WO2020075783A1 - Nouveau composé, élément électroluminescent organique et dispositif électronique - Google Patents

Nouveau composé, élément électroluminescent organique et dispositif électronique Download PDF

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Publication number
WO2020075783A1
WO2020075783A1 PCT/JP2019/039915 JP2019039915W WO2020075783A1 WO 2020075783 A1 WO2020075783 A1 WO 2020075783A1 JP 2019039915 W JP2019039915 W JP 2019039915W WO 2020075783 A1 WO2020075783 A1 WO 2020075783A1
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substituted
ring
group
unsubstituted
carbon atoms
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PCT/JP2019/039915
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English (en)
Japanese (ja)
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裕基 中野
太郎 八巻
聡美 田崎
加藤　朋希
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出光興産株式会社
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Priority claimed from US16/557,725 external-priority patent/US10777752B2/en
Application filed by 出光興産株式会社 filed Critical 出光興産株式会社
Priority to CN201980066845.1A priority Critical patent/CN112789269A/zh
Priority to KR1020217010389A priority patent/KR20210075089A/ko
Priority to US17/283,382 priority patent/US20230020436A1/en
Publication of WO2020075783A1 publication Critical patent/WO2020075783A1/fr

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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
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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 a novel compound, an organic electroluminescence device and an electronic device.
  • organic electroluminescence element (hereinafter, also referred to as “organic EL element”)
  • organic EL element When a voltage is applied to the organic electroluminescence element (hereinafter, also referred to as “organic EL element”), holes are injected from the anode and electrons are injected from the cathode into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons.
  • the materials used for the organic EL element are gradually being improved (for example, Patent Documents 1 to 7), but higher performance is required.
  • the improvement of the life of the organic EL element is an important issue that leads to the life of a commercialized product, and therefore a material capable of realizing a long-life organic EL element is required.
  • An object of the present invention is to provide a compound capable of producing a long-life organic EL element, a long-life organic EL element, and an electronic device using the organic EL element.
  • the present inventors have conducted extensive studies to achieve the above object, and as a result, have found that an organic EL device having an excellent life can be obtained by using a compound having a specific structure represented by the formula (1). Completed the invention. According to the present invention, the following compounds, organic EL devices and electronic devices are provided. 1. A compound represented by the following formula (1).
  • R 1 to R 8 are each independently: Hydrogen atom, 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-forming 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 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.
  • 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • At least one of R 1 to R 8 is a deuterium atom.
  • L 1 and L 2 are each independently: Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s).
  • Ar 1 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.
  • Ar 2 is a monovalent group represented by the following formula (2), (3) or (4).
  • R 15 to R 20 Two or more adjacent pairs of R 15 to R 20 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is formed. Do not form.
  • one of R 13 to R 20 is L 2 Is a single bond that binds to.
  • the substituted or unsubstituted saturated or unsaturated ring is R 15 to R 20 that are not formed, and one of R 13 and R 14 is a single bond that is bonded to L 2 .
  • R 13 to R 20 which do not form a substituted or unsubstituted saturated or unsaturated ring and which are not a single bond bonded to L 2
  • R 11 and R 12 are each independently, Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atom
  • R 901 to R 907 are as defined in the above formula (1).
  • An organic material having a cathode, an anode, and one or more organic layers arranged between the cathode and the anode, at least one of the organic layers containing the compound described in 1.
  • Electroluminescent device An electronic device comprising the organic electroluminescence element according to 3.2.
  • the present invention it is possible to provide a compound capable of manufacturing a long-life organic EL element, a long-life organic EL element, and an electronic device using the organic EL element.
  • hydroxide includes isotopes having different neutron numbers, that is, protium, deuterium, and tritium.
  • the number of ring-forming carbon atoms refers to the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). Indicates the number of carbon atoms among the atoms. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon number.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 ring-forming carbons
  • a naphthalene ring has 10 ring-forming carbons
  • a pyridine ring has 5 ring-forming carbons
  • a furan ring has 4 ring-forming carbons.
  • 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 carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms.
  • the number of ring-forming atoms means a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a condensed ring, a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, Ring compound) represents the number of atoms constituting the ring itself.
  • the atoms that do not form a ring eg, hydrogen atoms that terminate the bonds of the atoms that make up the ring
  • the atoms that are included in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms.
  • the “number of ring-forming atoms” described below is the same unless otherwise specified.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms.
  • the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms” represents the number of carbon atoms when the ZZ group is unsubstituted.
  • the carbon number of the substituent in the case where it is performed is not included.
  • “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • atom number XX to YY in the expression “substituted or unsubstituted ZZ group having XX to YY atoms” means the number of atoms when the ZZ group is unsubstituted, The number of atoms of the substituent when it is included is not included.
  • YY is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • the ring-forming carbon number of the “unsubstituted aryl group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. .
  • the number of ring-forming atoms of the “unsubstituted heterocyclic group” described herein is from 5 to 50, preferably from 5 to 30, more preferably from 5 to 18, unless otherwise specified herein. is there.
  • the carbon number of the “unsubstituted alkyl group” described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.
  • the carbon number of the “unsubstituted alkenyl group” described in the present specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in the present specification.
  • the carbon number of the “unsubstituted alkynyl group” described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.
  • the number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification. is there.
  • the number of ring-forming carbon atoms of the “unsubstituted arylene group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. .
  • the number of ring-forming atoms of the “unsubstituted divalent heterocyclic group” described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 unless otherwise specified in the present specification. ⁇ 18.
  • the carbon number of the “unsubstituted alkylene group” described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.
  • Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” described in the present specification include the following unsubstituted aryl groups and substituted aryl groups.
  • the unsubstituted aryl group refers to the case where the “substituted or unsubstituted aryl group” is the “unsubstituted aryl group”, and the substituted aryl group is the “substituted or unsubstituted aryl group”.
  • substituted aryl group is used below.
  • aryl group includes both "unsubstituted aryl group” and "substituted aryl group”.
  • the “substituted aryl group” is a case where the “unsubstituted aryl group” has a substituent, and examples thereof include a group in which the following “unsubstituted aryl group” has a substituent and examples of a substituted aryl group. .
  • the examples of the “unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are merely examples, and the “substituted aryl group” described in the present specification includes “unsubstituted aryl group”.
  • the group in which the “group” has a substituent further has a substituent
  • the “substituted aryl group” further has a substituent.
  • aryl group Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, a 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, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, A chrysenyl group, Benzochrysenyl group, Triphenylenyl group, Tripheny
  • Substituted aryl group o-tolyl group, m-tolyl group, p-tolyl group, Para-xylyl group, Meta-xylyl group, Ortho-xylyl group, Para-isopropylphenyl group, Meta-isopropylphenyl group, Ortho-isopropylphenyl group, Para-t-butylphenyl group, Meta-t-butylphenyl group, Ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-di (4-methylphenyl) fluorenyl group, 9,9-di (4-isopropylphenyl) fluorenyl group, 9,9-di (4-tbutylphenyl) fluorenyl group, A cyanophenyl group, Triphenylsilylphenyl group, Trimethyls
  • heterocyclic group is a cyclic group containing at least one hetero atom as a ring forming atom.
  • the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
  • the “heterocyclic group” described in the present specification may be a monocyclic group or a condensed ring group.
  • the “heterocyclic group” described in the present specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.
  • substituted or unsubstituted heterocyclic group examples include the following unsubstituted heterocyclic groups and substituted heterocyclic groups.
  • an unsubstituted heterocyclic group refers to a case where “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group”, and a substituted heterocyclic group refers to “substituted or unsubstituted heterocyclic group.”
  • heterocyclic group is a “substituted heterocyclic group”.
  • both “unsubstituted heterocyclic group” and “substituted heterocyclic group” are used.
  • the “substituted heterocyclic group” is a case where the “unsubstituted heterocyclic group” has a substituent, and the following “unsubstituted heterocyclic group” has a substituent or an example of a substituted heterocyclic group. And the like.
  • the examples of the “unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” are merely examples, and the “substituted heterocyclic group” described in the present specification includes “unsubstituted heterocyclic group”.
  • a group in which the “substituted heterocyclic group” has a substituent further has a substituent
  • a group in which the “substituted heterocyclic group” further has a substituent is also included.
  • Unsubstituted heterocyclic group containing oxygen atom Frill group, An oxazolyl group, Isoxazolyl group, An oxadiazolyl group, Xanthenyl group, Benzofuranyl group, An isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxazinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaphthobenzofuranyl group, Diazanaphthobenzofuranyl group, Diazanaphthobenzofuranyl group
  • Unsubstituted heterocyclic group containing a sulfur atom Thienyl group, Thiazolyl group, An isothiazolyl group, Thiadiazolyl group, Benzothiophenyl group, Isobenzothiophenyl group, Dibenzothiophenyl group, Naphthobenzothiophenyl group, Benzothiazolyl group, Benzoisothiazolyl group, Phenothiazinyl group, A dinaphthothiophenyl group, Azadibenzothiophenyl group, Diazadibenzothiophenyl group, Azanaphthobenzothiophenyl group, Diazanaphthobenzothiophenyl group
  • a substituted heterocyclic group containing a nitrogen atom (9-phenyl) carbazolyl group, (9-biphenylyl) carbazolyl group, (9-phenyl) phenylcarbazolyl group, (9-naphthyl) carbazolyl group, A diphenylcarbazol-9-yl group, A phenylcarbazol-9-yl group, A methylbenzimidazolyl group, Ethyl benzimidazolyl group, Phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group, Biphenylylquinazolinyl group
  • a substituted heterocyclic group containing an oxygen atom Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-butyldibenzofuranyl group, Monovalent residue of spiro [9H-xanthene-9,9 '-[9H] fluorene]
  • 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 heterocyclic ring represented by the above formulas (XY-1) to (XY-18) has a bond at an arbitrary position to be a monovalent heterocyclic group.
