100 ml) and the mixture was purged with hydrogen. After stirring at room temperature for 24 hours, the mixture was purged with nitrogen. Next, the mixture was filtered through pleated filter paper, and the filtrate was concentrated to obtain a solid. The solid was dissolved in chloroform and separated using pure water. The organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I2) as a white solid (yield 88%).

[0225] The compound was identified by FDMS measurement (FDMS: 318).

[0226] Synthesis 1-3 Synthesis of compound (A010)

[0227]

[0228] Under a nitrogen atmosphere, intermediate I2 (5.0 mmol), perfluoropyridine (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 80°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A010) (yield 68%).

[0229] The compound was identified by FDMS measurement (FDMS: 914).

[0230] Example 1B Evaluation of refractive index of compound (A010) A silicon substrate was subjected to boiling cleaning with isopropyl alcohol, and then further subjected to ultraviolet ozone cleaning. After that, the silicon substrate was placed in a vacuum deposition apparatus and subjected to a 1.0×10 －４ The chamber was evacuated with a vacuum pump until the pressure reached or below Pa. Compound (A010) was deposited at a deposition rate of 0.1 nm / sec to form a film of 50 nm on a silicon substrate on which a metal mask with an opening of 20 mm×10 mm was placed.

[0231] Measurements were performed using a multi-angle spectroscopic ellipsometer (M-2000U; manufactured by J.A. Woollam) by changing the angle of incidence of light in 5-degree increments over the range of 45 to 75 degrees. At each angle, the ellipsometry parameters Ψ and Δ were measured at approximately 1.6 nm intervals over the wavelength range of 460 to 900 nm. Using the above measurement data, the imaginary part of the dielectric function of the organic semiconductor was expressed as a superposition of Gaussian functions, and fitting analysis was performed under conditions satisfying the Kramers-Kroning equation to obtain the refractive index and extinction coefficient of the layer for each wavelength of light. The refractive index of compound (A010) was 1.60 or less over the range of 450 to 900 nm. The refractive index of compound (A010) is shown in Table 1 and Figure 3.

[0232] Example 1C Evaluation of Transmittance of Compound (A010) A glass substrate was subjected to boiling cleaning with isopropyl alcohol, and then further subjected to ultraviolet ozone cleaning. After that, the substrate was placed in a vacuum deposition apparatus and a 1.0×10 －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 100 Pa or less. Compound (A010) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The results of the transmittance measurement are shown in Figure 4A. The transmittance of compound (A010) was 90% or more in the range of 450 to 900 nm. The transmittance of compound (A010) is shown in Table 1 and Figure 4.

[0233] Example 1D Evaluation of element using low refractive index material: compound (A010) in capping layer (Preparation of substrate 1 and anode 2) A glass substrate with a reflective ITO electrode was prepared as substrate 1 having an anode 2 on its surface. Next, this substrate was washed with isopropyl alcohol, and then subjected to surface treatment by ozone ultraviolet cleaning.

[0234] (Preparation for Vacuum Deposition) Each layer was vacuum-deposited on the cleaned and surface-treated substrate by a vacuum deposition method, and each layer was laminated.

[0235] First, the glass substrate was placed in a vacuum deposition chamber. －４ The pressure was reduced to Pa. Then, each layer was formed according to the film formation conditions in the following order. Each organic material was formed into a film by resistance heating.

[0236] (Fabrication of Hole Injection Layer 3) Sublimation-purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were mixed in a mass ratio of 99:1 to form a 10 nm film, thereby fabricating Hole Injection Layer 3. The film formation rate was 0.1 nm / sec.

[0237] (Preparation of First Hole Transport Layer 41) Sublimation-purified N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine was formed into a film having a thickness of 85 nm at a rate of 0.2 nm / sec to prepare a first hole transport layer 41.

[0238] (Preparation of Second Hole Transport Layer 42) Sublimation-purified N-phenyl-N-(9,9-diphenylfluoren-2-yl)-N-(1,1'-biphenyl-4-yl)amine was deposited at a rate of 0.15 nm / sec to form a film of 5 nm, thereby preparing the second hole transport layer 42.

[0239] (Fabrication of Light-Emitting Layer 5) Sublimation-purified 3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9′-spirofluorene were mixed in a mass ratio of 95:5 to form a 30 nm film, thereby forming the light-emitting layer 5. The film formation rate was 0.1 nm / sec.

[0240] (Preparation of Hole Blocking Layer 61) Sublimation-purified 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine was deposited at a rate of 0.05 nm / sec to form a 6 nm thick film to prepare a hole blocking layer 61.

[0241] (Preparation of Electron Transport Layer 6) A 25 nm thick film of 6-[4′-(2-phenyl-6-quinolyl)biphenyl-4-yl]-2,4-diphenyl-1,3,5-triazine and 8-hydroxyquinolinolatolithium (hereinafter referred to as Liq) was formed in a mass ratio of 50:50 to prepare an electron transport layer 6. The film formation rate was 0.15 nm / sec.

[0242] (Preparation of Electron Injection Layer 7) Ytterbium was deposited at a rate of 0.02 nm / sec to a thickness of 1 nm to prepare the electron injection layer 7.

[0243] (Fabrication of Cathode 8) A silver / magnesium (mass ratio 1 / 10) film was formed to a thickness of 12 nm to form the cathode 8. The film formation rate of the silver / magnesium film was 0.5 nm / second.

[0244] (Fabrication of High Refractive Index Layer 91) Sublimation-purified N4',N4'-diphenyl-N4',N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine was deposited at a rate of 0.05 nm / sec to form a 50 nm film, thereby fabricating high refractive index layer 91. The refractive index of N4',N4'-diphenyl-N4',N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine in the range of 450 to 900 nm was 1.75 or higher.

