WO2024219261A1 - 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 - Google Patents

化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 Download PDF

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WO2024219261A1
WO2024219261A1 PCT/JP2024/014174 JP2024014174W WO2024219261A1 WO 2024219261 A1 WO2024219261 A1 WO 2024219261A1 JP 2024014174 W JP2024014174 W JP 2024014174W WO 2024219261 A1 WO2024219261 A1 WO 2024219261A1
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substituted
ring
carbon atoms
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司 澤藤
裕亮 糸井
佑典 高橋
将太 田中
清香 水谷
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Idemitsu Kosan Co Ltd
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Priority to CN202480026198.2A priority patent/CN121039093A/zh
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Definitions

  • the present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device including the organic electroluminescence device.
  • an organic electroluminescence element (hereinafter sometimes referred to as "organic EL element”) is composed of an anode, a cathode, and an organic layer sandwiched between the anode and cathode.
  • organic EL element When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the light-emitting region, where they recombine to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes is important in obtaining high-performance organic EL elements.
  • Patent documents 1 to 3 disclose compounds used as materials for organic electroluminescence devices.
  • the present invention has been made to solve the above problems, and aims to provide a compound and a material for an organic electroluminescence element that further improve the performance of an organic EL element, an organic EL element with improved element performance, and an electronic device including such an organic EL element.
  • organic EL elements containing a compound represented by the following formula (1A) or (1B) have improved performance.
  • the present invention provides a compound represented by formula (1A) or (1B): [In formula (1A), N * is the central nitrogen atom.
  • One selected from Z 1 to Z 4 is a single bond bonding to *a.
  • R 1 to R 4 each independently represent a light hydrogen atom.
  • the above-mentioned Z 1 to Z 4 and R 5 to R 12 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • L1 is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • n1 is 0 or 1.
  • L2 is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • n2 is 0 or 1.
  • Ar1 is bonded to the central nitrogen atom N * .
  • L3 is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. n3 is 0 or 1.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • N * is the central nitrogen atom.
  • Z 5 to Z 8 is a single bond bonding to *a.
  • Z 5 to Z 8 and R 21 to R 32 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • the above Z 5 to Z 8 and R 21 to R 32 that are not single bonds do not combine with each other to form a ring.
  • L 1 to L 3 , Ar 1 to Ar 2 , and n1 to n3 are defined as in formula (1A).
  • the present invention provides a material for an organic electroluminescence device, comprising a compound represented by the above formula (1A) or formula (1B).
  • the present invention provides an organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer being composed of a single layer or multiple layers including a light-emitting layer, and at least one layer selected from the group consisting of a single layer and multiple layers constituting the organic layer contains a compound represented by the above formula (1A) or formula (1B).
  • the present invention provides an electronic device including the organic electroluminescence element.
  • An organic EL device containing a compound represented by the above formula (1A) or formula (1B) exhibits improved device performance.
  • FIG. 1 is a schematic diagram illustrating an example of a layer structure of an organic EL element according to one embodiment of the present invention.
  • FIG. 2 is a schematic diagram showing another example of a layer structure of an organic EL element according to an embodiment of the present invention.
  • FIG. 2 is a schematic diagram showing still another example of a layer structure of an organic EL element according to an embodiment of the present invention.
  • hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.
  • any possible bonding position that is not explicitly indicated with a symbol such as "R” or "D” representing a deuterium atom is assumed to have a hydrogen atom, i.e., a protium atom, deuterium atom, or tritium atom, bonded to it.
  • the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound).
  • a compound having a structure in which atoms are bonded in a ring for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound.
  • the carbon contained in the substituent is not included in the number of ring carbon atoms.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • a 9,9-diphenylfluorenyl group has 13 ring carbon atoms
  • a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring.
  • the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) with a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly).
  • the number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent.
  • the "number of ring atoms" described below is the same unless otherwise specified.
  • the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5.
  • the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6.
  • the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
  • the "carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having carbon numbers XX to YY” refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • "YY” means an integer of 2 or more.
  • the "atomic number XX to YY” in the expression “substituted or unsubstituted ZZ group having atomic number XX to YY” refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituents when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • “YY” means an integer of 2 or more.
  • unsubstituted ZZ group refers to the case where "a substituted or unsubstituted ZZ group” is an "unsubstituted ZZ group”
  • substituted ZZ group refers to the case where "a substituted or unsubstituted ZZ group” is a "substituted ZZ group”.
  • unsubstituted in the case of "a substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a protium atom, a deuterium atom, or a tritium atom.
  • substitution in the case of "a substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substitution in the case of "a BB group substituted with an AA group” means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the "unsubstituted aryl group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
  • the "unsubstituted heterocyclic group” described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
  • the "unsubstituted alkyl group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described in this specification is, unless otherwise specified in this specification, 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
  • the "unsubstituted cycloalkyl group” described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification.
  • the "unsubstituted arylene group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
  • the number of ring atoms in the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
  • the "unsubstituted alkylene group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B).
  • unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is an "unsubstituted aryl group”
  • substituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is a "substituted aryl group”.
  • aryl group simply refers to both an "unsubstituted aryl group” and a "substituted aryl group”.
  • substituted aryl group refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group” are replaced with a substituent.
  • substituted aryl group include the "unsubstituted aryl group” in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below.
  • the examples of the "unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are merely examples, and the "substituted aryl group” described in this specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group” in the specific example group G1B below is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group” in the specific example group G1B below is further replaced with a substituent.
  • 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, m-terphenyl-3'-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, phenalenyl group, Pyrenyl group, Chrysenyl
  • 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 group” described herein is a monocyclic group or a condensed ring group.
  • the “heterocyclic group” described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B).
  • heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group” is an "unsubstituted heterocyclic group"
  • substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group” is a "substituted heterocyclic group”.
  • heterocyclic group simply includes both an "unsubstituted heterocyclic group” and a "substituted heterocyclic group”.
  • substituted heterocyclic group refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are merely examples, and the “substituted heterocyclic group” described in this specification also includes the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.
  • Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
  • Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, pyrimidinyl group, A pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, A quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthroliny
  • 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 refers to one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH2.
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B).
  • the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group"
  • the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group” is a "substituted alkyl group”.
  • substituted alkyl group refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group” are replaced with a substituent.
  • specific examples of the "substituted alkyl group” include the following "unsubstituted alkyl group” (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B).
  • the alkyl group in the "unsubstituted alkyl group” refers to a chain-like alkyl group.
  • the "unsubstituted alkyl group” includes a straight-chain “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the "substituted alkyl group” described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent.
  • Unsubstituted alkyl groups (specific example group G3A): Methyl group, Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-Butyl group, and t-butyl group.
  • Substituted alkyl groups (specific example group G3B): Heptafluoropropyl group (including isomers), pentafluoroethyl group, A 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
  • Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B).
