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WO2025009454A1 - Composé, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, élément électroluminescent organique et dispositif électronique Download PDF

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WO2025009454A1
WO2025009454A1 PCT/JP2024/023242 JP2024023242W WO2025009454A1 WO 2025009454 A1 WO2025009454 A1 WO 2025009454A1 JP 2024023242 W JP2024023242 W JP 2024023242W WO 2025009454 A1 WO2025009454 A1 WO 2025009454A1
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真人 三谷
裕 工藤
一輝 寺田
圭 吉田
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Idemitsu Kosan Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/90—Assemblies of multiple devices comprising at least one organic light-emitting element
    • H10K59/95—Assemblies of multiple devices comprising at least one organic light-emitting element wherein all light-emitting elements are organic, e.g. assembled OLED displays
    • 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
    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers

Definitions

  • the present invention relates to a compound, an organic electroluminescence element, and an electronic device.
  • Organic electroluminescence elements (hereinafter sometimes referred to as "organic EL elements”) are applied to full-color displays such as mobile phones and televisions.
  • organic EL elements When a voltage is applied to 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.
  • the performance of an organic EL element includes, for example, luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.
  • Patent Document 1 discusses ways to improve the performance of an organic EL element.
  • the object of the present invention is to provide a compound capable of improving the performance of an organic electroluminescence element, to provide an organic electroluminescence element containing the compound, and to provide an electronic device incorporating the organic electroluminescence element.
  • R 1 to R 14 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent 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
  • L1 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,
  • L 1 is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, n is 0, 1, 2 or 3;
  • n is 0, -(L 1 ) 0 - is a single bond;
  • Ar1 is a substituted or unsubstituted phenalenyl group, a substituted or
  • Rp1 and Rp2 are each independently 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, and * indicates a bonding position.
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 801 , and R 802 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,
  • the plurality of R 903 are present, the plurality of R 903 are the same or different from each other,
  • the plurality of R 904 are present, the plurality of R 904
  • an organic electroluminescence device containing a compound according to one aspect of the present invention as a first compound.
  • an electronic device is provided that is equipped with an organic electroluminescence element according to one aspect of the present invention.
  • FIG. 4 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention.
  • FIG. 11 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a fourth embodiment of the present invention.
  • 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, deuterium atom, or 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 of 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 is, unless otherwise specified in this specification, 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 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.
  • the "unsubstituted arylene 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 number of ring atoms in the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
  • the "unsubstituted alkylene 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.
  • 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).
  • heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group” is an "unsubstituted heterocyclic group"
  • substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group” is a "substituted heterocyclic group”.
  • heterocyclic group simply includes both an "unsubstituted heterocyclic group” and 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 "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, pyrimidinyl group, A 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, A quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolin
  • 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).
  • the examples of the "unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group” in the specific example group G6B are replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group” in the specific example group G6B is further replaced with a substituent.
  • Unsubstituted cycloalkyl groups (specific example group G6A): A cyclopropyl group, A cyclobutyl group, Cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
  • Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl group.
  • 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 in 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, unless otherwise specified in this specification.
  • dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.
  • 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", or 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 two adjacent rings” 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 shown 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 or 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 below.
  • substituents in the case of "substituted or unsubstituted” include, 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” means a range including the number AA written before “AA-BB” as the lower limit and the number BB written after "AA-BB” as the upper limit.
  • the compound according to the first embodiment is a compound represented by the following general formula (1).
  • R 1 to R 14 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent 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
  • L1 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,
  • L 1 is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, n is 0, 1, 2 or 3;
  • n is 0, -(L 1 ) 0 - is a single bond;
  • Ar1 is a substituted or unsubstituted phenalenyl group, a substituted or
  • Rp1 and Rp2 are each independently 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, and * indicates a bonding position.
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 801 , and R 802 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,
  • the plurality of R 903 are present, the plurality of R 903 are the same or different from each other,
  • the plurality of R 904 are present, the plurality of R 904
  • the dibenz[a,c]anthracene ring in general formula (1) means the dibenz[a,c]anthracene ring itself to which R 1 to R 14 are bonded, and does not mean the dibenz[a,c]anthracene ring in the case where R 1 to R 14 have a dibenz[a,c]anthracene ring.
  • the compound according to the present embodiment has a structure in which Ar 1 is bonded directly or via L 1 to a dibenz[a,c]anthracene ring, and Ar 1 is an aryl group or a heterocyclic group having a specific fused ring structure as described above.
  • Ar 1 is bonded directly or via L 1 to a dibenz[a,c]anthracene ring
  • Ar 1 is an aryl group or a heterocyclic group having a specific fused ring structure as described above.
  • the device performance of an organic electroluminescence device for example, one or more performances selected from the group consisting of luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and life
  • the life of an organic electroluminescence device can be extended.
  • R 1 to R 14 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring are each preferably 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 19 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (12).
  • R 1 to R 14 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring, are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms, or a group represented by the general formula (12).
  • At least one of R 1 , R 3 , R 6 , R 8 , R 9 , R 10 , R 13 and R 14 is preferably a group represented by the general formula (12).
  • R 1 to R 14 that are not the group represented by the general formula (12) are preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R 1 to R 14 that are not the group represented by the general formula (12) are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms.
  • R 1 to R 14 that are not the group represented by the general formula (12) are also preferably hydrogen atoms.
  • the compound represented by the general formula (1) is preferably represented by the following general formula (10):
  • R 1 , R 3 , R 6 , R 8 , R 9 , R 10 , R 13 and R 14 are respectively defined as R 1 , R 3 , R 6 , R 8 , R 9 , R 10 , R 13 and R 14 in the general formula (1).
  • the compound represented by the general formula (1) is preferably represented by the following general formula (11):
  • R 14 has the same meaning as R 14 in the general formula (1), and n, L 1 , and Ar 1 have the same meaning as n, L 1 , and Ar 1 in the general formula (12), respectively.
  • R 14 in the general formula (11) and the group represented by “*-(L 1 ) n -Ar 1 " are different from each other.
  • R 14 is preferably a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms.
  • R 1 and R 8 are a group represented by the general formula (12).
  • both R 9 and R 14 may be hydrogen atoms.
  • the compound represented by the general formula (1) is also preferably a compound represented by the following general formula (13), (14) or (15).
  • R13 has the same meaning as R13 in the general formula (1)
  • R1 has the same meaning as R1 in the general formula (1)
  • R3 has the same meaning as R3 in the general formula (1)
  • n, L1 , and Ar1 have the same meaning as n, L1 , and Ar1 in the general formula (12), respectively.
  • R 13 in the general formula (13) and the group represented by "*-(L 1 ) n -Ar 1 " may be the same group or different groups.
  • R 1 in the general formula (14) and the group represented by "*-(L 1 ) n -Ar 1 " may be the same group or different groups.
  • R 3 in the general formula (15) and the group represented by "*-(L 1 ) n -Ar 1 " may be the same group or different groups.
  • n in the compound represented by the general formula (1) is preferably 0 or 1.
  • n in the general formula (12) is also preferably 0.
  • n in the general formula (12) is 0, -(L) 0 - is a single bond, that is, Ar 1 is directly bonded to the dibenz[a,c]anthracene ring.
  • the compounds represented by the general formulae (11), (13), (14) and (15) are represented by the following general formulae (11A), (13A), (14A) and (15A), respectively.
