WO2022186390A1 - Élément électroluminescent organique et dispositif électronique - Google Patents

Élément électroluminescent organique et dispositif électronique Download PDF

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WO2022186390A1
WO2022186390A1 PCT/JP2022/009515 JP2022009515W WO2022186390A1 WO 2022186390 A1 WO2022186390 A1 WO 2022186390A1 JP 2022009515 W JP2022009515 W JP 2022009515W WO 2022186390 A1 WO2022186390 A1 WO 2022186390A1
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substituted
group
ring
unsubstituted
carbon atoms
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ピエール ブフレ
昭辰 林
トビアス カンツラ－
ペーター ミュラー
アニッキ サンタラ
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出光興産株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces

Definitions

  • the present invention relates to organic electroluminescence elements and electronic devices.
  • organic electroluminescence device When a voltage is applied to an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device"), holes are injected into the light-emitting layer from the anode, and electrons are injected into the light-emitting layer from the cathode. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75% according to the electron spin statistical law.
  • Organic EL elements are applied to full-color displays for mobile phones, televisions, and the like. In order to improve the performance of organic EL devices, various studies have been made on compounds used in organic EL devices.
  • Patent Document 1 discloses a polycyclic heterocyclic compound containing a nitrogen atom and a boron atom as a compound that can be used in an organic EL device.
  • Performance of an organic EL element includes, for example, luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and life.
  • An object of the present invention is to provide an organic electroluminescence element that can have a long life and an electronic device equipped with the organic electroluminescence element.
  • an organic electroluminescence device having an anode, a cathode, and a light-emitting layer included between the anode and the cathode, wherein the light-emitting layer is represented by the following general formula (1 ) is provided, containing the first compound represented by the organic electroluminescence device.
  • an electronic device equipped with the above-described organic electroluminescence element according to one aspect of the present invention.
  • an organic electroluminescence element capable of extending the life and an electronic device equipped with the organic electroluminescence element.
  • FIG. 4 is a diagram showing a schematic configuration of another example of the organic electroluminescence device according to the second embodiment
  • a hydrogen atom includes isotopes with different neutron numbers, ie, protium, deuterium, and tritium.
  • a hydrogen atom that is, a hydrogen atom, a deuterium atom, or Assume that the tritium atoms are bonded.
  • the number of ring-forming carbon atoms refers to the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). represents the number of carbon atoms among the atoms that When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same applies to the "number of ring-forming carbon atoms" described below unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms
  • the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
  • the number of ring-forming carbon atoms in the benzene ring substituted with the alkyl group is 6.
  • the naphthalene ring substituted with an alkyl group has 10 ring-forming carbon atoms.
  • the number of ring-forming atoms refers to compounds (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compound, and heterocyclic compound) represents the number of atoms constituting the ring itself. Atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom that constitutes a ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below unless otherwise specified.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of atoms forming the pyridine ring. Therefore, the number of ring-forming atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is 6.
  • the expression "substituted or unsubstituted XX to YY carbon number ZZ group” represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in the substituents.
  • "YY” is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and "YY” means an integer of 2 or more.
  • an unsubstituted ZZ group represents a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group is a "substituted or unsubstituted ZZ group”. is a "substituted ZZ group”.
  • "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
  • a hydrogen atom in the "unsubstituted ZZ group” is a protium atom, a deuterium atom, or a tritium atom.
  • substituted in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substituted in the case of "a BB group substituted with an AA group” similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the number of ring-forming carbon atoms in the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
  • the number of ring-forming atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified. be.
  • the number of carbon atoms in the "unsubstituted alkyl group” described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
  • the number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified. be.
  • the number of ring-forming carbon atoms in the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
  • the number of ring-forming atoms of the "unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5, unless otherwise specified herein. ⁇ 18.
  • the number of carbon atoms in the "unsubstituted alkylene group” described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
  • 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” It refers to a "substituted aryl group."
  • the term “aryl group” includes both "unsubstituted aryl group” and "substituted aryl group.”
  • a "substituted aryl group” means a group in which one or more hydrogen atoms of an "unsubstituted aryl group” are replaced with a substituent.
  • substituted aryl group examples include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group” of Specific Example Group G1A below is replaced with a substituent, and a substituted aryl group of Specific Example Group G1B below.
  • Examples include:
  • the examples of the "unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are only examples, and the “substituted aryl group” described herein includes the following specific examples A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group” of Group G1B is further replaced with a substituent, and the hydrogen atom of the substituent in the "substituted aryl group” of Specific Example Group G1B below Furthermore, groups substituted with substituents are also included.
  • aryl group (specific example group G1A): phenyl group, a p-biphenyl group, m-biphenyl group, an o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chryseny
  • aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, an ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, an ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl) fluorenyl group, a cyanophenyl group,
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
  • a “heterocyclic group” as described herein is a monocyclic group or a condensed ring group.
  • a “heterocyclic group” as described herein is either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • specific examples of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic groups (specific example group G2A), and substituted heterocyclic groups ( Specific example group G2B) and the like can be mentioned.
  • unsubstituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”, and substituted heterocyclic group refers to “substituted or unsubstituted "Heterocyclic group” refers to a "substituted heterocyclic group”.
  • heterocyclic group refers to a "substituted heterocyclic group”.
  • a “substituted heterocyclic group” means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” of the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups of the following specific example group G2B. mentioned.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are only examples, and the "substituted heterocyclic group” described herein specifically includes A group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of Example Group G2B is further replaced with a substituent, and a substituent in the "substituted heterocyclic group" of Specific Example Group G2B A group in which a hydrogen atom of is further replaced with a substituent is also included.
  • Specific example group G2A includes, for example, the following nitrogen atom-containing unsubstituted heterocyclic groups (specific example group G2A1), oxygen atom-containing unsubstituted heterocyclic groups (specific example group G2A2), sulfur atom-containing unsubstituted (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • nitrogen atom-containing unsubstituted heterocyclic groups specifically example group G2A1
  • oxygen atom-containing unsubstituted heterocyclic groups specifically example group G2A2
  • sulfur atom-containing unsubstituted specifically example group G2A3
  • a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), substituted heterocyclic group containing an oxygen atom (specific example group G2B2), substituted heterocyclic ring containing a sulfur atom group (specific example group G2B3), and one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) as a substituent Including substituted groups (example group G2B4).
  • an unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, quinolyl group, an isoquinolyl group, cinnolyl group, a phthalazinyl group, a quinazolinyl
  • an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, azanaphthobenzofuranyl group and diazanaphthobenzofuranyl group;
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic groups derived from the represented ring structures include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 .
  • a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl) phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group and a biphenylquinazolinyl group;
  • a substituted heterocyclic group containing an oxygen atom (specific example group G2B2): a phenyldibenzofuranyl group, methyldibenzofuranyl group, A t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
  • a substituted heterocyclic group containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
  • the "one or more hydrogen atoms of the monovalent heterocyclic group” means a hydrogen atom bonded to the ring-forming carbon atom of the monovalent heterocyclic group, and at least one of X A and Y A is NH and one or more hydrogen atoms of a methylene group when one of X A and Y A is CH 2 .
  • unsubstituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is “unsubstituted alkyl group”
  • substituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is It refers to a "substituted alkyl group”.
  • alkyl group includes both an "unsubstituted alkyl group” and a "substituted alkyl group”.
  • a “substituted alkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group” (specific example group G3A) are replaced with substituents, and substituted alkyl groups (specific examples Examples of group G3B) and the like can be mentioned.
  • the alkyl group in the "unsubstituted alkyl group” means a chain alkyl group.
  • the "unsubstituted alkyl group” includes a linear “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are only examples, and the "substituted alkyl group” described herein includes specific example group G3B A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group” of Specific Example Group G3B is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group” of Specific Example Group G3B is further replaced by a substituent included.
  • - unsubstituted alkyl group (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
  • Substituted alkyl group (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group;
  • Substituted or unsubstituted alkenyl group Specific examples of the "substituted or unsubstituted alkenyl group" described in the specification (specific example group G4) include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B) and the like.
  • unsubstituted alkenyl group refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group", "substituted alkenyl group” means "substituted or unsubstituted alkenyl group ” is a “substituted alkenyl group”.
  • alkenyl group simply referring to an “alkenyl group” includes both an “unsubstituted alkenyl group” and a “substituted alkenyl group”.
  • a “substituted alkenyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include groups in which the following "unsubstituted alkenyl group” (specific example group G4A) has a substituent, and substituted alkenyl groups (specific example group G4B). be done.
  • - unsubstituted alkenyl group (specific example group G4A): a vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.
  • - substituted alkenyl group (specific example group G4B): 1,3-butandienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, a 2-methylallyl group and a 1,2-dimethylallyl group;
  • Substituted or unsubstituted alkynyl group Specific examples of the "substituted or unsubstituted alkynyl group" described in the specification (specific example group G5) include the following unsubstituted alkynyl groups (specific example group G5A).
  • unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group” is "unsubstituted alkynyl group”.
  • alkynyl group means "unsubstituted includes both "alkynyl group” and "substituted alkynyl group”.
  • a “substituted alkynyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group” (specific example group G5A) are replaced with substituents.
  • Substituted or unsubstituted cycloalkyl group Specific examples of the "substituted or unsubstituted cycloalkyl group” described in the specification (specific example group G6) include the following unsubstituted cycloalkyl groups (specific example group G6A), and substituted cycloalkyl groups ( Specific example group G6B) and the like can be mentioned.
  • unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group” is “unsubstituted cycloalkyl group", and substituted cycloalkyl group refers to "substituted or unsubstituted It refers to the case where "cycloalkyl group” is “substituted cycloalkyl group”.
  • cycloalkyl group means "unsubstituted cycloalkyl group” and “substituted cycloalkyl group”. including both.
  • a “substituted cycloalkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group” (specific example group G6A) are replaced with substituents, and substituted cycloalkyl groups (Specific example group G6B) and the like.
  • the examples of the "unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed here are only examples, and the "substituted cycloalkyl group” described herein specifically includes A group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the “substituted cycloalkyl group” of Example Group G6B is replaced with a substituent, and in the “substituted cycloalkyl group” of Specific Example Group G6B A group in which a hydrogen atom of a substituent is further replaced with a substituent is also included.
  • an unsubstituted cycloalkyl group (specific example group G6A): a cyclopropyl group, cyclobutyl group, a cyclopentyl group, a cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • G7 A group represented by -Si (R 901 ) (R 902 ) (R 903 )
  • Specific examples of the group represented by —Si(R 901 )(R 902 )(R 903 ) described in the specification include: -Si(G1)(G1)(G1), - Si (G1) (G2) (G2), - Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3) and -Si(G6)(G6)(G6) are mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G1's in -Si(G1)(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -Si (G1) (G2) (G2) are the same or different from each other.
  • a plurality of G1's in -Si(G1)(G1)(G2) are the same or different from each other.
  • a plurality of G2 in -Si(G2)(G2)(G2) are the same or different from each other.
  • a plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other.
  • a plurality of G6 in -Si(G6)(G6)(G6) are the same or different from each other.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G9 A group represented by -S- (R 905 )
  • Specific examples of the group represented by -S-(R 905 ) described in the specification include: -S(G1), -S(G2), -S (G3) and -S (G6) is mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G1's in -N(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -N(G2)(G2) are the same or different from each other.
  • a plurality of G3s in -N(G3)(G3) are the same or different from each other.
  • a plurality of G6 in -N(G6)(G6) are the same or different from each other.
  • halogen atom described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • Substituted or unsubstituted fluoroalkyl group means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a fluorine atom. Also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms.
  • the carbon number of the “unsubstituted fluoroalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • a "substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of a “fluoroalkyl group” are replaced with a substituent.
  • substituted fluoroalkyl group described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and A group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group” is further replaced with a substituent is also included.
  • Specific examples of the "unsubstituted fluoroalkyl group” include groups in which one or more hydrogen atoms in the above “alkyl group” (specific example group G3) are replaced with fluorine atoms.
  • Substituted or unsubstituted haloalkyl group "Substituted or unsubstituted haloalkyl group” described herein means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom Also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the carbon number of the “unsubstituted haloalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • a "substituted haloalkyl group” means a group in which one or more hydrogen atoms of a “haloalkyl group” are replaced with a substituent.
  • the "substituted haloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent group, and a “substituted A group in which one or more hydrogen atoms of the substituent in the "haloalkyl group of" is further replaced with a substituent is also included.
