WO2022215527A1 - Composé et élément électroluminescent organique - Google Patents

Composé et élément électroluminescent organique Download PDF

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WO2022215527A1
WO2022215527A1 PCT/JP2022/013600 JP2022013600W WO2022215527A1 WO 2022215527 A1 WO2022215527 A1 WO 2022215527A1 JP 2022013600 W JP2022013600 W JP 2022013600W WO 2022215527 A1 WO2022215527 A1 WO 2022215527A1
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裕 工藤
裕亮 糸井
聡美 田崎
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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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to novel compounds and organic electroluminescent devices.
  • Organic electroluminescence elements (hereinafter also referred to as "organic EL elements") are useful for displays and lighting applications.
  • An organic EL device usually includes organic layers such as a light-emitting layer and a charge transport layer, and various organic compound materials suitable for these layers are being developed (see, for example, Patent Document 1). .
  • Patent Documents 2 and 3 disclose the use of a compound having a specific structure in the light-emitting layer of an organic EL element.
  • An object of the present invention is to provide a compound that can produce a long-life organic EL device.
  • an anthracene-based compound having deuterium atoms as hydrogen atoms in the light-emitting layer of an organic EL device.
  • an anthracene-based compound having deuterium atoms as hydrogen atoms is produced, the number of deuterium atoms varies from compound to compound, and the deuteration rate of the hydrogen atoms in the compound is unstable. rice field. Therefore, there is a problem that the performance of the organic EL device using the compound is not stable.
  • Another object of the present invention is to provide a compound with excellent deuteration rate stability during production.
  • R 1 to R 8 are each independently a hydrogen atom or a substituent R;
  • R 105 to R 108 and R 101 to R 104 not bonded to L 2 are each independently a hydrogen atom or a substituent R.
  • L 1 and L 2 are each independently single bond, It is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 1 is It is 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.
  • Substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ) (Here, R 901 to R 907 are each independently 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, It is a substituted or unsubstituted ary
  • each of the two or more R 901 to R 907 may be the same or different.
  • 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-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the two or more substituents R may be the same or different.
  • at least two of R 105 to R 108 and R 101 to R 104 not bonded to L 2 are substituents X.
  • Substituent X is It is 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. At least one of the two substituents X has a deuterium atom. Two or more substituents X may be the same or different. ] 2. 2. The compound according to 1, wherein the compound represented by the formula (101) is a compound represented by the following formula (1). [In formula (1), One of R 101 , R 103 and R 104 binds to L 2 to form a single bond.
  • R 1 to R 8 are each independently a hydrogen atom or a substituent R;
  • R 102 and R 105 to R 108 , and R 101 , R 103 and R 104 not bonded to L 2 are each independently represented by a hydrogen atom, a substituent R, or the following formula (1A) or (1B) is a group.
  • X 1A is C(R 11A ).
  • X 2A is C(R 12A )(R 13A ).
  • R 11A and R 12A combine with each other to form ring a1.
  • R 13A is a hydrogen atom.
  • Ring a1 is It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
  • X 1B is C(R 11B )(R 12B ).
  • X 2B is C(R 13B )(R 14B ).
  • R 11B and R 13B are combined to form a substituted or unsubstituted heterocyclic ring b1 having 5 to 50 ring atoms.
  • R 12B and R 14B are hydrogen atoms.
  • L 1 and L 2 are each independently single bond, It is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 1 is It is 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.
  • Substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ) (Here, R 901 to R 907 are each independently 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, It is a substituted or unsubstituted ary
  • each of the two or more R 901 to R 907 may be the same or different.
  • 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-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • substituents R When two or more substituents R are present, the two or more substituents R may be the same or different.
  • R 102 and R 105 to R 108 and R 101 , R 103 and R 104 not bonded to L 2 are each independently represented by the formula (1A) or (1B) is the basis, At least one of the groups represented by formula (1A) or (1B) has a deuterium atom.
  • each of the two or more groups represented by formula (1A) or (1B) may be the same or different. . ] 3.
  • the compound according to claim 1, wherein the compound represented by the formula (101) is a compound represented by the following formula (2).
  • R 1 to R 8 and R 301 to R 307 are each independently a hydrogen atom or a substituent R; L 1 and L 2 are each independently It is a single bond or a substituted or unsubstituted phenylene group.
  • Ar 1 is A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ) (Here, R 901 to R 907 are each independently 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, It is a substituted or unsubstituted ary
  • each of the two or more R 901 to R 907 may be the same or different.
  • 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-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the two or more substituents R may be the same or different. However, the following condition 1 and condition 2 are satisfied.
  • R 301 to R 307 are each independently A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms having a deuterium atom, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms having a deuterium atom .
  • a long-life organic EL element can be provided.
  • ADVANTAGE OF THE INVENTION According to this invention, the compound which is excellent in the stability of a deuteration rate at the time of manufacture can be provided.
  • a hydrogen atom includes isotopes with different neutron numbers, ie, protium, deuterium, and tritium.
  • a hydrogen atom that is, a hydrogen atom, a deuterium atom, or Assume that the tritium atoms are bonded.
  • the number of ring-forming carbon atoms refers to a compound having a structure in which atoms are cyclically bonded (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). represents the number of carbon atoms among the atoms that When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same applies to the "number of ring-forming carbon atoms" described below 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.
  • the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms
  • the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
  • the number of ring-forming carbon atoms in the benzene ring substituted with the alkyl group is 6.
  • the naphthalene ring substituted with an alkyl group has 10 ring-forming carbon atoms.
  • the number of ring-forming atoms refers to compounds (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compound, and heterocyclic compound) represents the number of atoms constituting the ring itself. Atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom that constitutes a ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below unless otherwise specified.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of atoms forming the pyridine ring. Therefore, the number of ring-forming atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is 6.
  • the expression "substituted or unsubstituted XX to YY carbon number ZZ group” represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in the substituents.
  • "YY” is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • "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 represents a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group is a "substituted or unsubstituted ZZ group”. is a "substituted ZZ group”.
  • "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
  • a hydrogen atom in the "unsubstituted ZZ group” is a protium 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.
  • substituted in the case of "a 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-forming 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. .
  • the number of ring-forming atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified. be.
  • the number of carbon atoms in the "unsubstituted alkyl group” described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
  • the number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified. be.
  • the number of ring-forming carbon atoms in the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
  • the number of ring-forming 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 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
  • unsubstituted aryl group refers to the case where "substituted or unsubstituted aryl group” is “unsubstituted aryl group", and substituted aryl group is “substituted or unsubstituted aryl group” It refers to a "substituted aryl group”.
  • aryl group includes both "unsubstituted aryl group” and “substituted aryl group”.
  • a "substituted aryl group” means a group in which one or more hydrogen atoms of an "unsubstituted aryl group” are replaced with a substituent.
  • substituted aryl group examples include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group” of Specific Example Group G1A below is replaced with a substituent, and a substituted aryl group of Specific Example Group G1B below.