[0245] (Preparation of Low Refractive Index Layer 92) The compound (A010) purified by sublimation was deposited at a rate of 0.05 nm / second to form a film of 80 nm, thereby preparing the low refractive index layer 92.

[0246] As a result, the light-emitting area of ​​4 mm 2 shown in FIG. ２ The film thickness of each layer was measured using a stylus film thickness meter (DEKTAK, manufactured by Bruker).

[0247] A direct current was applied to the fabricated organic electroluminescent device, and the light-emitting characteristics were evaluated.

[0248] The light-emitting characteristics are: current density 10 mA / cm ２The voltage (V) and power efficiency (lm / A) were measured when current was passed through the device. The current efficiency (lm / A; luminous efficiency) was expressed as a relative value, with the value for Comparative Example 1D being set at 100. The results are shown in Table 1.

[0249] Example 2A Synthesis of Compound (A001) Synthesis 2-1 Synthesis of Intermediate (I3)

[0250]

[0251] 1-Adamantyl-3,5-dinitrobenzene (6.0 mmol) and palladium / carbon (12.0 mmol) were dissolved in THF (100 ml) and the mixture was purged with a hydrogen atmosphere. After stirring at room temperature for 24 hours, the mixture was purged with a nitrogen atmosphere. Next, the mixture was filtered through pleated filter paper, and the filtrate was concentrated to obtain a solid. The solid was dissolved in chloroform and separated using pure water, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I3) (yield 86%).

[0252] The compound was identified by FDMS measurement (FDMS: 242).

[0253] Synthesis 2-2 Synthesis of Compound (A001)

[0254]

[0255] Under a nitrogen atmosphere, intermediate I3 (5.0 mmol), perfluoropyridine (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 80°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A001) (yield 78%).

[0256] The compound was identified by FDMS measurement (FDMS: 838).

[0257] Example 2B Evaluation of Refractive Index of Compound (A001) The refractive index of compound (A001) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0258] Example 2C Evaluation of Transmittance of Compound (A001) The transmittance of compound (A001) was measured using the same method as in Example 1C. The results are shown in Table 1.

[0259] Example 2D Evaluation of a device using a low refractive index material: compound (A001) in a capping layer Using the same method as in Example 1D, steps up to the cathode 8 were prepared.

[0260] (Preparation of Low Refractive Index Layer 92) The compound (A001) purified by sublimation was deposited at a rate of 0.05 nm / second to form a film of 50 nm, thereby preparing the low refractive index layer 92.

[0261] (Preparation of High Refractive Index Layer 91) Sublimation-purified N4',N4'-diphenyl-N4',N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine was deposited at a rate of 0.05 nm / sec to a thickness of 50 nm to prepare high refractive index layer 91.

[0262] As a result, the light-emitting area of ​​4 mm 2 shown in FIG. ２ The film thickness of each layer was measured using a stylus film thickness meter (DEKTAK, manufactured by Bruker).

[0263] A direct current was applied to the fabricated organic electroluminescent device, and the light-emitting characteristics were evaluated.

[0264] The light-emitting characteristics are: current density 10 mA / cm ２ The voltage (V) and power efficiency (lm / A) were measured when current was passed through the device. The current efficiency (lm / A; luminous efficiency) was expressed as a relative value, with the value for Comparative Example 1D being set at 100. The results are shown in Table 1.

[0265] A device using the compound (A001) in the low refractive index layer 92 was fabricated using the same method as in Example 1D, and the light emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0266] Example 3A Synthesis of Compound (A060) Synthesis 3-1 Synthesis of Intermediate (I4)

[0267]

[0268] 1,5-Diaminonaphthalene (30.0 mmol) and 1-adamantanol (30.0 mmol) were dissolved in acetic acid (30 ml) and cooled to 0°C with ice water. Next, sulfuric acid (20 ml) was slowly added dropwise. After the addition was completed, the mixture was heated at 80°C for 24 hours. After cooling to room temperature, the mixture was neutralized with aqueous sodium hydroxide solution while cooling with water to obtain a solid. The solid was dissolved in chloroform, and the layers were separated using pure water. The organic layer was further washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I4) (yield 22%).

[0269] The compound was identified by FDMS measurement (FDMS: 292).

[0270] Synthesis 3-2 Synthesis of compound (A060)

[0271]

[0272] Under a nitrogen atmosphere, intermediate I4 (5.0 mmol), perfluorotoluene (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated into pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A060) (yield 61%).

[0273] The compound was identified by FDMS measurement (FDMS: 1156).

[0274] Example 3B Evaluation of Refractive Index of Compound (A060) The refractive index of compound (A060) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0275] Example 3C Evaluation of Transmittance of Compound (A060) The transmittance of compound (A060) was measured using the same method as in Example 1C. The results are shown in Table 1.

[0276] Example 3D Low refractive index material: Evaluation of element using compound (A060) in capping layer An element using compound (A060) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0277] Example 4A Synthesis of Compound (A062) Synthesis 4-1 Synthesis of Intermediate (I5)

[0278]

[0279] Under a nitrogen atmosphere, sodium hydride (15.0 mmol) was suspended in tetrahydrofuran (20 ml) and stirred at 0°C. To the suspension, aniline (12.0 mmol) was added dropwise over 20 minutes. After the addition was complete, the mixture was returned to room temperature and stirred for 2 hours. Furthermore, a tetrahydrofuran solution (40 ml) of cyanuric chloride (5.0 mmol) was added dropwise to the suspension at 0°C over 20 minutes. After the addition was complete, the mixture was stirred at room temperature for 5 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I5) (yield 54%).

[0280] The compound was identified by FDMS measurement (FDMS: 297).

[0281] Synthesis 4-2 Synthesis of intermediate (I6)

[0282]

[0283] Under a nitrogen atmosphere, intermediate I5 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I6) (yield 54%).

