WO2022196749A1 - 有機エレクトロルミネッセンス素子、化合物、及び電子機器 - Google Patents

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

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WO2022196749A1
WO2022196749A1 PCT/JP2022/012157 JP2022012157W WO2022196749A1 WO 2022196749 A1 WO2022196749 A1 WO 2022196749A1 JP 2022012157 W JP2022012157 W JP 2022012157W WO 2022196749 A1 WO2022196749 A1 WO 2022196749A1
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French (fr)
Japanese (ja)
Inventor
拓史 塩見
尚人 松本
行俊 甚出
悠太 東野
俊成 荻原
秀尭 星野
和真 長尾
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Idemitsu Kosan Co Ltd
Toray Industries Inc
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Idemitsu Kosan Co Ltd
Toray Industries Inc
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Priority to US18/550,880 priority Critical patent/US20240188438A1/en
Priority to KR1020267006232A priority patent/KR20260046189A/ko
Priority to KR1020237035235A priority patent/KR102935993B1/ko
Priority to EP22771494.6A priority patent/EP4310931A4/en
Priority to JP2023507172A priority patent/JP7749005B2/ja
Priority to CN202280021072.7A priority patent/CN116998254A/zh
Publication of WO2022196749A1 publication Critical patent/WO2022196749A1/ja
Anticipated expiration legal-status Critical
Priority to JP2025156906A priority patent/JP2026001060A/ja
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Definitions

  • the present invention relates to organic electroluminescent elements, compounds, 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. Fluorescent organic EL devices that use light emission from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but the internal quantum efficiency is said to be limited to 25%. Therefore, studies have been made to improve the performance of organic EL elements.
  • triplet excitons will be used in addition to singlet excitons to allow the organic EL device to emit light more efficiently.
  • highly efficient fluorescent organic EL devices using thermally activated delayed fluorescence hereinafter sometimes simply referred to as “delayed fluorescence” have been proposed and studied.
  • the TADF (Thermally Activated Delayed Fluorescence) mechanism (mechanism) is being studied.
  • TADF Thermally Activated Delayed Fluorescence
  • ⁇ ST small energy difference
  • the heat-activated delayed fluorescence is described, for example, in Chihaya Adachi, “Physical Properties of Organic Semiconductor Devices,” Kodansha, April 1, 2012, pp. 261-268.
  • Patent Documents 1 and 2 disclose compounds having a benzofurocarbazole ring or a benzothienocarbazole ring as compounds that can be used in organic EL devices. Further, Patent Document 2 discloses an organic EL element using the TADF mechanism. Performance of an organic EL element includes, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and life.
  • An object of the present invention is to provide a high-performance organic electroluminescence element, a compound capable of realizing a high-performance organic electroluminescence element, and an electronic device equipped with the organic EL element.
  • an anode a cathode; a light-emitting layer included between the anode and the cathode;
  • the light-emitting layer includes a compound M3 represented by the following general formula (1) and a delayed fluorescent compound M2,
  • the compound M3 and the compound M2 have different structures
  • An organic electroluminescence device is provided in which the singlet energy S 1 (M3) of the compound M3 and the singlet energy S 1 (M2) of the compound M2 satisfy the relationship of the following formula (Equation 1).
  • A is a group represented by any one of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F);
  • Y 1 is an oxygen atom or a sulfur atom, n is 0 or 1, one or more sets of two or more adjacent ones of R 21 to R 28 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 100 and R 21 to R 28 which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted condensed ring are each independently hydrogen atom, halogen atom, cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atom
  • X 1 is an oxygen atom or a sulfur atom
  • one or more sets of two or more adjacent ones of R 11 to R 14 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 15 to R 18 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 19 and R 20 are hydrogen atoms
  • R 11 to R 18 which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted condensed ring are each independently the substituted or unsubstitute
  • R 21 to R 28 which do not form a ring and do not form a substituted or unsubstituted condensed ring;
  • * represents the bonding position to any one of the six-membered ring carbon atoms to which R 21 to R 24 are bonded in the general formula (1), and when n is 1, * represents the bonding position with any one of the carbon atoms of the benzene ring to which R 100 is bonded.
  • an anode a cathode; a light-emitting layer included between the anode and the cathode;
  • the light-emitting layer includes a compound M3 represented by the following general formula (1) and a delayed fluorescent compound M2,
  • the compound M3 and the compound M2 have different structures
  • An organic electroluminescence device is provided in which the singlet energy S 1 (M3) of the compound M3 and the singlet energy S 1 (M2) of the compound M2 satisfy the relationship of the following formula (Equation 1).
  • A is a group represented by any one of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F);
  • Y 1 is an oxygen atom or a sulfur atom, n is 0 or 1, one or more sets of two or more adjacent ones of R 21 to R 28 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 100 and R 21 to R 28 which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted condensed ring are each independently hydrogen atom, halogen atom, cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atom
  • X 1 is an oxygen atom or a sulfur atom
  • one or more sets of two or more adjacent ones of R 11 to R 20 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 11 to R 20 which do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently the substituted or unsubstituted monocyclic ring in the general formula (1).
  • R 21 to R 28 which do not form a ring and do not form a substituted or unsubstituted condensed ring;
  • * represents the bonding position to any one of the six-membered ring carbon atoms to which R 21 to R 24 are bonded in the general formula (1), and when n is 1, * represents the bonding position with any one of the carbon atoms of the benzene ring to which R 100 is bonded.
  • an electronic device equipped with the above-described organic electroluminescence element according to one aspect of the present invention.
  • X 1 is an oxygen atom or a sulfur atom
  • R 100 , R 11 to R 20 and R 22 to R 28 are each independently hydrogen atom, —(L 101 )nx—a group represented by R 101 , nx is 0, 1, 2 or 3;
  • R 101 is an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, unsubstituted (9-phenyl)carbazolyl group, unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothienyl group, unsubstituted (9-dibenzofuranyl)car
  • X 1X is an oxygen atom or a sulfur atom
  • R 11X to R 21X are each independently hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, unsubstituted (9-phenyl)carbazolyl group, unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothienyl group, provided that R 101 is a monovalent group derived from a compound of any one of the general formulas (101) to (106), and when nx is 0, a six-membered ring to which R 11X to R 20X are bonded; and any one of the nitrogen atoms to which R 21X is bonded is bonded to any one of the six-membered ring carbon atoms to which R 11 to R 20 , R 22 to R 28 and R 100 are bonded
  • L 101 is a divalent group derived from a compound of any one of the general formulas (101) to (106), and nx is 1, the six-membered ring carbon atom to which R 11X to R 20X are bonded and any two of the nitrogen atoms to which R 21X is bonded, one is bonded to R 101 and the other is a six-membered ring carbon atom to which R 11 to R 20 , R 22 to R 28 and R 100 are bonded Combine with any one
  • L 101 is a divalent group derived from a compound of any one of the general formulas (101) to (106), and nx is 2 or 3, a six-membered ring to which R 11X to R 20X are bonded any two of the carbon atom and the nitrogen atom to which R 21X is bonded, one of which is bonded to R 101 or L 101 and the other is a six-membered to which R 11 to R 20 , R 22 to R 28 and R 100 are bonded Bonded to any one of the carbon
  • a high-performance organic electroluminescence element a compound capable of realizing a high-performance organic electroluminescence element, and an electronic device equipped with the organic EL element.
  • FIG. 1 is a schematic diagram of an apparatus for measuring transient PL
  • FIG. 4 is a diagram showing an example of a decay curve of transient PL
  • FIG. 3 is a diagram showing the energy level relationship between compound M3 and compound M2 in a light-emitting layer of an example of the organic electroluminescence device according to the first embodiment of the present invention.