  • Examples include:
  • the examples of the "unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are only examples, and the “substituted aryl group” described herein includes the following specific examples A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group” of Group G1B is further replaced with a substituent, and the hydrogen atom of the substituent in the "substituted aryl group” of Specific Example Group G1B below Furthermore, groups substituted with substituents are also included.
  • aryl group (specific example group G1A): phenyl group, a p-biphenyl group, m-biphenyl group, an 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, benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chryseny
  • Substituted aryl group (specific example group G1B): an o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, an ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, an 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, a cyanophenyl group, a
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
  • a “heterocyclic group” as described herein is a monocyclic group or a condensed ring group.
  • a “heterocyclic group” as described herein is either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • specific examples of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic groups (specific example group G2A), and substituted heterocyclic groups ( Specific example group G2B) and the like can be mentioned.
  • unsubstituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”, and substituted heterocyclic group refers to “substituted or unsubstituted "Heterocyclic group” refers to a "substituted heterocyclic group”.
  • heterocyclic group refers to a "substituted heterocyclic group”.
  • a “substituted heterocyclic group” means 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 groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” of the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups of the following specific example group G2B. mentioned.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are only examples, and the "substituted heterocyclic group” described herein specifically includes A group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of Example Group G2B is further replaced with a substituent, and a substituent in the "substituted heterocyclic group" of Specific Example Group G2B A group in which the hydrogen atom of is further replaced with a substituent is also included.
  • Specific example group G2A includes, for example, the following nitrogen atom-containing unsubstituted heterocyclic groups (specific example group G2A1), oxygen atom-containing unsubstituted heterocyclic groups (specific example group G2A2), sulfur atom-containing unsubstituted (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • nitrogen atom-containing unsubstituted heterocyclic groups specifically example group G2A1
  • oxygen atom-containing unsubstituted heterocyclic groups specifically example group G2A2
  • sulfur atom-containing unsubstituted specifically example group G2A3
  • a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures 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 group containing a nitrogen atom (specific example group G2B1), substituted heterocyclic group containing an oxygen atom (specific example group G2B2), substituted heterocyclic ring containing a sulfur atom group (specific example group G2B3), and 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) as a substituent Including substituted groups (example group G2B4).
  • an unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, quinolyl group, an isoquinolyl group, cinnolyl group, a phthalazinyl group, a quinazolinyl
  • an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, azanaphthobenzofuranyl group and diazanaphthobenzofuranyl group;
  • thienyl group an unsubstituted heterocyclic group containing a sulfur atom
  • thienyl group a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothiopheny
  • 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 groups derived from the represented ring structures include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 .
  • a 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, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group and a biphenylquinazolinyl group;
  • a 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].
  • a substituted heterocyclic group containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
  • the "one or more hydrogen atoms of the monovalent heterocyclic group” means that at least one of the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, XA and YA is NH.
  • unsubstituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is “unsubstituted alkyl group”
  • substituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is It refers to a "substituted alkyl group”.
  • alkyl group includes both an "unsubstituted alkyl group” and a "substituted alkyl group”.
  • a “substituted alkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group” (specific example group G3A) are replaced with substituents, and substituted alkyl groups (specific examples Examples of group G3B) and the like can be mentioned.
  • the alkyl group in the "unsubstituted alkyl group” means a chain alkyl group.
  • the "unsubstituted alkyl group” includes a linear “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 only examples, and the "substituted alkyl group” described herein includes specific example group G3B A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group” of Specific Example Group G3B is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group” of Specific Example Group G3B is further replaced by a substituent included.
  • 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): a 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" described in the specification (specific example group G4) include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B) and the like.
  • unsubstituted alkenyl group refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group", "substituted alkenyl group” means "substituted or unsubstituted alkenyl group ” is a “substituted alkenyl group”.
  • alkenyl group simply referring to an “alkenyl group” includes both an “unsubstituted alkenyl group” and a “substituted alkenyl group”.
  • a “substituted alkenyl group” means 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 groups in which the following "unsubstituted alkenyl group” (specific example group G4A) has a substituent, and substituted alkenyl groups (specific example group G4B). be done.
  • Unsubstituted alkenyl group (specific example group G4A): a 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, a 2-methylallyl group and a 1,2-dimethylallyl group;
  • Substituted or unsubstituted alkynyl group Specific examples of the "substituted or unsubstituted alkynyl group" described in the specification (specific example group G5) include the following unsubstituted alkynyl groups (specific example group G5A).
  • the unsubstituted alkynyl group refers to the case where a "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group”.
  • alkynyl group simply referred to as an "alkynyl group” means "unsubstituted includes both "alkynyl group” and "substituted alkynyl group”.
  • a “substituted alkynyl group” means a group in which one or more hydrogen atoms in an "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 substituents.
  • Substituted or unsubstituted cycloalkyl group Specific examples of the "substituted or unsubstituted cycloalkyl group” described in the specification (specific example group G6) include the following unsubstituted cycloalkyl groups (specific example group G6A), and substituted cycloalkyl groups ( Specific example group G6B) and the like can be mentioned.
  • unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group” is “unsubstituted cycloalkyl group", and substituted cycloalkyl group refers to "substituted or unsubstituted "Cycloalkyl group” refers to a "substituted cycloalkyl group”.
  • cycloalkyl group means an "unsubstituted cycloalkyl group” and a “substituted cycloalkyl group.” including both.
  • a “substituted cycloalkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group” (specific example group G6A) are replaced with substituents, and substituted cycloalkyl groups (Specific example group G6B) and the like.
  • the examples of the "unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed here are only examples, and the "substituted cycloalkyl group” described herein specifically 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” of Example Group G6B is replaced with a substituent, and in the “substituted cycloalkyl group” of Specific Example Group G6B A group in which a hydrogen atom of a substituent is further replaced with a substituent is also included.
  • cycloalkyl group (specific example group G6A): a cyclopropyl group, cyclobutyl group, a cyclopentyl group, a 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 A group represented by -Si (R 901 ) (R 902 ) (R 903 )
  • Specific examples of the group represented by —Si(R 901 )(R 902 )(R 903 ) described in the 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) is 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 G1's in -Si(G1)(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -Si (G1) (G2) (G2) are the same or different from each other.
  • a plurality of G1's in -Si(G1)(G1)(G2) are the same or different from each other.
  • a plurality of G2 in -Si(G2)(G2)(G2) are the same or different from each other.
  • a plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other.
  • a plurality of G6 in -Si(G6)(G6)(G6) are the same or different from each other.
  • 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 of the group represented by -S-(R 905 ) described in the specification include: -S (G1), -S(G2), -S (G3) and -S (G6) are 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.
  • 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 G1's in -N(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -N(G2)(G2) are the same or different from each other.
  • a plurality of G3s in -N(G3)(G3) are the same or different from each other.
  • - the plurality of G6 in N (G6) (G6) are the same or different from each other
  • halogen atom described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • the "substituted or unsubstituted fluoroalkyl group” described herein 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 fluorine atom. 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 carbon number of the “unsubstituted fluoroalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • a "substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of a “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 atoms of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and A group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group” is further replaced with a substituent is also included.