  • R 1 , R 3 , R 13 and R 14 are respectively defined as R 1 , R 3 , R 13 and R 14 in the general formula (1), and Ar 1 is respectively defined as Ar 1 in the general formula (12).
  • R 14 and Ar 1 in the general formula (11A) are different groups.
  • R 13 and Ar 1 in the general formula (13A) may be the same group or different groups.
  • R 1 and Ar 1 in the general formula (14A) may be the same group or different groups.
  • R 3 and Ar 1 in the general formula (15A) may be the same group or different groups.
  • R 14 in the general formulae (11) and (11A), R 13 in the general formulae (13) and (13A), R 1 in the general formulae (14) and (14A), and R 3 in the general formulae (15) and (15A) are each independently preferably 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 19 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (12).
  • R 14 in the general formulae (11) and (11A), R 13 in the general formulae (13) and (13A), R 1 in the general formulae (14) and (14A), and R 3 in the general formulae (15) and (15A) are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms, or a group represented by the general formula (12).
  • the compound according to this embodiment preferably has one or two groups represented by the general formula (12) in the molecule, and more preferably has only one group.
  • L1 in the compound represented by the general formula (1) is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, and more preferably a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.
  • L 1 in the compound represented by the general formula (1) is also preferably a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.
  • L 1 in the compound represented by the general formula (1) is also preferably a substituted or unsubstituted m-phenylene group or a substituted or unsubstituted p-phenylene group.
  • L1 is also preferably any group selected from the group consisting of groups represented by the following general formulas (L1) to (L23).
  • Ar 1 in the compound represented by the general formula (1) is a heterocyclic group
  • the ring of the heterocyclic group preferably contains an oxygen atom
  • Ar 1 in the compound represented by the general formula (1) is a heterocyclic group
  • Ar 1 as a heterocyclic group is a substituted or unsubstituted furanyl group; a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[1,2-d]furanyl group, a substituted or unsubstituted dinaphthofuranyl group; a substituted or unsubstituted benzobisbenzofuranyl group; A substituted or unsubstituted benzo[b]phenanthrofuranyl group, or a
  • Ar 1 in the compound represented by the general formula (1) is a substituted or unsubstituted furanyl group; a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[1,2-d]furanyl group, a substituted or unsubstituted dinaphthofuranyl group; a substituted or unsubstituted benzobisbenzofuranyl group; Also preferred is a substituted or unsubstituted benzo[b]phenanthrofuranyl group, or a substituted or unsubstituted xantheny
  • Ar 1 in the compound represented by the general formula (1) is a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted dibenz[a,c]anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted di
  • Ar 1 in the compound represented by the general formula (1) is a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, A substituted or unsubstituted indenofluoreny
  • Ar 1 in the compound represented by the general formula (1) is also preferably any one of the groups represented by the following general formulas (101) to (112).
  • R 101 to R 109 , R 111 to R 165 and R 166 to R 187 each independently represent 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 19 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * indicates the bond position.
  • Ar 1 in the compound represented by the general formula (1) is also preferably any one of the groups represented by the general formulas (101) to (110).
  • Ar 1 in the compound represented by the general formula (1) is also preferably a group represented by the general formula (101), (103), (106), (111) or (112).
  • Ar 1 in the compound represented by the general formula (1) is also preferably a group represented by the general formula (101).
  • Ar 1 in the compound represented by the general formula (1) is also preferably a group represented by the general formula (111).
  • Ar 1 in the compound represented by general formula (1) is also preferably any one of the groups represented by the following general formulae (AR101) to (AR224).
  • the "optional substituents" of the groups represented by the general formulae (AR101) to (AR224) are preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms, and more preferably an unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • Ar 1 in the compound represented by the general formula (1) is also preferably any one of the groups represented by the general formulas (AR101) to (AR222).
  • Ar 1 in the compound represented by the general formula (1) is also preferably a group represented by the general formula (AR101), (AR104), (AR147), (AR152), (AR169) or (AR223).
  • Ar 1 in the compound represented by the general formula (1) is also preferably a group represented by the general formula (AR101) or (AR104).
  • Ar 1 in the compound represented by general formula (1) is also preferably a group represented by general formula (AR147) or (AR152).
  • Ar 1 in the compound represented by the general formula (1) is also preferably a group represented by (AR223).
  • the substituted or unsubstituted benzobisbenzofuranyl group is preferably a group represented by the general formulas (AR199) to (AR209).
  • Ar 1 in the compound represented by the general formula (1) is not a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • any pair of two or more adjacent groups among R 1 to R 14 are not bonded to each other.
  • the compound represented by the general formula (1) does not have an anthracene structure in the molecule.
  • the "anthracene structure” here refers to the structure of the anthracene ring itself in which three benzene rings are fused, and structures in which one or more rings are further fused to the anthracene ring are not included in the “anthracene structure” here. Therefore, for example, a structure in which four benzene rings are fused, such as benz[a]anthracene, and a structure in which five benzene rings are fused, such as dibenz[a,c]anthracene ring, are not included in the "anthracene structure” here.
  • the compound represented by the general formula (1) does not have a benzoxanthene structure in the molecule.
  • the "benzoxanthene structure” here refers to the benzo[kl]xanthene structure shown below.
  • R 9 and R 14 are not phenanthryl groups.
  • the compound represented by the general formula (1) does not contain a phosphorus atom in the molecule.
  • the compound represented by the general formula (1) does not contain a heterocyclic group containing at least one of a nitrogen atom and a sulfur atom as a ring-forming atom in the molecule.
  • the compound represented by the general formula (1) does not contain an aryl group having 20 or more ring carbon atoms in the molecule.
  • the compound represented by formula (1) contains at least one deuterium atom.
  • R 1 to R 14 is a deuterium atom.
  • L 1 contains one or more deuterium atoms.
  • Ar 1 contains one or more deuterium atoms.
  • At least one of R 1 to R 14 that is not a group represented by the general formula (12) is a deuterium atom.
  • the hydrogen atoms in R 1 to R 14 are preferably deuterium atoms.
  • R 1 to R 14 that are not the group represented by the general formula (12) are deuterium atoms.
  • the substituent in the case of "substituted or unsubstituted” is preferably an unsubstituted alkyl group having 1 to 6 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 compound according to this embodiment can be produced according to the synthesis method described in the Examples below, or by following the synthesis method and using known alternative reactions and raw materials suited to the target compound.
  • 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 an organic EL device contains the compound according to the first embodiment.
  • the compound according to the first embodiment is preferably a host material.
  • the material for an organic EL device may contain the compound according to the first embodiment as a host material and other compounds such as a dopant material.
  • the compound according to the first embodiment is useful as a material for an organic EL device, and is useful as a material for the light-emitting layer of an organic EL device, and is particularly useful as a host material for the blue light-emitting layer.
  • Organic EL element according to a third embodiment contains the compound according to the first embodiment as a first compound.
  • One aspect of the organic EL element according to this embodiment has an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • This organic layer includes at least one layer containing an organic compound.
  • this organic layer is configured by laminating multiple layers containing an organic compound.
  • Each of the layers containing an organic compound that constitute the organic layer may independently further include an inorganic compound.
  • At least one of the organic layers contains a first compound (a compound according to the first embodiment).
  • the organic layer preferably has a light-emitting region.