  • the monovalent group derived from the unsubstituted heterocyclic ring represented by the above formulas (XY-1) to (XY-18) has a substituent when the carbon atom constituting the skeleton in these formulas is when bonded hydrogen atoms is replaced by a substituent, or, X a and Y a is NH or CH 2, hydrogen atoms in these NH or CH 2 may refer to a state in which is replaced by a substituent.
  • specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” described in the present specification include the following unsubstituted alkyl groups and substituted alkyl groups.
  • the unsubstituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”
  • the substituted alkyl group refers to a “substituted or unsubstituted alkyl group”
  • the term “substituted alkyl group” is referred to.
  • the term “alkyl group” includes both “unsubstituted alkyl group” and “substituted alkyl group”.
  • the “substituted alkyl group” is a case where the “unsubstituted alkyl group” has a substituent, and examples thereof include a group in which the following “unsubstituted alkyl group” has a substituent and examples of a substituted alkyl group. .
  • the examples of the “unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the “substituted alkyl group” described in this specification includes “unsubstituted alkyl group”.
  • the group in which the “group” has a substituent further has a substituent
  • the “substituted alkyl group” further has a substituent.
  • Unsubstituted alkyl group Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, Isobutyl group, s-butyl group, t-butyl group
  • Substituted alkyl group Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, Trifluoromethyl group
  • specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” described in the present specification include the following unsubstituted alkenyl groups and substituted alkenyl groups.
  • the unsubstituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is an “unsubstituted alkenyl group”
  • the “substituted alkenyl group” refers to a “substituted or unsubstituted alkenyl group.” Is a "substituted alkenyl group”.
  • alkenyl group includes both "unsubstituted alkenyl group” and "substituted alkenyl group”.
  • the ⁇ substituted alkenyl group '' is a case where the ⁇ unsubstituted alkenyl group '' has a substituent, and examples of the following ⁇ unsubstituted alkenyl group '' include a group having a substituent and a substituted alkenyl group. .
  • the examples of the “unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” are merely examples, and the “substituted alkenyl group” described in the present specification includes “unsubstituted alkenyl group”.
  • the group in which the “group” has a substituent further has a substituent
  • the “substituted alkenyl group” further has a substituent.
  • Unsubstituted alkenyl group and substituted alkenyl group Vinyl group, Allyl group, 1-butenyl group, 2-butenyl group, A 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1,2-dimethylallyl group
  • Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” described in the present specification include the following unsubstituted alkynyl groups.
  • the unsubstituted alkynyl group refers to a case where the “substituted or unsubstituted alkynyl group” is an “unsubstituted alkynyl group”.
  • alkynyl group Alkynyl group "and” substituted alkynyl group ".
  • substituted alkynyl group is a case where the “unsubstituted alkynyl group” has a substituent, and examples thereof include the following “unsubstituted alkynyl group” having a substituent.
  • Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” described in the present specification include the following unsubstituted cycloalkyl groups and substituted cycloalkyl groups.
  • the unsubstituted cycloalkyl group refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group”, and the substituted cycloalkyl group is the “substituted or unsubstituted
  • cycloalkyl group means a "substituted cycloalkyl group”.
  • Substituted cycloalkyl group is a case where "unsubstituted cycloalkyl group” has a substituent, and examples of the following "unsubstituted cycloalkyl group” have a substituent and substituted cycloalkyl groups. And the like. It should be noted that the examples of the “unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” are merely examples, and the “substituted cycloalkyl group” described in this specification includes “unsubstituted cycloalkyl group”. A group in which the “substituted cycloalkyl group” further has a substituent, a group in which the “substituted cycloalkyl group” further has a substituent, and the like are also included.
  • Specific examples of the group represented by —Si (R 901 ) (R 902 ) (R 903 ) described in the present specification include: -Si (G1) (G1) (G1), -Si (G1) (G2) (G2), -Si (G1) (G1) (G2), -Si (G2) (G2) (G2), -Si (G3) (G3) (G3), -Si (G5) (G5) (G5), -Si (G6) (G6) (G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is the “heterocyclic group” described in Specific Example Group G2.
  • G3 is the “alkyl group” described in Specific Example Group G3.
  • G5 is the “alkynyl group” described in Specific Example Group G5.
  • G6 is the “cycloalkyl group” described in Specific Example Group G6.
  • G8 Specific examples of the group represented by —O— (R 904 ) described in the present specification (specific example group G8) include -O (G1), -O (G2), -O (G3), -O (G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is the “heterocyclic group” described in Specific Example Group G2.
  • G3 is the “alkyl group” described in Specific Example Group G3.
  • G6 is the “cycloalkyl group” described in Specific Example Group G6.
  • G9 Specific examples of the group represented by -S- (R 905 ) described in the present specification (specific example group G9) include -S (G1), -S (G2), -S (G3), -S (G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is the “heterocyclic group” described in Specific Example Group G2.
  • G3 is the “alkyl group” described in Specific Example Group G3.
  • G6 is the “cycloalkyl group” described in Specific Example Group G6.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is the “heterocyclic group” described in Specific Example Group G2.
  • G3 is the “alkyl group” described in Specific Example Group G3.
  • G6 is the “cycloalkyl group” described in Specific Example Group G6.
  • Specific examples (specific example group G11) of the “halogen atom” described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • a specific example of the “alkoxy group” described in the present specification is a group represented by —O (G3), where G3 is an “alkyl group” described in the specific example group G3.
  • the carbon number of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
  • a specific example of the “alkylthio group” described in the present specification is a group represented by —S (G3), where G3 is the “alkyl group” described in the specific example group G3.
  • the carbon number of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
  • a specific example of the “aryloxy group” described in the present specification is a group represented by —O (G1), where G1 is the “aryl group” described in the specific example group G1.
  • the ring-forming carbon number of the “unsubstituted aryloxy group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • a specific example of the “arylthio group” described in the present specification is a group represented by —S (G1), where G1 is the “aryl group” described in the specific example group G1.
  • the ring-forming carbon number of the “unsubstituted arylthio group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • a specific example of the “aralkyl group” described in the present specification is a group represented by — (G3) — (G1), wherein G3 is an “alkyl group” described in the specific example group G3. , G1 is the “aryl group” described in Specific Example Group G1.
  • an “aralkyl group” is an embodiment of a “substituted alkyl group” substituted with an “aryl group”.
  • the carbon number of the “unsubstituted aralkyl group” which is the “unsubstituted alkyl group” substituted by the “unsubstituted aryl group” is 7 to 50, preferably 7 unless otherwise specified in the present specification. -30, more preferably 7-18.
  • aralkyl group examples include, for example, 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, 2- ⁇ -naphthylisopropyl group and the like.
  • the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a 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 , A pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluor
  • the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, unless otherwise specified in the present specification.
  • Nanthrolinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 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) carbazolyl -1-yl group, (9-phenyl) carbazol-2-yl group, (9-phenyl) carbazol-3-yl group, or (9-phenyl) carbazol-4-yl group), (9-biphen
  • dibenzofuranyl group and dibenzothiophenyl group are specifically any one of the following groups unless otherwise described in this specification.
  • X B is an oxygen atom or a sulfur atom.
  • the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group. And the like.
  • the “substituted or unsubstituted arylene group” described in the present specification means a divalent group of the above “aryl group”.
  • Specific examples of the “substituted or unsubstituted arylene group” include a divalent group of the “aryl group” described in specific example group G1. That is, as a specific example (specific group G12) of the "substituted or unsubstituted arylene group", a group excluding one hydrogen bonded to the ring-forming carbon of the "aryl group” described in the specific group G1. Is.
  • Specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” described in the present specification include groups obtained by divalently converting the “heterocyclic group” described in the specific example group G2. Is mentioned. That is, specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” include one of the “heterocyclic groups” bonded to the ring-forming atom of the “heterocyclic group” described in the specific example group G2. It is a group excluding hydrogen.
  • the substituted or unsubstituted arylene group described in the present specification is preferably any one of the following groups unless otherwise described in the present specification.
  • R 908 is a substituent.
  • m901 is 0 to a 4 integer, when m901 represents 2 or more, to R 908 of existing in plural numbers may be the same as each other or may be different.
  • R 909 is each independently a hydrogen atom or a substituent. Two R 909 may be bonded to each other via a single bond to form a ring.
  • R 910 is a substituent.
  • m902 is an integer of 0 to 6.
  • a plurality of R 910 may be the same as or different from each other.
  • the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following groups unless otherwise described in the present specification.
  • R 911 is a hydrogen atom or a substituent.
  • X B is an oxygen atom or a sulfur atom.
  • adjacent two which form a ring when one or more adjacent two or more are bonded to each other to form a ring includes R 921 and R 922 , R 922 and R 923, R 923 and R 924, R 924 and R 930, 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 .
  • the “one or more sets” means that two or more adjacent two sets may form a ring at the same time.