  • Specific examples of the "unsubstituted fluoroalkyl group” include groups in which one or more hydrogen atoms in the above “alkyl group” (specific example group G3) are replaced with fluorine atoms.
  • Substituted or unsubstituted haloalkyl group "Substituted or unsubstituted haloalkyl group” described herein 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 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 carbon number of the “unsubstituted haloalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • a "substituted haloalkyl group” means a group in which one or more hydrogen atoms of a “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 atoms of the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent group, and a “substituted A group in which one or more hydrogen atoms of the substituent in the "haloalkyl group of" is further replaced with a substituent is also included.
  • Specific examples of the "unsubstituted haloalkyl group” include groups in which one or more hydrogen atoms in the above “alkyl group” (specific example group G3) are replaced with halogen atoms.
  • a haloalkyl group may be referred to as a halogenated alkyl group.
  • Substituted or unsubstituted alkoxy 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 the "substituted or unsubstituted alkyl group".
  • the carbon number of the "unsubstituted alkoxy group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the 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 the "substituted or unsubstituted unsubstituted alkyl group".
  • the carbon number of the "unsubstituted alkylthio group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • Substituted or unsubstituted aryloxy group Specific examples of the “substituted or unsubstituted aryloxy group” described in this specification are groups represented by —O(G1), where G1 is the “substituted or an unsubstituted aryl group”.
  • the number of ring-forming carbon atoms in the "unsubstituted aryloxy group” is 6-50, preferably 6-30, more preferably 6-18, unless otherwise specified in the specification.
  • ⁇ "Substituted or unsubstituted trialkylsilyl group” Specific examples of the "trialkylsilyl group” described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the group described in Specific Example Group G3. It is a "substituted or unsubstituted alkyl group”. A plurality of G3s in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group” is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified in the specification.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the 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 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 unless otherwise specified herein. , 7-50, preferably 7-30, more preferably 7-18.
  • substituted or unsubstituted aralkyl group include a 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.
  • a substituted or unsubstituted aryl group described herein is preferably a 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, phenanthryl group , pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group,
  • substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenyl, unless otherwise stated herein.
  • nantholinyl 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-
  • a carbazolyl group is specifically any one of the following groups unless otherwise specified in the specification.
  • the (9-phenyl)carbazolyl group is specifically any one of the following groups, unless otherwise stated in the specification.
  • a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t- butyl group and the like.
  • the "substituted or unsubstituted arylene group” described herein is derived from the above "substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. is the base of the valence.
  • Specific examples of the “substituted or unsubstituted arylene group” include the “substituted or unsubstituted aryl group” described in specific example group G1 by removing one hydrogen atom on the aryl ring. Induced divalent groups and the like can be mentioned.
  • Substituted or unsubstituted divalent heterocyclic group Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group” described herein is the above “substituted or unsubstituted heterocyclic group” except that one hydrogen atom on the heterocyclic ring is removed. 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 heterocyclic ring from the "substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include divalent groups derived by removing atoms.
  • Substituted or unsubstituted alkylene group Unless otherwise specified, the "substituted or unsubstituted alkylene group” described herein is derived from the above “substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. is the base of the valence. Specific examples of the "substituted or unsubstituted alkylene group” (specific example group G14) include the "substituted or unsubstituted alkyl group” described in specific example group G3 by removing one hydrogen atom on the alkyl chain. Induced divalent groups and the like can be mentioned.
  • the substituted or unsubstituted arylene group described in this specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • * represents a binding site.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Formulas Q9 and Q10 may be linked together through 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 any group of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein 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.
  • R 921 and R 922 when “one or more pairs of two or more adjacent pairs of R 921 to R 930 are combined to form a ring", is a pair of R 921 and R 922 , a pair of R 922 and R 923 , a pair of R 923 and R 924 , a pair of R 924 and R 930 , a pair of R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R 929 and R 921 .
  • one or more pairs means that two or more of the groups consisting of two or more adjacent groups may form a ring at the same time.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 925 and R 926 are bonded together to form ring Q B
  • the general formula (TEMP-103) The represented anthracene compound is represented by the following general formula (TEMP-104).
  • a group consisting of two or more adjacent pairs forms a ring is not limited to the case where a group consisting of two adjacent "two” is combined as in the above example, but It also includes the case where a pair is combined.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 922 and R 923 are bonded together to form ring Q C
  • the adjacent three R 921 , R 922 and R 923
  • the anthracene compound represented by the general formula (TEMP-103) has It is represented by the general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “condensed ring” to be formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when “one pair of adjacent pairs" forms a “single ring” or a “fused ring", the “single ring” or “fused ring” is a saturated ring, or Unsaturated rings can be formed.
  • 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”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) form a condensed ring by condensing the ring Q A and the ring Q C. If ring Q A in the general formula (TMEP-104) is a benzene ring, ring Q A is monocyclic. When the ring Q A of the general formula (TMEP-104) is a naphthalene ring, the ring Q A is a condensed ring.
  • the "unsaturated ring” includes an aromatic hydrocarbon ring, an aromatic heterocyclic ring, and an aliphatic hydrocarbon ring having an unsaturated bond in the ring structure, that is, a double bond and/or a triple bond (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having unsaturated bonds (eg, dihydropyran, imidazoline, pyrazoline, quinolidine, indoline, isoindoline, etc.).
  • the "saturated ring” includes an aliphatic hydrocarbon ring having no unsaturated bonds or a non-aromatic heterocyclic ring having no unsaturated bonds.
  • aromatic hydrocarbon ring examples include structures in which the groups listed as specific examples in the specific example group G1 are terminated with a hydrogen atom.
  • aromatic heterocyclic ring examples include structures in which the aromatic heterocyclic groups listed 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 listed as specific examples in the specific example group G6 are terminated with a hydrogen atom.
  • the ring Q A formed by combining R 921 and R 922 shown in the general formula (TEMP-104) has the carbon atom of the anthracene skeleton to which R 921 is bonded and the anthracene skeleton to which R 922 is bonded. It means a ring formed by a skeleton carbon atom 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 bound, the carbon atom of the anthracene skeleton to which R 922 is bound, and four carbon atoms and form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.
  • the "arbitrary atom” is preferably at least one atom selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms, unless otherwise specified herein.
  • a bond that does not form a ring at any atom may be terminated with a hydrogen atom or the like, or may be substituted with an "optional substituent” described later. If it contains any atoms other than carbon atoms, then the ring formed is a heterocyclic ring.
  • “One or more arbitrary atoms" constituting a monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, unless otherwise specified in the specification.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above “monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section “Substituents described herein” above.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above "monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section "Substituents described herein" above. The above is the case where “one or more pairs of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic ring", and “one or more pairs of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted condensed ring"("bonded to form a ring").