[0284] The compound was identified by FDMS measurement (FDMS: 729).

[0285] Synthesis 4-3 Synthesis of compound (A062)

[0286]

[0287] Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), 1-adamantyl-4-phenylboronic acid (pinacol) (12.0 mmol), and intermediate I6 (10.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the solution was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target compound (A062) (yield 41%).

[0288] The compound was identified by FDMS measurement (FDMS: 905).

[0289] Example 4B Evaluation of Refractive Index of Compound (A062) The refractive index of compound (A062) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0290] Example 4C Evaluation of Transmittance of Compound (A062) The transmittance of compound (A062) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0291] Example 4D Low refractive index material: Evaluation of element using compound (A062) in capping layer An element using compound (A062) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the luminescence characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0292] Example 5A Synthesis of Compound (A064) Synthesis 5-1 Synthesis of Intermediate (I7)

[0293]

[0294] Under a nitrogen atmosphere, sodium hydride (15.0 mmol) was suspended in tetrahydrofuran (20 ml) and stirred at 0°C. To this suspension, 2-methyl-4-amino-pyridine (12.0 mmol) was added dropwise over 20 minutes. After the addition was complete, the mixture was returned to room temperature and stirred for 2 hours. To this suspension, a tetrahydrofuran solution (40 ml) of 2,4,6-trichloropyrimidine (5.0 mmol) was added dropwise over 20 minutes at 0°C. After the addition was complete, the mixture was stirred at room temperature for 5 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I7) (yield 43%).

[0295] The compound was identified by FDMS measurement (FDMS: 326).

[0296] Synthesis 5-2 Synthesis of intermediate (I8)

[0297]

[0298] Under a nitrogen atmosphere, intermediate I7 ​​(5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I8) (yield 45%).

[0299] The compound was identified by FDMS measurement (FDMS: 758).

[0300] Synthesis 5-3 Synthesis of compound (A064)

[0301]

[0302] Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), 1-adamantyl-4-phenylboronic acid (pinacol) (12.0 mmol), and intermediate I8 (10.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the solution was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target compound (A064) (yield 34%).

[0303] The compound was identified by FDMS measurement (FDMS: 934).

[0304] Example 5B Evaluation of Refractive Index of Compound (A064) The refractive index of compound (A064) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0305] Example 5C Evaluation of Transmittance of Compound (A064) The transmittance of compound (A064) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0306] Example 5D Low refractive index material: Evaluation of element using compound (A064) in capping layer An element using compound (A064) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0307] Example 6A Synthesis of Compound (A072) Synthesis 6-1 Synthesis of Intermediate (I9)

[0308]

[0309] 1,5-Difluoro-2,4-dinitrobenzene (6.0 mmol) and palladium / carbon (12.0 mmol) were dissolved in THF (100 ml) and the mixture was purged with a hydrogen atmosphere. After stirring at room temperature for 24 hours, the atmosphere was purged with nitrogen. Next, the mixture was filtered through pleated filter paper, and the filtrate was concentrated and separated into chloroform and pure water. The organic layer was further washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I9) (yield 42%).

[0310] The compound was identified by FDMS measurement (FDMS: 144).

[0311] Synthesis 6-2 Synthesis of intermediate (I10)

[0312]

[0313] Intermediate I9 (30.0 mmol) and 1-adamantanol (30.0 mmol) were dissolved in acetic acid (30 ml) and cooled to 0°C with ice water. Next, sulfuric acid (20 ml) was slowly added dropwise. After the addition was completed, the mixture was heated at 80°C for 24 hours. After cooling to room temperature, the mixture was neutralized with aqueous sodium hydroxide solution while cooling with water to obtain a solid. The solid was dissolved in chloroform, and the layers were separated using pure water. The organic layer was further washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I10) (yield 21%).

[0314] The compound was identified by FDMS measurement (FDMS: 278).

[0315] Synthesis 6-3 Synthesis of compound (A072)

[0316]

[0317] Under a nitrogen atmosphere, intermediate I10 (5.0 mmol), perfluoropyridine (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 80°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A072) (yield 61%).

[0318] The compound was identified by FDMS measurement (FDMS: 874).

[0319] Example 6B Evaluation of Refractive Index of Compound (A072) The refractive index of compound (A072) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0320] Example 6C Evaluation of Transmittance of Compound (A072) The transmittance of compound (A072) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0321] Example 6D Low refractive index material: Evaluation of element using compound (A072) in capping layer An element using compound (A072) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the luminescence characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0322] Example 7A Synthesis of Compound (A075) Synthesis 7-1 Synthesis of Intermediate (I11)

[0323]

[0324] Under a nitrogen atmosphere, tris(dibenzylideneacetone)palladium(0) (0.18 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.18 mmol) were added to a xylene (50 ml) solution of 3-bromo-4'-methyldiphenylamine (4.0 mmol), 1-adamantylamine (10.0 mmol), and sodium t-butoxide (15.0 mmol), followed by stirring at 80°C for 6 hours. After allowing to cool to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I11) (yield 70%).

[0325] The compound was identified by FDMS measurement (FDMS: 332).

[0326] Synthesis 7-2 Synthesis of intermediate (I12)

[0327]

[0328] Intermediate I11 (30.0 mmol) and 1-adamantanol (30.0 mmol) were dissolved in acetic acid (30 ml) and cooled to 0°C with ice water. Next, sulfuric acid (20 ml) was slowly added dropwise. After the addition was completed, the mixture was heated at 80°C for 24 hours. After cooling to room temperature, the mixture was neutralized with aqueous sodium hydroxide solution while cooling with water to obtain a solid. The solid was dissolved in chloroform, and the layers were separated using pure water. The organic layer was further washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I12) (yield 21%).

[0329] The compound was identified by FDMS measurement (FDMS: 466).

