WO2024190882A1 - Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique Download PDF

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WO2024190882A1
WO2024190882A1 PCT/JP2024/010081 JP2024010081W WO2024190882A1 WO 2024190882 A1 WO2024190882 A1 WO 2024190882A1 JP 2024010081 W JP2024010081 W JP 2024010081W WO 2024190882 A1 WO2024190882 A1 WO 2024190882A1
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裕基 中野
慎太郎 伴
亮 永田
良多 高橋
潔 池田
士雄磨 橋本
祐一郎 河村
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/20—Delayed fluorescence emission

Definitions

  • the present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device.
  • organic electroluminescence element When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical laws of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Fluorescent organic EL elements that use light emitted from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%.
  • Patent Document 7 discloses an organic EL element that utilizes the triplet-triplet fusion (TTF) mechanism, which is one of the mechanisms of delayed fluorescence.
  • TTF triplet-triplet fusion
  • the object of the present invention is to provide a compound that can cause an organic electroluminescence element to emit light with high efficiency. Another object of the present invention is to provide a material for an organic electroluminescence element that contains the compound. Another object of the present invention is to provide an organic electroluminescence element that emits light with high efficiency, and to provide an electronic device equipped with the organic electroluminescence element.
  • Ar 1 is a group represented by the general formula (11) or (12), A pair of two or more adjacent groups among R 1 to R 4 , and one or more groups of R 6 and R 7 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, one or more of a group consisting of two or more adjacent groups among R 8 to R 11 and one or more of a group consisting of two or more adjacent groups among R 12 to R 15 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • the compound represented by the general formula (1) satisfies (condition i) or (condition ii).
  • the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted fused ring formed are each independently: a ring represented by the general formula (14) above, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, R 5 , and R 1 to R 4 and R 6 to R 15 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring each independently represent Hydrogen atoms, A group represented by the general formula (13), a substituted or unsubstituted alkyl group having 1 to 20
  • R 1 to R 15 each independently represent Hydrogen atoms, A group represented by the general formula (13), a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, However, at least one of R 1 to R 15 is a group represented by the general formula (13), and when there are a plurality of groups represented by the general formula (13), the plurality of groups represented by the general formula (13) are the same or different from each other.
  • R 21 to R 25 are they are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, or they are not bonded to each other
  • One or more pairs of adjacent two or more of R 26 to R 29 are they are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, or they are not bonded to each other
  • One or more pairs of adjacent two or more R 30 are they are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, or they are not bonded to each other
  • R 21 to R 30 which do not form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms each independently represent Hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20
  • R 31 to R 39 each independently represent Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a group represented by -Si(R 41 )(R 42 )(R 43 ), or a group represented by -Ge(R 44 )(R 45 )(R 46 ), * indicates the bond position.
  • R 41 to R 43 is joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • One pair of adjacent two of R 44 to R 46 is joined together to form
  • a material for an organic electroluminescence device that contains a compound according to one aspect of the present invention.
  • an organic electroluminescence element including an anode, a cathode, and an emitting layer disposed between the anode and the cathode, the emitting layer containing a host material and a sensitizing material, the host material being a compound according to one aspect of the present invention, and the sensitizing material and the host material being different compounds.
  • an electronic device is provided that is equipped with an organic electroluminescence element according to one aspect of the present invention.
  • FIG. 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a first embodiment of the present invention.
  • FIG. 1 is a schematic diagram of an apparatus for measuring transient PL.
  • FIG. 13 is a diagram showing an example of a decay curve of a transient PL.
  • FIG. 2 is a diagram showing the energy levels of a host material, a sensitizing material (delayed fluorescent compound), and a fluorescent material in an emitting layer of an example of an organic electroluminescence element according to a first embodiment of the present invention, and the relationship between energy transfer.
  • hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.
  • any possible bonding position that is not explicitly indicated with a symbol such as "R" or "D” representing a deuterium atom is assumed to have a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, bonded to it.
  • the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound).
  • a compound having a structure in which atoms are bonded in a ring for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound.
  • the carbon contained in the substituent is not included in the number of ring carbon atoms.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • a 9,9-diphenylfluorenyl group has 13 ring carbon atoms
  • a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring.
  • the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) with a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly).
  • the number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent.
  • the "number of ring atoms" described below is the same unless otherwise specified.
  • the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5.
  • the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6.
  • the number of ring atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
  • the "carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having carbon numbers XX to YY” refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • "YY” means an integer of 2 or more.
  • the "atomic number XX to YY” in the expression “substituted or unsubstituted ZZ group having atomic number XX to YY” refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituents when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • “YY” means an integer of 2 or more.
  • unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group” is an "unsubstituted ZZ group”
  • substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group” is a "substituted ZZ group”.
  • unsubstituted in the case of "a substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a protium atom, a deuterium atom, or a tritium atom.
  • substitution in the case of "a 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 "a BB group substituted with an AA group” means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the "unsubstituted aryl group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
  • the "unsubstituted heterocyclic group” described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
  • the "unsubstituted alkyl group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described in this specification, unless otherwise specified in this specification, is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described in this specification, unless otherwise specified in this specification, is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
  • the "unsubstituted cycloalkyl group” described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B).
  • unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is an "unsubstituted aryl group"
  • substituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is a "substituted aryl group”.
  • aryl group simply refers to both an "unsubstituted aryl group” and a "substituted aryl group”.
  • substituted aryl group refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group” are replaced with a substituent.
  • substituted aryl group include the "unsubstituted aryl group” in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below.
  • the examples of the "unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are merely examples, and the "substituted aryl group” described in this specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group” in the specific example group G1B below is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group” in the specific example group G1B below is further replaced with a substituent.
  • Unsubstituted aryl groups (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, A phenanthryl group, Benzophenanthryl group, A phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group,
  • Substituted aryl groups (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, A 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, triphenyls
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom.
  • the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
  • the “heterocyclic groups” described herein are either monocyclic or fused ring groups.
  • the “heterocyclic group” described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B).
  • the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group"
  • the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group”.
  • substituted heterocyclic group refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are merely examples, and the “substituted heterocyclic group” described in this specification also includes the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.
  • 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), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (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), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
  • Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, A pyrimidinyl group, Pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, A quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl
  • Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
  • Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): A thienyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, Benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanap
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2 , provided that 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 ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from the NH or CH2 .
  • Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): A (9-phenyl)carbazolyl group, A (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, A phenylcarbazol-9-yl group, methylbenzimidazolyl group, Ethyl benzimidazolyl group, phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
  • Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, The t-butyldibenzofuranyl group, and the monovalent radical of spiro[9H-xanthene-9,9'-[9H]fluorene].
  • Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, The t-butyldibenzothiophenyl group, and the monovalent radical of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
  • one or more hydrogen atoms of a monovalent heterocyclic group means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a 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).
  • the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group"
  • the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group” is a "substituted alkyl group”.
  • substituted alkyl group refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group” are replaced with a substituent.
  • specific examples of the "substituted alkyl group” include the following "unsubstituted alkyl group” (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B).
  • the alkyl group in the "unsubstituted alkyl group” refers to a chain-like alkyl group.
  • the "unsubstituted alkyl group” includes a straight-chain “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the "substituted alkyl group” described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent.
  • Unsubstituted alkyl groups (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 groups (specific example group G3B): Heptafluoropropyl group (including isomers), pentafluoroethyl group, A 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
  • Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B).
  • the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group” is an "unsubstituted alkenyl group", and the "substituted alkenyl group” refers to the case where the "substituted or unsubstituted alkenyl group” is a "substituted alkenyl group”.
  • alkenyl group when the term “alkenyl group” is simply used, it includes both an "unsubstituted alkenyl group” and a "substituted alkenyl group”.
  • substituted alkenyl group refers to a group in which one or more hydrogen atoms in an "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 examples of substituted alkenyl groups (specific example group G4B).
  • the examples of the "unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” listed here are merely examples, and the "substituted alkenyl group” described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent.
  • Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, A 2-butenyl group, and a 3-butenyl group.
  • Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
  • the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group” is an "unsubstituted alkynyl group."
  • alkynyl group refers to an "unsubstituted alkynyl group” in which one or more hydrogen atoms have been replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include the following "unsubstituted alkynyl group” (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.
  • Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B).
  • unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group” is an "unsubstituted cycloalkyl group”
  • substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group” is a "substituted cycloalkyl group”.
  • substituted cycloalkyl group refers to a group in which one or more hydrogen atoms in the "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 the examples of the substituted cycloalkyl group (specific example group G6B).
  • G7 of the group represented by --Si(R 901 )(R 902 )(R 903 ) described in this specification include: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6)(G6)
  • 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.
