WO2021162057A1 - 有機エレクトロルミネッセンス素子及び電子機器 - Google Patents

有機エレクトロルミネッセンス素子及び電子機器 Download PDF

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WO2021162057A1
WO2021162057A1 PCT/JP2021/005077 JP2021005077W WO2021162057A1 WO 2021162057 A1 WO2021162057 A1 WO 2021162057A1 JP 2021005077 W JP2021005077 W JP 2021005077W WO 2021162057 A1 WO2021162057 A1 WO 2021162057A1
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unsubstituted
light emitting
substituted
ring
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English (en)
French (fr)
Japanese (ja)
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聡美 田崎
西村　和樹
弘明 豊島
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Priority to CN202180005612.8A priority Critical patent/CN114450817A/zh
Priority to KR1020227010849A priority patent/KR102897073B1/ko
Priority to JP2022500454A priority patent/JP7569368B2/ja
Publication of WO2021162057A1 publication Critical patent/WO2021162057A1/ja
Priority to US17/463,266 priority patent/US11552259B1/en
Priority to US17/860,631 priority patent/US20220393113A1/en
Anticipated expiration legal-status Critical
Priority to JP2024144576A priority patent/JP7783364B2/ja
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Definitions

  • the present invention relates to an organic electroluminescence device and an electronic device.
  • Organic electroluminescence devices (hereinafter, may be referred to as "organic EL devices") are applied to full-color displays such as mobile phones and televisions.
  • organic EL devices When a voltage is applied to the organic EL element, 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 are recombined to form excitons.
  • the injected holes and electrons are recombined to form excitons.
  • singlet excitons are generated at a rate of 25%
  • triplet excitons are generated at a rate of 75%.
  • the performance of the organic EL element includes, for example, brightness, emission wavelength, chromaticity, luminous efficiency, drive voltage, and life.
  • a vasophenanthroline (BCP) as a phenanthroline compound having a phenanthroline skeleton is deposited on a light emitting layer to form an electron transport layer, and further, BCP and Cs (cesium) are co-deposited to form an electron.
  • An organic EL element in which an injection layer is formed and aluminum is vapor-deposited to form a cathode is described.
  • One of the objects of the present invention is to provide an organic electroluminescence element having improved performance. Another object of the present invention is to provide an organic electroluminescence device having improved luminous efficiency and a long life, and to provide an electronic device equipped with the organic electroluminescence device.
  • the present invention is an organic electroluminescence device.
  • Two or more light emitting units arranged between the anode and the cathode It has a first cathode-side organic layer disposed between the anode and the cathode.
  • at least one light emitting unit is a laminated light emitting unit.
  • the first cathode side organic layer is arranged on the cathode side of at least one of the laminated light emitting units.
  • the first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton and contains a phenanthroline compound.
  • the laminated light emitting unit includes a first light emitting layer and a second light emitting layer.
  • the first light emitting layer contains the first host material and
  • the second light emitting layer contains a second host material and The first host material and the second host material are different from each other.
  • the first light emitting layer contains at least the first light emitting compound exhibiting light emission having a maximum peak wavelength of 500 nm or less.
  • the second light emitting layer contains at least a second light emitting compound exhibiting light emission having a maximum peak wavelength of 500 nm or less.
  • the first luminescent compound and the second luminescent compound are the same as or different from each other.
  • T 1 (H1) of the first host material and the triplet energy T 1 (H2) of the second host material satisfy the relationship of the following mathematical formula (Equation 3).
  • Organic electroluminescence devices are provided.
  • the present invention is an organic electroluminescence device.
  • Two or more light emitting units arranged between the anode and the cathode It has a first cathode-side organic layer disposed between the anode and the cathode.
  • at least one light emitting unit is a laminated light emitting unit.
  • the first cathode side organic layer is arranged on the cathode side of at least one of the laminated light emitting units.
  • the first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton and contains a phenanthroline compound.
  • the laminated light emitting unit includes a first light emitting layer and a second light emitting layer.
  • the first light emitting layer contains the first host material and
  • the second light emitting layer contains a second host material and
  • the first host material has a structure under the following condition (i) or a structure under the following condition (ii) in the molecule.
  • the second host material is an anthracene derivative.
  • the first host material and the second host material are different from each other.
  • the first light emitting layer contains at least the first light emitting compound exhibiting light emission having a maximum peak wavelength of 500 nm or less.
  • the second light emitting layer contains at least a second light emitting compound exhibiting light emission having a maximum peak wavelength of 500 nm or less.
  • the first luminescent compound and the second luminescent compound are the same as or different from each other.
  • Organic electroluminescence devices are provided.
  • Condition (i) The first benzene ring and the second benzene ring have a biphenyl structure in which they are connected by a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are formed. At least one portion other than the single bond is further linked by cross-linking.
  • a linking structure including a benzene ring and a naphthalene ring linked by a single bond is provided, and the benzene ring and the naphthalene ring in the linking structure each independently further have a monocyclic ring or a condensed ring. Condensed or uncondensed, the benzene ring and the naphthalene ring in the linked structure are further linked by cross-linking at at least one portion other than the single bond.
  • an electronic device equipped with the organic electroluminescence element according to the above-mentioned one aspect of the present invention is provided.
  • an organic electroluminescence device having improved performance.
  • an organic electroluminescence element having improved luminous efficiency and a long life.
  • an electronic device equipped with the organic electroluminescence element.
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • a hydrogen atom that is, a light hydrogen atom, a deuterium atom, or a deuterium atom is located at a bondable position in which a symbol such as "R” or a "D” representing a deuterium atom is not specified in the chemical structural formula. It is assumed that the deuterium atom is bonded.
  • the ring-forming carbon number constitutes the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound). Represents the number of carbon atoms among the atoms to be used. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon number.
  • the "ring-forming carbon number" described below shall be the same unless otherwise specified.
  • the benzene ring has 6 ring-forming carbon atoms
  • the naphthalene ring has 10 ring-forming carbon atoms
  • the pyridine ring has 5 ring-forming carbon atoms
  • the furan ring has 4 ring-forming carbon atoms.
  • the ring-forming carbon number of the 9,9-diphenylfluorenyl group is 13
  • the ring-forming carbon number of the 9,9'-spirobifluorenyl group is 25.
  • the carbon number of the alkyl group is not included in the ring-forming carbon number of the benzene ring.
  • the ring-forming carbon number of the benzene ring substituted with the alkyl group is 6. Further, when the naphthalene ring is substituted with an alkyl group as a substituent, for example, the carbon number of the alkyl group is not included in the ring-forming carbon number of the naphthalene ring. Therefore, the ring-forming carbon number of the naphthalene ring substituted with the alkyl group is 10.
  • the number of ring-forming atoms is a compound (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocycle) having a structure in which atoms are cyclically bonded (for example, a monocycle, a fused ring, and a ring assembly).
  • a compound for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocycle
  • Atoms that do not form a ring for example, a hydrogen atom that terminates the bond of atoms that form a ring
  • atoms included in the substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms.
  • the "number of ring-forming atoms" described below shall be the same unless otherwise specified.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6.
  • a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of the quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
  • the "carbon number XX to YY” in the expression "ZZ group having a substituted or unsubstituted carbon number XX to YY” represents the carbon number when the ZZ group is unsubstituted and is substituted. Does not include the carbon number of the substituent in the case.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • the number of atoms XX to YY in the expression "the ZZ group having the number of atoms XX to YY substituted or unsubstituted” represents the number of atoms when the ZZ group is unsubstituted and is substituted. Does not include the number of atoms of the substituent in the case.
  • "YY” is larger than “XX”
  • "XX” means an integer of 1 or more
  • YY" means an integer of 2 or more.
  • the unsubstituted ZZ group represents the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group", and the substituted ZZ group is the "substituted or unsubstituted ZZ group". Represents the case where is a "substitution ZZ group”.
  • the term "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that the hydrogen atom in the ZZ group is not replaced with the substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a light hydrogen atom, a deuterium atom, or a tritium atom.
  • substitution in the case of “substituent or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with the substituent.
  • substitution in the case of “BB group substituted with AA group” means that one or more hydrogen atoms in the BB group are replaced with AA group.
  • the ring-forming carbon number of the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise stated herein. ..
  • 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 stated herein. be.
  • the carbon number of the "unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated herein.
  • the carbon number of the "unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated herein.
  • the carbon number of the "unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated herein.
  • the ring-forming carbon number of the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise stated herein. be.
  • the ring-forming carbon number of the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18. ..
  • 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. ⁇ 18.
  • the carbon number of the "unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated herein.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in the present specification include the following unsubstituted aryl group (specific example group G1A) and a substituted aryl group (specific example group G1B). ) Etc. can be mentioned.
  • the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "unsubstituted aryl group”
  • the substituted aryl group is the "substituted or unsubstituted aryl group”.
  • aryl group includes both "unsubstituted aryl group” and “substituted aryl group”.
  • the "substituted aryl group” means a group in which one or more hydrogen atoms of the "unsubstituted aryl group” are replaced with a substituent.
  • Examples of the “substituted aryl group” include a group in which one or more hydrogen atoms of the "unsubstituted aryl group” of the following specific example group G1A are replaced with a substituent, and a substituted aryl group of the following specific example group G1B. And the like.
  • aryl group (Specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, Anthril group, Benzoanthril group, Phenantril group, Benzophenanthril group, Fenarenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl
  • aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, Parakisilyl group, Meta-kisilyl group, Ortho-kisilyl group, Para-isopropylphenyl group, Meta-isopropylphenyl group, Ortho-isopropylphenyl group, Para-t-butylphenyl group, Meta-t-butylphenyl group, Ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-Dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis (4-methylphenyl) fluorenyl group, 9,9-bis (4-isopropylphenyl) fluorenyl group, 9,9-bis (4-t-butylphenyl) fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Tripheny
  • heterocyclic group is a cyclic group containing at least one heteroatom in the ring-forming atom.
  • the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
  • the "heterocyclic group” described herein is a monocyclic group or a condensed ring group.
  • the “heterocyclic group” described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in the present specification include the following unsubstituted heterocyclic group (specific example group G2A) and a substituted heterocyclic group (specific example group G2). Specific example group G2B) and the like can be mentioned.
  • the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is the "unsubstituted heterocyclic group”
  • the substituted heterocyclic group is "substituted or unsubstituted”.
  • heterocyclic group is a “substituted heterocyclic group”.
  • heterocyclic group is simply referred to as “unsubstituted heterocyclic group” and “substituted heterocyclic group”. Including both.
  • substituted heterocyclic group means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group” are replaced with a substituent.
  • substituted heterocyclic group examples include a group in which the hydrogen atom of the "unsubstituted heterocyclic group” of the following specific example group G2A is replaced, an example of the substituted heterocyclic group of the following specific example group G2B, and the like. Can be mentioned.
  • the examples of the "unsubstituted heterocyclic group” and the “substituted heterocyclic group” listed here are merely examples, and the "substituted heterocyclic group” described in the present specification specifically refers to the "substituted heterocyclic group”.
  • the specific example group G2A includes, for example, an unsubstituted heterocyclic group containing the following nitrogen atom (specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), and an unsubstituted heterocyclic group containing a sulfur atom. (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) is included.
  • the specific example group G2B is, for example, a substituted heterocyclic group containing the following nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), and a substituted heterocycle containing a sulfur atom.
  • One or more hydrogen atoms of the group (specific example group G2B3) and the monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are the substituents. Includes replaced groups (specific example group G2B4).
  • -Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazoleyl group, Oxazolyl group, Isooxazolyl group, Oxaziazolyl group, Thiazolyl group, Isothiazolyl group, Thiasia Zoryl group, Pyridyl group, Pyridadinyl group, Pyrimidinyl group, Pyrazinel group, Triazinyl group, Indrill group, Isoin drill group, Indridinyl group, Kinolidinyl group, Quinoline group, Isoquinolyl group, Synnolyl group, Phtaladinyl group, Kinazolinyl group, Kinoxalinyl group, Benzoimidazolyl group, Indazolyl group, Phenantrolinyl group, Phenantridinyl group, Acridiny
  • -Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): Frill group, Oxazolyl group, Isooxazolyl group, Oxaziazolyl group, Xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naftbenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholine group, Ginaftfuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftbenzofuranyl group and diazanaphthobenzofuranyl group.
  • Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naftbenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzoisothiazolyl group, Phenothiadinyl group, Dinaftthiophenyl group (dinaftthienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaft benzothiophenyl group
  • the X A and Y A each independently, an oxygen atom, a sulfur atom, NH, or is CH 2. Provided that at least one of X A and Y A represents an oxygen atom, a sulfur atom, or is NH.
  • at least one is NH of X A and Y A, or a CH 2, in the general formula (TEMP-16) ⁇ (TEMP -33)
  • the monovalent heterocyclic group derived from the ring structure represented includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2.
  • -Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-Phenyl) carbazolyl group, (9-biphenylyl) carbazolyl group, (9-Phenyl) Phenylcarbazolyl group, (9-naphthyl) carbazolyl group, Diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methylbenzoimidazolyl group, Ethylbenzoimidazolyl group, Phenyltriazinyl group, Biphenylyl triazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group and biphenylylquinazolinyl group.
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in the present specification include the following unsubstituted alkyl group (specific example group G3A) and a substituted alkyl group (specific example group G3B). ).
  • the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is the "unsubstituted alkyl group”
  • the substituted alkyl group means the "substituted or unsubstituted alkyl group".
  • alkyl group includes both "unsubstituted alkyl group” and "substituted alkyl group”.
  • the "substituted alkyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkyl group” include a group in which one or more hydrogen atoms in the following "unsubstituted alkyl group” (specific example group G3A) are replaced with a substituent, and a substituted alkyl group (specific example). Examples of group G3B) can be mentioned.
  • the alkyl group in the "unsubstituted alkyl group” means a chain alkyl group. Therefore, the "unsubstituted alkyl group” includes a linear "unsubstituted alkyl group” and a branched "unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the “substituted alkyl group” listed here are only examples, and the "substituted alkyl group” described in the present specification includes the specific example group G3B.
  • 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.
  • Substituent alkyl group Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.
  • Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in the present specification include the following unsubstituted alkenyl group (specific example group G4A) and a substituted alkenyl group (specific example group). G4B) and the like can be mentioned.
  • the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group” is a "substituted or unsubstituted alkenyl group”. Refers to the case where "is a substituted alkenyl group”.
  • alkenyl group includes both "unsubstituted alkenyl group” and "substituted alkenyl group”.
  • the "substituted alkenyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include a group in which the following "unsubstituted alkenyl group” (specific example group G4A) has a substituent, an example of a substituted alkenyl group (specific example group G4B), and the like. Be done.
  • the examples of the "unsubstituted alkenyl group” and the “substituted alkenyl group” listed here are only examples, and the "substituted alkenyl group” described in the present specification includes the specific example group G4B.
  • Unsubstituted alkenyl group (specific example group G4A): Vinyl group, Allyl group, 1-butenyl group, 2-butenyl group and 3-butenyl group.
  • Substituent alkenyl group (specific example group G4B): 1,3-Butandienyl group, 1-Methyl vinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-Methylallyl group and 1,2-dimethylallyl group.
  • alkynyl groups and “substituted alkynyl groups”.
  • the "substituted alkynyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include a group in which one or more hydrogen atoms are replaced with a substituent in the following "unsubstituted alkynyl group” (specific example group G5A).
  • Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” described in the present specification include the following unsubstituted cycloalkyl group (specific example group G6A) and a substituted cycloalkyl group (specific example group G6A). Specific example group G6B) and the like can be mentioned.
  • the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is the “unsubstituted cycloalkyl group", and the substituted cycloalkyl group is the "substituted or unsubstituted cycloalkyl group". Refers to the case where the "cycloalkyl group” is a "substituted cycloalkyl group”.
  • the term “cycloalkyl group” is simply referred to as "unsubstituted cycloalkyl group” and "substituted cycloalkyl group”. Including both.
  • the "substituted cycloalkyl group” means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include a group in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group” (specific example group G6A) are replaced with a substituent, and a substituted cycloalkyl group. Examples of (Specific example group G6B) can be mentioned.
