WO2024195402A1 - Composé, matériau d'élément électroluminescent, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, matériau d'élément électroluminescent, élément électroluminescent organique et dispositif électronique Download PDF

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WO2024195402A1
WO2024195402A1 PCT/JP2024/006002 JP2024006002W WO2024195402A1 WO 2024195402 A1 WO2024195402 A1 WO 2024195402A1 JP 2024006002 W JP2024006002 W JP 2024006002W WO 2024195402 A1 WO2024195402 A1 WO 2024195402A1
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substituted
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圭一 安川
拓人 深見
尚人 松本
大貴 野田
秀尭 星野
和真 長尾
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出光興産株式会社
東レ株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight

Definitions

  • the present invention relates to a compound, a light-emitting element material, an organic electroluminescence element, and an electronic device.
  • organic electroluminescence element When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical laws of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Fluorescent organic EL elements that use light emission from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Therefore, studies are being conducted to improve the performance of organic EL elements. Examples of the performance of organic EL elements include brightness, emission wavelength, half-width, chromaticity, luminous efficiency, driving voltage, and lifespan.
  • organic EL elements can emit light more efficiently by utilizing triplet excitons in addition to singlet excitons.
  • highly efficient fluorescent organic EL elements using thermally activated delayed fluorescence hereinafter sometimes simply referred to as "delayed fluorescence" have been proposed and studied.
  • the TADF (thermally activated delayed fluorescence) mechanism is a mechanism that utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference ( ⁇ ST) between the singlet level and the triplet level is used.
  • Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors” edited by Adachi Chinaya, Kodansha, published on April 1, 2012, pages 261-268.
  • TADF thermally activated delayed fluorescence
  • Patent Document 1 can be cited as a document relating to organic EL elements and compounds used in organic EL elements.
  • An object of the present invention is to provide a compound that can cause an organic electroluminescence element to emit light with a long lifetime, a light-emitting element material containing the compound, an organic electroluminescence element that emits light with a long lifetime, and an electronic device equipped with the organic EL element.
  • a compound having a structure represented by general formula (1) is provided.
  • R 101 to R 111 each independently represent Hydrogen atoms, Halogen atoms, Cyano group, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A group represented by —O—(R 190 ), A group represented by —S—(R 191 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A group represented by —C( ⁇
  • R 190 to R 199 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.
  • a light-emitting device material that includes a compound according to one aspect of the present invention.
  • an electronic device is provided that is equipped with an organic electroluminescence element according to one aspect of the present invention.
  • an organic electroluminescent element to emit light with a long lifetime
  • a light-emitting element material containing the compound an organic electroluminescent element that emits light with a long lifetime
  • an electronic device equipped with the organic EL element it is possible to provide a compound that can cause an organic electroluminescent element to emit light with a long lifetime, a light-emitting element material containing the compound, an organic electroluminescent element that emits light with a long lifetime, and an electronic device equipped with the organic EL element.
  • 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. 1 is a schematic diagram of an apparatus for measuring transient PL.
  • FIG. 13 is a diagram showing an example of a decay curve of a transient PL.
  • FIG. 11 is a diagram showing the energy levels of a first compound and a second compound in an emitting layer of an example of an organic electroluminescence element according to a third embodiment of the present invention, and the relationship of energy transfer.
  • FIG. 13 is a diagram showing the energy levels of a first compound, a second compound, and a third compound in an emitting layer of an example of an organic electroluminescence element according to a fourth embodiment of the present invention, and a relationship between energy transfer.
  • any possible bonding position that is not explicitly indicated with a symbol such as "R" or "D” representing a deuterium atom is assumed to have a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, bonded to it.
  • the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound).
  • a compound having a structure in which atoms are bonded in a ring for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound.
  • the carbon contained in the substituent is not included in the number of ring carbon atoms.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • a 9,9-diphenylfluorenyl group has 13 ring carbon atoms
  • a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring.
  • the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) with a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly).
  • the number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent.
  • the "number of ring atoms" described below is the same unless otherwise specified.
  • the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5.
  • the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6.
  • the number of ring atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
  • the "carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having carbon numbers XX to YY” refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • "YY” means an integer of 2 or more.
  • the "atomic number XX to YY” in the expression “substituted or unsubstituted ZZ group having atomic number XX to YY” refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituents when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • “YY” means an integer of 2 or more.
  • 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 groups in which one or more hydrogen atoms of the "unsubstituted aryl group” in the specific example group G1A below are replaced with a substituent, and the examples of the substituted aryl group in the specific example group G1B below.
  • Unsubstituted aryl groups (specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, Benzanthryl group, A phenanthryl group, Benzophenanthryl group, A phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group,
  • Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, A meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, triphenyls
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom.
  • the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
  • the “heterocyclic groups” described herein are either monocyclic or fused ring groups.
  • the “heterocyclic group” described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B).
  • the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group"
  • the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group”.
  • substituted heterocyclic group refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are merely examples, and the “substituted heterocyclic group” described in this specification also includes the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.
  • Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
  • Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, A pyrimidinyl group, Pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, A quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl
  • Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
  • Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): A thienyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, Benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanap
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2 , provided that at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from the NH or CH2 .
  • Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): A (9-phenyl)carbazolyl group, A (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, A phenylcarbazol-9-yl group, methylbenzimidazolyl group, Ethyl benzimidazolyl group, phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
  • Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, The t-butyldibenzofuranyl group, and the monovalent radical of spiro[9H-xanthene-9,9'-[9H]fluorene].
  • Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, The t-butyldibenzothiophenyl group, and the monovalent radical of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
  • one or more hydrogen atoms of a monovalent heterocyclic group means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH2 .
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B).
  • the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group"
  • the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group” is a "substituted alkyl group”.
  • substituted alkyl group refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group” are replaced with a substituent.
  • specific examples of the "substituted alkyl group” include the following "unsubstituted alkyl group” (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B).
  • the alkyl group in the "unsubstituted alkyl group” refers to a chain-like alkyl group.
  • the "unsubstituted alkyl group” includes a straight-chain “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the "substituted alkyl group” described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent.
  • Unsubstituted alkyl groups (specific example group G3A): Methyl group, Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-Butyl group, and t-butyl group.
  • Substituted alkyl groups (specific example group G3B): Heptafluoropropyl group (including isomers), pentafluoroethyl group, A 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
  • Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B).
  • the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group” is an "unsubstituted alkenyl group", and the "substituted alkenyl group” refers to the case where the "substituted or unsubstituted alkenyl group” is a "substituted alkenyl group”.
  • alkenyl group when the term “alkenyl group” is simply used, it includes both an "unsubstituted alkenyl group” and a "substituted alkenyl group”.
  • substituted alkenyl group refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include the following "unsubstituted alkenyl group” (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B).
  • the examples of the "unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” listed here are merely examples, and the "substituted alkenyl group” described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent.
  • Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, A 2-butenyl group, and a 3-butenyl group.
  • Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
  • the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group."
  • alkynyl group when simply referring to an "alkynyl group,” it includes both an "unsubstituted alkynyl group” and a “substituted alkynyl group.”
  • substituted 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:
  • dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
  • the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group".
  • Specific examples of the "substituted or unsubstituted arylene group” include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in specific example group G1.
  • Substituted or unsubstituted divalent heterocyclic group The "substituted or unsubstituted divalent heterocyclic group" described in this specification 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 (specific example group G13) 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 when “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 element or a nitrogen element
  • a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below.
  • the ring formed is a heterocycle.
  • the "one or more arbitrary elements" constituting the single ring or the condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.
  • the "monocyclic ring” and the “condensed ring” are preferred.
  • the "saturated ring” and the “unsaturated ring” are preferred.
  • a “monocyclic ring” is preferably a benzene ring.
  • the "unsaturated ring” is preferably a benzene ring.
  • one or more of a set 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 of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring” consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.
  • the substituent is, for example, the “optional substituent” described later.
  • specific examples of the substituent are the substituents described in the above-mentioned section “Substituents described in this specification”.
  • the substituent is, for example, the "optional substituent” described later.
  • substituents in the case of "substituted or unsubstituted” are, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a group selected from the group consisting of an unsubstituted
  • the two or more R 901 are the same or different from each other
  • the two or more R 902 are present, the two or more R 902 are the same or different from each other
  • the two or more R 903 are present, the two or more R 903 are the same or different from each other
  • the two or more R 904 are present, the two or more R 904 are the same or different from each other
  • the two or more R 905 are present, the two or more R 905 are the same or different from each other
  • two or more R 906 are present, the two or more R 906 are the same or different from each other
  • the two or more R 907 are present, the two or more R 907 are the same or different.
  • the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 50 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 18 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.
  • the optional substituent may further have a substituent.
  • the substituent that the optional substituent further has is the same as the optional substituent described above.
