WO2024024726A1 - Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique - Google Patents

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

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WO2024024726A1
WO2024024726A1 PCT/JP2023/027012 JP2023027012W WO2024024726A1 WO 2024024726 A1 WO2024024726 A1 WO 2024024726A1 JP 2023027012 W JP2023027012 W JP 2023027012W WO 2024024726 A1 WO2024024726 A1 WO 2024024726A1
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良多 高橋
清香 水谷
真人 三谷
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • the present invention relates to a novel compound, a material for an organic electroluminescent device, an organic electroluminescent device, and an electronic device.
  • an organic electroluminescent element hereinafter also referred to as an organic EL element
  • holes are injected from the anode and electrons from the cathode, respectively, into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons recombine to form excitons.
  • Patent Documents 1 and 2 disclose the use of a compound having a specific structure in an electron transport layer of an organic EL element.
  • An object of the present invention is to provide a high-performance organic EL device and a compound that can realize the organic EL device.
  • R A is a hydrogen atom or a substituent R.
  • Ar 1 and Ar 2 are each independently, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 1 to L 3 are each independently, single bond, A substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • n1 is an integer from 0 to 4, and when n1 is 0, (L 1 ) n1 is a single bond.
  • the plurality of L 1s may be the same or different.
  • n2 is an integer from 0 to 4, and when n2 is 0, (L 2 ) n2 is a single bond.
  • n3 is an integer from 0 to 4, and when n3 is 0, (L 3 ) n3 is a single bond.
  • the plurality of L 3s may be the same or different.
  • the pair of R 3 and R 4 may be bonded to each other to form a substituted or unsubstituted benzene ring, or may not be bonded to each other.
  • the pair of R 5 and R 6 may be bonded to each other to form a substituted or unsubstituted benzene ring, or may not be bonded to each other.
  • R 1 , R 2 , R 3 and R 4 that do not bond to each other, and R 5 and R 6 that do not bond to each other are each independently a hydrogen atom or a substituent R.
  • the pair R 1 and R 2 do not bond to each other.
  • the pair R 4 and R 5 do not bond to each other.
  • X 11 is O or S.
  • R 11 to R 14 is a single bond that binds to (L 3 ) n3 .
  • (L 3 ) R 11 to R 14 that are not single bonds bonded to n3 are hydrogen atoms.
  • One or more sets of two or more adjacent ones of R 15 to R 18 are bonded to each other to form a substituted or unsubstituted benzene ring, or are not bonded to each other.
  • the substituent is the substituent X.
  • R 15 to R 18 that are not bonded to each other are each independently a hydrogen atom or a substituent X.
  • the substituent X is Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms and containing no nitrogen atom.
  • the substituent R is Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted
  • R 901 to R 907 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more R 901 to R 907 are present, each of the two or more R 901 to R 907 may be the same or different. ]
  • a high-performance organic EL device and a compound capable of realizing the organic EL device can be provided.
  • FIG. 1 is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention.
  • the hydrogen atom includes isotopes having different numbers of neutrons, ie, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • a hydrogen atom that is, a light hydrogen atom, a deuterium atom, or Assume that tritium atoms are bonded.
  • the number of carbon atoms forming a ring refers to the number of carbon atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). represents the number of carbon atoms among the atoms.
  • a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound represents the number of carbon atoms among the atoms.
  • the carbon contained in the substituent is not included in the number of carbon atoms forming the ring.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 carbon atoms
  • a naphthalene ring has 10 carbon atoms
  • a pyridine ring has 5 carbon atoms
  • a furan ring has 4 carbon atoms.
  • the number of ring carbon atoms in the 9,9-diphenylfluorenyl group is 13
  • the number of ring carbon atoms in the 9,9'-spirobifluorenyl group is 25.
  • the benzene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the benzene ring.
  • the number of ring carbon atoms in the benzene ring substituted with an alkyl group is 6. Further, when the naphthalene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the naphthalene ring. Therefore, the number of ring carbon atoms in the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring-forming atoms refers to compounds with a structure in which atoms are bonded in a cyclic manner (e.g., monocyclic, fused ring, and ring assembly) (e.g., monocyclic compound, fused ring compound, bridged compound, carbocyclic compound). Represents the number of atoms that constitute the ring itself (compounds and heterocyclic compounds). Atoms that do not form a ring (for example, a hydrogen atom that terminates a bond between atoms that form a ring) and atoms that are included in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms.
  • the "number of ring-forming atoms" described below is the same unless otherwise specified.
  • the number of ring atoms in the pyridine ring is 6, the number of ring atoms in the quinazoline ring is 10, and the number of ring atoms in the furan ring is 5.
  • the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents is not included in the number of atoms forming the pyridine ring. Therefore, the number of ring atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is six.
  • carbon number XX to YY in the expression “substituted or unsubstituted ZZ group with carbon number XX to YY” represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in substituents.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • number of atoms XX to YY in the expression “substituted or unsubstituted ZZ group with number of atoms XX to YY” represents the number of atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of atoms of substituents in case.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and "YY" means an integer of 2 or more.
  • an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a "substituted or unsubstituted ZZ group". represents the case where is a "substituted ZZ group".
  • "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that the hydrogen atom in the ZZ group is not replaced with a substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a light hydrogen atom, a deuterium atom, or a tritium atom.