  • the light-emitting region preferably includes at least one light-emitting layer.
  • the at least one light-emitting layer contains a first compound (a compound according to the first embodiment).
  • the organic EL element according to the present embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when the element is driven, and more preferably emits light having a maximum peak wavelength of 430 nm or more and 480 nm or less when the element is driven.
  • the organic EL element according to the present embodiment more preferably emits light having a maximum peak wavelength of 470 nm or less when the element is driven, and even more preferably emits light having a maximum peak wavelength of 465 nm or less when the element is driven.
  • the organic EL element according to the present embodiment more preferably emits light having a maximum peak wavelength of 440 nm or more when the element is driven, and even more preferably emits light having a maximum peak wavelength of 445 nm or more when the element is driven.
  • the maximum peak wavelength of light emitted by the organic EL element when the element is driven is measured as follows. A voltage is applied to the organic EL element so that the current density is 10 mA/ cm2 , 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 organic layer may be composed of only the light-emitting layer, but may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.
  • FIG. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment.
  • the organic EL element 1A shown in FIG. 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4.
  • the organic layer 10A includes, in order from the anode 3 side, a hole transport zone 6, a light-emitting region 5A, and an electron transport zone 7.
  • the hole transport zone 6 includes, in order from the anode 3 side, a hole injection layer 61 and a hole transport layer 62.
  • the light-emitting region 5A includes one light-emitting layer 5.
  • the electron transport zone 7 includes, in order from the light-emitting region 5A side, an electron transport layer 71 and an electron injection layer 72.
  • the light-emitting layer contains the compound according to the first embodiment.
  • the compound contained in the light-emitting layer is preferably the first compound (the compound according to the first embodiment).
  • the light-emitting layer contains the first compound (the compound according to the first embodiment) and a light-emitting compound.
  • the light-emitting compound contained in the light-emitting layer is preferably a fluorescent compound.
  • the light-emitting compound contained in the light-emitting layer is a compound represented by the following general formula (5).
  • R 501 to R 507 and R 511 to R 517 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent: Hydrogen atoms, a substituted or unsubstituted alkyl 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
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 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, Preferably, it is 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, 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 90
  • One of the groups consisting of two or more adjacent groups among R 501 to R 507 and R 511 to R 517 is, for example, a combination such as a group consisting of R 501 and R 502 , a group consisting of R 502 and R 503 , a group consisting of R 503 and R 504 , a group consisting of R 505 and R 506 , a group consisting of R 506 and R 507 , a group consisting of R 501 , R 502 and R 503 , etc.
  • the compound represented by the general formula (5) is a compound represented by the following general formula (52):
  • R 531 to R 534 and R 541 to R 544 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 531 to R 534 , R 541 to R 544 , and R 551 and R 552 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent: Hydrogen 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, R 561 to R 564 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstit
  • the light-emitting compound contained in the light-emitting layer is a compound represented by the following general formula (6).
  • 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 601 and R 602 each independently bond to the ring a, ring b or ring c to form a substituted or unsubstituted heterocycle or do not form a substituted or unsubstituted heterocycle; R 601 and R 602 which do not form a substituted or unsubstituted heterocycle 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 atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalky
  • ring a, ring b, and ring c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocycles having 5 to 50 ring atoms) that are fused to the central fused two-ring structure of general formula (6) composed of a boron atom and two nitrogen atoms.
  • the "aromatic hydrocarbon rings" of ring a, ring b, and ring c have the same structure as a compound in which a hydrogen atom has been introduced into an "aryl group".
  • the "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of formula (6) as ring-forming atoms.
  • the "aromatic hydrocarbon ring” of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of formula (6) as ring-forming atoms.
  • substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms include compounds in which a hydrogen atom has been introduced into the "aryl group” described in specific example group G1.
  • the "heterocycles" of ring a, ring b and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group”.
  • the "heterocycle” of ring a contains three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms.
  • heterocycle of rings b and c contains two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms.
  • Specific examples of "substituted or unsubstituted heterocycles having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.
  • R 601 and R 602 may each independently bond to a ring, b ring, or c ring to form a substituted or unsubstituted heterocycle.
  • the heterocycle in this case includes the nitrogen atom on the central fused two-ring structure of the general formula (6).
  • the heterocycle in this case may include a heteroatom other than a nitrogen atom.
  • R 601 and R 602 bond to a ring, b ring, or c ring specifically means that an atom constituting a ring, b ring, or c ring is bonded to an atom constituting R 601 and R 602.
  • R 601 may bond to a ring to form a two-ring fused (or three-ring or more fused) nitrogen-containing heterocycle in which the ring containing R 601 is fused to the ring a.
  • Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two-ring fused or more heterocyclic groups in the specific example group G2. The above also applies when R 601 is bonded to ring b, when R 602 is bonded to ring a, and when R 602 is bonded to ring c.
  • R 601 and R 602 may each independently not be bonded to ring a, ring b or ring c.
  • the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms. In one embodiment, the ring a, the ring b, and the ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
  • R 601 and R 602 in the general formula (6) are each independently 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, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by the general formula (6) is a compound represented by the following general formula (62):
  • R 601A is bonded to one or more selected from the group consisting of R 611 and R 621 to form a substituted or unsubstituted heterocycle or does not form a substituted or unsubstituted heterocycle
  • R 602A is bonded to one or more selected from the group consisting of R 613 and R 614 to form a substituted or unsubstituted heterocycle or does not form a substituted or unsubstituted heterocycle
  • R 601A and R 602A which do not form a substituted or unsubstituted heterocycle 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 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 atom
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 each independently represent 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,
  • R 601A and R 602A in the general formula (62) are groups corresponding to R 601 and R 602 in the general formula (6), respectively.
  • R 601A and R 611 may be bonded to form a two-ring condensed (or three-ring or more condensed) nitrogen-containing heterocycle in which a ring containing them and a benzene ring corresponding to the ring a are condensed.
  • Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two-ring or more condensed heterocyclic group in the specific example group G2. The same applies when R 601A and R 621 are bonded, when R 602A and R 613 are bonded, and when R 602A and R 614 are bonded.
  • One or more pairs of adjacent two or more of R 611 to R 621 may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted fused ring.
  • R 611 and R 612 may be bonded to a 6-membered ring to which they are bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is fused, and the fused ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.
  • the compound represented by the general formula (6) is a compound represented by the following general formula (63):
  • R 611 to R 617 , R 601A and R 602A each independently have the same meaning as R 611 to R 617 , R 601A and R 602A in the general formula (62),
  • X4 is an oxygen atom or a sulfur atom;
  • One or more pairs of adjacent two or more of R 701 to R 704 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 701 to R 704 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted al
  • the light-emitting compound contained in the light-emitting layer is a compound represented by the following general formula (3A).
  • Ra 301 to Ra 310 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,
  • At least one of Ra 301 to Ra 310 is a monovalent group represented by the following general formula (31A):
  • Ra 301 to Ra 310 which do not form a monocycle, do not form a condensed ring, and are not a monovalent group represented by the following general formula (31A) each independently represent: Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or un
  • Ara 301 and Ara 302 are each independently 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
  • La 301 , La 302 and La 303 each independently represent Single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms
  • * indicates the bonding position in the pyrene ring in the general formula (3A).
  • the light-emitting compound contained in the light-emitting layer is preferably a compound that exhibits light emission (preferably fluorescent emission) with a maximum peak wavelength of 500 nm or less.