  • cycloalkyl group (Specific example group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • Substituent cycloalkyl group (Specific example group G6B): 4-Methylcyclohexyl group.
  • G7 of the groups represented by ⁇ Si (R 901 ) (R 902 ) (R 903 ) described in the present specification include. -Si (G1) (G1) (G1), -Si (G1) (G2) (G2), -Si (G1) (G1) (G2), -Si (G2) (G2) (G2), -Si (G3) (G3), and -Si (G6) (G6) (G6) (G6) Can be mentioned.
  • G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.
  • G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
  • G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.
  • G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
  • -A plurality of G1s in Si (G1) (G1) (G1) are the same as or different from each other.
  • -A plurality of G2s in Si (G1) (G2) (G2) are the same as or different from each other.
  • -A plurality of G1s in Si (G1) (G1) (G2) are the same as or different from each other.
  • -A plurality of G2s in Si (G2) (G2) (G2) are the same as or different from each other.
  • -A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other.
  • -A plurality of G6s in Si (G6) (G6) (G6) are the same as or different from each other.
  • G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
  • G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
  • G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
  • G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
  • G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
  • G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
  • G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
  • G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
  • G10 -N (G1) (G1), -N (G2) (G2), -N (G1) (G2), -N (G3) (G3) and -N (G6) (G6)
  • G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
  • G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
  • G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
  • G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
  • a plurality of G1s in -N (G1) (G1) are the same as or different from each other.
  • -A plurality of G2s in N (G2) (G2) are the same as or different from each other.
  • -A plurality of G3s in N (G3) (G3) are the same as or different from each other.
  • a plurality of G6s in -N (G6) (G6) are the same as or different from each other.
  • Halogen atom Specific examples of the "halogen atom” described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
  • the "unsubstituted fluoroalkyl group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
  • the "substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the "fluoroalkyl group” are replaced with a substituent.
  • the "substituted fluoroalkyl group” described in the present specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent.
  • groups in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group” are further replaced by the substituent.
  • Specific examples of the "unsubstituted fluoroalkyl group” include an example of a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a fluorine atom.
  • the "unsubstituted haloalkyl group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
  • the "substituted haloalkyl group” means a group in which one or more hydrogen atoms of the "haloalkyl group” are replaced with a substituent.
  • the "substituted haloalkyl group” described in the present specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent, and a "substitution".
  • haloalkyl group groups in which one or more hydrogen atoms of the substituents in the "haloalkyl group” are further replaced by the substituents.
  • substituents in the "haloalkyl group” include an example of a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with halogen atoms.
  • the haloalkyl group may be referred to as an alkyl halide group.
  • a specific example of the "substituted or unsubstituted alkoxy group” described in the present specification is a group represented by —O (G3), where G3 is the “substituted or unsubstituted” described in the specific example group G3. It is an unsubstituted alkyl group.
  • the "unsubstituted alkoxy group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted alkylthio group” described in the present specification is a group represented by ⁇ S (G3), where G3 is the “substituted or substituted” described in the specific example group G3. It is an unsubstituted alkyl group.
  • the "unsubstituted alkylthio group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted aryloxy group” described in the present specification is a group represented by —O (G1), where G1 is the “substitution” described in the specific example group G1. Alternatively, it is an unsubstituted aryl group.
  • the ring-forming carbon number of the "unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise stated herein.
  • -"Substituted or unsubstituted arylthio group A specific example of the "substituted or unsubstituted arylthio group” described in the present specification is a group represented by -S (G1), where G1 is the "substituted or substituted arylthio group” described in the specific example group G1. It is an unsubstituted aryl group. " The ring-forming carbon number of the "unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise stated herein.
  • -"Substituted or unsubstituted trialkylsilyl group Specific examples of the "trialkylsilyl group” described in the present specification are groups represented by ⁇ Si (G3) (G3) (G3), where G3 is described in the specific example group G3. It is a "substituted or unsubstituted alkyl group”. -A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other.
  • the carbon number of each alkyl group of the "trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.
  • the "unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group” is unless otherwise specified herein. , 7 to 50, preferably 7 to 30, and more preferably 7 to 18.
  • Specific examples of the "substituted or unsubstituted aralkyl group” include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, and an ⁇ .
  • -Naphthylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group and the like.
  • substituted or unsubstituted aryl groups described herein are preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-unless otherwise described herein.
  • the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzoimidazolyl group, or a phenyl group, unless otherwise described herein.
  • Nantrolinyl 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) Carbazole-1-yl Group, (9-Phenyl) Carbazole-2-yl Group, (9-Phenyl) Carbazole-3-yl Group, or (9-Phenyl) Carbazole Group,
  • carbazolyl group is specifically one of the following groups unless otherwise described in the present specification.
  • the (9-phenyl) carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.
  • dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups unless otherwise described in the present specification.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-, unless otherwise stated herein. It is a butyl group or the like.
  • the "substituted or unsubstituted arylene group” described herein is derived by removing one hydrogen atom on the aryl ring from the above "substituted or unsubstituted aryl group” 2 It is the basis of the value.
  • the "substituted or unsubstituted arylene group” (specific example group G12), by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in the specific example group G1. Examples include the induced divalent group.
  • the "substituted or unsubstituted divalent heterocyclic group" described in the present specification shall exclude one hydrogen atom on the heterocycle from the above "substituted or unsubstituted heterocyclic group". It is a divalent group derived by.
  • specific example group G13 of the "substituted or unsubstituted divalent heterocyclic group"
  • Examples thereof include a divalent group derived by removing an atom.
  • the "substituted or unsubstituted alkylene group” described herein is derived by removing one hydrogen atom on the alkyl chain from the above "substituted or unsubstituted alkyl group” 2 It is the basis of the value.
  • the "substituted or unsubstituted alkylene group” (specific example group G14), by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group” described in the specific example group G3. Examples include the induced divalent group.
  • the substituted or unsubstituted arylene group described in the present specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise described in the present specification.
  • Q 1 ⁇ Q 10 are each independently a hydrogen atom or a substituent.
  • the formulas Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents a binding position.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably a group according to any of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise described herein. Is.
  • Q 1 ⁇ Q 9 are independently a hydrogen atom or a substituent.
  • the set of two adjacent sets is one set. 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, and a pair of R 925 .
  • the above-mentioned "one or more sets” means that two or more sets of two or more adjacent sets may form a ring at the same time.
  • R 921 and R 922 are coupled to each other to form a ring Q A
  • R 925 and R 926 are coupled to each other to form a ring Q B
  • the above general formula (TEMP-103) is used.
  • the anthracene compound represented is represented by the following general formula (TEMP-104).
  • the formed "monocycle” or “condensed ring” may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when “one set of two adjacent sets” forms a “monocycle” or “condensed ring”, the “monocycle” or “condensed ring” is a saturated ring or a saturated ring.
  • An unsaturated ring can be formed.
  • the general formula (TEMP-104) Ring Q A and ring Q B formed in respectively the “monocyclic” or “fused rings”. Further, the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “condensed rings”.
  • the ring Q A and the ring Q C of 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 a monocyclic ring. If the ring Q A of the general formula (TMEP-104) is a naphthalene ring, the ring Q A is a fused ring.
  • the "unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocycle.
  • saturated ring is meant an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
  • aromatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G1 is terminated by a hydrogen atom.
  • aromatic heterocycle include a structure in which the aromatic heterocyclic group given as a specific example in the specific example group G2 is terminated by a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G6 is terminated by a hydrogen atom.
  • Forming a ring means forming a ring with only a plurality of atoms in the mother skeleton, or with a plurality of atoms in the mother skeleton and one or more arbitrary elements.
  • the ring Q A where the R 921 and R 922 are bonded formed with each other, the carbon atoms of the anthracene skeleton R 921 are attached, anthracene R 922 are bonded It means a ring formed by a carbon atom of a skeleton and one or more arbitrary elements.
  • the carbon atom of the anthracene skeleton and R 922 are attached, four carbon atoms
  • the ring formed by R 921 and R 922 is a benzene ring.
  • arbitrary element is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise described in the present specification.
  • the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later.
  • the ring formed is a heterocycle.
  • the number of "one or more arbitrary elements" constituting the monocycle or condensed ring is preferably 2 or more and 15 or less, and more preferably 3 or more and 12 or less. , More preferably 3 or more and 5 or less.
  • the "monocycle” and the “condensed ring” are preferably “monocycles”.
  • the "saturated ring” and the “unsaturated ring” are preferably “unsaturated rings”.
  • the "monocycle” is preferably a benzene ring.
  • the "unsaturated ring” is preferably a benzene ring.
  • one or more pairs of two or more adjacent pairs are bonded to each other to form a plurality of atoms in the mother skeleton and one or more 15 elements. It forms a substituted or unsubstituted "unsaturated ring” consisting of at least one element selected from the group consisting of the following carbon element, nitrogen element, oxygen element, and sulfur element.
  • the substituent is, for example, an "arbitrary substituent” described later.
  • Specific examples of the substituent when the above-mentioned “monocycle” or “condensed ring” has a substituent are the substituents described in the above-mentioned “Substituents described in the present specification” section.
  • the substituent is, for example, an "arbitrary substituent” described later.
  • substituents when the above-mentioned "monocycle” or “condensed ring” has a substituent are the substituents described in the above-mentioned “Substituents described in the present specification” section.
  • the above is the case where "one or more pairs of two or more adjacent pairs are combined with each other to form a substituted or unsubstituted monocycle" and "one or more pairs of two or more adjacent pairs".
  • An unsubstituted alkyl group having 1 to 50 carbon atoms 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, Unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, It is a group selected from the group consisting of an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 and a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.
  • R 901 to R 907 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. If there are two or more R 901s , the two or more R 901s are the same or different from each other. If there are two or more R 902s , the two or more R 902s are the same or different from each other.
  • the two or more R 903s are the same or different from each other. If there are two or more R 904s , the two or more R 904s are the same or different from each other. If there are two or more R 905s , the two or more R 905s are the same or different from each other. If there are two or more R- 906s , the two or more R- 906s are the same or different from each other. When two or more R 907s are present, the two or more R 907s are the same as or different from each other.
  • the substituent in the case of "substituted or unsubstituted” is Alkyl groups with 1 to 50 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 50 ring-forming carbon atoms and a heterocyclic group having 5 to 50 ring-forming atoms.
  • the substituent in the case of "substituted or unsubstituted” is Alkyl groups with 1 to 18 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 18 ring-forming carbon atoms and a heterocyclic group having 5 to 18 ring-forming atoms.
  • any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5 It forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. do.
  • any substituent may further have a substituent.
  • the substituent further possessed by the arbitrary substituent is the same as that of the above-mentioned arbitrary substituent.
  • the numerical range represented by using “AA to BB” has the numerical value AA described before “AA to BB” as the lower limit value and the numerical value BB described after “AA to BB”. Means the range including as the upper limit value.
  • the organic electroluminescence device has the following basic configuration.
  • the organic electroluminescence element includes an anode, a cathode, two or more light emitting units arranged between the anode and the cathode, and a first light emitting unit arranged between the anode and the cathode. It has a cathode side organic layer, and at least one of the two or more light emitting units is a laminated light emitting unit, and the first cathode is on the cathode side of at least one of the laminated light emitting units.
  • a side organic layer is arranged, the first cathode side organic layer contains a phenanthroline compound having a phenanthroline skeleton, and the laminated light emitting unit includes a first light emitting layer and a second light emitting layer, and the first light emitting layer is included.
  • the light emitting layer of the above contains a first host material, the second light emitting layer contains a second host material, and the first host material and the second host material are different from each other.
  • the first light emitting layer contains at least the first light emitting compound exhibiting light emission having a maximum peak wavelength of 500 nm or less, and the second light emitting layer has a second light emitting property exhibiting light emission having a maximum peak wavelength of 500 nm or less.
  • the first luminescent compound and the second luminescent compound contain at least a compound and are the same as or different from each other.
  • the organic EL element according to the present embodiment further includes at least one of the following (element 1) and (element 2) in addition to the above basic configuration.
  • the first host material has the structure of the following condition (i) or the structure of the following condition (ii) in the molecule, and the first benzene ring and the second benzene ring in the biphenyl structure.
  • the benzene ring of the above is further linked by cross-linking at at least one portion other than the single bond, and the second host material is an anthracene derivative.
  • the first benzene ring and the second benzene ring have a biphenyl structure in which they are connected by a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are formed. At least one portion other than the single bond is further linked by cross-linking.
  • a linking structure including a benzene ring and a naphthalene ring linked by a single bond is provided, and the benzene ring and the naphthalene ring in the linking structure each independently further have a monocyclic ring or a condensed ring. Condensed or uncondensed, the benzene ring and the naphthalene ring in the linked structure are further linked by cross-linking at at least one portion other than the single bond.
  • organic EL element including the above-mentioned basic configuration and at least one of (element 1) and (element 2) will be described.
  • an organic electroluminescence device having two or more light emitting units arranged between an anode and a cathode is referred to as a tandem type organic electroluminescence device (tandem type organic EL device).
  • TTA Tripret-Tripret-Anhilation
  • TTA is a mechanism in which triplet excitons and triplet excitons collide with each other to generate singlet excitons.
  • the TTA mechanism may be referred to as a TTF mechanism as described in Patent Document 8.
  • the TTF phenomenon will be described.
  • the holes injected from the anode and the electrons injected from the cathode recombine in the light emitting layer to generate excitons.
  • the spin state has a ratio of 25% for singlet excitons and 75% for triplet excitons, as is conventionally known.
  • 25% of singlet excitons emit light when relaxed to the ground state, but the remaining 75% of triplet excitons do not emit light and are thermally deactivated. It returns to the ground state through the process. Therefore, the theoretical limit value of the internal quantum efficiency of the conventional fluorescent device is said to be 25%.
  • the behavior of triplet excitons generated inside organic matter has been theoretically investigated. S. M. According to Bachilo et al.
  • triplet excitons triplet excitons
  • 1 A represents the ground state
  • 1 A * represents the lowest excited singlet exciton
  • the light emission ratio (TTF ratio) derived from TTF in the total luminous intensity is 15/40, that is, 37.5%.
  • the initially generated triplet excitons collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons)
  • the triplet excitons generated by the recombination of holes and electrons in the first light emitting layer in the laminated light emitting unit are in direct contact with the first light emitting layer. Even if carriers are excessively present at the interface with the organic layer, it is considered that triplet excitons existing at the interface between the first light emitting layer and the organic layer are less likely to be quenched. For example, if the recombination region is locally present at the interface between the first light emitting layer and the hole transport layer or the electron barrier layer, quenching due to excess electrons can be considered.
  • the organic electroluminescence element includes a laminated light emitting unit including at least two light emitting layers (that is, a first light emitting layer and a second light emitting layer) satisfying a predetermined relationship, and the first light emitting layer.
  • a laminated light emitting unit including a first light emitting layer and a second light emitting layer so as to satisfy the relationship of the above formula (Equation 3)
  • triplet excitons generated in the first light emitting layer are caused by excess carriers. It is possible to suppress the movement to the second light emitting layer without being quenched, and the reverse movement from the second light emitting layer to the first light emitting layer. As a result, the TTF mechanism is expressed in the second light emitting layer, singlet excitons are efficiently generated, and the luminous efficiency is improved.
  • the laminated light emitting unit in the organic electroluminescence element utilizes the first light emitting layer that mainly generates triplet excitons and the triplet exciter that has moved from the first light emitting layer to implement the TTF mechanism.
  • the second light emitting layer which is mainly expressed, is provided as a different region, and as the second host material in the second light emitting layer, triplet energy smaller than that of the first host material in the first light emitting layer is provided.
  • the luminescence efficiency is improved by providing a difference in triplet energy by using the compound having.
  • the phenanthroline compound having a phenanthroline skeleton easily generates an electric charge, it can be suitably used as an electron transport material in a so-called tandem type organic EL device provided with a plurality of light emitting units.
  • the phenanthroline compound has low resistance to holes, and when holes move from the light emitting layer to an organic layer containing the phenanthroline compound (for example, an electron transport layer), the phenanthroline compound deteriorates and the device life is reduced. Tends to decrease.