  • substituted in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substitution in the case of "BB group substituted with an AA group” similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the number of ring carbon atoms in the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified herein. .
  • the number of ring atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified herein. be.
  • the number of carbon atoms in the "unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
  • the number of ring carbon atoms in the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6. be.
  • the number of ring carbon atoms in the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18. .
  • the number of ring atoms of the "unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 unless otherwise specified herein. ⁇ 18.
  • the number of carbon atoms in the "unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B). ) etc.
  • the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is an "unsubstituted aryl group"
  • the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is (Refers to the case where it is a "substituted aryl group.)
  • aryl group includes both "unsubstituted aryl group” and “substituted aryl group.”
  • “Substituted aryl group” means a group in which one or more hydrogen atoms of "unsubstituted aryl group” are replaced with a substituent.
  • Examples of the "substituted aryl group” include a group in which one or more hydrogen atoms of the "unsubstituted aryl group” in the specific example group G1A below are replaced with a substituent, and a substituted aryl group in the following specific example group G1B. Examples include: The examples of “unsubstituted aryl group” and “substituted aryl group” listed here are just examples, and the "substituted aryl group” described in this specification includes the following specific examples.
  • aryl group (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzocrysenyl group,
  • aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsily
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
  • a “heterocyclic group” as described herein is a monocyclic group or a fused ring group.
  • a “heterocyclic group” as described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • substituted or unsubstituted heterocyclic group examples include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group ( Examples include specific example group G2B).
  • unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”
  • substituted heterocyclic group refers to "substituted or unsubstituted heterocyclic group”
  • Heterocyclic group refers to a "substituted heterocyclic group."
  • heterocyclic group refers to "unsubstituted heterocyclic group” and “substituted heterocyclic group.” including both.
  • “Substituted heterocyclic group” means a group in which one or more hydrogen atoms of "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include a group in which the hydrogen atom of the "unsubstituted heterocyclic group” in specific example group G2A is replaced, and examples of substituted heterocyclic groups in specific example group G2B below. Can be mentioned.
  • Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), and unsubstituted heterocyclic groups containing a sulfur atom.
  • heterocyclic group (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), and substituted heterocyclic groups containing a sulfur atom.
  • group Specific Example Group G2B3
  • one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are substituents.
  • Includes substituted groups (Example Group G2B4).
  • ⁇ Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, Tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, Thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group
  • ⁇ Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): frill group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic group derived from the represented ring structure includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2 .
  • Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.
  • ⁇ Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, A t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
  • ⁇ Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
  • one or more hydrogen atoms of a monovalent heterocyclic group means a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, at least one of X A and Y A is NH It means one or more hydrogen atoms selected from a hydrogen atom bonded to a nitrogen atom when the above is the case, and a hydrogen atom of a methylene group when one of X A and Y A is CH 2 .
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). ).
  • an unsubstituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group” is an "unsubstituted alkyl group," and a substituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group” is (This refers to the case where it is a "substituted alkyl group.”)
  • alkyl group when it is simply referred to as an "alkyl group,” it includes both an "unsubstituted alkyl group” and a "substituted alkyl group.”
  • “Substituted alkyl group” means a group in which one or more hydrogen atoms in "unsubstituted alkyl group” are replaced with a substituent.
  • substituted alkyl group examples include groups in which one or more hydrogen atoms in the "unsubstituted alkyl group” (specific example group G3A) below are replaced with a substituent, and substituted alkyl groups (specific examples examples include group G3B).
  • the alkyl group in "unsubstituted alkyl group” means a chain alkyl group. Therefore, the "unsubstituted alkyl group” includes a linear "unsubstituted alkyl group” and a branched "unsubstituted alkyl group”.
  • ⁇ Unsubstituted alkyl group (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group.
  • ⁇ Substituted alkyl group (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group.
  • “Substituted or unsubstituted alkenyl group” Specific examples of the "substituted or unsubstituted alkenyl group" (specific example group G4) described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc.
  • the term "unsubstituted alkenyl group” refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group”
  • “substituted alkenyl group” refers to "substituted or unsubstituted alkenyl group”).
  • alkenyl group includes both “unsubstituted alkenyl group” and “substituted alkenyl group.”
  • Substituted alkenyl group means a group in which one or more hydrogen atoms in "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include the following "unsubstituted alkenyl group” (specific example group G4A) having a substituent, and the substituted alkenyl group (specific example group G4B). It will be done.
  • ⁇ Unsubstituted alkenyl group (specific example group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group and 3-butenyl group.
  • ⁇ Substituted alkenyl group (specific example group G4B): 1,3-butandienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group and 1,2-dimethylallyl group.
  • unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group” is “unsubstituted alkynyl group."
  • "unsubstituted alkynyl group” is referred to as "unsubstituted alkynyl group.”
  • ⁇ alkynyl group'' and ⁇ substituted alkynyl group.'' "Substituted alkynyl group” means a group in which one or more hydrogen atoms in "unsubstituted alkynyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group” (specific example group G5A) are replaced with a substituent.
  • 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 ( Examples include specific example group G6B).
  • unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group” is “unsubstituted cycloalkyl group”, and the term “substituted cycloalkyl group” refers to “substituted or unsubstituted cycloalkyl group”).
  • cycloalkyl group refers to a "substituted cycloalkyl group.