  • the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group” is an "unsubstituted alkenyl group", and the "substituted alkenyl group” refers to the case where the "substituted or unsubstituted alkenyl group” is a "substituted alkenyl group”.
  • alkenyl group when the term “alkenyl group” is simply used, it includes both an "unsubstituted alkenyl group” and a "substituted alkenyl group”.
  • substituted alkenyl group refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include the following "unsubstituted alkenyl group” (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B).
  • the examples of the "unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” listed here are merely examples, and the "substituted alkenyl group” described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent.
  • Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, A 2-butenyl group, and a 3-butenyl group.
  • Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
  • the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group” is an "unsubstituted alkynyl group."
  • alkynyl group refers to an "unsubstituted alkynyl group” in which one or more hydrogen atoms have been replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include the following "unsubstituted alkynyl group” (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.
  • Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B).
  • unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group” is an "unsubstituted cycloalkyl group”
  • substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group” is a "substituted cycloalkyl group”.
  • substituted cycloalkyl group refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include the following "unsubstituted cycloalkyl group” (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B).
  • the examples of the "unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group” in the specific example group G6B are replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group” in the specific example group G6B is further replaced with a substituent.
  • Unsubstituted cycloalkyl groups (specific example group G6A): A cyclopropyl group, A cyclobutyl group, Cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
  • Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl group.
  • G7 of the group represented by --Si(R 901 )(R 902 )(R 903 ) described in this specification include: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6)(G6)
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • the multiple G1s in -Si(G1)(G1)(G1) are the same or different.
  • 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.
  • G10 A group represented by -N(R 906 )(R 907 )
  • 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)
  • 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.
  • -N(G6)(G6) may be the same or different from each other.
  • 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 in the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted fluoroalkyl group” are further replaced with a substituent.
  • substituents in the substituent in the "substituted fluoroalkyl group” are further replaced with a substituent.
  • Specific examples of the "unsubstituted fluoroalkyl group” include the examples of groups in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with fluorine atoms.
  • substituted or unsubstituted haloalkyl group means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the number of carbon atoms in the "unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification.
  • substituted haloalkyl group means a group in which one or more hydrogen atoms in the "haloalkyl group” are replaced with a substituent.
  • substituted haloalkyl group as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group” are further replaced with a substituent.
  • substituents in the "substituted haloalkyl group” are further replaced with a substituent.
  • Specific examples of the "unsubstituted haloalkyl group” include the examples of the group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
  • Haloalkyl groups are sometimes referred to as halogenated alkyl groups.
  • a specific example of the "substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
  • Substituted or unsubstituted alkylthio group A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
  • a specific example of the "substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • the number of ring carbon atoms of the "unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
  • a specific example of the "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • the number of ring carbon atoms of the "unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
  • a specific example of the "trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.
  • the number of carbon atoms in each alkyl group of the "trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group” described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
  • an “aralkyl group” is a group in which a hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one aspect of a “substituted alkyl group”.
  • An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group”, and the number of carbon atoms in the "unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
  • substituted or unsubstituted aralkyl group include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • the substituted or unsubstituted aryl group described herein is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a o-terphenyl-4-yl group, a o-terphenyl-3-yl group, a o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a
  • the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothi
  • zadibenzothiophenyl group diazadibenzothiophenyl group
  • (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group)
  • (9-biphenylyl)carbazolyl group (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
  • carbazolyl group is specifically any of the following groups:
  • the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.
  • dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
  • the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group".
  • Specific examples of the "substituted or unsubstituted arylene group” include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in specific example group G1.
  • Substituted or unsubstituted divalent heterocyclic group is, unless otherwise specified, a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group".
  • Specific examples of the "substituted or unsubstituted divalent heterocyclic group” include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group".
  • Specific examples of the "substituted or unsubstituted alkylene group” include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the substituted or unsubstituted arylene group described herein is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • * represents a bonding position.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents a bonding position.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • * represents a bonding position.
  • the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.
  • Q 1 to Q 9 each independently represent a hydrogen atom or a substituent.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", or the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other".
  • the pair of adjacent two that constitutes one group includes the pair of R 921 and R 922 , the pair of R 922 and R 923 , the pair of R 923 and R 924 , the pair of R 924 and R 930 , the pair of R 930 and R 925 , the pair of R 925 and R 926, the pair of R 926 and R 927 , the pair of R 927 and R 928 , the pair of R 928 and R 929 , and the pair of R 929 and R 921 .
  • one or more pairs means that two or more pairs of the adjacent two or more pairs may simultaneously form a ring.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
  • a set of two or more adjacent rings forms a ring includes not only the case where a set of "two" adjacent rings is bonded as in the above example, but also the case where a set of "three or more adjacent rings is bonded.
  • it means the case where R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , and a set of three adjacent rings (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and are condensed to the anthracene skeleton.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “fused ring” formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even if “one of the pairs of two adjacent rings” forms a “monocyclic ring” or a “fused ring”, the “monocyclic ring” or the “fused ring” can form a saturated ring or an unsaturated ring.
  • the ring Q A and the ring Q B formed in the general formula (TEMP-104) are “monocyclic rings” or “fused rings", respectively.
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) are fused rings by the fusion of the ring Q A and the ring Q C. If the ring Q A in the general formula (TMEP-104) is a benzene ring, the ring Q A is a monocyclic ring. When ring Q 1 A in the above general formula (TMEP-104) is a naphthalene ring, ring Q 1 A is a fused ring.
  • saturated ring refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • saturated ring refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.
  • aromatic hydrocarbon ring include structures in which the groups given as specific examples in specific example group G1 are terminated with a hydrogen atom.
  • aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom.
  • Forming a ring means forming a ring only with a plurality of atoms of the mother skeleton, or with a plurality of atoms of the mother skeleton and one or more arbitrary elements.
  • the ring QA formed by bonding R 921 and R 922 shown in the general formula (TEMP-104) means a ring formed by the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and one or more arbitrary elements.
  • R 921 and R 922 form a ring QA
  • the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms form a monocyclic unsaturated ring
  • the ring formed by R 921 and R 922 is a benzene ring.
  • the "arbitrary element” is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur.
  • the arbitrary element for example, in the case of a carbon or nitrogen element
  • a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below.
  • the ring formed is a heterocycle.
  • the "one or more arbitrary elements" constituting the single ring or the condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.
  • the "monocyclic ring” and the “condensed ring” are preferred.
  • the "saturated ring” and the “unsaturated ring” are preferred.
  • a “monocyclic ring” is preferably a benzene ring.
  • the "unsaturated ring” is preferably a benzene ring.
  • one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted monocyclic ring” or “combine with each other to form a substituted or unsubstituted fused ring
  • one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring” consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.
  • the substituent is, for example, the “optional substituent” described later.
  • specific examples of the substituent are the substituents described in the above-mentioned section “Substituents described in this specification”.
  • the substituent is, for example, the “optional substituent” described below.