  • the maximum peak wavelength of the light emission (preferably fluorescent emission) exhibited by the light-emitting compound is preferably 480 nm or less, more preferably 460 nm or less, and even more preferably 455 nm or less.
  • the maximum peak wavelength of the light emission (preferably fluorescent emission) exhibited by the light-emitting compound is preferably 430 nm or more, more preferably 440 nm or more, and even more preferably 445 nm or more.
  • the method for measuring the maximum peak wavelength of a compound in this specification is as follows. A toluene solution of the compound to be measured at 10 -6 mol/L or more and 10 -5 mol/L or less is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300K). The emission spectrum can be measured using a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. The emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength at which the emission intensity is maximum is defined as the maximum emission peak wavelength. Note that in this specification, the maximum peak wavelength may be referred to as the maximum fluorescence emission peak wavelength (FL-peak).
  • the first compound (a compound according to the first embodiment) is a host material (sometimes referred to as a matrix material), and the light-emitting compound is a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material).
  • a "host material” is, for example, a material that is contained in "50% by mass or more of a layer.” Therefore, for example, in the case of the organic EL element according to this embodiment, the light-emitting layer contains the first compound (the compound according to the first embodiment) in an amount of 50% by mass or more of the total mass of the light-emitting layer.
  • the thickness of the light-emitting layer 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 of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity.
  • the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress an increase in the driving voltage.
  • the contents of the first compound (the compound according to the first embodiment) and the light-emitting compound in the light-emitting layer are preferably, for example, in the following ranges, respectively.
  • the content of the first compound (the compound according to the first embodiment) is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.
  • the content of the luminescent compound is preferably 1 mass % or more and 10 mass % or less, more preferably 1 mass % or more and 7 mass % or less, and even more preferably 1 mass % or more and 5 mass % or less.
  • the upper limit of the total content of the first compound (the compound according to the first embodiment) and the light-emitting compound in the light-emitting layer is 100 mass %.
  • this embodiment does not exclude the case where the light-emitting layer contains a material other than the first compound (the compound according to the first embodiment) and the light-emitting compound.
  • the light-emitting layer may contain only one type of the first compound (the compound according to the first embodiment), or may contain two or more types.
  • the light-emitting layer may contain only one type of the light-emitting compound, or may contain two or more types.
  • 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.
  • anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, and the like.
  • ITO indium oxide-tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide indium oxide-zinc oxide
  • tungsten oxide indium oxide containing zinc oxide, graphene, and the like.
  • Au gold
  • platinum Pt
  • Ni nickel
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • Fe iron
  • Co cobalt
  • Cu copper
  • palladium Pd
  • titanium Ti
  • nitrides of metal materials e.g., titanium nitride
  • 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.
  • cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or 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 as euro
  • 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 hole transport zone is disposed between the anode and the light emitting region.
  • the hole transport region includes, in order from the anode side, a hole injection layer and a hole transport layer.
  • the hole transport region includes, in order from the light emitting region side, a hole injection layer, a hole transport layer and an electron blocking layer.
  • the hole injection layer is a layer containing a substance with high hole injection properties, 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, etc.
  • substances with high hole injection properties include the low molecular weight organic compounds 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), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD).
  • TDATA 4,
  • aromatic amine compounds include aromatic amine compounds such as [N-(9-phenylcarbazol-3-yl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), as well as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-
  • a polymeric compound oligomer, dendrimer, polymer, etc.
  • polymeric 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]phenyl-N'
  • polymeric compounds to which an acid has been added such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and 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 organic EL element according to this embodiment preferably has a hole transport layer between the anode and the light emitting region.
  • 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 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]biphenyl, etc.
  • 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 carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth.
  • CBP carbazole derivatives
  • CzPA 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene
  • PCzPA 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole
  • anthracene derivatives such as t-BuDNA, DNA, and DPAnth.
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltri
  • the layer containing the substance having a high hole transporting property may be not only a single layer, but also a stack of two or more layers made of the above substances.
  • Specific examples of the materials (hole transport zone materials) used in each layer of the hole transport zone include the following compounds, however, the present invention is not limited to these specific examples of the hole transport zone materials.
  • the electron-transporting zone is disposed between the light-emitting region and the cathode.
  • the electron transport zone includes, in order from the light emitting region side, an electron transport layer and an electron injection layer.
  • the electron transport zone includes, in order from the light emitting region side, a hole blocking layer, an electron transport layer and an electron injection layer.
  • the organic EL element preferably has an electron transport layer between the cathode and the light emitting region.
  • 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.
  • a benzimidazole compound can also be preferably used.
  • the substances described here are mainly substances having an electron mobility of 10 -6 cm 2 /(V ⁇ s) or more. Note that, as long as the substance has a higher electron transporting property than a hole transporting property, a substance other than the above may be used as the electron transporting layer.
  • the electron transporting layer may be formed of a single layer, or may be formed of two or more layers of the above substances stacked together.
  • the electron transport layer can also be made of a polymer compound.
  • a polymer compound for example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), etc. can be used.
  • 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)]
  • Specific examples of the electron transport material that can be used in the electron transport layer include the following compounds, but the present invention is not limited to these specific examples of the electron transport material.
  • 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. may 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 of the present embodiment 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 of the present embodiment 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 electroluminescent element according to this embodiment contains the compound according to the first embodiment (first compound), and therefore the element performance is improved. According to one aspect of the organic electroluminescent element according to this embodiment, the life span is extended.
  • the organic EL element according to the fourth embodiment differs from the organic EL element according to the third embodiment in that the light-emitting region includes at least two light-emitting layers.
  • the organic EL element according to the fourth embodiment is similar to the organic EL element according to the third embodiment in terms other than the light-emitting region.
  • the same components as those in the third embodiment are given the same reference numerals or names, and the description is omitted or simplified.
  • the same materials and compounds as those described in the third embodiment can be used.
  • FIG. 2 shows a schematic configuration of an example of the organic EL element according to this embodiment.
  • 2 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10B disposed between the anode 3 and the cathode 4.
  • the organic layer 10B includes, in order from the anode 3 side, a hole transport zone 6, a first light-emitting region 5B, and an electron transport zone 7.
  • the hole transport zone 6 includes, in order from the anode 3 side, a hole injection layer 61 and a hole transport layer 62.
  • the first light-emitting region 5B includes, in order from the anode 3 side, a first light-emitting layer 51 and a second light-emitting layer 52.
  • the electron transport zone 7 includes, in order from the light-emitting region 5A side, an electron transport layer 71 and an electron injection layer 72.
  • the organic layer has a light-emitting region, the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer contains a first compound.
  • the second light-emitting layer contains a second compound.
  • the organic EL element according to the present embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when the element is driven, and more preferably emits light having a maximum peak wavelength of 430 nm or more and 480 nm or less when the element is driven.
  • the organic EL element according to the present embodiment more preferably emits light having a maximum peak wavelength of 470 nm or less when the element is driven, and even more preferably emits light having a maximum peak wavelength of 465 nm or less when the element is driven.
  • the organic EL element according to the present embodiment more preferably emits light having a maximum peak wavelength of 440 nm or more when the element is driven, and even more preferably emits light having a maximum peak wavelength of 445 nm or more when the element is driven.