  • simply “cycloalkyl group” refers to "unsubstituted cycloalkyl group” and “substituted cycloalkyl group.” including both.
  • Substituted cycloalkyl group means a group in which one or more hydrogen atoms in "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include the following "unsubstituted cycloalkyl group” (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and a substituted cycloalkyl group. (Specific example group G6B) and the like can be mentioned.
  • cycloalkyl group (specific example group G6A): cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • cycloalkyl group (specific example group G6B): 4-methylcyclohexyl group.
  • G7 Specific examples of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification (specific example group G7) 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) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G2's in Si(G2) (G2) (G2) are mutually the same or different.
  • a plurality of G3's in Si(G3) (G3) are mutually the same or different.
  • - A plurality of G6's in Si(G6) (G6) (G6) are mutually the same or different.
  • G8 Specific examples of the group represented by -O-(R 904 ) described in this specification (specific example group G8) include: -O(G1), -O(G2), -O (G3) and -O (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G9 Group represented by -S-(R 905 )
  • Specific examples of the group represented by -S-(R 905 ) described in this specification include: -S (G1), -S (G2), -S (G3) and -S (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G10 Group represented by -N(R 906 )(R 907 )
  • Specific examples of the group represented by -N(R 906 )(R 907 ) described in this specification include: -N(G1)(G1), -N(G2)(G2), -N (G1) (G2), -N (G3) (G3), and -N (G6) (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • -N(G1) A plurality of G1's in (G1) are mutually the same or different.
  • -N(G2) A plurality of G2's in (G2) are the same or different.
  • -N(G3) A plurality of G3's in (G3) are mutually the same or different.
  • -N(G6) Multiple G6s in (G6) are the same or different from each other
  • halogen atom specifically examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • substituted or unsubstituted fluoroalkyl group refers to a "substituted or unsubstituted alkyl group" in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced with a fluorine atom. It also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group” are replaced with fluorine atoms (perfluoro group).
  • the number of carbon atoms in the "unsubstituted fluoroalkyl group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • “Substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the "fluoroalkyl group” are replaced with a substituent.
  • substituted fluoroalkyl group described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl group” is further replaced with a substituent, and Also included are groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group” are further replaced with a substituent.
  • substituents of a substituent in a "substituted fluoroalkyl group” are further replaced with a substituent.
  • the "unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a fluorine atom.
  • ⁇ “Substituted or unsubstituted haloalkyl group” means that 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. It means a group, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the number of carbon atoms in the "unsubstituted haloalkyl group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18.
  • “Substituted haloalkyl group” means a group in which one or more hydrogen atoms of the "haloalkyl group” are replaced with a substituent.
  • the "substituted haloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl group” is further replaced with a substituent; Also included are groups in which one or more hydrogen atoms of a substituent in the "haloalkyl group” are further replaced with a substituent.
  • Specific examples of the "unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
  • a haloalkyl group is sometimes referred to as a halogenated alkyl group.
  • 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 alkoxy group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkoxy group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • ⁇ “Substituted or unsubstituted alkylthio group” A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkylthio group” described in specific example group G3. "unsubstituted alkyl group”. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkylthio group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18.
  • a specific example of the "substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryloxy group” described in specific example group G1. or an unsubstituted aryl group.
  • the number of ring carbon atoms in the "unsubstituted aryloxy group" is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted arylthio group” described in the specific example group G1.
  • G1 is the "substituted or unsubstituted arylthio group” described in the specific example group G1.
  • the number of ring carbon atoms in the "unsubstituted arylthio group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • ⁇ “Substituted or unsubstituted trialkylsilyl group” A specific example of the "trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group.” - A plurality of G3's in Si(G3) (G3) (G3) are mutually the same or different. The number of carbon atoms in each alkyl group of the "trialkylsilyl group” is from 1 to 50, preferably from 1 to 20, and more preferably from 1 to 6, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
  • an "aralkyl group” is a group in which the hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one embodiment of a “substituted alkyl group.”
  • An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group”, and the number of carbon atoms in the "unsubstituted aralkyl group” is determined unless otherwise specified herein. , 7 to 50, preferably 7 to 30, more preferably 7 to 18.
  • substituted or unsubstituted aralkyl groups include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ - Naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • the substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl group, unless otherwise specified herein.
  • the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, or a phenol group, unless otherwise specified herein.
  • Nanthrolinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-b
  • carbazolyl group is specifically any of the following groups unless otherwise specified in the specification.
  • the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise stated in the specification.
  • dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the specification.
  • the substituted or unsubstituted alkyl group described herein is preferably a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t- Butyl group, etc.
  • the "substituted or unsubstituted arylene group” described in this specification refers to 2 derived from the above “substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. It is the basis of valence.
  • the "substituted or unsubstituted arylene group” (specific example group G12), by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in specific example group G1
  • Examples include divalent groups derived from the derivatives.
  • the "substituted or unsubstituted divalent heterocyclic group” described herein refers to the "substituted or unsubstituted heterocyclic group" described above, in which one hydrogen atom on the heterocycle is removed. It is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocycle from the "substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include divalent groups derived by removing atoms.
  • the "substituted or unsubstituted alkylene group” described in this specification refers to 2 derived from the above "substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. It is the basis of valence.