  • FIG. 4 is a diagram showing energy levels of compound M3, compound M2, and compound M1 in a light-emitting layer of an example of the organic electroluminescence device according to the second embodiment of the present invention, and a relationship of energy transfer.
  • 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
  • Substituted aryl group (specific example group G1B): an o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, an ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, an ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl) fluorenyl group, a cyanophenyl group,
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
  • a “heterocyclic group” as described herein is a monocyclic group or a condensed ring group.
  • a “heterocyclic group” as described herein is either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • specific examples of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic groups (specific example group G2A), and substituted heterocyclic groups ( Specific example group G2B) and the like can be mentioned.
  • unsubstituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”, and substituted heterocyclic group refers to “substituted or unsubstituted "Heterocyclic group” refers to a "substituted heterocyclic group”.
  • heterocyclic group refers to a "substituted heterocyclic group”.
  • a “substituted heterocyclic group” means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” of the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups of the following specific example group G2B. mentioned.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are only examples, and the "substituted heterocyclic group” described herein specifically includes A group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of Example Group G2B is further replaced with a substituent, and a substituent in the "substituted heterocyclic group" of Specific Example Group G2B A group in which the hydrogen atom of is further replaced with a substituent is also included.
  • Specific example group G2A includes, for example, the following nitrogen atom-containing unsubstituted heterocyclic groups (specific example group G2A1), oxygen atom-containing unsubstituted heterocyclic groups (specific example group G2A2), sulfur atom-containing unsubstituted (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • nitrogen atom-containing unsubstituted heterocyclic groups specifically example group G2A1
  • oxygen atom-containing unsubstituted heterocyclic groups specifically example group G2A2
  • sulfur atom-containing unsubstituted specifically example group G2A3
  • a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), substituted heterocyclic group containing an oxygen atom (specific example group G2B2), substituted heterocyclic ring containing a sulfur atom group (specific example group G2B3), and one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) as a substituent Including substituted groups (example group G2B4).
  • an unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, quinolyl group, an isoquinolyl group, cinnolyl group, a phthalazinyl group, a quinazolinyl
  • an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, azanaphthobenzofuranyl group and diazanaphthobenzofuranyl group;
  • thienyl group an unsubstituted heterocyclic group containing a sulfur atom
  • thienyl group a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothiopheny
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic groups derived from the represented ring structures include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 .
  • a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl) phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group and a biphenylylquinazolinyl group;
  • a substituted heterocyclic group containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, A t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
  • a substituted heterocyclic group containing a sulfur atom (specific example group G2B3): 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 .
  • Substituted or unsubstituted alkyl group Specific examples of the "substituted or unsubstituted alkyl group" described in the specification (specific example group G3) include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B ).
  • unsubstituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is “unsubstituted alkyl group”
  • substituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is It refers to a "substituted alkyl group”.
  • alkyl group includes both an "unsubstituted alkyl group” and a "substituted alkyl group”.
  • a “substituted alkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group” (specific example group G3A) are replaced with substituents, and substituted alkyl groups (specific examples Examples of group G3B) and the like can be mentioned.
  • the alkyl group in the "unsubstituted alkyl group” means a chain alkyl group.
  • the "unsubstituted alkyl group” includes a linear “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are only examples, and the "substituted alkyl group” described herein includes specific example group G3B A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group” of Specific Example Group G3B is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group” of Specific Example Group G3B is further replaced by a substituent included.
  • Unsubstituted alkyl group (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
  • Substituted alkyl group (specific example group G3B): a heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group;
  • Substituted or unsubstituted alkenyl group Specific examples of the "substituted or unsubstituted alkenyl group" described in the specification (specific example group G4) include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B) and the like.
  • unsubstituted alkenyl group refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group", "substituted alkenyl group” means "substituted or unsubstituted alkenyl group ” is a “substituted alkenyl group”.
  • alkenyl group simply referring to an “alkenyl group” includes both an “unsubstituted alkenyl group” and a “substituted alkenyl group”.
  • a “substituted alkenyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include groups in which the following "unsubstituted alkenyl group” (specific example group G4A) has a substituent, and substituted alkenyl groups (specific example group G4B). be done.
  • Unsubstituted alkenyl group (specific example group G4A): a vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.
  • Substituted alkenyl group (specific example group G4B): 1,3-butandienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, a 2-methylallyl group and a 1,2-dimethylallyl group;
  • Substituted or unsubstituted alkynyl group Specific examples of the "substituted or unsubstituted alkynyl group" described in the specification (specific example group G5) include the following unsubstituted alkynyl groups (specific example group G5A).
  • 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.
  • cycloalkyl group (specific example group G6A): a cyclopropyl group, cyclobutyl group, a cyclopentyl group, a cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • cycloalkyl group (specific example group G6B): 4-methylcyclohexyl group;
  • G7 A group represented by -Si (R 901 ) (R 902 ) (R 903 )
  • Specific examples of the group represented by —Si(R 901 )(R 902 )(R 903 ) described in the specification include: -Si(G1)(G1)(G1), - Si (G1) (G2) (G2), - Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3) and -Si(G6)(G6)(G6) is mentioned.
  • G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G1's in -Si(G1)(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -Si (G1) (G2) (G2) are the same or different from each other.
  • a plurality of G1's in -Si(G1)(G1)(G2) are the same or different from each other.
  • a plurality of G2 in -Si(G2)(G2)(G2) are the same or different from each other.
  • a plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other.
  • a plurality of G6 in -Si(G6)(G6)(G6) are the same or different from each other.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G9 A group represented by -S- (R 905 )
  • Specific examples of the group represented by -S-(R 905 ) described in the specification include: -S(G1), -S(G2), -S (G3) and -S (G6) 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.
  • - the plurality of G6 in N (G6) (G6) are the same or different from each other
  • halogen atom described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • 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 "substituted or unsubstituted trialkylsilyl group” described herein are groups represented by -Si(G3)(G3)(G3), where G3 is a specific example A "substituted or unsubstituted alkyl group” according to Group G3. A plurality of G3s in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "unsubstituted trialkylsilyl group” is 1 to 50, preferably 1 to 20, more preferably 1 to 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.
  • 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.
  • * represents a binding position.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents a bonding position.
  • R 921 and R 922 when “one or more pairs of two or more adjacent pairs of R 921 to R 930 are combined to form a ring", is a pair of R 921 and R 922 , a pair of R 922 and R 923 , a pair of R 923 and R 924 , a pair of R 924 and R 930 , a pair of R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R 929 and R 921 .
  • one or more pairs means that two or more of the groups consisting of two or more adjacent groups may form a ring at the same time.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 925 and R 926 are bonded together to form ring Q B
  • the general formula (TEMP-103) The represented anthracene compound is represented by the following general formula (TEMP-104).
  • a group consisting of two or more adjacent pairs forms a ring is not limited to the case where a group consisting of two adjacent "two” is combined as in the above example, but It also includes the case where a pair is combined.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 922 and R 923 are bonded together to form ring Q C
  • the adjacent three R 921 , R 922 and R 923
  • the anthracene compound represented by the general formula (TEMP-103) has It is represented by the general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “condensed ring” to be formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when “one pair of adjacent pairs" forms a “single ring” or a “fused ring", the “single ring” or “fused ring” is a saturated ring, or Unsaturated rings can be formed.
  • ring Q A and ring Q B formed in the general formula (TEMP-104) are each a “monocyclic ring” or a "fused ring”.
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) form a condensed ring by condensing the ring Q A and the ring Q C. If 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 consists of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring having an unsaturated bond in the ring structure and a non-aromatic heterocyclic ring having an unsaturated bond in the ring structure at least one ring selected from the group;
  • the unsaturated bond that the unsaturated ring has in the ring structure is one or both of a double bond and a triple bond.