  • R 921 and R 922 combine with each other to form ring A
  • R 925 and R 926 combine with each other to form ring B
  • the compound is represented by the following formula (XY-81) .
  • R 921 and R 922 combine with each other to form ring A
  • R 922 and R 923 combine with each other to form ring C
  • XY-82 In the case where three adjacent R 921 to R 923 are fused to the anthracene mother skeleton to form a ring A and a ring C sharing R 922 , they are represented by the following formula (XY-82).
  • the rings A to C formed in the above formulas (XY-81) and (XY-82) are saturated or unsaturated rings.
  • “Unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • “Saturated ring” means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.
  • a ring A formed by bonding R 921 and R 922 to each other has a carbon atom of an anthracene skeleton to which R 921 is bonded and a carbon atom of an anthracene skeleton to which R 922 is bonded.
  • a ring formed by atoms and one or more optional elements is meant.
  • the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms are different.
  • the ring formed by R 921 and R 922 is a benzene ring.
  • the ring is a cyclohexane ring.
  • the “arbitrary element” is preferably a C element, an N element, an O element, or an S element.
  • a bond that does not participate in ring formation may be terminated with a hydrogen atom or the like, or may be substituted with an arbitrary substituent.
  • the formed ring is a heterocyclic ring.
  • “One or more optional elements” constituting a saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less. .
  • the aromatic hydrocarbon ring a structure in which the aryl group mentioned as a specific example in the specific example group G1 is terminated with a hydrogen atom is given.
  • the aromatic heterocyclic ring a structure in which the aromatic heterocyclic group described as a specific example in the specific example group G2 is terminated with a hydrogen atom is given.
  • Specific examples of the aliphatic hydrocarbon ring include a structure in which the cycloalkyl group mentioned as a specific example in Specific Example Group G6 is terminated with a hydrogen atom.
  • the substituent is, for example, an “optional substituent” described later.
  • Specific examples of the substituent in the case where the above “saturated or unsaturated ring” has a substituent are the substituents described in the above section of “the substituent described in the present specification”.
  • the substituent in the case of “substituted or unsubstituted” may be: 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 carbon atoms for ring formation, —Si (R 901 ) (R 902 ) (R 903 ), —O— (R 904 ), -S- (R 905 ), -N ( R906 ) ( R907 ) (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
  • 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 a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the substituents when referred to 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 monovalent heterocyclic group having 5 to 50 ring atoms.
  • the substituents when referred to 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 monovalent heterocyclic group having 5 to 18 ring atoms.
  • adjacent substituents may be substituted with a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5- or 6-membered ring, (Preferably, a benzene ring).
  • an optional substituent may further have a substituent unless otherwise specified. Examples of the substituent further included in the optional substituent include those similar to the optional substituent described above.
  • R 1 to R 8 are each independently: Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocycl
  • 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • At least one of R 1 to R 8 is a deuterium atom.
  • L 1 and L 2 are each independently: Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s).
  • Ar 1 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.
  • Ar 2 is a monovalent group represented by the following formula (2), (3) or (4).
  • R 15 to R 20 Two or more adjacent pairs of R 15 to R 20 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is formed. Do not form.
  • one of R 13 to R 20 is L 2 Is a single bond that binds to.
  • the substituted or unsubstituted saturated or unsaturated ring is R 15 to R 20 that are not formed, and one of R 13 and R 14 is a single bond that is bonded to L 2 .
  • R 13 to R 20 which do not form a substituted or unsubstituted saturated or unsaturated ring and which are not a single bond bonded to L 2
  • R 11 and R 12 are each independently, Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atom
  • the compound according to one embodiment of the present invention can improve device performance when used in an organic EL device. Specifically, it becomes possible to provide an organic EL element having a longer life. Further, according to one aspect of the present invention, there can be provided a method for improving the performance of an organic EL device, which comprises using the above compound in a light emitting layer of the organic EL device. Specifically, the method specifically includes a compound having the same structure as the compound represented by the formula (1) except that the host material contains only a light hydrogen atom as a hydrogen atom (hereinafter, also referred to as a “light hydrogen form”). This makes it possible to improve the performance of the organic EL element, as compared with the case of using.
  • a light hydrogen means that substantially only a light hydrogen is used as the host material in the light emitting layer (the content of the light hydrogen is based on the sum of the compound represented by the formula (1) and the light hydrogen).
  • the ratio is 90 mol% or more, 95 mol% or more, or 99 mol% or more). That is, as a host material, at least one of the light hydrogen atoms on the anthracene skeleton was replaced with a deuterium atom among the light hydrogen atoms of the light hydrogen form instead of or in addition to the light hydrogen form.
  • R 1 to R 8 may be deuterium atoms, or some (eg, 1 or 2 or more) may be deuterium atoms.
  • R 1 to R 8 which are not deuterium atoms are preferably hydrogen atoms (light hydrogen atoms).
  • At least one of the hydrogen atoms possessed by one or more selected from the group consisting of L 1 and L 2 is a deuterium atom.
  • one or more selected from the group consisting of L 1 and L 2 is an unsubstituted arylene group having 6 to 30 ring-forming carbon atoms in which at least one of hydrogen atoms is a deuterium atom.
  • an unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms in which at least one of hydrogen atoms is a deuterium atom.
  • L 1 and L 2 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms.
  • at least one of L 1 and L 2 is a single bond.
  • R 13 or R 14 in formulas (2) to (4) is a single bond that is bonded to L 2 .
  • two or more adjacent pairs of R 15 to R 20 in formulas (2) to (4) do not bond with each other to form a substituted or unsubstituted saturated or unsaturated ring.
  • a hydrogen atom is not a single bond that bonds to L 2 and does not contribute to ring formation.
  • At least one of R 11 to R 20 in formulas (2) to (4) that is not a single bond that bonds to L 2 and does not contribute to ring formation is a deuterium atom.
  • At least one hydrogen atom contained in one or more of Ar 1 is a deuterium atom.
  • Ar 1 is an unsubstituted aryl group having 6 to 50 ring carbon atoms in which at least one of hydrogen atoms is a deuterium atom, or at least one of hydrogen atoms is a deuterium atom. It is an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 1 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and more preferably selected from groups represented by the following formulas (a1) to (a4).
  • * represents a single bond bonded to L 1 .
  • R 21's are each independently 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-forming 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 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.
  • R 901 to R 907 are as defined in the above formula (1).
  • m1 is independently an integer of 0 to 4.
  • m2 is independently an integer of 0 to 5.
  • m3 is independently an integer of 0 to 7.
  • a plurality of R 21's may be the same as or different from each other.
  • m1 to m3 are each 2 or more, a plurality of adjacent R 21 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form. )
  • the presence of a deuterium atom in the compound is confirmed by mass spectrometry or 1 H-NMR analysis. Further, the bonding position of the deuterium atom in the compound is specified by 1 H-NMR analysis. Specifically, it is as follows. The target compound is subjected to mass spectrometry, and it can be confirmed that the target compound contains one deuterium atom by increasing the molecular weight by 1 as compared with the corresponding compound in which all hydrogen atoms are light hydrogen atoms. In addition, since no signal is generated for deuterium atoms by 1 H-NMR analysis, the number of deuterium atoms contained in the molecule is determined by an integrated value obtained by performing 1 H-NMR analysis on the target compound. You can check. In addition, 1 H-NMR analysis is performed on the target compound, and the binding position of a deuterium atom can be specified by assigning a signal.
  • a composition according to one embodiment of the present invention contains a compound represented by the formula (1), and the content ratio of the latter is 99 mol% or less based on the total amount of the compound represented by the formula (1) and a hydrogen hydride. Is. The content ratio of the deuterium is confirmed by mass spectrometry. Further, in the composition according to one embodiment of the present invention, the content ratio of the former to the total of the compound represented by the formula (1) and the light hydrogen compound is 30 mol% or more, 50 mol% or more, 70 mol% or more, 90 It is mol% or more, 95 mol% or more, 99 mol% or more, or 100 mol%.
  • the compound represented by the formula (1) has the formula (1-1), (1-2), (1-3), (1-4), (1-5) or (1- It is a compound represented by 6).
  • R 1 to R 8 and R 11 to R 20 , Ar 1 , L 1 and L 2 are as defined in the above formula (1).
  • the compound represented by the formula (1) is represented by the following formula (1-11), (1-12), (1-13), (1-14), (1-15) or (1- It is a compound represented by 16). (In the formulas (1-11), (1-12), (1-13), (1-14), (1-15) and (1-16), R 1 to R 8 , Ar 1 and L 1 Is as defined in the above formula (1).)
  • the compound represented by the formula (1) is represented by the following formula (1-21), (1-22), (1-23), (1-24), (1-25) or (1- It is a compound represented by 26).
  • Ar 1 and L 1 are the same as those in the formula (1). ) Is as defined in.)
  • the compound represented by the formula (1) can be synthesized by following the synthetic method described in the examples and using known alternative reactions or starting materials according to the intended product.
  • D represents a deuterium atom.
  • the above compound can be used as a material for an organic EL device, preferably as a host material for a light emitting layer.
  • An organic EL device has a cathode, an anode, and one or more organic layers arranged between the cathode and the anode, and the organic layer is represented by the formula (1).
  • the organic layer does not contain the compound represented by formula (1) or the composition of the present invention described above, conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired.