  • the first cathode-side organic layer containing the phenanthroline compound is arranged on the cathode side of the laminated light-emitting unit including the first light-emitting layer and the second light-emitting layer.
  • This laminated light emitting unit mainly expresses the TTF mechanism by utilizing the first light emitting layer that mainly generates triplet excitons and the triplet excitons that have moved from the first light emitting layer. Layers and are provided as different areas.
  • the first cathode-side organic layer containing the easily deteriorated phenanthroline compound and the first light-emitting layer (recombination layer) can be separated from each other, and the laminated light-emitting unit moves to the first cathode-side organic layer. It is considered that the amount of holes is suppressed and the life of the organic EL device is extended.
  • the first cathode-side organic layer is an organic layer arranged on the cathode side of at least one laminated light emitting unit.
  • the first cathode-side organic layer may be referred to as an intermediate layer.
  • the intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, a connector layer, or an intermediate insulating layer.
  • the intermediate layer is a layer that supplies electrons to a layer arranged on the anode side of the intermediate layer and supplies holes to a layer arranged on the cathode side of the intermediate layer.
  • the intermediate layer can be formed of a known material.
  • the intermediate layer may be one layer or may be composed of two or more layers. A unit composed of two or more intermediate layers may be referred to as an intermediate unit.
  • the composition of the plurality of intermediate layers contained in the intermediate unit is the same as or different from each other.
  • a plurality of layers including a light emitting layer arranged between an intermediate layer or an intermediate unit and an anode or a cathode may be referred to as a light emitting unit.
  • Examples of the element configuration of the organic EL element having a plurality of light emitting units include the following element configurations (TND1) to (TND4).
  • TTD1 Anode / First light emitting unit / Intermediate layer / Second light emitting unit / Cathode
  • TTD2 Anode / First light emitting unit / Intermediate unit / Second light emitting unit / Cathode
  • TTD3 Anode / First light emitting unit / Cathode Intermediate layer / Second light emitting unit / Second intermediate layer / Third light emitting unit / Cathode
  • TCD4 Anode / First light emitting unit / First intermediate unit / Second light emitting unit / Second intermediate unit / Third light emitting unit / Cathode
  • the number of light emitting units and intermediate layers (or intermediate units) is not limited to the examples of (TND1) to (TND4) shown here.
  • the first cathode-side organic layer is preferably included as at least one intermediate layer, or is also preferably included as an intermediate layer in at least one of the intermediate units.
  • first light emitting layer and the second light emitting layer are contained in at least one of the first light emitting unit, the second light emitting unit and the third light emitting unit. It is also preferable that the first light emitting layer and the second light emitting layer are included in all the light emitting units of the organic EL element.
  • the light emitting unit arranged on the anode side of the intermediate layer as the first cathode side organic layer or the intermediate unit including the first cathode side organic layer is arranged on the anode side. It is preferable that the light emitting unit is the laminated light emitting unit according to the present embodiment.
  • the laminated light emitting unit of the organic EL element according to the present embodiment may have one or more organic layers in addition to the first light emitting layer and the second light emitting layer.
  • the organic layer include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole barrier layer and an electron barrier layer. Be done.
  • the organic layer of the laminated light emitting unit may be composed of only the first light emitting layer and the second light emitting layer, but for example, a hole injection layer and a hole transport layer. It may further have at least one layer selected from the group consisting of an electron injection layer, an electron transport layer, a hole barrier layer, an electron barrier layer, and the like.
  • the band arranged on the anode side of the light emitting layer in the light emitting unit may be referred to as a hole transport band.
  • the hole transport band may be a single layer or a plurality of layers. Examples of the layer constituting the hole transport zone include a hole injection layer and an electron barrier layer in addition to the hole transport layer.
  • the band arranged on the cathode side of the light emitting layer of the light emitting unit may be referred to as an electron transport band.
  • the electron transport band may be a single layer or a plurality of layers. Examples of the layer constituting the electron transport band include an electron injection layer and a hole barrier layer in addition to the electron transport layer.
  • the organic EL element according to the present embodiment may have a light emitting unit having at least one light emitting layer as a light emitting unit other than the laminated light emitting unit, and the light emitting unit other than the laminated light emitting unit may be other than the light emitting layer.
  • the organic layer for example, even if it has at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer and an electron barrier layer. good.
  • the two or more light emitting units include a laminated light emitting unit and at least one phosphorescent light emitting unit different from the laminated light emitting unit.
  • the phosphorescent unit preferably contains a phosphorescent compound that exhibits phosphorescence.
  • the phosphorescent compound is preferably a metal complex.
  • the metal complex as the phosphorescent compound is preferably an iridium complex, a copper complex, a platinum complex, an osmium complex or a gold complex.
  • the phosphorescent unit preferably has at least one phosphorescent layer containing a phosphorescent compound.
  • the phosphorescent unit may have two or more phosphorescent layers.
  • the phosphorescent unit When the phosphorescent unit has two or more phosphorescent layers, the phosphorescent layers may or may not be in direct contact with each other. Further, the phosphorescent unit preferably has a green phosphorescent layer containing a green-emitting phosphorescent compound and a red phosphorescent layer containing a red-emitting phosphorescent compound.
  • the green emission means the emission in which the maximum peak wavelength of the emission spectrum is in the range of 500 nm or more and 550 nm or less.
  • the red emission means the emission in which the maximum peak wavelength of the emission spectrum is in the range of 600 nm or more and 640 nm or less.
  • the organic EL element according to the present embodiment has a phosphorescent light emitting unit
  • the organic EL element according to the present embodiment has one laminated light emitting unit and one phosphorescent light emitting unit.
  • the organic EL element according to the present embodiment does not include a phosphorescent light emitting unit.
  • FIG. 1 shows a schematic configuration of the organic EL element 1 as an example of the organic EL element according to the present embodiment.
  • the organic EL element 1 is a tandem type organic EL element.
  • the organic EL element 1 includes a substrate 2, a cathode 4, an anode 3, an intermediate unit 20 included between the cathode 4 and the anode 3, and a first light emitting unit 11 included between the intermediate unit 20 and the anode 3. And a second light emitting unit 12 included between the intermediate unit 20 and the cathode 4.
  • the first light emitting unit 11 and the second light emitting unit 12 are connected in series via an intermediate unit 20.
  • the organic EL element 1 includes a first light emitting unit 11 and a second light emitting unit 12 as two light emitting units.
  • the first light emitting unit 11 and the second light emitting unit 12 in the organic EL element 1 are both laminated light emitting units according to the present embodiment.
  • the first light emitting unit 11 may be referred to as a first laminated light emitting unit.
  • the second light emitting unit 12 may be referred to as a second laminated light emitting unit.
  • the hole injection layer 113, the hole transport layer 114, the first light emitting layer 111, the second light emitting layer 112, and the electron transport layer 115 are laminated in this order from the anode 3 side. It is composed of.
  • the hole transport layer 123, the first light emitting layer 121, the second light emitting layer 122, the electron transport layer 124, and the electron injection layer 125 are laminated in this order from the anode 3 side. It is composed.
  • the intermediate unit 20 is configured by laminating the first cathode side organic layer 21 (sometimes referred to as the first N layer) and the first P layer 22 in this order in order from the anode 3 side.
  • the present invention is not limited to the configuration of the organic EL element shown in FIG.
  • an organic EL element having another configuration for example, in a light emitting unit, an embodiment in which a second light emitting layer and a first light emitting layer are laminated in this order from the anode side can be mentioned.
  • the number of light emitting units and intermediate units is not limited to the configuration of the organic EL element shown in FIG.
  • there is also an embodiment in which the first cathode-side organic layer as an intermediate layer is arranged between the first light emitting unit and the second light emitting unit instead of the intermediate unit.
  • the organic EL element according to this embodiment may be a bottom emission type organic EL element. Further, the organic EL element according to the present embodiment may be a top emission type organic EL element.
  • the following element configurations (TND5) to (TND8) can be mentioned.
  • (TND5) anode / first light emitting unit (laminated light emitting unit) / intermediate layer / second light emitting unit (phosphorescent light emitting unit) / cathode (TND6) anode / first light emitting unit (laminated light emitting unit) / intermediate unit / second light emitting Unit (phosphorescent unit) / cathode
  • TCD7 anode / first light emitting unit (laminated light emitting unit) / first intermediate layer / second light emitting unit (phosphorescent light emitting unit) / second intermediate layer / third light emitting unit (laminated light emitting unit) Unit) / cathode (TND8) anode / first light emitting unit (laminated light emitting unit) / first
  • the first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton.
  • the first cathode-side organic layer preferably contains a phenanthroline compound and an electron-donating material.
  • the electron donating material is preferably at least one selected from the group consisting of elemental metals, metal compounds and metal complexes having electron donating properties. Specific examples of the electron donating material include alkali metals, alkali metal compounds, organic metal complexes containing alkali metals, alkaline earth metals, alkaline earth metal compounds, organic metal complexes containing alkaline earth metals, and rare earth metals.
  • the first cathode-side organic layer preferably contains a phenanthroline compound and at least one metal selected from the group consisting of Li, Yb and Cs.
  • the organic EL element according to the present embodiment may include an intermediate unit between the light emitting units.
  • the intermediate unit contains a plurality of organic layers.
  • the first cathode-side organic layer may be an organic layer constituting an intermediate unit.
  • an intermediate unit is arranged on the cathode side of at least one laminated light emitting unit, and the intermediate unit includes a first cathode side organic layer.
  • the intermediate unit preferably includes at least one N layer and at least one P layer.
  • the N layer is arranged on the anode side of the P layer.
  • the intermediate unit preferably includes the first cathode side organic layer as the N layer.
  • the intermediate unit may have a first N layer arranged on the anode side and a second N layer arranged on the cathode side of the first N layer as a plurality of N layers.
  • the first cathode-side organic layer may be the first N layer or the second N layer. If the second N layer is the first cathode-side organic layer, the first cathode-side organic layer and the first light-emitting layer can be easily separated from each other.
  • the N layer preferably contains a ⁇ -electron-deficient compound and an electron-donating material. Examples of the ⁇ -electron-deficient compound include a compound capable of coordinating with a metal atom.
  • the ⁇ -electron-deficient compound examples include a phenanthroline-based compound, a benzimidazole-based compound, an azine-based compound, and quinolinol.
  • the P layer is a layer containing an acceptor material.
  • the P layer may be a layer to which the acceptor material is doped (P-doped layer).
  • the acceptor material can also be appropriately selected and used from the "substances having high hole injection properties" exemplified in the section of the hole injection layer.
  • the organic EL device according to the present embodiment may have a configuration in which a second cathode side organic layer is arranged between the first light emitting layer and the first cathode side organic layer.
  • the organic EL device according to the present embodiment has a second light emitting layer, a first light emitting layer, a second cathode side organic layer, and a first cathode side organic layer in this order from the anode side. You may. In this way, when the second light emitting layer and the first light emitting layer are provided in this order from the anode side, the first light emitting layer and the first cathode side are provided by the second cathode side organic layer. It can be separated from the organic layer.
  • the first light emitting layer, the second light emitting layer, the second cathode side organic layer, and the first cathode side organic layer are provided in this order from the anode side. You may be doing it.
  • the first light emitting layer and the second light emitting layer are provided in this order from the anode side, the first light emitting layer and phenanthroline are provided even if the second cathode side organic layer is not arranged. It can be separated from the first cathode-side organic layer containing the compound.
  • the second cathode-side organic layer does not contain a phenanthroline compound having a phenanthroline skeleton.
  • the second cathode-side organic layer may be an N layer different from the first cathode-side organic layer in the intermediate unit.
  • the second cathode-side organic layer may be the first N-layer
  • the first cathode-side organic layer may be the second N-layer.
  • the second cathode-side organic layer may be an electron transport layer or a hole barrier layer in the light emitting unit.
  • the first light emitting layer and the first cathode side organic layer are separated by 30 nm or more.
  • the first cathode side organic layer and the first light emitting layer are separated by 30 nm or more, it becomes easy to suppress the amount of holes moving from the laminated light emitting unit to the first cathode side organic layer, and the organic EL It is considered that the life of the element is likely to be extended.
  • At least one light emitting unit may be arranged between the first cathode side organic layer and the cathode.
  • the first cathode-side organic layer containing the phenanthroline compound may be arranged between the laminated light emitting unit and another light emitting unit different from the laminated light emitting unit.
  • the organic layer containing the phenanthroline compound When the organic layer containing the phenanthroline compound is arranged at a position where it is easily received electron injection from the cathode (for example, when it is in direct contact with the cathode or the electron injection layer), the organic layer containing the phenanthroline compound may be used. Since it is susceptible to electron injection, deterioration due to injection of holes that have moved from the light emitting layer is alleviated. On the other hand, when the organic layer containing the phenanthroline compound is arranged between the light emitting units and cannot be activated by the cathode (metal electrode) and is difficult to receive electron injection, the phenanthroline compound is a hole. Prone to deterioration.
  • the first cathode-side organic layer containing the phenanthroline compound is arranged between the light emitting units and it is difficult to receive electron injection, the first cathode Since the laminated light emitting unit is arranged on the anode side of the side organic layer, it is considered that the amount of holes moving from the laminated light emitting unit to the first cathode side organic layer is suppressed and the life of the organic EL element is extended.
  • the organic layer containing the phenanthroline compound may be arranged on the cathode side of the two or more light emitting units, which is arranged on the most cathode side. However, it does not have to be arranged.
  • the organic EL element according to the present embodiment includes two or more light emitting units. Each light emitting unit includes a light emitting layer.
  • the organic EL element according to the present embodiment includes at least one laminated light emitting unit, and the laminated light emitting unit includes a first light emitting layer and a second light emitting layer as described above.
  • the organic EL element according to the present embodiment may include two or more laminated light emitting units. Other light emitting units that are not laminated light emitting units may include a single light emitting layer or may include a plurality of light emitting layers.
  • the second light emitting layer of the laminated light emitting unit is arranged between the first light emitting layer and the first cathode side organic layer. Since the second light emitting layer is arranged between the first light emitting layer as the recombination layer and the first cathode side organic layer containing the phenanthroline compound, the first light emitting layer and the first cathode side are arranged. Even when no other organic layer is arranged between the organic layer, the first light emitting layer and the first cathode side organic layer can be separated from each other by the second light emitting layer.
  • the first light emitting layer of the laminated light emitting unit is arranged between the second light emitting layer and the first cathode side organic layer.
  • the organic EL device may have the first light emitting layer and the second light emitting layer in this order from the anode side, or the second light emitting layer and the first light emitting layer from the anode side.
  • the light emitting layers of the above may be provided in this order. Regardless of the order of the first light emitting layer and the second light emitting layer, the effect of having the light emitting layer in a laminated structure is expected by selecting the combination of materials satisfying the relationship of the above formula (Equation 3). can.
  • the first host material and the second host material satisfy the relationship of the following mathematical formula (Equation 31) deterioration of the phenanthroline compound can be further suppressed.
  • Equation 32 When the first host material and the second host material satisfy the relationship of the following mathematical formula (Equation 32), deterioration of the phenanthroline compound can be further suppressed.
  • the first host material and the second host material satisfy the relationship of the following mathematical formula (Equation 33)
  • the recombination ability of holes and electrons in the first light emitting layer is improved.
  • the electron mobility can be measured by measuring the impedance using the mobility evaluation element manufactured by the following procedure.
  • the mobility evaluation element is manufactured, for example, by the following procedure.
  • the following compound ET-A is vapor-deposited on the measurement target layer to form an electron transport layer.
  • LiF is vapor-deposited on the film of the electron transport layer to form an electron injection layer.
  • Metallic aluminum (Al) is vapor-deposited on the film formation of the electron injection layer to form a metal cathode.
  • the above-mentioned element configuration for mobility evaluation is shown in abbreviated form as follows. glass / Al (50) / Target (200) / ET-A (10) / LiF (1) / Al (50)
  • the numbers in parentheses indicate the film thickness (nm).
  • the electrical time constant ⁇ of the mobility evaluation element is obtained from the following formula (C2) from the frequency fmax indicating the peak.