  • the multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.
  • the multiple G2s in —Si(G1)(G2)(G2) are the same as or different from each other.
  • the multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.
  • the multiple G2s in —Si(G2)(G2)(G2) are the same as or different from each other.
  • the multiple G3s in —Si(G3)(G3)(G3) are the same as or different from each other.
  • the multiple G6s in —Si(G6)(G6)(G6) are the same as or different from each other.
  • G8 of the group represented by -O-(R 904 ) described in this specification include: -O(G1), -O (G2), -O(G3) and -O(G6) Examples include: Where: 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 A group represented by -S-(R 905 )
  • Specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification include: -S (G1), -S (G2), -S(G3) and -S(G6) Examples include: Where: 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.
  • Specific examples (specific example group G10) 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) Examples include: Where: 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.
  • the multiple G1s in -N(G1)(G1) are the same or different from each other.
  • the multiple G2s in -N(G2)(G2) are the same or different from each other.
  • the multiple G3s in -N(G3)(G3) are the same or different.
  • the multiple G6s in -N(G6)(G6) are the same or different.
  • halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • substituted or unsubstituted fluoroalkyl groups means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with fluorine atoms.
  • the number of carbon atoms in the "unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification.
  • substituted fluoroalkyl group means a group in which one or more hydrogen atoms in the "fluoroalkyl group” are replaced with a substituent.
  • substituted fluoroalkyl group as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group” are further replaced with a substituent.
  • substituents include the examples of groups in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with fluorine atoms.
  • substituted or unsubstituted haloalkyl group means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the number of carbon atoms in the "unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification.
  • substituted haloalkyl group means a group in which one or more hydrogen atoms in the "haloalkyl group” are replaced with a substituent.
  • substituted haloalkyl group as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group” are further replaced with a substituent.
  • substituents in the "substituted haloalkyl group” are further replaced with a substituent.
  • Specific examples of the "unsubstituted haloalkyl group” include the examples of the group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
  • Haloalkyl groups are sometimes referred to as halogenated alkyl groups.
  • a specific example of the "substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
  • 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 a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
  • 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 aryl group” described in specific example group G1.
  • the number of ring carbon atoms of the "unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
  • a specific example of the "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • the number of ring carbon atoms of the "unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
  • a specific example of the "trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.
  • the number of carbon atoms in each alkyl group of the "trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.
  • 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 "substituted or unsubstituted alkyl group” described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
  • an “aralkyl group” is a group in which a hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one aspect 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 of the "unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
  • substituted or unsubstituted aralkyl group 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, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a o-terphenyl-4-yl group, a o-terphenyl-3-yl group, a o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a
  • the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothi
  • zadibenzothiophenyl 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)carbazol-4-yl group)
  • (9-biphenylyl)carbazolyl group (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
  • carbazolyl group is specifically any of the following groups:
  • the (9-phenyl)carbazolyl group is specifically any of the following groups:
  • dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
  • the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group".
  • Specific examples of the "substituted or unsubstituted arylene group” include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in specific example group G1.
  • Substituted or unsubstituted divalent heterocyclic group is, unless otherwise specified, a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group".
  • Specific examples of the "substituted or unsubstituted divalent heterocyclic group” include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group".
  • Specific examples of the "substituted or unsubstituted alkylene group” include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the substituted or unsubstituted arylene group described herein is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • * represents a bonding position.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents a bonding position.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • * represents a bonding position.
  • the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.
  • Q 1 to Q 9 each independently represent a hydrogen atom or a substituent.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other".
  • the pair of adjacent two that constitutes one group includes the pair of R 921 and R 922 , the pair of R 922 and R 923 , the pair of R 923 and R 924 , the pair of R 924 and R 930 , the pair of R 930 and R 925 , the pair of R 925 and R 926, the pair of R 926 and R 927 , the pair of R 927 and R 928 , the pair of R 928 and R 929 , and the pair of R 929 and R 921 .
  • one or more pairs means that two or more pairs of the adjacent two or more pairs may simultaneously form a ring.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
  • a set of two or more adjacent rings forms a ring includes not only the case where a set of "two" adjacent rings is bonded as in the above example, but also the case where a set of "three or more adjacent rings is bonded.
  • it means the case where R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , and a set of three adjacent rings (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and are condensed to the anthracene skeleton.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “fused ring” formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even if “one of the pairs of adjacent two" forms a “monocyclic ring” or a “fused ring", the “monocyclic ring” or the “fused ring” can form a saturated ring or an unsaturated ring.
  • the ring Q A and the ring Q B formed in the general formula (TEMP-104) are “monocyclic rings” or “fused rings", respectively.
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) are fused rings by the fusion of the ring Q A and the ring Q C. If the ring Q A in the general formula (TMEP-104) is a benzene ring, the ring Q A is a monocyclic ring. When ring Q 1 A in the above general formula (TMEP-104) is a naphthalene ring, ring Q 1 A is a fused ring.
  • saturated ring refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • saturated ring refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.
  • aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom.
  • aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom.
  • Forming a ring means forming a ring only with a plurality of atoms of the mother skeleton, or with a plurality of atoms of the mother skeleton and one or more arbitrary elements.
  • the ring QA formed by bonding R 921 and R 922 to each other in the general formula (TEMP-104) means a ring formed by 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 one or more arbitrary elements.
  • R 921 and R 922 form a ring QA
  • 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 form a monocyclic unsaturated ring
  • the ring formed by R 921 and R 922 is a benzene ring.
  • the "arbitrary element” is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur.
  • the arbitrary element for example, in the case of a carbon element or a nitrogen element
  • 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.
  • the "one or more arbitrary elements" constituting the single ring or the condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.
  • the "monocyclic ring” and the “condensed ring” are preferred.
  • the "saturated ring” and the “unsaturated ring” are preferred.
  • a “monocyclic ring” is preferably a benzene ring.
  • the "unsaturated ring” is preferably a benzene ring.
  • one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted monocyclic ring” or “combine with each other to form a substituted or unsubstituted fused ring
  • one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring” consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.
  • the substituent is, for example, the “optional substituent” described later.
  • specific examples of the substituent are the substituents described in the above-mentioned section “Substituents described in this specification”.
  • the substituent is, for example, the "optional substituent” described later.
  • substituents in the case of "substituted or unsubstituted” are, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms, an 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 atoms, cyano groups, nitro groups, a group selected from the group consisting of an unsubstituted
  • the two or more R 901 are the same or different from each other
  • the two or more R 902 are present, the two or more R 902 are the same or different from each other
  • the two or more R 903 are present, the two or more R 903 are the same or different from each other
  • the two or more R 904 are present, the two or more R 904 are the same or different from each other
  • the two or more R 905 are present, the two or more R 905 are the same or different from each other
  • two or more R 906 are present, the two or more R 906 are the same or different from each other
  • the two or more R 907 are present, the two or more R 907 are the same or different.
  • the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 50 carbon atoms, The group is 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 above "substituted or unsubstituted” is: an alkyl group having 1 to 18 carbon atoms, The group is 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 be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-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.
  • the optional substituent may further have a substituent.
  • the substituent that the optional substituent further has is the same as the optional substituent described above.
  • a numerical range expressed using "AA-BB” refers to a range that includes the number AA written before “AA-BB” as the lower limit and the number BB written after "AA-BB” as the upper limit.
  • a mathematical expression expressed as "A ⁇ B” means that the value of A is equal to the value of B, or the value of A is greater than the value of B.
  • a mathematical expression expressed as "A ⁇ B” means that the value of A is equal to the value of B, or the value of A is smaller than the value of B.
  • the compound according to this embodiment is a compound represented by the following general formula (1).
  • Ar 1 is a group represented by the general formula (11) or (12), A pair of two or more adjacent groups among R 1 to R 4 , and one or more groups of R 6 and R 7 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded together to form a substituted or unsubstituted fused ring, or are not bonded together, one or more of a group consisting of two or more adjacent groups among R 8 to R 11 and one or more of a group consisting of two or more adjacent groups among R 12 to R 15 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • the compound represented by the general formula (1) satisfies (condition i) or (condition ii).
  • the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted fused ring formed are each independently: a ring represented by the general formula (14) above, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, R 5 , and R 1 to R 4 and R 6 to R 15 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring each independently represent Hydrogen atoms, A group represented by the general formula (13), a substituted or unsubstituted alkyl group having 1 to 20
  • R 1 to R 15 each independently represent Hydrogen atoms, A group represented by the general formula (13), a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, However, at least one of R 1 to R 15 is a group represented by the general formula (13), and when a plurality of groups represented by the general formula (13) are present, the plurality of groups represented by the general formula (13) are the same or different from each other.