  • a mathematical expression expressed as "A ⁇ B” means that the value of A is equal to the value of B, or the value of A is greater than the value of B.
  • a mathematical expression expressed as "A ⁇ B” means that the value of A is equal to the value of B, or the value of A is smaller than the value of B.
  • the compound according to the first embodiment is a compound having a structure represented by the following general formula (1):
  • the compound according to the first embodiment may be referred to as a first compound.
  • R 101 to R 111 each independently represent Hydrogen atoms, Halogen atoms, Cyano group, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A group represented by —O—(R 190 ), A group represented by —S—(R 191 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A group represented by —C( ⁇
  • R 190 to R 199 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 190 when there are a plurality of R 190 , the plurality of R 190 are mutually identical or different, when there are a plurality of R 191 , the plurality of R 191 are mutually identical or different, when there are a plurality of R 192 , the plurality of R 192 are mutually identical or different, when there are a plurality of R 193 , the plurality of R 193 are mutually identical or different, when there are a plurality of R 194 , the plurality of R 194 are mutually identical or different, when there are a plurality of R 195 , the plurality of R 195 are mutually identical or different, when there are a plurality of R 196 , the plurality of R 196 are mutually identical or different, when there are a plurality of R 197 , the plurality of R 197 are mutually identical or different, when there are a plurality of R 198 , the plurality of R 198 are mutually identical or
  • the compounds according to the first embodiment can cause an organic electroluminescence element to emit light with a long life. Furthermore, among the compounds according to the first embodiment, compounds having a specific structure (e.g., a compound having only one cyano group as a substituent) can cause an organic electroluminescence element to emit light with an efficiency equal to or greater than that of conventional technology and with a long life.
  • compounds having a specific structure e.g., a compound having only one cyano group as a substituent
  • the compound according to the first embodiment has a cyano group at the (i), (ii) or (iii) position in the molecule, and therefore has a deep ionization potential.
  • the efficiency of energy transfer from the delayed fluorescent light-emitting material to the compound according to the first embodiment is improved.
  • the compound having the specific structure can cause an organic EL element to emit light with an efficiency equal to or greater than that of conventional technology.
  • At least one of R 108 , R 109 , R 110 and R 111 is preferably selected from substituents other than a hydrogen atom.
  • At least one of R 108 , R 109 , R 110 and R 111 is preferably selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R 110 is preferably selected from substituents other than a hydrogen atom.
  • R 110 is preferably selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • the compound represented by general formula (1) is represented by the following general formula (1A) when L 1 is a single bond, by the following general formula (1B) when L 1 is -O-, by the following general formula (1C) when L 1 is -S-, by the following general formula (1D) when L 1 is >C(R 112 )(R 113 ), and by the following general formula (1E) when L 1 is >Si(R 114 )(R 115 ).
  • R 101 to R 111 , R 112 to R 115 , ring A 1 , ring B 1 and ring C 1 are respectively defined as R 101 to R 111 , R 112 to R 115 , ring A 1 , ring B 1 and ring C 1 in the general formula (1).
  • L 1 is preferably a single bond.
  • the compound according to this embodiment is preferably represented by the general formula (1A).
  • the compound according to this embodiment preferably contains at least one substituted or unsubstituted carbazolyl group in the molecule.
  • the compound according to this embodiment preferably contains at least one substituted or unsubstituted N-carbazolyl group in the molecule.
  • At least any one of rings A 1 , ring B 1 and ring C 1 preferably has at least one substituted or unsubstituted carbazolyl group.
  • At least any one of rings A 1 , ring B 1 and ring C 1 preferably has at least one substituted or unsubstituted N-carbazolyl group.
  • ring C1 has at least one substituted or unsubstituted carbazolyl group.
  • ring C1 has at least one substituted or unsubstituted N-carbazolyl group.
  • At least one of rings A 1 , ring B 1 and ring C 1 preferably has a group represented by the following general formula (10).
  • R 151 to R 158 each independently represent Hydrogen atoms, Halogen atoms, Cyano group, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A group represented by —O—(R 190 ), A group represented by —S—(R 191 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A group represented by —C(
  • the substituted or unsubstituted N-carbazolyl group possessed by at least any one of ring A 1 , ring B 1 and ring C 1 is bonded to ring A 1 , ring B 1 and ring C 1 as a group represented by the general formula (10).
  • m in the general formula (10) is preferably 0 or 1.
  • ring B1 and ring C1 are each independently a ring represented by any one of the following general formulae (1-1) to (1-5).
  • R 121 is 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, selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
  • a pair consisting of R 122 and R 123 is connected via a single bond, —O—, —S—, >C(R 112 )(R 113 ), >Si(R 114 )(R 115 ), a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent
  • R 112 to R 115 respectively have the same definitions as R 112 to R 115 in the general formula (1).
  • the 6-membered ring shown in the general formulae (1-1) to (1-5) is condensed as ring B1 or ring C1 to the structure represented by the general formula (1).
  • ring B1 and ring C1 are each independently a ring represented by the general formula (1-1).
  • n in the general formula (1-1) is preferably 0.
  • one of ring B1 and ring C1 is a ring represented by the general formula (1-1), and the other of ring B1 and ring C1 is a ring represented by the general formula (1-2), (1-3), (1-4) or (1-5).
  • one of ring B1 and ring C1 is a ring represented by the general formula (1-1) and the other of ring B1 and ring C1 is a ring represented by either general formula (1-2) or (1-3).
  • ring A1 is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 ring carbon atoms, even more preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 ring carbon atoms, and still more preferably a substituted or unsubstituted benzene ring.
  • the compound according to this embodiment is also preferably represented by the following general formula (11):
  • R 101 to R 111 and L 1 are respectively defined as R 101 to R 111 and L 1 in the general formula (1)
  • R 131 to R 140 each independently represent Hydrogen atoms, Halogen atoms, Cyano group, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A group represented by —O—(R 190 ), A group represented by —S—(R 191 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or
  • the compound according to this embodiment is also preferably represented by the following general formula (111):
  • R 101 to R 111 are respectively defined as R 101 to R 111 in the general formula (1), and R 131 to R 140 are respectively defined as R 134 to R 140 in the general formula ( 11 ).
  • At least one of R 131 to R 140 is preferably a substituted or unsubstituted carbazolyl group, and more preferably a substituted or unsubstituted N-carbazolyl group.
  • At least one of R 134 to R 137 is preferably a substituted or unsubstituted carbazolyl group, and more preferably a substituted or unsubstituted N-carbazolyl group.
  • At least one of R 134 to R 140 is a cyano group, and it is more preferable that at least one of R 138 to R 140 is a cyano group.
  • the compound according to this embodiment is also preferably represented by the following general formula (12):
  • R 101 to R 111 and L 1 are respectively defined as R 101 to R 111 and L 1 in the general formula (1), X 1 is -O-, -S-, >N(R 121 ) or >C(R 122 )(R 123 ); R 121 has the same meaning as R 121 in formula (1-4). R 122 and R 123 are the same as R 122 and R 123 in formula (1-5), respectively.
  • R 161 to R 172 each independently represent Hydrogen atoms, Halogen atoms, Cyano group, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A group represented by —O—(R 190 ), A group represented by —S—(R 191 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A group represented by —C( ⁇ O)—O—
  • the compound according to this embodiment is also preferably represented by the following general formula (121):
  • R 101 to R 111 are the same as R 101 to R 111 in the general formula (1), respectively.
  • X 1 and R 161 to R 172 are respectively defined as X 1 and R 161 to R 172 in the general formula (12).
  • R 101 to R 109 and R 111 are preferably hydrogen atoms.
  • R 101 to R 108 , R 110 and R 111 are preferably hydrogen atoms.
  • the compound according to this embodiment preferably has at least one substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound according to this embodiment preferably has at least one substituted or unsubstituted tertiary butyl group.
  • At least one of R to R 111 , the substituent on ring B 1 , and the substituent on ring C 1 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a substituted or unsubstituted tertiary butyl group.
  • At least one of R 108 to R 111 and R 134 to R 140 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a substituted or unsubstituted tertiary butyl group.
  • R 108 to R 111 and R 164 to R 172 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a substituted or unsubstituted tertiary butyl group.
  • the compound according to this embodiment preferably has one cyano group.
  • one of R 108 to R 111 is a cyano group, or one of ring B1 and ring C1 is substituted with one cyano group.
  • R 109 is a cyano group. It is more preferable that R 109 is a cyano group, and R 108 , R 110 and R 111 are hydrogen atoms.
  • R 138 to R 140 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a substituted or unsubstituted tertiary butyl group.
  • R 139 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a substituted or unsubstituted tertiary butyl group.
  • R 139 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R 138 and R 140 are hydrogen atoms.
  • R 139 is a substituted or unsubstituted tertiary butyl group, and R 138 and R 140 are hydrogen atoms.