  • the substituent in the case of “substituted or unsubstituted” is, 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 atom, cyano group, nitro group, a group selected from the group consisting of an unsubstituted aryl group
  • the two or more R 901 are the same or different from each other, when two or more R 902 are present, the two or more R 902 are the same or different from each other; when two or more R 903 are present, the two or more R 903 are the same or different from each other, when two or more R 904 are present, the two or more R 904 are the same or different from each other; when two or more R 905 are present, the two or more R 905 are the same or different from each other, when two or more R 906 are present, the two or more R 906 are the same or different from each other; When two or more R 907 are present, the two or more R 907 are the same or different from each other.
  • the substituents referred to above as "substituted or unsubstituted” are an alkyl group having 1 to 50 carbon atoms, It is 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 substituents referred to above as "substituted or unsubstituted” are an alkyl group having 1 to 18 carbon atoms, It is 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 an “unsaturated ring”, preferably a substituted or unsubstituted saturated 5 forming 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 have further substituents. Substituents further possessed by the optional substituents are the same as the above optional substituents.
  • the numerical range represented using “AA to BB” has the numerical value AA described before “AA to BB” as the lower limit, and the numerical value BB described after “AA to BB” as the upper limit.
  • a compound according to one embodiment of the present invention is represented by the following formula (101).
  • [In formula (101) One of R 101 to R 104 binds to L 2 to form a single bond.
  • R 1 to R 8 are each independently a hydrogen atom or a substituent R;
  • R 105 to R 108 and R 101 to R 104 not bonded to L 2 are each independently a hydrogen atom or a substituent R.
  • L 1 and L 2 are each independently single bond, It is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 1 is It is 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.
  • Substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ) (Here, R 901 to R 907 are each independently hydrogen atom, a substituted or unsubsti
  • each of the two or more R 901 to R 907 may be the same or different.
  • 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-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the two or more substituents R may be the same or different.
  • at least two of R 105 to R 108 and R 101 to R 104 not bonded to L 2 are substituents X.
  • Substituent X is It is 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. At least one of the two substituents X has a deuterium atom. Two or more substituents X may be the same or different. ]
  • a specific group “having a deuterium atom” means that at least one hydrogen atom of the group is a deuterium atom.
  • the phrase "the hydrogen atom is a deuterium atom” means that, in the hydrogen atom, the ratio of the deuterium atom to the total of the hydrogen atom and the deuterium atom is higher 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 protium atoms and deuterium atoms is higher than the natural abundance ratio.
  • each of the two or more R 941 to R 953 may be the same or different), a hydroxy group, It is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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" in the compound represented by formula (101) is an alkyl group having 1 to 50 carbon atoms, 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" in the compound represented by formula (101) is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 ring carbon atoms , and a monovalent heterocyclic group having 5 to 30 ring atoms.
  • the substituent in the case of "substituted or unsubstituted" in the compound represented by formula (101) is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms , and a monovalent heterocyclic group having 5 to 18 ring atoms.
  • the compound represented by formula (101) can be synthesized by following the examples and using known alternative reactions and raw materials suitable for the desired product.
  • Specific examples of the compound represented by formula (101) include specific examples of the compound represented by formula (1) and specific examples of the compound represented by formula (2), which will be described later. are only examples, and the compound represented by formula (101) is not limited to these specific examples.
  • the compound represented by the formula (101) is a compound represented by the following formula (1).
  • R 101 , R 103 and R 104 binds to L 2 to form a single bond.
  • R 1 to R 8 are each independently a hydrogen atom or a substituent R;
  • R 101 , R 103 and R 104 not bonded to L 2 are each independently represented by a hydrogen atom, a substituent R, or the following formula (1A) or (1B) is a group.
  • X 1A is C(R 11A ).
  • X 2A is C(R 12A )(R 13A ).
  • R 11A and R 12A combine with each other to form ring a1.
  • R 13A is a hydrogen atom.
  • Ring a1 is It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
  • X 1B is C(R 11B )(R 12B ).
  • X 2B is C(R 13B )(R 14B ).
  • R 11B and R 13B are combined to form a substituted or unsubstituted heterocyclic ring b1 having 5 to 50 ring atoms.
  • R 12B and R 14B are hydrogen atoms.
  • L 1 and L 2 are each independently single bond, It is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 1 is It is 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.
  • Substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ) (Here, R 901 to R 907 are each independently 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, It is a substituted or unsubstituted ary
  • each of the two or more R 901 to R 907 may be the same or different.
  • 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-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • substituents R When two or more substituents R are present, the two or more substituents R may be the same or different.
  • R 102 and R 105 to R 108 and R 101 , R 103 and R 104 not bonded to L 2 are each independently represented by the formula (1A) or (1B) is the basis, At least one of the groups represented by formula (1A) or (1B) has a deuterium atom.
  • each of the two or more groups represented by formula (1A) or (1B) may be the same or different. . ]
  • a specific group “having a deuterium atom” means that at least one hydrogen atom of the group is a deuterium atom.
  • the phrase "the hydrogen atom is a deuterium atom” means that, in the hydrogen atom, the ratio of the deuterium atom to the total of the hydrogen atom and the deuterium atom is higher 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 protium atoms and deuterium atoms is higher than the natural abundance ratio.
  • the compound according to the present invention has at least two groups represented by formula (1A) or (1B) on the dibenzofuran skeleton, as can be seen from the definition of formula (1) above.
  • Having at least two groups represented by formula (1A) or (1B) on the dibenzofuran skeleton increases the glass transition temperature of the film when the compound is formed into a film, thereby improving film stability. do.
  • the dibenzofuran skeleton is involved in carrier transport in the compound represented by formula (1).
  • at least one group represented by formula (1A) or (1B) has a deuterium atom, thereby improving the carrier resistance of the dibenzofuran skeleton.
  • a long-life organic EL device can be manufactured.
  • L2 is a single bond.
  • the compound represented by formula (1) is a compound represented by any one of the following formulas (1-1) to (1-3).
  • R 1 to R 8 and Ar 1 are as defined in Formula (1) above.
  • R 102 to R 108 are each independently a hydrogen atom, a substituent R, or a group represented by formula (1A) or (1B). At least two of R 102 to R 108 are each independently a group represented by formula (1A) or (1B).
  • R 1 to R 8 and Ar 1 are as defined in formula (1) above.
  • R 101 to R 102 and R 104 to R 108 are each independently a hydrogen atom, a substituent R, or a group represented by formula (1A) or (1B).
  • R 101 to R 102 and R 104 to R 108 are each independently a group represented by formula (1A) or (1B).
  • R 1 to R 8 and Ar 1 are as defined in formula (1) above.
  • R 101 to R 103 and R 105 to R 108 are each independently a hydrogen atom, a substituent R, or a group represented by formula (1A) or (1B).
  • At least two of R 101 to R 103 and R 105 to R 108 are each independently a group represented by formula (1A) or (1B).
  • Substituent R is as defined in formula (1) above. ]
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • Ar 1 is It is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.
  • Ar 1 is It is a substituted or unsubstituted phenyl group.
  • the group represented by formula (1A) or (1B) is It is a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms and having a deuterium atom.