  • a "substituted or unsubstituted alkylene group” (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group” described in specific example group G3. Examples include divalent groups derived from the derivatives.
  • the substituted or unsubstituted arylene group described herein is preferably a group represented by any of the following general formulas (TEMP-42) to (TEMP-68).
  • Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
  • * represents a binding site.
  • Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
  • Formulas Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents a binding site.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents a binding site.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein. It is.
  • Q 1 to Q 9 are each independently a hydrogen atom or a substituent.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • the set of two or more adjacent R 930 is one set. is a set of R 921 and R 922 , a set of R 922 and R 923 , a set of R 923 and R 924 , a set of R 924 and R 930 , a set of R 930 and R 925 , a set of R 925 and A set of R 926 , a set of R 926 and R 927 , a set of R 927 and R 928 , a set of R 928 and R 929 , and a set of R 929 and R 921 .
  • the above-mentioned "one or more sets” means that two or more sets of the above-mentioned two or more adjacent sets may form a ring at the same time.
  • R 921 and R 922 combine with each other to form ring Q A
  • R 925 and R 926 combine with each other to form ring Q B
  • the above general formula (TEMP-103) The anthracene compound represented is represented by the following general formula (TEMP-104).
  • a set of two or more adjacent items forms a ring is not only the case where a set of "two" adjacent items are combined as in the example above, but also the case where a set of "three or more adjacent items” form a ring. This also includes the case where two sets are combined.
  • R 921 and R 922 combine with each other to form a ring Q A
  • R 922 and R 923 combine with each other to form a ring Q C
  • the three adjacent to each other (R 921 , R 922 and R 923 ) combine with each other to form a ring and are condensed to the anthracene mother skeleton.
  • anthracene compound represented by the general formula (TEMP-103) is as follows: It is represented by the general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .
  • the "single ring” or “fused ring” that is formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even if “one set of two adjacent rings” forms a “monocycle” or “fused ring,” the “monocycle” or “fused ring” is a saturated ring, or Can form unsaturated rings.
  • ring Q A and ring Q B formed in the general formula (TEMP-104) are each a “monocyclic ring” or a “fused ring.”
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are "fused rings”.
  • Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring due to the condensation of ring Q A and ring Q C.
  • ring Q A in the general formula (TMEP-104) is a benzene ring
  • ring Q A is a monocyclic ring.
  • ring Q A in the general formula (TMEP-104) is a naphthalene ring
  • ring Q A is a fused ring.
  • Unsaturated ring includes an aromatic hydrocarbon ring, an aromatic heterocycle, and an aliphatic hydrocarbon ring having an unsaturated bond, that is, a double bond and/or triple bond in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having unsaturated bonds (for example, dihydropyran, imidazoline, pyrazoline, quinolidine, indoline, isoindoline, etc.).
  • the "saturated ring” includes an aliphatic hydrocarbon ring having no unsaturated bond or a non-aromatic heterocycle having no unsaturated bond.
  • aromatic hydrocarbon ring examples include structures in which the groups listed as specific examples in specific example group G1 are terminated with hydrogen atoms.
  • aromatic heterocycle include structures in which the aromatic heterocyclic group listed as a specific example in specific example group G2 is terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G6 are terminated with hydrogen atoms.
  • "Form a ring" means to form a ring with only a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more arbitrary atoms.
  • the ring Q A shown in the general formula (TEMP-104) formed by R 921 and R 922 bonding to each other is a carbon atom of the anthracene skeleton to which R 921 is bonded, and an anthracene bond to which R 922 is bonded. It means a ring formed by a carbon atom of the skeleton and one or more arbitrary atoms.
  • R 921 and R 922 form a ring Q A
  • the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms.
  • R 921 and R 922 form a monocyclic unsaturated ring
  • the ring formed by R 921 and R 922 is a benzene ring.
  • any atom is preferably at least one atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom.
  • any atom for example, in the case of a carbon atom or a nitrogen atom
  • a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent” described below.
  • the ring formed is a heterocycle.
  • "one or more arbitrary atoms" constituting a monocyclic ring or a condensed ring are preferably 2 to 15 atoms, more preferably 3 to 12 atoms.
  • a “monocycle” is preferred among “monocycle” and “fused ring.” Unless otherwise specified herein, the "unsaturated ring” is preferred between the “saturated ring” and the “unsaturated ring”. Unless otherwise stated herein, a “monocycle” is preferably a benzene ring. Unless otherwise stated herein, an “unsaturated ring” is preferably a benzene ring.
  • one or more pairs of two or more adjacent groups are “bonded with each other to form a substituted or unsubstituted monocycle” or “bonded with each other to form a substituted or unsubstituted fused ring”
  • one or more of the pairs of two or more adjacent atoms are bonded to each other to form a bond with a plurality of atoms of the parent skeleton and one or more of the 15 or more atoms.
  • a substituted or unsubstituted "unsaturated ring” is formed with at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the substituent is, for example, the "arbitrary substituent” described below.
  • Specific examples of the substituent in the case where the above-mentioned “single ring” or “fused ring” has a substituent are the substituents described in the section of "Substituent described herein” above.
  • the substituent is, for example, the "arbitrary substituent” described below.