  • Specific examples of the "unsubstituted haloalkyl group” include groups in which one or more hydrogen atoms in the above “alkyl group” (specific example group G3) are replaced with halogen atoms.
  • a haloalkyl group may be referred to as a halogenated alkyl group.
  • Substituted or unsubstituted alkoxy group A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group".
  • the carbon number of the "unsubstituted alkoxy group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • Substituted or unsubstituted alkylthio group A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted unsubstituted alkyl group".
  • the carbon number of the "unsubstituted alkylthio group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • Substituted or unsubstituted aryloxy group Specific examples of the “substituted or unsubstituted aryloxy group” described in this specification are groups represented by —O(G1), where G1 is the “substituted or an unsubstituted aryl group”.
  • the number of ring-forming carbon atoms in the "unsubstituted aryloxy group” is 6-50, preferably 6-30, more preferably 6-18, unless otherwise specified in the specification.
  • ⁇ "Substituted or unsubstituted trialkylsilyl group” Specific examples of the "trialkylsilyl group” described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the group described in Specific Example Group G3. It is a "substituted or unsubstituted alkyl group”. A plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group” is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified in the specification.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the group described in Specific Example Group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • an "aralkyl group” is a group in which a hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one aspect of a “substituted alkyl group”.
  • An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group", and the number of carbon atoms in the "unsubstituted aralkyl group” is unless otherwise specified herein. , 7-50, preferably 7-30, more preferably 7-18.
  • substituted or unsubstituted aralkyl group include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • a substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl- 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group,
  • substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenyl, unless otherwise stated herein.
  • nantholinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-
  • a carbazolyl group is specifically any one of the following groups unless otherwise specified in the specification.
  • the (9-phenyl)carbazolyl group is specifically any one of the following groups, unless otherwise stated in the specification.
  • a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t- butyl group and the like.
  • the "substituted or unsubstituted arylene group” described herein is derived from the above "substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. is the base of the valence.
  • Specific examples of the “substituted or unsubstituted arylene group” include the “substituted or unsubstituted aryl group” described in specific example group G1 by removing one hydrogen atom on the aryl ring. Induced divalent groups and the like can be mentioned.
  • Substituted or unsubstituted divalent heterocyclic group Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group” described herein is the above “substituted or unsubstituted heterocyclic group” except that one hydrogen atom on the heterocyclic ring is removed. is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocyclic ring from the "substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include divalent groups derived by removing atoms.
  • Substituted or unsubstituted alkylene group Unless otherwise specified, the "substituted or unsubstituted alkylene group” described herein is derived from the above “substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. is the base of the valence. Specific examples of the "substituted or unsubstituted alkylene group” (specific example group G14) include the "substituted or unsubstituted alkyl group” described in specific example group G3 by removing one hydrogen atom on the alkyl chain. Induced divalent groups and the like can be mentioned.
  • the substituted or unsubstituted arylene group described in this specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • * represents a binding position.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Formulas Q9 and Q10 may be linked together through a single bond to form a ring.
  • * represents a binding position.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents a binding position.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein is.
  • Q 1 to Q 9 are each independently a hydrogen atom or a substituent.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • R 921 and R 922 when “one or more pairs of two or more adjacent pairs of R 921 to R 930 are combined to form a ring", is a pair of R 921 and R 922 , a pair of R 922 and R 923 , a pair of R 923 and R 924 , a pair of R 924 and R 930 , a pair of R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R 929 and R 921 .
  • one or more pairs means that two or more of the groups consisting of two or more adjacent groups may form a ring at the same time.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 925 and R 926 are bonded together to form ring Q B
  • the general formula (TEMP-103) The represented anthracene compound is represented by the following general formula (TEMP-104).
  • a group consisting of two or more adjacent pairs forms a ring is not limited to the case where a group consisting of two adjacent "two” bonds as in the above example, but It also includes the case where a pair is combined.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 922 and R 923 are bonded together to form ring Q C
  • the adjacent three R 921 , R 922 and R 923
  • the anthracene compound represented by the above general formula (TEMP-103) has It is represented by the general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “condensed ring” to be formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when “one pair of adjacent pairs" forms a “single ring” or a “fused ring", the “single ring” or “fused ring” is a saturated ring, or Unsaturated rings can be formed.
  • ring Q A and ring Q B formed in the general formula (TEMP-104) are each a “monocyclic ring” or a "fused ring”.
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) form a condensed ring by condensing the ring Q A and the ring Q C. If the ring Q A of the general formula (TMEP-104) is a benzene ring, the ring Q A is monocyclic. When the ring Q A of the general formula (TMEP-104) is a naphthalene ring, the ring Q A is a condensed ring.
  • Unsaturated ring means an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a “saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.
  • Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in the specific example group G1 are terminated with a hydrogen atom.
  • Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups listed as specific examples in the specific example group G2 are terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in the specific example group G6 are terminated with a hydrogen atom.
  • Forming a ring means forming a ring only with a plurality of atoms of the mother skeleton, or with a plurality of atoms of the mother skeleton and one or more arbitrary elements.
  • the ring Q A formed by combining R 921 and R 922 shown in the general formula (TEMP-104) has the carbon atom of the anthracene skeleton to which R 921 is bonded and the anthracene to which R 922 is bonded. It means a ring formed by a skeleton carbon atom and one or more arbitrary elements.
  • R 921 and R 922 form a ring Q A , the carbon atom of the anthracene skeleton to which R 921 is bound, the carbon atom of the anthracene skeleton to which R 922 is bound, and four carbon atoms and form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.
  • the "arbitrary element” is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise specified in this specification.
  • a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an “optional substituent” described later.
  • the ring formed is a heterocycle.
  • One or more arbitrary elements constituting a monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, unless otherwise specified in the present specification. , more preferably 3 or more and 5 or less.
  • “monocyclic ring” and “condensed ring” “monocyclic ring” is preferred, unless otherwise stated in the present specification.
  • the “saturated ring” and the “unsaturated ring” the “unsaturated ring” is preferred, unless otherwise specified in the present specification.
  • “monocyclic” is preferably a benzene ring.
  • the “unsaturated ring” is preferably a benzene ring.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above “monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section “Substituents described herein” above.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above "monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section "Substituents described herein" above. The above is the case where “one or more pairs of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic ring", and “one or more pairs of two or more adjacent pairs are combined with each other to form a substituted or unsubstituted condensed ring"("combine to form a ring").
  • the substituent in the case of “substituted or unsubstituted” is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), halogen atom, cyano group, nitro group, a group selected from the group consisting of an unsubstituted aryl group
  • the two or more R 901 are the same or different from each other, when two or more R 902 are present, the two or more R 902 are the same or different from each other; when two or more R 903 are present, the two or more R 903 are the same or different from each other, when two or more R 904 are present, the two or more R 904 are the same or different from each other; when two or more R 905 are present, the two or more R 905 are the same or different from each other, when two or more R 906 are present, the two or more R 906 are the same or different from each other; When two or more R 907 are present, the two or more R 907 are the same or different from each other.
  • the substituents referred to above as "substituted or unsubstituted” are an alkyl group having 1 to 50 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituents referred to above as "substituted or unsubstituted” are an alkyl group having 1 to 18 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may form a “saturated ring” or an “unsaturated ring”, preferably a substituted or unsubstituted saturated 5 forming a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
  • any substituent may have further substituents. Substituents further possessed by the optional substituents are the same as the above optional substituents.
  • the numerical range represented using “AA to BB” has the numerical value AA described before “AA to BB” as the lower limit, and the numerical value BB described after “AA to BB” as the upper limit.
  • An organic EL device comprises an organic layer between both electrodes of an anode and a cathode.
  • This organic layer includes at least one layer composed of an organic compound.
  • this organic layer is formed by laminating a plurality of layers composed of an organic compound.
  • the organic layer may further contain an inorganic compound.
  • at least one layer of the organic layers is a light-emitting layer. Therefore, the organic layer may be composed of, for example, one light-emitting layer, or may include layers that can be employed in an organic EL device.
  • the layer that can be employed in the organic EL device is not particularly limited, but for example, at least one selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer. layer.
  • the organic EL element of this embodiment has an anode, a cathode, and a light-emitting layer included between the anode and the cathode, and the light-emitting layer is represented by the following general formula (1): Contains one compound.
  • the first compound represented by the general formula (1) below is a polycyclic heterocyclic compound having two imidazole rings in the molecule. Two imidazole rings in the molecule are bonded to both sides of the boron atom-containing heterocyclic ring and to ring A and ring C, respectively, as shown in the following general formula (1).
  • the present inventors have found that by including the first compound having such a structure in the light-emitting layer, the life of the device can be extended as compared with the case where the conventional polycyclic heterocyclic compound is included in the light-emitting layer. I found what I could do.
  • the first compound By having two imidazole rings, the first compound has an increased Af value compared to the case of having one imidazole ring. As a result, the effect of trapping electrons is increased, so that the electron load on the interface between the hole transport zone (for example, the hole transport layer) and the light emitting layer is reduced, and the life of the device is significantly improved. Since the first compound has an imidazole ring, the Af value increases as compared with the case of having an indole ring. As a result, the effect of trapping electrons is increased, so that the electron load on the interface between the hole transport zone (for example, the hole transport layer) and the light emitting layer is reduced, and the life of the device is significantly improved.
  • the first compound has an increased Af value compared to the compound represented by the following general formula (X1) and the compound represented by the following general formula (X2).
  • the effect of trapping electrons is increased, so that the electron load on the interface between the hole transport zone (for example, the hole transport layer) and the light emitting layer is reduced, and the life of the device is significantly improved.
  • the compound represented by the following general formula (X1) since the compound represented by the following general formula (X1) has two imidazole partial structures in the molecule, it may have the effect of increasing the Af value as described above.
  • the maximum peak wavelength of the spectrum shifts significantly to the short wavelength side. Therefore, for example, when used as a blue light emitting material, it is difficult to obtain an appropriate wavelength. .
  • n, p, ring A, ring C, R A and R C are each independently n, p, ring A and ring C in the following general formula (1) , R A and R C , each R X independently has the same definition as R 1 in the following general formula (1), and when a plurality of R X are present, the plurality of R X are the same as each other or different.
  • the organic EL device according to this embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when the device is driven. More preferably, the organic EL device according to the present embodiment emits light having a maximum peak wavelength of 430 nm or more and 480 nm or less when the device is driven.
  • the measurement of the maximum peak wavelength of the light emitted by the organic EL element when the element is driven is performed as follows. A spectral radiance spectrum is measured by a spectral radiance meter CS-2000 (manufactured by Konica Minolta Co., Ltd.) when a voltage is applied to the organic EL element so that the current density is 10 mA/cm 2 . In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).
  • the light emitting layer contains a first compound represented by the following general formula (1).
  • the first compound is preferably a compound (dopant material) that emits light having a maximum peak wavelength of 500 nm or less.
  • the first compound is more preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less.
  • the light-emitting layer preferably does not contain a metal complex.
  • the light-emitting layer preferably does not contain a phosphorescent material (phosphorescent dopant material).
  • the light emitting layer preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex.
  • heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
  • a method for measuring the maximum peak wavelength of a compound is as follows. A 5 ⁇ mol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300K). The emission spectrum can be measured with a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the maximum peak wavelength. In this specification, the maximum peak wavelength of fluorescence emission may be referred to as fluorescence emission maximum peak wavelength (FL-peak).
  • the peak with the maximum emission intensity is the maximum peak and the height of the maximum peak is 1, the height of other peaks appearing in the emission spectrum is less than 0.6 is preferably In addition, let the peak in an emission spectrum be a maximum value. Moreover, it is preferable that the number of peaks in the emission spectrum of the first compound is less than three.
  • the first compound is represented by the following general formula (1).
  • the substituent R AX , the substituent R BX and the substituent R CX are each independently halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted fluorocycloalkyl group having 1 to 50 ring carbon atoms, a group represented
  • the heterocyclic ring includes, for example, a ring structure (heterocyclic ring) obtained by removing the bond from the "heterocyclic group” exemplified in the above “substituent described herein”. These heterocycles may have a substituent or may be unsubstituted.
  • the aryl ring includes, for example, a ring structure (aryl ring) obtained by removing the bond from the "aryl group” exemplified in the above "substituent described herein”. These aryl rings may have a substituent or may be unsubstituted.