  • the group represented by formula (1A) or (1B) is A substituted or unsubstituted phenyl group having a deuterium atom, or a substituted or unsubstituted naphthyl group having a deuterium atom.
  • the group represented by formula (1A) or (1B) is A substituted or unsubstituted phenyl group having a deuterium atom.
  • R 1 -R 8 are hydrogen atoms.
  • the compound represented by formula (1) is a compound represented by any one of the following formulas (1-11) to (1-15).
  • R 161 , R 165 , R 171 and R 175 are hydrogen atoms.
  • R 102 to R 105 , R 108 , R 162 to R 164 , R 172 to R 174 , and R 201 to R 205 are each independently a hydrogen atom or a substituent R;
  • at least one of the hydrogen atoms of R 161 to R 165 as hydrogen atoms and the hydrogen atoms of R 162 to R 164 as substituents R is a deuterium atom.
  • At least one of the hydrogen atoms of R 171 to R 175 which are hydrogen atoms and the hydrogen atoms of R 172 to R 174 which are substituents R is a deuterium atom.
  • R 131 , R 135, R 161 and R 165 are hydrogen atoms.
  • R 102 , R 104 -R 105 , R 107 -R 108 , R 132 -R 134 , R 162 -R 164 , and R 201 -R 205 are each independently a hydrogen atom or a substituent R.
  • At least one of the hydrogen atoms R 131 to R 135 and the hydrogen atoms of the substituents R R 132 to R 134 is a deuterium atom.
  • At least one of the hydrogen atoms of R 161 to R 165 which are hydrogen atoms and the hydrogen atoms of R 162 to R 164 which are substituents R is a deuterium atom.
  • R 121 , R 125, R 161 and R 165 are hydrogen atoms.
  • R 101 , R 103 , R 105 , R 107 -R 108 , R 122 -R 124 , R 162 -R 164 , and R 201 -R 205 are each independently a hydrogen atom or a substituent R.
  • at least one of the hydrogen atoms R 121 to R 125 and the hydrogen atoms of the substituents R R 122 to R 124 is a deuterium atom.
  • At least one of the hydrogen atoms of R 161 to R 165 which are hydrogen atoms and the hydrogen atoms of R 162 to R 164 which are substituents R is a deuterium atom.
  • R 161 , R 165 , R 181 and R 185 are hydrogen atoms.
  • R 101 to R 102 , R 104 to R 105 , R 107 , R 162 to R 164 , R 182 to R 184 , and R 201 to R 205 are each independently a hydrogen atom or a substituent R; However, at least one of the hydrogen atoms of R 161 to R 165 as hydrogen atoms and the hydrogen atoms of R 162 to R 164 as substituents R is a deuterium atom.
  • At least one of hydrogen atoms of R 181 to R 185 which are hydrogen atoms and hydrogen atoms of R 182 to R 184 which are substituents R is a deuterium atom.
  • R 131 , R 135, R 171 and R 175 are hydrogen atoms.
  • R 102 , R 104 to R 106 , R 108 , R 132 to R 134 , R 172 to R 174 , and R 201 to R 205 are each independently a hydrogen atom or a substituent R; However, at least one of the hydrogen atoms R 131 to R 135 and the hydrogen atoms of the substituents R R 132 to R 134 is a deuterium atom.
  • At least one of the hydrogen atoms of R 171 to R 175 which are hydrogen atoms and the hydrogen atoms of R 172 to R 174 which are substituents R is a deuterium atom.
  • Substituent R is as defined in formula (1) above. ]
  • the compound represented by formula (1) is a compound represented by formula (1-11), (1-12), (1-13), or (1-15). .
  • the compound represented by formula (1) is a compound represented by formula (1-11), (1-12), or (1-15).
  • At least one of the hydrogen atoms R 201 to R 205 and the hydrogen atoms of the substituent R R 201 to R 205 is a deuterium atom. This makes it possible to obtain an organic EL element with a longer life.
  • each of the two or more R 941 to R 953 may be the same or different), a hydroxy group, It is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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" in the compound represented by formula (1) is an alkyl group having 1 to 50 carbon atoms, 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" in the compound represented by formula (1) is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 ring carbon atoms. , and a monovalent heterocyclic group having 5 to 30 ring atoms.
  • the substituent in the case of "substituted or unsubstituted" in the compound represented by formula (1) is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms. , and a monovalent heterocyclic group having 5 to 18 ring atoms.
  • the compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions and raw materials suitable for the desired product.
  • the compound represented by the formula (101) is a compound represented by the following formula (2).
  • Ar 1 is A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ) (Here, R 901 to R 907 are each independently 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, It is a substituted or unsubstituted ary
  • each of the two or more R 901 to R 907 may be the same or different.
  • 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-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the two or more substituents R may be the same or different. However, the following condition 1 and condition 2 are satisfied.
  • R 301 to R 307 are each independently A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms having a deuterium atom, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms having a deuterium atom .
  • R 1 to R 8 which are hydrogen atoms are not deuterium atoms.
  • a hydrogen atom is not a deuterium atom refers to the ratio of deuterium atoms to the total of deuterium atoms and deuterium atoms in the hydrogen atom (herein, “deuteration rate ) is below the natural abundance ratio. In other words, it means that the inclusion of deuterium atoms at a natural abundance ratio is permitted.
  • the natural abundance of deuterium atoms is, for example, 0.015% or less. It can be confirmed by a nuclear magnetic resonance apparatus that the ratio of deuterium atoms to the sum of protium atoms and deuterium atoms in the hydrogen atoms is equal to or less than the natural abundance ratio.
  • R 301 to R 307 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms having a deuterium atom, or a substituted or unsubstituted It is a monovalent heterocyclic group having 5 to 50 ring-forming atoms.”
  • a specific group “having a deuterium atom” means that at least one hydrogen atom of the group is a deuterium atom.
  • the hydrogen atom is a deuterium atom means that the ratio of the deuterium atom to the total of the hydrogen atom and the deuterium atom is higher 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 protium atoms and deuterium atoms is higher than the natural abundance ratio.
  • the hydrogen atom directly bonded to the anthracene skeleton is not a deuterium atom.
  • at least two substituents on the dibenzofuran skeleton have deuterium atoms. This stabilizes the deuteration rate of the hydrogen atoms in the compound during production of the compound.
  • the deuteration rate of the hydrogen atoms in the compound when manufacturing the compound can be evaluated by the method described in the Examples.
  • an organic EL device can be stably produced.
  • two of R 301 to R 307 are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms and having a deuterium atom.
  • two of R 301 to R 307 are each independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms and having a deuterium atom.
  • At least one of the hydrogen atoms that Ar 1 has is a deuterium atom.
  • the compound represented by formula (2) is a compound represented by any one of the following formulas (2-1) to (2-6).
  • R 1 to R 8 are as defined in formula (2) above.
  • R 301 to R 307 are each independently a hydrogen atom or a substituent R; provided that two of R 301 to R 307 are each independently A substituted or unsubstituted phenyl group having a deuterium atom, or a substituted or unsubstituted naphthyl group having a deuterium atom.