  • substituents in the case where the above-mentioned "single ring” or “fused ring” has a substituent are the substituents described in the section of "Substituent described herein" above. The above applies to cases in which "one or more sets of two or more adjacent rings combine with each other to form a substituted or unsubstituted monocycle," and “one or more sets of two or more adjacent rings.” are combined with each other to form a substituted or unsubstituted condensed ring ("the case where they are combined to form a ring").
  • the substituent in the case of "substituted or unsubstituted” (herein referred to as "arbitrary substituent")
  • arbitrary substituent For example, unsubstituted alkyl group having 1 to 50 carbon atoms, unsubstituted alkenyl group having 2 to 50 carbon atoms, unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms,
  • R 901s When two or more R 901s exist, the two or more R 901s are the same or different, When two or more R 902s exist, the two or more R 902s are the same or different, When two or more R 903s exist, the two or more R 903s are the same or different, When two or more R 904s exist, the two or more R 904s are the same or different, When two or more R 905s exist, the two or more R 905s are the same or different, When two or more R 906s exist, the two or more R 906s are the same or different, When two or more R 907s exist, the two or more R 907s are the same or different.
  • the substituent in the case of "substituted or unsubstituted” is an alkyl group having 1 to 50 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the case of "substituted or unsubstituted” is an alkyl group having 1 to 18 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may form a "saturated ring" or "unsaturated ring", preferably a substituted or unsubstituted saturated ring. Forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
  • any substituent may further have a substituent.
  • the substituents that the arbitrary substituents further have are the same as the above arbitrary substituents.
  • the numerical range expressed using "AA-BB” has the numerical value AA written before “AA-BB” as the lower limit, and the numerical value BB written after "AA-BB”. means a range that includes as an upper limit value.
  • R A is a hydrogen atom or a substituent R.
  • Ar 1 and Ar 2 are each independently, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 1 to L 3 are each independently, single bond, A substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
  • n1 is an integer of 0 to 4 (preferably 0 to 2, more preferably 0 or 1), and when n1 is 0, (L 1 ) n1 is a single bond.
  • the plurality of L 1s may be the same or different.
  • n2 is an integer of 0 to 4 (preferably 0 to 2, more preferably 0 or 1), and when n2 is 0, (L 2 ) n2 is a single bond.
  • n3 is an integer of 0 to 4 (preferably 0 to 2, more preferably 0 or 1), and when n3 is 0, (L 3 ) n3 is a single bond.
  • the plurality of L 3s may be the same or different.
  • the pair of R 3 and R 4 may be bonded to each other to form a substituted or unsubstituted benzene ring, or may not be bonded to each other.
  • the pair of R 5 and R 6 may be bonded to each other to form a substituted or unsubstituted benzene ring, or may not be bonded to each other.
  • R 1 , R 2 , R 3 and R 4 that do not bond to each other, and R 5 and R 6 that do not bond to each other are each independently a hydrogen atom or a substituent R.
  • the pair R 1 and R 2 do not bond to each other.
  • the pair R 4 and R 5 do not bond to each other.
  • X 11 is O or S. Any one of R 11 to R 14 is a single bond that binds to (L 3 ) n3 . (L 3 ) R 11 to R 14 that are not single bonds bonded to n3 are hydrogen atoms. One or more sets of two or more adjacent ones of R 15 to R 18 are bonded to each other to form a substituted or unsubstituted benzene ring, or are not bonded to each other. In the case of "substituted or unsubstituted" in the benzene ring, the substituent is the substituent X. R 15 to R 18 that are not bonded to each other are each independently a hydrogen atom or a substituent X.
  • the substituent X is Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms and not containing a nitrogen atom
  • the substituent R is Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted
  • R 901 to R 907 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more R 901 to R 907 are present, each of the two or more R 901 to R 907 may be the same or different. ]
  • any one of R 11 to R 14 is a single bond bonded to (L 3 ) n3
  • R 12 is a single bond bonded to (L 3 ) n3 .
  • the carbon atom to which R 12 is bonded and (L 3 ) n3 are directly bonded via a single bond. That is, the carbon atom to which R 12 is bonded and the naphthalene ring are bonded via (L 3 ) n3 .
  • (L 3 ) When n3 is a single bond, the carbon atom to which R 12 is bonded and the naphthalene ring are directly bonded via a single bond.
  • naphthalene ring in the explanation is a phenanthrene ring
  • the two sets of R 3 and R 4 and the set of R 5 and R 6 are bonded to each other to form a benzene ring
  • the "naphthalene ring” in the above explanation is The "naphthalene ring” becomes a triphenylene ring.
  • one or more of the adjacent pairs may be bonded to each other to form a substituted or unsubstituted monocycle, and They may be combined to form a substituted or unsubstituted fused ring.
  • L 1 when there is a plurality of L 1 is 2 or more, one or more of the adjacent pairs may be bonded to each other to form a substituted or unsubstituted monocycle, and They may be combined to form a substituted or unsubstituted fused ring.
  • L 1 when n1 is 2 or more, one or more of the adjacent pairs may be bonded to each other to form a substituted or unsubstituted monocycle, and They may be combined to form a substituted or unsubstituted fused ring.
  • one or more of the adjacent pairs may be bonded to each other to form a substituted or unsubstituted monocycle; They may be combined to form a substituted or unsubstituted fused ring.
  • the pair R 16 and R 17 are not bonded to each other.
  • the pair of R 15 and R 16 are bonded to each other to form a substituted or unsubstituted benzene ring, or are not bonded to each other.