  • R 21 to R 25 are they are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, or they are not bonded to each other
  • One or more pairs of adjacent two or more of R 26 to R 29 are they are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, or they are not bonded to each other
  • One or more pairs of adjacent two or more R 30 are they are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, or they are not bonded to each other
  • R 21 to R 30 which do not form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms each independently represent Hydrogen atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20
  • R 31 to R 39 each independently represent Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a group represented by -Si(R 41 )(R 42 )(R 43 ), or a group represented by -Ge(R 44 )(R 45 )(R 46 ), * indicates the bond position.
  • R 41 to R 43 is joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • One pair of adjacent two of R 44 to R 46 is joined together to form
  • the compound according to this embodiment has a structure in which an ortho-biphenyl group (the group represented by the general formula (13)) is introduced at least at any position of a biscarbazole skeleton. Due to this structure, the compound of this embodiment has a higher glass transition temperature (Tg) than the compound before the introduction of the ortho-biphenyl group, and therefore, by incorporating this compound in the light-emitting layer, the thermal stability of the film (light-emitting layer) is improved. In addition, the compound according to the present embodiment has a structure in which an ortho-biphenyl group is introduced into a biscarbazole skeleton, and thus the three-dimensional bulkiness of the entire compound is increased.
  • Tg glass transition temperature
  • the compound according to the present embodiment can reduce the loss of energy related to the emission of the dopant compound, and can cause the organic EL element to emit light with high efficiency.
  • the compound according to the present embodiment does not increase in molecular weight as much as a compound having a terphenyl group or the like introduced therein, so that when the compound is vapor-deposited to form a light-emitting layer, an increase in the vapor deposition temperature can be suppressed, and the thermal load on the compound can be reduced.
  • the compound according to this embodiment when used as a host compound, it is possible to cause an organic EL device to emit light with high efficiency.
  • the organic EL device when the compound is contained in a light-emitting layer together with a blue light-emitting material, the organic EL device can emit light with high efficiency.
  • the compound according to this embodiment for example, when a pair of R 1 and R 2 in the general formula (1) are bonded to each other to form a "substituted or unsubstituted fused ring" and the formed fused ring is a ring represented by the general formula (14), the compound according to this embodiment is represented by the following general formula (1A) or (1E).
  • the compound according to this embodiment is represented by the following general formula (1A) or (1E).
  • at least one of R 3 to R 19 is a group represented by the general formula (13).
  • at least one of R 3 to R 19 is a group represented by the general formula (13).
  • the compound according to the present embodiment for example, when a pair of R3 and R4 in the general formula (1) are bonded to each other to form a "substituted or unsubstituted monocycle" and the formed ring is a "substituted or unsubstituted aliphatic hydrocarbon ring having 6 ring carbon atoms", the compound according to the present embodiment is represented by the following general formula (1X):
  • Rx is not a group represented by the general formula (13)
  • at least one of R1 to R2 and R5 to R15 is a group represented by the general formula (13).
  • the compound according to the present embodiment is a compound in which the "substituted or unsubstituted aliphatic hydrocarbon ring having 6 ring carbon atoms" in the following general formula (1X) is replaced with a "substituted or unsubstituted aliphatic hydrocarbon ring having 20 ring carbon atoms".
  • the aliphatic hydrocarbon ring has a substituent, none of the substituents is a group represented by the general formula (13), and at least one of R1 to R2 and R5 to R15 is a group represented by the general formula (13).
  • Ar 1 and R 3 to R 15 are each independently defined as Ar 1 and R 3 to R 15 in the general formula (1)
  • Y 1 and R 16 to R 19 are each independently defined as Y 1 and R 16 to R 19 in the general formula (14).
  • Ar 1 , R 1 to R 2 and R 5 to R 15 each independently have the same definition as Ar 1 , R 1 to R 2 and R 5 to R 15 in formula (1);
  • One or more of the sets of two or more adjacent Rx's are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • Rx which does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring is Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a group represented by -Si(R 41 )(R 42 )(R 43 ), or a group represented by -Ge(R 44
  • One embodiment of the compound according to this embodiment is a compound represented by the following general formula (10).
  • R 1 to R 15 are each independently defined as R 1 to R 15 in the general formula (1)
  • R 21 to R 25 are each independently defined as R 21 to R 25 in the general formula (11).
  • one or more of a group consisting of two or more adjacent members of R 1 to R 4 , a group consisting of R 6 and R 7 , a group consisting of two or more adjacent members of R 8 to R 11 , and a group consisting of two or more adjacent members of R 12 to R 15 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring.
  • at least one of R 1 to R 19 is a group represented by the general formula (13).
  • R 1 to R 19 it is preferable that one is a group represented by the general formula (13), it is more preferable that one of R 1 to R 4 , R 6 to R 11 and R 16 to R 18 is a group represented by the general formula (13), it is even more preferable that R 10 , R 11 , R 16 or R 18 is a group represented by the general formula (13), and it is even more preferable that R 10 or R 11 is a group represented by the general formula (13).
  • none of a pair of two or more adjacent pairs of R 1 to R 4 , a pair of R 6 and R 7 , a pair of two or more adjacent pairs of R 8 to R 11 , and a pair of two or more adjacent pairs of R 12 to R 15 are bonded to each other.
  • at least one of R 1 to R 15 is a group represented by the general formula (13). It is preferable that one of R 1 to R 15 is a group represented by the general formula (13), it is more preferable that one of R 1 to R 4 and R 6 to R 11 is a group represented by the general formula (13), and it is even more preferable that R 10 or R 11 is a group represented by the general formula (13).
  • One aspect of the compound according to this embodiment is a compound represented by the following general formula (1A), (1B), (1C) or (1D).
  • the compound represented by the following general formula (1A) has the same meaning as the compound represented by the above-mentioned general formula (1A).
  • Ar 1 has the same meaning as Ar 1 in formula (1)
  • R 1 to R 15 each independently have the same definition as R 1 to R 15 in formula (1)
  • Y1 and R16 to R19 each independently have the same definition as Y1 and R16 to R19 in formula (14).
  • R 1 to R 19 is a group represented by the general formula (13)
  • R 1 to R 4 , R 6 to R 11 and R 16 to R 18 is a group represented by the general formula (13)
  • R 10 , R 11 , R 16 or R 18 is a group represented by the general formula (13)
  • R 10 or R 11 is a group represented by the general formula (13).
  • One aspect of the compound according to this embodiment is a compound represented by any one of the following general formulas (2A), (2B), (2C), (2D), (2E), and (2F).
  • Ar 1 has the same meaning as Ar 1 in the general formula (1)
  • R 1 to R 15 each independently have the same meaning as R 1 to R 15 in the general formula (1)
  • Y 1 and R 16 to R 19 each independently have the same meaning as Y 1 and R 16 to R 19 in the general formula (14).
  • two Y 1 are the same or different from each other
  • two R 16 are the same or different from each other
  • two R 17 are the same or different from each other
  • two R 18 are the same or different from each other
  • two R 19 are the same or different from each other.
  • R 1 to R 19 is a group represented by the general formula (13)
  • R 1 to R 4 , R 6 to R 11 and R 16 to R 18 is a group represented by the general formula (13)
  • R 10 , R 11 , R 16 or R 18 is a group represented by the general formula (13)
  • R 10 or R 11 is a group represented by the general formula (13).
  • R 31 to R 39 are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, and even more preferably a hydrogen atom.
  • at least one of R 31 to R 39 may be a deuterium atom.
  • R 21 to R 30 are each independently a hydrogen atom, a group represented by the general formula (13) above, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, a group represented by -Si(R 41 )(R 42 )(R 43 ), or a group represented by -Ge(R 44 )(R 45 )(R 46 ).
  • at least one of R 21 to R 30 may be a deuterium atom.
  • R 1 to R 19 are each independently a hydrogen atom, a group represented by the general formula (13) above, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, a group represented by -Si(R 41 )(R 42 )(R 43 ), or a group represented by -Ge(R 44 )(R 45 )(R 46 ).
  • at least one of R 1 to R 19 may be a deuterium atom. It is preferable that one of R 1 to R 19 is a group represented by the general formula (13).
  • Ar 1 is a substituted or unsubstituted phenyl group;
  • R 21 to R 23 and R 25 each independently have the same definition as R 21 to R 23 and R 25 in the general formula (11),
  • Each Rx independently has the same meaning as Rx in general formula (1X), * indicates the bonding position of the nitrogen atom to which Ar 1 in the general formula (1) is bonded.