  • substituents in the case of "substituted or unsubstituted” include, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a group selected from the group consisting of an unsubstituted
  • the two or more R 901 are the same or different from each other
  • the two or more R 902 are present, the two or more R 902 are the same or different from each other
  • the two or more R 903 are present, the two or more R 903 are the same or different from each other
  • the two or more R 904 are present, the two or more R 904 are the same or different from each other
  • the two or more R 905 are present, the two or more R 905 are the same or different from each other
  • two or more R 906 are present, the two or more R 906 are the same or different from each other
  • the two or more R 907 are present, the two or more R 907 are the same or different.
  • the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 50 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 18 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.
  • the optional substituent may further have a substituent.
  • the substituent that the optional substituent further has is the same as the optional substituent described above.
  • a numerical range expressed using "AA-BB” refers to a range that includes the number AA written before “AA-BB” as the lower limit and the number BB written after "AA-BB” as the upper limit.
  • a compound according to one embodiment of the present invention is represented by the following formula (1A) or (1B).
  • the compounds of the present invention represented by formula (1A) and each formula contained in formula (1A) described later may be simply referred to as “compound (1A)", “invention compound (1A)", or “first invention compound”.
  • the compounds of the present invention represented by formula (1B) and each formula contained in formula (1B) described later may be simply referred to as “compound (1B)", “invention compound (1B)", or "second invention compound”.
  • the first and second invention compounds may be collectively referred to simply as "invention compounds”.
  • N * is the central nitrogen atom.
  • one selected from Z 1 to Z 4 is a single bond bonding to *a, and preferably Z 1 or Z 3 is a single bond bonding to *a.
  • the partial structure A in the above formula (1A) is represented by the following formula (1x-1), (1x-2), (1x-3), or (1x-4), and is preferably represented by the following formula (1x-1) or (1x-3).
  • the compound (1A) is represented by the below-described formula (1A-1).
  • the compound (1A) is represented by the below-described formula (1A-2).
  • the unsubstituted alkyl group of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group;
  • Preferred are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a s-butyl group, a t-buty
  • the unsubstituted aryl group of the substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms is, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group;
  • Preferred is a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; More preferably, it is a phenyl group, a 2-, 3-, or
  • the substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 20, and more preferably 5 to 13 ring atoms is, for example, Pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indolizinyl group, quinolizinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazoliny
  • L 1 to L 3 each independently represent a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group, more preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and even more preferably a substituted or unsubstituted phenylene group.
  • n1, n2, and n3 are all 0; in another embodiment, n1, n2, and n3 are all 1; in yet another embodiment, n1 and n2 are 0 and n3 is 1; in yet another embodiment, n1 and n3 are 0 and n2 is 1; in yet another embodiment, n2 and n3 are 0 and n1 is 1; in yet another embodiment, n1 is 0, n2 and n3 are 1; in yet another embodiment, n2 is 0, n1 and n3 are 1; in yet another embodiment, n3 is 0 and n1 and n2 are 1.
  • L1 , L2 and L3 When L1 , L2 and L3 are present in formula (1A), the three may be the same or different from each other, or two of the three may be the same and the remaining one may be different. In formula (1A), only two of L1 , L2 , and L3 may be present (i.e., two of n1, n2, and n3 may be 1 and the other may be 0), and in this case, the two present may be the same or different from each other.
  • L1 , L2 , and L3 may be present (i.e., two of n1, n2, and n3 may be 0 and the other may be 1), or none of L1 to L3 may be present (i.e., n1, n2, and n3 may be 0).
  • the combination of "-(L 1 ) n1 -", “-(L 2 ) n2 -” and "-(L 3 ) n3 -" in compound (1A) is represented by any of the following combinations [k11] to [k18].
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and are preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. Details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by Ar 1 and Ar 2 are as described above for Z 1 to Z 4 and R 5 to R 12 that are not single bonds in formula (1A).
  • Ar 1 may be a group represented by the following formula (2-1), and Ar 2 may not be a group represented by the following formula (3-1);
  • Ar 2 may be a group represented by the following formula (3-1), and Ar 1 may not be a group represented by the following formula (2-1); or
  • Ar 1 may be a group represented by the following formula (2-1), and Ar 2 may be a group represented by the following formula (3-1).
  • ** represents the bonding position to L2 .
  • X 1 is an oxygen atom, a sulfur atom, ⁇ NR 100 , or ⁇ CR A R B , preferably an oxygen atom or ⁇ CR A R B , more preferably an oxygen atom.
  • R 41 to R 44 , R 100 , R A , and R B is a single bond bonded to *d, or one selected from R A and R B is a divalent group bonded to *d.
  • the above-mentioned R 41 to R 44 and R 45 to R 48 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably a hydrogen atom.
  • All of R 41 to R 44 and R 45 to R 48 that are not single bonds may be hydrogen atoms.
  • the adjacent pairs of groups among R 41 to R 44 that are not single bonds, and the adjacent pairs of groups among R 45 to R 48 that are not single bonds, may or may not be bonded to each other to form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R 41 to R 44 and R 45 to R 48 that are not single bonds are as described for Z 1 to Z 4 and R 5 to R 12 that are not single bonds in formula (1A).
  • the R 100 that is not a single bond, and the R A and R B that are not a single bond and are not a divalent group bonded to *d are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms.
  • the R 100 that is not a single bond, and R A and R B that are not single bonds and are not divalent groups bonded to *d may be hydrogen atoms. Details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by R 100 , R A , and R B are as described for Z 1 to Z 4 and R 5 to R 12 that are not single bonds in formula (1A).
  • formula (2-1) is represented by any one of the following formulas (1-a1) to (1-a5).
  • R 41 to R 48 and *d are as defined in formula (1A) above.
  • R A1 to R A3 , R A4 to R A8 , R B1 to R B3 , and R B4 to R B8 are hydrogen atoms.
  • the divalent group bonded to *d represented by R A and R B is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.
  • the alkylene group, arylene group, and heteroarylene group represented by R A and R B include the divalent residues of each group described with respect to the alkyl group, aryl group, and heteroaryl group represented by R A and R B , and the same applies to preferred ones.
  • X 2 is an oxygen atom, a sulfur atom, ⁇ NR 101 , or ⁇ CR C R D , preferably an oxygen atom or ⁇ CR C R D , more preferably an oxygen atom.
  • one selected from R 21B to R 24B , R 101 , R C , and R D is a single bond bonded to *b2, or one selected from R C and R D is a divalent group bonded to *b2.
  • X2 is an oxygen atom or a sulfur atom
  • one selected from R 21B to R 24B is a single bond bonding to *b2, preferably one selected from R 21B , R 22B , and R 24B is a single bond bonding to *b2, more preferably one selected from R 21B and R 24B is a single bond bonding to *b2, and even more preferably R 24B is a single bond bonding to *b2.
  • X2 NR101 , preferably one selected from R21B to R23B , and R101 is a single bond bonding to *b2, or more preferably one selected from R23B or R101 is a single bond bonding to *b2.