  • the pair of R 17 and R 18 are bonded to each other to form a substituted or unsubstituted benzene ring, or are not bonded to each other.
  • R 15 to R 18 that are not bonded to each other are hydrogen atoms.
  • R A is a hydrogen atom.
  • the compound represented by formula (1) is a compound selected from compounds represented by formulas (11) to (13) below.
  • Ar 1 , Ar 2 , L 1 to L 3 , n1, n2, n3, R 1 to R 6 , X 11 , and R 11 to R 14 are as defined in formula (1) above.
  • R 111 to R 114 are each independently a hydrogen atom or a substituent X.
  • Ar 1 , Ar 2 , L 1 to L 3 , n1, n2, n3, R 1 to R 6 , X 11 , and R 11 to R 14 are as defined in formula (1) above.
  • R 121 to R 126 are each independently a hydrogen atom or a substituent X.
  • Ar 1 , Ar 2 , L 1 to L 3 , n1, n2, n3, R 1 to R 6 , X 11 , and R 11 to R 14 are as defined in formula (1) above.
  • R 131 to R 136 are each independently a hydrogen atom or a substituent X.
  • Substituent X is as defined in formula (1) above.
  • R 12 is a single bond that binds to (L 3 ) n3 .
  • R 111 to R 114 in formula (11) are hydrogen atoms.
  • R 121 to R 126 in formula (12) are hydrogen atoms.
  • R 131 to R 136 in formula (13) are hydrogen atoms.
  • the compound represented by formula (1) is a compound selected from compounds represented by formulas (11-1) to (13-1) below.
  • Ar 1 , Ar 2 , L 1 to L 3 , R 1 to R 6 , X 11 , and R 111 to R 114 are as defined in formula (11) above.
  • R 115 to R 117 are hydrogen atoms.
  • Ar 1 , Ar 2 , L 1 to L 3 , R 1 to R 6 , X 11 , and R 121 to R 126 are as defined in formula (12) above.
  • R 127 to R 129 are hydrogen atoms.
  • Ar 1 , Ar 2 , L 1 to L 3 , R 1 to R 6 , X 11 , and R 131 to R 136 are as defined in formula (13) above.
  • R 137 to R 139 are hydrogen atoms.
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
  • L 3 is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted monovalent hetero group having 5 to 18 ring atoms. It is a ring group.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.
  • R 1 -R 6 are hydrogen atoms.
  • the substituent in the case of "substituted or unsubstituted" and the substituent R are: an alkyl group having 1 to 50 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the case of "substituted or unsubstituted" and the substituent R are: an alkyl group having 1 to 18 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
  • the compound according to one aspect of the present invention does not have a deuterium atom in the molecule as a hydrogen atom.
  • the proportion of deuterium atoms is the natural abundance ratio with respect to the total of light hydrogen atoms and deuterium atoms. It means that:
  • the compound according to one embodiment of the present invention that does not have a deuterium atom in its molecule as a hydrogen atom may contain deuterium atoms in a proportion lower than the natural abundance ratio. It can be confirmed by a nuclear magnetic resonance apparatus that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms is less than the natural abundance ratio.
  • the compound according to one aspect of the present invention has at least one deuterium atom as a hydrogen atom in the molecule.
  • R A is a hydrogen atom in formula (1), A hydrogen atom possessed by RA , which is a substituent R, R 1 to R 6 which are hydrogen atoms, Hydrogen atoms possessed by R 1 to R 6 as substituents R, A hydrogen atom possessed by a substituted or unsubstituted benzene ring formed by the combination of R 3 and R 4 , A hydrogen atom possessed by a substituted or unsubstituted benzene ring formed by the combination of R 5 and R 6 , R 11 to R 14 are hydrogen atoms, R 15 to R 18 which are hydrogen atoms, Hydrogen atoms possessed by R 15 to R 18 which are substituents X, A hydrogen atom possessed by a substituted or unsubstituted benzene ring formed by bonding one or more adjacent sets of two or more of R 15 to R 18 , The hydrogen atom that Ar 1 has, A hydrogen atom possessed by Ar2 , The hydrogen atom that L 1 has
  • R 11 to R 14 are hydrogen atoms in formula (1), R 15 to R 18 which are hydrogen atoms, Hydrogen atoms possessed by R 15 to R 18 which are substituents X, A hydrogen atom possessed by a substituted or unsubstituted benzene ring formed by bonding one or more pairs of two or more adjacent ones of R 15 to R 18 , At least one of them is a deuterium atom.
  • R 11 to R 14 are hydrogen atoms in formula (1), R 15 to R 18 which are hydrogen atoms, Hydrogen atoms possessed by R 15 to R 18 which are substituents X, A hydrogen atom contained in a substituted or unsubstituted benzene ring formed by bonding one or more adjacent sets of two or more of R 15 to R 18 is a deuterium atom.
  • a deuterium atom as a hydrogen atom
  • a hydrogen atom is a deuterium atom
  • the proportion of atoms is higher than the natural abundance ratio. It can be confirmed by a nuclear magnetic resonance apparatus that the proportion of deuterium atoms in the total of light hydrogen atoms and deuterium atoms is higher than the natural abundance ratio.
  • the compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions and raw materials depending on the target product.
  • the compound according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material for an electron transport band of an organic EL device.