  • X 1 has the same meaning as X 1 in the general formula (12)
  • R 26 to R 30 each independently have the same meaning as R 26 to R 30 in the general formula (12)
  • a plurality of R 30 are the same or different from each other
  • Rx each independently has the same meaning as Rx in the general formula (1X), and a plurality of Rx's are the same or different. * indicates the bonding position of the nitrogen atom to which Ar 1 in the general formula (1) is bonded.
  • Ar 1 is not a substituted or unsubstituted naphthylene group.
  • one or more pairs of adjacent two or more of R 21 to R 25 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • one or more pairs of adjacent two or more of R 26 to R 29 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • one or more pairs of adjacent two or more R 30 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • X 1 is preferably an oxygen atom or a sulfur atom.
  • R 21 to R 23 , R 25 , R 26 to R 30 and Rx are each preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, a group represented by -Si(R 41 )(R 42 )(R 43 ), or a group represented by -Ge(R 44 )(R 45 )(R 46 ).
  • the pair consisting of R 51 and R 52 are not bonded to each other, and it is also preferable that the pair consisting of R 53 and R 54 are not bonded to each other.
  • examples of the cycloalkyl group having 3 to 20 ring carbon atoms include groups in which one hydrogen atom has been removed from a monocycloalkane (e.g., cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc.) and a polycycloalkane (e.g., adamantane, norbornane, isobornane, tricyclodecane, tetracyclododecane, etc.).
  • a monocycloalkane e.g., cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc.
  • a polycycloalkane e.g., adamantane, norbornane, isobornane, tricyclodecane, tetracyclododecane, etc.
  • the substituent in the case of "substituted or unsubstituted” is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.
  • the group represented by --Ge( R.sup.44 )( R.sup.45 )( R.sup.46 ) is a substituted germanium group when R.sup.44 , R.sup.45 and R.sup.46 are substituents.
  • the compound according to this embodiment is preferably a material used in the light-emitting layer.
  • the compound according to this embodiment is preferably a host material.
  • the compound according to this embodiment (the compound represented by general formula (1)) can be produced according to the synthesis method described in the Examples described later, or by following the synthesis method and using known alternative reactions and raw materials suited to the target product.
  • Specific examples of the compound according to this embodiment include the following compounds, however, the present invention is not limited to these specific examples.
  • the material for organic electroluminescence devices according to this embodiment contains the compound according to the first embodiment.
  • One aspect of the material for organic electroluminescence devices includes only the compound according to the first embodiment, and another aspect of the material for organic electroluminescence devices includes the compound according to the first embodiment and another compound different from the compound in the first embodiment.
  • One embodiment of the material for an organic electroluminescence device contains the compound according to the first embodiment as a host material and other compounds such as a sensitizing material (preferably a delayed fluorescent compound).
  • a sensitizing material preferably a delayed fluorescent compound
  • One embodiment of the material for an organic electroluminescence device includes the compound according to the first embodiment as a host material, a sensitizing material (preferably a delayed fluorescent compound), and a fluorescent material.
  • the organic EL element according to the third embodiment includes an organic layer between an anode and a cathode.
  • the organic layer includes at least one layer made of an organic compound.
  • the organic layer includes a plurality of layers made of an organic compound stacked together.
  • the organic layer may further include an inorganic compound.
  • the organic EL device includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode, the emitting layer containing a host material, a sensitizing material, and a fluorescent material.
  • the host material is the compound according to the first embodiment.
  • the host material, the sensitizing material, and the fluorescent material are different compounds.
  • the sensitizing material In the light-emitting layer, recombination of holes and electrons is likely to occur on the molecules of the host material or sensitizing material, not on the fluorescent material, and in the sensitizing material, when the sensitizing material is a delayed fluorescent compound, it is considered that reverse intersystem crossing occurs from the lowest excited triplet state to the lowest excited singlet state. In this way, it is considered that after efficient transition of the energy state to the lowest excited singlet state occurs in the sensitizing material, energy transfer occurs from the sensitizing material to the fluorescent material, and fluorescence is emitted from the lowest excited singlet state of the fluorescent material.
  • the compound according to the first embodiment (compound represented by general formula (1)) used as the host material has a sterically bulky substituent, and thus can reduce energy loss due to interaction with the dopant compound. As a result, it is considered that the fluorescent material that receives energy from the sensitizing material emits light with high efficiency.
  • the organic layer may be, for example, composed of one light-emitting layer, or may include a layer that can be used in an organic EL element.
  • the layer that can be used in an organic EL element is not particularly limited, but may be, for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • a hole transport layer may be disposed between the anode and the light-emitting layer.
  • an electron transport layer may be disposed between the cathode and the light-emitting layer.
  • FIG. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment.
  • the organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
  • the organic layer 10 is configured by laminating a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side.
  • the present invention is not limited to the configuration of the organic EL element shown in FIG.
  • the host material, the sensitizing material, and the fluorescent material are contained in a single layer.
  • the host material, the sensitizing material, and the fluorescent material are contained in the single light-emitting layer
  • the organic EL element has multiple light-emitting layers
  • the host material, the sensitizing material, and the fluorescent material are contained in any one of the multiple light-emitting layers.
  • the light-emitting layer when the light-emitting layer contains a delayed fluorescent compound as a sensitizing material, the light-emitting layer does not contain a phosphorescent metal complex.
  • the host material is the compound according to the first embodiment.
  • the compound used as the host material may be referred to as the first compound.
  • the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescent compounds.
  • the compound used as the sensitizing material may be referred to as the second compound.
  • the sensitizing material is a delayed fluorescent compound.
  • the delayed fluorescent compound is not a phosphorescent metal complex. In this embodiment, it is preferable that the delayed fluorescent compound is not a metal complex.
  • the delayed fluorescent compound is not a phosphorescent metal complex. In this embodiment, it is preferable that the delayed fluorescent compound is not a metal complex.
  • the delayed fluorescent compound is preferably a compound represented by the following general formula (H1):
  • AH is a group having at least one partial structure selected from the group consisting of the following general formulae (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7), and (a-8), D H is a group represented by the following general formula (221), (222) or (223):
  • LH is Single bond, a substituted or unsubstituted aryl ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms,
  • m is 1, 2, 3, 4 or 5, and the multiple AH are the same or different from each other;
  • n is 1, 2, 3, 4 or 5, and the multiple D H are the same or different.
  • r is 0, 2 or 4;
  • a group consisting of a plurality of R29 is joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • XA represents a sulfur atom, an oxygen atom, or C(R 291 )(R 292 );
  • the pair consisting of R 291 and R 292 is joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • R 29 , R 291 and R 292 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring are each independently Hydrogen atoms, a substituted or unsubstituted
  • 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 atoms, a 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When a plurality of R 901 are present, the plurality of R 901 are the same or different, When a plurality of R 902 are present, the plurality of R 902 are the same or different from each other, When a plurality of R 901 are
  • the delayed fluorescent compound is preferably a compound represented by the following general formula (H10):
  • CN is a cyano group
  • LH is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms
  • D 11 and D 12 each independently represent a group represented by the general formula (221), (222) or (223); m is 1, 2, 3, 4 or 5; nx is 0, 1, 2, 3, 4 or 5; ny is 0, 1, 2, 3, 4 or 5; nx + ny is 1, 2, 3, 4 or 5; D 11 and D 12 are the same or different from each other; A plurality of D 11 are the same or different from each other, Multiple D12 are the same or different from each other.
  • the delayed fluorescent compound is preferably a compound represented by the following general formula (H100):
  • L H , D 11 , D 12 , m, nx and ny are respectively defined as L H , D 11 , D 12 , m, nx and ny in the general formula (H10),
  • Each R is independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a 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
  • the delayed fluorescent compound is preferably a compound represented by the following general formula (H101):
  • D11 and D12 are the same as D11 and D12 in general formula (H10), respectively.
  • the delayed fluorescent compound is preferably a compound represented by the following general formula (H110), (H120) or (H130).
  • D11 and D12 are the same as D11 and D12 in general formula (H10), respectively.
  • the group represented by the general formula (222) in the delayed fluorescent compound is preferably any group selected from the group consisting of groups represented by the following general formulae (22A), (22B), (22C), (22D), (22E), and (22F).
  • R 221 to R 228 are the same as R 221 to R 228 in the general formula (222), respectively.
  • R 229 and R 230 each independently have the same meaning as R 29 in formula (224)
  • XA has the same meaning as XA in the general formula (225)
  • * indicates a bonding position.
  • the delayed fluorescent compound is a compound represented by general formula (H101)
  • the * in general formulas (22A), (22B), (22C), (22D), (22E) and (22F) is bonded to the benzene ring itself explicitly shown in general formula (H101).
  • X 1 A is also preferably a sulfur atom or an oxygen atom.