  • R 138 to R 140 is a cyano group.
  • R 139 is a cyano group, and R 138 and R 140 are hydrogen atoms.
  • At least one of R 108 to R 111 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a substituted or unsubstituted tertiary butyl group.
  • R 110 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a substituted or unsubstituted tertiary butyl group.
  • R 110 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R 108 , R 109 and R 111 are each a hydrogen atom.
  • R 110 is a substituted or unsubstituted tertiary butyl group, and R 108 , R 109 and R 111 are each a hydrogen atom.
  • R 110 is a substituted or unsubstituted tertiary butyl group
  • R 139 is a cyano group
  • R 110 is a substituted or unsubstituted tertiary butyl group
  • R 135 is a substituted or unsubstituted N-carbazolyl group
  • R 139 is a cyano group.
  • R 109 is a cyano group and R 139 is a substituted or unsubstituted tertiary butyl group.
  • R 109 is a cyano group
  • R 135 is a substituted or unsubstituted N-carbazolyl group
  • R 139 is a substituted or unsubstituted tertiary butyl group.
  • R 164 to R 166 is a cyano group.
  • R 165 is a cyano group, and R 164 and R 166 are hydrogen atoms.
  • R 110 is a substituted or unsubstituted tertiary butyl group
  • R 165 is a cyano group
  • R 169 to R 172 is a cyano group.
  • R 171 is a cyano group
  • R 169 , R 170 and R 172 are hydrogen atoms.
  • R 110 is a substituted or unsubstituted tertiary butyl group
  • R 171 is a cyano group
  • a cycloalkenyl group having 3 to 50 ring carbon atoms means a monovalent monocyclic group having 3 to 50 ring carbon atoms, which has at least one double bond in the ring but does not have aromaticity.
  • the number of ring carbon atoms of the cycloalkenyl group described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.
  • Specific examples of cycloalkenyl groups described in this specification include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
  • a cycloalkenylene group having 3 to 50 ring carbon atoms is a divalent group derived by removing one hydrogen atom on the cycloalkene ring from a cycloalkenyl group having 3 to 50 ring carbon atoms.
  • Specific examples of cycloalkenylene groups having 3 to 50 ring carbon atoms include divalent groups derived by removing one hydrogen atom on the cycloalkene ring from specific examples of cycloalkenyl groups having 3 to 50 ring carbon atoms.
  • the substituents in the case of "substituted or unsubstituted” are 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, an unsubstituted cycloalkenyl 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 ); Halogen atoms, cyano groups, nitro groups, It is preferably a group selected from the group consisting
  • R 901 to 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, It is 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 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 "substituted or unsubstituted" case is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the "substituted or unsubstituted" case is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.
  • unsubstituted means that a hydrogen atom is bonded.
  • the compound according to this embodiment (first compound) can be produced according to the synthesis method described in the Examples below, or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target product.
  • Specific examples of the compound (first 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.
  • a methyl group may be represented as Me
  • a phenyl group may be represented as Ph.
  • the maximum peak wavelength of the compound according to the first embodiment is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 550 nm or less, and more preferably 515 nm or more and 540 nm or less.
  • the compound having the structure represented by the general formula (1) preferably emits green light.
  • green light refers to light having a maximum peak wavelength in the fluorescence spectrum in the range of 500 nm to 560 nm.
  • the method for measuring the maximum peak wavelength of a compound is as follows.
  • a toluene solution in which the compound to be measured is dissolved at a concentration of 10 ⁇ 6 mol/L or more and 10 ⁇ 5 mol/L or less is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample (toluene solution) is measured at room temperature (300K) using a spectrofluorophotometer.
  • the emission spectrum can be measured, for example, 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.
  • the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the maximum peak wavelength.
  • the maximum peak wavelength of the fluorescent emission may be referred to as the maximum fluorescent emission peak wavelength.
  • the emission spectrum half width FWHM is the full width at half maximum at the maximum peak of the emission spectrum.
  • the light-emitting device material according to this embodiment contains the compound according to the first embodiment.
  • the light-emitting device material represents a material used in any layer of the light-emitting device.
  • One aspect of the light-emitting device material includes a light-emitting device material containing only the compound according to the first embodiment, and another aspect of the light-emitting device material includes a light-emitting device material containing the compound according to the first embodiment and another compound different from the compound in the first embodiment.
  • the compound according to the first embodiment (the compound represented by the general formula (1)) is preferably a dopant material.
  • the light-emitting device material may contain the compound according to the first embodiment as a dopant material and other compounds such as a host material.
  • an organic EL element will be described as a light emitting element.
  • the organic EL element according to this embodiment has a cathode, an anode, and an organic layer between the cathode and the anode.
  • the organic layer includes at least one layer made of an organic compound.
  • the organic layer is formed by stacking a plurality of layers made of an organic compound.
  • the organic layer may further include an inorganic compound. At least one layer of the organic layer includes the compound according to the first embodiment (first compound).
  • one aspect of the organic EL element according to this embodiment has a cathode, an anode, and an organic layer between the cathode and the anode, and at least one layer of the organic layer contains the compound according to the first embodiment as a first compound.
  • the organic layer may be composed of, for example, one light-emitting layer, or may include a layer that can be used in an organic EL element.
  • the layers that can be used in an organic EL element are not particularly limited, but may include, for example, 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, and a barrier layer.
  • FIG. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment.
  • the organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
  • the organic layer 10 is configured by laminating a hole injection layer 6, a hole transport layer 7, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side.
  • the organic layer preferably includes a light-emitting layer, and the light-emitting layer preferably includes the compound according to the first embodiment (first compound).
  • the light-emitting layer further contains a delayed fluorescent light-emitting material.
  • the light-emitting layer preferably contains a first compound and a second compound.
  • the first compound in the light-emitting layer is preferably the compound according to the first embodiment.
  • the second compound is preferably a host material (sometimes referred to as a matrix material), and the first compound is preferably a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material).
  • the "host material” refers to a material that is contained in, for example, "50% by weight or more of the layer”.
  • the light-emitting layer contains the second compound in an amount of 50% by weight or more of the total weight of the light-emitting layer.
  • the "host material” may be contained in an amount of 60% by weight or more of the layer, 70% by weight or more of the layer, 80% by weight or more of the layer, 90% by weight or more of the layer, or 95% by weight or more of the layer.
  • the compound according to the first embodiment as the first compound mainly emits light in the light-emitting layer.
  • the light-emitting layer may include a metal complex. In one embodiment, it is also preferable that the light-emitting layer does not contain a metal complex. In one embodiment, it is preferable that the light-emitting layer does not contain a phosphorescent material (dopant material). In one embodiment, the light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of the heavy metal complex include an iridium complex, an osmium complex, and a platinum complex.
  • the light-emitting layer when the light-emitting layer contains the compound according to the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.
  • the first compound is preferably the compound according to the first embodiment.
  • the first compound is a fluorescent compound that does not exhibit delayed fluorescence.
  • the second compound is not particularly limited, but it is preferable that the second compound is a delayed fluorescent light-emitting material.
  • the delayed fluorescent light-emitting material as the second compound is preferably a host material.
  • the delayed fluorescent light-emitting material as the second compound is a host material
  • the compound according to the first embodiment as the first compound is a dopant material.
  • Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that document, it is explained that if the energy difference ⁇ E 13 between the excited singlet state and the excited triplet state of the fluorescent material can be reduced, the reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state occurs with high efficiency, and thermally activated delayed fluorescence (TADF) is expressed. Furthermore, in FIG. 10.38 in that document, the mechanism of delayed fluorescence generation is explained.
  • the delayed fluorescent light-emitting material in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.
  • delayed fluorescence emission can be confirmed by transient PL (photoluminescence) measurement.
  • delayed fluorescence is emitted from singlet excitons generated via triplet excitons, which have a long life span, and therefore decays slowly.
  • the emission intensity derived from delayed fluorescence can be obtained.
  • Figure 2 shows a schematic diagram of an exemplary device for measuring transient PL. We will explain a method for measuring transient PL using Figure 2 and an example of behavior analysis of delayed fluorescence.
  • the transient PL measurement device 100 in FIG. 2 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image.
  • a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength
  • a sample chamber 102 for accommodating a measurement sample
  • a spectroscope 103 for dispersing the light emitted from the measurement sample
  • a streak camera 104 for forming a two-dimensional image
  • personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in FIG. 2.
  • the sample contained in the sample chamber 102 is obtained by forming a thin film of a matrix material doped with a doping material at a concentration of 12% by mass on a quartz substrate.
  • a pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed in the sample chamber 102 to excite the doping material.
  • Emission light is extracted in a direction at 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by the spectroscope 103, and a two-dimensional image is formed in the streak camera 104.
  • a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity.
  • By cutting out this two-dimensional image on a specified time axis it is possible to obtain an emission spectrum in which the vertical axis is emission intensity and the horizontal axis is wavelength.
