WO2023171544A1 - Poudre mélangée, procédé de fabrication de poudre mélangée, composition, élément électroluminescent organique et procédé de fabrication d'élément électroluminescent organique - Google Patents

Poudre mélangée, procédé de fabrication de poudre mélangée, composition, élément électroluminescent organique et procédé de fabrication d'élément électroluminescent organique Download PDF

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WO2023171544A1
WO2023171544A1 PCT/JP2023/007955 JP2023007955W WO2023171544A1 WO 2023171544 A1 WO2023171544 A1 WO 2023171544A1 JP 2023007955 W JP2023007955 W JP 2023007955W WO 2023171544 A1 WO2023171544 A1 WO 2023171544A1
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substituted
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organic compound
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哲也 増田
聡美 田崎
ヨングク リー
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
    • C23C14/06—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the coating material
    • C23C14/12—Organic material
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight

Definitions

  • the present invention relates to a mixed powder, a method for producing a mixed powder, a composition, an organic electroluminescent device, and a method for producing an organic electroluminescent device.
  • Vacuum evaporation is generally used as a method for forming organic layers constituting organic electroluminescent devices (hereinafter also referred to as "organic EL devices"), and to form a mixed layer consisting of multiple components
  • organic EL devices organic electroluminescent devices
  • a co-evaporation method has been used in which each component is vaporized from a separate vapor deposition source (crucible) and vapor-deposited at the same time.
  • a co-evaporation method it is possible to control the temperature independently for each evaporation source, so by controlling the amount of vaporization of each material, it is easy to adjust the mixing ratio in the evaporation film, and it is also possible to continuously Even when vapor deposition is performed, it is possible to form a film with a fixed mixing ratio.
  • the use of multiple vapor deposition sources complicates the manufacturing process, leading to problems such as increased manufacturing burden and cost.
  • Patent Documents 1 and 2 disclose composite organic electroluminescent materials in which an organic material and an organometallic complex are bonded to each other as a mixed material used in flash vapor deposition.
  • An object of the present invention is to provide a premix material that enables vapor deposition in which fluctuations in the component ratio in a mixed film during the film formation process are suppressed in a vapor deposition process using the premix material.
  • premix technology can overcome the above-mentioned disadvantages of co-evaporation, it is difficult to form a deposited film with a desired mixing ratio compared to co-evaporation, and it is difficult to deposit a film with a desired mixing ratio when performing continuous vapor deposition on multiple substrates.
  • the mixing ratio varied depending on the substrate, making it difficult to obtain a constant quality.
  • the vapor deposition process continues continuously over several weeks to several months, so it is important to be able to manufacture a mixed film at a stable ratio over a long period of time.
  • the above-mentioned problems in premix technology are important issues to be solved.
  • the present inventors focused on the particle size and particle size distribution of the mixed powder (premix material), and determined that the volume median diameter of the powder should be within a specific numerical range or that the particle size distribution
  • the inventors have discovered that the above problem can be solved by reducing the standard deviation to a specific value or less, and have completed the present invention.
  • the following mixed powder and the like are provided. 1.
  • a mixed powder for vacuum deposition comprising a first organic compound and a second organic compound, The volume median diameter is 10 ⁇ m or more and 60 ⁇ m or less, Mixed powder.
  • a mixed powder for vacuum deposition comprising a first organic compound and a second organic compound,
  • the standard deviation of the particle size distribution is 100 ⁇ m or less, Mixed powder. 3.
  • a composition comprising a first organic compound and a second organic compound, Differential scanning calorific value of a mixed powder containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition and having a volume median diameter of 10 ⁇ m or more and 40 ⁇ m or less.
  • the endothermic peak temperature P1 measured in the measurement and the volume median diameter containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition are more than 60 ⁇ m and 90 ⁇ m.
  • a composition in which the following endothermic peak temperature P2 measured in differential scanning calorimetry of the mixed powder satisfies the following formula (1).
  • a composition comprising a first organic compound and a second organic compound, In differential scanning calorimetry of a mixed powder containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition and having a standard deviation of particle size distribution of 50 ⁇ m or less.
  • the measured endothermic peak temperature P11 and the standard deviation of the particle size distribution containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition are more than 100 ⁇ m.
  • a composition in which an endothermic peak temperature P12 measured in differential scanning calorimetry of mixed powder satisfies the following formula (11).
  • the present invention in a vapor deposition process using a premix material, it is possible to provide a premix material that enables vapor deposition in which fluctuations in the component ratio in a mixed film during the film formation process are suppressed.
  • FIG. 1 is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention.
  • FIG. 6 is a diagram showing the results of differential scanning calorimetry in Experimental Example 2.
  • the mixed powder includes a first organic compound (hereinafter also referred to as “first component”) and a second organic compound (hereinafter also referred to as “second component”). This is a mixed powder for vapor deposition.
  • the volume median diameter of the mixed powder is 10 ⁇ m or more and 60 ⁇ m or less (hereinafter also referred to as “first premix material”).
  • the balance between the vaporization amount of the first component and the second component can be maintained for a long time, and especially when the material is heated continuously for multiple substrates.
  • the above effects are not intended to mean that the film can be formed at a constant ratio on all substrates subjected to the continuous vapor deposition process. Even when using the mixed powder according to one embodiment of the present invention, it can be expected that the component ratio will fluctuate somewhat, especially in the final stage of the process. It means that it can be improved.
  • the mixed powder When performing a continuous deposition process using a meltable mixed powder (premix material), the mixed powder is usually melted in a deposition source (crucible), then vaporized, and deposited on a substrate. At this time, since the deposition material passes through a liquid state, it has not been thought that the size of the particles constituting the mixed powder would affect the results of the continuous deposition process. However, as a result of studies conducted by the present inventors, it was found that by using a mixed powder having a specific volume median diameter, a clear change occurs in the results of the continuous vapor deposition process. That is, by using such a mixed powder, fluctuations in the vapor deposition ratio during execution of the process were suppressed, and the stability of the component ratios was greatly improved.
  • the difference in component ratio between the mixed powder and the deposited film could be reduced, making it possible to achieve highly reproducible deposition.
  • the reason for this effect is not necessarily clear, it is possible to make the vapor deposition characteristics and thermal behavior of the particles that make up the mixed powder more homogeneous by making the particles finer and adjusting the volume median diameter to a specific range. This is thought to be due to the fact that more integrated melting and vaporization became possible.
  • Each structure of the first premix material will be explained below.
  • the volume median diameter of the first premix material is 10 ⁇ m or more and 60 ⁇ m or less.
  • the volume median diameter is the median diameter of a volume-based cumulative distribution (particle diameter when the cumulative frequency is 50%).
  • the volume median diameter will also be referred to as D50 .
  • D50 is measured by the method described in the Examples.
  • the volume median diameter of the first premix material is 60 ⁇ m or less, which is typically a fairly small particle size compared to conventional deposition powders. Thereby, as described above, the stability of the component ratios in the continuous vapor deposition process can be greatly improved.
  • the volume median diameter of the first premix material may be 55 ⁇ m or less, 50 ⁇ m or less, 45 ⁇ m or less, or 40 ⁇ m or less.
  • the volume median diameter of the first premix material is 10 ⁇ m or more. By ensuring a certain size, it is possible to prevent the powder from rolling up, and it is easy to handle. In one embodiment, the volume median diameter of the first premix material may be 15 ⁇ m or more, 20 ⁇ m or more, 25 ⁇ m or more, or 30 ⁇ m or more.
  • the volume median diameter of the first premix material is 20 ⁇ m or more and 50 ⁇ m or less.
  • the standard deviation of the particle size distribution in the first premix material is 100 ⁇ m or less.
  • the standard deviation of particle size distribution is an index indicating the distribution width of volume-based particle size distribution.
  • the standard deviation of particle size distribution is measured by the method described in Examples.
  • the powder usually has small variations in particle size and high homogeneity in particle size compared to conventional deposition powders.
  • Such a configuration can be expected to have the effect of making the vapor deposition characteristics and thermal behavior more homogeneous when the first premix material is subjected to a vapor deposition process.
  • the standard deviation of the particle size distribution in the first premix material may be 70 ⁇ m or less, 50 ⁇ m or less, or 30 ⁇ m or less.
  • the lower limit of the standard deviation of the particle size distribution in the first premix material is not particularly limited, but is usually 1 ⁇ m or more.
  • the first premix material may be a material consisting of particles in which the first component and the second component are contained in one particle, or a mixture of particles consisting of the first component and particles consisting of the second component. It may be. Alternatively, it may be in the form of pellets obtained by compression molding a mixed powder.
  • the first premix material is a mixture of particles of the first component and particles of the second component. That is, it includes particles consisting only of the first component (hereinafter also referred to as “first powder”) and powder consisting only of the second component (hereinafter also referred to as “second powder”) (hereinafter referred to as “first powder”). , this aspect is also referred to as “first premix material (2)").
  • the first powder in the first premix material (2), has a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less, and the second powder has a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less. It is. By aligning the particle sizes of the first powder and the second powder to closer values, it is possible to expect a greater effect of improving the stability of the continuous vapor deposition process described above.
  • the first powder has a volume median diameter of 20 ⁇ m or more and 50 ⁇ m or less
  • the second powder has a volume median diameter of 20 ⁇ m or more and 50 ⁇ m or less.
  • the standard deviation of the particle size distribution of the first powder is 100 ⁇ m or less, and the standard deviation of the particle size distribution of the second powder is 100 ⁇ m or less.
  • the standard deviation of the particle size distribution of the first powder is 50 ⁇ m or less, and the standard deviation of the particle size distribution of the second powder is 50 ⁇ m or less.
  • the mixed powder of the first premix material (2) consists only of the first powder and the second powder, or consists essentially of the first powder and the second powder. Consists only of powder. In the latter case, particles containing the first component and the second component may be inevitably included in one particle. In one embodiment, 80% by mass or more, 90% by mass or more, 95% by mass or more, 99% by mass or more, or 99.9% by mass or more of the mixed powder related to the first premix material (2), or 100% by mass or more, The mass % is the first powder and the second powder.
  • the first premix material includes particles to which the first component and the second component are adhered, one of the first component and the second component, and the like. is free or substantially free of particles coated with the other, and particles embedded in one of the first component and the second component. "Substantially free of” includes cases where these particles are unavoidably mixed.
  • the first premix material includes particles in which the first component and the second component are bonded together, particles in which one of the first component and the second component is coated with the other, and particles in which the first component and the second component are coated with the other.
  • the content (total amount) of particles embedded in one of the components is 1% by mass or less, 0.5% by mass or less, 0.1% by mass or less, or 0% by mass.
  • the first premix material can be used in a vacuum evaporation method, that is, it can be applied to any technical field involving vacuum evaporation of organic compounds to form films.
  • the first premix material is not for flash deposition.
  • the first premix material is an organic semiconductor material, such as an organic EL device material, an organic transistor material, or an organic solar cell material.
  • the mass ratio of the first component to the second component in the first premix material is 30-70:70-30 or 40-60:60-40. In one embodiment, the mass ratio of the second component to the sum of the first component and the second component in the first premix material is greater than 0% and less than or equal to 20%, more than 0% and less than or equal to 10%, or more than 0% and less than or equal to 5%. It is as follows.
  • the term "the first component and the second component are different compounds” includes cases where the chemical structural formulas (skeletons) are different from each other, and cases where the chemical structural formulas (skeletons) are the same but contain different isotopes. .
  • Isotope means atoms with the same atomic number but different numbers of neutrons.
  • benzene (C 6 H 6 ) and deuterated benzene (C 6 D 6 ) are mutually different compounds.
  • the compounds are also considered to be different if the number or arrangement of the isotopes differs from each other.
  • C 6 H 5 D 1 and C 6 D 6 have different numbers of isotopes, so they are different compounds from each other.
  • C 6 H 4 D 2 are the same, one compound has deuterium at the 1st and 2nd positions of the benzene ring, and the other has deuterium at the 1st and 3rd positions of the benzene ring.
  • Compounds are compounds that are different from each other because they have different isotopic configurations.
  • the first component and the second component are organic semiconductor materials, such as organic EL element materials, organic transistor materials, or organic solar cell materials.
  • the materials described in the below-mentioned [Method for manufacturing an organic EL element] can be used as appropriate.
  • examples thereof include an organic compound (host material of a light-emitting layer), a hole-transporting compound, and an electron-transporting compound for transporting charges to the luminescent compound.