[0330] Synthesis 7-3 Synthesis of compound (A075)

[0331]

[0332] Under a nitrogen atmosphere, intermediate I12 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated into pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A075) (yield 61%).

[0333] The compound was identified by FDMS measurement (FDMS: 898).

[0334] Example 7B Evaluation of Refractive Index of Compound (A075) The refractive index of compound (A075) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0335] Example 7C Evaluation of Transmittance of Compound (A075) The transmittance of compound (A075) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0336] Example 7D Low refractive index material: Evaluation of element using compound (A075) in capping layer An element using compound (A075) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0337] Example 8A Synthesis of Compound (A081) Synthesis 8-1 Synthesis of Intermediate (I13)

[0338]

[0339] Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), 3,5-dichloro-4-phenylboronic acid (pinacol) (12.0 mmol), and intermediate I6 (10.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 12 hours. After cooling to room temperature, the solution was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target intermediate (I13) (yield 48%).

[0340] The compound was identified by FDMS measurement (FDMS: 839).

[0341] Synthesis 8-2 Synthesis of compound (A081)

[0342]

[0343] Under a nitrogen atmosphere, tripotassium phosphate (45.0 mmol), palladium acetate (0.2 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (0.4 mmol), 1-adamantyl-4-phenylboronic acid (pinacol) (30.0 mmol), and intermediate I13 (12.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the solution was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A081) (yield 26%).

[0344] The compound was identified by FDMS measurement (FDMS: 1191).

[0345] Example 8B Evaluation of Refractive Index of Compound (A081) The refractive index of compound (A081) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0346] Example 8C Evaluation of Transmittance of Compound (A081) The transmittance of compound (A081) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0347] Example 8D Low refractive index material: Evaluation of element using compound (A081) in capping layer An element using compound (A081) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0348] Example 9A Synthesis of Compound (A083) Synthesis 9-1 Synthesis of Intermediate (I14)

[0349]

[0350] 3,5-Diamino-1-adamantanol (30.0 mmol) and 1-phenyladamantane (30.0 mmol) were dissolved in acetic acid (30 ml) and cooled to 0°C with ice water. Next, sulfuric acid (20 ml) was slowly added dropwise. After the addition was completed, the mixture was heated at 80°C for 24 hours. After cooling to room temperature, the mixture was neutralized with aqueous sodium hydroxide solution while cooling with water to obtain a solid. The solid was dissolved in chloroform, and the layers were separated using pure water. The organic layer was further washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I14) (yield 35%).

[0351] The compound was identified by FDMS measurement (FDMS: 376).

[0352] Synthesis 9-2 Synthesis of compound (A083)

[0353]

[0354] Under a nitrogen atmosphere, intermediate I14 (5.0 mmol), perfluorotoluene (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A083) (yield 50%).

[0355] The compound was identified by FDMS measurement (FDMS: 1240).

[0356] Example 9B Evaluation of Refractive Index of Compound (A083) The refractive index of compound (A083) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0357] Example 9C Evaluation of Transmittance of Compound (A083) The transmittance of compound (A083) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0358] Example 9D Low refractive index material: Evaluation of element using compound (A083) in capping layer An element using compound (A083) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the luminescence characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0359] Example 10A Synthesis of Compound (A088) Synthesis 10-1 Synthesis of Intermediate (I15)

[0360]

[0361] Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), 1-adamantyl-4-phenylboronic acid (pinacol) (15.0 mmol), and 2,6-diamino-4-bromopyridine (10.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the solution was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target intermediate (I15) (yield 51%).

[0362] The compound was identified by FDMS measurement (FDMS: 319).

[0363] Synthesis 10-2 Synthesis of compound (A088)

[0364]

[0365] Under a nitrogen atmosphere, intermediate I15 (5.0 mmol), perfluoropyridine (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 80°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A088) (yield 50%).

[0366] The compound was identified by FDMS measurement (FDMS: 915).

[0367] Example 10B Evaluation of Refractive Index of Compound (A088) The refractive index of compound (A088) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0368] Example 10C Evaluation of Transmittance of Compound (A088) The transmittance of compound (A088) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0369] Example 10D Low refractive index material: Evaluation of element using compound (A088) in capping layer An element using compound (A088) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0370] Example 11A Synthesis of Compound (A089) Synthesis 11-1 Synthesis of Intermediate (I16)

[0371]

[0372] Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), 1-adamantyl-4-phenylboronic acid (pinacol) (12.0 mmol), and 1-bromo-3,5-dichlorobenzene (10.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the solution was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target intermediate (I16) (yield 61%).

[0373] The compound was identified by FDMS measurement (FDMS: 356).

[0374] Synthesis 11-2 Synthesis of intermediate (I17)

[0375]

[0376] Under a nitrogen atmosphere, 2-aminodibenzofuran (20.0 mmol), intermediate I16 (8.0 mmol), sodium t-butoxide (20.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target intermediate (I17) (yield 58%).

[0377] The compound was identified by FDMS measurement (FDMS: 650).

[0378] Synthesis 11-3 Synthesis of compound (A089)

[0379]

[0380] Under a nitrogen atmosphere, intermediate I17 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 10°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A089) (yield 61%).

[0381] The compound was identified by FDMS measurement (FDMS: 1082).

[0382] Example 11B Evaluation of Refractive Index of Compound (A089) The refractive index of compound (A089) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0383] Example 11C Evaluation of Transmittance of Compound (A089) The transmittance of compound (A089) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0384] Example 11D Low refractive index material: Evaluation of element using compound (A089) in capping layer An element using compound (A089) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the luminescence characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0385] Example 12A Synthesis of Compound (A091) Synthesis 12-1 Synthesis of Intermediate (I18)

[0386]

[0387] Under a nitrogen atmosphere, 2-amino-9,9-dimethylfluorene (20.0 mmol), intermediate I16 (8.0 mmol), sodium t-butoxide (20.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I18) (yield 67%).