  • the light emitting layer of the organic layer preferably contains the compound represented by the formula (1) or the composition of the present invention.
  • the light emitting layer of the organic EL device contains a compound represented by the formula (1) and a light hydrogen compound, and the content ratio of the latter to the total thereof is 99 mol% or less. Is.
  • the light-emitting layer of the organic EL element according to one embodiment of the present invention includes the compound represented by the formula (1) and a deuterium compound, and the content of the former is 30 mols relative to the total. %, 50 mol% or more, 70 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, or 100 mol%.
  • One aspect of the organic EL device of the present invention preferably has a hole transport layer between the anode and the light emitting layer.
  • One aspect of the organic EL device of the present invention preferably has an electron transport layer between the cathode and the 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 “electron injection layer and electron At least one of the transport layers ".
  • the light-emitting layer preferably contains, in addition to the compound (host material) represented by the formula (1), the following formulas (11), (21), (31), (41), (51), (61), It contains at least one compound (dopant material) selected from the group consisting of (71) and (81).
  • R 101 to R 110 which do not form a substituted or unsubstituted saturated or unsaturated ring and which are not a monovalent group represented by the following formula (12) are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted
  • R 901 to R 907 are as defined in the above formula (1).
  • Ar 101 and Ar 102 are each independently A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 101 to L 103 are independently Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s). )]
  • the compound represented by the formula (11) is represented by the following formula (13).
  • R 111 to R 118 are the same as R 101 to R 110 in the formula (11), which are not the monovalent group represented by the formula (12).
  • Ar 101 and Ar 102 , L 101 , L 102, and L 103 are as defined in the above formula (12).
  • L 101 is preferably a single bond
  • L 102 and L 103 are preferably single bonds.
  • the compound represented by the formula (11) is represented by the following formula (14) or (15).
  • R 111 to R 118 are as defined in the formula (13).
  • Ar 101 , Ar 102 , L 102 and L 103 are as defined in the formula (12). .
  • R 111 to R 118 are as defined in the formula (13).
  • Ar 101 and Ar 102 are as defined in the formula (12).
  • At least one of Ar 101 and Ar 102 is a group represented by the following formula (16).
  • X 101 represents an oxygen atom or a sulfur atom.
  • R 121 to R 127 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 121 to R 127 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having
  • X 101 is preferably an oxygen atom.
  • At least one of R 121 to R 127 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-forming carbon atoms, It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 101 is preferably a group represented by the formula (16), and Ar 102 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. .
  • the compound represented by the formula (11) is represented by the following formula (17).
  • R 111 to R 118 are as defined in the formula (13).
  • R 121 to R 127 are as defined in the formula (16).
  • R 131 to R 135 are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted
  • Specific examples of the compound represented by the formula (11) include the following compounds.
  • Me represents a methyl group.
  • Z is each independently CR a or N.
  • the A1 ring and the A2 ring are each independently 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.
  • plural R a are present, one or more adjacent two or more sets of plural R a are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or Does not form an unsubstituted saturated or unsaturated ring.
  • n21 and n22 are each independently an integer of 0 to 4.
  • R a to R c which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having
  • the “aromatic hydrocarbon ring” of the A1 ring and the A2 ring has the same structure as the above-described compound in which a hydrogen atom has been introduced into the “aryl group”.
  • the “aromatic hydrocarbon ring” of the A1 ring and the A2 ring includes two carbon atoms on the central fused bicyclic structure of the formula (21) as ring-forming atoms.
  • Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “aryl group” described in Specific Example Group G1.
  • the “heterocycle” of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom has been introduced into the above “heterocyclic group”.
  • the “heterocycle” of the A1 ring and the A2 ring includes two carbon atoms on the central fused bicyclic structure of the formula (21) as ring-forming atoms.
  • Specific examples of the “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the “heterocyclic group” described in Specific Example Group G2.
  • R b is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring of A1 ring or to the atoms forming the heterocyclic ring of A1 ring.
  • R c is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring of the A2 ring or any of the atoms forming the heterocyclic ring of the A2 ring.
  • At least one (preferably two) of R a to R c is preferably a group represented by the following formula (21a).
  • L 201 is Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s).
  • Ar 201 is A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (21b).
  • L 211 and L 212 are each independently Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s).
  • Ar 211 and Ar 212 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring or no substituted or unsubstituted saturated or unsaturated ring.
  • Ar 211 and Ar 212 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. ))
  • the compound represented by the formula (21) is represented by the following formula (22).
  • formula (22) One or more pairs of adjacent two or more of R 201 to R 211 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring; Does not form a ring.
  • R 201 to R 211 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having
  • At least one (preferably two) of R 201 to R 211 is preferably a group represented by the above formula (21a).
  • R 204 and R 211 are groups represented by the above formula (21a).
  • the compound represented by the formula (21) is a compound in which the structure represented by the following formula (21-1) or (21-2) is bonded to the A1 ring.
  • the compound represented by the formula (22) is a compound in which the structure represented by the following formula (21-1) or (21-2) is bound to the ring to which R 204 to R 207 are bound.
  • the two bonds * are each independently bonded to a ring-forming carbon atom of an aromatic hydrocarbon ring or a ring-forming atom of a heterocyclic ring of the A1 ring of the formula (21); Alternatively, it binds to any of R 204 to R 207 in the formula (22).
  • the three bonds * in formula (21-2) are each independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring of the A1 ring of formula (21) or the ring-forming atom of the heterocycle, or It is bonded to any of R 204 to R 207 in (22). At least one pair of two or more of R 221 to R 227 and R 231 to R 239 is bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or Does not form a substituted saturated or unsaturated ring.
  • R 221 to R 227 and R 231 to R 239 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstitute
  • the compound represented by the formula (21) is a compound represented by the following formula (21-3), (21-4) or (21-5).
  • the ring A1 is as defined in the formula (21).
  • R 2401 to R 2407 are the same as R 221 to R 227 in formulas (21-1) and (21-2).
  • R 2410 to R 2417 are the same as R 201 to R 211 in the formula (22). The two R 2417 may be the same as or different from each other. )
  • the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms of the ring A1 in the formula (21-5) is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted naphthalene ring. It is a fluorene ring.
  • the substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms in ring A1 of formula (21-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or It is a substituted or unsubstituted dibenzothiophene ring.
  • the compound represented by the formula (21) or (22) is selected from the group consisting of compounds represented by the following formulas (21-6-1) to (21-6-7).
  • You. (In formulas (21-6-1) to (21-6-7), R 2421 to R 2427 are the same as R 221 to R 227 in formulas (21-1) and (21-2).
  • R 2430 to R 2437 and R 2441 to R 2444 are the same as R 201 to R 211 in the formula (22).
  • X is O, NR 901 , or C (R 902 ) (R 903 ).
  • R 901 to R 903 are as defined in the above formula (1).
  • At least one set of two or more adjacent R 201 to R 211 is bonded to each other to form a substituted or unsubstituted saturated or unsaturated group. Form a ring.
  • This embodiment will be described in detail below as Expression (25).
  • Two or more rings formed by R 251 to R 261 may be the same or different.
  • R 251 to R 261 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having
  • R n and R n + 1 are bonded to each other to form two rings where R n and R n + 1 are bonded. Together with the forming carbon atom, it forms a substituted or unsubstituted saturated or unsaturated ring.
  • the ring is preferably composed of atoms selected from C, O, S and N atoms, and the number of atoms is preferably 3 to 7, more preferably 5 or 6.
  • the number of the ring structures in the compound represented by the formula (25) is, for example, two, three, or four.
  • the two or more ring structures may each be present on the same benzene ring on the mother skeleton of the formula (25), or may be present on different benzene rings.
  • one ring structure may be present in each of the three benzene rings of formula (25).
  • Examples of the ring structure in the compound represented by the formula (25) include structures represented by the following formulas (251) to (260). (In the formulas (251) to (257), * 1 and * 2, * 3 and * 4, * 5 and * 6, * 7 and * 8, * 9 and * 10, * 11 and * 12, and * 13
  • * 14 represents the two ring-forming carbon atoms to which R n and R n + 1 are bonded, and the ring-forming carbon atoms to which R n is bonded are * 1 and * 2, * 3 and * 4, * 5 and It may be any of the two ring-forming carbon atoms represented by * 6, * 7 and * 8, * 9 and * 10, * 11 and * 12, and * 13 and * 14.
  • X 2501 is C (R 2512 ) (R 2513 ), NR 2514 , O or S.
  • One or more adjacent two or more sets of R 2501 to R 2506 and R 2512 to R 2513 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or unsubstituted. Does not form a substituted saturated or unsaturated ring.
  • R 2501 to R 2514 which do not form a substituted or unsubstituted saturated or unsaturated ring are the same as R 251 to R 261 described above. )
  • * 1 and * 2 and * 3 and * 4 each represent the two ring-forming carbon atoms to which R n and R n + 1 are bonded, and R n is bonded to
  • the ring-forming carbon atom may be any of the two ring-forming carbon atoms represented by * 1 and * 2 or * 3 and * 4.
  • X 2501 is C (R 2512 ) (R 2513 ), NR 2514 , O or S.
  • One or more adjacent two or more sets of R 2515 to R 2525 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated Does not form a ring.
  • R 2515 to R 2521 and R 2522 to R 2525 which do not form a substituted or unsubstituted saturated or unsaturated ring are the same as R 251 to R 261 described above.