  • R 291 and R 292 are each independently a hydrogen atom, a 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • any pair of adjacent two or more of R 21 to R 28 are not bonded to each other.
  • any pair of adjacent two or more of R 221 to R 228 are not bonded to each other.
  • any pair of adjacent two or more of R 231 to R 238 are not bonded to each other.
  • each R is preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • each R is preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
  • R 21 to R 28 , R 221 to R 228 , R 231 to R 238 and R 29 are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • R 21 to R 28 , R 221 to R 228 , R 231 to R 238 and R 29 are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
  • R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms
  • R 21 to R 28 , R 221 to R 228 , R 231 to R 238 and R 29 are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms
  • R 21 to R 28 , R 221 to R 228 , R 231 to R 238 and R 29 are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
  • the substituent in the case of "substituted or unsubstituted” is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.
  • the substituent in the case of "substituted or unsubstituted” is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.
  • R 904 when R 904 is a hydrogen atom, the group represented by —O—(R 904 ) is a hydroxy group.
  • the group represented by -S-(R 905 ) is a thiol group when R 905 is a hydrogen atom.
  • the group represented by --Ge(R 933 )(R 934 )(R 935 ) is a substituted germanium group when R 933 , R 934 and R 935 are substituents.
  • R 936 and R 937 when R 936 and R 937 are substituents, the group represented by -B(R 936 )(R 937 ) is a substituted boryl group.
  • thermally activated delayed fluorescence may be referred to as delayed fluorescence.
  • Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In this document, it is explained that if the energy difference ⁇ E 13 between the excited singlet state and the excited triplet state of a fluorescent material can be reduced, reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state occurs with high efficiency, and thermally activated delayed fluorescence (TADF) is expressed. Furthermore, in Figure 10.38 in this document, the mechanism of delayed fluorescence generation is explained.
  • the TADF mechanism is a mechanism that utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference ( ⁇ ST) between the singlet level and the triplet level is used.
  • TADF compounds include compounds in which a donor site and an acceptor site are bound within the molecule.
  • delayed fluorescence emission can be confirmed by transient PL (photoluminescence) measurement.
  • Transient PL measurement is a method of irradiating a sample with a pulsed laser to excite it, and measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped.
  • PL emission in TADF compounds is classified into emission components from singlet excitons generated by the first PL excitation and emission components from singlet excitons generated via triplet excitons.
  • the lifetime of singlet excitons generated by the first PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from the singlet excitons decays quickly after irradiation with a pulsed laser.
  • delayed fluorescence is emitted from singlet excitons generated via triplet excitons, which have a long life span, and therefore decays slowly.
  • the emission intensity derived from delayed fluorescence can be obtained.
  • Figure 2 shows a schematic diagram of an exemplary device for measuring transient PL. We will explain a method for measuring transient PL using Figure 2 and an example of behavior analysis of delayed fluorescence.
  • the transient PL measurement device 100 in FIG. 2 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image.
  • a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength
  • a sample chamber 102 for accommodating a measurement sample
  • a spectroscope 103 for dispersing the light emitted from the measurement sample
  • a streak camera 104 for forming a two-dimensional image
  • personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in FIG. 2.
  • the sample contained in the sample chamber 102 is obtained by forming a thin film of a matrix material doped with a doping material at a concentration of 12% by mass on a quartz substrate.
  • a pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed in the sample chamber 102 to excite the doping material.
  • Emission light is extracted in a direction at 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by the spectroscope 103, and a two-dimensional image is formed in the streak camera 104.
  • a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity.
  • By cutting out this two-dimensional image on a specified time axis it is possible to obtain an emission spectrum in which the vertical axis is emission intensity and the horizontal axis is wavelength.
  • a decay curve (transient PL) in which the vertical axis is the logarithm of emission intensity and the horizontal axis is time.
  • the following compound HX1 was used as the matrix material, and the following compound DX1 was used as the doping material to prepare thin film sample A as described above, and transient PL measurements were performed.
  • Thin film sample B was prepared as described above using the following compound HX2 as the matrix material and the aforementioned compound DX1 as the doping material.
  • Figure 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.
  • transient PL measurement it is possible to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, it is possible to estimate the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state.
  • the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly is relatively large.
  • Prompt emission is emission that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength that the delayed fluorescent material absorbs.
  • Delay emission is emission that is not observed immediately after excitation by the pulsed light, but is observed at a later time.
  • the amount and ratio of Prompt and Delay luminescence can be calculated by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of Prompt and Delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2.
  • a sample prepared by the following method is used to measure the delayed fluorescence of the delayed fluorescent compound according to this embodiment.
  • the delayed fluorescent compound according to this embodiment is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption.
  • the sample solution is frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.
  • the fluorescence spectrum of the sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions.
  • the total fluorescence quantum yield is calculated using the fluorescence area intensities of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.
  • the amount of prompt luminescence (immediate luminescence) of the compound to be measured is XP and the amount of delay luminescence (delayed luminescence) is XD , it is preferable that the value of XD / XP is 0.05 or more.
  • the amounts and ratio of prompt luminescence and delay luminescence of compounds other than the delayed fluorescent compound in this specification are measured in the same manner as the amounts and ratio of prompt luminescence and delay luminescence of the delayed fluorescent compound according to this embodiment.
  • the difference ⁇ ST(GT2) between the lowest excited singlet energy S 1 (GT2) of the delayed fluorescent compound and the energy gap T 77K (GT2) at 77 [K] of the delayed fluorescent compound is preferably less than 0.5 eV, more preferably less than 0.3 eV, even more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.05 eV. That is, it is preferable that ⁇ ST(GT2) satisfies the relationship of the following formula (Math 2), (Math 2A), (Math 2B), (Math 2C) or (Math 2D).
  • the energy gap at 77 K differs from the triplet energy that is usually defined.
  • the triplet energy is measured as follows. First, a sample is prepared by dissolving a compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube.
  • the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77 [K]), a tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated from a predetermined conversion formula based on the wavelength value at the intersection of the tangent and the horizontal axis.
  • the thermally activated delayed fluorescent compound is preferably a compound with a small ⁇ ST. If ⁇ ST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), and the excited singlet state and the excited triplet state are mixed.
  • the measurement method is the same as that of the normal triplet energy T, but in order to distinguish that it is different in the strict sense, the value measured as follows is referred to as the energy gap T 77K .
  • a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at low temperature (77 [K]), a tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the energy amount calculated from the following conversion formula (F1) based on the wavelength value ⁇ edge [nm] of the intersection point between the tangent and the horizontal axis is defined as the energy gap T 77K at 77 [K].
  • Conversion formula (F1): T 77K [eV] 1239.85/ ⁇ edge
  • the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows.
  • the slope of this tangent increases as the curve rises (i.e., as the vertical axis increases).
  • the tangent drawn at the point where this slope is at its maximum is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side described above, and a tangent drawn at a point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is regarded as a tangent to the rising edge on the short wavelength side of the phosphorescence spectrum.
  • Phosphorescence can be measured using a spectrofluorophotometer body, Model F-4500, manufactured by Hitachi High-Technologies Corp.
  • the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.
  • the method for measuring the lowest excited singlet energy S1 using a solution includes the following method.
  • a 10 ⁇ mol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300 K).
  • a tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value ⁇ edge [nm] at the intersection of the tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the minimum excited singlet energy.
  • Conversion formula (F2): S 1 [eV] 1239.85/ ⁇ edge
  • An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.
  • the tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows.
  • the slope of this tangent decreases and then increases repeatedly.
  • the tangent drawn at the point where the slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values of 0.2 or less are not included in the maximum values on the longest wavelength side.
  • the delayed fluorescent compound can be produced by a known method.
  • the delayed fluorescent compound can also be produced by following a known method and using known alternative reactions and raw materials suited to the target product.
  • Specific examples of the delayed fluorescent compound include the following compounds, however, the present invention is not limited to these specific examples.
  • the fluorescent material is preferably a compound that does not exhibit thermally activated delayed fluorescence.
  • the fluorescent material is not a phosphorescent metal complex.
  • the fluorescent material is preferably not a metal complex.