  • the organic EL element according to the present embodiment it is also preferable that the second light-emitting layer is disposed between the anode and the cathode, and the first light-emitting layer is disposed between the anode and the second light-emitting layer. That is, the organic EL element according to the present embodiment may have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order.
  • the organic EL element according to this embodiment it is also preferable that a first light-emitting layer is disposed between the anode and the cathode, and a second light-emitting layer is disposed between the anode and the first light-emitting layer.
  • the organic EL element according to this embodiment may have an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order.
  • the first compound is preferably the compound according to the first embodiment.
  • the second compound is not particularly limited, but examples thereof include a second compound represented by the following general formula (2).
  • the second compound is a compound represented by the following general formula (2).
  • R 201 to R 208 each independently represent 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 905 ), a group represented by -N(R 906 )(R 907 ); a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, A
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 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,
  • the plurality of R 903 are present
  • the plurality of R 903 are the same or different from each other
  • a plurality of R 904 are present, the plurality
  • the second compound is a compound having at least one group represented by the following general formula (HY1) in the molecule.
  • R Y1 to R Y8 and R Y11 to R Y14 each independently represent Hydrogen atoms, Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted alkyl 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 905 ), a group represented by -N(R 906 )(R 907 ); a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
  • the group represented by general formula (HY1) is represented by the following general formula (HY10).
  • the second compound is a compound having at least one group represented by the following general formula (HY10) in the molecule.
  • R Y1 to R Y8 and Z 2 are respectively defined as R Y1 to R Y8 and Z 2 in the general formula (HY1), However, one selected from R Y1 to R Y8 is a single bond bonded to *ey, *fy indicates the bond position to an atom in the second compound.
  • the second compound is a compound having at least one group represented by the general formula (HY1) in the molecule, and ny is 1.
  • the second compound is a compound having at least one group selected from the group consisting of groups represented by the following general formulae (HY11), (HY12), and (HY13) in the molecule.
  • R Y1 to R Y8 , R Y11 to R Y14 and Z2 are respectively defined as R Y1 to R Y8 , R Y11 to R Y14 and Z2 in the general formula (HY1), However, one of R Y1 to R Y8 and R Y11 to R Y14 is a single bond bonded to *ey; *fy indicates the bond position to an atom in the second compound.
  • the second compound is a compound represented by the general formula (2) and has at least one group represented by the general formula (HY1) in the molecule of the compound represented by the general formula (2).
  • At least one of Ar 201 and Ar 202 in the general formula (2) is a group represented by the general formula (HY1).
  • Ar 201 or Ar 202 in the general formula (2) is a group represented by the general formula (HY1).
  • the second compound is represented by the general formula (2)
  • the compound represented by general formula (2) has at least one group selected from the group consisting of groups represented by general formulas (HY11), (HY12) and (HY13) in the molecule thereof.
  • At least one of Ar 201 and Ar 202 in the general formula (2) is any group selected from the group consisting of groups represented by the general formulae (HY11), (HY12), and (HY13).
  • Ar 201 or Ar 202 in the general formula (2) is any group selected from the group consisting of groups represented by the general formulae (HY11), (HY12), and (HY13).
  • the second compound has at least one group selected from the group consisting of groups represented by the general formulas (HY1), (HY10), (HY11), (HY12) and (HY13) in the molecule, thereby improving the excitation resistance of the second compound.
  • all of the groups described as "substituted or unsubstituted" in the second compound are "unsubstituted” groups.
  • the second compound according to this embodiment can be produced by a known method, or can be produced by following the method and using known alternative reactions and raw materials suited to the target product.
  • Specific Example of the Second Compound Specific examples of the second compound according to this embodiment include the following compounds. However, the present invention is not limited to these specific examples.
  • a deuterium atom is represented as D in a chemical formula
  • a protium atom is represented as H or is omitted.
  • D represents a deuterium atom
  • z, z1, z4, z5, and z6 each represent the number of deuterium atoms bonded to the ring
  • z is an integer between 1 and 8
  • z1 is an integer between 1 and 9
  • z4 and z5 are each an integer between 1 and 5
  • z6 is an integer between 1 and 7.
  • the first light-emitting layer contains a first light-emitting compound.
  • the first light-emitting compound is preferably a fluorescent compound.
  • the second light-emitting layer contains a second light-emitting compound.
  • the second light-emitting compound is preferably a fluorescent compound.
  • the first light-emitting compound and the second light-emitting compound are preferably each independently the light-emitting compound described in the third embodiment.
  • it is preferable that the first light-emitting compound and the second light-emitting compound are each independently a compound that emits light having a maximum peak wavelength of 500 nm or less.
  • the first light-emitting compound is preferably a compound that exhibits luminescence (preferably fluorescent emission) with a maximum peak wavelength of 500 nm or less.
  • the maximum peak wavelength of the luminescence (preferably fluorescent emission) exhibited by the first luminescent compound is preferably 480 nm or less, more preferably 460 nm or less, and even more preferably 455 nm or less.
  • the maximum peak wavelength of the luminescence (preferably fluorescent emission) exhibited by the first luminescent compound is preferably 430 nm or more, more preferably 440 nm or more, and even more preferably 445 nm or more.
  • the second light-emitting compound is preferably a compound that exhibits luminescence (preferably fluorescent emission) with a maximum peak wavelength of 500 nm or less.
  • the maximum peak wavelength of the luminescence (preferably fluorescent emission) exhibited by the second luminescent compound is preferably 480 nm or less, more preferably 460 nm or less, and even more preferably 455 nm or less.
  • the maximum peak wavelength of the luminescence (preferably fluorescent emission) exhibited by the second luminescent compound is preferably 430 nm or more, more preferably 440 nm or more, and even more preferably 445 nm or more.
  • the first compound is preferably a first host material, and the first light-emitting compound is preferably a first dopant material.
  • the second compound is preferably a second host material, and the second light-emitting compound is preferably a second dopant material.
  • the triplet energy T 1 (H1) of the first compound and the triplet energy T 1 (H2) of the second compound satisfy the relationship of the following mathematical formula (Mathematical Formula 1).
  • the first compound in the first emitting layer and the second compound in the second emitting layer satisfy the relationship of the mathematical formula (Mathematical Formula 1), whereby the luminous efficiency of the organic EL element is improved.
  • triplet-triplet-annihilation (sometimes referred to as TTA) has been known as a technique for improving the luminous efficiency of an organic EL element.
  • TTA is a mechanism in which a triplet exciton collides with another triplet exciton to generate a singlet exciton.
  • the TTA mechanism is sometimes referred to as the TTF mechanism as described in International Publication WO 2010/134350.
  • the TTF phenomenon will be explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons.
  • the spin state is such that singlet excitons account for 25% and triplet excitons account for 75%.
  • 25% of the singlet excitons emit light when they relax to the ground state, but the remaining 75% of the triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent elements was said to be 25%.
  • the behavior of triplet excitons generated inside organic materials has been theoretically investigated. According to S. M. Bachilo et al. (J.
  • 3 A * triplet excitons collide with each other and a reaction as shown in the following formula occurs.
  • 1 A represents the ground state
  • 1 A * represents the lowest excited singlet exciton.
  • the emission ratio (TTF ratio) derived from TTF in the total emission intensity will be 15/40, i.e., 37.5%.