  • the first compound is preferably a compound represented by the following general formula (11), (12) or (13) below.
  • R 1 and R 2 are each independently synonymous with R 1 and R 2 in the general formula (1);
  • X 1 to X 3 are each independently CR B or a nitrogen atom;
  • X 4 to X 6 are each independently CR C or a nitrogen atom,
  • X 7 to X 9 are each independently CR A or a nitrogen atom,
  • Y 1 is CR C or a nitrogen atom;
  • Y 2 is an oxygen atom, a sulfur atom , CRCRC or NRC
  • Y 3 is CR A or a nitrogen atom,
  • Y 4 is an oxygen atom, a sulfur atom, CRA R A or NR A ;
  • R A has the same definition as R A in the general formula (1);
  • RB has the same definition as RB in the general formula (1);
  • R C has the same definition as R C in the general formula (1);
  • Y 2 is CRCRC , the two RCs in CRCRC are the same or different from each other;
  • R 1 , R 2 , R A , R B and R C that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently , hydrogen atom, halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a 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 cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —O—(R 81 ), a group represented by —N(R 82 )(R 83 ), a group represented by -S-(R 84 ), a group
  • the first compound is preferably a compound represented by the following general formula (11A), (12A) or (13A).
  • R 1 is R 11 ; combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubstituted fused ring, or not combined with each other
  • R 2 is R 13 ; combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubstituted fused ring, or not combined with each other, one or more sets of two or more adjacent ones of R 11 to R 13 are combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubstituted fused ring, or not combined with each other, one or more sets of two or more adjacent ones of R 14 to R 16 are combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form
  • R A in Y 4 are each independently hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 18 ring atoms, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a group represented by —O—(R 81 ), a group represented by —N(R 82 )(R 83 ), a group represented by -S-(R 84 ), a group represented by -B(R 96 )(R 97 ), or -CN, R 81 to R 84 and R 96 to R 97 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, It is a substituted or unsubstituted heterocyclic group having 3 to 18
  • the first compound is also preferably a compound represented by the following general formula (14A), (15A) or (16A).
  • R 1 , R 2 and R 11 to R 19 are each independently synonymous with R 1 , R 2 and R 11 to R 19 in general formula (11A). is.
  • the first compound is preferably a compound represented by the following general formula (11B), (12B) or (13B).
  • R 14 to R 19 each independently have the same meaning as R 14 to R 19 in the general formula (11); Y 2 , Y 4 , R 21 and R 23 are each independently synonymous with Y 2 , Y 4 , R 21 and R 23 in the general formula (12); R 11 is either R 31 or R 35 ; combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubstituted fused ring, or not combined with each other, R 13 is either R 41 or R 45 ; combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubstituted fused ring, or not combined with each other, one or more sets of two or more adjacent ones of R 11 to R 13 are combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each
  • R 1 , R 2 , R 11 to R 19 , R 21 , R 23 and Y which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring R C in 2 ,
  • R A in Y 4 , R 31 to R 35 and R 41 to R 45 are each independently hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 18 ring atoms, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a group represented by —Si(R 86 )(R 87 )(R 88 ), or —CN;
  • R 86 to R 88 are each independently A substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted hetero
  • the substituted or unsubstituted monocyclic ring is not formed, and the substituted or unsubstituted R 1 , R 2 , R A , R B , R C , R 11 to R 19 , R 21 , R 23 , R 31 to R 35 and R 41 to R 45 that do not form a substituted condensed ring are each independently , hydrogen atom, -CN, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 18 ring atoms, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, or a group represented by —Si(R 86 )(R 87 )(R 88 ) is preferred, hydrogen atom, -CN, a substituted or unsubstituted
  • R 1 is bonded to one or more selected from the group consisting of RB to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted It is also preferred to form fused rings.
  • R 2 is bonded to one or more selected from the group consisting of RB to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted It is also preferred to form fused rings.
  • ring B is a substituted or unsubstituted benzene ring
  • R 2 is a substituted or unsubstituted phenyl group
  • the phenyl group and RB are bonded to each other to form a monocyclic ring.
  • the compound include compounds represented by the following general formula (C1).
  • one or more sets of two or more adjacent substituents R AX among the two or more substituents are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted condensed ring.
  • the first compound when the ring A is a substituted or unsubstituted benzene ring, and two adjacent substituents R AX are combined to form a monocyclic ring, the first compound may be represented by the following general formula (C12 ) can be mentioned. Further, for example, when the ring A is a substituted or unsubstituted benzene ring, and a group consisting of two adjacent substituents R AX are bonded to each other to form a condensed ring, the first compound has the following general formula Examples include compounds represented by (C5) to (C10) and (C13) to (C14).
  • one or more sets of two or more adjacent substituents R BX among the two or more substituents RBX are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted condensed ring.
  • the first compound may be represented by the following general formula (C11 ) can be mentioned.
  • the first compound one or more sets of adjacent two or more of the two or more substituents R CX are bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted condensed ring.
  • the first compound may be represented by the following general formula (C2 ), (C3), (C7), (C8) and (C12).
  • the first compound has the following general formula Examples include compounds represented by (C4), (C9), (C10) and (C14).
  • the single ring or condensed ring mode is not limited to the modes represented by the following general formulas (C1) to (C14).
  • the first compound is also preferably a compound represented by any one of the following general formulas (C1) to (C14).
  • R 1 , R 2 , R A , R B and R C are each independently R 1 , R 2 , R A , R is synonymous with B and R C ;
  • R D each independently has the same definition as R 1 in the general formula (1), and when there are a plurality of R D , the plurality of R D are the same or different, and X D is an oxygen atom , sulfur atom , CRDRD or NRD , and XD is CRDRD , the two RDs in CRDRD are the same or different from each other.
  • the first compound can be produced by a known method.
  • the first compound can also be produced by imitating a known method and using known alternative reactions and raw materials that match the desired product.
  • Specific examples of the first compound include the following compounds. However, the present invention is not limited to these specific examples of the first compound.
  • D represents a deuterium atom and Me represents a methyl group in specific examples of compounds.
  • the light-emitting layer preferably contains a first host material and a first compound (a compound represented by the general formula (1)) as a first dopant material.
  • the first host material include 1) condensed aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, benzanthracene derivatives, fluorene derivatives, fluoranthene derivatives, and chrysene derivatives; Heterocyclic compounds such as thiophene derivatives and benzoxanthene derivatives can be mentioned.
  • the first host material is preferably a condensed aromatic compound, more preferably an anthracene derivative or a pyrene derivative (a compound represented by the general formula (100) described later), and preferably an anthracene derivative. More preferred.
  • the first host material is also preferably a benzanthracene derivative (compound represented by general formula (1X) described below) or a benzoxanthene derivative (compound represented by general formula (14X) described below).
  • a "host material” is, for example, a material contained in "50% by mass or more of the layer". Accordingly, the light-emitting layer contains, for example, 50% by weight or more of the total weight of the light-emitting layer of the first host material.
  • the first host material is an anthracene derivative
  • the first host material is preferably a compound represented by the following general formula (2).
  • R 201 to R 208 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, - a group represented by Si(R 901 ) (R 902 ) (R 903 ); a group represented by —O—(R 904 ), a group represented by -S-(R 905 ), a group represented by —N(R 906 )(R 907 ); a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
  • the multiple R 904 are present, the multiple R 904 are the same or different
  • At least one of R 201 to R 208 in the compound represented by the general formula (2) is preferably not a hydrogen atom. That is, when the first host material is the compound represented by the general formula (2), the compound represented by the general formula (2) is a trisubstituted anthracene derivative substituted with at least three substituents. Preferably.
  • R 201 to R 208 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, - a group represented by Si(R 901 ) (R 902 ) (R 903 ); a group represented by —O—(R 904 ), a group represented by -S-(R 905 ), a group represented by —N(R 906 )(R 907 ); a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsub
  • L 201 and L 202 are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms
  • Ar 201 and Ar 202 are each independently preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
  • Ar 201 and Ar 202 are each independently phenyl group, naphthyl group, a phenanthryl group, biphenyl group, a terphenyl group, a diphenylfluorenyl group, dimethylfluorenyl group, a benzodiphenyl fluorenyl group, benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, A naphthobenzofuranyl group or a naphthobenzothienyl group is preferred.
  • the compound represented by the general formula (2) is represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208) or general formula (209).
  • L 201 and Ar 201 are synonymous with L 201 and Ar 201 in the general formula (2)
  • R 201 to R 208 are each independently synonymous with R 201 to R 208 in the general formula (2).
  • the compound represented by the general formula (2) has the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), A compound represented by general formula (227), general formula (228) or general formula (229) is also preferred.
  • R 201 and R 203 to R 208 are each independently synonymous with R 201 and R 203 to R 208 in the general formula (2);
  • L 201 and Ar 201 are respectively synonymous with L 201 and Ar 201 in the general formula (2),
  • L 203 has the same definition as L 201 in the general formula (2),
  • L 203 and L 201 are the same or different from each other,
  • Ar 203 has the same definition as Ar 201 in the general formula (2), Ar 203 and Ar 201 are the same or different from each other.
  • the compound represented by the general formula (2) has the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), Compounds represented by general formula (247), general formula (248) or general formula (249) are also preferred.
  • R 201 , R 202 and R 204 to R 208 are each independently synonymous with R 201 , R 202 and R 204 to R 208 in the general formula (2);
  • L 201 and Ar 201 are respectively synonymous with L 201 and Ar 201 in the general formula (2),
  • L 203 has the same definition as L 201 in the general formula (2),
  • L 203 and L 201 are the same or different from each other,
  • Ar 203 has the same definition as Ar 201 in the general formula (2), Ar 203 and Ar 201 are the same or different from each other.
  • R 201 to R 208 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 or a group represented by —Si(R 901 ) (R 902 ) (R 903 ) is preferred.
  • L 201 is a single bond or an unsubstituted arylene group having 6 to 22 ring carbon atoms
  • Ar 201 is preferably a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.
  • the substituent of the anthracene skeleton in the compound represented by the general formula (2) Certain R 201 to R 208 are preferably hydrogen atoms from the viewpoint of preventing intermolecular interaction from being suppressed and suppressing a decrease in electron mobility, but R 201 to R 208 are substituted or It may be an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • the organic EL element according to the second embodiment may have an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order.
  • the order of the second light-emitting layers can also be reversed.
  • the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the second light-emitting layer and the first light-emitting layer from the anode side.
  • the first host material contained in the first light-emitting layer is the compound represented by the general formula (2), the following phenomenon may occur.
  • R 201 to R 208 in general formula (2) are preferably not bulky substituents.
  • R 201 to R 208 are bulky substituents such as alkyl groups and cycloalkyl groups, the interaction between molecules is suppressed, and the electron mobility with respect to the second host material decreases, and there is a risk that the relationship ⁇ e(H1)> ⁇ e(H2) described in the later-described formula (Equation 3) will not be satisfied.
  • the compound represented by the general formula (2) is used as the first host material in the first light-emitting layer, the second light-emitting layer satisfies the relationship ⁇ e(H1)> ⁇ e(H2).
  • the substituents in the case of "substituted or unsubstituted” in R 201 to R 208 are the aforementioned substituents that may be bulky, particularly substituted or unsubstituted alkyl groups, and substituted Alternatively, it is also preferable not to contain an unsubstituted cycloalkyl group.
  • the substituent in the case of "substituted or unsubstituted” in R 201 to R 208 does not include a substituted or unsubstituted alkyl group and a substituted or unsubstituted cycloalkyl group, so that an alkyl group, a cycloalkyl group, etc.
  • R 201 to R 208 as substituents of the anthracene skeleton are not bulky substituents, and R 201 to R 208 are unsubstituted. Further, in the case where R 201 to R 208 which are substituents of the anthracene skeleton are not bulky substituents, when a substituent is bonded to R 201 to R 208 as a non-bulky substituent, the substituent is also bulky.
  • the compound represented by general formula (2) can be produced by a known method.
  • Specific examples of compounds represented by formula (2) include the following compounds. However, the compound represented by general formula (2) is not limited to the specific examples below.
  • the first host material and the first dopant material preferably satisfy the relationship of the following formula (number A), and more preferably satisfy the following formula (number A1): More preferably, it satisfies the following formula (number A2).