  • X2 is ⁇ CR C R D , preferably one selected from R 21B to R 23B , R C , and R D is a single bond bonding to *b2, or one selected from R C and R D is a divalent group bonding to *b2, and more preferably one selected from R 23B , R C , or R D is a single bond bonding to *b2, or one selected from R C and R D is a divalent group bonding to *b2.
  • R 21B to R 24B and R 25B to R 28B that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably a hydrogen atom.
  • R 21B to R 24B and R 25B to R 28B that are not single bonds may be hydrogen atoms. Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R 21B to R 28B are as described for Z 1 to Z 4 and R 5 to R 12 that are not single bonds in formula (1A).
  • R 21B to R 24B when one selected from R 21B to R 24B is a single bond bonded to *b2, the R 21B to R 24B that are not a single bond do not bond to each other to form a ring, and R 25B to R 28B may or may not bond to each other to form a ring.
  • R 101 that is not a single bond, and the above R C and R D that are not a single bond and are not a divalent group bonded to *b2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably a hydrogen atom.
  • R 101 that is not a single bond, and R C and R D that are not single bonds and are not divalent groups bonded to *b2 may each be a hydrogen atom.
  • R C and R D which are not a single bond and are not a divalent group bonded to *b2 may or may not be bonded to each other to form a ring.
  • the divalent group bonded to *b2 represented by R C and R D is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.
  • the alkylene group, arylene group, and heteroarylene group represented by R C and R D include the divalent residues of each group described with respect to the alkyl group, aryl group, and heteroaryl group represented by R A and R B , and the same applies to preferred ones.
  • At least one of Ar 1 and Ar 2 is represented by any one of the following formulas (2A) to (2F).
  • *21 is the bonding position to L2 or L3 .
  • one selected from R 101 to R 105 is a single bond bonding to *22
  • one selected from R 106 to R 110 is a single bond bonding to *23.
  • the above R 101 to R 105 that are not single bonds and R 106 to R 110 that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and preferably a hydrogen atom. All of the above R 101 to R 105 that are not single bonds and all of the above R 106 to R 110 that are not single bonds may be hydrogen atoms.
  • R 111 to R 115 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably a hydrogen atom. All of R 111 to R 115 may be a hydrogen atom.
  • n11 is 0, 1 or 2
  • n11 is 0 or 1, except for the case where m11 is 2 and n11 is 0.
  • *23 represents *21.
  • *22 represents *21.
  • *23 represents *22.
  • Ar 1 is represented by formula (2A)
  • n2 is preferably 0, and when Ar 2 is represented by formula (2A), n3 is preferably 0.
  • R 121 to R 128 is a single bond bonded to *25.
  • the above R 121 to R 128 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and preferably a hydrogen atom. All of R 121 to R 125 may be a hydrogen atom. Details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described above for Z 1 to Z 4 and R 5 to R 12 which are not single bonds in formula (1A), except that the alkyl group has 1 to 10 carbon atoms.
  • *26 is the bonding position to L2 or L3 .
  • n12 is 0 or 1.
  • n12 is 0, one selected from R 141 to R 148 is a single bond bonded to *29.
  • n12 is 1, one of R 141 and R 142 , R 142 and R 143 , or R 143 and R 144 is a single bond bonding to *h, and the other is a single bond bonding to *i, and one selected from R 141 to R 144 , R 145 to R 148 , and R 200 to R 203 that is not a single bond bonding to *h and *i is a single bond bonding to *29.
  • R 141 to R 148 that are not single bonds and R 200 to R 203 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably a hydrogen atom.
  • All of the above R 141 to R 148 that are not single bonds and all of the above R 200 to R 203 that are not single bonds may be hydrogen atoms. Details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described above for Z 1 to Z 4 and R 5 to R 12 which are not single bonds in formula (1A), except that the alkyl group has 1 to 10 carbon atoms.
  • R E and R F each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms.
  • the R E and R F may each be a hydrogen atom.
  • *30 is the bonding position to L2 or L3 .
  • R 151 to R 155 is a single bond bonding to *31, and the other selected from R 151 to R 155 is a single bond bonding to *32.
  • the above R 151 to R 155 that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group, and preferably a hydrogen atom. All of the above R 151 to R 155 that are not single bonds may be hydrogen atoms.
  • R 161 to R 165 and R 171 to R 175 each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, and preferably a hydrogen atom. All of R 161 to R 165 and R 171 to R 175 may be hydrogen atoms. Details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described above for Z 1 to Z 4 and R 5 to R 12 which are not single bonds in formula (1A), except that the alkyl group has 1 to 10 carbon atoms.
  • Formula (2E) includes groups represented by the following formulas (2E-1) to (2E-5), and formula (2E-1), (2E-2), or (2E-5) is preferred.
  • N * is the central nitrogen atom.
  • Z 5 to Z 8 and R 21 to R 32 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group (aromatic heterocyclic group) having 5 to 30 ring atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably a hydrogen atom.
  • L 1 to L 3 , Ar 1 to Ar 2 , and n1 to n3 are defined as in formula (1A).
  • R 1 to R 12 , Z 2 to Z 4 , N * , Ar 1 to Ar 2 , L 1 to L 3 , and n1 to n3 are as defined in formula (1A) above.
  • the compound (1A) is represented by the following formula (1A-2).
  • R 1 to R 12 , Z 1 , Z 2 , Z 4 , N * , Ar 1 to Ar 2 , L 1 to L 3 , and n1 to n3 are as defined in formula (1A) above.
  • the compound (1A) is represented by any one of the following formulas (1A-3) to (1A-9).
  • the compound (1A) is represented by any one of the following formulas (1A-10) to (1A-16).
  • R 51 to R 55 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. However, one selected from R 51 to R 55 is a single bond bonded to *d. All of R 51 to R 55 that are not single bonds bonded to *d may be hydrogen atoms. Among the above-mentioned R 51 to R 55 which are not single bonds, adjacent pairs do not bond to each other to form a ring.
  • R 71 to R 75 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. However, one selected from R 71 to R 75 is a single bond bonded to *f. All of R 71 to R 75 that are not the single bond bonded to *f may be hydrogen atoms. Among the above-mentioned R 71 to R 75 which are not single bonds, adjacent pairs do not bond to each other to form a ring.
  • the compound (1B) is represented by the following formula (1B-1).
  • R 21 to R 32 , Z 6 to Z 8 , N * , Ar 1 to Ar 2 , L 1 to L 3 , and n1 to n3 are as defined in formula (1B) above.
  • R 21 to R 32 , Z 5 , Z 7 to Z 8 , N * , Ar 1 to Ar 2 , L 1 to L 3 , and n1 to n3 are as defined in formula (1B) above.
  • the compound is represented by any one of the above formulas (1B), (1B-1), and (1B-2), and when n1 is 1, L 1 is a phenylene group, when n2 is 1, L 2 is a phenylene group, and when n3 is 1, L 3 is a phenylene group.