  • TTF ratio the emission ratio derived from TTF in the total emission intensity
  • triplet excitons generated by recombination of holes and electrons in the first light-emitting layer are unlikely to be quenched at the interface between the first light-emitting layer and the organic layer even if there is an excess of carriers at the interface between the first light-emitting layer and the organic layer that is in direct contact with the first light-emitting layer.
  • the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching due to excess electrons is considered.
  • the organic EL device includes at least two light-emitting layers (i.e., a first light-emitting layer and a second light-emitting layer) that satisfy a predetermined relationship, and includes the first light-emitting layer and the second light-emitting layer such that the triplet energy T 1 (H1) of the first compound in the first light-emitting layer and the triplet energy T 1 (H2) of the second compound in the second light-emitting layer satisfy the relationship of the mathematical formula (Mathematical formula 1).
  • the organic EL element according to the present embodiment comprises, as distinct regions, a first light-emitting layer that mainly generates triplet excitons, and a second light-emitting layer that mainly exerts the TTF mechanism by utilizing triplet excitons transferred from the first light-emitting layer, and uses, as the second compound in the second light-emitting layer, a compound having a smaller triplet energy than the first compound in the first light-emitting layer, thereby providing a difference in triplet energy, thereby improving the luminous efficiency.
  • the triplet energy T 1 (H1) of the first compound and the triplet energy T 1 (H2) of the second compound satisfy the relationship of the following mathematical formula (Mathematical Formula 1A).
  • the singlet energy S 1 (H1) of the first compound in the first emitting layer and the singlet energy S 1 (D1) of the first luminescent compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2).
  • the singlet excitons generated on the molecules of the first compound are easily able to transfer energy from the first compound to the first light-emitting compound, contributing to the fluorescent emission of the first light-emitting compound.
  • the triplet energy T 1 (H1) of the first compound in the first emitting layer and the triplet energy T 1 (D1) of the first luminescent compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2A).
  • the singlet energy S 1 (H2) of the second compound in the second emitting layer and the singlet energy S 1 (D2) of the second luminescent compound satisfy the relationship of the following mathematical formula (Mathematical Formula 3).
  • the second compound in the second light-emitting layer and the second light-emitting compound satisfy the relationship of the mathematical formula (Mathematical formula 3), and therefore the singlet energy of the second light-emitting compound is smaller than the singlet energy of the second compound. Therefore, the singlet excitons generated by the TTF phenomenon transfer energy from the second compound to the second light-emitting compound, and contribute to the fluorescent emission of the second light-emitting compound.
  • the triplet energy T 1 (D2) of the second light-emitting compound in the second light-emitting layer and the triplet energy T 1 (H2) of the second compound satisfy the relationship of the following mathematical formula (Mathematical Formula 3A).
  • the second compound and the second light-emitting compound in the second light-emitting layer satisfy the relationship of the mathematical formula (Mathematical formula 3A), so that triplet excitons generated in the first light-emitting layer transfer energy to the molecule of the second compound, not to the second light-emitting compound having a higher triplet energy, when they move to the second light-emitting layer. Furthermore, triplet excitons generated by recombination of holes and electrons on the molecule of the second compound do not transfer to the second light-emitting compound having a higher triplet energy. Triplet excitons generated by recombination on the molecule of the second light-emitting compound transfer energy quickly to the molecule of the second compound. The triplet excitons of the second compound do not transfer to the second light-emitting compound, but instead collide efficiently with each other on the molecule of the second compound due to the TTF phenomenon, generating singlet excitons.
  • the triplet energy T1 can be measured by the following method.
  • a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement 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 amount of energy calculated from the following conversion formula (F1) based on the wavelength value ⁇ edge [nm] at the intersection of the tangent and the horizontal axis is taken as the triplet energy T1 .
  • Conversion formula (F1): T 1 [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 low-temperature container, an excitation light source, and a light receiving device.
  • a toluene solution of the compound to be measured at 10 -5 mol/L or more and 10 -4 mol/L or less 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 singlet energy S1 .
  • 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 taken 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 first and second emitting layers preferably do not contain a phosphorescent material (dopant material). Moreover, the first and second light-emitting layers preferably do not contain heavy metal complexes and phosphorescent rare earth metal complexes, examples of which include iridium complexes, osmium complexes, and platinum complexes. It is also preferable that the first light-emitting layer and the second light-emitting layer do not contain a metal complex.
  • the thickness of the first light-emitting layer and the second light-emitting layer 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 of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity.
  • the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress an increase in the driving voltage.
  • the contents of the first compound and the first light-emitting compound in the first light-emitting layer are preferably, for example, in the following ranges, respectively.
  • the content of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.
  • the content of the first light-emitting compound is preferably 1 mass % or more and 10 mass % or less, more preferably 1 mass % or more and 7 mass % or less, and even more preferably 1 mass % or more and 5 mass % or less.
  • the upper limit of the total content of the first compound and the first light-emitting compound in the first light-emitting layer is 100 mass %.
  • the first light-emitting layer may contain materials other than the first compound and the first light-emitting compound.
  • the first light-emitting layer may contain only one type of the first compound, or may contain two or more types.
  • the first light-emitting layer may contain only one type of the first light-emitting compound, or may contain two or more types.
  • the contents of the second compound and the second light-emitting compound in the second light-emitting layer are preferably, for example, in the following ranges, respectively.
  • the content of the second compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.
  • the content of the second luminescent compound is preferably 1 mass % or more and 10 mass % or less, more preferably 1 mass % or more and 7 mass % or less, and even more preferably 1 mass % or more and 5 mass % or less.
  • the upper limit of the total content of the second compound and the second light-emitting compound in the second emitting layer is 100 mass %.
  • the present embodiment does not exclude the case where the second light-emitting layer contains a material other than the second compound and the second light-emitting compound.
  • the second light-emitting layer may contain only one type of the second compound, or may contain two or more types.
  • the second light-emitting layer may contain only one type of the second light-emitting compound, or may contain two or more types.
  • the first light-emitting layer and the second light-emitting layer are in direct contact with each other.
  • the layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact with each other” may include, for example, any of the following aspects (LS1), (LS2), and (LS3).
  • LS1 An embodiment in which a region in which a first compound as a host material (hereinafter sometimes referred to as a “first host material”) and a second compound as a host material (hereinafter sometimes referred to as a “second host material”) are both mixed is generated during the process of vapor-depositing a compound for a first emitting layer and a process of vapor-depositing a compound for a second emitting layer, and the region is present at the interface between the first emitting layer and the second emitting layer.
  • first host material a first compound as a host material
  • second host material a second compound as a host material
  • LS2 When the first emitting layer and the second emitting layer contain a light emitting compound, a region in which the first host material, the second host material, and the light emitting compound are mixed is generated during the process of vapor deposition of the compound for the first emitting layer and the process of vapor deposition of the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer.
  • the first emitting layer and the second emitting layer contain a light emitting compound, a region made of the light emitting compound, a region made of the first host material, or a region made of the second host material is generated during the process of vapor deposition of the compound for the first emitting layer and the process of vapor deposition of the compound for the second emitting layer, and the region is present at the interface between the first emitting layer and the second emitting layer.
  • the organic EL element according to this embodiment includes a third light-emitting layer
  • the first light-emitting layer and the second light-emitting layer are in direct contact with each other, and that the second light-emitting layer and the third light-emitting layer are in direct contact with each other.