  • examples of the dopant material for the light-emitting layer include a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence. Examples of the emission color include blue, green, and red.
  • the dopant material includes a blue phosphorescent compound.
  • the host material for the light-emitting layer is preferably an organic compound suitable for the above-mentioned dopant material, and examples thereof include a host material for a fluorescent light-emitting element, a host material for a phosphorescent light-emitting element, a host material for a blue phosphorescent light-emitting element, and the like.
  • the first component is a host material for the fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is a dopant material (fluorescent compound) for the fluorescent light emitting layer.
  • the first component is a host material for the fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is a host material for the fluorescent light emitting layer (host material for a fluorescent light emitting device).
  • the first component is a host material for a fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is a hole transporting compound.
  • the first component is a host material for a fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is an electron transporting compound.
  • the first component is a host material for a fluorescent light-emitting layer (host material for a fluorescent light-emitting device), and the second component is a hole-injecting compound.
  • the first component is a host material for a fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is an electron injection compound.
  • the first component is a host material for the phosphorescent layer (host material for a phosphorescent device), and the second component is a dopant material (phosphorescent compound) for the phosphorescent layer.
  • the first component is a host material for the phosphorescent layer (host material for a phosphorescent device), and the second component is a host material for the phosphorescent layer (host material for a phosphorescent device).
  • the first component is a host material for a phosphorescent layer (host material for a phosphorescent device), and the second component is a hole-transporting compound.
  • the first component is a host material for a phosphorescent layer (host material for a phosphorescent device), and the second component is an electron transporting compound.
  • the first component is a host material for a phosphorescent layer (host material for a phosphorescent device), and the second component is a hole-injecting compound.
  • the first component is a host material for a phosphorescent layer (host material for a phosphorescent device), and the second component is an electron injection compound.
  • the first component is a hole transporting compound and the second component is a dopant material for the emissive layer.
  • the first component is a hole-transporting compound
  • the second component is a host material for a fluorescent layer (host material for a fluorescent device).
  • the first component is a hole-transporting compound
  • the second component is a host material for a phosphorescent layer (host material for a phosphorescent device).
  • the first component is a hole transporting compound and the second component is a hole transporting compound.
  • the first component is a hole transporting compound and the second component is an electron transporting compound.
  • the first component is a hole-transporting compound and the second component is a hole-injecting compound.
  • the first component is a hole-transporting compound and the second component is an electron-injecting compound.
  • the first component is an electron transporting compound and the second component is a dopant material for the emissive layer.
  • the first component is an electron transporting compound
  • the second component is a host material for a fluorescent layer (host material for a fluorescent device).
  • the first component is an electron transporting compound
  • the second component is a host material for a phosphorescent layer (host material for a phosphorescent device).
  • the first component is an electron transporting compound and the second component is a hole transporting compound.
  • the first component is an electron transporting compound and the second component is an electron transporting compound.
  • the first component is an electron-transporting compound and the second component is a hole-injecting compound.
  • the first component is an electron transporting compound and the second component is an electron injecting compound.
  • the first component is a hole-injecting compound and the second component is a dopant material for the emissive layer.
  • the first component is a hole-injecting compound
  • the second component is a host material for a fluorescent layer (host material for a fluorescent device).
  • the first component is a hole-injecting compound
  • the second component is a host material for a phosphorescent layer (host material for a phosphorescent device).
  • the first component is a hole-injecting compound and the second component is a hole-transporting compound.
  • the first component is a hole-injecting compound and the second component is an electron-transporting compound.
  • the first component is a hole-injecting compound and the second component is a hole-injecting compound. In one embodiment, the first component is a hole-injecting compound and the second component is an electron-injecting compound. In one embodiment, the first component is an electron-injecting compound and the second component is a dopant material for the emissive layer. In one embodiment, the first component is an electron-injecting compound, and the second component is a host material for a fluorescent layer (host material for a fluorescent device). In one embodiment, the first component is an electron-injecting compound, and the second component is a host material for a phosphorescent layer (host material for a phosphorescent device).
  • the first component is an electron injection compound and the second component is a hole transport compound. In one embodiment, the first component is an electron-injecting compound and the second component is an electron-transporting compound. In one embodiment, the first component is an electron-injecting compound and the second component is a hole-injecting compound. In one embodiment, the first component is an electron-injecting compound and the second component is an electron-injecting compound. In one embodiment, the first component and the second component are not organometallic compounds. In one embodiment, the mixed powder does not include a phosphorescent compound. In one embodiment, the mixed powder is free of heavy metal complexes.
  • the compounds shown below can be used independently as the first organic compound and the second organic compound.
  • One or more sets of two or more adjacent ones of R 101 to R 110 bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring does not form a ring.
  • At least one of R 101 to R 110 is a monovalent group represented by the following formula (12).
  • R 101 to R 110 that do not form a substituted or unsubstituted saturated or unsaturated ring and are not monovalent groups represented by the following formula (12) are each independently: hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ) (where R 901 to R 907 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
  • each of the two or more R 901 to R 907 may be the same or different.
  • Ar 101 and Ar 102 are each independently, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 101 to L 103 are each independently, single bond, A substituted or unsubstituted arylene group having 6 to 30 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
  • Z is each independently CR a or N.
  • the A1 ring and the A2 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • R a 's When a plurality of R a 's exist, one or more adjacent sets of two or more of the plurality of R a 's are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted ring is formed. Does not form an unsubstituted saturated or unsaturated ring.
  • R b 's When a plurality of R b 's exist, one or more adjacent sets of two or more of the plurality of R b's are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted ring is formed. Does not form an unsubstituted saturated or unsaturated ring.
  • n21 and n22 are each independently an integer of 0 to 4.
  • the substituted or unsubstituted saturated or unsaturated ring-forming R a to R c are each independently: hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group
  • R 901 to R 907 are as defined in formula (11) above. ) (In formula (31), One or more pairs of adjacent two or more of R 301 to R 307 and R 311 to R 317 form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring does not form a ring.
  • the substituted or unsubstituted saturated or unsaturated ring-forming R 301 to R 307 and R 311 to R 317 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstit
  • R 321 and R 322 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are as defined in formula (11) above. )
  • Ring a, ring b, and ring c are each independently, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • R 401 and R 402 each independently combine with ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.
  • R 401 and R 402 which do not form a substituted or unsubstituted heterocycle are each independently, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • the r ring is a ring represented by formula (52) or formula (53) condensed at any position of adjacent rings.
  • the q ring and the s ring are each independently a ring represented by formula (54) that is fused at any position of an adjacent ring.
  • the p ring and the t ring are each independently a structure represented by formula (55) or formula (56) condensed at any position of an adjacent ring.
  • X 501 is an oxygen atom, a sulfur atom, or NR 502 .
  • the substituted or unsubstituted saturated or unsaturated ring-forming R 501 and R 502 are: hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring
  • R 901 to R 907 are as defined in formula (11) above.
  • Ar 501 and Ar 502 are each independently, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 501 is Substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms, Substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms, A substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • m1 is an integer from 0 to 2
  • m2 is an integer from 0 to 4
  • m3 is each independently an integer from 0 to 3
  • m4 is each independently an integer from 0 to 5.
  • the plurality of R 501s may be the same or different.
  • At least one set of R 601 and R 602 , R 602 and R 603 , and R 603 and R 604 combine with each other to form a divalent group represented by the following formula (62).
  • At least one set of R 605 and R 606 , R 606 and R 607 , and R 607 and R 608 combine with each other to form a divalent group represented by the following formula (63).
  • R 601 to R 604 those that do not form a divalent group represented by the above formula (62), and at least one of R 611 to R 614 are a monovalent group represented by the following formula (64) .
  • R 605 to R 608 those that do not form the divalent group represented by the above formula (63), and at least one of R 621 to R 624 are monovalent groups represented by the following formula (64).
  • X 601 is an oxygen atom, a sulfur atom, or NR 609 .
  • R 611 to R 614 and R 621 to R 624 and R 609 which are not monovalent groups represented by are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom,
  • R 901 to R 907 are as defined in formula (11) above.
  • Ar 601 and Ar 602 are each independently, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 601 to L 603 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding 2 to 4 of these.
  • a 701 ring and A 702 ring are each independently, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • One or more selected from the group consisting of the A 701 ring and the A 702 ring binds to the bond * of the structure represented by the following formula (72).
  • a 703 rings are each independently: A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • X 701 is NR 703 , C(R 704 )(R 705 ), Si(R 706 )(R 707 ), Ge(R 708 )(R 709 ), O, S or Se.
  • R 701 and R 702 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.
  • R 701 and R 702 that do not form a substituted or unsubstituted saturated or unsaturated ring, and R 703 to R 709 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or
  • R 901 to R 907 are as defined in formula (11) above. )
  • a 801 ring is a ring represented by formula (82) that is fused at any position of adjacent rings.
  • the A 802 ring is a ring represented by formula (83) that is fused at any position of adjacent rings.
  • the two bonds * bond to arbitrary positions of the A 803 ring.
  • X 801 and X 802 are each independently C(R 803 )(R 804 ), Si(R 805 )(R 806 ), an oxygen atom, or a sulfur atom.
  • the A 803 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • Ar 801 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 801 to R 806 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are as defined in formula (11) above.
  • m801 and m802 are each independently an integer of 0 to 2. When these are 2, the plurality of R 801 or R 802 may be the same or different.
  • a801 is an integer from 0 to 2. When a801 is 0 or 1, the structures in parentheses indicated by "3-a801" may be the same or different. When a801 is 2, Ar 801 may be the same or different. )
  • L A101 , L B101 , L C101 , L A102 , L B102 , L C102 , and L D102 are each independently, single bond, A substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • n102 is 1, 2, 3, or 4.
  • L E102 is A substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • the plurality of L E102 may be the same or different.
  • the plurality of L E102 is bond to each other to form a substituted or unsubstituted monocycle, or They may be bonded to each other to form a substituted or unsubstituted fused ring, or they may not be bonded to each other.
  • L E102 that does not form the monocyclic ring and does not form the fused ring, A substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • a 101 , B 101 , C 101 , A 102 , B 102 , C 102 , and D 102 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or -Si(R' 901 )(R' 902 )(R' 903 ).
  • R' 901 , R' 902 and R' 903 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. When a plurality of R' 901s exist, the plurality of R' 901s may be the same or different.
  • R 201 to R 208 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by -O-(R 904 ), A
  • L 201 and L 202 are each independently, single bond, A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • Ar 201 and Ar 202 are each independently, A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 , R 801 and R 802 are the same as R 901 to R 907 in formula (11) above.
  • R 2001 to R 2008 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -N(R 906 )(R 907 ), It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted siloxane group.
  • R 901 to R 904 and R 906 to R 907 are as defined in the above formula (11).
  • L 2001 and L 2002 are each independently, It is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
  • Ar 2001 and Ar 2002 are each independently: It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 2101 to R 2108 is a group represented by the following formula (212).
  • R 2101 to R 2108 which are not groups represented by the above formula (212) are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -O-(R 904 ), A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms other than dibenzofuranyl and dibenzothiophenyl groups.
  • R 904 is as defined in formula (11) above.
  • L 2111 is Single bond substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms other than dibenzofuranylene group and dibenzothiophenylene group It is.
  • X 2111 is an oxygen atom or a sulfur atom.
  • One or more sets of two or more adjacent ones of R 2111 to R 2118 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. does not form a ring.
  • One of R 2111 to R 2118 is a single bond bonded to L 2111 .
  • R 2111 to R 2118 that do not form a substituted or unsubstituted saturated or unsaturated ring and are not a single bond bonded to L 2111 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -O-(R 904 ), substituted or unsubstituted phenyl group, A substituted or unsubstituted naphthyl group, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 904 is as defined in formula (11) above.
  • the plurality of groups represented by the formula (212) may be the same or different. ]
  • L 2201 is single bond, A substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 24 ring atoms.
  • R 2201 to R 2210 and one of R 2211 to R 2220 are each a single bond bonded to L 2111 .
  • R 2201 to R 2220 which are not single bonds bonded to L 2111 , are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 carbon
  • R 901 to R 907 are as defined in formula (11) above.
  • R 911 and R 912 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • n2201 is 1, 2, 3, 4, or 5.
  • the two or more L 2201 may be the same or different.
  • R 2301 to R 2310 is a group represented by the following formula (232).