  • the compound (1B) is represented by any one of the following formulas (1B-3) to (1B-9).
  • the compound (1B) is represented by any one of the following formulas (1B-10) to (1B-16).
  • R 51 to R 55 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and preferably a hydrogen atom.
  • one selected from R 51 to R 55 is a single bond bonded to *d. All of R 51 to R 55 that are not single bonds bonded to *d may be hydrogen atoms. Among the above R 51 to R 55 which are not single bonds, adjacent pairs do not bond to each other to form a ring.
  • R 71 to R 75 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and preferably a hydrogen atom.
  • one selected from R 71 to R 75 is a single bond bonded to *f. All of R 71 to R 75 that are not the single bond bonded to *f may be hydrogen atoms.
  • adjacent pairs do not bond to each other to form a ring.
  • R 81 to R 85 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and preferably a hydrogen atom.
  • one selected from R 81 to R 85 is a single bond bonded to *g. All of R 81 to R 85 that are not the single bond bonded to *g may be hydrogen atoms.
  • adjacent pairs do not bond to each other to form a ring.
  • R 21 to R 32 , Z 5 to Z 8 , N * , Ar 1 to Ar 2 , L 1 to L 3 , and n1 to n3 are as defined in formula (1B) above.
  • the compound of the invention is represented by any one of the above formulas (1A) and (1A-1) to (1A-16), and X 1 is an oxygen atom.
  • the compound of formula (1A) or (1B) contains at least one deuterium atom.
  • the deuterium atoms contained in compound (1A) and compound (1B) will be described in detail later.
  • At least one of the following (1) to (9) is a deuterium atom.
  • the term "hydrogen atom” as used herein includes protium, deuterium, and tritium atoms.
  • the first or second invention compound may contain naturally occurring deuterium atoms.
  • deuterium atoms may be intentionally introduced into the first or second invention compound by using deuterated compounds as part or all of the raw material compounds.
  • the deuteration rate of the first or second invention compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain proportion of naturally occurring light hydrogen isotopes may be contained. Therefore, the deuteration rate of the invention compound shown below includes a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio calculated by simply counting the number of deuterium atoms represented by the chemical formula.
  • the deuteration rate of the first or second invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more.
  • the second compound of the invention may be a deuterated form in which all hydrogen atoms are deuterium atoms (i.e., the deuteration rate of the compound of the invention is 100%).
  • the first or second invention compound may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates.
  • the deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more, but less than 100%.
  • the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the first invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and still more preferably 10% or more, but less than 100%.
  • the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the second invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and still more preferably 10% or more and 100% or less.
  • the first or second invention compound can be easily produced by a person skilled in the art by referring to the synthesis examples described below and known synthesis methods.
  • first or second invention compound examples are shown below, but the compounds are not limited to these.
  • D represents a deuterium atom.
  • the material for organic EL device contains the first or second invention compound.
  • the content of the first or second invention compound in the material for organic EL device is 1 mass % or more (including 100%), preferably 10 mass % or more (including 100%), more preferably 50 mass % or more (including 100%), further preferably 80 mass % or more (including 100%), and particularly preferably 90 mass % or more (including 100%).
  • the material for organic EL device which is one embodiment of the present invention, is useful for manufacturing an organic EL device.
  • the first or second invention compound is preferably a hole transport layer material.
  • the material for an organic EL device when the first or second invention compound contains at least one deuterium atom, preferably further contains a protium derivative of the first or second invention compound, where all hydrogen atoms in the first or second invention compound are protium atoms.
  • the mixing molar ratio of the first or second invention compound and the protium derivative of the first or second invention compound is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, further preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.
  • a material for an organic electroluminescence device is a material for a hole transport layer.
  • the content of the compound of the invention in the material for organic electroluminescence devices is preferably 1% by mass or more (including 100%), more preferably 10% by mass or more (including 100%), even more preferably 50% by mass or more (including 100%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%).
  • the organic EL device comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer is composed of a single layer or multiple layers including a light-emitting layer, and at least one layer selected from the group consisting of a single layer and multiple layers constituting the organic layer comprises the compound of the present invention.
  • organic layer containing the compound of the invention examples include, but are not limited to, a hole transport zone (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light emitting layer, the light emitting layer, the spacer layer, and an electron transport zone (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light emitting layer.
  • a hole transport zone hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.
  • an electron transport zone electron injection layer, electron transport layer, hole blocking layer, etc.
  • the compound of the invention is preferably used as a material for the hole transport zone or light emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transport zone, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.
  • the organic EL element which is one aspect of the present invention, may be a monochromatic fluorescent or phosphorescent light-emitting element, a fluorescent/phosphorescent hybrid white light-emitting element, a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, and is preferably a fluorescent light-emitting element.
  • the term "light-emitting unit” refers to the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and emits light by recombining injected holes and electrons.
  • the light-emitting unit may be a multi-layer type having a plurality of phosphorescent or fluorescent light-emitting layers, in which case a spacer layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer.
  • a typical layer structure of a simple light-emitting unit is shown below. The layers in parentheses are optional.
  • the phosphorescent or fluorescent light-emitting layers may each emit light of a different color.
  • the light-emitting unit (d) may have a layer structure such as a hole injection layer/a hole transport layer/a first phosphorescent light-emitting layer (red light-emitting)/a second phosphorescent light-emitting layer (green light-emitting)/a spacer layer/a fluorescent light-emitting layer (blue light-emitting)/an electron transport layer.
  • An electron blocking layer may be provided between each light-emitting layer and the hole transport layer or between each spacer layer as needed.
  • a hole blocking layer may be provided between each light-emitting layer and the electron transport layer as needed.
  • Representative element configurations of the tandem type organic EL element include the following.
  • the first light-emitting unit and the second light-emitting unit can be, for example, each independently selected from the light-emitting units described above.
  • the intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connection layer, or intermediate insulating layer, and can be made of a known material configuration that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.
  • FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL element according to one embodiment of the present invention.
  • the organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4.
  • the light-emitting unit 10 has a light-emitting layer 5.
  • a hole transport zone 6 (hole injection layer, hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3
  • an electron transport zone 7 electron injection layer, electron transport layer, etc.
  • an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. This allows electrons and holes to be trapped in the light-emitting layer 5, further increasing the efficiency of exciton generation in the light-emitting layer 5.
  • FIG. 2 is a schematic diagram showing another configuration of an organic EL element according to one embodiment of the present invention.
  • the organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4.
  • the light-emitting unit 20 has a light-emitting layer 5.
  • the hole transport zone disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c.
  • the electron transport zone disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.
  • the organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4.
  • the light-emitting unit 30 has a light-emitting layer 5.
  • the hole transport zone disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d.
  • the electron transport zone disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.