  • a decay curve (transient PL) in which the vertical axis is the logarithm of emission intensity and the horizontal axis is time.
  • the following compound HX1 was used as the matrix material, and the following compound DX1 was used as the doping material to prepare thin film sample A as described above, and transient PL measurements were performed.
  • Thin film sample B was prepared as described above using the following compound HX2 as the matrix material and the aforementioned compound DX1 as the doping material.
  • Figure 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.
  • transient PL measurement it is possible to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, it is possible to estimate the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state.
  • the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly is relatively large.
  • Prompt emission is emission that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength that the delayed fluorescent material absorbs.
  • Delay emission is emission that is not observed immediately after excitation by the pulsed light, but is observed at a later time.
  • the amount and ratio of prompt light emission and delay light emission can be calculated by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of prompt light emission and delay light emission is not limited to the device described in Reference 1 or the device shown in FIG. 2.
  • the delayed fluorescence of the delayed fluorescent material is measured using a sample prepared by the following method.
  • the delayed fluorescent material is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption.
  • the sample solution is frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.
  • the fluorescence spectrum of the sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions.
  • the total fluorescence quantum yield is calculated using the fluorescence area intensities of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.
  • the amount of prompt luminescence (immediate luminescence) of the measurement target compound (delayed fluorescent material) is XP and the amount of delay luminescence (delayed luminescence) is XD , it is preferable that the value of XD / XP is 0.05 or more.
  • the amounts and ratio of prompt luminescence and delay luminescence of compounds other than delayed fluorescent luminescent materials in this specification are measured in the same manner as the amounts and ratio of prompt luminescence and delay luminescence of delayed fluorescent luminescent materials.
  • the difference ⁇ ST(M2) between the minimum excited singlet energy S 1 (M2) of the delayed fluorescent light-emitting material and the energy gap T 77K (M2) at 77 [K] of the delayed fluorescent light-emitting material is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, it is preferable that ⁇ ST(M2) satisfies the relationship of the following formula (Mathematical Formula 10), (Mathematical Formula 11), (Mathematical Formula 12), or (Mathematical Formula 13).
  • the energy gap at 77 K differs from the triplet energy that is usually defined.
  • the triplet energy is measured as follows. First, a sample is prepared by dissolving a compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube.
  • the thermally activated delayed fluorescent compound is preferably a compound with a small ⁇ ST. If ⁇ ST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), and the excited singlet state and the excited triplet state are mixed.
  • the spectrum measured in the same manner as above includes light emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish which state the light emission is from, but the triplet energy value is basically considered to be dominant. Therefore, in this embodiment, the measurement method is the same as that of the normal triplet energy T, but in order to distinguish that it is different in the strict sense, the value measured as follows is referred to as the energy gap T 77K .
  • the 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 energy amount calculated from the following conversion formula (F1) based on the wavelength value ⁇ edge [nm] of the intersection point between the tangent and the horizontal axis is defined as the energy gap T 77K at 77 [K].
  • Conversion formula (F1): T 77K [eV] 1239.85/ ⁇ edge
  • the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows.
  • the slope of this tangent increases as the curve rises (i.e., as the vertical axis increases).
  • the tangent drawn at the point where this slope is at its maximum is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side described above, and a tangent drawn at a point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is regarded as a tangent to the rising edge on the short wavelength side of the phosphorescence spectrum.
  • Phosphorescence can be measured using a spectrofluorophotometer body, Model F-4500, manufactured by Hitachi High-Technologies Corp.
  • the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.
  • the method for measuring the lowest excited singlet energy S1 using a solution includes the following method.
  • a 10 ⁇ mol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300 K).
  • a tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value ⁇ edge [nm] at the intersection of the tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the minimum excited singlet energy.
  • Conversion formula (F2): S 1 [eV] 1239.85/ ⁇ edge
  • An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.
  • the tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows.
  • the slope of this tangent decreases and then increases repeatedly.
  • the tangent drawn at the point where the slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values of 0.2 or less are not included in the maximum values on the longest wavelength side.
  • the minimum excited singlet energy S 1 (M1) of the first compound (compound according to the first embodiment) and the minimum excited singlet energy S 1 (M2) of the second compound (delayed fluorescent light-emitting material) satisfy the relationship of the following mathematical formula (Mathematical Formula 1).
  • the energy gap T 77K (M1) of the first compound at 77 [K] is preferably smaller than the energy gap T 77K (M2) of the second compound at 77 [K]. That is, it is preferable that the relationship of the following mathematical formula (Mathematical Formula 3) is satisfied. T 77K (M2)>T 77K (M1)...(Math. 3)
  • the delayed fluorescent light-emitting material as the second compound is not particularly limited as long as it is a compound having delayed fluorescence.
  • the delayed fluorescent light-emitting material as the second compound is a compound represented by the following general formula (20).
  • D X is a group represented by the following general formula (21), general formula (22) or general formula (23), provided that at least one D X is a group represented by the following general formula (22) or general formula (23): m is 1, 2, 3, or 4, and when m is 2, 3, or 4, a plurality of D X's are the same or different from each other;
  • Each R is independently Hydrogen atoms, Halogen atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, A group represented by -Si( R291 )( R292 )( R293 ), A group represented by —O—(R 294 ),
  • R 19 and R 20 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other
  • X 10 and X 20 each independently represent NR 120 , a sulfur atom, or an oxygen atom
  • R 120 , and R 19 and R 20 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring are each independently Hydrogen atoms, Halogen atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubsubstituted
  • R 291 to R 297 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 291 when there are a plurality of R 291 , the plurality of R 291 are mutually identical or different, when there are a plurality of R 292 , the plurality of R 292 are mutually identical or different, when there are a plurality of R 293 , the plurality of R 293 are mutually identical or different, when there are a plurality of R 294 , the plurality of R 294 are mutually identical or different, when there are a plurality of R 295 , the plurality of R 295 are mutually identical or different, when there are a plurality of R 296 , the plurality of R 296 are mutually identical or different, and when there are a plurality of R 297 , the plurality of R 297 are mutually identical or different.
  • the benzene ring of the general formula (20) to which the groups represented by the general formulae (21), (22), and (23) are bonded is the benzene ring explicitly shown in the general formula (20) itself, and is not a benzene ring contained in R and D X.
  • At least one R is a substituent rather than a hydrogen atom or a halogen atom, and that at least one R as a substituent is bonded to the benzene ring in the general formula (20) via a carbon-carbon bond.
  • the sum of the number of R substituents and the number of groups represented by the general formula (22) or (23) is 3 or 4.
  • each R is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms.
  • R 1 to R 8 , R 11 to R 18 and R 111 to R 118 each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms.
  • p is preferably 2, 3 or 4.
  • px and py each independently preferably represent 2, 3, or 4.
  • the delayed fluorescent light-emitting material can be produced by a known method.
  • the delayed fluorescent light-emitting material can also be produced by following a known method and using known alternative reactions and raw materials suited to the intended product.
  • Specific examples of the delayed fluorescent light-emitting material include the following compounds: However, the present invention is not limited to these specific examples of the delayed fluorescent light-emitting material.
  • (TADF Mechanism) 4 is a diagram showing an example of the relationship between the energy levels of the second compound M2 in the case of a delayed fluorescent light-emitting material in the light-emitting layer and the first compound M1 in the case of the compound of the first embodiment.
  • S0 represents the ground state.
  • S1(M1) represents the lowest excited singlet state of the first compound M1.
  • T1(M1) represents the lowest excited triplet state of the first compound M1.
  • S1(M2) represents the lowest excited singlet state of the second compound M2.
  • T1(M2) represents the lowest excited triplet state of the second compound M2.
  • the second compound as the host material may be a compound having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the first compound as the dopant material.
  • the host material include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives, (3) condensed aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives, (3) condensed heterocyclic compounds such as carbazole derivatives, and (4) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.
  • the organic EL element of the present embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in the light-emitting layer.
  • the organic EL element of this embodiment preferably emits green light.
  • the maximum peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less.
  • the maximum peak wavelength of the light emitted from the organic EL element is measured as follows. A voltage is applied to the organic EL element so that the current density 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 at which the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).
  • the thickness of the light-emitting layer in the organic EL element of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm.
  • the thickness of the light-emitting layer is 5 nm or more, the formation of the light-emitting layer and the adjustment of the chromaticity are easily facilitated.
  • the thickness of the light-emitting layer is 50 nm or less, an increase in the driving voltage is easily suppressed.
  • the contents of the first compound and the second compound contained in the light-emitting layer are preferably within the following ranges, for example.
  • the content of the first compound is preferably from 0.01% by mass to 10% by mass, more preferably from 0.01% by mass to 5% by mass, and further preferably from 0.01% by mass to 1% by mass.