  • the layer structure in which "the second light-emitting layer and the third light-emitting layer are in direct contact with each other” may include, for example, any of the following aspects (LS4), (LS5), and (LS6).
  • LS4 An embodiment in which a region in which both the second host material and the third host material (the host material contained in the third emitting layer) are mixed is generated during the process of vapor-depositing the compound for the second emitting layer and the process of vapor-depositing the compound for the third emitting layer, and the region is present at the interface between the second emitting layer and the third emitting layer.
  • the second emitting layer and the third emitting layer each contain a light emitting compound
  • a region in which the second host material, the third host material, and the light emitting compound are mixed is generated during the process of vapor deposition of the compound for the second emitting layer and the process of vapor deposition of the compound for the third emitting layer, and this region is present at the interface between the second emitting layer and the third emitting layer.
  • the second emitting layer and the third emitting layer each contain a light emitting compound, a region made of the light emitting compound, a region made of the second host material, or a region made of the third host material is generated during the process of vapor deposition of the compound for the second emitting layer and the process of vapor deposition of the compound for the third emitting layer, and the region is present at the interface between the second emitting layer and the third emitting layer.
  • the organic EL element according to this embodiment may further have an intervening layer as an organic layer.
  • the intervening layer is disposed between the first light-emitting layer and the second light-emitting layer.
  • the intermediate layer is preferably a non-doped layer and is preferably free of metal atoms.
  • the intervening layer includes an intervening layer material.
  • the intervening layer material is preferably not a light-emitting compound.
  • the intervening layer material is not particularly limited, but is preferably a material other than a light-emitting compound.
  • intervening layer material examples include 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, and 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.
  • the intervening layer material may be one or both of the first compound contained in the first light-emitting layer and the second compound contained in the second light-emitting layer.
  • the content of each of the intermediate layer materials is preferably 10 mass % or more of the total mass of the intermediate layer.
  • the intervening layer contains at least 60 mass% of the intervening layer material based on the total mass of the intervening layer, more preferably at least 70 mass% of the total mass of the intervening layer, even more preferably at least 80 mass% of the total mass of the intervening layer, even more preferably at least 90 mass% of the total mass of the intervening layer, and even more preferably at least 95 mass% of the total mass of the intervening layer.
  • the intermediate layer may contain only one type of intermediate layer material, or may contain two or more types. When the intermediate layer contains two or more types of intermediate layer materials, the upper limit of the total content of the two or more intermediate layer materials is 100 mass%. Note that this embodiment does not exclude the intermediate layer containing materials other than the intermediate layer material.
  • the intervening layer may be a single layer, or may be a laminate of two or more layers.
  • each layer is between 3 nm and 15 nm, and more preferably between 5 nm and 10 nm.
  • the organic EL element when the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer and the second light-emitting layer are stacked in the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is preferable to have a hole transport layer between the anode and the first light-emitting layer.
  • first light-emitting layer and the second light-emitting layer are stacked in the order of the second light-emitting layer and the first light-emitting layer from the anode side, it is preferable to have a hole transport layer between the anode and the second light-emitting layer.
  • the organic EL element includes a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer and the second light-emitting layer are stacked in the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is preferable to have an electron transport layer between the cathode and the second light-emitting layer.
  • first light-emitting layer and the second light-emitting layer are stacked in the order of the second light-emitting layer and the first light-emitting layer from the anode side, it is preferable to have an electron transport layer between the cathode and the first light-emitting layer.
  • the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer contains the compound according to the first embodiment (first compound). Therefore, the organic electroluminescent element according to this embodiment has improved element performance. According to one aspect of the organic electroluminescent element according to this embodiment, the life span is extended.
  • the electronic device is equipped with the organic electroluminescence element according to the above-described embodiment.
  • Examples of the electronic device include a display device and a light-emitting device.
  • Examples of the display device include a display component (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer.
  • Examples of the light-emitting device include lighting and vehicle lamps.
  • the light-emitting device can be used in a display device, for example, as a backlight for a display device.
  • the number of light-emitting layers in the organic EL element is not limited to one or two, and three or more light-emitting layers may be stacked.
  • the organic EL element has two or more light-emitting layers, it is sufficient that at least two of the light-emitting layers (the first light-emitting layer and the second light-emitting layer) satisfy the conditions described in the above embodiment.
  • the other light-emitting layer may be a fluorescent light-emitting layer, or a phosphorescent light-emitting layer that utilizes light emission due to electronic transition from a triplet excited state directly to the ground state.
  • an organic EL element when an organic EL element has multiple 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 in which multiple light-emitting units are stacked with intermediate layers interposed therebetween.
  • 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.).
  • the light emitting layer and the barrier layer are preferably in contact with each other.
  • 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 1-1 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.
  • the cleaned glass substrate with transparent electrode lines was attached to a substrate holder of a vacuum deposition apparatus, and compound HA-1 was deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrodes, thereby forming a hole injection layer with a thickness of 5 nm.
  • Compound HT-1 was deposited on the hole injection layer to form a hole transport layer having a thickness of 80 nm.
  • compound EBL-1 was deposited on the hole transport layer to form an electron blocking layer having a thickness of 10 nm.
  • an electron blocking layer having a thickness of 10 nm.
  • a compound BH1-1 (first compound) and a compound BD-1 (first light-emitting compound) were co-deposited to form a light-emitting layer having a thickness of 25 nm.
  • the proportion of the compound BH1-1 in this light-emitting layer was 98 mass %, and the proportion of the compound BD-1 was 2 mass %.
  • Compound HBL-1 was deposited on the light-emitting layer to form a first electron transport layer having a thickness of 10 nm.
  • the first electron transport layer may be referred to as a hole blocking layer.
  • the compound ET-1 was evaporated to form a second electron transport layer having a thickness of 15 nm.
  • LiF was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
  • Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 80 nm.
  • an organic EL element according to Example 1-1 was produced.
  • the device configuration of the organic EL element according to Example 1-1 is roughly shown as follows.
  • Example 1-2 to 1-10 The organic EL elements of Examples 1-2 to 1-10 were prepared in the same manner as the organic EL element of Example 1-1, except that the first compound (compound BH1-1) used in forming the light-emitting layer was changed to the first compound shown in Table 1.
  • Comparative Example 1-1 The organic EL element of Comparative Example 1-1 was prepared in the same manner as the organic EL element of Example 1-1, except that the first compound (compound BH1-1) used in forming the light-emitting layer was changed to the comparative compound shown in Table 1.
  • the light-emitting region includes one light-emitting layer.
  • the organic EL elements of Examples 1-1 to 1-10 include a compound represented by general formula (1) as the host material of the light-emitting layer, and have a longer life than the organic EL element of Comparative Example 1-1.
  • Example 2-1 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.
  • the cleaned glass substrate with transparent electrode lines was attached to a substrate holder of a vacuum deposition apparatus, and compound HA-1 was deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrodes, thereby forming a hole injection layer with a thickness of 5 nm.
  • Compound HT-1 was deposited on the hole injection layer to form a hole transport layer having a thickness of 80 nm.
  • compound EBL-1 was deposited on the hole transport layer to form an electron blocking layer having a thickness of 10 nm.
  • compound BH1-1 (first compound) and compound BD-1 (first luminescent compound) were co-deposited to form a first luminescent layer having a thickness of 5 nm.
  • the proportion of compound BH1-1 in this first luminescent layer was 98 mass %, and the proportion of compound BD-1 was 2 mass %.