  • the fluorescent material is one or more compounds selected from the group consisting of third compounds represented by the following general formula (41):
  • Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms
  • L 401 and L 402 each independently represent O, S, Se, NR 40 , C(R 41 )(R 42 ), or Si(R 43 )(R 44 );
  • R 40 to R 44 each independently represent by combining with the ring a, ring b or ring c to form a substituted or unsubstituted monocycle, or is not bonded to the ring a, ring b, or ring c, to form a substituted or unsubstituted fused ring;
  • R 41 and R 42 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form
  • the compound represented by the general formula (41) is preferably a compound represented by the following general formula (410):
  • Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms
  • R 401 and R 402 each independently represent by combining with the ring a, ring b or ring c to form a substituted or unsubstituted monocycle, or is not bonded to the ring a, ring b, or ring c, to form a substituted or unsubstituted fused ring
  • R 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon
  • the compound represented by the general formula (41) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (41-1) to (41-6):
  • Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 402 and R 424 , a pair of two or more adjacent pairs of R 424 to R 427 , a pair of R 427 and R 412 , and a pair of R 412 and R 411 , joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, R 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent
  • Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 402 and R 424 , a pair of two or more adjacent pairs of R 424 to R 427 , a pair of R 413 and R 414 , and a pair of R 414 and R 401 , joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, R 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent
  • Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 415 and R 416 , a pair of R 416 and R 412 , and a pair of R 412 and R 411 , joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, R 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent a substituted or unsubstituted alkyl
  • Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 402 and R 418 , a pair of R 418 and R 417 , and a pair of R 412 and R 411 , joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, R 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring are each independently a substituted or unsubstituted alkyl
  • Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 402 and R 418 , a pair of R 418 and R 417 , a pair of R 413 and R 414 , and a pair of R 414 and R 401 , joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, R 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent
  • one or more pairs selected from the group consisting of a pair of R 412 and R 411 , a pair of R 413 and R 414, a pair of R 415 and R 416 , and a pair of R 417 and R 418 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring.
  • the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (41-7):
  • Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 402 and R 424 , a pair of two or more adjacent pairs of R 424 to R 427 , and a pair of two or more adjacent pairs of R 437 to R 440 , joined together to form a substituted or unsubstituted monocyclic ring, or are bonded together to form a substituted or unsubstituted fused ring, or are not bonded together, R 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent a substituted or unsubstituted
  • R 401 and R 402 are each independently preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and further preferably a group represented by the following general formula (42).
  • R 432 to R 436 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently a hydrogen atom or a substituent R X , and the substituent R X has the same meaning as the substituent R X in formula (41-1),
  • R X has the same meaning as the substituent R X in formula (41-1)
  • the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-1):
  • R 421 to R 431 are the same as R 421 to R 431 in the general formula (41-6), respectively.
  • One or more pairs of adjacent two or more of R 451 to R 455 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded together to form a substituted or unsubstituted fused ring, or are not bonded together
  • One or more pairs of adjacent two or more of R 456 to R 460 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded together to form a substituted or unsubstituted fused ring, or are not bonded together
  • R 451 to R 455 and R 456 to R 460 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted condensed ring, are each independently a hydrogen atom or a substituent R X , and the substituent R X has the same meaning
  • the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-2):
  • R 422 , R 426 , R 429 , R 453 , and R 458 each independently represent a hydrogen atom or a substituent R X , which has the same meaning as the substituent R X in the general formula (41-1).
  • the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-3):
  • R 421 to R 427 , R 437 to R 440 and Xa are respectively defined as R 421 to R 427 , R 437 to R 440 and Xa in the general formula (41-7),
  • One or more pairs of adjacent two or more of R 451 to R 455 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded together to form a substituted or unsubstituted fused ring, or are not bonded together
  • One or more pairs of adjacent two or more of R 456 to R 460 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded together to form a substituted or unsubstituted fused ring, or are not bonded together
  • R 451 to R 455 and R 456 to R 460 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted condensed ring, are each independently
  • the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-4):
  • Xa has the same meaning as Xa in the general formula (41-7)
  • R 422 , R 426 , R 429 , R 439 , R 453 , and R 458 each independently represent a hydrogen atom or a substituent R X
  • the substituent R X has the same meaning as the substituent R X in the general formula (41-1).
  • R 422 , R 426 , R 429 , R 439 , R 453 , and R 458 in the third compound are each independently preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and even more preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
  • Xa and Xb in the third compound are each independently O or S.
  • the compound represented by the general formula (41) can be produced by a known method.
  • the compound represented by the general formula (41) can also be produced by following a known method and using known alternative reactions and raw materials suited to the target product.
  • Specific examples of compounds represented by formula (41) include the compounds shown below. In the specific examples, Me represents a methyl group, tBu represents a tertiary butyl group, and Ph represents a phenyl group.
  • the substituent in the case of "substituted or unsubstituted" in each of the general formulas is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901a )(R 902a )(R 903a ), -O-(R 904a ), -S-(R 905a ), -N(R 906a )(R 907a ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms; R 901a to
  • the substituent in the "substituted or unsubstituted" cases in each of the general formulas above is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the "substituted or unsubstituted" cases in each of the general formulas above is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.
  • the maximum peak wavelength of the third compound as the fluorescent material is preferably 480 nm or less, and more preferably 475 nm or less.
  • the maximum peak wavelength of the third compound as the fluorescent material is preferably 430 nm or more, and more preferably 440 nm or more.
  • the maximum peak wavelength of fluorescent emission may be referred to as the maximum peak wavelength of fluorescent emission.
  • the first compound preferably emits blue light.
  • blue light emission refers to light emission having a maximum peak wavelength in the fluorescent spectrum in the range of 430 nm to 480 nm.
  • the emission spectrum half width FWHM of the third compound as the fluorescent material is preferably 40 nm or less, and more preferably 30 nm or less. In this embodiment, the emission spectrum half width FWHM of the third compound as the fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. FWHM is an abbreviation for full width at half maximum.
  • the maximum fluorescence emission peak wavelength refers to the maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound to be measured is dissolved at a concentration of 10 ⁇ 6 mol/L or more and 10 ⁇ 5 mol/L or less.
  • the emission spectrum half width FWHM is the full width at half maximum at the maximum peak of the fluorescence spectrum.
  • a fluorescence spectrum measuring device can be used as a device for measuring the fluorescence spectrum.
  • a fluorescence spectrum measuring device (device name: FP-8300) manufactured by JASCO Corporation can be used. Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.
  • the Stokes shift of the third compound as the fluorescent material is preferably 25 nm or less, and more preferably 20 nm or less.
  • the Stokes shift of the third compound as a fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more.
  • the excitation energy can be reduced.
  • the third compound has a Stokes shift of 10 nm or more, self-absorption can be suppressed and loss of efficiency can be reduced.
  • the Stokes shift can be measured by the following method. The compound to be measured is dissolved in toluene at a concentration of 2.0 ⁇ 10 ⁇ 5 mol/L to prepare a measurement sample.
  • the measurement sample placed in a quartz cell is irradiated with continuous light in the ultraviolet-visible region at room temperature (300K) to measure the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength).
  • a spectrophotometer can be used to measure the absorption spectrum, for example, a spectrophotometer U-3900/3900H model from Hitachi High-Tech Science Corporation can be used.
  • the compound to be measured is dissolved in toluene at a concentration of 4.9 ⁇ 10 ⁇ 6 mol/L to prepare a measurement sample.
  • the measurement sample placed in a quartz cell is irradiated with excitation light at room temperature (300K) to measure the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength).
  • a spectrophotometer can be used to measure the fluorescence spectrum, for example, a spectrofluorometer F-7000 model from Hitachi High-Tech Science Corporation can be used. From these absorption and fluorescence spectra, the difference between the maximum absorption wavelength and the maximum fluorescence wavelength is calculated to determine the Stokes shift (SS), which is expressed in nm.
  • SS Stokes shift
  • the sensitizing material is the delayed fluorescent compound.
  • the light-emitting layer contains a delayed fluorescent compound as a sensitizing material, and may not contain a phosphorescent metal complex.
  • FIG. 4 is a diagram showing an example of the relationship between the energy levels of the host material (first compound), the delayed fluorescent compound (second compound) as a sensitizing material, and the fluorescent material (third compound) in the light-emitting layer.
  • S0 represents the ground state.
  • S1 (M1) represents the lowest excited singlet state of the host material
  • T1 (M1) represents the lowest excited triplet state of the host material.
  • S1 (M2) represents the lowest excited singlet state of the delayed fluorescent compound
  • T1 (M2) represents the lowest excited triplet state of the delayed fluorescent compound.
  • S1 (M3) represents the lowest excited singlet state of the fluorescent material
  • T1 (M3) represents the lowest excited triplet state of the fluorescent material.
  • the minimum excited singlet energy S 1 (GT2) of the delayed fluorescent compound and the minimum excited singlet energy S 1 (D) of the fluorescent material satisfy the relationship of the following mathematical formula (Mathematical Formula 4).
  • the lowest excited singlet energy S 1 (H1) of the host material and the lowest excited singlet energy S 1 (GT2) of the delayed fluorescent compound satisfy the relationship of the following mathematical formula (Mathematical Formula 4A).