  • Calculation formula (C2): ⁇ 1 / (2 ⁇ fmax) ⁇ in the above formula (C2) is a symbol representing the pi.
  • the electron mobility ⁇ e is calculated from the relationship of the following calculation formula (C3-1).
  • the hole mobility can be measured by measuring the impedance using the mobility evaluation element manufactured by the following procedure.
  • the mobility evaluation element is manufactured, for example, by the following procedure.
  • the following compound HA-2 is vapor-deposited on a glass substrate with an ITO transparent electrode (anode) so as to cover the transparent electrode to form a hole injection layer.
  • the following compound HT-A is vapor-deposited on the film formation of the hole injection layer to form a hole transport layer.
  • the compound Target to be measured for the hole mobility is vapor-deposited to form a layer to be measured.
  • Metallic aluminum (Al) is vapor-deposited on the measurement target layer to form a metal cathode.
  • the above-mentioned element configuration for mobility evaluation is shown in abbreviated form as follows. ITO (130) / HA-2 (5) / HT-A (10) / Target (200) / Al (80)
  • the numbers in parentheses indicate the film thickness (nm).
  • An element for evaluating the mobility of holes is installed in an impedance measuring device to measure impedance. Impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At that time, a DC voltage V is applied to the element at the same time as the AC amplitude 0.1 V. From the measured impedance Z, the modulus M is calculated using the relationship of the above calculation formula (C1). In the board plot with the imaginary part of the modulus M on the vertical axis and the frequency [Hz] on the horizontal axis, the electrical time constant ⁇ of the mobility evaluation element is obtained from the above calculation formula (C2) from the frequency fmax indicating the peak.
  • the hole mobility ⁇ h is calculated from the relationship of the following formula (C3-2).
  • the square root E 1/2 of the electric field strength can be calculated from the relationship of the following formula (C4).
  • Calculation formula (C4): E 1/2 V 1/2 / d 1/2
  • a Solartron 1260 type is used as an impedance measuring device, and for higher accuracy, a Solartron 1296 type dielectric constant measurement interface can be used together.
  • the triplet energy T 1 (H1) of the first host material and the triplet energy T 1 (H2) of the second host material are related by the following mathematical formula (Equation 5). It is preferable to satisfy. T 1 (H1) -T 1 (H2)> 0.03 eV ... (Equation 5)
  • the first light emitting layer contains the first host material.
  • the first host material is a compound different from the second host material contained in the second light emitting layer.
  • the first light emitting layer contains at least the first light emitting compound exhibiting light emission having a maximum peak wavelength of 500 nm or less.
  • the first luminescent compound is preferably a fluorescent compound exhibiting fluorescence emission having a maximum peak wavelength of 500 nm or less.
  • the first luminescent compound is preferably a compound that does not contain an azine ring structure in the molecule.
  • the first luminescent compound is preferably not a boron-containing complex, and more preferably the first luminescent compound is not a complex.
  • the first light emitting layer does not contain a metal complex. Further, in the organic EL device according to the present embodiment, it is also preferable that the first light emitting layer does not contain a boron-containing complex.
  • the first light emitting layer does not contain a phosphorescent material (dopant material). Further, it is preferable that the first light emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex.
  • the heavy metal complex include an iridium complex, an osmium complex, a platinum complex, and the like.
  • the peak having the maximum emission intensity when the peak having the maximum emission intensity is set as the maximum peak and the height of the maximum peak is set to 1, the heights of other peaks appearing in the emission spectrum are 0. It is preferably less than 6.
  • the peak in the emission spectrum is a maximum value. Further, in the emission spectrum of the first luminescent compound, the number of peaks is preferably less than three.
  • the first light emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the device is driven.
  • the maximum peak wavelength of the light emitted by the light emitting layer when the device is driven can be measured by the method described below.
  • ⁇ p 1 of the light emitted from the first light emitting layer when driving the element For the maximum peak wavelength ⁇ p 1 of the light emitted from the first light emitting layer when the element is driven, an organic EL element is manufactured by using the same material as the first light emitting layer for the second light emitting layer, and the current of the organic EL element is obtained.
  • the spectral radiance spectrum when a voltage is applied to the element so that the density is 10 mA / cm 2 is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta Co., Ltd.).
  • the maximum peak wavelength ⁇ p 1 (unit: nm) is calculated from the obtained spectral radiance spectrum.
  • an organic EL element is manufactured by using the same material as the second light emitting layer for the first light emitting layer, and the current of the organic EL element is obtained.
  • the spectral radiance spectrum when a voltage is applied to the element so that the density is 10 mA / cm 2 is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta Co., Ltd.).
  • the maximum peak wavelength ⁇ p 2 (unit: nm) is calculated from the obtained spectral radiance spectrum.
  • the singlet energy S 1 (H1) of the first host material and the singlet energy S 1 (D1) of the first luminescent compound are represented by the following mathematical formula (Equation 20). It is preferable to satisfy the relationship. S 1 (H1)> S 1 (D1) ... (Equation 20)
  • the singlet energy S 1 means the energy difference between the lowest excited singlet state and the ground state.
  • the singlet excitons generated on the first host material are the first from the first host material. It facilitates energy transfer to one luminescent compound and contributes to the fluorescence emission of the first luminescent compound.
  • the triplet energy T 1 (H1) of the first host material and the triplet energy T 1 (D1) of the first luminescent compound are represented by the following mathematical formula (Equation 20A). It is preferable to satisfy the relationship. T 1 (D1)> T 1 (H1) ... (Equation 20A)
  • the triplet excitons generated in the first light emitting layer have a higher triplet energy. Since it moves on the first host material instead of one luminescent compound, it easily moves to the second light emitting layer.
  • the organic EL device according to the present embodiment preferably satisfies the relationship of the following mathematical formula (Equation 20B).
  • the first light emitting compound is preferably contained in the first light emitting layer in an amount of more than 1.1% by mass. That is, the first light emitting layer preferably contains the first light emitting compound in an amount of more than 1.1% by mass of the total mass of the first light emitting layer, and 1. It is more preferably contained in an amount of 2% by mass or more, and further preferably contained in an amount of 1.5% by mass or more based on the total mass of the first light emitting layer.
  • the first light emitting layer preferably contains the first light emitting compound in an amount of 10% by mass or less of the total mass of the first light emitting layer, and preferably contains 7% by mass or less of the total mass of the first light emitting layer. It is more preferable to contain 5% by mass or less of the total mass of the first light emitting layer.
  • the first light emitting layer preferably contains the first compound as the first host material in an amount of 60% by mass or more of the total mass of the first light emitting layer. It is more preferable to contain 70% by mass or more of the total mass of the first light emitting layer, further preferably 80% by mass or more of the total mass of the first light emitting layer, and the total mass of the first light emitting layer. It is more preferably contained in an amount of 90% by mass or more, and even more preferably 95% by mass or more based on the total mass of the first light emitting layer.
  • the first light emitting layer preferably contains the first host material in an amount of 99% by mass or less of the total mass of the first light emitting layer. However, when the first light emitting layer contains the first host material and the first luminescent compound, the upper limit of the total content of the first host material and the first luminescent compound is 100% by mass. be.
  • the present embodiment does not exclude that the first light emitting layer contains a material other than the first host material and the first light emitting compound.
  • the first light emitting layer may contain only one kind of the first host material, or may contain two or more kinds.
  • the first light emitting layer may contain only one kind of the first light emitting compound, or may contain two or more kinds.
  • the film thickness of the first light emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. When the film thickness of the first light emitting layer is 3 nm or more, the film thickness is sufficient to cause recombination of holes and electrons in the first light emitting layer. In the organic EL device according to the present embodiment, the film thickness of the first light emitting layer is preferably 15 nm or less, and more preferably 10 nm or less. When the film thickness of the first light emitting layer is 15 nm or less, the film thickness is sufficiently thin for the triplet excitons to move to the second light emitting layer. In the organic EL device according to the present embodiment, the film thickness of the first light emitting layer is more preferably 3 nm or more and 15 nm or less.
  • the second light emitting layer contains a second host material.
  • the second host material is a compound different from the first host material contained in the first light emitting layer.
  • the second light emitting layer contains at least a second light emitting compound that emits light having a maximum peak wavelength of 500 nm or less.
  • the second luminescent compound is preferably a fluorescent compound exhibiting fluorescence emission having a maximum peak wavelength of 500 nm or less. The method for measuring the maximum peak wavelength of the compound is as described above.
  • the second light emitting layer emits light having a maximum peak wavelength of 500 nm or less when the device is driven.
  • the half width of the maximum peak of the second luminescent compound is preferably 1 nm or more and 20 nm or less.
  • the Stokes shift of the second luminescent compound preferably exceeds 7 nm. If the Stokes shift of the second luminescent compound exceeds 7 nm, it becomes easy to prevent a decrease in luminous efficiency due to self-absorption. Self-absorption is a phenomenon in which the same compound absorbs the emitted light, which causes a decrease in luminous efficiency. Since self-absorption is prominently observed in compounds with a small Stokes shift (that is, a large overlap between the absorption spectrum and the fluorescence spectrum), a large Stokes shift (overlap between the absorption spectrum and the fluorescence spectrum) is required to suppress self-absorption. It is preferable to use a compound (small).
  • the Stokes shift can be measured by the method described below.
  • the compound to be measured is dissolved in toluene at a concentration of 2.0 ⁇ 10-5 mol / L to prepare a sample for measurement.
  • the measurement sample placed in the quartz cell is irradiated with continuous light in the ultraviolet-visible region at room temperature (300 K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured.
  • a spectrophotometer can be used for the absorption spectrum measurement, and for example, a spectrophotometer U-3900 / 3900H type manufactured by Hitachi High-Tech Science Co., Ltd. can be used.
  • the compound to be measured is dissolved in toluene at a concentration of 4.9 ⁇ 10-6 mol / L to prepare a sample for measurement.
  • the measurement sample placed in the quartz cell was irradiated with excitation light at room temperature (300 K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) was measured.
  • a spectrophotometer can be used for the fluorescence spectrum measurement, and for example, a spectrofluorometer F-7000 manufactured by Hitachi High-Tech Science Co., Ltd. can be used. From these absorption spectra and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength is calculated to obtain a Stokes shift (SS).
  • the unit of Stokes shift SS is nm.
  • the triplet energy T 1 (D2) of the second luminescent compound and the triplet energy T 1 (H2) of the second host material are calculated by the following mathematical formula (Equation 3A). It is preferable to satisfy the relationship. T 1 (D2)> T 1 (H2) ... (Equation 3A)
  • the triplet excitation generated in the first light emitting layer by satisfying the relationship of the above formula (Equation 3A) between the second luminescent compound and the second host material.
  • the energy is transferred to the molecule of the second host material instead of the second luminescent compound having higher triplet energy.
  • triplet excitons generated by recombination of holes and electrons on the second host material do not move to the second luminescent compound with higher triplet energy.
  • the triplet excitons generated by recombination on the molecule of the second luminescent compound rapidly transfer energy to the molecule of the second host material.
  • the singlet energy S 1 (H2) of the second host material and the singlet energy S 1 (D2) of the second luminescent compound are represented by the following mathematical formula (Equation 4). It is preferable to satisfy the relationship. S 1 (H2)> S 1 (D2) ... (Equation 4)
  • the singlet energy of the second luminescent compound is increased by satisfying the relationship of the above formula (Equation 4) between the second luminescent compound and the second host material. Since it is smaller than the singlet energy of the second host material, the singlet exciter generated by the TTF phenomenon transfers energy from the second host material to the second luminescent compound, and the energy of the second luminescent compound is transferred. Contributes to fluorescent emission.
  • the second luminescent compound is preferably a compound that does not contain an azine ring structure in the molecule.
  • the second luminescent compound is preferably not a boron-containing complex, and more preferably the second luminescent compound is not a complex.
  • the second light emitting layer does not contain a metal complex. Further, in the organic EL device according to the present embodiment, it is also preferable that the second light emitting layer does not contain a boron-containing complex.
  • the second light emitting layer does not contain a phosphorescent material (dopant material). Further, it is preferable that the second light emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex.
  • the heavy metal complex include an iridium complex, an osmium complex, a platinum complex, and the like.
  • the second light emitting compound is preferably contained in the second light emitting layer in an amount of more than 1.1% by mass. That is, the second light emitting layer preferably contains the second light emitting compound in an amount of more than 1.1% by mass of the total mass of the second light emitting layer, and 1. It is more preferably contained in an amount of 2% by mass or more, and further preferably contained in an amount of 1.5% by mass or more based on the total mass of the second light emitting layer.
  • the second light emitting layer preferably contains the second light emitting compound in an amount of 10% by mass or less of the total mass of the second light emitting layer, and preferably contains 7% by mass or less of the total mass of the second light emitting layer. It is more preferable to contain 5% by mass or less of the total mass of the second light emitting layer.
  • the second light emitting layer preferably contains the second compound as the second host material in an amount of 60% by mass or more of the total mass of the second light emitting layer, and is 70 of the total mass of the second light emitting layer. It is more preferably contained in an amount of mass% or more, more preferably 80% by mass or more of the total mass of the second light emitting layer, and further preferably 90% by mass or more of the total mass of the second light emitting layer. Even more preferably, it is contained in an amount of 95% by mass or more based on the total mass of the second light emitting layer.
  • the second light emitting layer preferably contains the second host material in an amount of 99% by mass or less of the total mass of the second light emitting layer. When the second light emitting layer contains the second host material and the second luminescent compound, the upper limit of the total content of the second host material and the second luminescent compound is 100% by mass.
  • the present embodiment does not exclude that the second light emitting layer contains a material other than the second host material and the second light emitting compound.
  • the second light emitting layer may contain only one type of second host material, or may contain two or more types of the second host material.
  • the second light emitting layer may contain only one kind of the second light emitting compound, or may contain two or more kinds.
  • the film thickness of the second light emitting layer is preferably 5 nm or more, more preferably 15 nm or more.
  • the film thickness of the second light emitting layer is 5 nm or more, it is easy to prevent the triplet excitons that have moved from the first light emitting layer to the second light emitting layer from returning to the first light emitting layer again.
  • the film thickness of the second light emitting layer is 5 nm or more, triplet excitons can be charged and separated from the recombination portion in the first light emitting layer.
  • the film thickness of the second light emitting layer is preferably 25 nm or less, more preferably 20 nm or less.
  • the film thickness of the second light emitting layer is 25 nm or less, the density of triplet excitons in the second light emitting layer can be improved to make the TTF phenomenon more likely to occur.
  • the film thickness of the second light emitting layer is preferably 5 nm or more and 25 nm or less.
  • the triplet energy T 1 (D1) of the first luminescent compound preferably satisfies the relationship of the following mathematical formula (Equation 10A). 2.6 eV> T 1 (D1)> T 1 (H1)> T 1 (H2) ... (Equation 10A)
  • the triplet energy T 1 (D2) of the second luminescent compound preferably satisfies the relationship of the following mathematical formula (Equation 10B). 2.6 eV> T 1 (D2)> T 1 (H1)> T 1 (H2) ... (Equation 10B)
  • the triplet energy T 1 (DX) of the first luminescent compound or the second luminescent compound and the triplet energy T 1 (H1) of the first host material are present.
  • the triplet energy T 1 (D1) of the first luminescent compound preferably satisfies the relationship of the following mathematical formula (Equation 11A). 0 eV ⁇ T 1 (D1) -T 1 (H1) ⁇ 0.6 eV ... (Equation 11A)
  • the triplet energy T 1 (D2) of the second luminescent compound preferably satisfies the relationship of the following mathematical formula (Equation 11B). 0eV ⁇ T 1 (D2) -T 1 (H2) ⁇ 0.8 eV ... (Equation 11B)
  • the triplet energy T 1 (H1) of the first host material satisfies the relationship of the following mathematical formula (Equation 12).
  • the triplet energy T 1 (H1) of the first host material preferably satisfies the relationship of the following mathematical formula (Equation 12A), and satisfies the relationship of the following mathematical formula (Equation 12B). It is also preferable. T 1 (H1)> 2.10 eV ... (Equation 12A) T 1 (H1)> 2.15 eV ... (Equation 12B)
  • the triplet energy T 1 (H1) of the first host material satisfies the relationship of the mathematical formula (Equation 12A) or the equation (Equation 12B), so that the first light emission occurs.