  • the content of the second compound is preferably from 10% by mass to 80% by mass, more preferably from 10% by mass to 60% by mass, and further preferably from 20% by mass to 60% by mass.
  • the upper limit of the total content of the first compound and the second compound in the light-emitting layer is 100 mass %.
  • the light-emitting layer contains materials other than the first compound and the second compound.
  • the light-emitting layer may contain only one type of the first compound or two or more types of the second compound.
  • the light-emitting layer may contain only one type of the second compound or two or more types of the second compound.
  • 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.
  • metal materials e.g., titanium nitride
  • 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), and the like.
  • metal materials e.g., titanium nitride
  • indium oxide-zinc oxide can be formed by a sputtering method using a target in which zinc oxide is added to indium oxide at 1 mass % or more and 10 mass % or less.
  • indium oxide containing tungsten oxide and zinc oxide can be formed by a sputtering method using a target in which tungsten oxide is added to indium oxide at 0.5 mass % or more and 5 mass % or less and zinc oxide is added to indium oxide.
  • the film may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method, or the like.
  • the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, and therefore materials that can be used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, as well as other elements belonging to Group 1 or Group 2 of the periodic table) can be used.
  • electrode materials e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, as well as other elements belonging to Group 1 or Group 2 of the periodic table
  • 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 europium (Eu), ytterbium (Yb), and alloys containing these
  • a vacuum deposition method or a sputtering method can be used.
  • a coating method or an inkjet method can be used.
  • the anode is preferably formed of a metal material that is optically transparent or semi-transparent, and transmits light from the light-emitting layer.
  • optically transparent or semi-transparent means a property that transmits 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer.
  • the optically transparent or semi-transparent metal material can be appropriately selected from the materials listed in the anode section above.
  • the anode is a reflective electrode having a reflective layer.
  • the reflective layer is preferably formed of a metal material having light reflectivity.
  • light reflectivity means a property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light emitting layer.
  • the metal material having light reflectivity can be appropriately selected from the materials listed in the above section on the anode.
  • the anode may be composed of only a reflective layer, but may also have a multi-layer structure having a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is disposed between the reflective layer and the hole transport zone.
  • the conductive layer can be appropriately selected from the materials listed in the above section on the anode.
  • cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a small work function (specifically, 3.8 eV or less).
  • a cathode material include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such
  • the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.
  • the cathode is a reflective electrode.
  • the reflective electrode is preferably formed from a metal material having optical reflectivity.
  • the metal material having optical reflectivity can be appropriately selected from the materials listed in the cathode section.
  • the cathode is preferably formed from a metal material that is optically transparent or semi-transparent and transmits light from the light-emitting layer.
  • the optically transparent or semi-transparent metal material can be appropriately selected from the materials listed in the cathode section above.
  • the organic EL element according to this embodiment may be a bottom-emission type organic EL element, or a top-emission type organic EL element.
  • the organic EL element is of a bottom emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflection.
  • the organic EL element is of a top emission type, it is preferable that the anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmittance.
  • the organic EL element When the organic EL element is a top emission type, the organic EL element usually has a capping layer on the upper part of the cathode.
  • the capping layer may contain at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (silicon oxide, etc.).
  • the capping layer may also contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives.
  • a laminate in which layers containing these substances are laminated can also be used as the capping layer.
  • the hole injection layer is a layer containing a substance having a high hole injection property, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or the like.
  • a substance having a high hole injection property such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or the like.
  • examples of the material with high hole injection properties include low molecular weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N- ⁇ 4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl ⁇ -N-phenylamino)biphenyl (abbreviation: DNTPD), 1,
  • aromatic amine compounds include 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation:
  • a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used.
  • polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino ⁇ phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]
  • a polymer compound to which an acid is added such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) or polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can also be used.
  • PEDOT/PSS poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid)
  • PAni/PSS polyaniline/poly(styrenesulfonic acid)
  • the hole transport layer is a layer containing a substance with high hole transport properties.
  • an aromatic amine compound a carbazole derivative, an anthracene derivative, or the like can be used.
  • NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • TPD N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine
  • TPD N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine
  • BAFLP 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine
  • BAFLP 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]bipheny
  • aromatic amine compounds examples include aromatic amine compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB).
  • TDATA 4,4',4''-tris(N,N-diphenylamino)triphenylamine
  • MTDATA 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine
  • BSPB 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyla
  • carbazole derivatives such as CBP, CzPA, and PCzPA
  • anthracene derivatives such as t-BuDNA, DNA, and DPAnth
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • other substances may be used as long as they have a higher hole transporting property than electron transporting property.
  • the layer containing the substance having a high hole transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned substances are stacked.
  • the electron transport layer is a layer containing a substance with high electron transport properties.
  • a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex
  • a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound can be used.
  • a metal complex such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), BAlq, Znq, ZnPBO, or ZnBTZ can be used.
  • the substances described here are mainly substances having an electron mobility of 10 -6 cm 2 /Vs or more. Note that substances other than the above may be used as the electron transport layer as long as they have a higher electron transport property than a hole transport property.
  • the electron transport layer may be a single layer or a layer in which two or more layers made of the above substances are stacked.
  • the electron transport layer may also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).
  • PF-Py poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)]
  • PF-BPy poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)]
  • the electron injection layer is a layer containing a substance with high electron injection properties.
  • alkali metals, alkaline earth metals, or compounds thereof such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), and lithium oxide (LiOx), can be used.
  • a substance having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) in Alq, etc. can be used. In this case, electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) can be used for the electron injection layer.
  • a composite material has excellent electron injection properties 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 substance constituting the electron transport layer (metal complex, heteroaromatic compound, 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, including lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferred, including lithium oxide, calcium oxide, and barium oxide.
  • Lewis bases such as magnesium oxide can also be used.
  • organic compounds 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.
  • the film thickness of each organic layer in the organic EL element of the present embodiment is not limited except as specifically mentioned above. In general, however, if the film thickness is too thin, defects such as pinholes are likely to occur, whereas if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness is usually preferably in the range of several nm to 1 ⁇ m.
  • At least one of the organic layers contains the compound of the first embodiment, and thus a high-performance organic EL element is realized.
  • an organic EL element that emits light with a long life is realized.
  • an organic EL element that emits light with efficiency equal to or greater than that of conventional technology and with a long life is realized.
  • the organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • Organic electroluminescence element The configuration of the organic EL element according to the fourth embodiment will be described.
  • the same components as those in the third embodiment will be given the same reference numerals or names, and the description will be omitted or simplified.
  • the same materials and compounds as those described in the third embodiment can be used.
  • 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 layer further contains a third compound. In other respects, it is the same as the organic EL element according to the third embodiment.
  • the light-emitting layer preferably includes a first compound, a second compound, and a third compound.
  • the first compound is the compound of the first embodiment, and it is even more preferable that the second compound is a delayed fluorescent light-emitting material.
  • the first compound is a dopant material, and it is preferable that the second compound is a host material. It is also preferable that the third compound is not a dopant material.
  • the light-emitting layer of the fourth embodiment may contain the second compound and the third compound in a total amount of 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the total mass of the light-emitting layer.
  • the third compound may be a delayed fluorescent compound or a compound that does not exhibit delayed fluorescence, but is preferably a compound that does not exhibit delayed fluorescence.
  • the third compound is not particularly limited, but is preferably a compound other than an amine compound. That is, it is preferable that the third compound does not contain a substituted or unsubstituted amino group.
  • the third compound may be a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative, but is not limited to these derivatives.
  • the third compound is also preferably a compound represented by the following general formula (3X).
  • A3 is 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
  • L3 is Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding three groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group
  • R B is 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 group represented by —C( ⁇ O)R 90
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When a plurality of R 901 are present, the plurality of R 901 are the same or different, When a plurality of R 902 are present, the plurality of R 902 are the same or different from each other, When a plurality of
  • the third compound is preferably a compound represented by any one of the following general formulas (31) to (36).
  • A3 and L3 are the same as A3 and L3 in formula (3X), respectively.
  • One or more pairs of adjacent two or more of R 341 to R 350 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • X31 is a sulfur atom, an oxygen atom, NR352 or CR353R354 ;
  • the pair consisting of R 353 and R 354 is joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, R 341 to R 350 and R 352 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring, and R 353 and R 354
  • R 352 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R 353 and R 354 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • X 31 is preferably a sulfur atom or an oxygen atom.
  • A3 is preferably a group represented by any one of the following general formulas (A31) to (A37).
  • R 300 which does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring
  • R 333 each independently have the same meaning as R 31 to R 38 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring
  • * indicates the bonding position of the third compound to L3 .
  • A3 is also preferably a group represented by the general formula (A34), (A35) or (A37).
  • the third compound is also preferably a compound represented by any one of the following general formulas (311) to (316).
  • L3 has the same meaning as L3 in formula (3X).