  • the compound BH2 (second compound) and the compound BD-1 (second luminescent compound) were co-deposited to form a second emitting layer having a thickness of 20 nm.
  • the proportion of the compound BH2 in this second emitting layer was 98 mass %, and the proportion of the compound BD-1 was 2 mass %.
  • the compound HBL-1 was evaporated to form a first electron transport layer having a thickness of 10 nm.
  • the first electron transport layer may be referred to as a hole blocking layer.
  • the compound ET-1 was evaporated to form a second electron transport layer having a thickness of 15 nm.
  • Example 2-1 LiF was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
  • Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 80 nm.
  • an organic EL element according to Example 2-1 was produced.
  • the device configuration of the organic EL element according to Example 2-1 is roughly shown as follows. ITO(130)/HA-1(5)/HT-1(80)/EBL-1(10)/BH1-1:BD-1(5,98%:2%)/BH2:BD-1(20,98%:2%)/HBL-1(10)/ET-1(15)/LiF(1)/Al(80)
  • the numbers in parentheses indicate film thickness (unit: nm).
  • the numbers expressed as percentages (98%:2%) in parentheses indicate the ratios (mass %) of the first compound (compound BH1-1) or the second compound (BH2), and the light-emitting compound (compound BD-1) in the first light-emitting layer or the second light-emitting layer.
  • Example 2-2 to 2-10 The organic EL elements of Examples 2-2 to 2-10 were prepared in the same manner as the organic EL element of Example 2-1, except that the first compound (compound BH1-1) used in forming the light-emitting layer was changed to the first compound shown in Table 2.
  • Comparative Example 2-1 The organic EL element of Comparative Example 2-1 was produced in the same manner as the organic EL element of Example 2-1, except that the first compound (compound BH1-1) used in forming the first emitting layer was changed to a comparative compound shown in Table 2.
  • the light-emitting region includes two light-emitting layers.
  • the organic EL elements of Examples 2-1 to 2-10 include a compound represented by general formula (1) as the first host material of the first light-emitting layer, and have a longer life than the organic EL element of Comparative Example 2-1.
  • 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.
  • the phosphorescence was measured using a Hitachi High-Technologies Corporation F-4500 spectrofluorophotometer.
  • 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 taken 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 maximum peak wavelength ⁇ SOL of a compound was measured by the following method. A 5 ⁇ mol/L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300K). In this example, the emission spectrum was measured using a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength ⁇ SOL . The maximum peak wavelength ⁇ SOL of compound BD-1 was 452 nm.
  • 1-(pyren-1-yl)naphthalen-2-yl trifluoromethanesulfonate (10.7 g), 2-(2'-chloro-[1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (intermediate M5) (6.45 g), Pd2 (dba) 3 (0.37 g), and SPhos (0.67 g) were placed in a flask, and the inside of the flask was replaced with argon gas.
  • Synthesis Example 2 Synthesis of BH1-2 Compound BH1-2 was obtained as a white solid by following the method described in Synthesis Example 1, except that 6-phenyl-pyren-1-ylboronic acid (intermediate M7) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1.
  • 6-phenyl-pyren-1-ylboronic acid intermediate M7
  • pyren-1-ylboronic acid intermediate M2
  • Synthesis Example 3 Synthesis of BH1-3
  • compound BH1-3 was obtained as a white solid by following the method described in Synthesis Example 1, except that B-benzo[b]naphtho[2,1-d]furan-7-yl-boronic acid (intermediate M8) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1.
  • B-benzo[b]naphtho[2,1-d]furan-7-yl-boronic acid intermediate M8
  • pyren-1-ylboronic acid intermediate M2
  • intermediate M11 was first synthesized using 1,4-dibromonaphthalen-2-ol (intermediate M9) and intermediate M10 as shown in the above reaction scheme.
  • compound BH1-4 was obtained as a white solid by following the method described in Synthesis Example 1, except that intermediate M11 was used instead of 1-bromonaphthalen-2-ol (intermediate M1) used in Synthesis Example 1. Mass spectrum analysis of the white solid showed that the m/e was 555 for a molecular weight of 554.69, and the white solid was identified as the target compound BH1-4.
  • DME is an abbreviation for 1,2-dimethoxyethane
  • Tf 2 O is an abbreviation for trifluoromethanesulfonic anhydride
  • PdCl 2 (Amphos) 2 is an abbreviation for bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II)
  • Pd 2 (dba) 3 is an abbreviation for tris(dibenzylideneacetone)dipalladium(0)
  • SPhos is an abbreviation for 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl
  • Pd(OAc) 2 is an abbreviation for palladium(II) acetate
  • PCy 3 is an abbreviation for tricyclohexylphosphine.
  • Synthesis Example 6 Synthesis of BH1-6 Compound BH1-6 was obtained as a white solid by following the method described in Synthesis Example 1, except that (7,7-dimethyl-7H-benzo[c]fluoren-9-yl)boronic acid (intermediate M13) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1. Mass spectrum analysis of the white solid showed that m/e was 521 for a molecular weight of 520.68, and the white solid was identified as the target compound BH1-6.
  • Synthesis Example 7 Synthesis of BH1-7 Compound BH1-7 was obtained as a white solid by following the method described in Synthesis Example 1, except that 7-[2-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl]benzo[b]naphtho[2,1-d]furan (intermediate M14) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1. As a result of performing mass spectrometry analysis on the white solid, it was found that m/e was 571 for a molecular weight of 570.69, and the white solid was identified as the target compound BH1-7.
  • Synthesis Example 8 Synthesis of BH1-8 Compound BH1-8 was obtained as a white solid by following the method described in Synthesis Example 1, except that (benzo[b]triphenylen-9-yl)boronic acid (intermediate M15) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1. As a result of performing mass spectrometry analysis on the white solid, it was found that m/e was 555 for a molecular weight of 554.69, and the white solid was identified as the target compound BH1-8.
  • 1A, 1B organic EL element, 2... substrate, 3... anode, 4... cathode, 5A... light-emitting region, 5B... first light-emitting region, 5... light-emitting layer, 51... first light-emitting layer, 52... second light-emitting layer, 6... hole transport zone, 61... hole injection layer, 62... hole transport layer, 7... electron transport zone, 71... electron transport layer, 72... electron injection layer.

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Abstract

L'invention concerne un composé représenté par la formule générale (1). R1-R14 représentent chacun indépendamment un atome d'hydrogène, un groupe aryle substitué ou non substitué ayant de 6 à 19 atomes de carbone formant un cycle, un groupe hétérocyclique substitué ou non substitué ayant de 5 à 50 atomes formant un cycle, un groupe représenté par la formule générale (12), ou similaire. Au moins l'un parmi R1-R14 est un groupe représenté par la formule générale (12). L1 représente un groupe arylène substitué ou non substitué ayant de 6 à 30 atomes de carbone formant un cycle, ou un groupe hétérocyclique divalent substitué ou non substitué ayant de 5 à 30 atomes formant un cycle. Ar1 représente un groupe pyrényle substitué ou non substitué, un groupe hétérocyclique substitué ou non substitué ayant de 5 à 30 atomes formant un cycle, ou similaire. Lorsque L1 et Ar1 représentent chacun un groupe hétérocyclique, le cycle de ces groupes hétérocycliques ne comprend ni atome d'azote ni atome de soufre.
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