  • Af(D1)-Af(H1) ⁇ 0.40 eV severe A
  • Af(D1)-Af(H1) ⁇ 0.45 eV number A1
  • Af(D1)-Af(H1) ⁇ 0.50 eV number A2
  • Af (H1) is the affinity (unit: eV) of the first host material
  • Af (D1) is the first host It is the affinity of the material (unit: eV).
  • the effect of trapping electrons is increased. reduces the electronic load on the interface. As a result, the device can have a longer life.
  • the affinity Af of a compound can be calculated from the redox potential of each compound determined by various electrochemical measurements. Af, Djulovich, Mayo, Forrest, Thompson, Organic Electronics, 10 (2009) p. 515-520, the first reduction potential (Ere [V]) of the compound measured in dimethylformamide (DMF) solvent and the first oxidation potential of ferrocene similarly measured as an internal standard ( Efc[V]), it can be calculated by the following formula (number C).
  • the redox potential can be measured by techniques such as cyclic voltammetry (CV) and differential pulse voltammetry (DPV).
  • CV cyclic voltammetry
  • DPV differential pulse voltammetry
  • the redox potential of each compound is measured by DPV measurement.
  • a specific measuring method is as described in Examples.
  • the light-emitting layer preferably contains the first dopant material as the first compound in an amount of 0.5% by mass or more of the total mass of the light-emitting layer. It is more preferable to contain more than 1.1% by mass of the mass, more preferably 1.2% by mass or more of the total mass of the light-emitting layer, and more preferably 1.5% by mass or more of the total mass of the light-emitting layer. more preferably.
  • the light-emitting layer preferably contains the first dopant material in an amount of 10% by weight or less of the total weight of the light-emitting layer, more preferably 7% by weight or less of the total weight of the light-emitting layer. It is more preferable to contain 5% by mass or less of the mass.
  • the light-emitting layer preferably contains the first host material in an amount of 60% by mass or more of the total weight of the light-emitting layer, and 70% by weight or more of the total weight of the light-emitting layer. more preferably 80% by mass or more of the total mass of the light-emitting layer, more preferably 90% by mass or more of the total mass of the light-emitting layer, and even more preferably 95% by mass of the total mass of the light-emitting layer It is even more preferable to contain at least 1% by mass.
  • the light-emitting layer preferably contains the first host material in an amount of 99% by weight or less of the total weight of the light-emitting layer. However, when the light-emitting layer contains the first host material and the first dopant material, the upper limit of the total content of the first host material and the first dopant material is 100% by mass.
  • the light-emitting layer contains materials other than the first host material and the first dopant material.
  • the light-emitting layer may contain only one type of the first host material, or may contain two or more types.
  • the light-emitting layer may contain only one kind of the first dopant material, or may contain two or more kinds thereof.
  • the film thickness of the light-emitting layer in the organic EL device of the present embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and most preferably 10 nm or more and 50 nm or less.
  • it is 5 nm or more, formation of a light-emitting layer and adjustment of chromaticity are likely to be facilitated, and when it is 50 nm or less, an increase in driving voltage is likely to be suppressed.
  • the organic EL device according to this embodiment may have two or more light-emitting layers.
  • the organic EL device according to this embodiment may have one or more organic layers in addition to the light-emitting layer.
  • Examples of the organic layer include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron blocking layer.
  • the organic EL device may be composed only of a light-emitting layer, but for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron blocking layer. It may further have at least one layer selected from the group consisting of
  • FIG. 1 shows a schematic configuration of an example of the organic EL element in this embodiment.
  • the organic EL element 1 includes a translucent substrate 2 , an anode 3 , a cathode 4 , and an organic layer 10 arranged between the anode 3 and the cathode 4 .
  • the organic layer 10 is configured by stacking a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side.
  • the present invention is not limited to the organic EL element having the configuration shown in FIG.
  • the light-emitting layers include a first light-emitting layer and a second light-emitting layer.
  • the first light-emitting layer includes a first host material and a first dopant material.
  • the second light-emitting layer includes a second host material and a second dopant material.
  • the first host material and the second host material are different from each other.
  • the first dopant material and the second dopant material are the same or different from each other.
  • the organic EL device according to the second embodiment has at least two light-emitting layers (first light-emitting layer and second light-emitting layer).
  • the first light-emitting layer according to the second embodiment has the same configuration as the light-emitting layer according to the first embodiment. In the following, differences from the first embodiment will be mainly described, and overlapping descriptions will be omitted or simplified.
  • the organic EL device according to the second embodiment can have a longer life and an improved luminous efficiency by using Triplet-Tripret-Annhilation (sometimes referred to as TTA).
  • TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. Note that the TTA mechanism may also be referred to as the TTF mechanism as described in WO2010/134350.
  • triplet excitons (hereinafter referred to as 3 A * ) increases, the triplet excitons collide with each other and a reaction occurs as shown in the following formula.
  • 1 A represents the ground state and 1 A * represents the lowest excited singlet exciton.
  • the TTF-derived emission ratio (TTF ratio) in the total emission intensity is 15/40, that is, 37.5%.
  • TTF ratio the TTF-derived emission ratio in the total emission intensity.
  • the initially generated triplet excitons collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons)
  • the triplet energy T 1 (H1) of the first host material and the triplet energy T 1 (H2) of the second host material preferably satisfies the relationship of the following formula (expression 1), and more preferably satisfies the relationship of the following expression (expression 2).
  • the triplet excitons generated by the recombination of holes and electrons in the second light-emitting layer by satisfying the relationship of the formula (Equation 1) are Even if carriers are excessively present at the interface between the second light-emitting layer and the organic layer that is in direct contact with the organic layer, triplet excitons present at the interface between the second light-emitting layer and the organic layer are considered to be less likely to be quenched. . Quenching by excess electrons is possible, for example, if a recombination zone exists locally at the interface between the second light-emitting layer and the hole-transporting layer or the electron-blocking layer.
  • the organic EL device according to the second embodiment is provided with a first light-emitting layer and a second light-emitting layer so as to satisfy the relationship of the formula (Equation 1), so that triplet excitation generated in the second light-emitting layer The electrons migrate to the first emission layer without being quenched by excess carriers, and can be inhibited from migrating back from the first emission layer to the second emission layer.
  • the organic EL device has a second light-emitting layer that mainly generates triplet excitons, and a second light-emitting layer that mainly expresses the TTF mechanism by utilizing the triplet excitons that have moved from the second light-emitting layer. and one light-emitting layer as different regions, using a compound having a lower triplet energy than the second host material in the second light-emitting layer as the first host material in the first light-emitting layer , the luminous efficiency is improved by providing a difference in triplet energy.
  • the organic EL device according to the second embodiment selects a combination of host materials that satisfy the relationship of the formula (Formula 1), and the first light-emitting layer is the first compound according to the first embodiment (the general formula By containing the compound represented by (1), the life of the device can be extended and the luminous efficiency can be improved.
  • the organic EL device according to the second embodiment preferably emits light with a maximum peak wavelength of 500 nm or less, more preferably 420 nm or more and 480 nm or less, when the device is driven.
  • the measurement of the maximum peak wavelength of the light emitted by the organic EL element when the element is driven is as described above.
  • the first light-emitting layer includes a first host material and a first dopant material.
  • the first host material is a compound different from the second host material contained in the second light-emitting layer.
  • the first light-emitting layer according to the second embodiment has the same configuration as the light-emitting layer according to the first embodiment. Therefore, the same material as the first host material described in the first embodiment can be used as the first host material contained in the first light-emitting layer.
  • the same material as the first dopant material (first compound) described in the first embodiment can be used as the first dopant material (first compound) described in the first embodiment.
  • the first light-emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the device is driven.
  • the maximum peak wavelength of light emitted from the light-emitting layer when the device is driven can be measured by the method described below.
  • ⁇ Maximum peak wavelength ⁇ p of light emitted from the light-emitting layer when the device is driven is obtained by fabricating an organic EL device using the same material as the first light-emitting layer for the second light-emitting layer, and measuring the current of the organic EL device.
  • a spectral radiance spectrum is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage is applied to the element so that the density becomes 10 mA/cm 2 .
  • the maximum peak wavelength ⁇ p 1 (unit: nm) is calculated from the obtained spectral radiance spectrum.
  • the maximum peak wavelength ⁇ p2 of light emitted from the second light-emitting layer when the device is driven is obtained by fabricating an organic EL device using the same material as the second light-emitting layer for the first light-emitting layer, and measuring the current of the organic EL device.
  • a spectral radiance spectrum is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage is applied to the element so that the density becomes 10 mA/cm 2 .
  • the maximum peak wavelength ⁇ p 2 (unit: nm) is calculated from the obtained spectral radiance spectrum.
  • the maximum peak half width FWHM of the first dopant material is 1 nm or more and 20 nm or less.
  • the Stokes shift of the first dopant material preferably exceeds 7 nm. If the Stokes shift of the first dopant material exceeds 7 nm, it becomes easier to prevent a decrease in luminous efficiency due to self-absorption. Self-absorption is a phenomenon in which emitted light is absorbed by the same compound, and is a phenomenon that causes a decrease in luminous efficiency. Self-absorption is conspicuously observed in compounds with a small Stokes shift (i.e., a large overlap between the absorption spectrum and the fluorescence spectrum). is small) is preferably used. The Stokes shift can be measured by the method described below.
  • a compound to be measured is dissolved in toluene at a concentration of 2.0 ⁇ 10 ⁇ 5 mol/L to prepare a sample for measurement.
  • a measurement sample placed in a quartz cell is irradiated with continuous light in the ultraviolet-visible region at room temperature (300K), and an absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured.
  • a spectrophotometer can be used for the absorption spectrum measurement, for example, spectrophotometer U-3900/3900H manufactured by Hitachi High-Tech Science Co., Ltd. can be used.
  • a compound to be measured is dissolved in toluene at a concentration of 4.9 ⁇ 10 ⁇ 6 mol/L to prepare a sample for measurement.
  • a measurement sample placed in a quartz cell was irradiated with excitation light at room temperature (300 K), and fluorescence spectra (vertical axis: fluorescence intensity, horizontal axis: wavelength) were measured.
  • a spectrophotometer can be used for fluorescence spectrum measurement, for example, spectrofluorophotometer F-7000 manufactured by Hitachi High-Tech Science Co., Ltd. can be used. From these absorption spectra and fluorescence spectra, the difference between the maximum absorption wavelength and the maximum fluorescence wavelength is calculated to determine the Stokes shift (SS).
  • the unit of Stokes shift SS is nm.
  • the triplet energy T 1 (D1) of the first dopant material and the triplet energy T 1 (H1) of the first host material are represented by the following formula (Formula 4A ) is preferably satisfied.
  • the first dopant material and the first host material satisfy the relationship of the formula (Equation 4A), thereby generating triplet excitation in the second light-emitting layer
  • the electrons transfer to the first light-emitting layer, they energy transfer to molecules of the first host material rather than to the first dopant material, which has a higher triplet energy.
  • triplet excitons generated by recombination of holes and electrons on the first host material do not move to the first dopant material having higher triplet energy.
  • Triplet excitons generated by recombination on the molecules of the first dopant material quickly transfer energy to the molecules of the first host material.
  • Triplet excitons of the first host material do not move to the first dopant material, and triplet excitons on the first host material collide efficiently by the TTF phenomenon to generate singlet excitons. is generated.
  • the singlet energy S 1 (H1) of the first host material and the singlet energy S 1 (D1) of the first dopant material are obtained by the following formula (Equation 4 ) is preferably satisfied.
  • the singlet energy of the first dopant material is Since the singlet energy is smaller than that of the first host material, the singlet excitons generated by the TTF phenomenon transfer energy from the first host material to the first dopant material, causing the first dopant material to emit light (preferably contributes to fluorescence emission).
  • a tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. Among the maximum values of the absorption spectrum, consider the tangent line at each point on the curve when moving from the maximum value on the longest wavelength side to the long wavelength direction on the spectrum curve. This tangent line repeats the slope decreasing and then increasing as the curve falls (that is, as the value on the vertical axis decreases). The tangent line drawn at the point where the slope value takes the minimum value on the long wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent line to the fall on the long wavelength side of the absorption spectrum. The maximum absorbance value of 0.2 or less is not included in the maximum value on the longest wavelength side.
  • the electron mobility ⁇ e (H2) of the second host material and the electron mobility ⁇ e (H1) of the first host material satisfy the relationship of the following formula (Equation 3).
  • the first host material and the second host material satisfy the relationship of the following formula (Equation 3)
  • the recombination ability of holes and electrons in the second light-emitting layer is improved.