  • At least one of R 252 , R 254 , R 255 , R 260 and R 261 is a ring It is preferable that the group does not form a structure.
  • R 251 to R 261 that does not form a ring structure, and (iii) R 2501 to R 2514 and R 2515 to R 2525 in Formulas (251) to (260) are preferably Independently Hydrogen atom, 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-forming carbon atoms, -N (R 906 ) (R 907 ), A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, It is either 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
  • R d is each independently: Hydrogen atom, 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-forming 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 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.
  • X is C (R 901 ) (R 902 ), NR 903 , O or S.
  • R 901 to R 907 are as defined in the above formula (1).
  • p1 is independently an integer of 0 to 5
  • p2 is independently an integer of 0 to 4
  • p3 is an integer of 0 to 3
  • p4 is an integer of 0 to 7.
  • the compound represented by the formula (25) is represented by any of the following formulas (25-1) to (25-6).
  • the rings d to i are each independently a substituted or unsubstituted saturated or unsaturated ring.
  • R 251 to R 261 are the same as those in the formula (25) Same as).
  • the compound represented by formula (25) is represented by any of the following formulas (25-7) to (25-12).
  • rings d to f, k, and j are each independently a substituted or unsubstituted saturated or unsaturated ring.
  • R 251 to R 261 are This is the same as the equation (25).
  • the compound represented by the formula (25) is represented by any of the following formulas (25-13) to (25-21).
  • ring d-k are each independently a ring substituted or unsubstituted, saturated or unsaturated .
  • R 251 - R 261 is the formula (25 Same as).)
  • the substituent is, for example, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Examples thereof include a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the above formula (261), (263) or (264).
  • the compound represented by the formula (25) is represented by any of the following formulas (25-22) to (25-25).
  • X 250 is independently C (R 901 ) (R 902 ), NR 903 , O or S.
  • R 251 to R 261 , R 271 to R 278 is the same as R 251 to R 261 in the above formula (25), and R 901 to R 903 are as defined in the above formula (1).
  • the compound represented by the formula (25) is represented by the following formula (25-26).
  • X 250 is C (R 901 ) (R 902 ), NR 903 , O or S.
  • R 253 , R 254 , R 257 , R 258 , R 261 , and R 271 -R 282 are the same as R 251 -R 261 in the formula (25).
  • R 901 -R 903 are as defined in the formula (1).
  • Specific examples of the compound represented by the formula (21) include the following compounds.
  • Me represents a methyl group.
  • the compound represented by the formula (31) will be described.
  • the compound represented by the formula (31) is a compound corresponding to the compound represented by the formula (21-3) described above.
  • (In equation (31) At least one pair of adjacent two or more of R 301 to R 307 and R 311 to R 317 forms a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring Does not form a ring.
  • R 301 to R 307 and R 311 to R 317 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstitute
  • R 321 and R 322 are each independently Hydrogen atom, 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-forming 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 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.
  • R 901 to R 907 are as defined in
  • One set of two or more adjacent to R 301 to R 307 and R 311 to R 317 is, for example, R 301 and R 302 , R 302 and R 303 , R 303 and R 304 , R 305 and R 306. , R 306 and R 307 , R 301 , R 302 and R 303, and the like.
  • At least one, preferably two of R 301 to R 307 and R 311 to R 317 are groups represented by —N (R 906 ) (R 907 ).
  • R 301 to R 307 and R 311 to R 317 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring group. It is a monovalent heterocyclic group having 5 to 50 atoms.
  • the compound represented by the formula (31) is a compound represented by the following formula (32).
  • (In equation (32) One or more of adjacent two or more of R 331 to R 334 and R 341 to R 344 form a substituted or unsubstituted saturated or unsaturated ring, or are substituted or unsubstituted saturated or unsaturated. Does not form a ring.
  • R 331 to R 334 , R 341 to R 344 and R 351 and R 352 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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.
  • R 361 to R 364 are each independently A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • the compound represented by formula (31) is a compound represented by formula (33) below.
  • R 351 , R 352 and R 361 to R 364 are as defined in the formula (32).
  • the compound represented by the formula (31) is a compound represented by the following formula (34) or (35).
  • R 361 to R 364 are as defined in the above formula (32).
  • At least one pair of adjacent two or more of R 371 to R 377 and R 380 to R 386 forms a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring Does not form a ring.
  • R 371 to R 377 and R 380 to R 386 which do not form a substituted or unsubstituted saturated or unsaturated ring, and R 387 are each independently Hydrogen atom, 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.
  • the two R 387 may be the same as or different from each other. )
  • the compound represented by the formula (31) is a compound represented by the following formula (34-2) or (35-2).
  • R 361 to R 364 , R 375 to R 377 and R 384 to R 387 are as defined in the formulas (34) and (35).
  • R 361 to R 364 in formulas (32), (33), (34), (35), (34-2), and (35-2) are each independently substituted or unsubstituted.
  • 352 is independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).
  • the compound represented by formula (31) is a compound represented by formula (36) below.
  • R 3001 , R 3002 , R 3005 to R 3007 , R 3010 , R 3011 , R 3014 to R 3016 , and R 3031 to R 3034 are They are joined together to form a substituted or unsubstituted saturated or unsaturated ring, or no substituted or unsubstituted saturated or unsaturated ring.
  • X a is independently selected from O, S and N (R 35 ). R 35 is combined with R 3031 to form a substituted or unsubstituted saturated or unsaturated ring, or does not form the ring.
  • R 3001 which do not form a ring substituted or unsubstituted, saturated or unsaturated
  • R 3002, R 3005 ⁇ R 3007, R 3010, R 3011, R 3014 ⁇ R 3016, and R 3031 ⁇ R 3035, and R 3021, R 3022 is each independently: Hydrogen atom, 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.
  • the substituent in the case of “substituted or unsubstituted” in formulas (31) to (36) 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • ring a, ring b and ring c are each independently A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • R 401 and R 402 each independently form a substituted or unsubstituted heterocyclic ring or do not form a substituted or unsubstituted heterocyclic ring by combining with the a ring, the b ring or the c ring.
  • R 401 and R 402 which do not form the substituted or unsubstituted heterocyclic ring are each independently 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • Ring a, ring b and ring c are each a ring (substituted or unsubstituted aromatic ring having 6 to 50 ring-forming carbon atoms) fused to a central fused bicyclic structure of formula (41) composed of a B atom and two N atoms.
  • the “aromatic hydrocarbon ring” of ring a, ring b and ring c has the same structure as the above-described compound in which a hydrogen atom has been introduced into the “aryl group”.
  • the “aromatic hydrocarbon ring” of the ring a contains three carbon atoms on the fused bicyclic structure at the center of the formula (41) as ring-forming atoms.
  • the “aromatic hydrocarbon ring” of the ring b and the ring c includes two carbon atoms on the central fused bicyclic structure of the formula (41) as ring-forming atoms.
  • Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “aryl group” described in Specific Example Group G1.
  • the “heterocycle” of ring a, ring b and ring c has the same structure as the above-mentioned compound in which a hydrogen atom has been introduced into the “heterocyclic group”.
  • the “heterocycle” of ring a contains three carbon atoms on the condensed two-ring structure in the center of formula (41) as ring-forming atoms.
  • the “heterocycle” of the b-ring and the c-ring includes two carbon atoms on the fused bicyclic structure at the center of the formula (41) as ring-forming atoms.
  • Specific examples of the “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the “heterocyclic group” described in Specific Example Group G2.
  • R 401 and R 402 may be independently bonded to ring a, ring b or ring c to form a substituted or unsubstituted heterocyclic ring.
  • the heterocyclic ring in this case will contain a nitrogen atom on the fused bicyclic structure in the center of formula (41). In this case, the heterocyclic ring may contain a hetero atom other than a nitrogen atom.
  • R 401 and R 402 are bonded to ring a, ring b or ring c, specifically, the atom forming ring a, ring b or ring c is bonded to the atom forming ring R 401 or R 402.
  • R 401 may be bonded to ring a to form a two-ring fused (or three-ring fused or more) nitrogen-containing heterocycle in which the ring containing R 401 and the a ring are fused.
  • Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing two-ring fused or more heterocyclic group in Specific Example Group G2. The same applies to the case where R 401 is bonded to ring b, the case where R 402 is bonded to ring a, and the case where R 402 is bonded to ring c.
  • ring a, ring b and ring c in formula (41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms. In one embodiment, ring a, ring b and ring c in formula (41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
  • R 401 and R 402 in Formula (41) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom having 5 to 50 ring atoms. And is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by formula (41) is a compound represented by formula (42) below.
  • R 401A combines with one or more selected from the group consisting of R 411 and R 421 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring.
  • R 402A bonds to one or more selected from the group consisting of R 413 and R 414 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring.
  • R 401A and R 402A which do not form a substituted or unsubstituted heterocyclic ring are each independently 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 411 to R 421 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 411 to R 421 which do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substitute
  • R 401A and R 402A in the formula (42) are groups corresponding to R 401 and R 402 in the formula (41).
  • R 401A and R 411 may combine to form a bicyclic fused (or tricyclic fused or more) nitrogen-containing heterocycle in which a ring containing these and a benzene ring corresponding to ring a are fused.
  • Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing two-ring fused or more heterocyclic group in Specific Example Group G2. The same applies to the case where R 401A and R 412 combine, the case where R 402A and R 413 combine, and the case where R 402A and R 414 combine.