  • R 2301 to R 2310 which are not groups represented by the above formula (232) are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring carbon
  • R 901 to R 907 are as defined in formula (11) above.
  • R 911 and R 912 are as defined in the above formula (221).
  • L 2311 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, other than a substituted or unsubstituted pyrenylene group.
  • Ar 2311 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms other than a substituted or unsubstituted pyrenyl group.
  • n2311 is 1, 2, 3, 4, or 5. When two or more L 2311s exist, the two or more L 2311s may be the same or different.
  • the plurality of groups represented by the formula (232) may be the same or different. )]
  • R 901 to R 905 and R 801 to R 802 are the same as R 901 to R 907 in formula (11) above.
  • at least one of R 101 to R 112 is a group represented by the general formula (11X), and when a plurality of groups represented by the general formula (11X) exist, a plurality of groups represented by the general formula (11X) are present.
  • the groups represented by 11X) are the same or different from each other.
  • L 101 is single bond, A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • Ar 101 is A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • mx is 1, 2, 3, 4, or 5, and when two or more L 101 exist, two or more L 101 are the same or different. When there are two or more Ar 101 , the two or more Ar 101 are the same or different. * indicates the bonding position to the benz[a]anthracene ring in formula (1X). )
  • the first ring structure represented by formula (301) is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted ring in the molecule of the compound ⁇ . It is fused with one or more ring structures selected from the group consisting of heterocycles having 5 to 50 atoms.
  • X 10 is the following formula (301a), (301b), (301c), (301d), (301e), (301f), (301g), (301h), (301i), (301j), (301k), Or it is a divalent group represented by (301m).
  • R 11 to R 14 and R 111 to R 120 are each independently a hydrogen atom or a substituent R.
  • the substituent R is Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are as defined in formula (11) above.
  • the two or more substituents R may be the same or different.
  • the two or more X 10s may be the same or different.
  • X 1 to X 5 are each independently a carbon atom bonded to N, CR 15 , or another atom in the molecule of the compound ⁇ .
  • at least one of X 1 to X 5 is a carbon atom bonded to another atom in the molecule of the compound ⁇ .
  • each of the two or more of X 1 to X 5 may be the same or different.
  • R15 is hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, carboxy group, substituted or unsubstituted ester group, It is a substituted or unsubstituted carbamoyl group, or a substituted
  • the compound ⁇ has a third ring selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring atoms and a substituted or unsubstituted heterocycle having 5 to 50 ring atoms. It is formed by condensing two or three structures represented by the following formula (303) to a ring structure.
  • a is a ring structure condensed to the third ring structure, and is represented by the formula (301).
  • X 11 and X 12 are each independently C(R 16 ) or N.
  • R 16 , R 17 , and R 18 are each independently a hydrogen atom or a substituent R.
  • the substituent R is as defined in the above formula (301). When two or more R 16s exist, the two or more R 16s may be the same or different.
  • the compound ⁇ is represented by the following formula (304) or formula (305).
  • Ar1 is A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • a1, a2, and a3 are each independently a ring structure represented by the above formula (301).
  • X 13 to X 18 are each independently C(R 16 ) or N.
  • R 141 to R 146 and R 16 are a hydrogen atom or a substituent R.
  • the substituent R is as defined in the above formula (301). When two or more R 16s exist, the two or more R 16s may be the same or different.
  • the compound ⁇ is represented by the following formula (304A) or formula (305A).
  • a1, a2, and a3 are each independently a ring structure represented by the above formula (301).
  • X 13 to X 18 are each independently C(R 16 ) or N.
  • R 141 to R 146 and R 16 are a hydrogen atom or a substituent R.
  • the substituent R is as defined in the above formula (301). When two or more R 16s exist, the two or more R 16s may be the same or different.
  • Z 11 and Z 12 are each independently CH or N.
  • the second ring structure represented by the formula (302) is represented by the following formula (321) or formula (322).
  • X 1 and X 4 are each independently N or C(R 121 ).
  • R 121 and R 122 to R 125 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
  • R 901 to R 907 are as defined in formula (11) above.
  • the two or more R 121s may be the same or different.
  • Each * independently indicates a bonding position with another atom in the molecule of the compound ⁇ . ]
  • the compound ⁇ is represented by the following formula (321A).
  • Ar2 is A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • X 1 and X 4 are each independently N or C(R 121 ).
  • R 121 is hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, carboxy group, substituted or unsubstituted ester group, It is a substituted or unsubstituted carbamoyl group, or a substitute
  • the compound ⁇ is represented by the following formula (321B).
  • X 1 and X 4 are each independently N or C(R 121 ).
  • R 121 is hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atom
  • the second ring structure represented by the formula (302) is represented by the following formula (322B).
  • R 122 to R 125 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, carboxy group
  • the compound ⁇ is represented by the following formula (322C).
  • R 122 to R 125 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, carboxy group, substituted or unsubsti
  • the compound ⁇ is represented by the following formula (322D).
  • R 122 to R 125 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, carboxy group, substituted or unsubsti
  • R 901 to R 907 are as defined in formula (11) above.
  • Each of the plurality of R 122 to R 125 may be the same or different.
  • Alp1 is a substituted or unsubstituted aliphatic ring having 3 to 6 ring carbon atoms.
  • the compound ⁇ is represented by the following formula (322E).
  • nx is 1, 2, 3 or 4.
  • R 1225 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 1226 is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 1221 to R 1224 are each independently, hydrogen atom, halogen atom, cyano group, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. )]
  • n is an integer of 1 or more
  • t is an integer of 1 or more
  • u is an integer of 0 or more.
  • LA is A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring atoms, or a substituted or unsubstituted aromatic heterocycle having 6 to 30 ring atoms.
  • CN is a cyano group.
  • D 1 and D 2 are each independently a group represented by the following formula (401Y). In formula (401Y), A nitrogen atom bonds with LA in the formula (401A).
  • F and G each independently represent a ring structure.
  • Ring structure F and ring structure G may be unsubstituted or have a substituent, m is 0 or 1, and when m is 1, Y 20 is a single bond, an oxygen atom, a sulfur represents an atom, a selenium atom, a carbonyl group, CR 21 R 22 , SiR 23 R 24 , or GeR 25 R 26 , and R 21 to R 26 are a substituent R. Further, when m is 1, formula (401Y) is expressed by any of formulas (422) to (428) and formulas (421Y) to (424Y) described below. D 1 and D 2 may be the same or different. When t is 2 or more, the plurality of D 1 's may be the same or different.
  • the plurality of D 2 's may be the same or different.
  • the substituent R is as defined in the above formula (301).
  • R 21 to R 26 are hydrogen atoms or substituents R.
  • the substituent R is as defined in the above formula (301).
  • L A is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 14 ring carbon atoms.
  • the aromatic hydrocarbon ring having 6 to 14 carbon atoms include benzene, naphthalene, fluorene, and phenanthrene.
  • L A is more preferably an aromatic hydrocarbon ring having 6 to 10 ring carbon atoms.
  • the aromatic heterocycle having 6 to 30 ring atoms in L A include pyridine, pyrimidine, pyrazine, quinoline, quinazoline, phenanthroline, benzofuran, and dibenzofuran.
  • formula (401Y) is represented by formula (420Y) below.
  • formula (420Y) A nitrogen atom bonds with LA in the formula (401A).
  • Ring structure F and ring structure G have the same meanings as ring structure F and ring structure G in the formula (401Y).
  • the ring structure F and the ring structure G are preferably 5-membered rings or 6-membered rings, and the 5-membered ring or 6-membered ring is preferably an unsaturated ring, and the 5-membered ring or the 6-membered ring is preferably an unsaturated ring.
  • a membered ring is more preferable.
  • the formula (401Y) is preferably represented by at least one of the following formula (401a) and the following formula (401x).
  • the benzene ring in formulas (401a) and (401x) may be substituted with a substituent R.
  • the substituent R is as defined in the above formula (301).
  • a and B are each independently, It is a ring structure represented by the following formula (401c) or a ring structure represented by the following formula (401d). Ring structure A and ring structure B are condensed with adjacent ring structures at arbitrary positions.
  • px and py are each independently an integer of 0 or more and 4 or less, and represent the number of ring structures A and B, respectively.
  • the plurality of ring structures A may be the same or different.
  • the plurality of ring structures B may be the same or different. Therefore, for example, when px is 2, the ring structure A may have two ring structures represented by the following formula (401c), or may have two ring structures represented by the following formula (401d). , a combination of one ring structure represented by the following formula (401c) and one ring structure represented by the following formula (401d) may be used.
  • the carbon atom in formulas (401c) and (401d) may be substituted with a substituent R.
  • the substituent R is as defined in the above formula (301).
  • Z 7 represents a carbon atom, a nitrogen atom, a sulfur atom, or an oxygen atom.
  • formula (401x) when px is 0 and py is c, it is expressed by formula (401b) below.
  • formula (401b) A nitrogen atom bonds with LA in the above formula (401A).
  • the benzene ring may be substituted with a substituent R.
  • the substituent R is as defined in the above formula (301).
  • c is an integer of 1 or more and 4 or less.
  • the plurality of ring structures E may be the same or different.
  • E represents a ring structure represented by the above formula (401c) or a ring structure represented by the above formula (401d), and the ring structure E is condensed with an adjacent ring structure at any position.
  • the two ring structures E may have two ring structures represented by the formula (401c) or two ring structures represented by the formula (401d). Alternatively, it may be a combination of one ring structure represented by the formula (401c) and one ring structure represented by the formula (401d).
  • Az is substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrimidine ring, It is a ring structure selected from the group consisting of a substituted or unsubstituted triazine ring and a substituted or unsubstituted pyrazine ring.
  • c is 0, 1, 2, 3, 4 or 5.
  • Cz and Az are combined with a single bond.
  • L 23 is A linking group selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.
  • Cz is a group represented by the following formula (501a).
  • Y 21 to Y 28 are each independently N or C(R A3 ).
  • R A3s When a plurality of R A3s exist, one or more of a set of two or more adjacent R A3s are combined with each other to form a ring, or do not form a ring.
  • the R A3s that do not form a ring are each independently: a hydrogen atom substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted phosphoryl group, substituted silyl group, cyano group, It is a group selected from the group consisting of a nitro group and a carboxy group.
  • a plurality of R A3 's may be the same or different. *1 represents a bonding site with a carbon
  • Cz is represented by the above formula (401a) or the above formula (401x).
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted phosphoryl group, substituted silyl group, cyano group, nitro group, It is a group selected from the group consisting of a carboxy group and groups represented by the following formulas (511a) to (511j).
  • Ar EWG is A substituted or unsubstituted heteroaryl group with 5 to 30 ring atoms containing one or more nitrogen atoms in the ring, or an aryl group with 6 to 30 ring carbon atoms substituted with one or more cyano groups. be.
  • Ar X is each independently, hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted phosphoryl group, substituted silyl group, cyano group, nitro group, It is a group selected from the group consisting of a carboxy group and groups represented by the following formulas (511a) to (511j). n is 0, 1, 2, 3, 4 or 5. When n is 2, 3, 4 or 5, the plurality of Ar X
  • ring (A) is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocycle, and is a 5-membered ring, a 6-membered ring, or a 7-membered ring.
  • Ring (A) may be an aromatic hydrocarbon ring or a heterocycle.
  • Ar 1 and Ar X each bond to an element constituting the ring (A).
  • At least one of Ar 1 and Ar X is a group selected from the group consisting of groups represented by the following formulas (511a) to (511j).
  • X 1 to X 20 are each independently N or C(R A1 ).
  • any one of X 5 to X 8 is a carbon atom bonded to any one of X 9 to X 12
  • any one of X 9 to X 12 is bonded to any one of X 5 to X 8 .
  • any one of X 5 to X 8 is a carbon atom bonded to the nitrogen atom in the ring containing A 2 .
  • any one of X 5 to X 8 and X 18 is a carbon atom bonded to any one of X 9 to X 12 , and any one of X 9 to It is a carbon atom bonded to any one of X18 .
  • any one of X 5 to X 8 and X 18 is a carbon atom bonded to any one of X 9 to X 12 and X 19 , and any one of X 9 to X 12 and X 19 is, It is a carbon atom bonded to any one of X 5 to X 8 and X 18 .
  • any one of X 5 to X 8 is a carbon atom bonded to any one of X 9 to X 12 and X 19
  • any one of X 9 to X 12 and X 19 is It is a carbon atom that bonds with any of X8 .