  • the hole mobility ⁇ h(H2) of the second host material and the hole mobility ⁇ h(H1) of the first host material satisfy the relationship of the following formula (Equation 31). ⁇ h(H2)> ⁇ h(H1) (Equation 31)
  • the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the second light-emitting layer and the first light-emitting layer from the anode side
  • Electron mobility can be measured by the following method using impedance spectroscopy.
  • a layer to be measured having a thickness of 100 nm to 200 nm is sandwiched between the anode and the cathode, and a minute AC voltage of 100 mV or less is applied while applying a bias DC voltage.
  • the alternating current value (absolute value and phase) flowing at this time is measured.
  • the main measurement is performed while changing the frequency of the AC voltage, and the complex impedance (Z) is calculated from the current value and the voltage value.
  • Electron mobility (thickness of layer to be measured) 2 / (response time/voltage)
  • Hole mobility can be measured in the same manner as electron mobility using impedance spectroscopy.
  • the content of the first dopant material in the first light-emitting layer is in the same range as the content of the first dopant material described in the first embodiment. is preferred.
  • the content of the first host material in the first light-emitting layer is in the same range as the content of the first host material described in the first embodiment. is preferred.
  • the film thickness of the first light-emitting layer is preferably 5 nm or more, more preferably 15 nm or more. If the thickness of the first light-emitting layer is 5 nm or more, triplet excitons that have moved from the second light-emitting layer to the first light-emitting layer are likely to be prevented from returning to the second light-emitting layer. Moreover, when the film thickness of the first light-emitting layer is 5 nm or more, triplet excitons can be sufficiently separated from recombination sites in the second light-emitting layer.
  • the film thickness of the first light-emitting layer is preferably 20 nm or less. If the film thickness of the first light-emitting layer is 20 nm or less, the density of triplet excitons in the first light-emitting layer can be improved, and the TTF phenomenon can occur more easily. In the organic EL device according to the second embodiment, the film thickness of the first light-emitting layer is preferably 5 nm or more and 20 nm or less.
  • the second light-emitting layer includes a second host material and a second dopant material.
  • the second host material is a compound different from the first host material contained in the first light-emitting layer.
  • the second dopant material is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less.
  • the second dopant material is more preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less.
  • the method for measuring the maximum peak wavelength of the compound is as described above.
  • the second dopant material and the first dopant material are the same or different compounds.
  • the second light-emitting layer preferably does not contain a metal complex. Moreover, in the organic EL device according to this embodiment, it is also preferable that the first light-emitting layer does not contain a boron-containing complex.
  • the second emitting layer preferably does not contain a phosphorescent material (dopant material). Moreover, it is preferable that the second light-emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex.
  • the peak with the maximum emission intensity is the maximum peak and the height of the maximum peak is 1, the height of other peaks appearing in the emission spectrum is 0.6. It is preferably less than In addition, let the peak in an emission spectrum be a maximum value. Moreover, it is preferable that the number of peaks in the emission spectrum of the second light-emitting compound is less than three.
  • the second light-emitting layer preferably emits light with a maximum peak wavelength of 500 nm or less when the device is driven.
  • the second host material examples include 1) condensed aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, benzanthracene derivatives, fluorene derivatives, fluoranthene derivatives, and chrysene derivatives; Heterocyclic compounds such as thiophene derivatives and benzoxanthene derivatives can be mentioned.
  • the second host material is preferably a condensed aromatic compound, more preferably a pyrene derivative (compound represented by general formula (100) described below).
  • the second host material is also preferably a benzanthracene derivative (compound represented by general formula (1X) described below) or a benzoxanthene derivative (compound represented by general formula (14X) described below).
  • the second host material is a pyrene derivative
  • the second host material is preferably a compound represented by the following general formula (100).
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
  • the multiple R 901 are present, the multiple R 901 are the same or different from each other,
  • the multiple R 902 are present, the multiple R 902 are the same or different from each other,
  • multiple R 903 are present, the multiple R 903 are the same or different from each other,
  • multiple R 904 are present, the multiple R 904 are the same or different from each other, When multiple
  • the group represented by the general formula (110) is preferably a group represented by the following general formula (111).
  • X 1 is CR 123 R 124 , an oxygen atom, a sulfur atom, or NR 125 ;
  • L 111 and L 112 are each independently single bond, 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, ma is 0, 1, 2, 3 or 4; mb is 0, 1, 2, 3 or 4; ma+mb is 0, 1, 2, 3 or 4;
  • Ar 101 has the same definition as Ar 101 in the general formula (110),
  • R 121 , R 122 , R 123 , R 124 and R 125 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having
  • L 111 is bound, R 121 is bound to the remaining three positions of *1 to *4, L 112 is bound to any one position of *5 to *8, and the remaining positions of *5 to *8 are R122 is attached at three positions.
  • L 111 is bonded to the *2 carbon atom position in the ring structure represented by the general formula (111a), and L 112 is the general formula ( When it is bonded to the *7 carbon atom position in the ring structure represented by 111a), the group represented by the general formula (111) is represented by the following general formula (111b).
  • X 1 , L 111 , L 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124 and R 125 each independently represent X 1 , L 111 , L in the general formula (111) 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124 and R 125 ; the plurality of R 121 are the same or different from each other, A plurality of R 122 are the same or different from each other. )
  • the group represented by general formula (111) is preferably a group represented by general formula (111b).
  • ma is 0, 1 or 2;
  • mb is 0, 1 or 2.
  • ma is 0 or 1
  • mb is preferably 0 or 1.
  • Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
  • Ar 101 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, A substituted or unsubstituted phenanthryl group or a substituted or unsubstituted fluorenyl group is preferred.
  • Ar 101 is also preferably a group represented by the following general formula (120), general formula (130) or general formula (140).
  • R 111 to R 120 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, - a group represented by Si(R 901 ) (R 902 ) (R 903 ); a group represented by —O—(R 904 ), a group represented by -S-(R 905 ), a group represented by —N(R 906 )(R 907 ); a substituted or unsubstituted aralkyl
  • the second host material is preferably represented by the following general formula (101).
  • L 101 is A single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms is preferred.
  • the second host material is preferably represented by the following general formula (102).
  • R 101 to R 120 each independently have the same meaning as R 101 to R 120 in the general formula (101); provided that one of R 101 to R 110 represents the binding position to L 111 , one of R 111 to R 120 represents the binding position to L 112 , X 1 is CR 123 R 124 , an oxygen atom, a sulfur atom, or NR 125 ; L 111 and L 112 are each independently single bond, 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, ma is 0, 1, 2, 3 or 4; mb is 0, 1, 2, 3 or 4; ma+mb is 0, 1, 2, 3 or 4; R 121 , R 122 , R 123 , R 124 and R 125 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms
  • ma is 0, 1 or 2; mb is preferably 0, 1 or 2.
  • ma is 0 or 1
  • mb is preferably 0 or 1.
  • R 101 to R 110 are preferably groups represented by the general formula (110).
  • R 101 to R 110 are groups represented by the general formula (110), and Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. is preferred.
  • Ar 101 is not a substituted or unsubstituted pyrenyl group
  • L 101 is not a substituted or unsubstituted pyrenylene group
  • the substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms as R 101 to R 110 that is not a group represented by the general formula (110) is preferably not a substituted or unsubstituted pyrenyl group.
  • R 101 to R 110 which are not groups represented by the general formula (110) are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is preferred.
  • R 101 to R 110 which are not groups represented by the general formula (110) are each independently hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferred.
  • R 101 to R 110 which are not groups represented by the general formula (110) are preferably hydrogen atoms.
  • the compound represented by general formula (100) can be produced by a known method.
  • Specific examples of compounds represented by general formula (100) include the following compounds. However, the compound represented by general formula (100) is not limited to the specific examples below.
  • the second host material is a benzanthracene derivative
  • the second host material is preferably a compound represented by the following general formula (1X).
  • the group represented by the general formula (11X) is preferably a group represented by the following general formula (111X).
  • X 1 is CR 143 R 144 , an oxygen atom, a sulfur atom, or NR 145 ;
  • L 111 and L 112 are each independently single bond, 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, ma is 1, 2, 3 or 4;
  • mb is 1, 2, 3 or 4; ma+mb is 2, 3 or 4;
  • Ar 101 has the same definition as Ar 101 in the general formula (11X)
  • R 141 , R 142 , R 143 , R 144 and R 145 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to
  • L 111 is bonded to the *2 carbon atom position in the ring structure represented by the general formula (111aX)
  • L 112 is the general formula ( 111aX)
  • the group represented by the general formula (111X) is represented by the following general formula (111bX) when it is bonded to the *7 carbon atom position in the ring structure represented by the formula (111aX).
  • X 1 , L 111 , L 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145 each independently represent X 1 , L 111 , L in general formula (111X) 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145 ; the plurality of R 141 are the same or different from each other, The plurality of R 142 are the same or different from each other. )
  • the group represented by general formula (111X) is preferably a group represented by general formula (111bX).
  • ma is preferably 1 or 2
  • mb is preferably 1 or 2.
  • ma is preferably 1 and mb is preferably 1.
  • Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
  • Ar 101 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benz[a]anthryl group, a substituted or unsubstituted pyrenyl group, A substituted or unsubstituted phenanthryl group or a substituted or unsubstituted fluorenyl group is preferred.
  • the compound represented by the general formula (1X) is also preferably represented by the following general formula (101X).
  • R 111 and R 112 represents the binding position to L 101
  • one of R 133 and R 134 represents the binding position to L 101
  • R 133 or R 134 not at the bonding position with L 101 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, - a group represented by Si(R 901 ) (R 902 ) (R
  • L 101 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.
  • the compound represented by the general formula (1X) is also preferably represented by the following general formula (102X).
  • R 111 and R 112 represents the binding position to L 111
  • one of R 133 and R 134 represents the binding position to L 112
  • R 101 to R 110 , R 121 to R 130 , R 111 or R 112 which is not in the bonding position with L 111 and R 133 or R 134 which is not in the bonding position with L 112 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, - a group represented by Si(R 901 ) (R
  • ma in the general formula (102X) is preferably 1 or 2
  • mb is preferably 1 or 2.
  • ma is preferably 1 and mb is preferably 1 in the general formula (102X).
  • the group represented by the general formula (11X) is a group represented by the following general formula (11AX), or a group represented by the following general formula (11BX) It is also preferable that
  • R 121 to R 131 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, - a group represented by Si(R 901 ) (R 902 ) (R 903 ); a group represented by —O—(R 904 ), a group represented by -S-(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by -C(
  • the compound represented by the general formula (1X) is also preferably represented by the following general formula (103X).
  • R 101 to R 110 and R 112 are respectively synonymous with R 101 to R 110 and R 112 in the general formula (1X);
  • R 121 to R 131 , L 131 and L 132 have the same definitions as R 121 to R 131 , L 131 and L 132 in general formula (11BX) above.
  • L 131 is also preferably a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.
  • L 132 is also preferably a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.
  • R 101 to R 112 are also preferably groups represented by the general formula (11X).
  • R 101 to R 112 are groups represented by the general formula (11X), and Ar 101 in the general formula (11X) is , a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • Ar 101 is not a substituted or unsubstituted benz[a]anthryl group
  • L 101 is not a substituted or unsubstituted benz[a]anthrylene group
  • the substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms as R 101 to R 110 that is not a group represented by the general formula (11X) is not a substituted or unsubstituted benz[a]anthryl group. is also preferred.
  • each of R 101 to R 112 that is not a group represented by the general formula (11X) is independently a hydrogen atom or a substituted or unsubstituted group having 1 to 50 carbon atoms.
  • an alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted 5 to 50 ring atoms is preferably a heterocyclic group of
  • R 101 to R 112 which are not groups represented by the general formula (11X) are hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Alternatively, it is preferably a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.
  • R 101 to R 112 that are not groups represented by general formula (11X) are preferably hydrogen atoms.
  • the compound represented by general formula (1X) can be produced by a known method.
  • Specific examples of compounds represented by general formula (1X) include the following compounds. However, the compound represented by general formula (1X) is not limited to the specific examples below.
  • the second host material is a benzoxanthene derivative
  • the second host material is preferably a compound represented by the following general formula (14X).
  • the compound represented by general formula (14X) can be produced by a known method.
  • Specific examples of compounds represented by general formula (14X) include the following compounds. However, the compound represented by general formula (14X) is not limited to the specific examples below.