  • An organic EL element according to one embodiment of the present invention will be described.
  • An organic EL element according to one aspect of the present invention includes a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers.
  • One layer includes a compound according to one embodiment of the present invention (a compound represented by formula (1)).
  • an organic EL device includes an anode, a light-emitting layer, an electron transport zone, and a cathode in this order, and the electron transport zone is composed of a compound (formula (1)) according to one embodiment of the present invention. )).
  • the electron transport zone is formed by forming a first layer (also referred to as "first electron transport layer” or “hole blocking layer”) and a second layer ("second electron transport layer”) from the light emitting layer side. ) in this order, and the first layer contains the compound represented by formula (1).
  • first layer also referred to as "first electron transport layer” or “hole blocking layer”
  • second electron transport layer the first layer contains the compound represented by formula (1).
  • the second layer in this case, for example, the structure of the electron transport layer described later can be applied.
  • a typical element configuration of the organic EL element is a structure in which the following structures are laminated on a substrate.
  • Anode/emissive layer/electron transport zone/cathode (2) Anode/hole transport zone/emissive layer/electron transport zone/cathode ("/" indicates that each layer is stacked adjacent to each other.)
  • the electron transport zone usually consists of one or more layers selected from an electron injection layer and an electron transport layer.
  • the hole transport zone usually consists of one or more layers selected from a hole injection layer and a hole transport layer.
  • An organic EL device 1 includes a substrate 2, an anode 3, a light emitting layer 5, a cathode 10, a hole transport zone 4 between the anode 3 and the light emitting layer 5, and a light emitting layer. 5 and an electron transport zone 6 between the cathode 10 and the cathode 10.
  • the substrate is used as a support for the light emitting device.
  • the substrate for example, glass, quartz, plastic, etc. can be used.
  • a flexible substrate may be used.
  • the flexible substrate refers to a bendable (flexible) substrate, and includes, for example, a plastic substrate made of polycarbonate or polyvinyl chloride.
  • anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more).
  • a metal for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene.
  • ITO indium oxide-tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide indium oxide-zinc oxide
  • tungsten oxide indium oxide containing zinc oxide
  • graphene graphene.
  • gold gold
  • platinum platinum
  • nitrides of metal materials eg, titanium nitride
  • the hole injection layer is a layer containing a substance with high hole injection properties.
  • Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, aromatic amine compounds, or high molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used.
  • the hole transport layer is a layer containing a substance with high hole transport properties.
  • aromatic amine compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • any material other than these may be used as long as it has a higher transportability for holes than for electrons.
  • the layer containing the substance with high hole transport properties is not limited to a single layer, and may be a stack of two or more layers made of the above substance.
  • the light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used for the light-emitting layer.
  • a highly luminescent substance a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as a highly luminescent substance.
  • a fluorescent compound is a compound capable of emitting light from a singlet excited state
  • a phosphorescent compound is a compound capable of emitting light from a triplet excited state.
  • blue fluorescent material that can be used in the light emitting layer
  • green fluorescent material that can be used in the light emitting layer
  • aromatic amine derivatives and the like can be used.
  • Tetracene derivatives, diamine derivatives, etc. can be used as red fluorescent materials that can be used in the light emitting layer.
  • Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue-based phosphorescent materials that can be used in the light-emitting layer.
  • An iridium complex or the like is used as a green phosphorescent material that can be used in the light emitting layer.
  • Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red-colored phosphorescent materials that can be used in the light-emitting layer.
  • the light-emitting layer may have a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material).
  • Various substances can be used to disperse highly luminescent substances, and the lowest unoccupied orbital level (LUMO level) is higher than that of highly luminescent substances, and the highest occupied orbital level (LUMO level) is higher than that of highly luminescent substances. It is preferable to use a substance with a low HOMO level.
  • Substances (host materials) for dispersing highly luminescent substances include 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, 2) oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives. Heterocyclic compounds, 3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, 4) aromatic amine compounds such as triarylamine derivatives, or fused polycyclic aromatic amine derivatives. used.
  • the electron transport layer is a layer containing a substance with high electron transport properties.
  • the electron transport layer contains 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. can be used.
  • the electron transport layer may or may not contain the other substances described above in addition to the compound according to one embodiment of the present invention (compound represented by formula (1)). good.
  • the electron injection layer is a layer containing a substance with high electron injection properties.
  • the electron injection layer contains lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 8-hydroxyquinolinolato-lithium (Liq), etc. metal complex compounds, alkali metals such as lithium oxide (LiO x ), alkaline earth metals, or compounds thereof can be used.
  • cathode For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, mixtures thereof, etc. with a small work function (specifically, 3.8 eV or less).
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium ( Examples include alkaline earth metals such as Ca), strontium (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • the cathode is usually formed by vacuum evaporation or sputtering.
  • a coating method, an inkjet method, etc. can be used.
  • the cathode when an electron injection layer is provided, can be formed using various conductive materials such as aluminum, silver, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the size of the work function. can be formed.
  • the thickness of each layer is not particularly limited, but it is generally from several nm to a few nanometers in order to suppress defects such as pinholes, keep the applied voltage low, and improve luminous efficiency. A range of 1 ⁇ m is preferred.
  • each layer is not particularly limited.
  • a conventionally known forming method such as a vacuum evaporation method or a spin coating method can be used.