  • One or more of the groups of two or more adjacent R 300 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded together to form a substituted or unsubstituted fused ring, or are not bonded together,
  • One or more pairs of adjacent two or more of R 341 to R 350 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • R 341 to R 350 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring, each independently have the same meaning as R
  • the third compound is also preferably a compound represented by the following general formula (321):
  • L3 has the same meaning as L3 in formula (3X).
  • R 31 to R 38 and R 301 to R 308 each independently have the same meaning as R 31 to R 38 , which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring.
  • L 3 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
  • L3 is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.
  • L3 is preferably a group represented by the following general formula (317).
  • R 310 each independently has the same meaning as R 31 to R 38 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring, and * each independently indicates a bonding position.
  • L3 contains a divalent group represented by the following general formula (318) or general formula (319).
  • L3 is also preferably a divalent group represented by the following general formula (318) or general formula (319).
  • the third compound is also preferably a compound represented by the following general formula (322) or general formula (323).
  • the group represented by the general formula (319) as L3 or L31 is, for example, a group represented by the following general formula (319A).
  • R 303 , R 304 and R 305 each independently have the same meaning as R 31 to R 38 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring, and * in the general formula (319A) each indicates a bonding position.
  • the third compound is a compound represented by the above general formula (322), and L 31 is a group represented by the above general formula (318).
  • the third compound is also preferably a compound represented by the following general formula (324):
  • R 31 to R 38 , R 300 and R 302 each independently have the same meaning as R 31 to R 38 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring.
  • R 31 to R 38 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 aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (3A):
  • R B is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R 31 to R 38 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 group represented by general formula (3A):
  • R 3 B is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 31 to R 38 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 phenyl group, or a group represented by general formula (3A),
  • R 3 B is preferably a substituted or unsubstituted phenyl group.
  • the third compound is a compound that does not have a pyridine ring, a pyrimidine ring, or a triazine ring.
  • the third compound can be produced by a known method.
  • the third compound can also be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.
  • the lowest excited singlet energy S 1 (M2) of the second compound and the lowest excited singlet energy S 1 (M3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2).
  • the energy gap T 77K (M3) at 77 [K] of the third compound is preferably larger than the energy gap T 77K (M1) at 77 [K] of the first compound.
  • the energy gap T 77K (M3) at 77 [K] of the third compound is preferably larger than the energy gap T 77K (M2) at 77 [K] of the second compound.
  • the lowest excited singlet energy S 1 (M1) of the first compound, the lowest excited singlet energy S 1 (M2) of the second compound, and the lowest excited singlet energy S 1 (M3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2A).
  • the energy gap T 77K (M1) at 77 [K] of the first compound, the energy gap T 77K (M2) at 77 [K] of the second compound, and the energy gap T 77K (M3) at 77 [K] of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2B).
  • the contents of the first compound, the second compound, and the third compound in the light-emitting layer are preferably, for example, in the following ranges.
  • the content of the first compound in the light-emitting layer is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less.
  • the content of the second compound is preferably from 10% by mass to 80% by mass, more preferably from 10% by mass to 60% by mass, and further preferably from 20% by mass to 60% by mass.
  • the content of the third compound is preferably 10% by mass or more and 80% by mass or less.
  • the upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100 mass %. Note that this embodiment does not exclude the light-emitting layer containing materials other than the first compound, the second compound, and the third compound.
  • the light-emitting layer may contain only one type of the first compound or two or more types.
  • the light-emitting layer may contain only one type of the second compound or two or more types.
  • the light-emitting layer may contain only one type of the third compound or two or more types.
  • the organic EL element of this embodiment When the organic EL element of this embodiment is caused to emit light, it is preferable that the compound of the first embodiment mainly emits light in the light-emitting layer. When the organic EL element of the present embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in the light-emitting layer.
  • the organic EL element of this embodiment preferably emits green light, similar to the organic EL element of the third embodiment.
  • the maximum peak wavelength of the light emitted from the organic EL element can be measured in the same manner as the organic EL element of the third embodiment.
  • (TADF Mechanism) 5 is a diagram showing an example of the relationship between the energy levels of the first compound M1, the second compound M2, and the third compound M3 in the light-emitting layer.
  • S0 represents the ground state.
  • S1(M1) represents the lowest excited singlet state of the first compound M1
  • T1(M1) represents the lowest excited triplet state of the first compound M1.
  • S1(M2) represents the lowest excited singlet state of the second compound M2, and T1(M2) represents the lowest excited triplet state of the second compound M2.
  • S1(M3) represents the lowest excited singlet state of the third compound M3, and T1(M3) represents the lowest excited triplet state of the third compound M3.
  • 5 represents the Förster type energy transfer from the lowest excited singlet state of the second compound M2 to the first compound M1.
  • a compound (delayed fluorescent material) with a small ⁇ ST (M2) is used as the second compound M2
  • the lowest excited triplet state T1 (M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1 (M2) by thermal energy.
  • Förster type energy transfer occurs from the lowest excited singlet state S1 (M2) of the second compound M2 to the first compound M1, and the lowest excited singlet state S1 (M1) is generated.
  • fluorescence emission from the lowest excited singlet state S1 (M1) of the first compound M1 can be observed. It is believed that the internal quantum efficiency can be theoretically increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.
  • At least one of the organic layers contains the compound of the first embodiment, and thus a high-performance organic EL element is realized.
  • an organic EL element that emits light with a long life is realized.
  • an organic EL element that emits light with efficiency equal to or greater than that of conventional technology and with a long life is realized.
  • the organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • the electronic device is equipped with any of the organic EL elements according to the above-mentioned embodiments.
  • 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 light-emitting layer is not limited to one layer, and a plurality of light-emitting layers may be laminated.
  • the organic EL element has a plurality of light-emitting layers, it is sufficient that at least one of the organic layers satisfies the conditions described in the above embodiment, and it is preferable that at least one of the light-emitting layers contains the compound of the first embodiment.
  • the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electronic transition from a triplet excited state directly to a ground state.
  • the organic EL element has a plurality of light-emitting layers
  • these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.
  • a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer.
  • the blocking layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons.
  • the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) on the cathode side of the blocking layer.
  • the organic EL element includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer.
  • the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) on the anode side of the blocking layer.
  • a layer e.g., a hole transport layer
  • the organic EL element includes a hole transport layer
  • a barrier layer may be provided adjacent to the light-emitting layer to prevent the excitation energy from leaking from the light-emitting layer to the surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers on the electrode side of the barrier layer (e.g., the electron transport layer and the hole transport layer, etc.).
  • 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 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm ⁇ 75 mm ⁇ 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130 nm.
  • the glass substrate with the transparent electrode lines after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound HT-1 and the compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm.
  • the proportion of the compound HT-1 in the hole injection layer was 97% by mass, and the proportion of the compound HA was 3% by mass.
  • compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 90 nm.
  • the compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 30 nm.
  • the compound TADF as a delayed fluorescent light-emitting material
  • the compound GD-A as a fluorescent light-emitting material
  • the proportion of the compound HOST in the emitting layer was 74.2% by mass, the proportion of the compound TADF was 25% by mass, and the proportion of the compound GD-A was 0.8% by mass.
  • the compound ET-1 was evaporated onto the light-emitting layer to form a hole blocking layer having a thickness of 5 nm.
  • the compound ET-2 and Liq were co-deposited on the hole blocking layer to form an electron transport layer having a thickness of 50 nm.
  • the proportion of the compound ET-2 in the electron transport layer was 50 mass %, and the proportion of Liq was 50 mass %.
  • ytterbium (Yb) was evaporated onto the electron transport layer to form an electron injection layer having a thickness of 1 nm.
  • Example 1 metallic aluminum (Al) was vapor-deposited on the electron injection layer to form a metallic Al cathode having a thickness of 80 nm.
  • the device configuration of the organic EL device according to Example 1 is roughly shown as follows. ITO(130)/HT-1:HA(10,97%:3%)/HT-1(90)/HT-2(30)/HOST:TADF:GD-A(25,74.2%:25%:0.8%)/ET-1(5)/ET-2:Liq(50,50%:50%)/Yb(1)/Al(80)
  • the numbers in parentheses indicate the film thickness (unit: nm).
  • the numbers in parentheses expressed as percentages (97%:3%) indicate the ratios (mass%) of the compounds HT-1 and HA in the hole injection layer
  • the numbers in percentages (74.2%:25%:0.8%) indicate the ratios (mass%) of the compounds HOST, TADF, and GD-A in the light-emitting layer
  • the numbers in percentages (50%:50%) indicate the ratios (mass%) of the compounds ET-2 and Liq in the electron transport layer.
  • Example 2 and 3 The organic EL elements of Examples 2 and 3 were prepared in the same manner as the organic EL element of Example 1, except that the compound GD-A in the emitting layer of the organic EL element of Example 1 was changed to the first compound shown in Table 1.