  • Examples of the second dopant material include the first compound represented by the general formula (1), a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, an aromatic group amine derivatives, tetracene derivatives and the like.
  • the second dopant material is preferably the first compound represented by the general formula (1), the compound represented by the following general formula (5), or the compound represented by the following general formula (6).
  • R 501 to R 507 and R 511 to R 517 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 carbon atoms, - a group represented by Si(R 901 ) (R 902 ) (R
  • R 521 and R 522 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 carbon atoms, - a group represented by Si(R 901 ) (R 902 ) (R 903 ); a group represented by —O—(R 904 ), a group represented by -S-(R 905 ), a group represented by —N(R 906 )(R 907 ); halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5
  • a set of adjacent two or more of R 501 to R 507 and R 511 to R 517 is, for example, a set of R 501 and R 502 , a set of R 502 and R 503 , R 503 and R 504 , R 505 and R 506 , R 506 and R 507 , R 501 , R 502 and R 503 , and so on.
  • At least one, preferably two of R 501 to R 507 and R 511 to R 517 are groups represented by —N(R 906 )(R 907 ).
  • R 501 -R 507 and R 511 -R 517 are each independently hydrogen atom, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • the compound represented by the general formula (5) is a compound represented by the following general formula (52).
  • R 531 to R 534 and R 541 to R 544 are combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubstituted fused ring, or not combined with each other
  • R 531 to R 534 , R 541 to R 544 , and R 551 and R 552 that do not form a single ring and do not form a condensed ring are each independently hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms
  • R 561 to R 564 are each independently A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring
  • the compound represented by the general formula (5) is a compound represented by the following general formula (53).
  • R 551 , R 552 and R 561 to R 564 are each independently synonymous with R 551 , R 552 and R 561 to R 564 in general formula (52).
  • R 561 to R 564 in the general formulas (52) and (53) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms (preferably a phenyl group ).
  • R 521 and R 522 in the general formula (5) and R 551 and R 552 in the general formulas (52) and (53) are hydrogen atoms.
  • the substituents in the case of "substituted or unsubstituted” in the general formulas (5), (52) and (53) are a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • the compound represented by general formula (5) can be produced by a known method.
  • Specific examples of compounds represented by formula (5) include the following compounds. However, the compound represented by general formula (5) is not limited to the specific examples below.
  • a ring, b ring and c 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
  • R 601 and R 602 each independently combine with the a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring
  • R 601 and R 602 that 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,
  • Rings a, b and c are rings (substituted or unsubstituted ring-forming carbon atoms of 6 to 50 or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms).
  • the "aromatic hydrocarbon ring" of the a ring, b ring and c ring has the same structure as the compound in which a hydrogen atom is introduced into the above "aryl group”.
  • the "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the central condensed two-ring structure of the general formula (6) as ring-forming atoms.
  • the "aromatic hydrocarbon rings” of rings b and c contain two carbon atoms on the central condensed two-ring structure of the general formula (6) as ring-forming atoms.
  • substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms include compounds in which a hydrogen atom is introduced into the "aryl group” described in Specific Example Group G1.
  • the “heterocyclic ring” of rings a, b and c has the same structure as the compound in which a hydrogen atom is introduced into the “heterocyclic group” described above.
  • the “heterocyclic ring” of the a ring contains three carbon atoms on the central condensed two-ring structure of the general formula (6) as ring-forming atoms.
  • heterocyclic rings of rings b and c contain two carbon atoms on the central condensed two-ring structure of the general formula (6) as ring-forming atoms.
  • Specific examples of the "substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms” include compounds in which a hydrogen atom is introduced into the "heterocyclic group" described in Specific Example Group G2.
  • R 601 and R 602 may each independently combine with ring a, ring b or ring c to form a substituted or unsubstituted heterocyclic ring.
  • the heterocyclic ring in this case contains a nitrogen atom on the central condensed two-ring structure of the general formula (6).
  • the heterocyclic ring in this case may contain heteroatoms other than the nitrogen atom.
  • the fact that R 601 and R 602 are bonded to the a ring, b ring, or c ring specifically means that the atoms constituting the a ring, b ring, or c ring are bonded to the atoms constituting R 601 and R 602 .
  • R 601 may combine with the a ring to form a two-ring (or three or more) condensed nitrogen-containing heterocyclic ring in which the ring containing R 601 and the a ring are fused.
  • Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to nitrogen-containing heterocyclic groups having two or more condensed rings among the specific example group G2. The same applies when R 601 is bonded to the b ring, when R 602 is bonded to the a ring, and when R 602 is bonded to the c ring.
  • the a-ring, b-ring and c-ring in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms. In one embodiment, the a-ring, b-ring and c-ring in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
  • R 601 and R 602 in the general formula (6) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, Preferred is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by the general formula (6) is a compound represented by the following general formula (62).
  • R 601A is combined with one or more selected from the group consisting of R 611 and R 621 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring;
  • R 602A combines with one or more selected from the group consisting of R 613 and R 614 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring;
  • R 601A and R 602A that 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
  • R 601A and R 602A in general formula (62) are groups corresponding to R 601 and R 602 in general formula (6), respectively.
  • R 601A and R 611 may combine to form a two-ring (or three or more) condensed nitrogen-containing heterocyclic ring in which a ring containing them and a benzene ring corresponding to ring a are fused.
  • Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to nitrogen-containing heterocyclic groups having two or more condensed rings among the specific example group G2. The same applies to the case where R 601A and R 621 are combined, the case where R 602A and R 613 are combined, and the case where R 602A and R 614 are combined.
  • R 611 to R 621 may be joined together to form a substituted or unsubstituted single ring, or may be joined together to form a substituted or unsubstituted fused ring.
  • R 611 and R 612 may combine 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 with respect to the 6-membered ring to which they are bonded,
  • the formed condensed ring is a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring or dibenzothiophene ring.
  • R 611 to R 621 that do not contribute to ring formation are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • R 611 to R 621 that do not contribute to ring formation are each independently hydrogen atom, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • R 611 to R 621 that do not contribute to ring formation are each independently It is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 611 to R 621 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, At least one of R 611 to R 621 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the general formula (62) is a compound represented by the following general formula (63).
  • R 631 is combined with R 646 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring
  • R 633 is combined with R 647 to form a substituted or unsubstituted heterocyclic ring or does not form a substituted or unsubstituted heterocyclic ring
  • R 634 is combined with R 651 to form a substituted or unsubstituted heterocyclic ring or does not form a substituted or unsubstituted heterocyclic ring
  • R 641 is combined with R 642 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring
  • one or more sets of adjacent two or more of R 631 to R 651 are combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubsti
  • R 631 may combine with R 646 to form a substituted or unsubstituted heterocyclic ring.
  • R 631 and R 646 are bonded to form a nitrogen-containing heterocyclic ring having three or more condensed rings, in which the benzene ring to which R 646 is bonded, the ring containing N, and the benzene ring corresponding to ring a are condensed.
  • the nitrogen-containing heterocyclic ring include compounds corresponding to nitrogen-containing heterocyclic groups having three or more condensed rings among specific example group G2. The same applies when R633 and R647 are bonded, when R634 and R651 are bonded, and when R641 and R642 are bonded.
  • R 631 to R 651 that do not contribute to ring formation are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • R 631 to R 651 that do not contribute to ring formation are each independently hydrogen atom, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • R 631 to R 651 that do not contribute to ring formation are each independently It is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 631 to R 651 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, At least one of R 631 to R 651 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63A).
  • R661 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, 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 662 to R 665 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
  • R 661 -R 665 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 661 to R 665 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63B).
  • R 671 and R 672 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 carbon atoms, a group represented by —N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms
  • R 673 to R 675 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
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63B').
  • R 672 to R 675 are each independently synonymous with R 672 to R 675 in general formula (63B).
  • At least one of R 671 -R 675 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
  • R672 is hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a group represented by —N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms
  • R 671 and R 673 to R 675 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a group represented by —N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63C).
  • R 681 and R 682 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 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 683 to R 686 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 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63C').
  • R 683 to R 686 are each independently synonymous with R 683 to R 686 in general formula (63C).
  • R 681 to R 686 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 681 to R 686 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • an intermediate is formed by connecting rings a, b and c with a linking group (a group containing NR 601 and a group containing NR 602 ).
  • the final product can be produced by producing (first reaction) and connecting the a-ring, b-ring and c-ring with a linking group (a group containing a boron atom) (second reaction).
  • first reaction an amination reaction such as the Bachbold-Hartwig reaction can be applied.
  • a tandem hetero Friedel-Crafts reaction or the like can be applied.
  • the compound represented by general formula (6) can be produced by a known method.
  • Specific examples of compounds represented by formula (6) include the following compounds. However, the compound represented by general formula (6) is not limited to the specific examples below.
  • the singlet energy S 1 (H2) of the second host material and the singlet energy S 1 (D2) of the second dopant material are represented by the following formula (Equation 20): It is preferable to satisfy the relationship. S 1 (H2)>S 1 (D2) (Equation 20)
  • the second host material and the second dopant material satisfy the relationship of the formula (Equation 20), so that the singlet excitons generated on the second host material are transferred from the second host material to the second energy transfer to the second dopant material, contributing to the emission (preferably fluorescent emission) of the second dopant material.
  • the triplet energy T 1 (H2) of the second host material and the triplet energy T 1 (D2) of the second dopant material are represented by the following formula (20A) It is preferable to satisfy the relationship. T 1 (D2)>T 1 (H2) (Equation 20A)
  • the second host material and the second dopant material satisfy the relationship of the formula (20A), so that the triplet excitons generated in the second light-emitting layer have a higher triplet energy than the second Since it migrates on the second host material and not on the dopant material of the second layer, it is easier to migrate to the first light-emitting layer.
  • the second light-emitting layer preferably contains the second dopant material in an amount of 0.5% by mass or more of the total mass of the second light-emitting layer. It is more preferable to contain more than 1.1% by weight of the total weight of the light-emitting layer, more preferably 1.2% by weight or more of the total weight of the second light-emitting layer, and the total weight of the second light-emitting layer It is more preferable to contain 1.5% by mass or more of the mass.
  • the second light-emitting layer preferably contains the second dopant material in an amount of 10% by weight or less of the total weight of the second light-emitting layer, and 7% by weight or less of the total weight of the second light-emitting layer. More preferably, it is contained in an amount of 5% by mass or less of the total mass of the second light-emitting layer.
  • the second light-emitting layer preferably contains the second host material in an amount of 60% by mass or more of the total mass of the second light-emitting layer. 70% by mass or more of the total mass of the second light-emitting layer, more preferably 80% by mass or more of the total mass of the second light-emitting layer, more preferably 90% by mass or more of the total mass of the second light-emitting layer , and more preferably 95% by mass or more of the total mass of the second light-emitting layer.
  • the second light-emitting layer preferably contains the second host material in an amount of 99% by mass or less based on the total mass of the second light-emitting layer.
  • the second emitting layer contains the second host material and the second dopant material
  • the upper limit of the total content of the second host material and the second dopant material is 100% by mass.
  • the second embodiment does not exclude that the first emitting layer contains materials other than the second host material and the second dopant material.
  • the second light-emitting layer may contain only one type of the second host material, or may contain two or more types.
  • the second light-emitting layer may contain only one type of the second dopant material, or may contain two or more types.
  • the film thickness of the second light-emitting layer is preferably 3 nm or more, more preferably 5 nm or more. When the film thickness of the second light-emitting layer is 3 nm or more, the film thickness is sufficient to cause recombination of holes and electrons in the second light-emitting layer. In the organic EL device according to the second embodiment, the film thickness of the second light-emitting layer is preferably 15 nm or less, more preferably 10 nm or less. If the film thickness of the second light-emitting layer is 15 nm or less, the film thickness is sufficiently thin for triplet excitons to move to the first light-emitting layer. In the organic EL device according to the second embodiment, the film thickness of the second light-emitting layer is more preferably 3 nm or more and 15 nm or less.
  • the organic EL device according to the second embodiment may have one or more organic layers in addition to the first light-emitting layer and the second light-emitting layer.
  • the organic layer include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron blocking layer. be done.
  • the organic EL device may have, for example, an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order.
  • the order of the first light-emitting layer can be reversed to have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in that order.
  • a combination of host materials that satisfies the relationship of the formula (Equation 1) is selected, and the first light-emitting layer is the first light-emitting layer according to the first embodiment.