[0388] The compound was identified by FDMS measurement (FDMS: 702).

[0389] Synthesis 12-2 Synthesis of compound (A091)

[0390]

[0391] Under a nitrogen atmosphere, intermediate I18 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated into pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A091) (yield 61%).

[0392] The compound was identified by FDMS measurement (FDMS: 1134).

[0393] Example 12B Evaluation of Refractive Index of Compound (A091) The refractive index of compound (A091) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0394] Example 12C Evaluation of Transmittance of Compound (A091) The transmittance of compound (A091) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0395] Example 12D Low refractive index material: Evaluation of element using compound (A091) in capping layer An element using compound (A091) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0396] Example 13A Synthesis of Compound (A092) Synthesis 13-1 Synthesis of Intermediate (I19)

[0397]

[0398] Under a nitrogen atmosphere, aniline (20.0 mmol), intermediate I16 (20.0 mmol), sodium t-butoxide (20.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I19) (yield 23%).

[0399] The compound was identified by FDMS measurement (FDMS: 413).

[0400] Synthesis 13-2 Synthesis of intermediate (I20)

[0401]

[0402] Under a nitrogen atmosphere, 9-aminophenanthrene (15.0 mmol), intermediate I19 (10.0 mmol), sodium t-butoxide (12.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I20) (yield 61%).

[0403] The compound was identified by FDMS measurement (FDMS: 570).

[0404] Synthesis 13-3 Synthesis of compound (A092)

[0405]

[0406] Under a nitrogen atmosphere, intermediate I20 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A092) (yield 61%).

[0407] The compound was identified by FDMS measurement (FDMS: 1002).

[0408] Example 13B Evaluation of Refractive Index of Compound (A092) The refractive index of compound (A092) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0409] Example 13C Evaluation of Transmittance of Compound (A092) The transmittance of compound (A092) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0410] Example 13D Low refractive index material: Evaluation of element using compound (A092) in capping layer An element using compound (A092) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0411] Example 14A Synthesis of Compound (A093) Synthesis 14-1 Synthesis of Intermediate (I21)

[0412]

[0413] Under a nitrogen atmosphere, 6-amino-2-methylquinoline (15.0 mmol), intermediate I19 (10.0 mmol), sodium t-butoxide (12.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I21) (yield 53%).

[0414] The compound was identified by FDMS measurement (FDMS: 535).

[0415] Synthesis 14-2 Synthesis of compound (A093)

[0416]

[0417] Under a nitrogen atmosphere, intermediate I21 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A093) (yield 61%).

[0418] The compound was identified by FDMS measurement (FDMS: 967).

[0419] Example 14B Evaluation of Refractive Index of Compound (A093) The refractive index of compound (A093) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0420] Example 14C Evaluation of Transmittance of Compound (A093) The transmittance of compound (A093) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0421] Example 14D Low refractive index material: Evaluation of element using compound (A093) in capping layer An element using compound (A093) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the luminescence characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0422] Example 15A Synthesis of Compound (A095) Synthesis 15-1 Synthesis of Intermediate (I22)

[0423]

[0424] Under a nitrogen atmosphere, 2-aminodibenzothiophene (15.0 mmol), intermediate I19 (10.0 mmol), sodium t-butoxide (12.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I22) (yield 59%).

[0425] The compound was identified by FDMS measurement (FDMS: 576).

[0426] Synthesis 15-2 Synthesis of compound (A095)

[0427]

[0428] Under a nitrogen atmosphere, intermediate I22 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated into pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A095) (yield 67%).

[0429] The compound was identified by FDMS measurement (FDMS: 1008).

[0430] Example 15B Evaluation of Refractive Index of Compound (A095) The refractive index of compound (A095) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0431] Example 15C Evaluation of Transmittance of Compound (A095) The transmittance of compound (A095) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0432] Example 15D Low refractive index material: Evaluation of element using compound (A095) in capping layer An element using compound (A095) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0433] Example 16A Synthesis of Compound (A099) Synthesis 16-1 Synthesis of Intermediate (I23)

[0434]

[0435] Under a nitrogen atmosphere, intermediate I2 (15.0 mmol), perfluorobiphenyl (60.0 mmol), and cesium carbonate (50 mmol) were suspended in a mixed solvent of dimethyl sulfoxide (50 mL) and CPME (10 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I23) (yield 22%).

[0436] The compound was identified by FDMS measurement (FDMS: 946).

[0437] Synthesis 16-1 Synthesis of compound (A099)

[0438]

[0439] Under a nitrogen atmosphere, intermediate I23 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated into pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A099) (yield 61%).

[0440] The compound was identified by FDMS measurement (FDMS: 1378).

[0441] Example 16B Evaluation of Refractive Index of Compound (A099) The refractive index of compound (A099) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0442] Example 16C Evaluation of Transmittance of Compound (A099) The transmittance of compound (A099) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0443] Example 16D Low refractive index material: Evaluation of element using compound (A099) in capping layer An element using compound (A099) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0444] Example 17A Synthesis of Compound (A109) Synthesis 17-1 Synthesis of Intermediate (I24)

[0445]

[0446] Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), 2-chloro-5-pyridylboronic acid (pinacol) (15.0 mmol), and intermediate I6 (10.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target intermediate (I24) (yield 46%).

[0447] The compound was identified by FDMS measurement (FDMS: 806).

[0448] Synthesis 17-2 Synthesis of compound (A109)

[0449]

[0450] Under a nitrogen atmosphere, tripotassium phosphate (45.0 mmol), palladium acetate (0.2 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (0.4 mmol), 1-adamantyl-3-phenylboronic acid (pinacol) (30.0 mmol), and intermediate I24 (24.0 mmol) were dissolved in THF (100 ml) and water (100 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the solution was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A109) (yield 35%).