  • Aliphatic hydrocarbon rings having unsaturated bonds in the ring structure include, for example, cyclohexene and cyclohexadiene.
  • Non-aromatic heterocycles having unsaturated bonds in the ring structure are, for example, dihydropyrans, imidazolines, pyrazolines, quinolidines, indolines and isoindolines.
  • the "saturated ring” is at least one ring selected from aliphatic hydrocarbon rings having no unsaturated bonds and non-aromatic heterocyclic rings having no unsaturated bonds.
  • a saturated ring has no double or triple bonds in the ring structure.
  • 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 atoms.
  • the ring Q A formed by combining R 921 and R 922 shown in the general formula (TEMP-104) has the carbon atom of the anthracene skeleton to which R 921 is bonded and the anthracene skeleton to which R 922 is bonded. It means a ring formed by a skeleton carbon atom and one or more arbitrary atoms.
  • R 921 and R 922 form a ring Q A , the carbon atom of the anthracene skeleton to which R 921 is bound, the carbon atom of the anthracene skeleton to which R 922 is bound, and four carbon atoms and form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.
  • the "arbitrary atom” is preferably at least one atom selected from the group consisting of carbon, nitrogen, oxygen, and sulfur atoms, unless otherwise specified herein.
  • a bond that does not form a ring at any atom may be terminated with a hydrogen atom or the like, or may be substituted with an "optional substituent” described later. If it contains any atoms other than carbon atoms, then the ring formed is a heterocyclic ring.
  • “One or more arbitrary atoms" constituting a monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, unless otherwise specified in the specification.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above “monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section “Substituents described herein” above.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents when the above "saturated ring” or “unsaturated 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. When there are multiple optional substituents, the multiple optional substituents are the same or different from each other.
  • 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 element 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 device of this embodiment has a light-emitting layer included between the anode and the cathode.
  • 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 light-emitting layer 5 may contain a metal complex.
  • the light-emitting layer 5 preferably does not contain a phosphorescent material (dopant material).
  • the light emitting layer 5 preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes. Moreover, it is also preferable that the light-emitting layer 5 does not contain a metal complex.
  • the light-emitting layer 5 contains a delayed fluorescent compound M2 and a compound M3 represented by general formula (1).
  • the compound M2 is preferably a dopant material (also referred to as a guest material, emitter, or light-emitting material), and the compound M3 is a host material (also referred to as a matrix material). is preferred.
  • Compound M3 may be a compound with delayed fluorescence or a compound that does not exhibit delayed fluorescence.
  • Patent Document 2 describes a compound in which benzofuranocarbazole or benzothienocarbazole and dibenzofuran or dibenzothiophene are bonded via a long conjugation length biphenylene (hereinafter sometimes referred to as the compound of Patent Document 2), and an organic EL device in which the compound is included in a light-emitting layer together with a delayed fluorescence compound.
  • the compound of Patent Literature 2 has a low triplet energy and cannot sufficiently confine the triplet energy of the delayed fluorescent compound, so there is a problem that the efficiency of the device cannot be sufficiently improved.
  • the present inventors have found that the compound M3 (compound M3 according to the present embodiment) represented by the general formula (1) is included in the light-emitting layer together with the compound M2 having delayed fluorescence, thereby producing a high-performance organic EL device.
  • Compound M3 according to this embodiment combines benzofuranocarbazole or benzothienocarbazole, which supplies an appropriate amount of holes to the light-emitting layer, and highly durable dibenzofuran or dibenzothiophene via phenylene with a short conjugate length, or It is a compound linked by a single bond. Since the compound M3 according to this embodiment exhibits high triplet energy, it can sufficiently confine the triplet energy of the delayed fluorescent compound. Therefore, according to the organic EL device of the present embodiment, it is possible to realize a high-performance organic EL device, particularly an organic EL device that emits light with high efficiency.
  • Compound M3 contains a compound M3 represented by the following general formula (1).
  • Compound M3 in the present embodiment may be a thermally activated delayed fluorescent compound or a compound that does not exhibit thermally activated delayed fluorescence, but is preferably a compound that does not exhibit thermally activated delayed fluorescence.
  • A is a group represented by any one of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F);
  • Y 1 is an oxygen atom or a sulfur atom, n is 0 or 1, one or more sets of two or more adjacent ones of R 21 to R 28 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 100 and R 21 to R 28 which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted condensed ring are each independently hydrogen atom, halogen atom, cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atom
  • X 1 is an oxygen atom or a sulfur atom
  • one or more sets of two or more adjacent ones of R 11 to R 20 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 11 to R 20 which do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently the substituted or unsubstituted monocyclic ring in the general formula (1).
  • R 21 to R 28 which do not form a ring and do not form a substituted or unsubstituted condensed ring;
  • * represents the bonding position to any one of the six-membered ring carbon atoms to which R 21 to R 24 are bonded in the general formula (1), and when n is 1, * represents the bonding position with any one of the carbon atoms of the benzene ring to which R 100 is bonded.
  • X 1 is an oxygen atom or a sulfur atom
  • one or more sets of two or more adjacent ones of R 11 to R 14 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 15 to R 18 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 19 and R 20 are hydrogen atoms
  • R 11 to R 18 which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted condensed ring are each independently the substituted or unsub
  • R 21 to R 28 which do not form a ring and do not form a substituted or unsubstituted condensed ring;
  • * represents the bonding position to any one of the six-membered ring carbon atoms to which R 21 to R 24 are bonded in the general formula (1), and when n is 1, * represents the bonding position with any one of the carbon atoms of the benzene ring to which R 100 is bonded.
  • One aspect of the general formulas (11A), (11B), (11C), (11D), (11E) and (11F) is represented by the following general formulas (111A), (111B), (111C) and (111D), respectively. ), (111E) and (111F).
  • X 1 has the same definition as X 1 in the general formula (11A), and R 11 to R 18 each independently has the same meaning as R 21 to R 28 which do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring in the general formula (1); * represents the binding position.
  • the compound M3 represented by the general formula (1) can also be represented by the following general formulas (1-1), (1-2), (1-3) or (1-4).
  • the compound of the present embodiment is represented by the following general formula (1-1), (1-2), (1-3) or (1-4) It is a compound that
  • A, R 100 , n, Y 1 and R 21 to R 28 are each independently synonymous with A, R 100 , n, Y 1 and R 21 to R 28 in the general formula (1); R 100 are the same or different from each other.
  • * in the general formulas (11A), (11B), (11C), (11D), (11E) and (11F) represents the bonding position with *1.
  • * in the general formulas (11A), (11B), (11C), (11D), (11E) and (11F) is any carbon atom of the benzene ring to which R 100 is bonded. represents a binding position with one.
  • n 1
  • compound M3 is a compound represented by general formula (12A) below.
  • the compound represented by the following general formula (12A) and the compound (compound M1) represented by the following general formula (2A) are used in combination
  • the compound represented by the following general formula (12C) and a compound (compound M1) represented by general formula (2A) described later can be used in combination, the external quantum efficiency can be improved.
  • the external quantum efficiency and lifetime can be further improved.
  • A, R 100 , Y 1 and R 21 to R 28 are each independently synonymous with A, R 100 , Y 1 and R 21 to R 28 in general formula (1). and a plurality of R 100 are the same or different, provided that * represents the bonding position with any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded.
  • compound M3 is a compound represented by the following general formula (12B).
  • A, R 100 , Y 1 and R 21 to R 28 are each independently synonymous with A, R 100 , Y 1 and R 21 to R 28 in general formula (1). and a plurality of R 100 are the same or different, provided that * represents the bonding position with any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded.