  • the organic EL device according to the second embodiment may be composed of only the first light-emitting layer and the second light-emitting layer, but for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport It may further have at least one layer selected from the group consisting of a layer, a hole blocking layer, an electron blocking layer, and the like.
  • the organic EL device according to the second embodiment includes the first light-emitting layer between the anode and the cathode, and the second light-emitting layer between the first light-emitting layer and the anode. is preferred.
  • the organic EL device according to this embodiment includes the first light-emitting layer between the anode and the cathode, and the second light-emitting layer between the first light-emitting layer and the cathode. is also preferred.
  • the organic EL device according to the second embodiment preferably includes a hole transport layer between the light emitting layer and the anode.
  • the organic EL device according to the second embodiment preferably includes an electron transport layer between the light emitting layer and the cathode.
  • FIG. 2 shows a schematic configuration of an example of the organic EL device according to the second embodiment.
  • the organic EL element 1A includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A arranged between the anode 3 and the cathode 4.
  • FIG. The organic layer 10A includes, in order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, a second light emitting layer 52, a first light emitting layer 51, an electron transport layer 8, and an electron injection layer 9. It is constructed by being laminated in order.
  • FIG. 3 shows a schematic configuration of another example of the organic EL element according to the second embodiment.
  • the organic EL element 1B includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10B arranged between the anode 3 and the cathode 4.
  • FIG. The organic layer 10B includes, in order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, a first light emitting layer 51, a second light emitting layer 52, an electron transport layer 8, and an electron injection layer 9. It is constructed by being laminated in order.
  • the present invention is not limited to the configurations of the organic EL elements shown in FIGS.
  • the organic EL device may further include a third light-emitting layer.
  • the third light-emitting layer comprises a third host material, wherein the first host material, the second host material and the third host material are different from each other, and the third light-emitting layer comprises the third dopant material. wherein the first dopant material, the second dopant material, and the third dopant material are the same or different from each other, and the triplet energy T 1 (H2) of the second host material and The triplet energy T 1 (H3) of the third host material preferably satisfies the relationship of the following formula (Equation 5). T 1 (H2)>T 1 (H3) (Equation 5)
  • the third dopant material is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less, more preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less.
  • the triplet energy T 1 (H1) of the first host material and the triplet energy T 1 (H3) of the third host material preferably satisfies the relationship of the following formula (Equation 6).
  • the third host material is not particularly limited, for example, the host materials exemplified as the first host material and the second host material in the above embodiments can be used.
  • the third dopant material is not particularly limited, for example, the dopant materials exemplified as the first dopant material and the second dopant material in the above embodiments can be used.
  • the first light-emitting layer and the second light-emitting layer are in direct contact with each other.
  • the layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact” is, for example, any of the following aspects (LS1), (LS2) and (LS3) Aspects can also be included.
  • (LS1) A region in which both the first host material and the second host material are mixed in the process of vapor-depositing the compound for the first light-emitting layer and the step for vapor-depositing the compound for the second light-emitting layer occurs and the region is present at the interface between the first and second light-emitting layers.
  • the step of vapor-depositing the compound for the first light-emitting layer and the deposition of the compound for the second light-emitting layer A region in which the first host material, the second host material, and the light-emitting compound are mixed occurs in the course of the vapor deposition process, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer. Manner.
  • the step of vapor-depositing the compound for the first light-emitting layer and the step of vapor-depositing the compound for the second light-emitting layer In the process, a region composed of the luminescent compound, a region composed of the first host material, or a region composed of the second host material is generated, and the region is the interface between the first light-emitting layer and the second light-emitting layer.
  • the organic EL device according to the second embodiment includes a third light-emitting layer
  • the first light-emitting layer and the second light-emitting layer are in direct contact
  • the first light-emitting layer and the third light-emitting layer It is preferable that it is in direct contact with the light-emitting layer.
  • the layer structure in which "the first light-emitting layer and the third light-emitting layer are in direct contact” is, for example, any of the following aspects (LS4), (LS5) and (LS6) Aspects can also be included.
  • (LS4) A region in which both the first host material and the third host material are mixed in the process of vapor-depositing the compound for the first light-emitting layer and the step for vapor-depositing the compound for the third light-emitting layer occurs and the region is present at the interface between the first and third light-emitting layers.
  • the step of vapor-depositing the compound for the first light-emitting layer and the deposition of the compound for the third light-emitting layer is performed in the course of the vapor deposition process, and the region exists at the interface between the first light-emitting layer and the third light-emitting layer. Manner.
  • the intermediate layer is preferably arranged between the first light-emitting layer and the second light-emitting layer.
  • the intermediate layer is preferably a non-doped layer.
  • the intermediate layer is preferably a layer containing no luminescent compound (dopant material).
  • the intermediate layer preferably does not contain metal atoms.
  • the intermediate layer includes an intermediate layer material.
  • the interlayer material is preferably not a luminescent compound.
  • the material for the intermediate layer is not particularly limited, it is preferably a material other than a light-emitting compound.
  • Materials for the intermediate layer include, for example, 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.
  • the intermediate layer material may be one or both of the first host material contained in the first light-emitting layer and the second host material contained in the second light-emitting layer.
  • the content of each intermediate layer material is preferably 10% by mass or more of the total mass of the intermediate layer.
  • the intermediate layer preferably contains the intermediate layer material in an amount of 60% by mass or more of the total mass of the intermediate layer, more preferably 70% by mass or more of the total mass of the intermediate layer. It is more preferable to contain 80% by mass or more of the intermediate layer, even more preferably 90% by mass or more of the total mass of the intermediate layer, and even more preferably 95% by mass or more of the total mass of the intermediate layer. .
  • the intermediate layer may contain only one type of intermediate layer material, or may contain two or more types. When the intermediate layer contains two or more intermediate layer materials, the upper limit of the total content of the two or more intermediate layer materials is 100% by mass. It should be noted that the second embodiment does not exclude that the intermediate layer contains materials other than the intermediate layer material.
  • the intermediate layer may be composed of a single layer, or may be composed of two or more laminated layers.
  • the thickness of the intermediate layer is not particularly limited, it is preferably 3 nm or more and 15 nm or less, more preferably 5 nm or more and 10 nm or less.
  • the substrate is used as a support for organic EL elements.
  • the substrate for example, glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • a flexible substrate is a (flexible) substrate that can be bent, and examples thereof include a plastic substrate.
  • Materials for forming the plastic substrate include, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic deposition films can also be used.
  • anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more).
  • a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more).
  • ITO Indium Tin Oxide
  • indium oxide-tin oxide containing silicon or silicon oxide indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide , graphene and the like.
  • gold Au
  • platinum Pt
  • nickel Ni
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • iron Fe
  • Co cobalt
  • Cu copper
  • palladium Pd
  • titanium Ti
  • nitrides of metal materials eg, titanium nitride
  • indium oxide-zinc oxide can be formed by a sputtering method using a target in which 1% by mass or more and 10% by mass or less of zinc oxide is added to indium oxide.
  • indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide.
  • a target it can be formed by a sputtering method.
  • it may be produced by a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method, or the like.
  • the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode.
  • materials that can be used as electrode materials such as metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Groups 1 and 2 of the Periodic Table of the Elements.
  • Elements belonging to group 1 or 2 of the periodic table which are materials with a small work function, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium Alkaline earth metals such as (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these can also be used.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such as europium (Eu) and ytterbium (Yb)
  • Yb ytterbium
  • alloys containing these can also be used.
  • cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less).
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca ), alkaline earth metals such as strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as strontium (Sr)
  • alloys containing these e.g., MgAg, AlLi
  • a vacuum deposition method or a sputtering method can be used.
  • a coating method, an inkjet method, or the like can be used.
  • a cathode is formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the magnitude of the work function. can do.
  • These conductive materials can be deposited using a sputtering method, an inkjet method, a spin coating method, or the like.
  • the electron transport layer is a layer containing a substance having a high electron transport property.
  • the electron transport layer contains 1) metal complexes such as aluminum complexes, beryllium complexes and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives and phenanthroline derivatives, and 3) polymer compounds. can be used.
  • low-molecular-weight organic compounds include Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), Metal complexes such as BAlq, Znq, ZnPBO, and ZnBTZ can be used.
  • 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole abbreviation: PBD
  • 1,3-bis[5- (ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene abbreviation: OXD-7
  • 3-(4-tert-butylphenyl)-4-phenyl-5-(4- biphenylyl)-1,2,4-triazole abbreviation: TAZ
  • Complex compounds such as triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4'-bis(5-methylbenzoxa
  • Benzimidazole compounds can be preferably used in the above embodiments.
  • the substances described here are mainly substances having an electron mobility of 10 ⁇ 6 cm 2 /(V ⁇ s) or more. Note that a substance other than the above substances may be used for the electron-transporting layer as long as the substance has higher electron-transporting property than hole-transporting property. Further, the electron transport layer may be composed of a single layer, or may be composed of two or more layers of the above substances laminated.
  • a polymer compound can also be used for the electron transport layer.
  • poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py)
  • poly[(9,9-dioctylfluorene-2 ,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] abbreviation: PF-BPy
  • PF-BPy poly[(9,9-dioctylfluorene-2 ,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)]
  • the electron injection layer is a layer containing a substance with high electron injection properties.
  • the electron injection layer includes lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), and the like.
  • Alkali metals such as, alkaline earth metals, or compounds thereof can be used.
  • a substance having an electron-transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) in Alq, or the like may be used. In this case, electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer.
  • a composite material has excellent electron-injecting and electron-transporting properties because electrons are generated in the organic compound by the electron donor.
  • the organic compound is preferably a material that is excellent in transporting the generated electrons.
  • a substance (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer described above is used. be able to.
  • the electron donor any substance can be used as long as it exhibits an electron donating property with respect to an organic compound.
  • alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide and barium oxide.
  • Lewis bases such as magnesium oxide can also be used.
  • An organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.
  • the method for forming each layer of the organic EL element of the above embodiment is not limited to those specifically mentioned above, but a vacuum deposition method, a sputtering method, a plasma method, a dry film formation method such as an ion plating method, a spin coating method, etc.
  • a known method such as a coating method, a dipping method, a flow coating method, or a wet film forming method such as an inkjet method can be employed.
  • each organic layer of the organic EL element of the above embodiment is not limited except for the cases mentioned above. In general, if the film thickness is too thin, defects such as pinholes are likely to occur. A range of nm to 1 ⁇ m is preferred.
  • An electronic device includes the organic EL element according to any one of the above-described embodiments.
  • Examples of electronic devices include display devices and light-emitting devices.
  • Examples of display devices include display components (eg, organic EL panel modules, etc.), televisions, mobile phones, tablets, and personal computers.
  • Light-emitting devices include, for example, illumination and vehicle lamps.
  • the light-emitting layer is not limited to one layer, and a plurality of light-emitting layers may be laminated.
  • the organic EL device has a plurality of light-emitting layers, at least one organic layer may satisfy the conditions described in the above embodiment, and at least one light-emitting layer contains the compound of the first embodiment. is preferred.
  • one of the plurality of light-emitting layers contains the compound of the first embodiment, for example, even if the other light-emitting layers are fluorescent light-emitting layers, It may be a phosphorescent light-emitting layer that utilizes light emission due to electronic transition to a state.
  • the organic EL element has a plurality of light-emitting layers
  • these light-emitting layers may be provided adjacent to each other, or a so-called tandem-type organic EL device in which a plurality of light-emitting units are stacked via an intermediate layer. It may be an EL element.
  • a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light emitting layer.
  • a barrier layer is disposed in contact with the light-emitting layer and preferably blocks holes, electrons, and/or excitons.
  • the barrier layer transports electrons, and holes reach a layer closer to the cathode than the barrier layer (e.g., electron transport layer). prevent you from doing
  • the organic EL device includes an electron-transporting layer, it preferably includes the barrier layer between the light-emitting layer and the electron-transporting layer.
  • the barrier layer transports holes, and electrons are transported to a layer closer to the anode than the barrier layer (for example, a hole transport layer). prevent it from reaching.
  • the organic EL device includes a hole-transporting layer, it preferably includes the barrier layer between the light-emitting layer and the hole-transporting layer.
  • a barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers.
  • Excitons generated in the light-emitting layer are prevented from moving to a layer closer to the electrode than the barrier layer (for example, an electron-transporting layer and a hole-transporting layer). It is preferable that the light-emitting layer and the barrier layer are bonded.