  • the hole transport layer (B) is preferably an electron blocking layer. Therefore, in one embodiment of the present invention, for example, when describing the configuration of an organic EL element shown in the schematic diagram of Figure 3, it is more preferable that at least one layer selected from the first hole transport layer 6b and the second hole transport layer 6c is the hole transport layer (A), and the third hole transport layer 6d is the hole transport layer (B) and also an electron blocking layer. In one embodiment of the present invention, it is preferable that the hole transport layer (A) and the hole transport layer (B) are in direct contact with each other.
  • the second hole transport layer 6c is the hole transport layer (A)
  • the third hole transport layer 6d is the hole transport layer (B) and is also an electron blocking layer.
  • a host combined with a fluorescent dopant material is called a fluorescent host
  • a host combined with a phosphorescent dopant material is called a phosphorescent host.
  • Fluorescent hosts and phosphorescent hosts are not distinguished only by molecular structure.
  • a phosphorescent host means a material that forms a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescent light-emitting layer. The same applies to fluorescent hosts.
  • the substrate is used as a support for the organic EL element.
  • a plate such as glass, quartz, or plastic can be used as the substrate.
  • a flexible substrate may also be used.
  • a plastic substrate made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride can be used as the flexible substrate.
  • An inorganic deposition film can 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).
  • 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, indium oxide containing tungsten oxide and zinc oxide, and graphene.
  • indium oxide-zinc oxide can be formed by sputtering using a target in which 1-10 wt% zinc oxide is added to indium oxide
  • indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target in which 0.5-5 wt% tungsten oxide and 0.1-1 wt% zinc oxide are added to indium oxide.
  • Other methods that can be used to form the films include vacuum deposition, coating, inkjet, and spin coating.
  • the organic layer may include a hole transporting zone between the anode and the light emitting layer.
  • the hole transporting zone is composed of a hole injection layer, a hole transporting layer, an electron blocking layer, etc. It is preferable that the hole transporting zone contains the invention compound. It is preferable that at least one of these layers constituting the hole transporting layer contains the invention compound, and it is more preferable that the invention compound is contained in the hole transporting layer in particular.
  • the hole injection layer formed in contact with the anode is formed using a material that easily injects holes regardless of the work function of the anode, and therefore materials that are commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, and 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, and 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, an inkjet method, etc. can be used.
  • the hole injection layer is a layer containing a material with high hole injection properties (hole-injecting material) and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.
  • hole injection materials examples include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc.
  • Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.
  • examples include 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), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD).
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]phenyl
  • Polymer compounds to which an acid has been added such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can also be used.
  • PEDOT/PSS poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid)
  • PAni/PSS polyaniline/poly(styrenesulfonic acid)
  • acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).
  • HAT hexaazatriphenylene
  • R 221 to R 226 each independently represent a cyano group, -CONH 2 , a carboxyl group, or -COOR 227 (R 227 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms).
  • R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 may be bonded to each other to form a group represented by -CO-O-CO-.
  • R 227 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the hole transport layer is a layer containing a material with high hole transport properties (hole transport material) and is formed between the anode and the light emitting layer, or, if present, between the hole injection layer and the light emitting layer.
  • the invention compound may be used in the hole transport layer alone or in combination with the following compounds:
  • the hole transport layer may be a single layer structure or a multilayer structure including two or more layers.
  • the hole transport layer may be a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole transport zone may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side.
  • the hole transport layer may also be a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in this order from the anode side. That is, the third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer.
  • the hole transport layer of the single layer structure is preferably adjacent to the light emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is preferably adjacent to the light emitting layer.
  • an electron blocking layer which will be described later, may be interposed between the hole transport layer and the light emitting layer of the single layer structure, or between the hole transport layer closest to the light emitting layer and the light emitting layer in the multilayer structure.
  • at least one of the first hole transport layer and the second hole transport layer contains the invention compound.
  • the invention compound in the hole transport layer having a two-layer structure, may be contained in either the first hole transport layer or the second hole transport layer, or may be contained in both. In another embodiment, at least one of the first to third hole transport layers contains the invention compound. Specifically, in the hole transport layer having a three-layer structure, the invention compound may be contained in only one of the first to third hole transport layers, or in only two of them, or in all of them. In one embodiment of the present invention, the compound of the present invention is preferably contained in the second hole transport layer, and specifically, the compound of the present invention is preferably contained only in the second hole transport layer, or the compound of the present invention is preferably contained in both the first hole transport layer and the second hole transport layer.
  • the compound of the invention contained in one or both of the first hole transport layer and the second hole transport layer, and the compound of the invention contained in at least one or more of the first to third hole transport layers are preferably protonated compounds from the viewpoint of production costs.
  • the above-mentioned proton derivative refers to a compound of the invention in which all hydrogen atoms are proton atoms. Therefore, the present invention includes an organic EL device in which one or both of the first hole transport layer and the second hole transport layer, and at least one or more of the first to third hole transport layers, contain an invention compound substantially consisting of protium compounds.
  • invention compound substantially consisting of protium compounds means that the content of protium compounds relative to the total amount of the invention compound is 90 mol % or more, preferably 95 mol % or more, and more preferably 99 mol % or more (each including 100%).
  • aromatic amine compounds examples include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl] )-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphen
  • carbazole derivatives examples include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).
  • anthracene derivatives examples include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • compounds other than those mentioned above may be used as long as they have a higher hole transporting property than an electron transporting property.
  • the first hole transport layer contains a compound represented by the following formula (21) or formula (22).
  • L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
  • k is 1, 2, 3 or 4;
  • L E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
  • the multiple L E2s are the same or different from each other, when k is 2, 3 or 4, multiple L E2s are bonded to each other to
  • R 901 to R 907 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
  • the plurality of R 901 are the same or different from each other
  • the R 902 are the same or different from each other
  • the R 903 are the same or different from each other
  • the R 904 are the same or different from each other
  • the plurality of R 905 the plurality of R 905 are the plurality of R 905 are the same or different from each
  • the first hole transport layer may contain one type of compound represented by formula (21) and formula (22), or may contain multiple types of compounds represented by formula (21) and formula (22).
  • A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
  • At least one of A1, B1, and C1 in formula (21), and at least one of A2, B2, C2, and D2 in formula (22) are a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
  • the fluorenyl group that can be A1, B1, C1, A2, B2, C2, and D2 may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group.
  • the substituents at the 9-position may form a ring together, for example, a fluorene skeleton or a xanthene skeleton together.
  • L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • Dopant material of the light-emitting layer is a layer containing a highly light-emitting material (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state.
  • the light-emitting layer is a single layer.
  • the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.
  • Blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc.
  • N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine abbreviation: YGA2S
  • 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine abbreviation: YGAPA
  • 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine abbreviation: PCBAPA
  • Aromatic amine derivatives and the like can be used as green fluorescent light-emitting materials that can be used in the light-emitting layer.