  • Comparative Example 1 The organic EL element of Comparative Example 1 was prepared in the same manner as the organic EL element of Example 1, except that the compound GD-A in the emitting layer of the organic EL element of Example 1 was changed to the first compound shown in Table 1.
  • Example 4 The organic EL element of Example 4 was produced in the same manner as the organic EL element of Example 1, except that the compound GD-A in the emitting layer of the organic EL element of Example 1 was changed to the first compound described in Table 2, the proportion of the compound HOST in the emitting layer of Example 1 was 74.4 mass%, the proportion of the compound TADF was 25 mass%, and the proportion of the first compound described in Table 2 was 0.6 mass%.
  • Example 5 The organic EL element of Example 5 was produced in the same manner as the organic EL element of Example 1, except that the compound GD-A in the emitting layer of the organic EL element of Example 1 was changed to the first compound described in Table 2, the proportion of the compound HOST in the emitting layer of Example 1 was 74.4 mass%, the proportion of the compound TADF was 25 mass%, and the proportion of the first compound described in Table 2 was 0.6 mass%.
  • Comparative Example 2 The organic EL element of Comparative Example 2 was prepared in the same manner as the organic EL element of Example 4, except that the compound GD-D in the emitting layer of the organic EL element of Example 4 was changed to the first compound shown in Table 2.
  • CIE1931 chromaticity The CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the prepared organic EL element so that the current density was 10 mA/ cm2 were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). .
  • ⁇ EL and emission half width FWHM when the element is operating The spectral radiance spectrum when a voltage was applied to the prepared organic EL element so that the current density was 10 mA/ cm2 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the maximum peak wavelength ⁇ EL (unit: nm) and the emission half width FWHM (unit: nm) were obtained. FWHM is an abbreviation of full width at half maximum.
  • EQE95 (relative value) (unit: %) was calculated.
  • EQE (relative value) (EQE of each example / EQE of Comparative Example 1) x 100 ... (Equation 2X)
  • EQE (relative value) (EQE of each example / EQE of Comparative Example 2) x 100 ... (Equation 2Y)
  • the organic EL devices of Examples 1 to 3 which contain compound GD-A, compound GD-B, or compound GD-C as a compound having a structure represented by general formula (1), emitted light with higher efficiency and longer life than the organic EL device of Comparative Example 1, which uses comparative compound Ref-1.
  • the organic EL devices of Examples 4 and 5 which contain compound GD-D or compound GD-F as a compound having a structure represented by general formula (1), emitted light with a longer life than the organic EL device of Comparative Example 2, which used comparative compound Ref-1.
  • the delayed fluorescence was confirmed by measuring the transient PL using the apparatus shown in Figure 2.
  • the compound TADF was dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption.
  • the sample solution was frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.
  • the fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions.
  • the total fluorescence quantum yield was calculated using the fluorescence area intensities of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.
  • delayed fluorescence means that the amount of delay luminescence (delayed luminescence) is 5% or more relative to the amount of prompt luminescence (immediate luminescence). Specifically, when the amount of prompt luminescence (immediate luminescence) is X P and the amount of delay luminescence (delayed luminescence) is X D , the value of X D /X P is 0.05 or more.
  • the amount of Prompt luminescence and Delay luminescence and the ratio thereof can be obtained by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1).
  • the device used to calculate the amount of Prompt luminescence and Delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2.
  • the amount of Delay luminescence was 5% or more relative to the amount of Prompt luminescence.
  • the value of X D /X P was 0.05 or more.
  • intermediate A4 (93 g, 233 mmol), triphenylphosphine (153 g, 582.7 mmol), and orthodichlorobenzene (ODCB) (500 mL) were placed in a three-neck flask and heated under stirring and reflux for 12 hours.
  • the reaction liquid was concentrated and purified by silica gel column chromatography to obtain 42 g of a white solid.
  • the white solid was identified as intermediate A5 by mass spectrometry (yield 49%).
  • intermediate A3 50 g, 96 mmol
  • intermediate A5 (4.36 g, 98 mmol)
  • tripotassium phosphate 102 g, 481 mmol
  • N,N-dimethylformamide 200 mL
  • the reaction solution was cooled to room temperature
  • water was added and the precipitated solid was collected by suction filtration.
  • the resulting solid was purified by silica gel column chromatography to obtain 73 g of a pale yellow solid.
  • the pale yellow solid was identified as intermediate A6 by mass spectrometry (yield 88%).
  • intermediate A6 73 g, 84 mmol
  • t-butylbenzene 842 mL
  • sec-butyllithium solution solvent: cyclohexane and n-hexane
  • 1.2 mol/L 140 mL, 168 mmol
  • boron tribromide 24 mL, 253 mmol
  • intermediate A7 (2.4 g, 3.0 mmol), potassium hexacyanoferrate(II) (2.2 g, 6.0 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.21 g, 0.30 mmol), sodium carbonate (0.06 g, 0.6 mmol), and 1-methyl-2-pyrrolidone (60 mL) were placed in a three-neck flask and stirred at 135°C for 4 hours. The reaction solution was cooled to room temperature, and 60 mL of dichloromethane and silica gel were added and suction filtered.
  • the resulting solution was concentrated, methanol was added, and the resulting solid was purified by silica gel column chromatography to obtain 1.1 g of an orange solid.
  • the orange solid was identified as compound GD-A by mass spectrometry (yield 46%).
  • the reaction solution was cooled to room temperature, and then water and toluene were added and separated.
  • the resulting organic layer was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure.
  • the resulting residue was purified by silica gel column chromatography to obtain 3.7 g of a white solid.
  • the white solid was identified as intermediate B2 by mass spectrometry (yield 17%).
  • intermediate A3 (7.50 g, 14.4 mmol), intermediate B2 (4.20 g, 14.4 mmol), tripotassium phosphate (9.20 g, 43.2 mmol), and N,N-dimethylformamide (36.0 mL) were placed in a three-neck flask and stirred at 140°C for 21 hours. After the reaction solution was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 1.95 g of a pale yellow solid. The pale yellow solid was identified as intermediate B3 by mass spectrometry (yield 17%).
  • intermediate B3 (1.95 g, 2.50 mmol) and t-butylbenzene (25 mL) were placed in a three-neck flask and cooled to -60°C. Then, s-butyllithium solution (solvent: cyclohexane and n-hexane), 1.2 mol/L (4.10 mL, 4.90 mmol) was added dropwise, the mixture was heated to -40°C, and stirred for 30 minutes. The reaction solution was cooled to -78°C, and then boron tribromide (0.70 mL, 7.40 mmol) was added dropwise, the mixture was heated to room temperature, and stirred for 10 hours.
  • solvent cyclohexane and n-hexane
  • intermediate B4 (1.00 g, 1.40 mmol), potassium hexacyanoferrate(II) (1.00 g, 2.80 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.20 g, 0.30 mmol), sodium carbonate (0.12 g, 1.40 mmol), and 1-methyl-2-pyrrolidone (28 mL) were placed in a three-neck flask and stirred at 135°C for 5 hours. The reaction solution was cooled to room temperature, and the precipitated solid was collected by suction filtration and purified by recrystallization to obtain 0.25 g of an orange solid. The orange solid was identified as compound GD-B by mass spectrometry (yield 25%).
  • intermediate C2 88.0 g, 272 mmol
  • triphenylphosphine 178 g, 680 mmol
  • orthodichlorobenzene 543 mL
  • the reaction solution was cooled to room temperature and then concentrated under reduced pressure.
  • the resulting residue was purified by silica gel column chromatography and recrystallization to obtain 54.0 g of a white solid.
  • the white solid was identified as intermediate C3 by mass spectrometry (yield 68%).
  • intermediate B3 was carried out in the same manner, except that intermediate C3 was used instead of intermediate B2, to obtain a yellow solid (4.90 g). Mass spectrometry identified the yellow solid as intermediate C4 (yield 20%).
  • Intermediate B4 was synthesized in the same manner, except that intermediate C4 was used instead of intermediate B3, to obtain an orange solid (1.28 g). Mass spectrometry identified the orange solid as intermediate C5 (yield 29%).
  • the compound GD-B was synthesized in the same manner, except that intermediate C5 was used instead of intermediate B4, to obtain an orange solid (0.40 g). Mass spectrometry identified the orange solid as compound GD-C (yield 31%).
  • the obtained solid was purified by silica gel column chromatography and recrystallization to obtain 122 g of a brown solid. It was identified as intermediate A by mass spectrometry (yield 86%). Under a nitrogen atmosphere, intermediate A (122 g, 340 mmol), triphenylphosphine (241 g, 919 mmol), and orthodichlorobenzene (1360 mL) were placed in a three-neck flask and stirred at 180° C. for 6 hours. The reaction solution was concentrated under reduced pressure, methanol was added, and the precipitated solid was filtered to obtain 56.1 g of a brown solid. The solid was identified as intermediate B by mass spectrometry (yield 51%).