  • compound M3 is a compound represented by the following general formula (12C).
  • A, R 100 , Y 1 and R 21 to R 28 are each independently synonymous with A, R 100 , Y 1 and R 21 to R 28 in general formula (1). and a plurality of R 100 are the same or different, provided that * represents the bonding position with any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded.
  • n is 0, or n is 1 and R 100 is a hydrogen atom.
  • n 0.
  • A is a group represented by general formula (11A), (11B), (11C), (11E) or (11F).
  • A is a group represented by general formula (11E) or (11F).
  • A is a group represented by the general formula (11F).
  • X 1 is an oxygen atom. In one embodiment of compound M3, X 1 is a sulfur atom. In one embodiment of compound M3, Y 1 is an oxygen atom. In one embodiment of compound M3, X 1 and Y 1 are oxygen atoms.
  • R 25 is neither a substituted or unsubstituted dibenzofuranyl group nor a substituted or unsubstituted dibenzothienyl group.
  • R 21 to R 28 are neither substituted or unsubstituted dibenzofuranyl groups nor substituted or unsubstituted dibenzothienyl groups.
  • R 19 and R 20 are hydrogen atoms.
  • R 11 to R 20 are hydrogen atoms.
  • compound M3 is a compound represented by the following general formula (12A-1).
  • a 12 is a group represented by any of the following general formulas (11A-1), (11B-1), (11C-1), (11D-1), (11E-1) and (11F-1) and R 100 , Y 1 and R 21 to R 28 are each independently synonymous with R 100 , Y 1 and R 21 to R 28 in the general formula (1), and a plurality of R 100 are the same as each other. or different, provided that * represents the bonding position to any one of the six-membered ring carbon atoms to which R 21 to R 24 bond. )
  • R 11 to R 18 are each independent and have the same definitions as R 11 to R 18 in the general formula (1), and * represents the bonding position.
  • R 11 to R 18 are hydrogen atoms.
  • the compound M3 is the only compound having a singlet energy S 1 larger than the singlet energy S 1 (M2) of the delayed fluorescent compound M2.
  • R 100 is not a substituted or unsubstituted dibenzofuranyl group.
  • compound M3 is a compound represented by the following general formula (100).
  • X 1 is an oxygen atom or a sulfur atom
  • R 100 , R 11 to R 20 and R 22 to R 28 are each independently hydrogen atom, —(L 101 )nx—a group represented by R 101 , nx is 0, 1, 2 or 3;
  • R 101 is an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, unsubstituted (9-phenyl)carbazolyl group, unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothienyl group, unsubstituted (9-dibenzofuranyl)car
  • X 1X is an oxygen atom or a sulfur atom
  • R 11X to R 21X are each independently hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, unsubstituted (9-phenyl)carbazolyl group, unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothienyl group, provided that R 101 is a monovalent group derived from a compound of any one of the general formulas (101) to (106), and when nx is 0, a six-membered ring to which R 11X to R 20X are bonded; and any one of the nitrogen atoms to which R 21X is bonded is bonded to any one of the six-membered ring carbon atoms to which R 11 to R 20 , R 22 to R 28 and R 100 are bonded
  • L 101 is a divalent group derived from a compound of any one of the general formulas (101) to (106), and nx is 1, the six-membered ring carbon atom to which R 11X to R 20X are bonded and any two of the nitrogen atoms to which R 21X is bonded, one is bonded to R 101 and the other is a six-membered ring carbon atom to which R 11 to R 20 , R 22 to R 28 and R 100 are bonded Combine with any one
  • L 101 is a divalent group derived from a compound of any one of the general formulas (101) to (106), and nx is 2 or 3, a six-membered ring to which R 11X to R 20X are bonded any two of the carbon atom and the nitrogen atom to which R 21X is bonded, one of which is bonded to R 101 or L 101 and the other is a six-membered to which R 11 to R 20 , R 22 to R 28 and R 100 are bonded Bonded to any one of the carbon
  • R 19 and R 20 in general formula (100) are hydrogen atoms.
  • the compound M3 of the present embodiment can be produced, for example, by the method described in Examples below.
  • the compound M3 of the present embodiment can be produced by following the reactions described in the examples below and using known alternative reactions and raw materials that are suitable for the desired product.
  • Specific examples of the compound M3 of the present embodiment include the following compounds. However, the present invention is not limited to specific examples of these compounds.
  • the light-emitting layer of this embodiment contains a delayed fluorescent compound M2.
  • delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.
  • Transient PL measurement is a method of irradiating a sample with a pulse laser to excite it, and measuring the attenuation behavior (transient characteristics) of PL emission after stopping the irradiation.
  • PL emission in the TADF material is classified into an emission component from singlet excitons generated by the first PL excitation and an emission component from singlet excitons generated via triplet excitons.
  • the lifetime of singlet excitons generated by the first PL excitation is on the order of nanoseconds and is very short. Therefore, the light emission from the singlet excitons is rapidly attenuated after irradiation with the pulse laser.
  • delayed fluorescence is emitted from singlet excitons generated via long-lived triplet excitons, so it gradually decays.
  • the emission intensity derived from delayed fluorescence can be obtained.
  • FIG. 2 A schematic diagram of an exemplary apparatus for measuring transient PL is shown in FIG. An example of a transient PL measurement method and delayed fluorescence behavior analysis using FIG. 2 will be described.
  • a transient PL measurement apparatus 100 in FIG. A streak camera 104 for forming a dimensional image and a personal computer 105 for taking in and analyzing a two-dimensional image are provided. Note that the measurement of transient PL is not limited to the apparatus shown in FIG.
  • the sample housed in the sample chamber 102 is obtained by forming a thin film on a quartz substrate, which is doped with a doping material at a concentration of 12% by mass with respect to the matrix material.
  • a thin film sample housed in the sample chamber 102 is irradiated with a pulse laser from the pulse laser unit 101 to excite the doping material. Emission is extracted in a direction 90 degrees to the irradiation direction of the excitation light, the extracted light is spectroscopically separated by the spectroscope 103 , and a two-dimensional image is formed in the streak camera 104 .
  • a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spots correspond to emission intensity.
  • By cutting out this two-dimensional image along a predetermined time axis it is possible to obtain an emission spectrum in which the vertical axis is the emission intensity and the horizontal axis is the wavelength. Also, by cutting out the two-dimensional image along the wavelength axis, it is possible to obtain an attenuation curve (transient PL) in which the vertical axis is the logarithm of the emission intensity and the horizontal axis is time.
  • the following reference compound H1 was used as the matrix material, and the following reference compound D1 was used as the doping material to prepare the thin film sample A as described above, and the transient PL measurement was performed.
  • the attenuation curves were analyzed using the thin film sample A and thin film sample B described above.
  • a thin film sample B was prepared as described above using the following reference compound H2 as a matrix material and the aforementioned reference compound D1 as a doping material.
  • Fig. 3 shows attenuation curves obtained from transient PL measured for thin film sample A and thin film sample B.
  • the vertical axis is the luminous intensity and the horizontal axis is the time. Based on this emission decay curve, the fluorescence intensity of the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state ratio can be estimated.
  • the ratio of the intensity of delayed fluorescence that decays slowly to the intensity of fluorescence that decays quickly is relatively large.
  • Prompt luminescence is luminescence immediately observed from the excited state after excitation with pulsed light (light emitted from a pulse laser) having a wavelength that the delayed fluorescent material absorbs.
  • Delayed luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed thereafter.
  • the amount and ratio of Prompt luminescence and Delay luminescence can be obtained by a method similar to that described in "Nature 492, 234-238, 2012" (reference document 1). It should be noted that the device used to calculate the amounts of Prompt emission and Delay emission is not limited to the device described in Reference Document 1 or the device described in FIG.