  • the triplet excitons generated in the layer are likely to move to the second light emitting layer, and are also easy to suppress the reverse movement from the second light emitting layer to the first light emitting layer. As a result, singlet excitons are efficiently generated in the second light emitting layer, and the luminous efficiency is improved.
  • the triplet energy T 1 (H1) of the first host material preferably satisfies the relationship of the following mathematical formula (Equation 12C), and satisfies the relationship of the following mathematical formula (Equation 12D). It is also preferable. 2.08eV> T 1 (H1)> 1.87eV ... (Equation 12C) 2.05 eV> T 1 (H1)> 1.90 eV ... (Equation 12D)
  • the triplet energy T 1 (H1) of the first host material satisfies the relationship of the mathematical formula (Equation 12C) or the equation (Equation 12D), so that the first light emission occurs.
  • the energy of the triplet excitons generated in the layer is reduced, and the life of the organic EL element can be expected to be extended.
  • the triplet energy T 1 (D1) of the first luminescent compound satisfies the relationship of the following mathematical formula (Equation 14A), and the relationship of the following mathematical formula (Equation 14B) is satisfied. It is also preferable to satisfy. 2.60eV> T 1 (D1) ... (Equation 14A) 2.50eV> T 1 (D1) ... (Equation 14B)
  • the first light emitting layer contains the first light emitting compound satisfying the relationship of the above formula (Equation 14A) or (Equation 14B)
  • the life of the organic EL device is extended.
  • the triplet energy T 1 (D2) of the second luminescent compound satisfies the relationship of the following mathematical formula (Equation 14C), and the relationship of the following mathematical formula (Equation 14D) is satisfied. It is also preferable to satisfy. 2.60eV> T 1 (D2) ... (Equation 14C) 2.50eV> T 1 (D2) ... (Equation 14D)
  • the second light emitting layer contains a compound satisfying the relationship of the above formula (Equation 14C) or (Equation 14D)
  • the life of the organic EL device is extended.
  • the triplet energy T 1 (H2) of the second host material satisfies the relationship of the following mathematical formula (Equation 13).
  • the organic EL device may further include a third light emitting layer.
  • the third light emitting layer contains the third host material, and the first host material, the second host material, and the third host material are different from each other, and the third light emitting layer has a maximum peak wavelength of 500 nm.
  • the first luminescent compound, the second luminescent compound, and the third luminescent compound contain at least a third luminescent compound exhibiting the following luminescence, and the third luminescent compound is the same as or different from each other. It is preferable that the triplet energy T 1 (H1) of one host material and the triplet energy T 1 (H3) of the third host material satisfy the relationship of the following formula (Equation 1A). T 1 (H1)> T 1 (H3) ... (Equation 1A)
  • the organic EL element according to the present embodiment includes the third light emitting layer
  • the triplet energy T 1 (H2) of the second host material and the triplet energy T 1 (H3) of the third host material are used.
  • the first light emitting layer and the second light emitting layer are in direct contact with each other.
  • the layer structure in which the first light emitting layer and the second light emitting layer are in direct contact with each other is, for example, any one of the following aspects (LS1), (LS2) and (LS3). Aspects may also be included.
  • (LS1) In the process of vapor deposition of the compound related to the first light emitting layer and the step of vapor deposition of the compound related to the second light emitting layer, there is a region where both the first host material and the second host material coexist. A mode in which the region is generated and exists at the interface between the first light emitting layer and the second light emitting layer.
  • LS2 When the first light emitting layer and the second light emitting layer contain a luminescent compound, the step of depositing the compound related to the first light emitting layer and the step of vaporizing the compound related to the second light emitting layer are performed.
  • LS3 When the first light emitting layer and the second light emitting layer contain a luminescent compound, the step of depositing the compound related to the first light emitting layer and the step of vaporizing the compound related to the second light emitting layer are performed.
  • a region composed of the luminescent compound, a region composed of the first host material, or a region composed of the second host material is generated, and the region is the interface between the first light emitting layer and the second light emitting layer.
  • the organic EL element according to the present embodiment includes a third light emitting layer
  • the first light emitting layer and the second light emitting layer are in direct contact with each other
  • the second light emitting layer and the third light emitting layer are in direct contact with each other. It is preferable that the layers are in direct contact with each other.
  • the layer structure in which the second light emitting layer and the third light emitting layer are in direct contact with each other is, for example, any one of the following aspects (LS4), (LS5) and (LS6). Aspects may also be included.
  • (LS4) In the process of vapor deposition of the compound related to the second light emitting layer and the step of vapor deposition of the compound related to the third light emitting layer, there is a region where both the second host material and the third host material coexist. A mode in which the region is generated and exists at the interface between the second light emitting layer and the third light emitting layer.
  • LS5 When the second light emitting layer and the third light emitting layer contain a luminescent compound, the step of depositing the compound related to the second light emitting layer and the step of vaporizing the compound related to the third light emitting layer are performed.
  • LS6 When the second light emitting layer and the third light emitting layer contain a luminescent compound, the step of depositing the compound related to the second light emitting layer and the step of depositing the compound related to the third light emitting layer are performed.
  • a region made of the luminescent compound, a region made of the second host material, or a region made of the third host material is generated, and the region is the interface between the second light emitting layer and the third light emitting layer.
  • the second light emitting layer containing the second compound represented by the above as the second host material may be in direct contact with the second light emitting layer.
  • the laminated light emitting unit of the organic EL element according to the present embodiment is arranged between the organic layers and further has a layer (sometimes referred to as an intervening layer) containing no light emitting compound.
  • the layer (intervening layer) that does not contain a luminescent compound is a first light emitting layer and a second light emitting layer. It is preferably arranged between the light emitting layer and the light emitting layer.
  • the intervening layer preferably does not contain metal atoms.
  • the intervening layer contains an organic material.
  • the organic material contained in the interposition layer is preferably not a luminescent compound.
  • Examples of the organic material contained in the interposition layer include 1) a heterocyclic compound such as an oxadiazole derivative, a benzoimidazole derivative, or a phenanthroline derivative, and 2) a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative.
  • aromatic amine compounds such as 3) triarylamine derivatives and condensed polycyclic aromatic amine derivatives.
  • the organic material contained in the intervening layer may be one or both host materials of the first host material contained in the first light emitting layer and the second host material contained in the second light emitting layer.
  • the content of each organic material is preferably 10% by mass or more of the total mass of the intervening layer.
  • the intervening layer preferably contains the organic material in an amount of 60% by mass or more, more preferably 70% by mass or more, based on the total mass of the intervening layer, and more preferably 70% by mass or more, based on the total mass of the intervening layer. It is more preferably contained in an amount of 80% by mass or more, more preferably 90% by mass or more of the total mass of the intervening layer, and even more preferably 95% by mass or more of the total mass of the intervening layer.
  • the interposition layer may contain only one type of organic material, or may contain two or more types. When the intervening layer contains two or more kinds of organic materials, the upper limit of the total content of the two or more kinds of organic materials is 100% by mass. In addition, this embodiment does not exclude that the intervening layer contains a material other than the organic material.
  • the intervening layer may be composed of a single layer, or may be composed of two or more layers laminated.
  • the film thickness of the intervening layer is not particularly limited, but is preferably 3 nm or more and 15 nm or less, and more preferably 5 nm or more and 10 nm or less per layer.
  • the groups described as "substituted or unsubstituted” are preferably "unsubstituted” groups.
  • the "host material” is, for example, a material contained in "50% by mass or more of the layer". Therefore, for example, the first light emitting layer contains the first compound represented by the following general formula (1) in an amount of 50% by mass or more of the total mass of the first light emitting layer.
  • the second light emitting layer contains, for example, a second compound represented by the following general formula (2) in an amount of 50% by mass or more of the total mass of the second light emitting layer.
  • the phenanthroline compound preferably has at least one group represented by the following general formula (21) and is represented by the following general formula (20).
  • X 21 to X 28 are carbon atoms that independently bond with a nitrogen atom, CR 21 , or a group represented by the general formula (21). At least one of X 21 to X 28 is a carbon atom bonded to a group represented by the general formula (21).
  • the plurality of groups represented by the general formula (21) are the same or different from each other.
  • R 21s consisting of two or more adjacent ones Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other
  • the R 21s that do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring are independent of each other.
  • Ar 2 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • L 2 is a single bond or linking group L 2 as a linking group
  • the aromatic hydrocarbon ring group and the heterocyclic group constituting the plurality of linking groups are the same or different from each other, and adjacent groups are bonded to each other to form a ring or are not bonded to each other.
  • Ar 2 and L 2 as a linking group bond with each other to form a ring, or do not bond with each other.
  • L 2 as a linking group and any of the carbon atoms X 21 to X 28 adjacent to the carbon atom bonded to L 2 or R 21 of CR 21 are bonded to each other to form a ring or to each other.
  • * In the general formula (21) indicates the bonding position with the ring represented by the general formula (20).
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 respectively.
  • R 901 there are a plurality, a plurality of R 901 is the same or different from each other
  • R 902 there are a plurality a plurality of R 902 is the same or different from each other
  • R 903 there are a plurality a plurality of R 903 is the same or different from each other
  • R 904 there are a plurality a plurality of R 904 is the same or different from each other
  • R 905 there are a plurality, a plurality of R 905 is the same or different from each other
  • R 906 there are a plurality, a plurality of R 906 is the same or different from each other
  • R 907 there are a plurality a plurality of R 907 is the same or different from each other
  • R 931 there are a plurality a plurality of R 931 is the same or different from each other
  • R 932 there are a plurality a plurality of R 932 is the same or different from each other
  • the group represented by —O— (R 904 ) is a hydroxy group when R 904 is a hydrogen atom.
  • the group represented by —S— (R 905 ) is a thiol group when R 905 is a hydrogen atom.
  • the group represented by -B (R 934 ) (R 935 ) is a substituted boryl group when R 934 and R 935 are substituents.
  • R 936 and R 937 are substituents
  • a substituted phosphine oxide group R 936 and R 937 is In the case of an aryl group, it is an arylphosphoryl group.
  • the carbon number of the "unsubstituted linear, branched or cyclic polyvalent aliphatic hydrocarbon group" described herein is 1 to 50, unless otherwise stated herein. It is preferably 1 to 20, and more preferably 1 to 6.
  • the ring-forming carbon number of the "unsubstituted polyvalent aromatic hydrocarbon group” described herein is 6 to 50, preferably 6 to 30. More preferably, it is 6 to 18.
  • the number of ring-forming atoms of the "unsubstituted polyvalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, and more preferably 5. ⁇ 18.
  • the heterocyclic group having 5 to 50 ring-forming atoms in Ar 2 of the general formula (21) preferably contains a substituted or unsubstituted group derived from the ring structure represented by the general formula (20). ..
  • X 21 and X 28 of the general formula (20) are carbon atoms bonded to the group represented by the general formula (21).
  • One of X 21 and X 28 of the general formula (20) is a carbon atom bonded to a group represented by the general formula (21), and the other of X 21 and X 28 is a carbon bonded to a hydrogen atom. It is also preferable that it is an atom.
  • X 21 to X 28 of the general formula (20) are carbon atoms that are independently bonded to CR 21 or a group represented by the general formula (21).
  • CR 21 is preferable except for the carbon atom bonded to the group represented by the general formula (21). That is, the compound represented by the general formula (20) is preferably a 1,10-phenanthroline derivative.
  • Ar 2 of the general formula (21) is a substituted or unsubstituted ring-forming condensed aromatic hydrocarbon group having 8 to 20 carbon atoms.
  • Condensed aromatic hydrocarbon groups having 8 to 20 ring-forming carbon atoms include, for example, naphthalene, anthracene, acephenanthrene, aceanthrene, benzoanthracene, triphenylene, pyrene, chrysene, naphthalene, fluorene, phenanthrene, fluorentene and benzofur. It is also preferable that the group is derived from any aromatic hydrocarbon selected from the group consisting of oranthene.
  • Ar 2 of the general formula (21) is a substituted or unsubstituted anthryl group.
  • Ar 2 of the general formula (21) is a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms.
  • Ar 2 of the general formula (21) is a substituted or unsubstituted group derived from the ring structure represented by the general formula (20).
  • Ar 2 of the general formula (21) is a group represented by the following general formula (23).
  • Each of X 21 to X 28 is a nitrogen atom, CR 21 , a group represented by the general formula (21), or a carbon atom bonded to L 22 or L 23, respectively.
  • L 21 is a linking group
  • L 21 as a linking group is a substituted or unsubstituted linear, branched or cyclic trivalent aliphatic hydrocarbon group having 1 to 50 carbon atoms, substituted or unsubstituted.
  • L 22 and L 23 are independently single-bonded or linking groups, and L 22 and L 23 as linking groups are independently substituted or unsubstituted linear and branched with 1 to 50 carbon atoms, respectively.
  • X 21 to X 28 of the general formula (23) are independent nitrogen atoms, CR 21 or carbon atoms bonded to L 22 or L 23 , respectively, and CR 21 or L 22 or L 23. It is more preferably a carbon atom bonded to.
  • the phenanthroline compound is also preferably a compound represented by the following general formula (24).
  • the plurality of R 21s are independently synonymous with R 21 in the general formula (20).
  • the plurality of R 22s are independently synonymous with R 21 in the general formula (20).
  • L 2 is synonymous with L 2 in the general formula (21).
  • p is 1, 2, 3, 4 or 5
  • the plurality of R 22 and L 2 are bonded to one of the carbon atoms at positions 1 to 10 of the anthracene ring.
  • the phenanthroline compound is also preferably a compound represented by the following general formula (24A).
  • the plurality of R 21s are independently synonymous with R 21 in the general formula (20).
  • the plurality of R 22s are independently synonymous with R 21 in the general formula (20).
  • L 2 is synonymous with L 2 in the general formula (21). )
  • the phenanthroline compound is also preferably a compound represented by the following general formula (24B).
  • the plurality of R 21s are independently synonymous with R 21 in the general formula (20).
  • the plurality of R 22s are independently synonymous with R 21 in the general formula (20).
  • L 2 is synonymous with L 2 in the general formula (21). )
  • the phenanthroline compound is also preferably a compound represented by the following general formula (25).
  • the plurality of R 21s are independently synonymous with R 21 in the general formula (20).
  • the plurality of R 22s are independently synonymous with R 21 in the general formula (20).
  • L 2 is synonymous with L 2 in the general formula (21).
  • p is 1, 2, 3, 4 or 5
  • the plurality of R 22 and L 2 are bonded to one of the carbon atoms at positions 2 to 9 of the phenanthroline ring.
  • the phenanthroline compound is also preferably a compound represented by the following general formula (25A).
  • the plurality of R 21s are independently synonymous with R 21 in the general formula (20).
  • the plurality of R 22s are independently synonymous with R 21 in the general formula (20).
  • L 2 is synonymous with L 2 in the general formula (21). )
  • L 2 of the general formulas (24), (24A), (24B), (25) and (25A) is a single bond, substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or substituted or absent. It is also preferable that the substituted ring-forming group is a divalent heterocyclic group having 5 to 50 atoms.
  • the phenanthroline compound is also preferably a compound represented by the following general formula (25B).
  • the plurality of R 21s are independently synonymous with R 21 in the general formula (20).
  • the plurality of R 22s are independently synonymous with R 21 in the general formula (20).
  • L 3 is a linking group, and L 3 as a linking group is Substituentally substituted or unsubstituted linear, branched or cyclic polyvalent aliphatic hydrocarbon groups having 1 to 50 carbon atoms, Substituted or unsubstituted polyvalent amino groups, Substituted or unsubstituted ring-forming polyvalent aromatic hydrocarbon ring groups having 6 to 50 carbon atoms, Substituent or unsubstituted ring forming A polyvalent heterocyclic group having 5 to 50 atoms, or two or three groups selected from the polyvalent aromatic hydrocarbon ring group and the polyvalent heterocyclic group are bonded.
  • the phenanthroline compound is also preferably a compound represented by the following general formula (25C).