  • R 11 to R 15 each independently represent a hydrogen atom or a substituent R.
  • R 21 to R 29 are each independently a hydrogen atom or a substituent R.
  • R 31 to R 39 are each independently a hydrogen atom or a substituent R.
  • R 41 to R 49 are each independently a hydrogen atom or a substituent R.
  • R 51 to R 57 each independently represent a hydrogen atom or a substituent R.
  • R 61 to R 67 each independently represent a hydrogen atom or a substituent R.
  • Substituent R is as defined in formula (2) above. ]
  • two of R 301 to R 307 are each independently a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms and having a deuterium atom.
  • two of R 301 -R 307 are each independently A substituted or unsubstituted phenyl group having a deuterium atom.
  • two of R 303 -R 306 are each independently A substituted or unsubstituted phenyl group having a deuterium atom.
  • two of R 304 to R 306 are each independently A substituted or unsubstituted phenyl group having a deuterium atom.
  • R 1 -R 8 are hydrogen atoms.
  • the compound represented by the formula (2) is a compound represented by any one of the following formulas (2-11) to (2-15).
  • R 11 to R 15 , R 301 , R 304 to R 307 , R 321 to R 325 and R 331 to R 335 are each independently a hydrogen atom or a substituent R; However, at least one of the hydrogen atoms R 11 to R 15 and the hydrogen atoms of the substituent R R 11 to R 15 is a deuterium atom. At least one of the hydrogen atoms R 321 to R 325 and the hydrogen atoms of the substituents R 321 to R 325 is a deuterium atom.
  • At least one of the hydrogen atoms R 331 to R 335 and the hydrogen atoms of the substituent R R 331 to R 335 is a deuterium atom.
  • R 11 to R 15 , R 301 to R 302 , R 305 to R 307 , R 331 to R 335 , and R 341 to R 345 are each independently a hydrogen atom or a substituent R; However, at least one of the hydrogen atoms R 11 to R 15 and the hydrogen atoms of the substituent R R 11 to R 15 is a deuterium atom. At least one of the hydrogen atoms R 331 to R 335 and the hydrogen atoms of the substituent R R 331 to R 335 is a deuterium atom.
  • At least one of the hydrogen atoms R 341 to R 345 and the hydrogen atoms of the substituent R R 341 to R 345 is a deuterium atom.
  • R 11 to R 15 , R 301 to R 304 , R 307 , R 351 to R 355 and R 361 to R 365 are each independently a hydrogen atom or a substituent R; However, at least one of the hydrogen atoms R 11 to R 15 and the hydrogen atoms of the substituent R R 11 to R 15 is a deuterium atom. At least one of the hydrogen atoms R 351 to R 355 and the hydrogen atoms of the substituents R 351 to R 355 is a deuterium atom.
  • At least one of the hydrogen atoms R 361 to R 365 and the hydrogen atoms of the substituents R 361 to R 365 is a deuterium atom.
  • R 11 to R 15 , R 301 to R 302 , R 304 , R 306 to R 307 , R 331 to R 335 , and R 351 to R 355 are each independently a hydrogen atom or a substituent R; However, at least one of the hydrogen atoms R 11 to R 15 and the hydrogen atoms of the substituent R R 11 to R 15 is a deuterium atom.
  • At least one of the hydrogen atoms R 331 to R 335 and the hydrogen atoms of the substituent R R 331 to R 335 is a deuterium atom. At least one of the hydrogen atoms R 351 to R 355 and the hydrogen atoms of the substituents R 351 to R 355 is a deuterium atom.
  • R 11 to R 15 , R 301 to R 303 , R 305 , R 307 , R 341 to R 345 , and R 361 to R 365 are each independently a hydrogen atom or a substituent R; However, at least one of the hydrogen atoms R 11 to R 15 and the hydrogen atoms of the substituent R R 11 to R 15 is a deuterium atom.
  • At least one of the hydrogen atoms R 341 to R 345 and the hydrogen atoms of the substituent R R 341 to R 345 is a deuterium atom. At least one of the hydrogen atoms R 361 to R 365 and the hydrogen atoms of the substituents R 361 to R 365 is a deuterium atom.
  • Substituent R is as defined in formula (2) above. ]
  • the compound represented by formula (2) is a compound represented by any one of formulas (2-13) to (2-15).
  • the compound represented by the formula (2) is the compound represented by the formula (2-13).
  • R 301 to R 304 and R 307 are hydrogen atoms.
  • each of the two or more R 941 to R 953 may be the same or different), a hydroxy group, It is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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" in the compound represented by formula (2) is an alkyl group having 1 to 50 carbon atoms, 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" in the compound represented by formula (2) is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 ring carbon atoms. , and a monovalent heterocyclic group having 5 to 30 ring atoms.
  • the substituent in the case of "substituted or unsubstituted" in the compound represented by formula (2) is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms , and a monovalent heterocyclic group having 5 to 18 ring atoms.
  • the compound represented by formula (2) can be synthesized by following the examples and using known alternative reactions and raw materials suitable for the desired product.
  • the compound according to one embodiment of the present invention is useful as a material for an organic EL device, useful as a material for a light-emitting layer of an organic EL device, and particularly useful as a host material for the light-emitting layer.
  • the compound according to the first embodiment of the present invention in the light-emitting layer of an organic EL device it is possible to obtain a long-life organic EL device.
  • the compound according to the second embodiment of the present invention is excellent in the stability of the deuteration rate during production. By using the compound in the light-emitting layer of an organic EL device, it is possible to stably obtain an organic EL device.
  • An organic EL element according to an aspect of the present invention has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the one or more organic layers
  • One layer contains the compound represented by the formula (101).
  • An organic EL device has a cathode, an anode, and one or more light-emitting layers disposed between the cathode and the anode, and at least one of the one or more light-emitting layers
  • One layer contains the compound represented by the formula (101).
  • An organic EL element 1 includes a substrate 2, an anode 3, a light emitting layer 5 which is an organic layer, a cathode 10, an organic layer 4 between the anode 3 and the light emitting layer 5, It has an organic layer 6 between the light emitting layer 5 and the cathode 10 .
  • Each of the organic layer 4 and the organic layer 6 may be a single layer or may consist of multiple layers.
  • the organic layer 4 may also contain a hole transport zone.
  • the hole transport zone may include hole injection layers, hole transport layers, electron blocking layers, and the like.
  • the organic layer 6 may contain an electron transport zone.
  • the electron transport zone may include electron injection layers, electron transport layers, hole blocking layers, and the like.
  • the compound according to one embodiment of the present invention (compound represented by Formula (101)) is included in the organic layer 4, the light-emitting layer 5, or the organic layer 6. In one embodiment, a compound according to one aspect of the present invention is included in light-emitting layer 5 .
  • the compound represented by formula (101) is used as the host material.
  • the dopant material (guest material) used in combination therewith is not particularly limited.
  • An organic EL device wherein at least one of the one or more light-emitting layers contains a compound represented by formula (101) and a dopant material, except that the Conventionally known materials and element configurations can be applied as long as the effects of the above are not impaired.