  • Each layer such as the light-emitting layer is formed by a known coating method such as a vacuum evaporation method, a molecular beam evaporation method (MBE method), a dipping method using a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, or a roll coating method. It can be formed by
  • An electronic device includes an organic EL element according to one embodiment of the present invention.
  • Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, or personal computers, and light emitting devices such as lighting or vehicle lamps.
  • Comparative compounds used in the production of comparative organic EL devices are shown below.
  • An organic EL device was produced as follows. (Example 1) A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) 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 transparent electrodes is mounted on the substrate holder of a vacuum evaporation device, and first, compounds HT-1 and HI-1 are added to the surface on which the transparent electrodes are formed, covering the transparent electrodes.
  • ITO transparent electrode anode
  • Co-evaporation was performed so that the proportion of HI-1 was 3% by mass to form a first hole transport layer having a thickness of 10 nm.
  • Compound HT-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 80 nm.
  • Compound EBL-1 was deposited on the second hole transport layer to form a third hole transport layer (also referred to as "electron barrier layer") with a thickness of 5 nm.
  • Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the third hole transport layer so that the proportion of compound BD-1 was 4% by mass, and a film with a thickness of 25 nm was formed to emit light.
  • a layer was deposited.
  • Compound 1-1 was deposited on the light emitting layer to form a first electron transport layer (also referred to as a "hole blocking layer") with a thickness of 5 nm.
  • Compound ET-1 and Liq were co-deposited on the first electron transport layer such that the proportion of Liq was 50% by mass to form a second electron transport layer with a thickness of 20 nm.
  • Metal Yb was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.
  • Metallic Al was deposited on the electron injection layer to form a cathode with a thickness of 50 nm.
  • the element structure of the organic EL element of Example 1 is schematically shown as follows. ITO(130)/HT-1:HI-1(10:3%)/HT-1(80)/EBL-1(5)/BH-1:BD-1(25:4%)/Compound 1- 1(5)/ET-1:Liq(20:50%)/Yb(1)/Al(50)
  • the numbers in parentheses represent the film thickness (unit: nm). Moreover, the number expressed as a percentage in parentheses indicates the proportion (mass %) of the latter compound in the layer.
  • Example 2 An organic EL device was manufactured in the same manner as in Example 1 except that Compound 1-2 was used in forming the first electron transport layer.
  • Example 3 An organic EL device was manufactured in the same manner as in Example 1 except that Compound 1-3 was used in forming the first electron transport layer.
  • Example 4 An organic EL device was manufactured in the same manner as in Example 1 except that Compound 1-4 was used in forming the first electron transport layer.
  • Example 5 An organic EL device was manufactured in the same manner as in Example 1 except that Compound 1-5 was used in forming the first electron transport layer.
  • Example 1 An organic EL device was manufactured in the same manner as in Example 1 except that compound Ref-1 was used in forming the first electron transport layer.

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un composé représenté par la formule (1).
PCT/JP2023/027012 2022-07-28 2023-07-24 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique WO2024024726A1 (fr)

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US20190221751A1 (en) * 2016-09-22 2019-07-18 Rohm And Haas Electronic Materials Korea Ltd Organic electroluminescent device comprising an electron buffer layer and an electron transport layer
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KR20200068398A (ko) * 2018-12-05 2020-06-15 솔브레인 주식회사 화합물 및 이를 포함하는 유기 발광 소자
US20200403159A1 (en) * 2020-06-10 2020-12-24 Shanghai Tianma AM-OLED Co., Ltd. Compound, and organic light-emitting element, display panel and display device including the same
WO2021157636A1 (fr) * 2020-02-05 2021-08-12 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
WO2022035097A1 (fr) * 2020-08-14 2022-02-17 엘티소재주식회사 Dispositif électroluminescent organique et composition pour former une couche de matériau organique
WO2022173265A1 (fr) * 2021-02-15 2022-08-18 (주)피엔에이치테크 Composé organique luminescent et dispositif électroluminescent organique le comprenant
JP2023029297A (ja) * 2021-08-18 2023-03-03 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物、それを含む有機発光素子、および有機発光素子の有機物層用組成物

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US20190221751A1 (en) * 2016-09-22 2019-07-18 Rohm And Haas Electronic Materials Korea Ltd Organic electroluminescent device comprising an electron buffer layer and an electron transport layer
KR20180063710A (ko) * 2016-12-02 2018-06-12 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
JP2020501349A (ja) * 2016-12-09 2020-01-16 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロルミネセント化合物およびそれを含む有機エレクトロルミネセントデバイス
KR20200068398A (ko) * 2018-12-05 2020-06-15 솔브레인 주식회사 화합물 및 이를 포함하는 유기 발광 소자
WO2021157636A1 (fr) * 2020-02-05 2021-08-12 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
US20200403159A1 (en) * 2020-06-10 2020-12-24 Shanghai Tianma AM-OLED Co., Ltd. Compound, and organic light-emitting element, display panel and display device including the same
WO2022035097A1 (fr) * 2020-08-14 2022-02-17 엘티소재주식회사 Dispositif électroluminescent organique et composition pour former une couche de matériau organique
WO2022173265A1 (fr) * 2021-02-15 2022-08-18 (주)피엔에이치테크 Composé organique luminescent et dispositif électroluminescent organique le comprenant
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