  • Example 1 A glass substrate (size: 25 mm x 25 mm x 0.7 mm, Geomatec Co., Ltd.) provided with a patterned ITO transparent electrode with a thickness of 130 nm was cleaned with nitrogen plasma for 100 seconds. After that, the glass substrate with the ITO transparent electrode was attached to the holder of the vacuum evaporator. First, compound HT1 and compound HA1 were co-deposited on the surface of a patterned ITO transparent electrode on a glass substrate to form a hole injection layer (HI) with a thickness of 10 nm. The ratio of compound HT1 in this hole injection layer was set to 97% by mass, and the ratio of compound HA1 was set to 3% by mass.
  • HI hole injection layer
  • compound HT1 was deposited to form a first hole transport layer (HT) with a thickness of 80 nm.
  • the compound HT2 was deposited to deposit a second hole-transporting layer (also referred to as an electron blocking layer) (EBL) with a thickness of 10 nm.
  • EBL electron blocking layer
  • Compound BH3 (first host material (BH)) and compound BD1 (first dopant material (BD)) are co-deposited on the second hole transport layer so that the proportion of compound BD1 is 1% by mass. Then, a light-emitting layer having a thickness of 25 nm was formed.
  • Compound ET1 was deposited on the light-emitting layer to form a first electron-transporting layer (also referred to as a hole-blocking layer) (HBL) with a thickness of 10 nm.
  • Compound ET2 was deposited on the first electron-transporting layer (HBL) to form a second electron-transporting layer (ET) with a thickness of 15 nm.
  • Lithium fluoride (LiF) was vapor-deposited on the second electron-transporting layer to form an electron-injecting layer with a thickness of 1 nm.
  • Metal Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.
  • the device configuration of Example 1 is schematically shown as follows.
  • the numbers in parentheses indicate the film thickness (unit: nm).
  • Percentage figures (97%:3%) indicate the ratio (mass %) of compound HT1 and compound HA1 in the hole-injection layer, and percentage figures (99%:1%) indicate the proportion in the light-emitting layer.
  • the ratio (% by mass) of the host material (compound BH3) and the dopant material (compound BD1) is shown.
  • Comparative Examples 1 and 2 Organic EL devices of Comparative Examples 1 and 2 were produced in the same manner as in Example 1, except that the light-emitting layer of Example 1 was changed to the compound shown in Table 1.
  • ⁇ Maximum peak wavelength ⁇ p of light emitted from the element when the element is driven A spectral radiance spectrum was measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to the organic EL element so that the current density of the organic EL element was 10 mA/cm 2 .
  • a maximum peak wavelength ⁇ p (unit: nm) was calculated from the obtained spectral radiance spectrum.
  • the organic EL devices of Example 1 that satisfy the formula (number A) are the organic EL devices of Comparative Examples 1 and 2 that do not satisfy the formula (number A). longer life compared to
  • Example 2 A glass substrate (size: 25 mm x 25 mm x 0.7 mm, Geomatec Co., Ltd.) provided with a patterned ITO transparent electrode with a thickness of 130 nm was cleaned with nitrogen plasma for 100 seconds. After that, the glass substrate with the ITO transparent electrode was attached to the holder of the vacuum evaporator. First, compound HT1 and compound HA1 were co-deposited on the surface of a patterned ITO transparent electrode on a glass substrate to form a hole injection layer (HI) with a thickness of 10 nm. The ratio of compound HT1 in this hole injection layer was set to 97% by mass, and the ratio of compound HA1 was set to 3% by mass.
  • HI hole injection layer
  • compound HT1 was deposited to form a first hole transport layer (HT) with a thickness of 80 nm.
  • the compound HT2 was deposited to deposit a second hole-transporting layer (also referred to as an electron blocking layer) (EBL) with a thickness of 10 nm.
  • EBL electron blocking layer
  • Compound BH2 (first host material (BH)) and compound BD1 (first dopant material (BD)) are co-deposited on the second hole transport layer so that the proportion of compound BD1 is 2% by mass. Then, a light-emitting layer having a thickness of 25 nm was formed.
  • Compound ET3 was deposited on the light-emitting layer to form a first electron-transporting layer (also referred to as a hole-blocking layer) (HBL) with a thickness of 10 nm.
  • Compound ET2 was deposited on the first electron-transporting layer (HBL) to form a second electron-transporting layer (ET) with a thickness of 15 nm.
  • Lithium fluoride (LiF) was vapor-deposited on the second electron-transporting layer to form an electron-injecting layer with a thickness of 1 nm.
  • Metal Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.
  • the device configuration of Example 2 is schematically shown as follows.
  • the numbers in parentheses indicate the film thickness (unit: nm).
  • Percentage figures (97%:3%) indicate the ratio (mass %) of compound HT1 and compound HA1 in the hole-injection layer, and percentage figures (98%:2%) indicate the proportion in the light-emitting layer.
  • the ratio (% by mass) of the host material (compound BH2) and the dopant material (compound BD1) is shown.
  • Comparative Example 3 An organic EL device of Comparative Example 3 was produced in the same manner as in Example 2 except that the light-emitting layer of Example 2 was changed to the compound shown in Table 2.
  • Examples 3 to 5 Organic EL devices of Examples 3 to 5 were produced in the same manner as in Example 2 except that the light-emitting layer of Example 2 was changed to the compound shown in Table 3.
  • Examples 6-7 Organic EL devices of Examples 6 and 7 were produced in the same manner as in Example 2, except that the light-emitting layer of Example 2 was changed to the compound shown in Table 2.
  • ⁇ Maximum peak wavelength ⁇ p of light emitted from the element when the element is driven The maximum peak wavelength ⁇ p (unit: nm) was measured in the same manner as in Example 1.
  • the organic The EL device had a longer life and an improved EQE compared to the organic EL device of Example 5 using a disubstituted anthracene derivative as the first host material.
  • the phosphorescence spectrum (vertical axis: phosphorescent emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn to the rise on the short wavelength side of this phosphorescent spectrum.
  • a tangent line to the rise on the short wavelength side of the phosphorescence spectrum is drawn as follows.
  • This tangent line increases in slope as the curve rises (ie as the vertical axis increases).
  • the tangent line drawn at the point where the value of this slope takes the maximum value is taken as the tangent line to the rise on the short wavelength side of the phosphorescence spectrum.
  • the maximum point with a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side described above, and is closest to the maximum value on the short wavelength side.
  • the tangent line drawn at the point where the value is taken is taken as the tangent line to the rise on the short wavelength side of the phosphorescence spectrum.
  • a F-4500 type spectrofluorophotometer body manufactured by Hitachi High Technology Co., Ltd. was used for the measurement of phosphorescence.
  • a tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. Among the maximum values of the absorption spectrum, consider the tangent line at each point on the curve when moving from the maximum value on the longest wavelength side to the long wavelength direction on the spectrum curve. This tangent line repeats the slope decreasing and then increasing as the curve falls (that is, as the value on the vertical axis decreases). The tangent line drawn at the point where the slope value takes the minimum value on the long wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent line to the fall on the long wavelength side of the absorption spectrum. The maximum absorbance value of 0.2 or less is not included in the maximum value on the longest wavelength side.
  • Affinity Af of compounds is determined by Djulovich, Mayo, Forrest, Thompson, Organic Electronics, 10 (2009) p. 515-520, the first reduction potential (Ere [V]) of the compound measured in dimethylformamide (DMF) solvent and the first oxidation potential of ferrocene similarly measured as an internal standard ( Efc[V]) was calculated by the following formula (number C).
  • Af [eV] -(-1.19 ⁇ (Ere-Efc)-4.78) ... (number C)
  • the oxidation-reduction potential of each compound was measured by DPV measurement according to the procedure shown below.
  • An electrochemical analyzer (manufactured by ALS Co., model number: ALS 852D) was used for the DPV measurement.
  • Solutions for DPV measurements were prepared as follows. Dimethylformamide (DMF) is used as a solvent, tetrabutylammonium hexafluorophosphate as a supporting electrolyte is dissolved in this solvent to a concentration of 100 mmol/L, and the compound to be measured is dissolved at a concentration of 1.0 mmol/L. Then, as an internal standard, ferrocene was dissolved at a concentration of 1.0 mmol/L to prepare a solution for DPV measurement.
  • DMF Dimethylformamide
  • tetrabutylammonium hexafluorophosphate as a supporting electrolyte is dissolved in this solvent to a concentration of 100 mmol/L
  • the compound to be measured is dissolved at a concentration of 1.0 mmol/L.
  • ferrocene was
  • a platinum electrode was used as the auxiliary electrode, a glassy carbon electrode as the working electrode, and a silver/silver chloride electrode as the reference electrode.
  • the measurement conditions for the DPV measurement were a stepwise voltage increase of 0.01 V, a pulse voltage of 0.025 V, a pulse width of 0.05 seconds, a pulse time of 0.2 seconds, and a potential measurement time of 0.02 seconds.
  • Ere as the first reduction potential of the compound to be measured and Efc as the first oxidation potential of ferrocene measured under the above measurement conditions
  • Af of each compound was calculated using the above formula (number C).
  • Table 4 shows the values related to compound evaluation. Affinity Af is shown in Tables 1-3.
  • 1-bromo-2-fluoro-3-nitrobenzene (87.8 g, 399 mmol) was dissolved in 130 mL of trifluoromethanesulfonic acid (TfOH) and cooled to 0.degree.
  • N-iodosuccinimide (108 g, 479 mmol) was added in portions over 40 minutes and the reaction was allowed to reach room temperature gradually over 19 hours.
  • the reaction was again cooled to 0° C., N-iodosuccinimide (8.5 g, 38 mmol) was added and the reaction was allowed to reach room temperature gradually over 19 hours.
  • the reaction was then poured into 400 mL of water and the resulting mixture was neutralized using 40% sodium hydroxide solution and extracted with heptane.
  • 1,3-dibromo-5-(tert-butyl)benzene 13.0 g, 44.5 mmol
  • tris(dibenzylideneacetone)dipalladium(0) Pd 2 dba 3
  • P(tBu) 3 HBF 4 tri-tert-butylphosphonium tetrafluoroborate

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un élément électroluminescent organique (1) comprenant une anode (3), une cathode (4) et une couche électroluminescente (5) disposée entre l'anode (3) et la cathode (4), la couche électroluminescente (5) comprenant un premier composé représenté par la formule générale (1).　Dans la formule générale (1) : n, m et p représentent chacun indépendamment 0, 1, 2 ou 3 ; RA représente un atome d'hydrogène, un substituant RAX ou analogues ; RB représente un atome d'hydrogène, un substituant RBX ou analogues ; RC représente un atome d'hydrogène, un substituant RCX ou analogues ; R1 et R2 représentent chacun indépendamment un atome d'hydrogène, un substituant ou analogues ; et le cycle A, le cycle B et le cycle C représentent chacun indépendamment un cycle aryle substitué ou non substitué comprenant de 6 à 50 atomes de carbone formant un cycle, ou un hétérocycle substitué ou non substitué comprenant de 5 à 50 atomes formant un cycle.
PCT/JP2022/009515 2021-03-05 2022-03-04 Élément électroluminescent organique et dispositif électronique WO2022186390A1 (fr)

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JP2021035440A JP2024084864A (ja) 2021-03-05 有機エレクトロルミネッセンス素子及び電子機器

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020217229A1 (fr) * 2019-04-26 2020-10-29 Idemitsu Kosan Co., Ltd. Composé polycyclique et dispositif électroluminescent organique comprenant le composé polycyclique ou une composition
KR20210043415A (ko) * 2019-10-11 2021-04-21 머티어리얼사이언스 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2021090934A1 (fr) * 2019-11-08 2021-05-14 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
WO2021185712A1 (fr) * 2020-03-17 2021-09-23 Merck Patent Gmbh Composés hétéroaromatiques pour dispositifs électroluminescents organiques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020217229A1 (fr) * 2019-04-26 2020-10-29 Idemitsu Kosan Co., Ltd. Composé polycyclique et dispositif électroluminescent organique comprenant le composé polycyclique ou une composition
KR20210043415A (ko) * 2019-10-11 2021-04-21 머티어리얼사이언스 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2021090934A1 (fr) * 2019-11-08 2021-05-14 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
WO2021185712A1 (fr) * 2020-03-17 2021-09-23 Merck Patent Gmbh Composés hétéroaromatiques pour dispositifs électroluminescents organiques

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