  • a typical element configuration of the organic EL element of the present invention is as follows. (1) Anode/light emitting layer/cathode (2) Anode/hole injection layer/light emitting layer/cathode (3) Anode/light emitting layer/electron injection/transport layer/cathode (4) Anode/hole injection layer/light emitting layer /electron injection/transport layer/cathode (5) anode/organic semiconductor layer/light-emitting layer/cathode (6) anode/organic semiconductor layer/electron barrier layer/light-emitting layer/cathode (7) anode/organic semiconductor layer/light-emitting layer/ Adhesion improving layer/cathode (8) anode/hole injection/transport layer/light emitting layer/electron injection/transport layer/cathode (9) anode/insulating layer/light emitting layer/insulating layer/cathode (10) anode/inorganic semiconductor layer /insulating layer/light-emitting layer/
  • hole injection/transport layer means “at least one of a hole injection layer and a hole transport layer”
  • electron injection/transport layer means “an electron injection layer and an electron means “at least one of the transport layers”.
  • the organic EL device according to one aspect of the present invention has an electron transport layer between the cathode and the light-emitting layer.
  • the electron transport layer contains a compound represented by the following formula (3).
  • X 31A to X 33A are each independently CR 34A or a nitrogen atom.
  • R 34A is a hydrogen atom or a substituent R; At least two of X 31A to X 33A are nitrogen atoms.
  • R 31A to R 33A are each independently It is a hydrogen atom or a substituent R.
  • Substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ) (Here, R 901 to R 907 are each independently 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, It is a substituted or unsubstituted ary
  • each of the two or more R 901 to R 907 may be the same or different.
  • 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-forming carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • substituents R may be the same or different.
  • the compound represented by formula (3) is a compound represented by formula (31) below.
  • X 31A to X 33A , R 31A and R 32A are as defined in formula (3) above.
  • L31A is single bond, It is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 31A is It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • Ar 31A is a group represented by formula (32) below.
  • X 34A is O, S, N(R 321A ), or C(R 322A )(R 323A ).
  • R 311A to R 318A and R 321A to R 323A is a single bond that binds to L 31A .
  • One or more pairs of adjacent pairs of two or more of R 311A to R 318A that are not single bonds bonded to L 31A are combined with each other to form a substituted or unsubstituted monocyclic ring, or are joined together to form a substituted or unsubstituted fused ring or are not joined together.
  • R 322A and R 323A which is not a single bond bound to L 31A is combined with each other to form a substituted or unsubstituted monocyclic ring, or are joined together to form a substituted or unsubstituted fused ring or are not joined together.
  • R 311A to R 318A , R 321A which are not a single bond bonded to L 31A and do not form a substituted or unsubstituted single ring and do not form a substituted or unsubstituted condensed ring, and a single bond bonded to L 31A and R 322A and R 323A that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently It is a hydrogen atom or a substituent R.
  • Substituent R is as defined in formula (3) above. ]
  • X 34A is N(R 321A ).
  • the compound represented by formula (3) is a compound represented by formula (33) below.
  • X 31A to X 33A , R 31A and R 32A are each as defined in formula (3) above.
  • L 31A is as defined in formula (31) above.
  • R 311A to R 318A are each as defined in formula (32) above.
  • L 31A is a single bond or an unsubstituted arylene group having 6 to 50 ring carbon atoms
  • Substituent R is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 911 ) (R 912 ) (R 913 ), —O—(R 914 ), -S-(R 915 ), -N(R 916 )(R 917 ), a halogen atom, a cyano group, a nitro group, or an unsubstituted aryl group having 6 to 50 ring carbon atoms
  • R 911 to R 917 are each independently hydrogen atom, an unsubstituted alkyl group having 1
  • R 311A -R 318A are hydrogen atoms.
  • two of X 31A -X 33A are nitrogen atoms and the remaining one of X 31A -X 33A is CR 34A .
  • each of the two or more R 941 to R 953 may be the same or different), a hydroxy group, It is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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" in the compound represented by formula (3) is an alkyl group having 1 to 50 carbon atoms, 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" in the compound represented by formula (3) is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 ring carbon atoms. , and a monovalent heterocyclic group having 5 to 30 ring atoms.
  • the substituent in the case of "substituted or unsubstituted" in the compound represented by formula (3) is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms , and a monovalent heterocyclic group having 5 to 18 ring atoms.
  • the compound represented by formula (3) can be synthesized by using known alternative reactions and raw materials suitable for the target product.
  • the substrate is used as a support for the light emitting device.
  • the substrate for example, glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • a flexible substrate is a (flexible) substrate that can be bent, and examples thereof include plastic substrates made of polycarbonate and polyvinyl chloride.
  • anode 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) for the anode formed on the substrate.
  • ITO Indium Tin Oxide
  • indium oxide-tin oxide containing silicon or silicon oxide indium oxide-zinc oxide
  • tungsten oxide indium oxide containing zinc oxide
  • graphene graphene
  • Other examples include gold (Au), platinum (Pt), and nitrides of metal materials (eg, titanium nitride).
  • a hole injection layer is a layer containing a substance having a high hole injection property.
  • 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 oxides, manganese oxides, aromatic amine compounds, polymer compounds (oligomers, dendrimers, polymers, etc.) and the like can also be used.
  • a hole-transport layer is a layer containing a substance having a high hole-transport property.
  • Aromatic amine compounds, carbazole derivatives, anthracene derivatives and the like can be used in the hole transport layer.
  • 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)
  • other substances may be used as long as they have a higher hole-transport property than electron-transport property.
  • the layer containing a substance having a high hole-transport property is not limited to a single layer, and may be a laminate of two or more layers containing the above substances.
  • the light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as the 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.
  • a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, or the like can be used as a blue fluorescent light-emitting material that can be used in the light-emitting layer.
  • An aromatic amine derivative or the like can be used as a greenish fluorescent light-emitting material that can be used in the light-emitting layer.
  • a tetracene derivative, a diamine derivative, or the like can be used as a red fluorescent light-emitting material that can be used in the light-emitting layer.
  • 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.
  • An iridium complex or the like is used as a greenish phosphorescent light-emitting 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 reddish phosphorescent materials that can be used in the light-emitting layer.
  • the light-emitting layer may have a structure in which the above-described highly light-emitting substance (guest material) is dispersed in another substance (host material).
  • guest material the substance for dispersing the highly luminescent substance
  • various substances can be used. It is preferable to use a substance whose lowest unoccupied molecular orbital level (LUMO level) is higher than that of the substance and whose highest occupied molecular orbital level (HOMO level) is lower.
  • LUMO level lowest unoccupied molecular orbital level
  • HOMO level highest occupied molecular orbital level
  • Substances (host materials) for dispersing highly luminescent substances include 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, and 2) oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives, and the like. 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives or chrysene derivatives; 4) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives; used.
  • a delayed fluorescent (thermally activated delayed fluorescent) compound can also be used as the host material. It is also preferable that the light-emitting layer contains the material used in the present invention described above and a delayed fluorescent host compound.