  • R 11 and R 12 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed to a 6-membered ring to which these are bonded,
  • the formed condensed ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.
  • R 411 to R 421 that do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring carbon number having 6 to 50 carbon atoms. Or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 411 to R 421 that do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom number. 5 to 50 monovalent heterocyclic groups.
  • R 411 to R 421 that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 411 to R 421 that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R 411 to R 421 One is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the formula (42) is a compound represented by the following formula (43).
  • R 431 combines with R 446 to form a substituted or unsubstituted heterocyclic ring or does not form a substituted or unsubstituted heterocyclic ring.
  • R 433 combines with R 447 to form a substituted or unsubstituted heterocyclic ring or does not form a substituted or unsubstituted heterocyclic ring.
  • R 441 combines with R 442 to form a substituted or unsubstituted heterocyclic ring or does not form a substituted or unsubstituted heterocyclic ring.
  • One or more of adjacent two or more of R 431 to R 451 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 431 to R 451 which do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted saturated or unsaturated ring are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substitute
  • R 431 may combine with R 446 to form a substituted or unsubstituted heterocycle.
  • R 431 and R 446 combine to form a 3- or more-fused nitrogen-containing heterocycle in which the benzene ring to which R 46 is attached, the ring containing N, and the benzene ring corresponding to ring a are fused.
  • the nitrogen-containing heterocycle include compounds corresponding to a nitrogen-containing three-ring fused or more heterocyclic group in Specific Example Group G2. The same applies to the case where R 433 and R 447 are bonded, the case where R 434 and R 451 are bonded, and the case where R 441 and R 442 are bonded.
  • R 431 to R 451 which do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming carbon number 6 to 50. Or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 431 to R 451 that do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom number. 5 to 50 monovalent heterocyclic groups.
  • R 431 to R 451 that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 431 to R 451 that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R 431 to R 451 is preferred.
  • One is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the formula (43) is a compound represented by the following formula (43A).
  • R 461 is Hydrogen atom, 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, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 462 to R 465 are each independently 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, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 461 to R 465 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 461 to R 465 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the formula (43) is a compound represented by the following formula (43B).
  • R 471 and R 472 are each independently Hydrogen atom, 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-forming carbon atoms, —N (R 906 ) (R 907 ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 473 to R 475 are each independently 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-forming carbon atoms, —N (R 906 ) (R 907 ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 906 and R 907 are as defined in the above formula (1).
  • the compound represented by the formula (43) is a compound represented by the following formula (43B ′).
  • R 472 to R 475 are as defined in the formula (43B).
  • R 471 to R 475 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-forming carbon atoms, —N (R 906 ) (R 907 ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 472 is Hydrogen atom
  • R 471 and R 473 to R 475 are each independently A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, —N (R 906 ) (R 907 ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by the formula (43) is a compound represented by the following formula (43C).
  • R 481 and R 482 are each independently Hydrogen atom, 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, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 483 to R 486 are each independently 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, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by the formula (43) is a compound represented by the following formula (43C ′).
  • R 483 to R 486 are as defined in the formula (43C).
  • R 481 to R 486 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 481 to R 486 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by the formula (41) is prepared as an intermediate by first connecting the a ring, b ring and c ring with a linking group (a group containing NR 1 and a group containing NR 2 ).
  • First reaction the final product can be produced by bonding ring a, ring b and ring c with a linking group (group containing B) (second reaction).
  • first reaction an amination reaction such as a Bhabhurt-Hartwig reaction can be applied.
  • a tandem hetero Friedel-Crafts reaction or the like can be applied.
  • the compound represented by the formula (51) will be described.
  • the r ring is a ring represented by the formula (52) or the formula (53) fused at an arbitrary position of an adjacent ring.
  • the q ring and the s ring are each independently a ring represented by the formula (54) fused at an arbitrary position of an adjacent ring.
  • the p-ring and the t-ring each have a structure represented by the formula (55) or (56), which is independently condensed at an arbitrary position of an adjacent ring.
  • R 501 there are a plurality and do not form a plurality of adjacent R 501 is bonded to either form a ring substituted or unsubstituted, saturated or unsaturated with one another, or a substituted or unsubstituted saturated or unsaturated ring .
  • X 501 is an oxygen atom, a sulfur atom, or NR 502 .
  • R 501 and R 502 which do not form a substituted or unsubstituted saturated or unsaturated ring are Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to
  • R 901 to R 907 are as defined in the above formula (1).
  • Ar 501 and Ar 502 are each independently 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 501 is A substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms, 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.
  • m1 is each independently an integer of 0 to 2
  • m2 is each independently an integer of 0 to 4
  • m3 is each independently an integer of 0 to 3
  • m4 is each independently 0 to 2. It is an integer of 5. If R 501 there are a plurality to plurality of R 501 may be the same as each other or may be different. )
  • each of the rings p to t is fused by sharing two carbon atoms with an adjacent ring.
  • the position and direction of condensation are not limited, and condensation can be performed at any position and direction.
  • R 501 is a hydrogen atom.
  • the compound represented by the formula (51) is represented by any of the following formulas (51-1) to (51-6).
  • R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1 and m3 are as defined in the formula (51).
  • the compound represented by the formula (51) is represented by any of the following formulas (51-11) to (51-13).
  • R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1, m3, and m4 are as defined in Formula (51).
  • the compound represented by the formula (51) is represented by any of the following formulas (51-21) to (51-25).
  • R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1 and m4 are as defined in the formula (51).
  • the compound represented by the formula (51) is represented by any of the following formulas (51-31) to (51-33).
  • R 501 , X 501 , Ar 501 , Ar 502 , L 501 , and m2 to m4 are as defined in the formula (51).
  • Ar 501 and Ar 502 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • one of Ar 501 and Ar 502 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted monovalent monovalent having 5 to 50 ring atom atoms. It is a heterocyclic group.
  • Specific examples of the compound represented by the formula (51) include the following compounds.
  • Me represents a methyl group.
  • R 605 to R 608 those which do not form the divalent group represented by the above formula (63), and at least one of R 621 to R 624 are monovalent groups represented by the following formula (64).
  • X 601 is an oxygen atom, a sulfur atom, or NR 609 .
  • R 601 to R 608 which do not form the divalent group represented by the formulas (62) and (63) and are not the monovalent group represented by the formula (64), the formula (64) R 611 to R 614 and R 621 to R 624 , and R 609 which are not a monovalent group represented by Hydrogen atom, 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-forming 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
  • R 901 to R 907 are as defined in the above formula (1).
  • Ar 601 and Ar 602 are each independently: A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 601 to L 603 are independently Single bond, A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or a divalent linking group formed by combining 2 to 4 of these. )
  • the positions where the divalent group represented by the formula (62) and the divalent group represented by the formula (63) are formed are not particularly limited, and the positions where R 601 to R 608 are possible Such groups can be formed.
  • the compound represented by the formula (61) is represented by any of the following formulas (61-1) to (61-6).
  • X 601 is as defined in the formula (61).
  • At least two of R 601 to R 624 are monovalent groups represented by the above formula (64).
  • R 601 to R 624 which are not a monovalent group represented by the formula (64) are each independently Hydrogen atom, 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-forming 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 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
  • the compound represented by the formula (61) is represented by any of the following formulas (61-7) to (61-18).
  • X 601 is as defined in the formula (61). * Represents a single bond bonded to the monovalent group represented by the formula (64).
  • R 601 to R 624 are the same as R 601 to R 624 which are not a monovalent group represented by the formula (64).
  • R 601 to R 608 which do not form the divalent group represented by the formulas (62) and (63) and are not the monovalent group represented by the formula (64);
  • R 611 to R 614 and R 621 to R 624 which are not monovalent groups represented by 64) are preferably each independently Hydrogen atom, 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 631 to R 640 are independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted
  • HAr 601 is a structure represented by the following formula (67).
  • X 602 is an oxygen atom or a sulfur atom. Any one of R 641 to R 648 is a single bond bonded to L 603 .
  • R 641 to R 648 which are not a single bond are each independently Hydrogen atom, 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-forming 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 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.
  • a 701 ring and A 702 ring are each independently A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms. At least one selected from the group consisting of the ring A 701 and the ring A 702 bonds to a bond * of a structure represented by the following formula (72).
  • a 703 rings are each independently: A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
  • X 701 is NR 703 , C (R 704 ) (R 705 ), Si (R 706 ) (R 707 ), Ge (R 708 ) (R 709 ), O, S or Se.
  • R 701 and R 702 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.
  • R 701 and R 702 which do not form a substituted or unsubstituted saturated or unsaturated ring, and R 703 to R 709 are each independently Hydrogen atom, 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-forming 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstit
  • the group represented by the following formula (73) to one or both of the A 701 ring and A 702 ring is bonded.
  • Ar 701 and Ar 702 are each independently A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L 701 to L 703 are each independently Single bond, A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or a divalent linking group formed by combining 2 to 4 of these.
  • the ring-forming carbon atom of the aromatic hydrocarbon ring of the ring A 702 or the ring-forming atom of the heterocyclic ring has a bond of a structure represented by the formula (72). Combine with *.
  • the structures represented by formula (72) may be the same or different.
  • R 701 and R 702 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. In one embodiment, R 701 and R 702 combine with each other to form a fluorene structure.
  • Ring A 701 and Ring A 702 are a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.