  • intermediate C (42.5 g, 101 mmol), triphenylphosphine (71.6 g, 273 mmol), and 505 mL of orthodichlorobenzene were placed in a three-neck flask and stirred at 180°C for 12 hours.
  • Orthodichlorobenzene was removed using an evaporator, and the mixture was diluted with 100 mL of toluene, after which 300 mL of methanol was added to cause a precipitate to form.
  • the resulting precipitate was filtered off using reduced pressure filtration to obtain 32.6 g of a white solid. It was identified as intermediate D by mass spectrometry (yield 83%).
  • intermediate B 56.1 g, 172 mmol
  • 1-bromo-2,6-difluorobenzene (66.5 g, 344 mmol)
  • tripotassium phosphate (183 g, 860 mmol)
  • N,N-dimethylformamide 574 mL
  • the reaction solution was cooled to room temperature
  • water was added and the precipitated solid was collected by suction filtration.
  • the resulting solid was purified by silica gel column chromatography to obtain 23.7 g of a yellow solid. It was identified as intermediate E by mass spectrometry (yield 28%).
  • intermediate D (10.5 g, 27 mmol), intermediate E (13.5 g, 27 mmol), tripotassium phosphate (17.3 g, 81 mmol), and N,N-dimethylformamide (54 mL) were placed in a three-neck flask and stirred at 100°C for 30 hours. After the reaction solution was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 19.6 g of a yellow solid. It was identified as intermediate F by mass spectrometry (yield 84%).
  • intermediate F (29.5 g, 34.0 mmol) and t-butylbenzene (340 mL) were placed in a three-neck flask and cooled to -60°C.
  • sec-butyllithium (solvent: cyclohexane and n-hexane), 1.2 mol/L (34.0 mL, 40.8 mmol) was then added dropwise, the temperature was raised to -40°C, and the mixture was stirred for 30 minutes.
  • the reaction solution was cooled to -78°C, and boron tribromide (9.5 mL, 102 mmol) was added dropwise, the temperature was raised to room temperature, and the mixture was stirred for 10 hours.
  • intermediate G (14.3 g, 18.0 mmol), potassium hexacyanoferrate(II) (22.0 g, 45.0 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (2.5 g, 3.6 mmol), sodium carbonate (0.95 g, 9.0 mmol), and 1-methyl-2-pyrrolidone (449 mL) were placed in a three-neck flask and stirred at 135°C for 5 hours.
  • reaction solution was cooled to room temperature, and the precipitated solid was collected by suction filtration and then purified by silica gel column chromatography and recrystallization to obtain 4.0 g of an orange solid. It was identified as compound GD-D by mass spectrometry (yield 28%).
  • intermediate B (15.5 g, 48 mmol), 1-bromo-2,6-difluoro-4-iodobenzene (45.5 g, 143 mmol), tripotassium phosphate (50.5 g, 238 mmol), and N,N-dimethylformamide (95 mL) were placed in a three-neck flask and stirred at 40°C for 18 hours. After the reaction solution was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 5.5 g of a yellow solid. It was identified as intermediate H by mass spectrometry (yield 19%).
  • intermediate I (6 g, 7.1 mmol), carbazole (1.2 g, 7.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.4 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (0.4 g, 0.7 mmol), sodium tert-butoxide (1.0 g, 10.7 mmol), and xylene (143 mL) were placed in a three-neck flask and stirred at 120°C for 3 hours. After cooling the reaction solution to room temperature, it was purified by silica gel column chromatography to obtain 2.6 g of a yellow solid. It was identified as intermediate J by mass spectrometry (yield 39%).
  • intermediate J 2.4 g, 2.6 mmol
  • t-butylbenzene 26 mL
  • sec-butyllithium solvent: cyclohexane and n-hexane
  • 1.2 mol/L 2.6 mL, 3.1 mmol
  • the reaction solution was cooled to -78°C
  • boron tribromide 0.7 mL, 7.8 mmol
  • intermediate K (0.7 g, 0.82 mmol), potassium hexacyanoferrate(II) (0.6 g, 1.6 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.06 g, 0.08 mmol), sodium carbonate (0.02 g, 0.16 mmol), and 1-methyl-2-pyrrolidone (16 mL) were placed in a three-neck flask and stirred at 135°C for 5 hours.
  • reaction solution was cooled to room temperature, and the precipitated solid was collected by suction filtration and then purified by silica gel column chromatography and recrystallization to obtain 0.12 g of an orange solid. It was identified as compound GD-E by mass spectrometry (yield 17%).
  • intermediate L 50.9 g, 150 mmol
  • palladium acetate 10.1 g, 4.5 mmol
  • triphenylphosphine 23.7 g, 90 mmol
  • potassium carbonate 41.5 g, 300 mmol
  • N,N-dimethylformamide 752 mL
  • the reaction solution was cooled to room temperature, and then water and toluene were added and separated.
  • the organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. It was then purified by silica gel column chromatography to obtain 19.1 g of a white solid. It was identified as intermediate M by mass spectrometry (yield 49%).
  • intermediate E 6.5 g, 13 mmol
  • intermediate M 3.4 g, 13 mmol
  • tripotassium phosphate 8.3 g, 39 mmol
  • N,N-dimethylformamide 26 mL
  • intermediate N 3.3 g, 4.5 mmol
  • t-butylbenzene 45 mL
  • sec-butyllithium solvent: cyclohexane and n-hexane
  • 1.2 mol/L 4.5 mL, 5.4 mmol
  • the reaction solution was cooled to -78°C
  • boron tribromide 1.2 mL, 13.4 mmol
  • intermediate O (1.8 g, 2.7 mmol), potassium hexacyanoferrate(II) (5.0 g, 13.5 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.38 g, 0.54 mmol), sodium carbonate (0.14 g, 1.35 mmol), and 1-methyl-2-pyrrolidone (54 mL) were placed in a three-neck flask and stirred at 135°C for 5 hours.
  • reaction solution was cooled to room temperature, and the precipitated solid was collected by suction filtration and then purified by silica gel column chromatography and recrystallization to obtain 0.1 g of an orange solid. It was identified as compound GD-F by mass spectrometry (yield 6%).
  • organic EL element 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer.

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Abstract

L'invention concerne un composé qui a une structure représentée par la formule générale (1). Dans la formule générale (1), R110 est choisi parmi des substituants autres qu'un atome d'hydrogène ; le cycle A1, le cycle B1 et le cycle C1 représentent chacun indépendamment un cycle hydrocarboné aromatique substitué ou non substitué ayant de 6 à 30 atomes de carbone formant un cycle ou un cycle hétérocyclique aromatique substitué ou non substitué ayant de 5 à 30 atomes formant un cycle ; et L1 représente une liaison simple ou similaire. Par ailleurs, (i) au moins l'un de R108 à R111 est un groupe cyano, ou (ii) au moins un groupe cyano est substitué sur au moins l'un du cycle B1 et du cycle C1, ou (iii) au moins l'un de R108 à R111 est un groupe cyano, et au moins un groupe cyano est substitué sur au moins l'un du cycle B1 et du cycle C1.
PCT/JP2024/006002 2023-03-22 2024-02-20 Composé, matériau d'élément électroluminescent, élément électroluminescent organique et dispositif électronique WO2024195402A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220052264A1 (en) * 2020-08-12 2022-02-17 Samsung Display Co., Ltd. Light-emitting device including condensed cyclic compound and electronic apparatus including the light-emitting device
WO2022078961A1 (fr) * 2020-10-12 2022-04-21 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques
CN114605449A (zh) * 2020-12-09 2022-06-10 江苏三月科技股份有限公司 一种含硼有机化合物及其在有机电致发光器件上的应用
WO2022257817A1 (fr) * 2021-06-07 2022-12-15 清华大学 Dispositif électroluminescent organique et appareil d'affichage
JP2023036162A (ja) * 2021-09-02 2023-03-14 株式会社Kyulux 化合物、発光材料および有機発光素子

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220052264A1 (en) * 2020-08-12 2022-02-17 Samsung Display Co., Ltd. Light-emitting device including condensed cyclic compound and electronic apparatus including the light-emitting device
WO2022078961A1 (fr) * 2020-10-12 2022-04-21 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques
CN114605449A (zh) * 2020-12-09 2022-06-10 江苏三月科技股份有限公司 一种含硼有机化合物及其在有机电致发光器件上的应用
WO2022257817A1 (fr) * 2021-06-07 2022-12-15 清华大学 Dispositif électroluminescent organique et appareil d'affichage
JP2023036162A (ja) * 2021-09-02 2023-03-14 株式会社Kyulux 化合物、発光材料および有機発光素子

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