  • a sample prepared by the following method is used for measuring the delayed fluorescence of compound M2.
  • compound M2 is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to remove the self-absorption contribution.
  • the sample solution is freeze-degassed and sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.
  • the fluorescence spectrum of the above sample solution is measured with a spectrofluorophotometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of the ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. Using the fluorescence area intensity of both spectra, Morris et al. J. Phys. Chem. 80 (1976) 969, to calculate the total fluorescence quantum yield.
  • the amount and ratio of prompt luminescence and delay luminescence can be determined by a method similar to that described in “Nature 492, 234-238, 2012” (reference document 1). It should be noted that the device used to calculate the amounts of Prompt emission and Delay emission is not limited to the device described in Reference Document 1 or the device described in FIG. In the present embodiment, when the amount of prompt luminescence (immediate luminescence) of the compound to be measured (compound M2) is X P and the amount of delay luminescence (delayed luminescence) is X D , the value of X D /X P is preferably 0.05 or more. The amount and ratio of prompt luminescence and delay luminescence of compounds other than compound M2 in this specification are measured in the same manner as the amount and ratio of prompt luminescence and delay luminescence of compound M2.
  • Compound M2 of the present embodiment can be produced by a known method.
  • Specific examples of the compound M2 of the present embodiment include the following compounds. However, the present invention is not limited to specific examples of these compounds.
  • the energy gap T 77K (M3) at 77 [K] of compound M3 is preferably larger than the energy gap T 77K (M2) at 77 [K] of compound M2. That is, it is preferable to satisfy the relationship of the following formula (Equation 11). T77K (M3)> T77K (M2) (Equation 11)
  • the organic EL element of the present embodiment emits light
  • the energy gap at 77 [K] differs from the triplet energy that is usually defined. Measurement of triplet energy is performed as follows. First, a sample is prepared by sealing a solution of a compound to be measured in an appropriate solvent in a quartz glass tube.
  • the thermally activated delayed fluorescence compound is preferably a compound with a small ⁇ ST.
  • ⁇ ST is small, even at a low temperature (77 [K]), intersystem crossing and reverse intersystem crossing are likely to occur, and an excited singlet state and an excited triplet state coexist.
  • the spectrum measured in the same manner as above includes light emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish from which state the light is emitted.
  • basically the value of the triplet energy is considered to be dominant. Therefore, in this embodiment, although the measurement method is the same as the normal triplet energy T, in order to distinguish the difference in its strict meaning, the value measured as follows is referred to as the energy gap T 77K . .
  • 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.
  • F-4500 type spectrofluorophotometer body manufactured by Hitachi High Technology Co., Ltd. can be used for measurement of phosphorescence.
  • the measuring device is not limited to this, and measurement may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.
  • a method for measuring the singlet energy S1 using a solution includes the following methods.
  • a 10 ⁇ mol/L toluene solution of the compound to be measured is prepared, placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K).
  • a tangent line is drawn with respect to the fall on the long wavelength side of this absorption spectrum, and the wavelength value ⁇ edge [nm] at the intersection of the tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy.
  • Conversion formula (F2): S 1 [eV] 1239.85/ ⁇ edge
  • Examples of the absorption spectrum measuring device include, but are not limited to, a spectrophotometer manufactured by Hitachi (device name: U3310).
  • 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 difference (S 1 ⁇ T 77K ) between the singlet energy S 1 and the energy gap T 77K at 77 [K] is defined as ⁇ ST.
  • the difference ⁇ ST (M2) between the singlet energy S 1 (M2) of compound M2 and the energy gap T 77K (M2) of compound M2 at 77 [K] is preferably less than 0.3 eV and more It is preferably less than 0.2 eV, more preferably less than 0.1 eV, even more preferably less than 0.01 eV. That is, ⁇ ST(M2) preferably satisfies any one of the following formulas (Equation 1A) to (Equation 1D).
  • ⁇ ST (M2) S 1 (M2) - T 77K (M2) ⁇ 0.3 eV (number 1A)
  • ⁇ ST(M2) S 1 (M2) ⁇ T 77K (M2) ⁇ 0.2 eV
  • ⁇ ST(M2) S 1 (M2) ⁇ T 77K (M2) ⁇ 0.01 eV (number 1D)
  • the thickness of the light-emitting layer in the organic EL device according to this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. When 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 content of compound M2 and compound M3 in the light-emitting layer is preferably within the following range, for example.
  • the content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.
  • the content of compound M3 is preferably 20% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 90% by mass or less, and even more preferably 40% by mass or more and 80% by mass or less. . Note that this embodiment does not exclude the case where the light-emitting layer contains a material other than the compound M2 and the compound M3.
  • the light-emitting layer may contain only one type of compound M2, or may contain two or more types.
  • the light-emitting layer may contain only one type of compound M3, or may contain two or more types.
  • FIG. 4 is a diagram showing an example of the relationship between the energy levels of compound M3 and compound M2 in a light-emitting layer.
  • S0 represents the ground state.
  • S1(M2) represents the lowest excited singlet state of compound M2
  • T1(M2) represents the lowest excited triplet state of compound M2.
  • S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3.
  • the lowest excited triplet state T1 of the compound M2 can reverse intersystem cross to the lowest excited singlet state S1 by thermal energy. be.
  • the compound Emission from the lowest excited singlet state S1 (M2) of M2 can be observed. It is believed that the internal quantum efficiency can be theoretically increased to 100% by utilizing delayed fluorescence by this TADF mechanism.
  • the organic EL device of the present embodiment includes, in the light-emitting layer, a delayed fluorescent compound M2, a compound M3 having a higher singlet energy than the compound M2 (compound M3 represented by the general formula (1)), By including, a high-performance organic EL device is realized.
  • the organic EL device of this embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • 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, i.e. alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca) and strontium ( Sr) and other alkaline earth metals, alloys containing these (eg, 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), magnesium (Mg), calcium (Ca) and strontium ( Sr) and other alkaline earth metals, alloys containing these (eg, 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)
  • 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, ie, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), and calcium (Ca). and alkaline earth metals such as strontium (Sr), 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), magnesium (Mg), and calcium (Ca).
  • alkaline earth metals such as strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as
  • 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.
  • a hole injection layer is a layer containing a substance having a high hole injection property.
  • Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, or the like can be used.
  • TDATA 4,4′,4′′-tris(N,N-diphenylamino)triphenylamine
  • TDATA 4,4′,4′′-tris(N,N-diphenylamino)triphenylamine
  • MTDATA 4,4′ , 4′′-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine
  • DPAB 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenyl Amino]biphenyl
  • DNTPD 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene
  • DPA3B 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene
  • high-molecular compounds can also be used as substances with high hole-injection properties.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N'-[4-(4-diphenylamino) phenyl]phenyl-N'-phenylamino ⁇ phenyl)methacrylamide]
  • PTPDMA poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine]
  • polymer compounds such as Poly-TPD).
  • polymer compounds added with acids such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS) are used.
  • PDOT/PSS poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid)
  • PAni/PSS polyaniline/poly(styrenesulfonic acid)
  • a hole-transport layer is a layer containing a substance having a high hole-transport property.
  • Aromatic amine compounds, carbazole derivatives, anthracene derivatives and the like can be used in the hole transport layer.
  • NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • TPD N,N'-bis(3-methylphenyl)-N,N'- Diphenyl-[1,1′-biphenyl]-4,4′-diamine
  • BAFLP 4-phenyl-4′-(9-phenylfluoren-9-yl)triphenylamine
  • BAFLP 4-phenyl-4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl
  • DFLDPBi 4,4′,4′′-triphenyl
  • CBP 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]
  • Carbazole derivatives such as -9H-carbazole (PCzPA) and anthracene derivatives such as t-BuDNA, DNA, and DAnth may also be used.