  • R 21s are independently synonymous with R 21 in the general formula (20).
  • R 221 ⁇ R 230 1 single but a single bond to bond to L 3
  • R 221 ⁇ R 230 is not a single bond to bond to L 3 each independently and R 21 in the general formula (20)
  • Synonymous with L 3 is a linking group
  • L 3 as a linking group is synonymous with L 3 as a linking group in the general formula (25B).
  • p is 1, 2, 3, 4 or 5.
  • the phenanthroline compound is also preferably a compound represented by the following general formula (25D).
  • R 21s are independently synonymous with R 21 in the general formula (20).
  • R 221 ⁇ R 232 1 single but a single bond to bond to L 3
  • R 221 ⁇ R 232 is not a single bond to bond to L 3 each independently and R 21 in the general formula (20)
  • Synonymous with L 3 is a linking group
  • L 3 as a linking group is synonymous with L 3 as a linking group in the general formula (25B).
  • p is 1, 2, 3, 4 or 5.
  • the phenanthroline compound is also preferably a compound represented by the following general formula (25E).
  • R 21s are independently synonymous with R 21 in the general formula (20).
  • R 221 ⁇ R 230 1 single but a single bond to bond to L 3
  • R 221 ⁇ R 230 is not a single bond to bond to L 3 each independently and R 21 in the general formula (20)
  • Synonymous with L 3 is a linking group
  • L 3 as a linking group is synonymous with L 3 as a linking group in the general formula (25B).
  • p is 1, 2, 3, 4 or 5.
  • L 3 of the general formulas (25B), (25C), (25D) and (25E) is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or 5 substituted or unsubstituted ring-forming atoms. It is also preferable that it is a divalent heterocyclic group of about 50.
  • the phenanthroline compound can be produced by a known method.
  • the phenanthroline compound can also be produced by following a known method and using a known alternative reaction and raw material suitable for the desired product.
  • phenanthroline compound Specific examples include the following compounds. However, the present invention is not limited to specific examples of these phenanthroline compounds.
  • the first host material, the second host material, and the third host material are, for example, the following general formula (1), general formula (1X), general formula (12X), Examples thereof include the first compound represented by the general formula (13X), the general formula (14X), the general formula (15X) or the general formula (16X), and the second compound represented by the following general formula (2). Be done. Further, the first compound can also be used as the first host material and the second host material.
  • the first host material has a structure of the above condition (ii) in the molecule, that is, a linked structure containing a benzene ring and a naphthalene ring linked by a single bond.
  • the benzene ring and the naphthalene ring in the linked structure are independently further condensed or not fused with a monocyclic ring or a condensed ring, and the benzene ring and the naphthalene ring in the linked structure are the same. It is also preferable that at least one portion other than the single bond is further connected by cross-linking.
  • the first host material has a linking structure including such cross-linking, it can be expected that deterioration of the chromaticity of the organic EL element can be suppressed.
  • the first host material in this case has a linked structure (benzene-) in which a benzene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X1) or formula (X2), are contained in the molecule.
  • the first host material contains, in the molecule, a naphthalene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X3), formula (X4), or formula (X5).
  • one naphthalene ring contains a benzene ring, so that it contains a benzene-naphthalene linked structure.
  • the cross-linking contains a double bond. That is, it is also preferable that the benzene ring and the naphthalene ring have a structure in which the benzene ring and the naphthalene ring are further linked by a crosslinked structure containing a double bond in a portion other than the single bond.
  • the benzene ring and the naphthalene ring in the benzene-naphthalene linking structure are further linked by cross-linking at at least one portion other than the single bond, for example, in the case of the above formula (X1), the link represented by the following formula (X11). It becomes a structure (condensed ring), and in the case of the above formula (X3), it becomes a connected structure (condensed ring) represented by the following formula (X31).
  • the first host material has the structure of the above condition (i), that is, the first benzene ring and the second benzene ring are linked in a single bond in the molecule.
  • the biphenyl structure has a biphenyl structure, and the first benzene ring and the second benzene ring in the biphenyl structure are further linked by cross-linking at at least one portion other than the single bond.
  • the first host material has the structure of the condition (i) in the molecule, and the first benzene ring and the second benzene ring in the biphenyl structure are formed. It is also preferable that one portion other than the single bond is further connected by the cross-linking. Since the first host material has a biphenyl structure including such cross-linking, it can be expected to suppress deterioration of the chromaticity of the organic EL device.
  • the first host material has the structure of the condition (i) in the molecule, and the first benzene ring and the second benzene ring in the biphenyl structure are formed. It is also preferable that the two portions other than the single bond are further connected by the cross-linking.
  • the first host material has the structure of the condition (i) in the molecule and the crosslink contains a double bond. In the organic EL device according to the present embodiment, it is also preferable that the first host material has the structure of the condition (i) in the molecule and the crosslink does not contain a double bond.
  • the first host material has the structure of the condition (i) in the molecule, and the first benzene ring and the second benzene ring in the biphenyl structure are formed. It is also preferable that the two portions other than the single bond are further linked by the cross-linking, and the cross-linking does not contain a double bond. Since the first host material has a biphenyl structure including such cross-linking, it can be expected to suppress deterioration of the chromaticity of the organic EL device.
  • the biphenyl structure becomes It has a linked structure (condensed ring) such as the following formulas (BP11) to (BP15).
  • the formula (BP11) is a structure in which one portion other than the single bond is linked by a crosslink that does not contain a double bond.
  • the formula (BP12) is a structure in which one portion other than the single bond is linked by a crosslink including a double bond.
  • the formula (BP13) is a structure in which two portions other than the single bond are linked by a crosslink that does not contain a double bond.
  • the formula (BP14) has a structure in which one of the two portions other than the single bond is linked by a cross-link containing no double bond, and the other of the two portions other than the single bond is linked by a cross-link containing a double bond. Is.
  • the formula (BP15) is a structure in which two portions other than the single bond are linked by a crosslink including a double bond.
  • the first host material has at least one group represented by the following general formula (11), and the first compound represented by the following general formula (1). Is also preferable.
  • R 101 to R 110 is a group represented by the general formula (11).
  • the plurality of groups represented by the general formula (11) are the same or different from each other.
  • L 101 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • Ar 101 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • mx is 0, 1, 2, 3, 4 or 5 If L 101 is present 2 or more, 2 or more L 101 may be identical to each other or different, If Ar 101 is present 2 or more, two or more Ar 101 may be identical to each other or different, * In the general formula (11) indicates the bonding position with the pyrene ring in the general formula (1). )
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are independent of each other.
  • R 901 there are a plurality, a plurality of R 901 is the same or different from each other, If R 902 there are a plurality, a plurality of R 902 is the same or different from each other, If R 903 there are a plurality, a plurality of R 903 is the same or different from each other, If R 904 there are a plurality, a plurality of R 904 is the same or different from each other, If R 905 there are a plurality, a plurality of R 905 is the same or different from each other, If R 906 there are a plurality, a plurality of R 906 is the same or different from each other, If R 907 there are a plurality, a plurality of R 907 is the same or different from each other, If R 801 there are a plurality, a plurality of R 801 is the same or different from each other, If R 802 there are a plurality, a plurality of R 802 may or different are identical to one another. )
  • the group represented by the general formula (11) is preferably a group represented by the following general formula (111).
  • X 1 is CR 123 R 124 , oxygen atom, sulfur atom, or NR 125 .
  • L 111 and L 112 are independent of each other. Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • ma is 0, 1, 2, 3 or 4
  • mb is 0, 1, 2, 3 or 4 ma + mb is 0, 1, 2, 3 or 4
  • Ar 101 is synonymous with Ar 101 in the general formula (11).
  • R 121 , R 122 , R 123 , R 124 and R 125 are independent of each other.
  • L 111 is bonded to either position * 2 carbon atoms in the ring structure represented by the general formula (111a), L 112 is the general formula ( When bonded to the position of the carbon atom of * 7 in the ring structure represented by 111a), the group represented by the general formula (111) is represented by the following general formula (111b).
  • X 1 , L 111 , L 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124 and R 125 are independently X 1 , L 111 , L in the general formula (111). Synonymous with 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124 and R 125.
  • a plurality of R 121s are the same as or different from each other.
  • a plurality of R 122s are the same as or different from each other.
  • the group represented by the general formula (111) is preferably the group represented by the general formula (111b).
  • the organic EL element according to this embodiment ma is 0, 1 or 2
  • the mb is preferably 0, 1 or 2.
  • the organic EL element according to this embodiment is 0 or 1 and The mb is preferably 0 or 1.
  • Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • Ar 101 is Substituted or unsubstituted phenyl group, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl group, Substituted or unsubstituted pyrenyl groups, It is preferably a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted fluorenyl group.
  • Ar 101 is a group represented by the following general formula (12), general formula (13) or general formula (14).
  • R 111 to R 120 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Substituent or unsubstituted
  • the first compound is preferably represented by the following general formula (101).
  • R 101 to R 110 indicates the connection position with L 101
  • one of R 111 to R 120 indicates the connection position with L 101.
  • L 101 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • mx is 0, 1, 2, 3, 4 or 5 When two or more L 101s are present, the two or more L 101s are the same as or different from each other. )
  • R 101 to R 110 and R 111 to R 120 are independent of each other.
  • Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), Substituent or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -C (
  • R 101 to R 110 indicates the connection position with L 101
  • one of R 111 to R 120 indicates the connection position with L 101.
  • L 101 is Single bond, It is an arylene group having 6 to 24 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 24 substituted or unsubstituted ring-forming atoms.
  • mx is 1, 2, 3, 4 or 5
  • the two or more L 101s are the same as or different from each other.
  • the first compound is the following general formula (1010), general formula (1011), general formula (1012), general formula (1013), general formula (1014) or general formula (1014). It is preferably represented by (1015).
  • L 101 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • mx is 0, 1, 2, 3, 4 or 5 When two or more L 101s are present, the two or more L 101s are the same as or different from each other. )
  • the compound represented by the general formula (1010), R 103 represents a bonding position to L 101, R 120 corresponds to a compound in the case shown a binding position with the L 101.
  • the compound represented by the general formula (1011) is, R 103 represents a bonding position to L 101, R 111 corresponds to a compound in the case shown a binding position with the L 101.
  • the compound represented by the general formula (1012) is, R 103 represents a bonding position to L 101, R 118 corresponds to a compound in the case shown a binding position with the L 101.
  • the compound represented by the general formula (1013) is, R 102 represents a bonding position to L 101, R 111 corresponds to a compound in the case shown a binding position with the L 101.
  • the compound represented by the general formula (1014) is, R 102 represents a bonding position to L 101, R 118 corresponds to a compound in the case shown a binding position with the L 101.
  • the compound represented by the general formula (1015) is, R 105 represents a bonding position to L 101, R 118 corresponds to a compound in the case shown a binding position with the L 101.
  • the first compound is preferably represented by the general formula (1010).
  • R 101 to R 110 which are not the coupling positions with L 101 , are independently of each other.
  • R 101 to R 110 which are not the coupling positions with L 101 , are independently of each other.
  • Hydrogen atom Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms are preferable.
  • R 101 to R 110 which are not the bonding positions with L 101 , are preferably hydrogen atoms.
  • R 111 to R 120 which are not the coupling positions with L 101 , are independent of each other.
  • R 111 to R 120 which are not the coupling positions with L 101 , are independent of each other.
  • Hydrogen atom Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms are preferable.
  • R 111 to R 120 which are not the bonding positions with L 101 , are preferably hydrogen atoms.
  • L 101 is It is preferably a single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms.
  • L 101 is Single bond, It is also preferable that it is an arylene group having 6 to 18 substituted or unsubstituted ring-forming carbon atoms or a divalent heterocyclic group having 5 to 18 substituted or unsubstituted ring-forming atoms.
  • L 101 is It is also preferable that it is a single bond or a substituted or unsubstituted ring-forming arylene group having 6 to 18 carbon atoms.
  • L 101 is It is also preferable that it is a substituted or unsubstituted ring-forming arylene group having 6 to 18 carbon atoms.
  • L 101 is Single bond, It is also preferable that it is an arylene group having 6 to 13 substituted or unsubstituted ring-forming carbon atoms or a divalent heterocyclic group having 5 to 13 substituted or unsubstituted ring-forming atoms.
  • L 101 is It is also preferable that it is a single bond or a substituted or unsubstituted ring-forming arylene group having 6 to 13 carbon atoms.
  • L 101 is It is also preferable that it is a substituted or unsubstituted ring-forming arylene group having 6 to 13 carbon atoms.
  • the mx is preferably 1, 2, or 3.
  • the mx is preferably 1 or 2.
  • mx is 1, 2 or 3
  • L 101 is It is also preferable that it is an arylene group having 6 to 18 substituted or unsubstituted ring-forming carbon atoms or a divalent heterocyclic group having 5 to 18 substituted or unsubstituted ring-forming atoms.
  • mx is 1 or 2.
  • L 101 is It is also preferable that it is an arylene group having 6 to 18 substituted or unsubstituted ring-forming carbon atoms or a divalent heterocyclic group having 5 to 18 substituted or unsubstituted ring-forming atoms.
  • mx is 1 or 2. It is also preferable that L 101 is a substituted or unsubstituted ring-forming arylene group having 6 to 18 carbon atoms.
  • the first compound is preferably represented by the following general formula (102).
  • R 101 to R 120 are independently synonymous with R 101 to R 120 in the general formula (101). However, one of R 101 to R 110 indicates the connection position with L 111, and one of R 111 to R 120 indicates the connection position with L 112.
  • X 1 is CR 123 R 124 , oxygen atom, sulfur atom, or NR 125 .
  • L 111 and L 112 are independent of each other. Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • R 121 , R 122 , R 123 , R 124 and R 125 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsub
  • ma is 0, 1 or 2
  • mb is preferably 0, 1 or 2.
  • ma is 0 or 1 and The mb is preferably 0 or 1.
  • L 111 and L 112 are independently, respectively. Single bond, It is preferably an arylene group having 6 to 24 substituted or unsubstituted ring-forming carbon atoms or a divalent heterocyclic group having 5 to 24 substituted or unsubstituted ring-forming atoms.
  • ma is 1, 2, or 3 mb is 1, 2, or 3 ma + mb is 2, 3 or 4,
  • ma is 1 or 2
  • mb is preferably 1 or 2.
  • ma is 1,
  • mb is preferably 1.
  • R 101 to R 110 which are not the coupling positions with L 111 , are independently of each other.
  • R 101 to R 110 which are not the coupling positions with L 111 , are independently of each other.
  • Hydrogen atom Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms are preferable.
  • R 101 to R 110 which are not the bonding positions with L 111 , are preferably hydrogen atoms.
  • R 111 to R 120 which are not the coupling positions with L 112 , are independent of each other.
  • R 111 to R 120 which are not the coupling positions with L 112 , are independent of each other.
  • Hydrogen atom Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms are preferable.
  • R 111 to R 120 which are not the bonding positions with L 112 , are preferably hydrogen atoms.
  • R 101 to R 110 are groups represented by the general formula (11).
  • R 101 to R 110 are groups represented by the general formula (11), and Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. Is preferable.
  • Ar 101 is not a substituted or unsubstituted pyrenyl group
  • L 101 is not a substituted or unsubstituted pyrenylene group
  • the substituted or unsubstituted aryl group having 6 to 50 carbon atoms as R 101 to R 110 which is not the group represented by the general formula (11), is preferably not a substituted or unsubstituted pyrenyl group.
  • R 101 to R 110 which are not groups represented by the general formula (11), are independent of each other.
  • R 101 to R 110 which are not groups represented by the general formula (11), are independent of each other.
  • Hydrogen atom Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms are preferable.
  • R 101 to R 110 which are not groups represented by the general formula (11), are preferably hydrogen atoms.
  • the groups described as "substituted or unsubstituted” are preferably "unsubstituted” groups.
  • one of R 101 to R 110 in the first compound represented by the general formula (1) is a group represented by the general formula (11), and mx is 1 or more.
  • one of R 101 to R 110 in the first compound represented by the general formula (1) is a group represented by the general formula (11), mx is 0, and Ar 101 is substituted. Alternatively, it is an unsubstituted aryl group.