  • any one of X 5 to X 8 and X 18 is a carbon atom bonded to the nitrogen atom in the ring containing A 2 .
  • any of X 5 to X 8 and X 18 is a bond to the nitrogen atom connecting the ring containing X 9 to X 12 and X 19 to the ring containing X 13 to X 16 and is a carbon atom.
  • any of X 5 to X 8 is a carbon atom bonded to the nitrogen atom connecting the ring containing X 9 to X 12 and X 19 to the ring containing X 13 to X 16 and X 20 . It is.
  • R A1s When a plurality of R A1s exist, one or more of a set of two or more adjacent R A1s are bonded directly to each other to form a ring or via a hetero atom.
  • the R A1 that does not form a ring is each independently: a hydrogen atom substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted phosphoryl group, substituted silyl group, cyano group, It is a group selected from the group consisting of a nitro group and a carboxy group.
  • a plurality of R A1s may be the same or different. .
  • the plurality of R A1s preferably do not form the ring.
  • * represents a bonding site with ring (A).
  • R 2021 to R 2025 are each independently, hydrogen atom, Substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted phosphoryl group, substituted silyl group, cyano group, It is a group selected from the group consisting of a nitro group and a carboxy group.
  • Ara is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, It is a group selected from the group consisting of a substituted phosphoryl group and a substituted silyl group.
  • Ara A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5
  • A3 is A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L3 is single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, Substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms are bonded together.
  • R 31 to R 38 are bond to each other to form a substituted or unsubstituted monocycle, They may be bonded to each other to form a substituted or unsubstituted fused ring, or they may not be bonded to each other.
  • R 31 to R 38 which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted fused ring are each independently: hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by -O-(R 904 ), A group represented by -S-(R 905 ), A group represented by -N(R 906 )
  • L 31 is single bond, A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the heterocyclic group, or Two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms are bonded together.
  • L 32 is single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • n 3 is 1, 2, 3, 4 or 5.
  • L 31 is a single bond
  • n 3 is 1, and L 32 is bonded to the carbon atom of the 6-membered ring in the general formula (601).
  • the plurality of L 32s may be the same or different.
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • the plurality of R 901s may be the same or different.
  • the plurality of R 902s may be the same or different.
  • the plurality of R 903s may be the same or different.
  • the plurality of R 904s may be the same or different.
  • the plurality of R 905s may be the same or different.
  • the plurality of R 906s may be the same or different.
  • the plurality of R 907s may be the same or different.
  • the plurality of R 908s may be the same or different.
  • the plurality of R 909s may be the same or different.
  • the plurality of R 931s may be the same or different.
  • the plurality of R 932s may be the same or different.
  • the plurality of R 933s may be the same or different.
  • the plurality of R 934s may be the same or different.
  • the plurality of R 935s may be the same or different.
  • the plurality of R 936s may be the same or different.
  • the plurality of R 937s may be the same or different.
  • Y 31 to Y 36 are each independently CR 3 or a nitrogen atom. However, one or more of Y 31 to Y 36 is a nitrogen atom.
  • R 3s When a plurality of R 3s exist, one or more of the sets consisting of two or more adjacent ones of the plurality of R 3s are bond to each other to form a substituted or unsubstituted monocycle, They may be bonded to each other to form a substituted or unsubstituted fused ring, or they may not be bonded to each other.
  • Each R 3 that does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring is independently: hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by -O-(R 904 ), A group represented by -S-(R 905 ), A group represented by -N(R 906 )(R 907
  • R 901 to R 907 are as defined in formula (11) above.
  • R 908 , R 909 , and R 931 to R 937 are as defined in the above formula (601).
  • RB is Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by -O-(R 904 ), A group represented by -S-(R 905 ), A group represented by -N(R 906 )(
  • R 901 to R 907 are as defined in formula (11) above.
  • R 908 , R 909 , and R 931 to R 937 are as defined in the above formula (601).
  • L 31 is single bond, A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the heterocyclic group, or Two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms are bonded together.
  • L 32 is single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • n3 is 1, 2, 3, 4 or 5.
  • L 31 is a single bond
  • n 3 is 1, and L 32 is bonded to the carbon atom of the 6-membered ring in the general formula (611).
  • * is a bonding site with the carbon atom of the 6-membered ring in the general formula (611).
  • b is an integer from 1 to 3. Any one of R 201 , R 202 , R 206 to R 209 is a single bond bonded to L 2 . One or more pairs of adjacent two or more of R 201 , R 202 , and R 206 to R 209 that are not single bonds bonded to L 2 are bonded to each other and are substituted or unsubstituted, saturated or unsaturated. or does not form a substituted or unsubstituted saturated or unsaturated ring.
  • R 201 , R 202 , and R 206 to R 209 that are not a single bond bonded to L 2 and do not form a substituted or unsubstituted saturated or unsaturated ring each independently represent a hydrogen atom or a substituent R It is.
  • L 2 is single bond, Substituted or unsubstituted linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, Substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 40 ring carbon atoms, Substituted or unsubstituted divalent heterocyclic group having 5 to 40 ring atoms, A divalent multiple linking group formed by bonding two to three groups selected from the aromatic hydrocarbon ring groups, A divalent multiple linking group formed by bonding 2 to 3 groups selected from the above heterocyclic groups, or 2 to 3 groups selected from the above aromatic hydrocarbon cyclic groups and the above heterocyclic groups.
  • L 2 is Substituted or unsubstituted linear, branched or cyclic aliphatic hydrocarbon group having 1 to 30 carbon atoms, Substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms; a multiple linking group formed by bonding two to three groups selected from the aromatic hydrocarbon ring groups, A multiple linking group formed by bonding two to three groups selected from the above heterocyclic groups, or a multi-linking group formed by bonding two to three groups selected from the aromatic hydrocarbon ring group and the above heterocyclic group.
  • the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group may be the same or different. At least one set of two or more adjacent ones of the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. or do not form substituted or unsubstituted saturated or unsaturated rings.
  • Ar 2 is A substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
  • Ar 2 and L 2 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.
  • the substituent R is as defined in the above formula (301).
  • X 1 is a nitrogen atom or CR 1 .
  • X2 is a nitrogen atom or CR2 .
  • X3 is a nitrogen atom or CR3 .
  • X 4 is a nitrogen atom or CR 4 .
  • X5 is a nitrogen atom or CR5 .
  • X6 is a nitrogen atom or CR6 .
  • at least one of X 1 to X 6 is a nitrogen atom.
  • 1 to 3 of R 1 to R 6 are each independently a group represented by any of the following formulas (712) to (715).
  • R 1 to R 6 that are not groups represented by any of the following formulas (712) to (715) are each independently a hydrogen atom or a substituent R.
  • R 1 to R 6 One or more pairs of adjacent two or more of R 1 to R 6 are bonded to each other, Substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 30 ring carbon atoms, substituted or unsubstituted non-fused aromatic hydrocarbon ring, A substituted or unsubstituted fused aromatic heterocycle having 9 to 30 ring atoms, or A substituted or unsubstituted non-fused aromatic heterocycle having 5 or 6 ring atoms is formed, or the ring is not formed.
  • the substituent R is as defined in the above formula (301).
  • L 1 , L 3 , L 6 , L 8 and L 9 are each independently, Substituted or unsubstituted fused aryl group having 10 to 30 ring carbon atoms, a substituted or unsubstituted non-fused aryl group having 6 to 30 ring carbon atoms; A substituted or unsubstituted fused heteroaryl group having 9 to 32 ring atoms, or a substituted or unsubstituted non-fused heteroaryl group having 5 to 30 ring atoms.
  • L 2 , L 4 , and L 5 are each independently, a substituted or unsubstituted fused arylene group having 10 to 30 ring carbon atoms; a substituted or unsubstituted non-fused arylene group having 6 to 30 ring carbon atoms; A substituted or unsubstituted fused heteroarylene group having 9 to 30 ring atoms, or a substituted or unsubstituted non-fused heteroarylene group having 5 to 30 ring atoms.
  • L7 is Substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 30 ring carbon atoms, Substituted or unsubstituted non-fused aromatic hydrocarbon ring having 10 to 30 ring carbon atoms, A substituted or unsubstituted fused aromatic heterocyclic group having 9 to 30 ring atoms, or a substituted or unsubstituted trivalent non-fused aromatic heterocyclic group having 5 or 6 ring atoms.
  • A is Substituted or unsubstituted fused aryl group having 10 to 30 ring carbon atoms, a substituted or unsubstituted non-fused aryl group having 6 to 30 ring carbon atoms; A substituted or unsubstituted fused heteroaryl group having 9 to 30 ring atoms, or a substituted or unsubstituted non-fused heteroaryl group having 5 to 30 ring atoms.
  • L is a substituted or unsubstituted fused arylene group having 10 to 30 ring carbon atoms; a substituted or unsubstituted non-fused arylene group having 6 to 30 ring carbon atoms; A substituted or unsubstituted fused heteroarylene group having 9 to 30 ring atoms, or a substituted or unsubstituted non-fused heteroarylene group having 5 to 30 ring atoms.
  • n is an integer from 0 to 2. When n is 0, L is a single bond. When n is 2, the two L's may be the same or different.
  • Ar is a substituted or unsubstituted fused arylene group having 10 to 30 ring carbon atoms; a substituted or unsubstituted non-fused arylene group having 6 to 30 ring carbon atoms; A substituted or unsubstituted fused heteroarylene group having 9 to 30 ring atoms, or a substituted or unsubstituted non-fused heteroarylene group having 5 to 30 ring atoms.
  • first organic compound and the second organic compound one or more compounds selected from the compounds included in the following (Group 9A) can also be used independently.
  • first organic compound and the second organic compound in the present specification are not limited to one or more compounds selected from the compounds included in the following (Group 9A), but are You don't have to.
  • the first organic compound and the second organic compound each independently use one or more compounds selected from the compounds included in each of the following groups (Group 1B) to (Group 35B). You can also. Note that the first organic compound and the second organic compound in the present specification are each independently limited to one or more compounds selected from the compounds included in each of the following groups (Group 1B) to (Group 35B). It does not have to be these.
  • ADN 9,10-di(2-naphthyl)anthracene
  • TAADN 2-tert-butyl-9,10-di(2-naphthyl)anthracene
  • rublen 5,6,11,12-tetraphenyltetracene
  • TBP 2,5,8,11-tetra-tert-butylperylene
  • N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine NPD
  • Alq3 10-(2-benzothiazolyl)-1, 1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolidin-11-one (C545T); , 6,11,12-tetraphenyltetracene); 4,4'-bis(2,2-diphenylvinyl)biphenyl (DPVBi)
  • Tetracene Tetrafluoro-tetracyano-quinodimethane (F4-TCNQ); 4,4',4''-tris[phenyl(m-tolyl)amino]triphenylamine; Naphthalenetetracarboxylic anhydride (NTCDA); Leuco Crystal Violet (LCV); N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine (TPD)
  • the first premix material may or may not contain components other than the first component and the second component.
  • the first premix material consists only of the first component and the second component, or consists essentially of the first component and the second component. In the latter case, it may contain unavoidable impurities. In one embodiment, the first premix material is 80% by weight or more, 85% by weight or more, 90% by weight or more, 95% by weight or more, 99% by weight or more, 99.5% by weight or more, 99.9% by weight or more. , 99.99% by mass or more or 100% by mass are the first component and the second component.
  • the first premix material is 80 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, 99.5 mol% or more, 99.9 mol% or more, 99.99 mol% % or more or 100 mol % are the first component and the second component.
  • the first premix material consists only of the first component, the second component and the third component, or consists essentially of the first component, the second component and the third component. In the latter case, it may contain unavoidable impurities.
  • the third component is an arbitrary organic compound (third organic compound).
  • the first premix material is 80% by weight or more, 85% by weight or more, 90% by weight or more, 95% by weight or more, 99% by weight or more, 99.5% by weight or more, 99.9% by weight or more. , 99.99% by mass or more are the first component and the second component, and the remainder is the third component.
  • the third component is an arbitrary organic compound (third organic compound).
  • the first premix material is 80 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, 99.5 mol% or more, 99.9 mol% or more, 99.99 mol% % or more are the first component and the second component, and the remainder is the third component.
  • the third component is an arbitrary organic compound (third organic compound).
  • the first premix material can be expressed as follows (hereinafter also referred to as "first premix material (3)").