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • the layer containing a substance with a high hole-transport property is not limited to a single layer, and may be a stack of two or more layers containing the above substances.
  • a material with a larger energy gap closer to the light emitting layer it is preferable to arrange a material with a larger energy gap closer to the light emitting layer.
  • HT-2 used in the examples described later can be mentioned.
  • 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 this embodiment.
  • 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 present embodiment is not limited to those specifically mentioned above, but dry film formation methods such as a vacuum deposition method, a sputtering method, a plasma method, and an ion plating method, and spin coating methods.
  • 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.
  • the film thickness of each organic layer of the organic EL element of the present embodiment is not particularly limited except as mentioned above. A range of several nm to 1 ⁇ m is usually preferable because an applied voltage is required and the efficiency deteriorates.
  • the organic EL device of the second embodiment differs from the organic EL device of the first embodiment in that the light-emitting layer further contains a fluorescent compound M1.
  • the light-emitting layer includes the compound M3 represented by the general formula (1), the delayed fluorescent compound M2, and the fluorescent light-emitting compound M1.
  • compound M1 is preferably a dopant material
  • compound M2 is preferably a host material
  • compound M3 is preferably a host material.
  • One of compound M2 and compound M3 may be referred to as the first host material, and the other may be referred to as the second host material.
  • the light-emitting layer of this embodiment includes a fluorescent compound M1.
  • Compound M1 of this embodiment is not a phosphorescent metal complex.
  • Compound M1 of the present embodiment is preferably not a heavy metal complex. Further, compound M1 of the present embodiment is preferably not a metal complex.
  • Compound M1 of the present embodiment is preferably a compound that does not show thermally activated delayed fluorescence.
  • a fluorescent material can be used as the compound M1 of the present embodiment.
  • fluorescent materials include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylamino chrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing boron atoms, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketo
  • compound M1 When compound M1 is a fluorescent compound, compound M1 preferably emits light with a maximum peak wavelength of 400 nm or more and 700 nm or less.
  • the maximum peak wavelength refers to the maximum emission intensity in the fluorescence spectrum measured for a toluene solution in which the compound to be measured is dissolved at a concentration of 10 ⁇ 6 mol/liter or more and 10 ⁇ 5 mol/liter or less. It refers to the peak wavelength of the fluorescence spectrum.
  • a spectrofluorophotometer F-7000, manufactured by Hitachi High-Tech Science Co., Ltd. is used as a measuring device.
  • Compound M1 preferably exhibits red or green emission.
  • red light emission refers to light emission having a maximum peak wavelength of fluorescence spectrum within the range of 600 nm or more and 660 nm or less.
  • the maximum peak wavelength of compound M1 is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, still more preferably 610 nm or more and 630 nm or less.
  • green light emission refers to light emission having a maximum peak wavelength of fluorescence spectrum within the range of 500 nm or more and 560 nm or less.
  • the maximum peak wavelength of compound M1 is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, still more preferably 510 nm or more and 540 nm or less.
  • blue light emission refers to light emission having a maximum peak wavelength of fluorescence spectrum within the range of 430 nm or more and 480 nm or less.
  • the maximum peak wavelength of the compound M1 is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.
  • Measurement of the maximum peak wavelength of light emitted from the organic EL element 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 .
  • 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).
  • compound M1 is preferably a compound represented by the following general formula (2A).
  • Compound M1 is preferably a compound that emits light with a maximum peak wavelength of 500 nm or more and 560 nm or less.
  • the life can be remarkably improved compared to when a compound having a pyrromethene skeleton is used as the compound M1.
  • Za ring, Zb ring and Zc 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
  • Ra is combined with the Za ring or the Zb ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring
  • Rb is combined with the Za ring or the Zc ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring
  • Ra and Rb 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 alken
  • compound M1 is also preferably a compound represented by general formula (D11) below.
  • the compound represented by the general formula (2A) is also preferably a compound represented by the following general formula (D11).
  • the external quantum efficiency is improved compared to when a compound represented by the following general formula (16) is used as the compound M1.
  • the external quantum efficiency and lifetime can be improved compared to when a compound having a pyrromethene skeleton is used as the compound M1.
  • Rb has the same definition as Rb in the general formula (2A), X 1 is CR 1 or a nitrogen atom; X2 is CR2 or a nitrogen atom; X3 is CR3 or a nitrogen atom; X4 is CR4 or a nitrogen atom; X5 is CR5 or a nitrogen atom; X6 is CR6 or a nitrogen atom; X7 is CR7 , a nitrogen atom, or a carbon atom bonded to X8 by a single bond; X 8 is CR 8 , a nitrogen atom, or a carbon atom bonded to X 7 by a single bond; X 9 is CR 9 or a nitrogen atom; X 10 is CR 10 or a nitrogen atom; X 11 is CR 11 or a nitrogen atom; X 12 is CR 12 or a nitrogen atom; Q is CR Q or a nitrogen atom; one or more sets of adjacent two or more of R 1
  • the compound represented by the general formula (D11) is also preferably represented by the following general formula (D13).
  • R 1 to R 3 , R 5 to R 13 and R Q each independently have the same meaning as R 1 to R 3 , R 5 to R 13 and R Q in the general formula (D11); one or more sets of two or more adjacent ones of R A1 to R A4 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 A1 to R A4 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, 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,
  • the compound represented by the general formula (D11) is also preferably represented by the following general formula (D13A).
  • R 1 , R 3 , R 5 to R 13 , R Q and R A1 to R A4 are each independently R 1 , R 3 and R 5 in general formula (D13).
  • R 13 , R Q and R A1 to R A4 one or more sets of two or more adjacent ones of R A5 to R A9 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 A5 to R A9 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the substituted or unsubstituted It is synonymous with R A1 to R A4 which do not form a single ring and do not form a substituted or unsubstituted condensed ring.
  • a pair consisting of R 5 and R 6 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted They form unsubstituted fused rings or are not attached to each other.
  • R 1 to R 13 and R Q 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 heteroaryl group having 5 to 50 ring-forming atoms is also preferred.
  • R 1 to R 13 and R Q are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms is also preferred.
  • R 1 to R 3 , R 5 to R 13 , R Q and R A1 to R A9 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 heteroaryl group having 5 to 50 ring-forming atoms is also preferred.
  • R 1 to R 3 , R 5 to R 13 , R Q and R A1 to R A9 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms is also preferred.
  • the compound represented by the general formula (D11) is also preferably represented by the following general formula (D14).
  • R 2 , R 6 , R 13 , R Q and RA2 are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.
  • R 13 and R Q are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, A substituted or unsubstituted naphthyl group or a substituted or unsubstituted dibenzofuranyl group is preferred.
  • R 6 and R A2 are preferably each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • compound M1 is also preferably a compound represented by the following general formula (16).
  • the compound represented by the general formula (2A) is also preferably a compound represented by the following general formula (16).
  • the life can be improved as compared with the case where the compound represented by the general formula (D11) is used as the compound M1.
  • the life can be remarkably improved compared to when a compound having a pyrromethene skeleton is used as the compound M1.
  • R 161 to R 177 which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted condensed ring are each independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aral
  • R 161 to R 177 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 5 to 30 ring atoms or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms is preferable.
  • R 168 to R 170 is A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is preferred.
  • R 161 to R 177 are each independently A hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is preferred.
  • R 161 to R 177 are also preferably hydrogen atoms.