[0451] The compound was identified by FDMS measurement (FDMS: 982).

[0452] Example 17B Evaluation of Refractive Index of Compound (A109) The refractive index of compound (A109) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0453] Example 17C Evaluation of Transmittance of Compound (A109) The transmittance of compound (A109) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0454] Example 17D Low refractive index material: Evaluation of element using compound (A109) in capping layer An element using compound (A109) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0455] Example 18A Synthesis of Compound (A118)

[0456]

[0457] Under a nitrogen atmosphere, sodium hydride (15.0 mmol) was suspended in tetrahydrofuran (20 ml) and stirred at 0°C. To this suspension was added dropwise a solution of intermediate I12 (6.0 mmol) in tetrahydrofuran over 20 minutes. After completion of the dropwise addition, the mixture was returned to room temperature and stirred for 2 hours. Furthermore, to this suspension was added dropwise a solution of cyanuric chloride (15.0 mmol) in tetrahydrofuran (40 ml) over 20 minutes at 0°C. After completion of the dropwise addition, the mixture was stirred at 60°C for 5 hours. Under a nitrogen atmosphere, sodium hydride (35.0 mmol) was suspended in tetrahydrofuran (20 ml) in the reactor and stirred at 0°C. To this suspension was added dropwise 2,2-difluoroethanol (30.0 mmol) over 20 minutes. After completion of the dropwise addition, the mixture was returned to room temperature and stirred for 30 minutes, and the reaction solution was added dropwise over 20 minutes. After completion of the dropwise addition, the mixture was stirred at 60°C for 5 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography to obtain the target compound (A118) (yield 35%).

[0458] The compound was identified by FDMS measurement (FDMS: 944).

[0459] Example 18B Evaluation of Refractive Index of Compound (A118) The refractive index of compound (A118) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0460] Example 18C Evaluation of Transmittance of Compound (A118) The transmittance of compound (A118) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0461] Example 18D Low refractive index material: Evaluation of element using compound (A118) in capping layer An element using compound (A118) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the light-emitting characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0462] Example 19A Synthesis of Compound (A120) Synthesis 19-1 Synthesis of Intermediate (I25)

[0463]

[0464] Under a nitrogen atmosphere, aniline (20.0 mmol), intermediate I16 (8.0 mmol), sodium t-butoxide (6.1 mmol), sodium t-butoxide (20.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I18) (yield 81%).

[0465] The compound was identified by FDMS measurement (FDMS: 470).

[0466] Synthesis 19-2 Synthesis of compound (A120)

[0467]

[0468] Under a nitrogen atmosphere, sodium hydride (15.0 mmol) was suspended in tetrahydrofuran (20 ml) and stirred at 0°C. To this suspension was added dropwise a solution of intermediate I25 (6.0 mmol) in tetrahydrofuran over 20 minutes. After completion of the dropwise addition, the mixture was returned to room temperature and stirred for 2 hours. Furthermore, to this suspension was added dropwise a solution of cyanuric chloride (15.0 mmol) in tetrahydrofuran (40 ml) over 20 minutes at 0°C. After completion of the dropwise addition, the mixture was stirred at 60°C for 5 hours. Under a nitrogen atmosphere, sodium hydride (35.0 mmol) was suspended in tetrahydrofuran (20 ml) in the reactor and stirred at 0°C. To this suspension was added dropwise 2,2,2-trifluoroethanol (30.0 mmol) over 20 minutes. After completion of the dropwise addition, the mixture was returned to room temperature and stirred for 30 minutes, and the reaction solution was added dropwise over 20 minutes. After completion of the dropwise addition, the mixture was stirred at 60°C for 5 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography to obtain the target compound (A120) (yield 39%).

[0469] The compound was identified by FDMS measurement (FDMS: 1020).

[0470] Example 19B Evaluation of Refractive Index of Compound (A120) The refractive index of compound (A120) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0471] Example 19C Evaluation of Transmittance of Compound (A120) The transmittance of compound (A120) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0472] Example 19D Low refractive index material: Evaluation of element using compound (A120) in capping layer An element using compound (A120) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the luminescence characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0473] Example 20A Synthesis of Compound (A120) Synthesis 20-1 Synthesis of Intermediate (I26)

[0474]

[0475] Under a nitrogen atmosphere, 4-adamantylaniline (20.0 mmol), intermediate I16 (8.0 mmol), sodium t-butoxide (20.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 18 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target intermediate (I26) (yield 68%).

[0476] The compound was identified by FDMS measurement (FDMS: 738).

[0477] Synthesis 20-2 Synthesis of compound (A032)

[0478]

[0479] Under a nitrogen atmosphere, intermediate I26 (5.0 mmol), perfluorotoluene (50 mmol), and cesium carbonate (25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100°C for 24 hours. After cooling to room temperature, the mixture was separated into pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A032) (yield 61%).

[0480] The compound was identified by FDMS measurement (FDMS: 1170).

[0481] Example 20B Evaluation of Refractive Index of Compound (A032) The refractive index of compound (A032) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0482] Example 20C Evaluation of Transmittance of Compound (A032) The transmittance of compound (A032) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0483] Example 20D Low refractive index material: Evaluation of element using compound (A032) in capping layer An element using compound (A032) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the luminescence characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0484] Example 21A Synthesis of Compound (A125) Synthesis 21-1 Synthesis of Intermediate (I26)

[0485]

[0486] Under a nitrogen atmosphere, 4-methylaniline (20.0 mmol), intermediate I16 (8.0 mmol), sodium t-butoxide (20.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.4 ml), palladium(II) acetate (0.10 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 18 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I26) (yield 68%).

[0487] The compound was identified by FDMS measurement (FDMS: 498).