  • the first premix material (3) is the same as the first premix material described above, except that it does not have the specific item "for vacuum deposition".
  • the method for producing a mixed powder according to one aspect of the present invention can be expressed as follows (hereinafter also referred to as "the first method for producing a premix material").
  • Mixing comprising pulverizing and mixing a mixture of a first material containing a first organic compound and a second material containing a second organic compound so that the volume median diameter is 10 ⁇ m or more and 60 ⁇ m or less.
  • Powder manufacturing method This manufacturing method assumes the manufacturing method of the first premix material described above. The manufacturing method will be explained below.
  • first material and the second material are weighed, placed in a mortar, etc., and mixed.
  • the first material and the second material are usually in powder form.
  • the obtained mixture is put into a pulverizer (pulverizing mill) and pulverized.
  • pulverizer pulverizing mill
  • the crusher There are no particular restrictions on the crusher, and any commercially available crusher can be used.
  • the crushing conditions as long as the volume median diameter is 10 ⁇ m or more and 60 ⁇ m or less, but for example, the rotation speed of the crushing blade is 20,000 to 30,000 rpm, and the process of repeating rotation and stopping is about 5 to 10 minutes in total. There are several ways to do this.
  • the method of manufacturing the first premix material is typically selected from the group consisting of adhering the first material and the second material, covering one with the other, and embedding one in the other. Does not include one or more steps. Specifically, the process involves melting and mixing a first material and a second material, and a mechanofusion process (compounding by applying strong mechanical energy to multiple different particles to cause a mechanochemical reaction). method of manufacturing particles).
  • the mixed powder obtained by the first premix material manufacturing method usually consists of only the first powder and the second powder, or consists essentially of the first powder and the second powder. It consists only of the body.
  • the method for manufacturing a mixed powder according to one embodiment of the present invention can be expressed as follows (hereinafter also referred to as "first premix material manufacturing method (2)"). It includes mixing a first organic compound powder having a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less and a second organic compound powder having a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less. , a method for producing mixed powder.
  • the first premix material manufacturing method (2) is a method in which the volume median diameter of each of the first material and the second material is adjusted to a predetermined value or less, and then these are mixed. Other than this point, the method for manufacturing the first premix material is the same. As a method for adjusting the volume median diameter of the first material and the second material, the pulverization method described in the first premix material manufacturing method can be adopted. After mixing the first material and the second material, pulverization may be performed again.
  • the mixed powder obtained in the first premix material manufacturing method (2) usually consists of only the first powder and the second powder, or it consists essentially of the first powder. and the second powder only.
  • the mixed powder according to one aspect of the present invention can be expressed as follows (hereinafter also referred to as "second premix material").
  • a mixed powder that can be used in a vapor deposition method includes a first powder consisting only of a first organic compound and a second powder consisting only of a second organic compound, wherein the first powder
  • the mixed powder has a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less, and the volume median diameter of the second powder is 10 ⁇ m or more and 60 ⁇ m or less.
  • the second premix material stipulates that it "contains a first powder consisting only of a first organic compound and a second powder consisting only of a second organic compound," and a mixed powder. It is the same as the first premix material described above, except that it includes specific details of the volume median diameter of each of the first component and the second component instead of the volume median diameter of the material. In the second premix material, since the volume median diameters of the first powder and the second powder are set to be close to each other, the effect of improving the stability of the continuous vapor deposition process described above can be more expected. Regarding the volume median diameter of each of the first component and the second component, the matters explained for the first premix material (2) can be applied.
  • the volume median diameter of the second premix material is 10 ⁇ m or more and 60 ⁇ m or less, and the volume median diameter of the entire mixed powder is as described in the first premix material. Can apply matters.
  • the second premix material is the same as the first premix material according to one aspect of the present invention described above except for the above points. That is, the mixing ratio of the first organic compound and the second organic compound, the possibility of use in the vacuum evaporation method, the compound types of the first organic compound and the second organic compound, other components, etc. are the same as the first premix material. As explained in.
  • the mixed powder according to one aspect of the present invention can be expressed as follows (hereinafter also referred to as "second premix material (2)").
  • a mixed powder including a first powder consisting only of a first organic compound and a second powder consisting only of a second organic compound, wherein the volume median diameter of the first powder is The mixed powder is 10 ⁇ m or more and 60 ⁇ m or less, and the volume median diameter of the second powder is 10 ⁇ m or more and 60 ⁇ m or less.
  • the second premix material (2) is the same as the second premix material described above, except that it does not have the specific item "for vacuum deposition".
  • the mixed powder according to one aspect of the present invention can be expressed as follows (hereinafter also referred to as "third premix material").
  • a mixed powder for vacuum evaporation containing a first organic compound and a second organic compound, the mixed powder having a standard deviation of particle size distribution of 100 ⁇ m or less.
  • the third premix material is the same as the first premix material described above, except that it includes a specification of the standard deviation of the particle size distribution instead of the volume median diameter of the mixed powder. Since the third premix material is a powder with small variations in particle size and high homogeneity in particle size, it can be expected to have the effect of making the vapor deposition characteristics and thermal behavior more homogeneous when subjected to the vapor deposition process.
  • the standard deviation of the particle size distribution is as explained for the first premix material. In one embodiment, the standard deviation of the particle size distribution in the third premix material may be 70 ⁇ m or less, 50 ⁇ m or less, or 30 ⁇ m or less.
  • the volume median diameter of the third premix material is 10 ⁇ m or more and 60 ⁇ m or less. Regarding the volume median diameter, the matters explained for the first premix material can be applied.
  • the third premix material includes a first powder and a second powder (hereinafter, this aspect is also referred to as "third premix material (2)").
  • the standard deviation of the particle size distribution of the first powder in the third premix material (2) is 100 ⁇ m or less, and the standard deviation of the particle size distribution of the second powder is 100 ⁇ m or less.
  • the standard deviation of the particle size distribution of the first powder in the third premix material (2) is 50 ⁇ m or less, and the standard deviation of the particle size distribution of the second powder is 50 ⁇ m or less.
  • the first powder in the third premix material (2), has a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less, and the second powder has a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less. It is. In one embodiment, in the third premix material (2), the first powder has a volume median diameter of 20 ⁇ m or more and 50 ⁇ m or less, and the second powder has a volume median diameter of 20 ⁇ m or more and 50 ⁇ m or less. It is.
  • the third premix material is the same as the first premix material according to one aspect of the present invention described above except for the above points. That is, the mixing ratio of the first organic compound and the second organic compound, the possibility of use in the vacuum evaporation method, the compound types of the first organic compound and the second organic compound, other components, etc. are the same as the first premix material. As explained in.
  • the method for manufacturing the third premix material can be expressed as follows.
  • a mixed powder comprising pulverizing and mixing a mixture of a first material containing a first organic compound and a second material containing a second organic compound so that the standard deviation of particle size distribution is 100 ⁇ m or less. How the body is manufactured.
  • the manufacturing method is the same as above except that the specific item "so that the volume median diameter is 10 ⁇ m or more and 60 ⁇ m or less" is replaced with the specific item "so that the standard deviation of the particle size distribution is 100 ⁇ m or less".
  • the method is the same as the manufacturing method of the first premix material.
  • the particle size may be adjusted so that the volume median diameter is 10 ⁇ m or more and 60 ⁇ m or less, and the manufacturing conditions for the first premix material can be adopted as appropriate.
  • a vapor deposition method includes heating and vaporizing the premix materials (first to third premix materials) according to one aspect of the present invention from a single vapor deposition source, and It includes the step of forming a film on the vapor deposition surface of the base material.
  • Other conditions for the vapor deposition method are not particularly limited, and general vapor deposition equipment and vapor deposition conditions can be used.
  • Vapor deposition is usually performed under vacuum (at a pressure lower than atmospheric pressure).
  • the pressure inside the apparatus during vapor deposition is preferably 5.0 Pa or less, more preferably 1.0 Pa or less.
  • the heating temperature during vapor deposition is usually 150°C to 400°C, preferably 200 to 350°C.
  • the powder made of the mixed powder may be compressed in advance into pellets, and the pellets may be put into a vapor deposition source to perform vapor deposition.
  • a method for manufacturing an organic EL element according to one embodiment of the present invention includes vacuum-depositing the mixed powder (first to third premix materials) according to one embodiment of the present invention described above.
  • a method for manufacturing an organic EL element using the above-described first premix material can be expressed as follows.
  • a method for producing an organic electroluminescent device comprising: a cathode, an anode, and one or more organic layers including a light emitting layer disposed between the cathode and the anode,
  • a mixed powder containing a first organic compound and a second organic compound and having a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less is vaporized by heating from a vapor deposition source to form the one or more organic layer. comprising depositing at least one layer of A method for manufacturing an organic electroluminescent device.
  • the mixed powder used in this embodiment is as explained in the first premix material, and the vapor deposition method in this embodiment is as explained in the vapor deposition method in one embodiment of the present invention described above.
  • a second or third premix material instead of the first premix material, "a mixture containing a first organic compound and a second organic compound and having a volume median diameter of 10 ⁇ m or more and 60 ⁇ m or less
  • a manufacturing method using a corresponding mixed powder instead of "powder” may be adopted.
  • the organic EL device according to this embodiment will be described below.
  • An example of the element structure of the organic EL element is a structure in which the following structures (1) to (4) are laminated on a substrate.
  • Anode/Emissive layer/Cathode (2) Anode/Hole transport zone/Emissive layer/Cathode (3) Anode/Emissive layer/Electron transport zone/Cathode (4) Anode/Hole transport zone/Emissive layer/Electron Transport zone/cathode (“/” indicates that each layer is stacked adjacent to each other.)
  • the electron transport zone is a region consisting of one or more organic layers (also referred to as "electron transport layer” and/or “electron injection layer") containing an electron transporting compound
  • the hole transport zone is a region consisting of one or more organic layers containing an electron transport compound (also referred to as "electron transport layer” and/or “electron injection layer") This region is composed of one or more organic layers (also referred to as "hole transport layer” and/or "hole injection layer”)
  • the organic EL element 1 includes a substrate 2, an anode 3, a light emitting layer 5, a cathode 10, a hole transport zone 4 between the anode 3 and the light emitting layer 5, and a hole transport zone 4 between the light emitting layer 5 and the cathode 10. It has an electron transport band 6 located at .
  • At least one of the organic layers of the organic EL element is formed by a vapor deposition method using the above mixed powder.
  • the layer formed from the mixed powder is not particularly limited, and may be any organic layer. Furthermore, two or more of the organic layers may be formed by vapor deposition using the mixed powder.
  • the combination of the first component and the second component in the mixed powder used for forming the organic layer include, but are not limited to, the following combinations.
  • the first component is a host material for the fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is a dopant material (fluorescent compound) for the fluorescent light emitting layer.
  • the first component is a host material for the fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is a host material for the fluorescent light emitting layer (host material for a fluorescent light emitting device).
  • the first component is a host material for a fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is a hole transporting compound.
  • the first component is a host material for a fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is an electron transporting compound.
  • the first component is a host material for a fluorescent light-emitting layer (host material for a fluorescent light-emitting device), and the second component is a hole-injecting compound.
  • the first component is a host material for a fluorescent light emitting layer (host material for a fluorescent light emitting device), and the second component is an electron injection compound.
  • the first component is a host material for the phosphorescent layer (host material for a phosphorescent device), and the second component is a dopant material (phosphorescent compound) for the phosphorescent layer.
  • the first component is a host material for the phosphorescent layer (host material for a phosphorescent device), and the second component is a host material for the phosphorescent layer (host material for a phosphorescent device).
  • the first component is a host material for a phosphorescent layer (host material for a phosphorescent device), and the second component is a hole-transporting compound.
  • the first component is a host material for a phosphorescent layer (host material for a phosphorescent device), and the second component is an electron transporting compound.
  • the first component is a host material for a phosphorescent layer (host material for a phosphorescent device), and the second component is a hole-injecting compound.
  • the first component is a host material for a phosphorescent layer (host material for a phosphorescent device), and the second component is an electron injection compound.
  • the first component is a hole transporting compound and the second component is a dopant material for the emissive layer.
  • the first component is a hole-transporting compound
  • the second component is a host material for a fluorescent layer (host material for a fluorescent device).
  • the first component is a hole-transporting compound
  • the second component is a host material for a phosphorescent layer (host material for a phosphorescent device).
  • the first component is a hole transporting compound and the second component is a hole transporting compound.
  • the first component is a hole transporting compound and the second component is an electron transporting compound.