  • one of R 101 to R 110 in the first compound represented by the general formula (1) is a group represented by the general formula (11), mx is 0, and Ar 101 is substituted. Alternatively, it is a heterocyclic group containing an unsubstituted nitrogen atom.
  • one of R 101 to R 110 in the first compound represented by the general formula (1) is a group represented by the general formula (11), mx is 0, and Ar 101 is substituted. Alternatively, it is a heterocyclic group containing an unsubstituted sulfur atom.
  • one of R 101 to R 110 in the first compound represented by the general formula (1) is a group represented by the general formula (11), mx is 0, and Ar 101 is substituted.
  • an unsubstituted frill group Oxazolyl group, Isooxazolyl group, Oxaziazolyl group, Xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholine group, Ginaftfuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftbenzofuranyl group and diazanaphthobenzofuranyl group.
  • one of R 101 to R 110 in the first compound represented by the general formula (1) is a group represented by the general formula (11), mx is 0, and Ar 101 is absent.
  • one of R 101 to R 110 in the first compound represented by the general formula (1) is a group represented by the general formula (11).
  • mx is 0 and Ar 101 is a substituted or unsubstituted dibenzofuranyl group.
  • one of R 101 to R 110 in the first compound represented by the general formula (1) is a group represented by the general formula (11).
  • mx is 0 and Ar 101 is an unsubstituted dibenzofuranyl group.
  • mx in the first compound represented by the general formula (101) is 2 or more.
  • mx in the first compound represented by the general formula (101) is 1 or more
  • L 101 is an arylene group having 6 to 24 ring-forming carbon atoms, or It is a divalent heterocyclic group having 5 to 24 ring-forming atoms.
  • mx in the first compound represented by the general formula (101) is 1 or more
  • L 101 is an arylene group having 6 to 18 ring-forming carbon atoms, or It is a divalent heterocyclic group having 5 to 18 ring-forming atoms.
  • the first compound is preferably a compound represented by the following general formula (1X).
  • R 101 to R 112 is a group represented by the general formula (11X).
  • the plurality of groups represented by the general formula (11X) are the same or different from each other.
  • L 101 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • Ar 101 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • mx is 1, 2, 3, 4 or 5 If L 101 is present 2 or more, 2 or more L 101 may be identical to each other or different, If Ar 101 is present 2 or more, two or more Ar 101 may be identical to each other or different, * In the general formula (11X) indicates a bonding position with the benz [a] anthracene ring in the general formula (1X). )
  • the group represented by the general formula (11X) is preferably a group represented by the following general formula (111X).
  • X 1 is CR 143 R 144 , oxygen atom, sulfur atom, or NR 145 .
  • L 111 and L 112 are independent of each other. Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • ma is 1, 2, 3 or 4 mb is 1, 2, 3 or 4 ma + mb is 2, 3 or 4,
  • Ar 101 is synonymous with Ar 101 in the general formula (11).
  • R 141 , R 142 , R 143 , R 144 and R 145 are independent of each other.
  • L 111 is bonded to either position * 2 carbon atoms in the ring structure represented by the general formula (111aX)
  • L 112 is the general formula (
  • the group represented by the general formula (111X) is represented by the following general formula (111bX).
  • X 1 , L 111 , L 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145 are independently X 1 , L 111 , L in the general formula (111X). Synonymous with 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145. Multiple R 141s are the same as or different from each other, A plurality of R 142s are the same as or different from each other. )
  • the group represented by the general formula (111X) is preferably the group represented by the general formula (111bX).
  • ma is preferably 1 or 2
  • mb is preferably 1 or 2.
  • ma is preferably 1 and mb is preferably 1.
  • Ar 101 is preferably an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms.
  • Ar 101 is Substituted or unsubstituted phenyl group, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl group, Substituted or unsubstituted benz [a] anthryl group, Substituted or unsubstituted pyrenyl groups, It is preferably a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted fluorenyl group.
  • the compound represented by the general formula (1X) is preferably represented by the following general formula (101X).
  • R 111 and R 112 indicates the connection position with L 101
  • one of R 133 and R 134 indicates the connection position with L 101
  • R 101 ⁇ R 110, R 121 ⁇ R 130, L 101 is not a point of attachment and R 111 or R 112
  • R 133, or R 134 is not a point of attachment and L 101 are independently Hydrogen atom
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms
  • Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R
  • L 101 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • mx is 1, 2, 3, 4 or 5 When two or more L 101s are present, the two or more L 101s are the same as or different from each other. )
  • L 101 is preferably a single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms.
  • the compound represented by the general formula (1X) is preferably represented by the following general formula (102X).
  • R 111 and R 112 indicates the connection position with L 111
  • one of R 133 and R 134 indicates the connection position with L 112.
  • R 101 to R 110 , R 121 to R 130 , R 111 or R 112 not connected to L 111, and R 133 or R 134 not connected to L 112 are independent of each other.
  • X 1 is CR 143 R 144 , oxygen atom, sulfur atom, or NR 145 .
  • L 111 and L 112 are independent of each other. Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • ma is 1, 2, 3 or 4 mb is 1, 2, 3 or 4 ma + mb is 2, 3, 4 or 5
  • R 141 , R 142 , R 143 , R 144 and R 145 are independent of each other.
  • ma in the general formula (102X) is preferably 1 or 2
  • mb is preferably 1 or 2.
  • ma in the general formula (102X) is preferably 1, and mb is preferably 1.
  • the group represented by the general formula (11X) is a group represented by the following general formula (11AX) or a group represented by the following general formula (11BX). Is also preferable.
  • R 121 to R 131 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), Substituent or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -C
  • the plurality of groups represented by the general formula (11AX) are the same or different from each other.
  • the plurality of groups represented by the general formula (11BX) are the same or different from each other.
  • L 131 and L 132 are independent of each other, Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • the * in the general formula (11AX) and the general formula (11BX) indicates the bonding position with the benz [a] anthracene ring in the general formula (1X), respectively.
  • the compound represented by the general formula (1X) is preferably represented by the following general formula (103X).
  • R 101 to R 110 and R 112 are synonymous with R 101 to R 110 and R 112 in the general formula (1X), respectively.
  • R 121 to R 131 , L 131 and L 132 are synonymous with R 121 to R 131 , L 131 and L 132 in the general formula (11BX), respectively.
  • L 131 is a substituted or unsubstituted arylene group having 6 to 50 carbon atoms.
  • L 132 is preferably an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms.
  • R 101 to R 112 are groups represented by the general formula (11).
  • R 101 to R 112 are groups represented by the general formula (11X), and Ar 101 in the general formula (11X) is ,
  • Substituent or unsubstituted, ring-forming is preferably an aryl group having 6 to 50 carbon atoms.
  • Ar 101 is not a substituted or unsubstituted benz [a] anthryl group
  • L 101 is not a substituted or unsubstituted benz [a] anthrylene group
  • the substituted or unsubstituted aryl group having 6 to 50 carbon atoms as R 101 to R 110 which is not the group represented by the general formula (11X), is not a substituted or unsubstituted benz [a] anthryl group. It is also preferable.
  • R 101 to R 112 which are not groups represented by the general formula (11X), are independently.
  • R 101 to R 112 which are not groups represented by the general formula (11X) are Hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms are preferable.
  • R 101 to R 112 which are not groups represented by the general formula (11X), are preferably hydrogen atoms.
  • the first compound is preferably a compound represented by the following general formula (12X).
  • R 1201 to R 1210 Combine with each other to form a substituted or unsubstituted monocycle, or combine with each other to form a substituted or unsubstituted fused ring.
  • R 1201 to R 1210 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, are independent of each other.
  • the plurality of groups represented by the general formula (121) are the same or different from each other.
  • L 1201 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • Ar 1201 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • mx2 is 0, 1, 2, 3, 4 or 5 If L 1201 is present 2 or more, 2 or more L 1201 may be identical to each other or different, If Ar 1201 there are two or more, two or more Ar 1201 may be identical to each other or different, * In the general formula (121) indicates the bonding position with the ring represented by the general formula (12X). )
  • the pair consisting of two adjacent R 1201 to R 1210 is a pair of R 1201 and R 1202 , a pair of R 1202 and R 1203, and R 1203 and R 1204 .
  • the first compound is preferably a compound represented by the following general formula (13X).
  • R 1301 to R 1310 is a group represented by the general formula (131).
  • the plurality of groups represented by the general formula (131) are the same or different from each other.
  • L 1301 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • Ar 1301 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • L 1301 is present 2 or more, 2 or more L 1301 may be identical to each other or different, If Ar 1301 there are two or more, two or more Ar 1301 may be identical to each other or different, * In the general formula (131) indicates the bonding position with the fluoranthene ring in the general formula (13X). )
  • none of the adjacent pairs of R 1301 to R 1310 which are not groups represented by the general formula (131), are bonded to each other.
  • the two adjacent sets are the set of R 1301 and R 1302 , the set of R 1302 and R 1303 , the set of R 1303 and R 1304, and the set of R 1304 and R 1305 . , R 1305 and R 1306 , R 1307 and R 1308 , R 1308 and R 1309, and R 1309 and R 1310 .
  • the first compound is preferably a compound represented by the following general formula (14X).
  • R 1401 to R 1410 is a group represented by the general formula (141).
  • the plurality of groups represented by the general formula (141) are the same or different from each other.
  • L 1401 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • Ar 1401 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • L 1401 is present 2 or more, 2 or more L 1401 may be identical to each other or different, If Ar 1401 there are two or more, two or more Ar 1401 may be identical to each other or different, * In the general formula (141) indicates the bonding position with the ring represented by the general formula (14X). )
  • the first compound is preferably a compound represented by the following general formula (15X).
  • R 1501 to R 1514 is a group represented by the general formula (151).
  • the plurality of groups represented by the general formula (151) are the same or different from each other.
  • L 1501 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • Ar 1501 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • mx5 is 0, 1, 2, 3, 4 or 5 If L 1501 is present 2 or more, 2 or more L 1501 may be identical to each other or different, If Ar 1501 there are two or more, two or more Ar 1501 may be identical to each other or different, * In the general formula (151) indicates the bonding position with the ring represented by the general formula (15X). )
  • the first compound is preferably a compound represented by the following general formula (16X).
  • R 1601 to R 1614 is a group represented by the general formula (161).
  • the plurality of groups represented by the general formula (161) are the same or different from each other.
  • L 1601 is Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • Ar 1601 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • mx6 is 0, 1, 2, 3, 4 or 5 If L 1601 is present 2 or more, 2 or more L 1601 may be identical to each other or different, If Ar 1601 there are two or more, two or more Ar 1601 may be identical to each other or different, * In the general formula (161) indicates the bonding position with the ring represented by the general formula (16X). )
  • the groups described as "substituted or unsubstituted” are preferably "unsubstituted” groups.
  • the first compound can be produced by a known method.
  • the first compound can also be produced by following a known method and using known alternative reactions and raw materials suitable for the desired product.
  • Specific examples of the first compound include the following compounds. However, the present invention is not limited to specific examples of these first compounds.
  • D represents a deuterium atom
  • Me represents a methyl group
  • tBu represents a tert-butyl group.
  • the second host material is preferably an anthracene derivative.
  • the second host material is the second compound represented by the following general formula (2).
  • R 201 to R 208 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Substituent or unsubstituted aralkyl groups having 7 to 50 carbon atoms,
  • L 201 and L 202 are independent of each other. Single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming ring-forming divalent heterocyclic group having 5 to 50 atoms.
  • Ar 201 and Ar 202 are independent of each other. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms. )
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are independent of each other.
  • R 901 there are a plurality, a plurality of R 901 is the same or different from each other, If R 902 there are a plurality, a plurality of R 902 is the same or different from each other, If R 903 there are a plurality, a plurality of R 903 is the same or different from each other, If R 904 there are a plurality, a plurality of R 904 is the same or different from each other, If R 905 there are a plurality, a plurality of R 905 is the same or different from each other, If R 906 there are a plurality, a plurality of R 906 is the same or different from each other, If R 907 there are a plurality, a plurality of R 907 is the same or different from each other, If R 801 there are a plurality, a plurality of R 801 is the same or different from each other, If R 802 there are a plurality, a plurality of R 802 may or different are identical to one another. )
  • R 201 to R 208 are independent of each other.
  • Ar 201 and Ar 202 are independent of each other. It is preferably an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
  • L 201 and L 202 are independent of each other.
  • Ar 201 and Ar 202 are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
  • Ar 201 and Ar 202 are independent of each other.
  • the second compound represented by the general formula (2) is the following general formula (201), general formula (202), general formula (203), general formula (204).
  • the compound represented by the general formula (205), the general formula (206), the general formula (207), the general formula (208) or the general formula (209) is preferable.
  • L 201 and Ar 201 are synonymous with L 201 and Ar 201 in the general formula (2).
  • R 201 to R 208 are independently synonymous with R 201 to R 208 in the general formula (2).
  • the second compound represented by the general formula (2) includes the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), and general formula (22). It is also preferable that the compound is represented by the general formula (227), the general formula (228) or the general formula (229).
  • R 201 and R 203 to R 208 are independently synonymous with R 201 and R 203 to R 208 in the general formula (2).
  • L 201 and Ar 201 are synonymous with L 201 and Ar 201 in the general formula (2), respectively.
  • L 203 is synonymous with L 201 in the general formula (2).
  • L 203 and L 201 are the same as or different from each other,
  • Ar 203 is synonymous with Ar 201 in the general formula (2).
  • Ar 203 and Ar 201 are the same as or different from each other.
  • the second compound represented by the general formula (2) is the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (24). 246), it is also preferable that it is a compound represented by the general formula (247), the general formula (248) or the general formula (249).
  • R 201 , R 202 and R 204 to R 208 are independently synonymous with R 201 , R 202 and R 204 to R 208 in the general formula (2).
  • L 201 and Ar 201 are synonymous with L 201 and Ar 201 in the general formula (2), respectively.
  • L 203 is synonymous with L 201 in the general formula (2).
  • L 203 and L 201 are the same as or different from each other,
  • Ar 203 is synonymous with Ar 201 in the general formula (2).
  • Ar 203 and Ar 201 are the same as or different from each other.
  • R 201 to R 208 which are not groups represented by the general formula (21), are independently.
  • L 101 is A single-bonded or unsubstituted ring-forming arylene group having 6 to 22 carbon atoms.
  • Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 22 carbon atoms.
  • R 201 to R 208 which are substituents of the anthracene skeleton, suppress the interaction between molecules.
  • a hydrogen atom is preferable from the viewpoint of preventing a decrease in electron mobility and suppressing a decrease in electron mobility.
  • R 201 to R 208 are substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms, or substituted or absent. It may be a heterocyclic group having 5 to 50 atoms forming a ring of substitution.
  • R 201 to R 208 become bulky substituents such as an alkyl group and a cycloalkyl group, the interaction between molecules is suppressed, the electron mobility with respect to the first host material decreases, and the above formula (number). There is a possibility that the relationship of ⁇ e (H1) ⁇ e (H2) described in 33) will not be satisfied.
  • the second compound is used in the second light emitting layer, the recombination ability between holes and electrons in the first light emitting layer is reduced by satisfying the relationship of ⁇ e (H1) ⁇ e (H2). And it can be expected to suppress the decrease in luminous efficiency.
  • the substituents include a haloalkyl group, an alkenyl group, an alkynyl group, a group represented by -Si (R 901 ) (R 902 ) (R 903 ), a group represented by -O- (R 904 ), and-.
  • the group represented by S- (R 905 ), the group represented by -N (R 906 ) (R 907 ), the aralkyl group, the group represented by -C ( O) R 801 and the group represented by -COOR 802 .
  • the groups to be treated, halogen atoms, cyano groups, and nitro groups may be bulky, and the alkyl groups and cycloalkyl groups may be further bulky.
  • R 201 to R 208 which are substituents of the anthracene skeleton, are preferably not bulky substituents and are not alkyl groups or cycloalkyl groups.
  • R 801 group More preferably, it is not a group represented by, a halogen atom, a cyano group, and a nitro group.
  • R 201 to R 208 are independent of each other.