  • ring A 703 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.
  • X 701 is O or S.
  • the compound represented by the formula (81) will be described.
  • the ring A 801 is a ring represented by the formula (82) fused at an arbitrary position of an adjacent ring.
  • the ring A 802 is a ring represented by the formula (83) fused at an arbitrary position of an adjacent ring.
  • the two bonding hands * bond to an arbitrary position on the A803 ring.
  • X 801 and X 802 are each independently C (R 803 ) (R 804 ), Si (R 805 ) (R 806 ), an oxygen atom, or a sulfur atom.
  • Ring A 803 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.
  • Ar 801 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • R 801 to R 806 are each independently Hydrogen atom, 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-forming 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 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.
  • R 901 to R 907 are as defined in the above formula (1).
  • m801 and m802 are each independently an integer of 0 to 2. When these are 2, a plurality of R 801 or R 802 may be the same as or different from each other.
  • a801 is an integer of 0 to 2. When a801 is 0 or 1, the structures in parentheses represented by “3-a801” may be the same or different. If a801 is 2, to Ar 801 may be the same as each other or may be different. )
  • Ar 801 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • ring A 803 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or It is a substituted or unsubstituted anthracene ring.
  • R 803 and R 804 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • a801 is 1.
  • the content of the compound (host material) represented by the formula (1) in the light emitting layer is preferably 80% by mass or more and 99% by mass or less based on the entire light emitting layer.
  • the content in the light emitting layer is preferably 1% by mass or more and 20% by mass or less based on the entire light emitting layer.
  • 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.
  • the flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate 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.
  • 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 oxide-tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide silicon oxide
  • tungsten oxide tungsten oxide
  • indium oxide containing zinc oxide Graphene
  • gold (Au) platinum
  • Pt platinum
  • a nitride of a metal material for example, titanium nitride
  • the hole-injection layer is a layer containing a substance having a high hole-injection property.
  • Materials having a high hole-injecting property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, aromatic amine compounds, or high molecular compounds (oligomers, dendrimers, polymers, and the like) can also be used.
  • the hole-transporting layer is a layer containing a substance having a high hole-transporting property.
  • An aromatic amine compound, a carbazole derivative, an anthracene derivative or the like can be used for the hole transport layer.
  • a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK N-vinylcarbazole
  • PVTPA poly (4-vinyltriphenylamine
  • any substance other than these substances may be used as long as it has a property of transporting more holes than electrons.
  • the layer containing a substance having a high hole-transport property is not limited to a single layer, and may be a layer in which two or more layers of the above substances are stacked.
  • the light-emitting layer is a layer containing a substance having a high light-emitting property, and various materials can be used.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as the substance having a high light emitting property.
  • the fluorescent compound is a compound capable of emitting light from a singlet excited state
  • the phosphorescent compound is a compound capable of emitting light from a triplet excited state.
  • a blue fluorescent light-emitting material that can be used for the light-emitting layer
  • 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.
  • a green fluorescent light emitting material that can be used for the light emitting layer
  • an aromatic amine derivative or the like can be used.
  • a red fluorescent light emitting material that can be used for the light emitting layer
  • a tetracene derivative, a diamine derivative, or the like can be used.
  • a metal complex such as an iridium complex, an osmium complex, and a platinum complex is used.
  • An iridium complex or the like is used as a green phosphorescent material that can be used for the light emitting layer.
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used as a red phosphorescent light emitting material that can be used for the light emitting layer.
  • the light-emitting layer may have a structure in which the above substance having a high light-emitting property (guest material) is dispersed in another substance (host material).
  • guest material the above substance having a high light-emitting property
  • host material another substance
  • LUMO level the lowest unoccupied orbital level
  • HOMO level the lowest unoccupied orbital level
  • a substance (host material) for dispersing a substance having a high light-emitting property 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; A heterocyclic compound, 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative; 3) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative; used.
  • the electron-transporting layer is a layer containing a substance having a high electron-transporting property.
  • a metal complex such as an aluminum complex, a beryllium complex or a zinc complex
  • a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative or a phenanthroline derivative
  • 3) a polymer compound can be used.
  • the electron-injection layer is a layer containing a substance having a high electron-injection property.
  • a substance having a high electron-injection property lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 8-hydroxyquinolinolato-lithium (Liq), etc.
  • an alkali metal such as lithium oxide (LiO x ), an alkaline earth metal, or a compound thereof.
  • cathode It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode.
  • a cathode material include elements belonging to Group 1 or Group 2 of the periodic table, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium ( Alkaline earth metals such as Ca) and strontium (Sr); alloys containing these (eg, MgAg, AlLi); rare earth metals such as europium (Eu) and ytterbium (Yb); and alloys containing these.
  • a method for forming each layer is not particularly limited.
  • a conventionally known formation method such as a vacuum evaporation method and a spin coating method can be used.
  • Each layer such as a light-emitting layer is formed by a known method such as a vacuum evaporation method, a molecular beam evaporation method (MBE method), or 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. It can be formed by a method.
  • MBE method molecular beam evaporation method
  • the thickness of each layer is not particularly limited, but is generally from several nm to suppress defects such as pinholes, suppress applied voltage, and improve luminous efficiency. A range of 1 ⁇ m is preferred.
  • An electronic device includes the organic EL element according to one embodiment of the present invention.
  • the electronic device include a display component such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, and a light emitting device such as a lighting device or a vehicular lamp.
  • Synthesis Example 4 [Synthesis of Compound BH-4]
  • Synthesis Example 1 1.4 g (5%) of benzo [b] naphtho [1,2-d] furan-10-boronic acid was used instead of benzo [b] naphtho [2,3-d] furan-2-boronic acid.
  • the reaction was performed in the same manner as above except that 1.7 g of white crystals were obtained.
  • the obtained compound was subjected to FD-MS analysis and identified as the following compound BH-4 (yield 71%).
  • Synthesis Example 5 [Synthesis of Compound BH-5]
  • benzo [b] naphtho [2,1-d] furan-8-boronic acid was replaced by 1.4 g (5 .3 mmol) was used, and the reaction was performed in the same manner to obtain 1.6 g of white crystals.
  • the obtained compound was subjected to FD-MS analysis and identified as the following compound BH-5 (yield 65%).
  • Synthesis Example 6 [Synthesis of Compound BH-6]
  • benzo [b] naphtho [2,3-d] furan-1-boronic acid was replaced by 1.4 g (5 .3 mmol) was used, and the same reaction was performed to obtain 1.4 g of white crystals.
  • the obtained compound was subjected to FD-MS analysis and identified as the following compound BH-6 (yield 57%).
  • Synthesis Example 8 [Synthesis of Compound BH-8]
  • benzo [b] naphtho [2,1-d] furan-7-boronic acid was replaced by 1.4 g (5 .3 mmol) was used, and the reaction was performed in the same manner to obtain 1.6 g of white crystals.
  • the obtained compound was subjected to FD-MS analysis and identified as the following compound BH-8 (yield 65%).
  • Synthesis Example 13 [Synthesis of Compound BH-13]
  • Synthesis Example 1 1.4 g (5%) of benzo [b] naphtho [2,1-d] furan-6-boronic acid was used instead of benzo [b] naphtho [2,3-d] furan-2-boronic acid. .3 mmol) was used, and the reaction was performed in the same manner to obtain 1.2 g of white crystals.
  • the obtained compound was subjected to FD-MS analysis and identified as the following compound BH-13 (yield 50%).
  • Synthesis Example 14 [Synthesis of Compound BH-14]
  • 4- (benzo [b] naphtho [2,3-d] furan-1-yl) phenylboronic acid was used instead of benzo [b] naphtho [2,3-d] furan-2-boronic acid.
  • 1.8 g (5.3 mmol) was used, 1.5 g of white crystals were obtained.
  • the obtained compound was subjected to FD-MS analysis and identified as the following compound BH-14 (yield 55%).
  • Synthesis Example 16 [Synthesis of Compound BH-16]
  • benzo [b] naphtho [1,2-d] furan-10-boronic acid was replaced with 1.4 g (5 .3 mmol) was used and the reaction was carried out in the same manner to obtain 1.5 g of white crystals.
  • the obtained compound was subjected to FD-MS analysis and identified as the following compound BH-16 (yield 56%).
  • Example 1 (Production of organic EL element) A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm. The cleaned glass substrate with a transparent electrode is mounted on a substrate holder of a vacuum vapor deposition apparatus, and a compound HI is vapor-deposited so that the transparent electrode is first covered on the surface on which the transparent electrode is formed to form a HI film having a thickness of 5 nm. A film was formed. This HI film functions as a hole injection layer.
  • ITO transparent electrode anode
  • UV ozone cleaning for 30 minutes.
  • the film thickness of ITO was 130 nm.
  • the cleaned glass substrate with a transparent electrode is mounted on a substrate holder of a vacuum vapor deposition apparatus, and a compound
  • the compound HT-1 was vapor-deposited to form an HT-1 film having a film thickness of 80 nm on the HI film.
  • This HT-1 film functions as a hole transport layer (first hole transport layer).
  • a compound HT-2 was deposited, and a 10 nm-thick HT-2 film was formed on the HT-1 film.
  • This HT-2 film functions as an electron blocking layer (second hole transport layer).
  • Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the HT-2 film so that the ratio of compound BD-1 was 4% by mass, and BH-1 having a film thickness of 25 nm: A BD-1 film was formed.