  • the above formula (Formula 1) is expressed by the following formula (Formula 6).
  • the energy gap T 77K (GT2) at 77 [K] of the delayed fluorescent compound and the energy gap T 77K (D) at 77 [K] of the fluorescent material satisfy the relationship of the following mathematical formula (Mathematical Formula 6A).
  • the energy gaps T 77K at 77 [K] of the host material, the delayed fluorescent compound, and the fluorescent material satisfy the relationship of the following formula (Mathematical Formula 6B).
  • the fluorescent compound is the main emitter in the light-emitting layer.
  • the maximum peak wavelength of the light emitted from the organic EL element is measured as follows. A voltage is applied to the organic EL element so that the current density becomes 10 mA/cm 2 , and the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).
  • the contents of the host material (first compound), the sensitizing material (second compound), and the fluorescent material (third compound) contained in the light-emitting layer are preferably within the following ranges, for example.
  • the content of the host material (first compound) in the light-emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more.
  • the content of the host material (first compound) in the light-emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.
  • the content of the delayed fluorescent compound in the light-emitting layer is preferably 5% by mass or more, and more preferably 10% by mass or more.
  • the content of the delayed fluorescent compound in the light-emitting layer is preferably 50% by mass or less, and more preferably 30% by mass or less.
  • the content of the fluorescent material (third compound) in the light-emitting layer is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
  • the content of the fluorescent material (third compound) in the light-emitting layer is preferably 10% by mass or less, and more preferably 5% by mass or less.
  • the upper limit of the total content of the host material (first compound), the sensitizing material (second compound), and the fluorescent material (third compound) in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the light-emitting layer containing materials other than the host material, the sensitizing material, and the fluorescent material. In this embodiment, the light-emitting layer may contain only one type of host material, or may contain two or more types of host materials.
  • the thickness of the light-emitting layer in the organic EL element of this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less.
  • the thickness is 5 nm or more, the formation of the light-emitting layer and the adjustment of the chromaticity tend to be easy, and when the thickness is 50 nm or less, an increase in the driving voltage is easily suppressed.
  • the substrate is used as a support for the organic EL element.
  • glass, quartz, plastic, etc. can be used as the substrate.
  • a flexible substrate may also be used.
  • a flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate.
  • An inorganic deposition film may also be used.
  • indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% by mass of zinc oxide added to indium oxide.
  • indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% by mass of tungsten oxide and 0.1% to 1% by mass of zinc oxide relative to indium oxide.
  • it may be formed by vacuum deposition, coating, inkjet, spin coating, etc.
  • the hole injection layer formed on the anode which is one of the EL layers formed on the anode, is made of a composite material that allows easy hole injection regardless of the work function of the anode, so any material that can be used as an electrode material (e.g., metals, alloys, electrically conductive compounds, and mixtures of these, including other elements belonging to Groups 1 or 2 of the periodic table) can be used.
  • an electrode material e.g., metals, alloys, electrically conductive compounds, and mixtures of these, including other elements belonging to Groups 1 or 2 of the periodic table
  • Materials with small work functions such as elements belonging to Group 1 or 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • alloys containing these for example, MgAg, AlLi
  • rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • vacuum deposition and sputtering methods can be used.
  • silver paste coating and inkjet methods can be used.
  • the anode is preferably formed of a metal material that is optically transparent or semi-transparent, and transmits light from the light-emitting layer.
  • optically transparent or semi-transparent means a property that transmits 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer.
  • the optically transparent or semi-transparent metal material can be appropriately selected from the materials listed in the anode section above.
  • the anode is a reflective electrode having a reflective layer.
  • the reflective layer is preferably formed of a metal material having light reflectivity.
  • light reflectivity means a property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light emitting layer.
  • the metal material having light reflectivity can be appropriately selected from the materials listed in the above section on the anode.
  • the anode may be composed of only a reflective layer, but may also have a multi-layer structure having a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is disposed between the reflective layer and the hole transport zone.
  • the conductive layer can be appropriately selected from the materials listed in the above section on the anode.
  • cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a small work function (specifically, 3.8 eV or less).
  • a cathode material include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such
  • a vacuum deposition method or a sputtering method can be used.
  • a coating method or an inkjet method can be used.
  • the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function.
  • conductive materials can be deposited using a sputtering method, inkjet method, spin coating method, etc.
  • the cathode is a reflective electrode.
  • the reflective electrode is preferably formed from a metal material having optical reflectivity.
  • the metal material having optical reflectivity can be appropriately selected from the materials listed in the cathode section.
  • the cathode is preferably formed from a metal material that is optically transparent or semi-transparent and transmits light from the light-emitting layer.
  • the optically transparent or semi-transparent metal material can be appropriately selected from the materials listed in the cathode section above.
  • the organic EL element according to this embodiment may be a bottom-emission type organic EL element, or a top-emission type organic EL element.
  • the organic EL element is of a bottom emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflection.
  • the organic EL element is of a top emission type, it is preferable that the anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmittance.
  • the organic EL device When the organic EL device is of a top-emission type, the organic EL device usually includes a capping layer on the top of the cathode.
  • the capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide).
  • the capping layer may contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives.
  • a laminate in which layers containing these substances are laminated can also be used as the capping layer.
  • the hole injection layer is a layer containing a substance having a high hole injection property, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or the like.
  • a substance having a high hole injection property such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or the like.
  • examples of the material with high hole injection properties include low molecular weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N- ⁇ 4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl ⁇ -N-phenylamino)biphenyl (abbreviation: DNTPD), 1,
  • aromatic amine compounds include 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation:
  • a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used.
  • polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino ⁇ phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]
  • a polymer compound to which an acid is added such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) or polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can also be used.
  • PEDOT/PSS poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid)
  • PAni/PSS polyaniline/poly(styrenesulfonic acid)
  • the hole transport layer is a layer containing a substance with high hole transport properties.
  • an aromatic amine compound a carbazole derivative, an anthracene derivative, or the like can be used.
  • NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • TPD N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine
  • TPD N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine
  • BAFLP 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine
  • BAFLP 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]bipheny
  • aromatic amine compounds examples include aromatic amine compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB).
  • TDATA 4,4',4''-tris(N,N-diphenylamino)triphenylamine
  • MTDATA 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine
  • BSPB 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyla
  • the hole transport layer may be made of a carbazole derivative such as CBP, CzPA, or PCzPA, or an anthracene derivative such as t-BuDNA, DNA, or DPAnth.
  • a carbazole derivative such as CBP, CzPA, or PCzPA
  • an anthracene derivative such as t-BuDNA, DNA, or DPAnth.
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • other substances may be used as long as they have a higher hole transporting property than an electron transporting property.
  • the layer containing the substance having a high hole transporting property may be a single layer or a layer in which two or more layers made of the above-menti
  • the electron transport layer is a layer containing a substance with high electron transport properties.
  • a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex
  • a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound can be used.
  • a metal complex such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), BAlq, Znq, ZnPBO, or ZnBTZ can be used.
  • the substances described here are mainly substances having an electron mobility of 10 -6 cm 2 /Vs or more. Note that substances other than the above may be used as the electron transport layer as long as they have a higher electron transport property than a hole transport property.
  • the electron transport layer may be a single layer or a layer in which two or more layers made of the above substances are stacked.
  • the electron transport layer may also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).
  • PF-Py poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)]
  • PF-BPy poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)]
  • the electron injection layer is a layer containing a substance with high electron injection properties.
  • alkali metals, alkaline earth metals, or compounds thereof such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), etc.
  • a substance having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) in Alq, etc. can be used. In this case, electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer.
  • a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor.
  • the organic compound is preferably a material that is excellent in transporting the generated electrons, and specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used.
  • the electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples of such substances include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferred, and examples of such substances include lithium oxide, calcium oxide, and barium oxide.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.
  • each layer of the organic EL element is not limited to those specifically mentioned above, but may be any known method, such as a dry film formation method, such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method, such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.
  • a dry film formation method such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method
  • a wet film formation method such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.
  • each organic layer of the organic EL element is not limited unless otherwise specified above. In general, if the thickness is too thin, defects such as pinholes are likely to occur, and if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the thickness of each organic layer of the organic EL element is usually preferably in the range of several nm to 1 ⁇ m.
  • the organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • the organic EL element according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • the electronic device is equipped with one or more organic EL elements selected from the group consisting of the organic EL elements according to the above-described embodiments and the organic EL elements according to other embodiments described below.
  • Examples of the electronic device include display devices and light-emitting devices.
  • Examples of the display device include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers.
  • Examples of the light-emitting device include lighting and vehicle lamps.