  • 2PCAPA N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine
  • 2PCABPhA N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine
  • 2DPAPA N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine
  • 2DPAPA N-[9 ,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine
  • 2DPAPA N-[9 ,10-bis(1,1'-b
  • Tetracene derivatives, diamine derivatives, etc. can be used as red fluorescent materials that can be used in the light-emitting layer.
  • Specific examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc.
  • the light-emitting layer contains a fluorescent material (fluorescent dopant material).
  • Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer.
  • examples include bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinato-N
  • Iridium complexes are used as green phosphorescent materials that can be used in the light-emitting layer.
  • examples include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).
  • organometallic complex examples include bis[2-(2'-benzo[4,5- ⁇ ]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,
  • rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propandionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light from rare earth metal ions (electron transition between different multiplicities).
  • the light-emitting layer may have a structure in which the above-mentioned dopant material is dispersed in another material (host material). It is preferable to use a material having a lower lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the dopant material.
  • LUMO lowest unoccupied molecular orbital
  • HOMO lower highest occupied molecular orbital
  • Examples of 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 carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; (4) An aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.
  • metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes
  • Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives
  • Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene
  • metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ); Heterocyclic compounds such as 2-(4-biphenylyl
  • the organic EL element when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer.
  • the dopant material contained in the first light-emitting layer may be different from the dopant material contained in the second light-emitting layer, or the host material contained in the first light-emitting layer may be different from the host material contained in the second light-emitting layer.
  • the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less.
  • the method for measuring the main peak wavelength of a compound is as follows: A 5 ⁇ mol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K).
  • the emission spectrum can be measured using a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here.
  • the peak wavelength at which the emission intensity is maximum is defined as the main peak wavelength.
  • the main peak wavelength may be referred to as the fluorescent emission main peak wavelength (FL-peak).
  • the luminescent compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less may be the above-mentioned dopant material or the above-mentioned host material.
  • the light-emitting layer is a single layer, only one of the dopant material and the host material may be a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, or both of the materials may be light-emitting compounds that exhibit fluorescent emission having a main peak wavelength of 500 nm or less.
  • the light-emitting layer includes a first light-emitting layer and a second light-emitting layer
  • only one of the first light-emitting layer and the second light-emitting layer may contain a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less
  • both light-emitting layers may contain a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less.
  • the first light-emitting layer includes a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less
  • only one of the dopant material and the host material included in the first light-emitting layer may be a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less.
  • the second light-emitting layer includes a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less
  • only one of the dopant material and the host material included in the second light-emitting layer may be a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less.
  • the electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is formed between the light emitting layer and the cathode, or, if present, between the electron injection layer and the light emitting layer.
  • the electron transport layer may be a single-layer structure or a multi-layer structure including two or more layers.
  • the electron transport layer may be a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side).
  • the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the electron transport layer closest to the anode in the multi-layer structure, for example, the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer.
  • a hole blocking layer which will be described later, may be interposed between the electron transport layer and the light-emitting layer of the single-layer structure, or between the electron transport layer closest to the light-emitting layer and the light-emitting layer in the multi-layer structure.
  • the electron transport layer may contain, for example, (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; (3) Polymer compounds can be used.
  • Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes
  • Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives
  • Polymer compounds can be used.
  • metal complexes examples include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).
  • Alq tris(8-quinolinolato)aluminum(III)
  • heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2 ,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxa
  • polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).
  • the above-mentioned materials have an electron mobility of 10 ⁇ 6 cm 2 /Vs or more. Note that materials other than the above-mentioned materials may be used for the electron transport layer as long as they have a higher electron transport property than a hole transport property.
  • the electron injection layer is a layer containing a material with high electron injection properties.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • rare earth metals such as europium (Eu), ytterbium (Yb)
  • compounds containing these metals can be used.
  • examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes.
  • a mixture of a plurality of these compounds can also be used.
  • a material having an electron transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq, etc. may be used.
  • electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor.
  • the organic compound is preferably a material that is excellent in transporting the received electrons, and specifically, for example, the above-mentioned materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used.
  • the electron donor may be any material that exhibits electron donating properties to the organic compound.
  • alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples of such materials include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferred, and examples of such materials include lithium oxide, calcium oxide, and barium oxide.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.
  • Cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less).
  • a cathode material include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such as euro
  • 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.
  • Insulating Layer Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to an ultra-thin film.
  • an insulating layer made of an insulating thin film may be inserted between a pair of electrodes.
  • materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. Mixtures or laminates of these materials may also be used.
  • the space layer is a layer provided between a fluorescent light-emitting layer and a phosphorescent light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer or for the purpose of adjusting the carrier balance, for example, when a fluorescent light-emitting layer and a phosphorescent light-emitting layer are laminated.
  • the space layer can also be provided between a plurality of phosphorescent light-emitting layers. Since the spacer layer is provided between the light-emitting layers, it is preferable that the spacer layer is made of a material having both electron transport properties and hole transport properties.
  • the triplet energy is 2.6 eV or more.
  • Materials used for the spacer layer include the same materials as those used for the hole transport layer described above.
  • Blocking layer A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer may be provided adjacent to the light-emitting layer.
  • the electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer
  • the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer.
  • the exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to surrounding layers and trapping the excitons within the light-emitting layer.
  • the layers of the organic EL element can be formed by a conventionally known deposition method, coating method, etc.
  • they can be formed by a conventional deposition method such as vacuum deposition method or molecular beam deposition method (MBE method), or a coating method such as dipping method, spin coating method, casting method, bar coating method, roll coating method, etc., using a solution of the compound that forms the layer.
  • a conventional deposition method such as vacuum deposition method or molecular beam deposition method (MBE method)
  • MBE method molecular beam deposition method
  • a coating method such as dipping method, spin coating method, casting method, bar coating method, roll coating method, etc., using a solution of the compound that forms the layer.
  • each layer there are no particular limitations on the thickness of each layer, but generally, if the thickness is too thin, defects such as pinholes are likely to occur, while if it is too thick, a high driving voltage is required, resulting in poor efficiency, so the thickness is usually 5 nm to 10 ⁇ m, and 10 nm to 0.2 ⁇ m is more preferable.
  • the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less, preferably 40 nm or more and 130 nm or less.
  • the second hole transport layer has a thickness of 20 nm or more, preferably 25 nm or more, more preferably 35 nm or more, and preferably 100 nm or less.
  • the hole transport layer adjacent to the light emitting layer has a thickness of 20 nm or more, preferably 25 nm or more, more preferably 30 nm or more, and preferably 100 nm or less.
  • the thickness D1 of the first hole transport layer and the thickness D2 of the second hole transport layer satisfy the relationship of 0.3 ⁇ D2/D1 ⁇ 4.0, preferably 0.5 ⁇ D2/D1 ⁇ 3.5, and more preferably 0.75 ⁇ D2/D1 ⁇ 3.0.