  • This BH-1: BD-1 film functions as a light emitting layer.
  • Compound ET-1 was deposited on this light emitting layer to form a 10 nm-thick ET-1 film. This ET-1 film functions as a hole barrier layer.
  • Compound ET-2 was deposited on the ET-1 film to form a 15 nm-thick ET-2 film. This ET-2 film functions as an electron transport layer.
  • LiF was deposited on the ET-2 film to form a 1 nm-thick LiF film.
  • Metal Al was vapor-deposited on this LiF film to form a metal cathode having a film thickness of 80 nm, and an organic EL device was produced.
  • the layer structure of the obtained organic EL device is as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / BH-1: BD-1 (25: 4% by mass) / ET-1 (10) / ET-2 ( 15) / LiF (1) / Al (80)
  • the numbers in parentheses indicate the film thickness (unit: nm).
  • Example 1 The materials used in Example 1 and Examples and Comparative Examples described later are shown below.
  • Comparative Examples 1-1 and 1-2 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. The results are shown in Table 1.
  • Example 2 and Comparative Example 2 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. Table 2 shows the results.
  • Example 3 Comparative Examples 3-1 and 3-2 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. The results are shown in Table 3.
  • Example 4 Comparative Example 4-1, Comparative Example 4-2 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. The results are shown in Table 4.
  • Example 5 Comparative Example 5 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. Table 5 shows the results.
  • Example 6 Comparative Example 6 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. The results are shown in Table 6.
  • Example 11 and Comparative Example 11 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). Table 7 shows the results.
  • Example 12 Comparative Example 12 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). Table 8 shows the results.
  • Example 13 Comparative Example 13 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 9.
  • Example 14 Comparative Example 14 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 10.
  • Example 15 and Comparative Example 15 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 11.
  • Example 16 Comparative Example 16 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 12.
  • Example 17 Comparative Example 17 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 13.
  • Example 18 Comparative Example 18 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 14.
  • Example 21 Comparative Example 21 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 15.
  • Example 22 Comparative Example 22 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 16.
  • Example 23 Comparative Example 23 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 17.
  • Example 24 Comparative Example 24 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 18.
  • Example 25 Comparative Example 25 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 19.
  • Example 26 Comparative Example 26 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 20.
  • Example 27 Comparative Example 27 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 21.
  • Example 28 Comparative Example 28 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 22.
  • Example 31 Comparative Example 31 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 23.
  • Example 32 Comparative Example 32 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 24.
  • Example 33 Comparative Example 33 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 25.
  • Example 34 Comparative Example 34 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 26.
  • Example 35 Comparative Example 35 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 27.
  • Example 36 Comparative Example 36 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 28.
  • Example 37 Comparative Example 37 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 29.
  • Example 38 Comparative Example 38 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 30.
  • Example 41 Comparative Example 41 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 31.
  • Example 42 Comparative Example 42 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 32.
  • Example 43 Comparative Example 43 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 33.
  • Example 44 Comparative Example 44 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 34.
  • Example 45 Comparative Example 45 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 35.
  • Example 46 Comparative Example 46 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 36.
  • Example 47 Comparative Example 47 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 37.
  • Example 48 Comparative Example 48 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 38.
  • Example 51 Comparative Example 51 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 39.
  • Example 52 Comparative Example 52 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 40.
  • Example 53 Comparative Example 53 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 41.
  • Example 54 Comparative Example 54 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 42.
  • Example 55 Comparative Example 55 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 43.
  • Example 56 Comparative Example 56 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 44.
  • Example 57 Comparative Example 57 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 45.
  • Example 58 Comparative Example 58 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 46.
  • Example 61 Comparative Example 61 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 47.
  • Example 62 Comparative Example 62 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 48.
  • Example 63 Comparative Example 63 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 49.
  • Example 64 Comparative Example 64 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 50.
  • Example 65 Comparative Example 65 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 51.
  • Example 66 Comparative Example 66 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 52.
  • Example 67 Comparative example 67 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 53.
  • Example 68 Comparative Example 68 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 54.
  • Example 69 Comparative example 69 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 55.
  • Example 70 Comparative Example 70 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 56.
  • Example 71 Comparative example 71 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 57.
  • Example 72 Comparative Example 72 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 58.
  • Example 73 Comparative Example 73 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 59.
  • Example 74 Comparative Example 74 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 60.
  • Example 75 Comparative Example 75 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 61.
  • Example 76 Comparative Example 76 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 62.
  • Example 77 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 63.
  • Example 78 Comparative Example 78 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 64.
  • Comparative Example 79 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 65.
  • Example 80 Comparative Example 80 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 66.
  • Example 81 Comparative Example 81 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 67.
  • Example 82 Comparative Example 82 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 68.
  • Example 83 Comparative Example 83 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 69.
  • Example 84 Comparative Example 84 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 70.
  • Example 85 Comparative Example 85 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 71.
  • Example 86 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 72.
  • Example 87 Comparative Example 87 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 73.
  • Comparative Example 88 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 74.
  • Example 89 Comparative Example 89 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 75.
  • Example 90 Comparative Example 90 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 76.
  • Example 91 Comparative example 91 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 77.
  • Example 92 Comparative Example 92 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 78.
  • Example 93 Comparative Example 93 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 79.
  • Example 94 Comparative example 94 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 80.
  • Example 95 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 81.
  • Example 96 Comparative Example 96 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 82.
  • Comparative Example 97 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 83.
  • Example 98 Comparative Example 98 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 84.
  • Example 99 Comparative Example 99 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 85.
  • Example 100 Comparative example 100 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 86.
  • Example 101 Comparative Example 101 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 87.
  • Example 102 Comparative Example 102 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 88.
  • Example 103 Comparative Example 103 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 89.
  • Example 104 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 90.
  • Example 105 Comparative Example 105 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 91.
  • Comparative Example 106 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 92.
  • Example 107 Comparative Example 107 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 93.
  • Example 108 Comparative Example 108 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 94.
  • Example 109 Comparative Example 109 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 95.
  • Example 110 Comparative Example 110 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 96.
  • Example 111 Comparative Example 111 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 97.
  • Example 112 Comparative example 112 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 98.
  • Example 113 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 99.
  • Example 114 Comparative example 114 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 100.
  • Comparative Example 115 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 101.
  • Example 116 Comparative Example 116 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 102.
  • Example 117 Comparative Example 117 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 103.
  • Example 118 Comparative example 118 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 104.
  • Example 119 Comparative Example 119 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 105.
  • Example 120 Comparative Example 120 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 106.
  • Example 121 Comparative Example 121 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 107.
  • Example 122 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 108.
  • Example 123 Comparative Example 123 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 109.
  • Comparative Example 124 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 110.
  • Example 125 Comparative Example 125 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 111.
  • Example 126 Comparative example 126 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 112.
  • Example 127 Comparative Example 127 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 113.
  • Example 128, Comparative Example 128 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 114.
  • Example 129 Comparative Example 129 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 115.
  • Example 130 Comparative Example 130 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 116.
  • Example 131 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 117.
  • Example 132 Comparative example 132 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 118.

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Abstract

Composé représenté par la formule (1) (dans la formule (1), au moins un radical R1-R8 est un atome de deutérium et Ar2 est un groupe monovalent représenté par la formule (2), (3), ou (4)).
PCT/JP2019/039915 2018-10-09 2019-10-09 Nouveau composé, élément électroluminescent organique et dispositif électronique WO2020075783A1 (fr)

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CN201980066845.1A CN112789269A (zh) 2018-10-09 2019-10-09 新型的化合物、有机电致发光元件、电子设备
KR1020217010389A KR20210075089A (ko) 2018-10-09 2019-10-09 신규 화합물, 유기 일렉트로루미네센스 소자, 전자 기기
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US16/557,725 US10777752B2 (en) 2018-10-09 2019-08-30 Organic electroluminescence device and electronic apparatus provided with the same
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WO2022124320A1 (fr) * 2020-12-09 2022-06-16 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
WO2022181072A1 (fr) * 2021-02-26 2022-09-01 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
WO2022270428A1 (fr) * 2021-06-25 2022-12-29 出光興産株式会社 Poudre mélangée pour élément électroluminescent organique et procédé de fabrication de poudre mélangée, procédé de fabrication d'un élément électroluminescent organique à l'aide de poudre mélangée, procédé de sélection de composé en poudre mélangée et composition pour dépôt sous vide

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KR102564940B1 (ko) * 2019-11-21 2023-08-08 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR102667148B1 (ko) * 2020-01-21 2024-05-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
US12096687B2 (en) 2020-07-22 2024-09-17 Rohm And Haas Electronic Materials Korea Ltd. Plurality of light-emitting materials, organic electroluminescent compound, and organic electroluminescent device comprising the same
KR102716879B1 (ko) * 2020-12-09 2024-10-14 주식회사 엘지화학 유기 발광 소자
WO2023096387A1 (fr) * 2021-11-26 2023-06-01 에스에프씨 주식회사 Nouveau composé anthracène organique et dispositif électroluminescent organique le comprenant
KR20240020458A (ko) * 2022-08-08 2024-02-15 주식회사 엘지화학 유기 발광 소자
WO2024210019A1 (fr) * 2023-04-04 2024-10-10 出光興産株式会社 Composé, composition, élément électroluminescent organique et dispositif électronique

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