  • the light-emitting device can be used in a display device, and can also be used, for example, as a backlight for a display device.
  • the display device as the electronic device according to this embodiment is preferably an organic EL display device equipped with organic EL elements as red, green, and blue pixels.
  • the blue pixel is preferably an organic EL element according to the third embodiment.
  • An organic EL device includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode.
  • the emitting layer may include a compound according to the first embodiment as a host material and a phosphorescent metal complex as a dopant material.
  • An organic EL element includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode.
  • the emitting layer may include a compound according to the first embodiment as a host material, a phosphorescent metal complex as a sensitizing material, and a fluorescent material (a third compound) as a dopant material.
  • the organic EL element according to the other embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be laminated.
  • the organic EL element has multiple light-emitting layers, at least one of the light-emitting layers may satisfy the conditions described in the above embodiment.
  • the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission due to electronic transition from a triplet excited state directly to a ground state.
  • the organic EL element has a plurality of light-emitting layers
  • these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.
  • a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer.
  • the blocking layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons.
  • the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) on the cathode side of the blocking layer.
  • the organic EL element includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer.
  • the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) on the anode side of the blocking layer.
  • a layer e.g., a hole transport layer
  • the organic EL element includes a hole transport layer
  • a barrier layer may be provided adjacent to the light-emitting layer to prevent the excitation energy from leaking from the light-emitting layer to the surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers on the electrode side of the barrier layer (e.g., the electron transport layer and the hole transport layer, etc.).
  • An organic EL device includes an anode, a cathode, an emitting layer disposed between the anode and the cathode, and an electron blocking layer between the anode and the emitting layer, and the electron blocking layer may include the compound according to the first embodiment (the compound represented by the general formula (1)).
  • the electron blocking layer is preferably in direct contact with the emitting layer.
  • the electron blocking layer is preferably disposed between the hole transport layer and the emitting layer.
  • the hole blocking layer is preferably disposed between the electron transport layer and the emitting layer.
  • the organic EL element according to an embodiment may be an organic EL element including, instead of the organic layer 10 in FIG. 1 , an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer stacked in this order from the anode side.
  • the specific structure and shape in implementing the present invention may be other structures, etc., as long as the object of the present invention can be achieved.
  • Example 1 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm ⁇ 75 mm ⁇ 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130 nm.
  • the glass substrate with the transparent electrode lines after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compounds HT-1 and HA-1 were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm.
  • the proportion of the compound HT-1 in the hole injection layer was 97% by mass, and the proportion of the compound HA-1 was 3% by mass.
  • the compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm.
  • the compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm.
  • a compound EBL-1 was evaporated on the second hole-transporting layer to form a third hole-transporting layer (also referred to as an electron blocking layer) having a thickness of 5 nm.
  • the compound Host-1 as a host material (first compound), the compound STZ-1 as a sensitizing material (second compound), and the compound BD-1 as a fluorescent material (third compound) were co-deposited to form an emission layer having a thickness of 30 nm.
  • the proportion of the compound Host-1 in the emission layer was 74% by mass
  • the proportion of the compound STZ-1 was 25% by mass
  • the proportion of the compound BD-1 was 1% by mass.
  • compound HBL-1 was deposited on the light-emitting layer to form a hole blocking layer having a thickness of 10 nm.
  • compound ET-1 was evaporated onto the hole blocking layer to form an electron transport layer having a thickness of 20 nm.
  • Example 1 An organic EL element according to Example 1 was produced.
  • the device configuration of the organic EL element according to Example 1 is roughly shown as follows.
  • the numbers in parentheses expressed as percentages (97%:3%) indicate the ratios (mass%) of compounds HT-1 and HA-1 in the hole injection layer, and the numbers in percentages (74%:25%:1%) indicate the ratios (mass%) of compounds Host-1, STZ-1, and BD-1 in the light-emitting layer.
  • percentages 97%:3%
  • percentages 74%:25%:1%
  • Examples 2 to 5 The organic EL devices of Examples 2 to 5 were prepared in the same manner as in Example 1, except that the compound Host-1 used as the host material in the emitting layer of Example 1 was changed to a compound shown in Table 1.
  • Comparative Examples 1 to 2 The organic EL devices of Comparative Examples 1 and 2 were prepared in the same manner as in Example 1, except that the compound Host-1 used as the host material in the light-emitting layer of Example 1 was changed to a compound shown in Table 1.
  • the organic EL elements of Examples 1 to 5 contained a host material represented by general formula (1), a sensitizing material, and a fluorescent material in the light-emitting layer, and emitted light with higher efficiency than the organic EL elements of Comparative Examples 1 and 2.
  • the delayed fluorescence was confirmed by measuring the transient PL using the apparatus shown in Figure 2.
  • the compound STZ-1 was dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption.
  • the sample solution was frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to prepare an oxygen-free sample solution saturated with argon.
  • the fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions.
  • the total fluorescence quantum yield was calculated using the fluorescence area intensities of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.
  • the value of X D /X P is 0.05 or more.
  • the amount of Prompt luminescence and Delay luminescence and the ratio thereof can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of Prompt luminescence and Delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG.
  • the amount of Delay luminescence was 5% or more relative to the amount of Prompt luminescence (prompt luminescence) for the compound STZ-1.
  • the value of X D /X P for the compound STZ-1 was 0.05 or more.
  • the energy gap T 77K of the compound to be measured was measured by the method for measuring the energy gap T 77K described above in the section "Relationship between triplet energy and energy gap at 77 [K]".
  • the compound to be measured was dissolved in toluene at a concentration of 2.0 ⁇ 10 ⁇ 5 mol/L to prepare a measurement sample.
  • the measurement sample placed in a quartz cell was irradiated with continuous light in the ultraviolet-visible region at room temperature (300K) to measure the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength).
  • a spectrophotometer U-3900/3900H model manufactured by Hitachi High-Tech Science Corporation was used to measure the absorption spectrum.
  • the compound to be measured was dissolved in toluene at a concentration of 4.9 ⁇ 10 ⁇ 6 mol/L to prepare a measurement sample.
  • the compound BD-1 had a maximum peak wavelength ⁇ FL of 455 nm, an emission spectrum half width FWHM of 23 nm, and a Stokes shift of 14 nm.
  • the obtained crude product was purified by column chromatography to obtain a white solid (4.08 g, yield 78%).
  • the obtained crude product was purified by column chromatography to obtain a white solid (4.20 g, yield 79%).
  • organic electroluminescence element 10... organic layer, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer.

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Abstract

La présente invention concerne un composé représenté par la formule générale (1). (dans la formule générale (1), Ar1 est un groupe représenté par la formule générale (11) ou (12) ; dans la formule générale (14), deux * représentent des positions de liaison avec les cycles carbazole dans la formule générale (1) ; lorsqu'un ou plusieurs ensembles de, par exemple, des ensembles comprenant deux ou plus de R1 à R4 adjacents sont liés l'un à l'autre, au moins l'un de R1 à R19 est un groupe représenté par la formule générale (13) ; et lorsque l'un quelconque, par exemple, des ensembles comprenant deux ou plus de deux R1 à R4 adjacents ne sont pas liés l'un à l'autre, au moins l'un de R1 à R15 est un groupe représenté par la formule générale (13).)
PCT/JP2024/010081 2023-03-16 2024-03-14 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique WO2024190882A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150105201A (ko) * 2014-03-05 2015-09-16 주식회사 엠비케이 신규한 유기발광화합물 및 이를 포함하는 유기전계발광소자
US20160155949A1 (en) * 2014-11-28 2016-06-02 Luminescence Technology Corp. Phenanthroline-bsaed compound and use thereof
WO2017111543A1 (fr) * 2015-12-23 2017-06-29 주식회사 두산 Composé organique et dispositif électroluminescent organique comprenant ce composé
US20220135601A1 (en) * 2020-11-05 2022-05-05 Samsung Display Co., Ltd. Heterocyclic compound, light-emitting device including the heterocyclic compound, and electronic apparatus including the light-emitting device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150105201A (ko) * 2014-03-05 2015-09-16 주식회사 엠비케이 신규한 유기발광화합물 및 이를 포함하는 유기전계발광소자
US20160155949A1 (en) * 2014-11-28 2016-06-02 Luminescence Technology Corp. Phenanthroline-bsaed compound and use thereof
WO2017111543A1 (fr) * 2015-12-23 2017-06-29 주식회사 두산 Composé organique et dispositif électroluminescent organique comprenant ce composé
US20220135601A1 (en) * 2020-11-05 2022-05-05 Samsung Display Co., Ltd. Heterocyclic compound, light-emitting device including the heterocyclic compound, and electronic apparatus including the light-emitting device

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