  • the multiple R X1 When multiple R X1 are present, the multiple R X1 are the same or different from each other, When multiple R X2 are present, the multiple R X2 are the same or different from each other, When multiple R X3 are present, the multiple R X3 are the same or different from each other, When multiple R X4 are present, the multiple R X4 are the same or different from each other.
  • the set consisting of R 161 and R 162 the set consisting of R 165 and R 166 , It is also preferred that at least one pair of a pair consisting of R 172 and R 173 and a pair consisting of R 176 and R 177 are bonded together to form a ring represented by the general formula (16A).
  • the set consisting of R 165 and R 166 are bonded to each other to form a ring represented by the general formula (16A), and the set consisting of R 172 and R 173 are bonded to each other to form a ring represented by the general formula (16A).
  • the compound M1 is represented by the following general formula (161).
  • the compound represented by the general formula (16) is also preferably a compound represented by the following general formula (161).
  • R 161 to R 164 , R 167 to R 171 , R 174 to R 177 and R X1 to R X4 are each independently R 161 to R 164 in general formula (16). , R 167 to R 171 , R 174 to R 177 and R X1 to R X4 in the general formula (16A).
  • the compound represented by the general formula (16) is also preferably a compound represented by the following general formula (162).
  • R 161 to R 163 , R 168 to R 170 and R 175 to R 177 are each independently R 161 to R 163 and R 168 to R 170 in general formula (16). and R 175 to R 177. )
  • the compound represented by the general formula (16) is also preferably a compound represented by the following general formula (163).
  • R 162 , R 169 and R 176 are each independently synonymous with R 162 , R 169 and R 176 in general formula (16).
  • Compound M1 can be produced by a known method.
  • compound M1 of the present embodiment is shown below. However, the present invention is not limited to specific examples of these compounds.
  • the coordinate bond between the boron atom and the nitrogen atom in the pyrromethene skeleton can be represented in various ways, such as a solid line, a broken line, an arrow, or omitted. In this specification, they are represented by solid lines, dashed lines, or omitted.
  • the singlet energy S 1 (M1) of the compound M1 and the singlet energy S 1 (M2) of the compound M2 preferably satisfy the relationship of the following formula (Equation 2): .
  • the singlet energy S 1 (M3) of compound M3 is preferably higher than the singlet energy S 1 (M1) of compound M1.
  • the singlet energy S 1 (M3) of the compound M3, the singlet energy S 1 (M2) of the compound M2, and the singlet energy S 1 (M1) of the compound M1 satisfy the relationship of the following formula (Formula 2A) is preferred.
  • the fluorescent compound M1 mainly emits light in the light-emitting layer.
  • the organic EL element of this embodiment preferably emits red light or green light.
  • the content ratios of compound M3, compound M2, and compound M1 contained in the light-emitting layer are preferably within the following ranges, for example.
  • the content of compound M3 is preferably 10% by mass or more and 80% by mass or less.
  • the content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.
  • the content of compound M1 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and 0.01% by mass or more and 1% by mass or less. is more preferable.
  • the upper limit of the total content of compound M3, compound M2, and compound M1 in the light-emitting layer is 100% by mass. It should be noted that this embodiment does not exclude materials other than the compound M3, the compound M2, and the compound M1 included in the light-emitting layer.
  • the light-emitting layer may contain only one type of compound M3, or may contain two or more types.
  • the light-emitting layer may contain only one type of compound M2, or may contain two or more types.
  • the light-emitting layer may contain only one type of compound M1, or may contain two or more types.
  • FIG. 5 is a diagram showing an example of the energy level relationship of the compound M3, the compound M2, and the compound M1 in the light-emitting layer.
  • S0 represents the ground state.
  • S1(M1) represents the lowest excited singlet state of compound M1
  • T1(M1) represents the lowest excited triplet state of compound M1.
  • S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2.
  • S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3.
  • the organic EL device of the second embodiment includes, in the light emitting layer, a delayed fluorescent compound M2 and a compound M3 having a singlet energy higher than that of the compound M2 (compound M3 represented by the general formula (1)). , and the compound M1, which has a smaller singlet energy than the delayed fluorescent compound M2. According to the second embodiment, a high-performance organic EL device is realized.
  • the organic EL device of the second embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • 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.
  • [Fourth embodiment] The compound according to the fourth embodiment is the compound represented by the general formula (100) described in the first embodiment. According to the compound of the fourth embodiment, a high-performance organic EL device can be realized.
  • An organic EL element which is one aspect of the fourth embodiment includes the compound of the fourth embodiment (the compound represented by the general formula (100)) in any of the organic layers disposed between the anode and the cathode. It is an organic EL element included in one layer.
  • the compound of the fourth embodiment is a compound capable of realizing a high-performance organic EL device. Therefore, the organic EL element, which is one aspect of the fourth embodiment, also has high performance.
  • the organic EL device material of the fifth embodiment contains the compound of the fourth embodiment. According to the organic EL element material of the sixth embodiment, high-performance organic EL elements and electronic devices can be realized. In addition, the organic EL element material of the sixth embodiment may further contain other compounds. When the organic EL device material of the sixth embodiment further contains other compounds, the other compounds may be solid or liquid.
  • 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 light-emitting layer should satisfy the conditions described in the above embodiments.
  • the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission due to electronic transition from the triplet excited state directly to the ground 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 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The film thickness of ITO was set to 130 nm. After washing, the glass substrate with the transparent electrode lines was mounted on a substrate holder of a vacuum vapor deposition apparatus. First, the compound HT1 and the compound HA were mixed with the transparent electrode on the side on which the transparent electrode lines were formed so as to cover the transparent electrode. Vapor deposition to form a hole injection layer with a thickness of 10 nm.
  • the concentration of the compound HT1 and the concentration of the compound HA in the hole injection layer were set to 97% by mass and 3% by mass, respectively.
  • compound HT1 was deposited on the hole-injection layer to form a first hole-transport layer with a thickness of 110 nm on the hole-injection layer.
  • compound HT2 was deposited on the first hole-transporting layer to form a second hole-transporting layer having a thickness of 5 nm.
  • compound HT3 was deposited on the second hole transport layer to form an electron blocking layer with a thickness of 5 nm.
  • the compound M3-1 as the compound M3 and the compound TADF-1 as the delayed fluorescent compound M2 were co-deposited on the electron blocking layer to form a light-emitting layer with a thickness of 25 nm.
  • the concentration of compound M3-1 in the light-emitting layer was 75% by mass, and the concentration of compound TADF-1 was 25% by mass.
  • compound HBL was vapor-deposited on the light emitting layer to form a hole blocking layer with a thickness of 5 nm.
  • a compound ET was vapor-deposited on this hole blocking layer to form an electron transporting layer with a thickness of 50 nm.
  • lithium fluoride (LiF) was deposited on the electron transport layer to form an electron injecting electrode (cathode) with a thickness of 1 nm.
  • Metal aluminum (Al) was vapor-deposited on this electron-injecting electrode to form a metal Al cathode with a film thickness of 80 nm.
  • the element configuration of the organic EL element according to Example 1 is schematically shown as follows. ITO(130)/HT1:HA(10,97%:3%)/HT1(110)/HT2(5)/HT3(5)/M3-1:TADF-1(25,75%:25%)/ HBL(5)/ET(50)/LiF(1)/Al(80)
  • the numbers in parentheses indicate the film thickness (unit: nm).
  • the percentage numbers (97%:3%) indicate the proportions (% by mass) of the compound HT1 and the compound HA in the hole injection layer, and the percentage numbers (75%:25%). indicates the ratio (% by mass) of compound M3 and compound M2 in the light-emitting layer.