  • an organic EL element of the present invention for example, An organic EL element having the above two-layer hole transport layer, the first embodiment, in which the second hole transport layer comprises a compound according to the invention and the first hole transport layer does not comprise a compound according to the invention; A second embodiment, in which both the first hole transport layer and the second hole transport layer comprise a compound of the invention; A third embodiment in which the first hole transport layer comprises a compound of the invention and the second hole transport layer does not comprise a compound of the invention; An organic EL element having the above three-layer hole transport layer, A fourth embodiment, in which the first hole transport layer comprises a compound of the invention and the second and third hole transport layers do not comprise a compound of the invention; A fifth embodiment, in which the second hole transport layer comprises a compound of the invention and the first and third hole transport layers do not comprise a compound of the invention; A sixth embodiment, in which the third hole transport layer comprises a compound of the invention and the first and second hole transport layers do not comprise a compound of the invention; the seventh embodiment, in which the first hole
  • the organic EL element can be used in display components such as organic EL panel modules, display devices for televisions, mobile phones, personal computers, and electronic equipment such as light-emitting devices for lighting and vehicle lamps.
  • 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 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the ITO transparent electrode was attached to a substrate holder of a vacuum deposition apparatus. First, the compound Inv-1 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, to form a hole injection layer having a thickness of 10 nm.
  • the mass ratio of the compound Inv-1 to the compound HA was 90:10.
  • the compound Inv-1 was evaporated onto the hole injection layer to form a first hole transport layer having a thickness of 70 nm.
  • the compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 7.5 nm.
  • the compound BH-1 (host material) and the compound BD-1 (dopant material) were co-deposited to form a first light-emitting layer having a thickness of 8.5 nm.
  • the mass ratio of the compound BH-1 to the compound BD-1 (BH-1:BD-1) was 98.5:1.5.
  • the compound BH-2 (host material) and the compound BD-1 (dopant material) were co-deposited to form a second emitting layer having a thickness of 8.5 nm.
  • the mass ratio of the compound BH-2 to the compound BD-1 (BH-2:BD-1) was 98.5:1.5.
  • the compound ET-1 was deposited on the second light-emitting layer to form a first electron transport layer having a thickness of 5 nm.
  • a second electron transport layer having a thickness of 30 nm was formed on the first electron transport layer by co-evaporation of the compounds ET-2 and Liq.
  • the mass ratio of the compounds ET-2 and Liq (ET-2:Liq) was 50:50.
  • Example 2 An organic EL device was prepared in the same manner as in Example 1, except that the compound Inv-1 in the hole injection layer and the first hole transport layer was replaced with the compound Inv-2.
  • Example 3 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 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the ITO transparent electrode was attached to a substrate holder of a vacuum deposition apparatus. First, the compound HT-1 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HA (HT-1:HA) was 95:5.
  • compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 30 nm.
  • the compound Inv-1 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 40 nm.
  • the compound HT-3 was deposited on the second hole transport layer to form a third hole transport layer having a thickness of 15 nm.
  • a compound BH (host material) and a compound BD (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm.
  • the mass ratio of the compound BH to the compound BD was 98:2.
  • the compound ET-3 was evaporated onto the light-emitting layer to form a first electron transport layer having a thickness of 10 nm.
  • a second electron transport layer having a thickness of 20 nm was formed on the first electron transport layer by co-evaporation of the compound ET-4 and Li.
  • the mass ratio of the compound ET-4 to Li (ET-4:Li) was 96:4.
  • metallic Al was evaporated onto the second electron transport layer to form a metal cathode having a thickness of 80 nm.
  • the layer structure of the organic EL element of Example 3 thus obtained is shown below.
  • Example 4 An organic EL device was prepared in the same manner as in Example 3, except that the compound Inv-1 in the second hole transport layer material was replaced with the compound Inv-2.
  • Example 5 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 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the ITO transparent electrode was attached to a substrate holder of a vacuum deposition apparatus. First, the compounds HT-4 and HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, to form a hole injection layer having a thickness of 10 nm. The mass ratio of the compounds HT-4 and HA (HT-4:HA) was 95:5.
  • the compound HT-4 was evaporated onto the hole injection layer to form a first hole transport layer having a thickness of 30 nm.
  • the compound Inv-3 was evaporated onto the first hole transport layer to form a second hole transport layer having a thickness of 40 nm.
  • the compound HT-3 was deposited on the second hole transport layer to form a third hole transport layer having a thickness of 15 nm.
  • a compound BH (host material) and a compound BD (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm.
  • the mass ratio of the compound BH to the compound BD was 98:2.
  • the compound ET-3 was evaporated onto the light-emitting layer to form a first electron transport layer having a thickness of 10 nm.
  • a second electron transport layer having a thickness of 20 nm was formed on the first electron transport layer by co-evaporation of the compound ET-4 and Li.
  • the mass ratio of the compound ET-4 to Li (ET-4:Li) was 96:4.
  • metallic Al was evaporated onto the second electron transport layer to form a metal cathode having a thickness of 80 nm.
  • the layer structure of the organic EL element of Example 5 thus obtained is shown below.
  • Example 6 An organic EL device was prepared in the same manner as in Example 5, except that the compound Inv-3 in the second hole transport layer material was replaced with the compound Inv-4.
  • Example 7 An organic EL device was prepared in the same manner as in Example 5, except that the compound Inv-3 in the second hole transport layer material was replaced with the compound Inv-5.
  • Example 8 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 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the ITO transparent electrode was attached to a substrate holder of a vacuum deposition apparatus. First, the compounds HT-4 and HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, to form a hole injection layer having a thickness of 10 nm. The mass ratio of the compounds HT-4 and HA (HT-4:HA) was 95:5.
  • the compound HT-4 was evaporated onto the hole injection layer to form a first hole transport layer having a thickness of 30 nm.
  • the compound Inv-2 was evaporated onto the first hole transport layer to form a second hole transport layer having a thickness of 40 nm.
  • the compound HT-3 was deposited on the second hole transport layer to form a third hole transport layer having a thickness of 15 nm.
  • a compound BH (host material) and a compound BD (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm.
  • the mass ratio of the compound BH to the compound BD was 98:2.
  • the compound ET-3 was evaporated onto the light-emitting layer to form a first electron transport layer having a thickness of 10 nm.
  • a second electron transport layer having a thickness of 20 nm was formed on the first electron transport layer by co-evaporation of the compound ET-5 and Li.
  • the mass ratio of the compound ET-5 to Li (ET-5:Li) was 96:4.
  • metallic Al was evaporated onto the second electron transport layer to form a metal cathode having a thickness of 80 nm.
  • the layer structure of the organic EL element of Example 8 thus obtained is shown below.
  • Example 9 An organic EL device was prepared in the same manner as in Example 8, except that the compound Inv-2 in the second hole transport layer material was replaced with the compound Inv-6.
  • Example 10 An organic EL device was prepared in the same manner as in Example 8, except that the compound Inv-2 in the second hole transport layer material was replaced with the compound Inv-7.

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PCT/JP2024/014174 2023-04-21 2024-04-05 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 Ceased WO2024219261A1 (ja)

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