  • the first component is a hole-transporting compound and the second component is a hole-injecting compound.
  • the first component is a hole-transporting compound and the second component is an electron-injecting compound.
  • the first component is an electron transporting compound and the second component is a dopant material for the emissive layer.
  • the first component is an electron transporting compound
  • the second component is a host material for a fluorescent layer (host material for a fluorescent device).
  • the first component is an electron transporting compound
  • the second component is a host material for a phosphorescent layer (host material for a phosphorescent device).
  • the first component is an electron transporting compound and the second component is a hole transporting compound.
  • the first component is an electron transporting compound and the second component is an electron transporting compound.
  • the first component is an electron-transporting compound and the second component is a hole-injecting compound.
  • the first component is an electron transporting compound and the second component is an electron injecting compound.
  • the first component is a hole-injecting compound and the second component is a dopant material for the emissive layer.
  • the first component is a hole-injecting compound
  • the second component is a host material for a fluorescent layer (host material for a fluorescent device).
  • the first component is a hole-injecting compound
  • the second component is a host material for a phosphorescent layer (host material for a phosphorescent device).
  • the first component is a hole-injecting compound and the second component is a hole-transporting compound.
  • the first component is a hole-injecting compound and the second component is an electron-transporting compound. In one embodiment, the first component is a hole-injecting compound and the second component is a hole-injecting compound. In one embodiment, the first component is a hole-injecting compound and the second component is an electron-injecting compound. In one embodiment, the first component is an electron-injecting compound and the second component is a dopant material for the emissive layer. In one embodiment, the first component is an electron-injecting compound, and the second component is a host material for a fluorescent layer (host material for a fluorescent device).
  • the first component is an electron injection compound
  • the second component is a host material for a phosphorescent layer (host material for a phosphorescent device).
  • the first component is an electron injection compound and the second component is a hole transport compound.
  • the first component is an electron-injecting compound and the second component is an electron-transporting compound.
  • the first component is an electron-injecting compound and the second component is a hole-injecting compound.
  • the first component is an electron-injecting compound and the second component is an electron-injecting compound.
  • the first component and the second component are not organometallic compounds.
  • the mixed powder does not include a phosphorescent compound. In one embodiment, the mixed powder is free of heavy metal complexes.
  • each layer other than the layer formed by vapor deposition of the mixed powder described above is not particularly limited, and a forming method such as a vacuum vapor deposition method using a single material, a spin coating method, etc. can be used.
  • a forming method such as a vacuum vapor deposition method using a single material, a spin coating method, etc. can be used.
  • a spin coating method etc.
  • the substrate is used as a support for the light emitting device.
  • the substrate for example, glass, quartz, plastic, etc. can be used.
  • a flexible substrate may be used.
  • the flexible substrate refers to a bendable (flexible) substrate, and includes, for example, a plastic substrate made of polycarbonate or polyvinyl chloride.
  • anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more).
  • a metal for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene.
  • ITO indium oxide-tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide indium oxide-zinc oxide
  • tungsten oxide indium oxide containing zinc oxide
  • graphene graphene.
  • gold gold
  • platinum platinum
  • nitrides of metal materials eg, titanium nitride
  • the hole injection layer is a layer containing a substance with high hole injection properties.
  • Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, aromatic amine compounds, or high molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used.
  • the hole transport layer is a layer containing a substance with high hole transport properties.
  • aromatic amine compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • materials other than these may be used as long as they have a higher transportability for holes than for electrons.
  • the layer containing a substance with high hole transport properties is not limited to a single layer, and may be a stack of two or more layers made of the above substance.
  • the light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used for the light-emitting layer.
  • a highly luminescent substance a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as a highly luminescent substance.
  • a fluorescent compound is a compound capable of emitting light from a singlet excited state
  • a phosphorescent compound is a compound capable of emitting light from a triplet excited state.
  • blue fluorescent material that can be used in the light emitting layer
  • green fluorescent material that can be used in the light emitting layer
  • aromatic amine derivatives and the like can be used.
  • Tetracene derivatives, diamine derivatives, etc. can be used as red fluorescent materials that can be used in the light emitting layer.
  • Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue-based phosphorescent materials that can be used in the light-emitting layer.
  • An iridium complex or the like is used as a green phosphorescent material that can be used in the light emitting layer.
  • Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red-colored phosphorescent materials that can be used in the light-emitting layer.
  • the light-emitting layer may have a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material).
  • Various substances can be used to disperse highly luminescent substances, and the lowest unoccupied orbital level (LUMO level) is higher than that of highly luminescent substances, and the highest occupied orbital level (LUMO level) is higher than that of highly luminescent substances. It is preferable to use a substance with a low HOMO level.
  • Substances (host materials) for dispersing highly luminescent substances include 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, 2) oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives. Heterocyclic compounds, 3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, 4) aromatic amine compounds such as triarylamine derivatives, or fused polycyclic aromatic amine derivatives. used.
  • the electron transport layer is a layer containing a substance with high electron transport properties.
  • the electron transport layer contains 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. can be used.
  • the electron injection layer is a layer containing a substance with high electron injection properties.
  • the electron injection layer contains lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 8-hydroxyquinolinolato-lithium (Liq), etc.
  • Metal complex compounds, alkali metals such as lithium oxide (LiO x ), alkaline earth metals, or compounds thereof can be used.
  • cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less).
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium ( Alkaline earth metals such as Ca), strontium (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • the cathode is usually formed by vacuum evaporation or sputtering.
  • a coating method, an inkjet method, etc. can be used.
  • the cathode when an electron injection layer is provided, can be formed using various conductive materials such as aluminum, silver, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the size of the work function. can be formed.
  • each of the above layers is not particularly limited, but is generally preferably in the range of several nm to 1 ⁇ m in order to suppress defects such as pinholes, keep the applied voltage low, and improve luminous efficiency.
  • first composition The composition according to one aspect of the present invention is expressed as follows (hereinafter also referred to as "first composition").
  • a composition comprising a first organic compound and a second organic compound, Differential scanning calorific value of a mixed powder containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition and having a volume median diameter of 10 ⁇ m or more and 40 ⁇ m or less.
  • the endothermic peak temperature P1 measured in the measurement and the volume median diameter containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition are more than 60 ⁇ m and 90 ⁇ m.
  • a composition in which the following endothermic peak temperature P2 measured in differential scanning calorimetry of the mixed powder satisfies the following formula (1).
  • the matters explained for the first premix material mentioned above can be applied.
  • the shape of the above composition may or may not be a mixed powder.
  • the mixed powder explained in the mixed powder (premix material) in one embodiment of the present invention described above can be used.
  • the volume median diameter of the composition (mixed powder) is 10 ⁇ m or more and 60 ⁇ m or less.
  • the composition described above satisfies any of the following formulas.
  • the composition described above satisfies any of the following formulas.
  • S1 is a compound containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition, and has a volume median diameter of 10 ⁇ m or more and 40 ⁇ m or less.
  • S2 is the endothermic peak intensity measured in differential scanning calorimetry of a certain mixed powder; This is the endothermic peak intensity measured in differential scanning calorimetry of a mixed powder having a volume median diameter of more than 60 ⁇ m and 90 ⁇ m or less.
  • the composition is a thin film, for example, at least one layer (e.g., a light emitting layer) of the organic layers constituting an organic EL element.
  • a light emitting layer e.g., a light emitting layer
  • the organic EL element the matters explained in the above-mentioned [Method for manufacturing an organic electroluminescent element] can be applied.
  • composition The composition according to one aspect of the present invention is expressed as follows (hereinafter also referred to as "second composition").
  • a composition comprising a first organic compound and a second organic compound, In differential scanning calorimetry of a mixed powder containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition and having a standard deviation of particle size distribution of 50 ⁇ m or less.
  • the measured endothermic peak temperature P11 and the standard deviation of the particle size distribution containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition are more than 100 ⁇ m.
  • a composition in which an endothermic peak temperature P12 measured in differential scanning calorimetry of mixed powder satisfies the following formula (11).
  • the shape of the above composition may or may not be a mixed powder.
  • a mixed powder the mixed powder described in the above-mentioned mixed powder (premix material) in one embodiment of the present invention can be used.
  • the standard deviation of the particle size distribution of the composition (mixed powder) is 100 ⁇ m or less.
  • the second composition satisfies any of the following formulas.
  • the second composition satisfies any of the following formulas.
  • S11 is a mixture containing the solid first organic compound and the solid second organic compound in the same mass ratio as the composition and having a standard deviation of particle size distribution of 50 ⁇ m or less.
  • S12 is the endothermic peak intensity measured in differential scanning calorimetry of powder
  • S12 is the intensity of the endothermic peak measured in differential scanning calorimetry of powder
  • S12 is the intensity of the endothermic peak measured when the solid first organic compound and the solid second organic compound are mixed in the same mass ratio as the composition.
  • This is the endothermic peak intensity measured in differential scanning calorimetry of a mixed powder containing a particle size distribution with a standard deviation of more than 100 ⁇ m.
  • the second composition is the same as the first composition except as described above.
  • BH-1 and BH-2 used in Examples and Comparative Examples are both light-emitting layer host materials (fluorescent) of organic EL devices.
  • ⁇ Method for measuring volume median diameter of powder and standard deviation of particle size distribution The method for measuring the volume median diameter of powder and the standard deviation of particle size distribution in Examples, Comparative Examples, and Experimental Examples is as follows. Add 3.3 ml of ultrapure water to a 10 ml vial. Next, 40 mg of dispersion material (sodium polyphosphate, CAS No. 68915-31-1) is added to the vial, the vial is capped, and the vial is shaken 5 times by hand. Next, open the vial, add the powder to be measured, cover the vial, and shake it by hand five times. The amount of powder to be measured varies depending on the object, so determine the appropriate amount based on the measurement guidelines of the particle size distribution analyzer.
  • dispersion material sodium polyphosphate, CAS No. 68915-31-1
  • the vial is then sonicated at 40 kHz for 1 minute at 40° C. using an ultrasonic cleaner.
  • the vial is then opened and the contents are stirred five times using a stir bar.
  • a sample (the contents of the vial) is poured into the measurement cell up to the measurement range, and it is confirmed that the measurement range is appropriate. If the measurement range is not appropriate, adjust as appropriate to bring it within the appropriate measurement range. That is, if the concentration of the sample is too high, ultrapure water is added, and if the concentration of the sample is too low, the powder to be measured is added.
  • the measurement cell was set in a particle size distribution meter (manufactured by Nikkiso Co., Ltd., Microtrac (registered trademark) MT3000II, measurement principle: laser diffraction/scattering method), left to stand for 60 seconds, and then measured. Determine the particle size and standard deviation of the particle size distribution.
  • a particle size distribution meter manufactured by Nikkiso Co., Ltd., Microtrac (registered trademark) MT3000II, measurement principle: laser diffraction/scattering method
  • Example 1 ⁇ Crushing and mixing> Powder consisting of BH-1 (first component) and powder consisting of BH-2 (second component) were weighed at a ratio of 60.5:39.5 (mass ratio), and a grinding mill (dry grinder, The sample was placed in a tube ("Tube Mill control" manufactured by IKA). Pulverization and mixing were performed using the mill under the following conditions to obtain mixed powder 1.
  • (Crushing mixing method) ⁇ Rotation speed of crushing blade: 25000rpm - One set consisted of repeating the process of rotating the crushing blade for 15 seconds and then stopping for 1 second for 3 minutes, for a total of 3 sets. -The interval between sets was 60 seconds.
  • the volume median diameter of mixed powder 1 was 35.0 ⁇ m, and the standard deviation of particle size distribution was 19.0.
  • a continuous vapor deposition test was conducted using Mixed Powder 1 as follows. A crucible containing 2.0 g of mixed powder 1 was heated in a vacuum evaporation machine under a vacuum of 1 ⁇ 10 -4 Pa or less, the temperature was adjusted so that the film formation rate was 2 ⁇ /sec, and the melt was deposited on a glass substrate. A film was formed by vapor deposition. The glass substrate was replaced as appropriate, and film formation was continued. The substrate on which the film was first formed is referred to as substrate "No. 1", and hereinafter referred to as "No. 2", “No. 3", and so on. Substrate No. 1 to No. The total film thickness deposited on Sample No. 9 was 4500 nm.