[0488] Synthesis 21-2 Synthesis of compound (A125)

[0489]

[0490] Under a nitrogen atmosphere, 3,5-difluoro-bromobenzene (20.0 mmol), intermediate I26 (8.0 mmol), sodium t-butoxide (20.0 mmol), a 25 wt % xylene solution of tri(tert-butyl)phosphine (0.2 ml), palladium(II) acetate (0.05 mmol), and o-xylene (35 ml) were added, followed by stirring at 140°C for 18 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target compound (A125) (yield 32%).

[0491] The compound was identified by FDMS measurement (FDMS: 694).

[0492] Example 21B Evaluation of Refractive Index of Compound (A125) The refractive index of compound (A125) was measured using the same method as in Example 1B. The results are shown in Table 1.

[0493] Example 21C Evaluation of Transmittance of Compound (A125) The transmittance of compound (A125) was measured in the same manner as in Example 1C. The results are shown in Table 1.

[0494] Example 21D Low refractive index material: Evaluation of element using compound (A125) in capping layer An element using compound (A125) in the low refractive index layer 92 was prepared using the same method as in Example 1D, and the luminescence characteristics were evaluated using the same method as in Example 1D. The results are shown in Table 1.

[0495] Comparative Example 0D In Comparative Example 0D, an organic electroluminescent device was produced in the same manner as in Example 1D, except that the low refractive index layer 92 was not formed. The light-emitting characteristics of the produced device were plotted in the same manner as in Example 1D. The value of the current efficiency (lm / A; light-emitting efficiency) was set to 100. The results are shown in Table 2.

[0496] Comparative Example 1B Refractive Index Evaluation of Compound (X1)

[0497]

[0498] The refractive index of compound (X1) represented by the above formula was measured in the same manner as in Example 1B. The refractive index of compound (X1) was 1.92 or less in the range of 450 to 900 nm. The results are shown in Table 2.

[0499] Comparative Example 1C: Evaluation of transmittance of compound (X1) The transmittance of compound X1 was measured in the same manner as in Example 1C. The transmittance of compound (X1) was 90% or more in the range of 450 to 900 nm. The results are shown in Table 2.

[0500] Comparative Example 1D: Evaluation of Element An organic electroluminescence element was produced in the same manner as in Element Example 1D, except that compound (X1) was used in place of compound (A010) in the low refractive index layer 92. The current efficiency (lm / A; luminous efficiency) values ​​were expressed as relative values ​​when the value of Comparative Example 1D was taken as 100. The results are shown in Table 2 and FIG. 5.

[0501] Comparative Example 1B Refractive Index Evaluation of Compound (X2)

[0502]

[0503] The refractive index of compound (X2) represented by the above formula was measured in the same manner as in Example 1B. The refractive index of compound (X2) was 1.85 or less in the range of 450 to 900 nm. The results are shown in Table 2.

[0504] Comparative Example 2C: Evaluation of transmittance of compound (X2) The transmittance of compound X2 was measured in the same manner as in Example 2C. The transmittance of compound (X2) was 90% or more in the range of 450 to 900 nm. The results are shown in Table 2.

[0505]

[0506]

[0507] It is clear from Tables 1 and 2 that the organic electroluminescent element using a low refractive index material as the low refractive index layer has superior luminous efficiency compared to the element of the comparative example.

[0508] Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

[0509] The entire contents of the specification, claims, drawings and abstract of Japanese Patent Application No. 2024-135419 filed on August 14, 2024 are hereby incorporated by reference as the disclosure of the present invention.

[0510] 1. Substrate 2. Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6. Electron transport layer 7. Electron injection layer 8. Cathode 9. Capping layer 91. High refractive index layer 92. Low refractive index layer 100. Organic electroluminescence element 41. First hole transport layer 42. Second hole transport layer 61. Hole blocking layer

Claims

1. An amine compound represented by the following formula (2): In formula (2), each A independently represents a monocyclic, linked ring, or fused ring trivalent to tetravalent aromatic hydrocarbon group having 6 to 13 carbon atoms which may be substituted with a fluorine atom, a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, a monocyclic, linked ring, or fused ring trivalent to tetravalent heteroaromatic group having 3 to 11 carbon atoms which may be substituted with a fluorine atom, or a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a cyclic trivalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted with a fluorine atom. In formula (2), each B independently represents a monocyclic, linked ring, or fused ring divalent to trivalent aromatic hydrocarbon group having 6 to 13 carbon atoms, a monocyclic, linked ring, or fused ring divalent to trivalent heteroaromatic group having 3 to 11 carbon atoms, or a cyclic divalent to trivalent aliphatic hydrocarbon group having 3 to 18 carbon atoms. In formula (2), each E independently represents a monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, a monovalent heteroaromatic group having 3 to 26 carbon atoms, a monovalent heteroaromatic group having 3 to 26 carbon atoms, or a cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms. In formula (2), l represents an integer from 1 to 4. In formula (2), m represents an integer from 0 to 2. In formula (2), n represents 1 or 2. In formula (2), at least one E represents an aromatic hydrocarbon group, heteroaromatic group, or aliphatic hydrocarbon group constituting E, which is substituted with one or more fluorine atoms. In formula (2), B and E each independently may be substituted with a phenyl group, naphthyl group, pyridyl group, triazyl group, methyl group, methoxy group, adamantyl group, or fluorine atom, or the substituents of B and E may be further substituted with one or more groups selected from the group consisting of these groups.

2. The amine compound according to claim 1, wherein the compounds A in the formula (2) that provide a monocyclic, linked, or fused ring trivalent or tetravalent aromatic hydrocarbon group having 6 to 13 carbon atoms are each independently: (A1) benzene, biphenyl, naphthalene, or fluorene; or (A1') the compound represented by (A1) substituted with one or more fluorine atom groups.