  • the electron transport layer is a layer containing a substance having a high electron transport property.
  • the electron transport layer in addition to the materials used in the present invention (the compound represented by the formula (3)) described above, 1) metal complexes such as aluminum complexes, beryllium complexes and zinc complexes, 2) imidazole derivatives, benzo Heteroaromatic compounds such as imidazole derivatives, azine derivatives, carbazole derivatives and phenanthroline derivatives, and 3) polymer compounds can be used.
  • the electron injection layer is a layer containing a substance with high electron injection properties.
  • a substance with high electron injection properties 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.
  • cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having 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, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium ( Ca), alkaline earth metals such as strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), europium (Eu), rare earth metals such as ytterbium (Yb), and alloys containing these.
  • a cathode is usually formed by a vacuum deposition method or a sputtering method.
  • a coating method, an inkjet method, or the like can be used.
  • various conductive materials such as aluminum, silver, ITO, graphene, silicon or indium oxide-tin oxide containing silicon oxide are used to form the cathode. can be formed.
  • An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, or the like may be provided adjacent to the light-emitting layer.
  • the electron-blocking layer is a layer having a function of blocking electrons from leaking from the light-emitting layer to the hole-transporting layer.
  • a hole-blocking layer is a layer having a function of blocking leakage of holes from a light-emitting layer to an electron-transporting layer.
  • the exciton-blocking layer is a layer that has the function of blocking excitons generated in the light-emitting layer from diffusing to adjacent layers and confining the excitons within the light-emitting layer.
  • the film thickness of each layer is not particularly limited, but in general, it is from several nm to suppress defects such as pinholes, to keep the applied voltage low, and to improve the luminous efficiency. A range of 1 ⁇ m is preferred.
  • each layer is not particularly limited. Formation methods such as a conventionally known vacuum vapor deposition method and spin coating method can be used. Each layer such as the light-emitting layer is formed by a vacuum deposition method, a molecular beam deposition method (MBE method), or a known coating method such as a dipping method of a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like. can be formed in a manner
  • An electronic device includes the organic EL element according to one aspect 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, and personal computers, and light-emitting devices such as lighting fixtures and vehicle lamps.
  • Comparative compounds used in the production of the organic EL devices of Comparative Examples 1 to 3 are shown below.
  • Comparative compounds used in the evaluation of the stability of the deuteration rate in Comparative Example 4 are shown below.
  • Example 1 ⁇ Production of organic EL element> A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of ITO was set to 130 nm. After washing, the glass substrate with the transparent electrode is mounted on a substrate holder of a vacuum vapor deposition apparatus, and compound HI-1 is vapor-deposited on the surface on which the transparent electrode is formed so as to cover the transparent electrode, resulting in a film thickness of 5 nm. to form a compound HI-1 film. This HI-1 film functions as a hole injection layer.
  • ITO transparent electrode anode
  • UV ozone cleaning for 30 minutes.
  • the film thickness of ITO was set to 130 nm.
  • the glass substrate with the transparent electrode is mounted on a substrate holder of a vacuum vapor deposition apparatus, and
  • the compound HT-1 was vapor-deposited to form an HT-1 film having a thickness of 80 nm on the HI-1 film.
  • This HT-1 film functions as the first hole transport layer.
  • the compound EBL-1 was vapor-deposited to form an EBL-1 film having a thickness of 10 nm on the HT-1 film.
  • This EBL-1 film functions as a second hole transport layer.
  • BH-1A (host material) and BD-1 (dopant material) are co-deposited on the EBL-1 film so that the ratio (weight ratio) of the compound BD-1 is 2%, and a light emitting layer having a thickness of 25 nm is formed. A film was formed.
  • a compound HBL-1 was vapor-deposited on this light-emitting layer to form an electron-transporting layer with a thickness of 10 nm.
  • Compound ET-1 which is an electron injection material, was deposited on the electron transport layer to form an electron injection layer having a thickness of 15 nm.
  • LiF was vapor-deposited on this electron injection layer to form a LiF film with a thickness of 1 nm.
  • Metal Al was vapor-deposited on this LiF film to form a metal cathode with a film thickness of 80 nm.
  • the element configuration of the organic EL element of Example 1 is schematically shown as follows. ITO(130)/HI-1(5)/HT-1(80)/EBL-1(10)/BH-1A:BD-1(25:2%)/HBL-1(10)/ET-1 (15)/LiF(1)/Al(80)
  • the numbers in parentheses represent the film thickness (unit: nm).
  • Examples 2-3 An organic EL device was produced and evaluated in the same manner as in Example 1, except that the compound shown in Table 1 was used as the host material for the light-emitting layer. Table 1 shows the results.
  • Example 4 An organic EL device was fabricated and evaluated in the same manner as in Example 1 except that BH-2 was used as the host material for the light emitting layer and HBL-2 was used instead of HBL-1 in forming the electron transport layer. Table 1 shows the results.
  • Comparative example 1 An organic EL device was produced and evaluated in the same manner as in Example 1, except that BH-Ref1 was used as the host material of the light-emitting layer. Table 1 shows the results.
  • Examples 5-6 An organic EL device was produced and evaluated in the same manner as in Example 1, except that the compound shown in Table 2 was used as the host material for the light-emitting layer. Table 2 shows the results. Numerical values in the table are relative values when Comparative Example 3, which will be described later, is taken as 100%.
  • Comparative Examples 2-3 An organic EL device was produced and evaluated in the same manner as in Example 1, except that the compound shown in Table 2 was used as the host material for the light-emitting layer. Table 2 shows the results. Numerical values in the table are relative values when Comparative Example 3 is taken as 100%.
  • Example 7 BH-6 was synthesized four times by the method described in Synthesis Examples below, and the deuteration rate was measured by NMR analysis under the following conditions. Based on the measurement results of the deuteration rate, the standard deviation of the deuteration rate of the compound BH-6 obtained by the four syntheses was evaluated. Table 3 shows the results.
  • Comparative example 4 BH-Ref4 was synthesized four times by the method described in Synthesis Examples below. Evaluation was performed in the same manner as in Example 7 except that BH-Ref4 was used instead of BH-6. Table 3 shows the results.
  • BH-6 synthesized four times in Example 7 had little variation in the deuteration rate and was excellent in the stability of the deuteration rate during production.
  • BH-Ref4 synthesized four times in Comparative Example 4 had a large variation in deuteration rate, and the deuteration rate was not stable during production.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composé représenté par la formule (101) (dans laquelle au moins l'un des R101 à R104 est combiné à L2 pour former une liaison simple, et les R105 à R108 et au moins deux des R101 à R104 qui n'ont pas été combinés à L2 représentent chacun indépendamment un groupe aryle substitué, ou non, comportant un atome d'hydrogène lourd et comportant de 6 à 50 atomes de carbone nucléaire ou un groupe hétérocyclique monovalent substitué, ou non, comportant un atome d'hydrogène lourd et comportant de 5 à 50 atomes nucléaires).
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