  • the mass ratio of the first component and the second component was measured as follows. Calculate the mass when the specific gravity is assumed to be 1 from the film area and film thickness of the vapor-deposited film formed on the glass substrate, and add tetrahydrofuran ( A solution was prepared with THF) solvent, and the resulting solution was subjected to HPLC measurement using a high performance liquid chromatography (HPLC) device (device name: "LC-2040C Plus” manufactured by Shimadzu Corporation), and the first component and The HPLC area of each second component was calculated.
  • HPLC high performance liquid chromatography
  • a standard solution was prepared using a THF solvent so that the first component had a concentration of 100 ppm and the second component had a concentration of 100 ppm, and the peak areas of each were calculated by HPLC measurement.
  • the mass concentration in the solution of the first component and the second component in the mixed membrane was calculated from the peak area value of the standard solution, and the mass mixing ratio contained in the membrane was calculated from there. The results are shown in Table 1.
  • Comparative example 1 Powder consisting of BH-1 (first component) and powder consisting of BH-2 (second component) were weighed at a ratio of 64.7:35.3 (mass ratio), and then lightly crushed with a pestle in an agate mortar. By mixing for 10 seconds while grinding, the mixed powder Ref. I got 1. Mixed powder Ref. The volume median diameter of No. 1 was 76.0 ⁇ m, and the standard deviation of the particle size distribution was 125.0. Mixed powder Ref. A continuous vapor deposition test was conducted and evaluated in the same manner as in Example 1, except that Example 1 was used. The results are shown in Table 2.
  • Example 1 the mixing ratio in the vapor deposited film on each substrate during continuous vapor deposition did not vary greatly, and vapor deposition with a stable mixing ratio could be achieved. Further, it can be seen that the difference between the component ratio in the vapor deposition source (mixed powder) and the component ratio in the vapor deposited film is small, and the reproducibility of the component ratio is high. On the other hand, in Comparative Example 1, the variation in the mixing ratio in the deposited film on each substrate was larger than in Example 1, and the stability of the deposition ratio was low.
  • Example 1 the difference between the component ratio in the vapor deposition source (mixed powder) and the component ratio in the vapor deposited film was larger than in Example 1, and the reproducibility of the component ratio was also lower than in Example 1.
  • Example 2 From Experimental Example 1, it can be seen that the melting temperature of the mixed powder can be lowered if the mixed powder satisfies specific conditions (or undergoes a specific pulverization process). Specifically, mixed powder 1 is mixed powder Ref. Compared to No. 1, the melting start temperature was 7°C lower, and the complete melting temperature was 9°C lower. As a result, by using the mixed powder according to one embodiment of the present invention, it becomes possible to perform the vapor deposition process at a lower temperature, and it is expected that the handling of the mixed powder will be improved.
  • thermophysical properties other than the melting temperature for example, the DSC characteristics of the powder.
  • the DSC curve of mixed powder 1 is the same as that of mixed powder Ref.
  • the endothermic peak intensity was higher and the endothermic peak shape was sharper.
  • the reason for this is not necessarily clear, it is thought that the mixed powder is melted more integrally and more simultaneously. This is considered to contribute to improving the stability and reproducibility of the component ratio in the deposited film when the mixed powder is used in a vapor deposition process.
  • the hydrogen atom includes isotopes having different numbers of neutrons, ie, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • a hydrogen atom that is, a light hydrogen atom, a deuterium atom, or Assume that tritium atoms are bonded.
  • the number of carbon atoms forming a ring refers to the number of carbon atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). represents the number of carbon atoms among the atoms.
  • a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound represents the number of carbon atoms among the atoms.
  • the carbon contained in the substituent is not included in the number of carbon atoms forming the ring.
  • the "number of ring-forming carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 carbon atoms
  • a naphthalene ring has 10 carbon atoms
  • a pyridine ring has 5 carbon atoms
  • a furan ring has 4 carbon atoms.
  • the number of ring carbon atoms in the 9,9-diphenylfluorenyl group is 13
  • the number of ring carbon atoms in the 9,9'-spirobifluorenyl group is 25.
  • the benzene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the benzene ring.
  • the number of ring carbon atoms in the benzene ring substituted with an alkyl group is 6. Further, when the naphthalene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the naphthalene ring. Therefore, the number of ring carbon atoms in the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring-forming atoms refers to compounds with a structure in which atoms are bonded in a cyclic manner (e.g., monocyclic, fused ring, and ring assembly) (e.g., monocyclic compound, fused ring compound, bridged compound, carbocyclic compound). Represents the number of atoms that constitute the ring itself (compounds and heterocyclic compounds). Atoms that do not form a ring (for example, a hydrogen atom that terminates a bond between atoms that form a ring) and atoms that are included in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms.
  • the "number of ring-forming atoms" described below is the same unless otherwise specified.
  • the number of ring atoms in the pyridine ring is 6, the number of ring atoms in the quinazoline ring is 10, and the number of ring atoms in the furan ring is 5.
  • the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents is not included in the number of atoms forming the pyridine ring. Therefore, the number of ring atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is six.
  • carbon number XX to YY in the expression “substituted or unsubstituted ZZ group with carbon number XX to YY” represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in substituents.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • number of atoms XX to YY in the expression “substituted or unsubstituted ZZ group with number of atoms XX to YY” represents the number of atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of atoms of substituents in case.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and "YY" means an integer of 2 or more.
  • an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a "substituted or unsubstituted ZZ group". represents the case where is a "substituted ZZ group".
  • "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that the hydrogen atom in the ZZ group is not replaced with a substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a light hydrogen atom, a deuterium atom, or a tritium atom.
  • substituted in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substitution in the case of "BB group substituted with AA group” similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the number of ring carbon atoms in the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified herein. .
  • the number of ring atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified herein. be.
  • the number of carbon atoms in the "unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
  • the number of ring carbon atoms in the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6. be.
  • the number of ring carbon atoms in the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18. .
  • the number of ring atoms of the "unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 unless otherwise specified herein. ⁇ 18.
  • the number of carbon atoms in the "unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B). ) etc.
  • an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group”
  • a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group” is a "substituted or unsubstituted aryl group”
  • aryl group includes both “unsubstituted aryl group” and “substituted aryl group.”
  • “Substituted aryl group” means a group in which one or more hydrogen atoms of "unsubstituted aryl group” are replaced with a substituent.
  • Examples of the “substituted aryl group” include a group in which one or more hydrogen atoms of the "unsubstituted aryl group” in the specific example group G1A below are replaced with a substituent, and a substituted aryl group in the following specific example group G1B.
  • Examples include:
  • the examples of "unsubstituted aryl group” and “substituted aryl group” listed here are just examples, and the "substituted aryl group” described in this specification includes the following specific examples.
  • aryl group (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzocrysenyl group,
  • aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsily
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
  • a “heterocyclic group” as described herein is a monocyclic group or a fused ring group.
  • a “heterocyclic group” as described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • substituted or unsubstituted heterocyclic group examples include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group ( Examples include specific example group G2B).
  • unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”
  • substituted heterocyclic group refers to "substituted or unsubstituted heterocyclic group”
  • Heterocyclic group refers to a "substituted heterocyclic group."
  • heterocyclic group refers to "unsubstituted heterocyclic group” and “substituted heterocyclic group.” including both.
  • “Substituted heterocyclic group” means a group in which one or more hydrogen atoms of "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include a group in which the hydrogen atom of the "unsubstituted heterocyclic group” in specific example group G2A is replaced, and examples of substituted heterocyclic groups in specific example group G2B below. Can be mentioned.
  • Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), and unsubstituted heterocyclic groups containing a sulfur atom.
  • heterocyclic group (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), and substituted heterocyclic groups containing a sulfur atom.
  • group Specific Example Group G2B3
  • one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are substituents.
  • Includes substituted groups (Example Group G2B4).
  • ⁇ Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, Tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl
  • ⁇ Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): frill group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group and diazanaphthobenzofuranyl group.
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic group derived from the represented ring structure includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2 .
  • Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.
  • ⁇ Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
  • ⁇ Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
  • one or more hydrogen atoms of a monovalent heterocyclic group refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, and at least one of XA and YA is NH. It means one or more hydrogen atoms selected from the hydrogen atom bonded to the nitrogen atom in the case where XA and YA are CH2, and the hydrogen atom of the methylene group when one of XA and YA is CH2.
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). ).
  • an unsubstituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group” is an "unsubstituted alkyl group," and a substituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group” is (This refers to the case where it is a "substituted alkyl group.”)
  • alkyl group when it is simply referred to as an "alkyl group,” it includes both an "unsubstituted alkyl group” and a "substituted alkyl group.”
  • “Substituted alkyl group” means a group in which one or more hydrogen atoms in "unsubstituted alkyl group” are replaced with a substituent.
  • substituted alkyl group examples include groups in which one or more hydrogen atoms in the "unsubstituted alkyl group” (specific example group G3A) below are replaced with a substituent, and substituted alkyl groups (specific examples examples include group G3B).
  • the alkyl group in "unsubstituted alkyl group” means a chain alkyl group. Therefore, the "unsubstituted alkyl group” includes a linear "unsubstituted alkyl group” and a branched "unsubstituted alkyl group”.
  • ⁇ Unsubstituted alkyl group (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group.
  • ⁇ Substituted alkyl group (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group.
  • “Substituted or unsubstituted alkenyl group” Specific examples of the "substituted or unsubstituted alkenyl group" (specific example group G4) described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc.
  • the term "unsubstituted alkenyl group” refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group”
  • “substituted alkenyl group” refers to "substituted or unsubstituted alkenyl group”).
  • alkenyl group refers to a “substituted alkenyl group.”
  • alkenyl group includes both “unsubstituted alkenyl group” and “substituted alkenyl group.”
  • Substituted alkenyl group means a group in which one or more hydrogen atoms in "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include the following "unsubstituted alkenyl group” (specific example group G4A) having a substituent, and the substituted alkenyl group (specific example group G4B). It will be done.
  • ⁇ Unsubstituted alkenyl group (specific example group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group and 3-butenyl group.
  • ⁇ Substituted alkenyl group (specific example group G4B): 1,3-butandienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group and 1,2-dimethylallyl group.
  • ⁇ alkynyl group'' and ⁇ substituted alkynyl group means a group in which one or more hydrogen atoms in "unsubstituted alkynyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group” (specific example group G5A) are replaced with a substituent.
  • ⁇ “Substituted or unsubstituted cycloalkyl group” Specific examples of the "substituted or unsubstituted cycloalkyl group” (specific example group G6) described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups ( Examples include specific example group G6B).
  • unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group” is “unsubstituted cycloalkyl group”, and the term “substituted cycloalkyl group” refers to “substituted or unsubstituted cycloalkyl group”).
  • cycloalkyl group refers to a "substituted cycloalkyl group.
  • simply “cycloalkyl group” refers to "unsubstituted cycloalkyl group” and “substituted cycloalkyl group.” including both.
  • Substituted cycloalkyl group means a group in which one or more hydrogen atoms in "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include the following "unsubstituted cycloalkyl group” (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and a substituted cycloalkyl group. (Specific example group G6B) and the like can be mentioned.
  • cycloalkyl group (specific example group G6A): cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • cycloalkyl group (specific example group G6B): 4-methylcyclohexyl group.
  • G7 Group represented by -Si(R 901 )(R 902 )(R 903 )
  • Specific examples of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification include: -Si(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G2's in Si(G2) (G2) (G2) are mutually the same or different.
  • a plurality of G3's in Si(G3) (G3) are mutually the same or different.
  • - A plurality of G6's in Si(G6) (G6) (G6) are mutually the same or different.
  • G8 Specific examples of the group represented by -O-(R 904 ) described in this specification (specific example group G8) include: -O(G1), -O(G2), -O (G3) and -O (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G9 Group represented by -S-(R 905 )
  • Specific examples of the group represented by -S-(R 905 ) described in this specification include: -S (G1), -S (G2), -S (G3) and -S (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G10 Group represented by -N(R 906 )(R 907 )
  • Specific examples of the group represented by -N(R 906 )(R 907 ) described in this specification include: -N(G1)(G1), -N(G2)(G2), -N (G1) (G2), -N (G3) (G3), and -N (G6) (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • -N(G1) A plurality of G1's in (G1) are mutually the same or different.
  • -N(G2) A plurality of G2's in (G2) are the same or different.
  • -N(G3) A plurality of G3's in (G3) are mutually the same or different.