3. The amine compound according to claim 1, wherein the compounds which provide a monocyclic, linked, or fused trivalent to tetravalent heteroaromatic group having 3 to 11 carbon atoms, represented by A in the above formula (2), are each independently: (A5) pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole; or (A5') the compound represented by (A5) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom.

4. The amine compound according to claim 1, wherein the compounds which provide the cyclic trivalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by A in the above formula (2), are each independently: (A10) adamantane, diamantane, norbornene, or cyclohexane; or (A10') the compound represented by (A10) is substituted with a phenyl group, a pentafluorophenyl group, a pyridyl group, a tetrafluoropyridyl group, a methyl group, an adamantyl group, or a fluorine atom.

5. The amine compound according to claim 1, wherein the compounds which provide a monocyclic, linked, or fused ring divalent or trivalent aromatic hydrocarbon group having 6 to 13 carbon atoms, represented by B in the above formula (2), are each independently: (B1) benzene, biphenyl, naphthalene, or fluorene; or (B1') the compound represented by (B1) is substituted with a phenyl group, naphthyl group, pyridyl group, triazyl group, methyl group, methoxy group, adamantyl group, or fluorine atom (wherein the substituents on the compound represented by (B1) may be further substituted with one or more groups selected from the group consisting of the above groups).

6. The amine compound according to claim 1, wherein the compounds which provide the monocyclic, linked, or fused divalent or trivalent heteroaromatic group having 3 to 11 carbon atoms, represented by B in the above formula (2), are each independently: (B5) pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole; or (B5') the compound represented by (B5) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituents on the compound represented by (B5) may be further substituted with one or more groups selected from the group consisting of the above groups).

7. The amine compound according to claim 1, wherein the compounds which provide the cyclic divalent or trivalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by B in the above formula (2), are each independently: (B10) adamantane, diamantane, norbornene, or cyclohexane; or (B10') the compound represented by (B10) is substituted with a phenyl group, naphthyl group, pyridyl group, triazyl group, methyl group, methoxy group, adamantyl group, or fluorine atom (wherein the substituents on the compound represented by (B10) may be further substituted with one or more groups selected from the group consisting of the above groups).

8. In the above formula (2), the compounds that provide a monovalent aromatic hydrocarbon group of 6 to 26 carbon atoms, represented by E, are each independently: (E1) benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or a structure in which these compounds are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; or (E1') The amine compound according to claim 1, wherein the compound represented by (E1) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituent possessed by the compound represented by (E1) may be further substituted with one or more groups selected from the group consisting of the aforementioned groups).

9. In the above formula (2), the compounds that provide a monovalent heteroaromatic group having 6 to 26 carbon atoms and represented by E, which is a single ring, a linked ring, or a fused ring, are each independently: (E8) pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or a structure in which one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these compounds; or (E8') The amine compound according to claim 1, wherein the compound represented by (E8) is substituted with a phenyl group, a naphthyl group, a pyridyl group, a triazyl group, a methyl group, a methoxy group, an adamantyl group, or a fluorine atom (wherein the substituent possessed by the compound represented by (E8) may be further substituted with one or more groups selected from the group consisting of the aforementioned groups).

10. The amine compound according to claim 1, wherein the compounds which provide the cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, represented by E in the above formula (2), are each independently: (E14) adamantane, diamantane, norbornene, or cyclohexane; or (E14') the compound represented by (E14) is substituted with a phenyl group, naphthyl group, pyridyl group, triazyl group, methyl group, methoxy group, adamantyl group, or fluorine atom (wherein the substituent on the compound represented by (E14) may be further substituted with one or more groups selected from the group consisting of the above groups).

11. A capping layer material for an organic thin film device, comprising at least one compound selected from the group consisting of a compound represented by the following formula (1) and the amine compounds according to any one of claims 1 to 9: In formula (1), each X independently represents an optionally substituted tri- or tetravalent aromatic hydrocarbon group of a monocycle, linked ring, or fused ring having 6 to 26 carbon atoms, an optionally substituted tri- or tetravalent heteroaromatic group of a monocycle, linked ring, or fused ring having 3 to 26 carbon atoms, or an optionally substituted cyclic tri- or tetravalent aliphatic hydrocarbon group of 3 to 18 carbon atoms. In formula (1), each Y independently represents an optionally substituted di- or trivalent aromatic hydrocarbon group of a monocycle, linked ring, or fused ring having 6 to 26 carbon atoms, an optionally substituted di- or trivalent monocycle, linked ring, or fused ring having 3 to 26 carbon atoms, or an optionally substituted cyclic di- or trivalent aliphatic hydrocarbon group of 3 to 18 carbon atoms. In formula (1), each Z independently represents an optionally substituted monovalent aromatic hydrocarbon group of 6 to 26 carbon atoms, which is a monocyclic, linked ring, or fused ring, an optionally substituted monovalent heteroaromatic group of 3 to 26 carbon atoms, or an optionally substituted cyclic monovalent aliphatic hydrocarbon group of 3 to 18 carbon atoms. In formula (1), a represents an integer of 1 to 4. In formula (1), b represents an integer of 0 to 2. In formula (1), c represents 1 or 2. In formula (1), at least one E is substituted with a fluorine atom.

12. The capping layer material of claim 11, wherein the organic thin film device is an organic electroluminescent device.

13. An organic electroluminescence device having at least an anode, a light-emitting layer, a cathode, and a capping layer in this order, wherein the capping layer contains the capping layer material according to claim 11 or the amine compound according to any one of claims 1 to 9.

14. An organic electroluminescence device having at least an anode, a light-emitting layer, a cathode, and a capping layer in this order, the capping layer being composed of at least a high-refractive index layer and a low-refractive index layer, and the low-refractive index layer containing the capping layer material defined in claim 11 or the amine compound defined in any one of claims 1 to 9.

Images