  • Example 2 A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The film thickness of ITO was set to 130 nm. After washing, the glass substrate with the transparent electrode lines was mounted on a substrate holder of a vacuum vapor deposition apparatus. First, the compound HT4 and the compound HA were mixed with the transparent electrode on the side where the transparent electrode lines were formed so as to cover the transparent electrode. Vapor deposition to form a hole injection layer with a thickness of 10 nm.
  • the concentration of the compound HT4 and the concentration of the compound HA in the hole injection layer were set to 97% by mass and 3% by mass, respectively.
  • compound HT4 was deposited on the hole-injection layer to form a first hole-transport layer with a thickness of 110 nm on the hole-injection layer.
  • compound HT2 was deposited on the first hole-transporting layer to form a second hole-transporting layer having a thickness of 5 nm.
  • compound HT3 was deposited on the second hole transport layer to form an electron blocking layer with a thickness of 5 nm.
  • the compound M3-1 as the compound M3, the compound TADF-2 as the delayed fluorescent compound M2, and the compound FD as the compound M1 were co-deposited to a thickness of 25 nm. was formed.
  • the concentration of compound M3-1 in the light-emitting layer was 79.2% by mass
  • the concentration of compound TADF-2 was 20% by mass
  • the concentration of compound FD was 0.8% by mass.
  • compound HBL2 was deposited on the light emitting layer to form a hole blocking layer with a thickness of 5 nm.
  • the compound ET2 and the compound Liq were vapor-deposited on this hole blocking layer to form an electron transport layer with a thickness of 50 nm.
  • the concentration of the compound ET2 and the concentration of the compound Liq in the electron-transporting layer were set to 50% by weight and 50% by weight, respectively.
  • Yb was deposited on the electron transport layer to form an electron injecting electrode (cathode) with a thickness of 1 nm.
  • Metal aluminum (Al) was vapor-deposited on this electron-injecting electrode to form a metal Al cathode with a film thickness of 80 nm.
  • the element configuration of the organic EL element according to Example 2 is schematically shown as follows.
  • %: 0.8%) indicates the ratio (% by mass) of compound M3, compound M2 and compound M1 in the light-emitting layer, and the percentage numbers (50%: 50%) indicate the ratio of compound ET2 and compound ET2 in the electron-transporting layer.
  • the proportion (mass %) of the compound Liq is shown.
  • Examples 3 to 7 and Comparative Example 1 The organic EL devices according to Examples 3 to 7 and Comparative Example 1 were prepared in the same manner as in Example 2, except that the compound M3-1 used in Example 2 was changed to the compound shown in Table 1. .
  • Example 8-9 Organic EL devices according to Examples 8 and 9 were produced in the same manner as in Example 2, except that the compound M3-1 used in Example 2 was changed to the compound shown in Table 2.
  • Example 10 to 19 In the organic EL devices according to Examples 10 to 19, the compound M3-1 used in Example 2 was changed to the compound shown in Table 2, and the compound FD used in Example 2 was changed to the compound shown in Table 2. It was produced in the same manner as in Example 2, except that the compound was changed.
  • maximum peak wavelength ⁇ p 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 device so that the current density was 10 mA/cm 2 .
  • the maximum peak wavelength ⁇ p (unit: nm) was obtained from the obtained spectral radiance spectrum.
  • Example quantum efficiency EQE 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 device so that the current density was 10 mA/cm 2 . From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambassian radiation was performed.
  • the organic EL devices of Examples 2 to 7 containing the compound M3 represented by the general formula (1) and the delayed fluorescent compound M2 in the light-emitting layer were the organic EL devices of Comparative Example 1 in which the compound M3 was replaced with the compound Ref-1. It emitted light with high efficiency compared to the organic EL device.
  • the organic EL devices of Examples 8 to 19 containing the compound M3 represented by the general formula (1), the delayed fluorescent compound M2, and the fluorescent compound M1 in the light emitting layer are the organic EL devices of Comparative Example 1. It emitted light with high efficiency compared to the device. Further, when comparing Examples 8 to 14 with Examples 15 to 19, Example 8 using the compound represented by the general formula (2A) (FD or FD-2) as the fluorescent compound M1 The life of the organic EL devices of Examples 1 to 14 was significantly longer than that of the organic EL devices of Examples 15 to 19 using the compound (FD-3) having a pyrromethene skeleton as the fluorescent compound M1.
  • Examples 8 to 9 using the compound (FD) represented by the general formula (16) as the fluorescent compound M1 exhibited fluorescence emission. Compared to Examples 10 and 11 in which the compound (FD-2) represented by the general formula (D11) was used as the active compound M1, the life span was longer. On the other hand, Examples 10 and 11 using the compound (FD-2) represented by the general formula (D11) as the fluorescent compound M1 were represented by the general formula (16) as the fluorescent compound M1. Compared to Examples 8 and 9 using the compound (FD), the light emission efficiency was high.
  • Examples 10 to 11 using the compounds (M3-11, M3-12) represented by the general formula (12A) as the compound M3 have the general formula ( 12C)
  • the light emission was more efficient than in Examples 12 to 14 using the compounds (M3-13, M3-2 and M3-15) represented by 12C).
  • Example 11 using the compound (M3-12) represented by the general formula (12A) and in which X 1 in A is a sulfur atom has an effect of improving the external quantum efficiency and lifetime. was more pronounced.
  • TADF-1 Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in FIG.
  • the above compound TADF-1 was dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to remove the contribution of self-absorption.
  • the sample solution was freeze-degassed and sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.
  • the fluorescence spectrum of the above sample solution was measured with a spectrofluorophotometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensity of both spectra, Morris et al. J. Phys. Chem. 80 (1976) 969, the total fluorescence quantum yield was calculated according to formula (1).
  • the delayed fluorescence emission in this example means that the amount of delayed emission (delayed emission) is 5% or more of the amount of prompt emission (immediate emission). Specifically, when the amount of prompt light emission (immediate light emission) is X P and the amount of delay light emission (delayed light emission) is X D , the value of X D /X P is 0.05 or more. means.
  • the amount and ratio of prompt luminescence and delay luminescence can be obtained by a method similar to that described in “Nature 492, 234-238, 2012” (reference document 1). It should be noted that the device used to calculate the amounts of Prompt emission and Delay emission is not limited to the device described in Reference Document 1 or the device described in FIG. Regarding compound TADF-1, it was confirmed that the amount of delayed luminescence (delayed luminescence) was 5% or more of the amount of prompt luminescence (immediate luminescence). Specifically, the compound TADF-1 had a value of X D /X P of 0.05 or more.
  • ⁇ Singlet energy S 1 The singlet energies S 1 of compounds M3-1, M3-6 to M3-15, compounds TADF-1 to TADF-2, compounds FD, FD-2, FD-3 and compound Ref-1 are calculated by the solution method described above. It was measured.
  • ⁇ Energy gap T at 77 [K] 77K T 77K of compounds M3-1, M3-6 to M3-15, compounds TADF-1 to TADF-2, and compound Ref-1 are the above-mentioned "relationship between triplet energy and energy gap at 77 [K]". Measured by the described method for measuring the energy gap T 77K . In addition, ⁇ ST was confirmed from the measurement result of T77K and the value of the above singlet energy S1.
  • ⁇ Maximum peak wavelength ⁇ of the compound The maximum peak wavelength ⁇ of compounds TADF-1, compounds FD, FD-2 and FD-3 was measured by the following method. A 5 ⁇ mol/L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). In this example, the emission spectrum was measured with a spectrophotometer manufactured by Hitachi (device name: F-7000). 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 was defined as the maximum peak wavelength ⁇ .
  • Organic EL element 2... Substrate, 3... Anode, 4... Cathode, 5... Light emitting layer, 6... Hole injection layer, 7... Hole transport layer, 8... Electron transport layer, 9... Electron injection layer.

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