  • -N(G6) Multiple G6s in (G6) are the same or different from each other
  • halogen atom specifically examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • substituted or unsubstituted fluoroalkyl group refers to a "substituted or unsubstituted alkyl group" in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced with a fluorine atom. It also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group” are replaced with fluorine atoms (perfluoro group).
  • the number of carbon atoms in the "unsubstituted fluoroalkyl group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • “Substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the "fluoroalkyl group” are replaced with a substituent.
  • substituted fluoroalkyl group described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl group” is further replaced with a substituent, and Also included are groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group” are further replaced with a substituent.
  • substituents of a substituent in a "substituted fluoroalkyl group” are further replaced with a substituent.
  • the "unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a fluorine atom.
  • the "substituted or unsubstituted haloalkyl group” described herein is a "substituted or unsubstituted alkyl group" in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced with a halogen atom. It means a group, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the number of carbon atoms in the "unsubstituted haloalkyl group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • “Substituted haloalkyl group” means a group in which one or more hydrogen atoms of the "haloalkyl group” are replaced with a substituent.
  • the "substituted haloalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl group” is further replaced with a substituent, and a “substituted haloalkyl group” Also included are groups in which one or more hydrogen atoms of a substituent in the "haloalkyl group” are further replaced with a substituent.
  • Specific examples of the "unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
  • a haloalkyl group is sometimes referred to as a halogenated alkyl group.
  • ⁇ “Substituted or unsubstituted alkoxy group” A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkoxy group” described in specific example group G3. "unsubstituted alkyl group”. The number of carbon atoms in the "unsubstituted alkoxy group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • ⁇ “Substituted or unsubstituted alkylthio group” A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkylthio group” described in specific example group G3. "unsubstituted alkyl group”.
  • the number of carbon atoms in the "unsubstituted alkylthio group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryloxy group” described in specific example group G1. or an unsubstituted aryl group.
  • the number of ring carbon atoms in the "unsubstituted aryloxy group" is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted arylthio group” described in the specific example group G1.
  • G1 is the "substituted or unsubstituted arylthio group” described in the specific example group G1.
  • the number of ring carbon atoms in the "unsubstituted arylthio group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • ⁇ “Substituted or unsubstituted trialkylsilyl group” A specific example of the "trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group.” - A plurality of G3's in Si(G3) (G3) (G3) are mutually the same or different. The number of carbon atoms in each alkyl group of the "trialkylsilyl group” is from 1 to 50, preferably from 1 to 20, and more preferably from 1 to 6, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
  • an "aralkyl group” is a group in which the hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one embodiment of a “substituted alkyl group.”
  • An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group”, and the number of carbon atoms in the "unsubstituted aralkyl group” is determined unless otherwise specified herein. , 7 to 50, preferably 7 to 30, more preferably 7 to 18.
  • substituted or unsubstituted aralkyl groups include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ - Naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • the substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl group, unless otherwise specified herein.
  • the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, or a phenol group, unless otherwise specified herein.
  • Nanthrolinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-b
  • carbazolyl group is specifically any of the following groups unless otherwise specified in the specification.
  • the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise stated in the specification.
  • dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the specification.
  • the substituted or unsubstituted alkyl group described herein is preferably a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t- Butyl group, etc.
  • the "substituted or unsubstituted arylene group” described in this specification refers to 2 derived from the above "substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. It is the basis of valence.
  • a "substituted or unsubstituted arylene group” (specific example group G12) one hydrogen atom on the aryl ring is removed from the "substituted or unsubstituted aryl group” described in specific example group G1. Examples include divalent groups derived from the derivatives.
  • the "substituted or unsubstituted divalent heterocyclic group” described herein refers to the "substituted or unsubstituted heterocyclic group" described above in which one hydrogen atom on the heterocycle is removed. It is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocycle from the "substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include divalent groups derived by removing atoms.
  • the "substituted or unsubstituted alkylene group” described in this specification refers to 2 derived from the above "substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. It is the basis of valence.
  • a "substituted or unsubstituted alkylene group” (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group” described in specific example group G3. Examples include divalent groups derived from the derivatives.
  • the substituted or unsubstituted arylene group described herein is preferably a group represented by any of the following general formulas (TEMP-42) to (TEMP-68).
  • Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
  • * represents a binding site.
  • Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
  • Formulas Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents a binding site.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents a binding site.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein. It is.
  • Q 1 to Q 9 are each independently a hydrogen atom or a substituent.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • the set of two or more adjacent R 930 is one set. is a set of R 921 and R 922 , a set of R 922 and R 923 , a set of R 923 and R 924 , a set of R 924 and R 930 , a set of R 930 and R 925 , a set of R 925 and A set of R 926 , a set of R 926 and R 927 , a set of R 927 and R 928 , a set of R 928 and R 929 , and a set of R 929 and R 921 .
  • the above-mentioned "one or more sets” means that two or more sets of the above-mentioned two or more adjacent sets may form a ring at the same time.
  • R 921 and R 922 combine with each other to form ring Q A
  • R 925 and R 926 combine with each other to form ring Q B
  • the above general formula (TEMP-103) The anthracene compound represented is represented by the following general formula (TEMP-104).
  • a set of two or more adjacent items forms a ring is not only the case where a set of "two" adjacent items are combined as in the example above, but also the case where a set of "three or more adjacent items” form a ring. This also includes the case where two sets are combined.
  • R 921 and R 922 combine with each other to form a ring Q A
  • R 922 and R 923 combine with each other to form a ring Q C
  • the three adjacent to each other (R 921 , R 922 and R 923 ) combine with each other to form a ring and are condensed to the anthracene mother skeleton.
  • anthracene compound represented by the general formula (TEMP-103) is as follows: It is represented by the general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .
  • the "single ring” or “fused ring” that is formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even if “one set of two adjacent rings” forms a “monocycle” or “fused ring,” the “monocycle” or “fused ring” is a saturated ring, or Can form unsaturated rings.
  • ring Q A and ring Q B formed in the general formula (TEMP-104) are each a “monocyclic ring” or a “fused ring.”
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are "fused rings”.
  • Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring due to the condensation of ring Q A and ring Q C.
  • ring Q A in the general formula (TMEP-104) is a benzene ring
  • ring Q A is a monocyclic ring.
  • ring Q A in the general formula (TMEP-104) is a naphthalene ring
  • ring Q A is a fused ring.
  • Unsaturated ring includes an aromatic hydrocarbon ring, an aromatic heterocycle, and an aliphatic hydrocarbon ring having an unsaturated bond, that is, a double bond and/or triple bond in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having unsaturated bonds (for example, dihydropyran, imidazoline, pyrazoline, quinolidine, indoline, isoindoline, etc.).
  • the "saturated ring” includes an aliphatic hydrocarbon ring having no unsaturated bond or a non-aromatic heterocycle having no unsaturated bond.
  • aromatic hydrocarbon ring examples include structures in which the groups listed as specific examples in specific example group G1 are terminated with hydrogen atoms.
  • aromatic heterocycle include structures in which the aromatic heterocyclic group listed as a specific example in specific example group G2 is terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G6 are terminated with hydrogen atoms.
  • "Form a ring" means to form a ring with only a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more arbitrary atoms.
  • the ring Q A shown in the general formula (TEMP-104) formed by R 921 and R 922 bonding to each other is a carbon atom of the anthracene skeleton to which R 921 is bonded, and an anthracene bond to which R 922 is bonded. It means a ring formed by a carbon atom of the skeleton and one or more arbitrary atoms.
  • R 921 and R 922 form a ring Q A
  • the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms.
  • R 921 and R 922 form a monocyclic unsaturated ring
  • the ring formed by R 921 and R 922 is a benzene ring.
  • any atom is preferably at least one atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom.
  • any atom for example, in the case of a carbon atom or a nitrogen atom
  • a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent” described below.
  • the ring formed is a heterocycle.
  • "one or more arbitrary atoms" constituting a monocyclic ring or a condensed ring are preferably 2 to 15 atoms, more preferably 3 to 12 atoms.
  • a “monocycle” is preferred among “monocycle” and “fused ring.” Unless otherwise specified herein, the "unsaturated ring” is preferred between the “saturated ring” and the “unsaturated ring”. Unless otherwise stated herein, a “monocycle” is preferably a benzene ring. Unless otherwise stated herein, an “unsaturated ring” is preferably a benzene ring.
  • one or more pairs of two or more adjacent groups are “bonded with each other to form a substituted or unsubstituted monocycle” or “bonded with each other to form a substituted or unsubstituted fused ring”
  • one or more of the pairs of two or more adjacent atoms are bonded to each other to form a bond with a plurality of atoms of the parent skeleton and one or more of the 15 or more atoms.
  • a substituted or unsubstituted "unsaturated ring” is formed with at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the substituent is, for example, the "arbitrary substituent” described below.
  • Specific examples of the substituent in the case where the above-mentioned “single ring” or “fused ring” has a substituent are the substituents described in the section of "Substituent described herein” above.
  • the substituent is, for example, the "arbitrary substituent” described below.
  • substituents in the case where the above-mentioned "single ring” or “fused ring” has a substituent are the substituents described in the section of "Substituent described herein" above. The above applies to cases in which "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle" and "one or more sets of two or more adjacent groups” are combined with each other to form a substituted or unsubstituted condensed ring ("the case where they are combined to form a ring").
  • the substituent in the case of "substituted or unsubstituted” (herein referred to as "arbitrary substituent")
  • arbitrary substituent For example, unsubstituted alkyl group having 1 to 50 carbon atoms, unsubstituted alkenyl group having 2 to 50 carbon atoms, unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms,
  • R 901s When two or more R 901s exist, the two or more R 901s are the same or different, When two or more R 902s exist, the two or more R 902s are the same or different, When two or more R 903s exist, the two or more R 903s are the same or different, When two or more R 904s exist, the two or more R 904s are the same or different, When two or more R 905s exist, the two or more R 905s are the same or different, When two or more R 906s exist, the two or more R 906s are the same or different, When two or more R 907s exist, the two or more R 907s are the same or different.
  • the substituent in the case of "substituted or unsubstituted” is an alkyl group having 1 to 50 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the case of "substituted or unsubstituted” is an alkyl group having 1 to 18 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may form a "saturated ring" or "unsaturated ring", preferably a substituted or unsubstituted saturated ring. Forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
  • any substituent may further have a substituent.
  • the substituents that the arbitrary substituents further have are the same as the above arbitrary substituents.
  • the numerical range expressed using "AA-BB” has the numerical value AA written before “AA-BB” as the lower limit, and the numerical value BB written after "AA-BB”. means a range that includes as an upper limit value.
  • AA ⁇ BB means that the numerical value AA is the same as the numerical value BB or is larger than the numerical value BB
  • AA ⁇ BB means that the numerical value AA is the same as the numerical value BB. It means that there is or is less than the numerical value BB.

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Abstract

La présente invention concerne une poudre mélangée pour dépôt sous vide contenant un premier composé organique et un second composé organique, la poudre mélangée ayant un diamètre médian en volume de 10 à 60 µm inclus.
PCT/JP2023/007955 2022-03-08 2023-03-03 Poudre mélangée, procédé de fabrication de poudre mélangée, composition, élément électroluminescent organique et procédé de fabrication d'élément électroluminescent organique WO2023171544A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006066118A (ja) * 2004-08-25 2006-03-09 Toray Ind Inc 有機ｅｌ材料、有機ｅｌ材料の製造方法および有機ｅｌ素子の製造方法
WO2010035446A1 (fr) * 2008-09-24 2010-04-01 出光興産株式会社 Matériau électroluminescent organique composite
WO2010116759A1 (fr) * 2009-04-10 2010-10-14 出光興産株式会社 Matière électroluminescente organique composite et son procédé de fabrication
JP2020127020A (ja) * 2013-10-11 2020-08-20 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 有機光電子素子用有機アロイ、有機光電子素子および表示装置

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006066118A (ja) * 2004-08-25 2006-03-09 Toray Ind Inc 有機ｅｌ材料、有機ｅｌ材料の製造方法および有機ｅｌ素子の製造方法
WO2010035446A1 (fr) * 2008-09-24 2010-04-01 出光興産株式会社 Matériau électroluminescent organique composite
WO2010116759A1 (fr) * 2009-04-10 2010-10-14 出光興産株式会社 Matière électroluminescente organique composite et son procédé de fabrication
JP2020127020A (ja) * 2013-10-11 2020-08-20 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 有機光電子素子用有機アロイ、有機光電子素子および表示装置

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