  • R 201 to R 208 are preferably hydrogen atoms.
  • the substituents in the case of "substituted or unsubstituted" in R 201 to R 208 are the above-mentioned potentially bulky substituents, particularly substituted or unsubstituted alkyl groups, and substituted or unsubstituted. It is also preferable that it does not contain a substituted cycloalkyl group.
  • the substituent in the case of "substituted or unsubstituted" in R 201 to R 208 does not contain a substituted or unsubstituted alkyl group and a substituted or unsubstituted cycloalkyl group, whereby an alkyl group, a cycloalkyl group, etc.
  • R 201 to R 208 which are substituents of the anthracene skeleton, are not bulky substituents, and R 201 to R 208 , which are substituents, are unsubstituted. Further, when R 201 to R 208 which are substituents of the anthracene skeleton are not bulky substituents and the substituents are bonded to R 201 to R 208 which are not bulky substituents, the substituents are also bulky.
  • the groups described as "substituted or unsubstituted” are preferably "unsubstituted” groups.
  • Ar 201 in the second compound represented by the general formula (2) is a substituted or unsubstituted dibenzofuranyl group.
  • Ar 201 in the second compound represented by the general formula (2) is an unsubstituted dibenzofuranyl group.
  • the second compound represented by the general formula (2) has at least one hydrogen, and at least one of the hydrogens is deuterium.
  • L 201 in the second compound represented by the general formula (2) is TEMP-63 to TEMP-68.
  • Ar 201 in the second compound represented by the general formula (2) is a substituted or unsubstituted anthryl group.
  • Ar 201 in the second compound represented by the general formula (2) is a substituted or unsubstituted fluorenyl group.
  • Ar 201 in the second compound represented by the general formula (2) is a substituted or unsubstituted xanthenyl group.
  • Ar 201 in the second compound represented by the general formula (2) is a benzoxanthenyl group.
  • the second compound can be produced by a known method.
  • the second compound can also be produced by following a known method and using a known alternative reaction and raw material suitable for the desired product.
  • Specific examples of the second compound include the following compounds. However, the present invention is not limited to specific examples of these second compounds.
  • examples of the first luminescent compound, the second luminescent compound, and the third luminescent compound include the following third compound, the following fourth compound, and the like. Be done.
  • the third compound and the fourth compound are independently represented by the following general formula (3), the following general formula (4), and the following general formula (5).
  • the compound represented by the following general formula (6), the compound represented by the following general formula (7), the compound represented by the following general formula (8), the compound represented by the following general formula (9), and It is one or more compounds selected from the group consisting of the compounds represented by the following general formula (10).
  • R 301 to R 310 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other
  • At least one of R 301 to R 310 is a monovalent group represented by the following general formula (31).
  • R 301 to R 310 which do not form the monocyclic ring, do not form the condensed ring, and are not monovalent groups represented by the following general formula (31), are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms. )
  • Ar 301 and Ar 302 are independent of each other.
  • L 301 to L 303 are independent of each other, Single bond, It is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms. * Indicates the bond position in the pyrene ring in the general formula (3).
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 are independent of each other.
  • R 901 there are a plurality, a plurality of R 901 is the same or different from each other
  • R 902 there are a plurality a plurality of R 902 is the same or different from each other
  • R 903 there are a plurality, a plurality of R 903 is the same or different from each other
  • R 904 there are a plurality, a plurality of R 904 is the same or different from each other
  • R 906 there are a plurality, a plurality of R 906 is the same or different from each other
  • R 907 there are a plurality a plurality of R 907 may or different are identical to one another.
  • R 301 to R 310 are groups represented by the general formula (31).
  • the compound represented by the general formula (3) is a compound represented by the following general formula (33).
  • R 311 to R 318 are independently synonymous with R 301 to R 310 in the general formula (3), which are not monovalent groups represented by the general formula (31).
  • L 311 to L 316 are independent of each other. Single bond, It is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms.
  • Ar 312 , Ar 313 , Ar 315 and Ar 316 are independent of each other.
  • L 301 is preferably a single bond
  • L 302 and L 303 are preferably a single bond.
  • the compound represented by the general formula (3) is represented by the following general formula (34) or general formula (35).
  • R 311 to R 318 are independently synonymous with R 301 to R 310 in the general formula (3), which are not monovalent groups represented by the general formula (31).
  • L 312 , L 313 , L 315 and L 316 are independently synonymous with L 312 , L 313 , L 315 and L 316 in the general formula (33).
  • Ar 312 , Ar 313 , Ar 315 and Ar 316 are independently synonymous with Ar 312 , Ar 313 , Ar 315 and Ar 316 in the general formula (33), respectively.
  • R 311 to R 318 are independently synonymous with R 301 to R 310 in the general formula (3), which are not monovalent groups represented by the general formula (31).
  • Ar 312 , Ar 313 , Ar 315 and Ar 316 are independently synonymous with Ar 312 , Ar 313 , Ar 315 and Ar 316 in the general formula (33), respectively.
  • At least one of Ar 301 and Ar 302 is a group represented by the following general formula (36).
  • at least one of Ar 312 and Ar 313 is a group represented by the following general formula (36).
  • at least one of Ar 315 and Ar 316 is a group represented by the following general formula (36).
  • X 3 represents an oxygen atom or a sulfur atom
  • R 321 to R 327 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 321 to R 327 , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms. * Indicates
  • X 3 is preferably an oxygen atom.
  • At least one of R 321 to R 327 Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, It is preferably an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
  • Ar 301 is a group represented by the general formula (36) and Ar 302 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • Ar 312 is a group represented by the general formula (36)
  • Ar 313 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. It is preferable to have.
  • Ar 315 is a group represented by the general formula (36)
  • Ar 316 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. It is preferable to have.
  • the compound represented by the general formula (3) is represented by the following general formula (37).
  • R 311 to R 318 are independently synonymous with R 301 to R 310 in the general formula (3), which are not monovalent groups represented by the general formula (31).
  • One or more of the two or more adjacent pairs of R 321 to R 327 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other
  • One or more of the two or more adjacent pairs of R 341 to R 347 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 321 to R 327 and R 341 to R 347 , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • R 331 to R 335 and R 351 to R 355 are independent of each other.
  • Z is independently a CRa or nitrogen atom
  • the A1 ring and the A2 ring are independent of each other.
  • one or more pairs of two or more adjacent Ras among the plurality of Ras may be present.
  • Bond to each other to form substituted or unsubstituted fused rings, or not to each other n21 and n22 are 0, 1, 2, 3 or 4, respectively.
  • Rbs When there are a plurality of Rbs, one or more of a pair consisting of two or more adjacent Rbs among the plurality of Rbs Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other
  • Rc one or more of a pair consisting of two or more adjacent Rc among the plurality of Rc Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other Ra, Rb, and Rc, which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms. )
  • the "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group”.
  • the "aromatic hydrocarbon ring" of the A1 ring and the A2 ring contains two carbon atoms on the condensed bicyclic structure at the center of the general formula (4) as ring-forming atoms.
  • Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms” include a compound in which a hydrogen atom is introduced into the "aryl group” described in the specific example group G1.
  • the "heterocycle" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group”.
  • the "heterocycle” of the A1 ring and the A2 ring contains two carbon atoms on the condensed bicyclic structure at the center of the general formula (4) as ring-forming atoms.
  • Specific examples of the "heterocyclic ring having 5 to 50 substituted or unsubstituted ring-forming atoms” include a compound in which a hydrogen atom is introduced into the "heterocyclic group" described in the specific example group G2.
  • Rb is bonded to either a carbon atom forming an aromatic hydrocarbon ring as an A1 ring or an atom forming a heterocycle as an A1 ring.
  • Rc is bonded to either a carbon atom forming an aromatic hydrocarbon ring as an A2 ring or an atom forming a heterocycle as an A2 ring.
  • Ra is preferably a group represented by the following general formula (4a), and at least two are more preferably a group represented by the following general formula (4a). ..
  • L 401 is Single bond, It is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms.
  • Ar 401 is Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 50 atoms or a group represented by the following general formula (4b).
  • L 402 and L 403 are independent of each other. Single bond, It is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms.
  • the set consisting of Ar 402 and Ar 403 is Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other Ar 402 and Ar 403 , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • the compound represented by the general formula (4) is represented by the following general formula (42).
  • R 401 to R 411 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 401 to R 411 , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms. )
  • R 401 to R 411 at least one is preferably a group represented by the general formula (4a), and more preferably at least two groups are represented by the general formula (4a). It is preferable that R 404 and R 411 are groups represented by the general formula (4a).
  • the compound represented by the general formula (4) is a compound in which a structure represented by the following general formula (4-1) or general formula (4-2) is bound to the A1 ring. Further, in one embodiment, the compound represented by the general formula (42) is represented by the following general formula (4-1) or general formula (4-2) on the ring to which R 404 to R 407 are bonded. It is a compound with a combined structure.
  • the two *'s are independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring as the A1 ring of the general formula (4) or the ring-forming atom of the heterocycle. Or combine with any of R 404 to R 407 of the general formula (42). Whether the three * of the general formula (4-2) are independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring as the A1 ring of the general formula (4) or the ring-forming atom of the heterocycle. , Or in combination with any of R 404 to R 407 of the general formula (42).
  • R 421 to R 427 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other
  • One or more of two or more adjacent pairs of R 431 to R 438 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 421 to R 427 and R 431 to R 438 , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms. )
  • the compound represented by the general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4) or general formula (41-5). ..
  • R 421 to R 427 are independently synonymous with R 421 to R 427 in the general formula (4-1).
  • R 440 to R 448 are independently synonymous with R 401 to R 411 in the general formula (42). )
  • the substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms as the A1 ring of the general formula (41-5) is It is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring.
  • the substituted or unsubstituted heterocycle having 5 to 50 atoms forming the ring as the A1 ring of the general formula (41-5) is a heterocycle.
  • the compound represented by the general formula (4) or the general formula (42) is selected from the group consisting of compounds represented by the following general formulas (461) to (467). ..
  • R 421 to R 427 are independently synonymous with R 421 to R 427 in the general formula (4-1).
  • R 431 to R 438 are independently synonymous with R 431 to R 438 in the general formula (4-2).
  • R 440 to R 448 and R 451 to R 454 are independently synonymous with R 401 to R 411 in the general formula (42).
  • X 4 is an oxygen atom, NR 801 or C (R 802 ) (R 803 ).
  • R801 , R802 and R803 are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
  • R 801 there are a plurality a plurality of R 801 is the same or different from each other, If R 802 there are a plurality, a plurality of R 802 is the same or different from each other, If R 803 there are a plurality, a plurality of R 803 may or different are identical to one another. )
  • one or more sets of two or more adjacent pairs of R 401 to R 411 are bonded to each other to be substituted or unsubstituted.
  • a single ring is formed or bonded to each other to form a substituted or unsubstituted fused ring, and the embodiment will be described in detail as a compound represented by the general formula (45) below.
  • R 461 to R 471 Two or more rings formed by R 461 to R 471 are the same as or different from each other.
  • R 461 to R 471 which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • R n and R n + 1 (n represents an integer selected from 461, 462, 464 to 466, and 468 to 470) are combined with each other, and R n and R n + 1 are combined 2 Together with the two ring-forming carbon atoms, a substituted or unsubstituted monocycle or a substituted or unsubstituted fused ring is formed.
  • the ring is preferably composed of atoms selected from the group consisting of carbon atoms, oxygen atoms, sulfur atoms and nitrogen atoms, and the number of atoms in the ring is preferably 3 to 7, more preferably 5 or It is 6.
  • the number of the ring structures in the compound represented by the general formula (45) is, for example, 2, 3, or 4.
  • the two or more ring structures may be present on the same benzene ring on the matrix of the general formula (45), or may be present on different benzene rings.
  • one ring structure may be present for each of the three benzene rings of the general formula (45).
  • Examples of the ring structure in the compound represented by the general formula (45) include structures represented by the following general formulas (451) to (460).
  • R n and R n + 1 Represents the two ring-forming carbon atoms to which The ring-forming carbon atoms to which R n is bonded are * 1 and * 2, * 3 and * 4, * 5 and * 6, * 7 and * 8, * 9 and * 10, * 11 and * 12, and * 13 and * 14, respectively, R n and R n + 1, respectively.
  • Represents the two ring-forming carbon atoms to which The ring-forming carbon atoms to which R n is bonded are * 1 and * 2, * 3 and * 4, * 5 and * 6, * 7 and * 8, * 9 and * 10, * 11 and * 12, and * 13. It may be either of the two ring-forming carbon atoms represented by * 14.
  • X 45 is C (R 4512 ) (R 4513 ), NR 4514 , oxygen atom or sulfur atom.
  • R 4501 to R 4506 and R 4512 to R 4513 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 4501 to R 4514 , which do not form the monocyclic ring and do not form the condensed ring, are independently synonymous with R 461 to R 471 in the general formula (45). )
  • * 1 and * 2, and * 3 and * 4 represent the two ring-forming carbon atoms to which R n and R n + 1 are bonded.
  • the ring-forming carbon atom to which R n is bonded may be either * 1 and * 2, or the two ring-forming carbon atoms represented by * 3 and * 4.
  • X 45 is C (R 4512 ) (R 4513 ), NR 4514 , oxygen atom or sulfur atom.
  • R 4512 to R 4513 and R 4515 to R 4525 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 4512 to R 4513 , R 4515 to R 4521, R 4522 to R 4525 , and R 4514 , which do not form the monocyclic ring and do not form the condensed ring, are independently R in the general formula (45). It is synonymous with 461 to R 471. )
  • R 462 , R 464 , R 465 , R 470 and R 471 preferably at least one of R 462 , R 465 and R 470 , more preferably R 462 .
  • the group does not form a ring structure.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A group represented by -N (R 906 ) (R 907), Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, It is either a substituted or unsubstituted heterocyclic group having 5 to 50 atoms, or a group selected from the group consisting of the groups represented by the following general formulas (461) to (464).
  • R d is independent of each other Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted
  • X 46 is C (R 801 ) (R 802 ), NR 803 , oxygen atom or sulfur atom.
  • R801 , R802 and R803 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • the * in the general formulas (461) to (464) independently indicate the bonding position with the ring structure.
  • R901 to R907 are as defined as described above.
  • the compound represented by the general formula (45) is represented by any of the following general formulas (45-1) to (45-6).
  • Rings d to i are independently substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings, respectively.
  • R 461 to R 471 are independently synonymous with R 461 to R 471 in the general formula (45).
  • the compound represented by the general formula (45) is represented by any of the following general formulas (45-7) to (45-12).
  • Rings d to f, k, and j are independently substituted or unsubstituted monocycles or substituted or unsubstituted fused rings, respectively.
  • R 461 to R 471 are independently synonymous with R 461 to R 471 in the general formula (45).
  • the compound represented by the general formula (45) is represented by any of the following general formulas (45-13) to (45-21).
  • Rings d to k are independently substituted or unsubstituted monocycles or substituted or unsubstituted fused rings, respectively.
  • R 461 to R 471 are independently synonymous with R 461 to R 471 in the general formula (45).
  • substituent when the ring g or the ring h further has a substituent include, for example.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, The group represented by the general formula (461), Examples thereof include a group represented by the general formula (463) or a group represented by the general formula (464).
  • the compound represented by the general formula (45) is represented by any of the following general formulas (45-22) to (45-25).
  • X 46 and X 47 are independently C (R 801 ) (R 802 ), NR 803 , oxygen atom or sulfur atom, respectively.
  • R 461 to R 471 and R 481 to R 488 are independently synonymous with R 461 to R 471 in the general formula (45).
  • R801 , R802 and R803 are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
  • R 801 there are a plurality a plurality of R 801 is the same or different from each other, If R 802 there are a plurality, a plurality of R 802 is the same or different from each other, If R 803 there are a plurality, a plurality of R 803 may or different are identical to one another. )
  • the compound represented by the general formula (45) is represented by the following general formula (45-26).
  • X 46 is C (R 801 ) (R 802 ), NR 803 , oxygen atom or sulfur atom.
  • R 463 , R 464 , R 467 , R 468 , R 471 , and R 481 to R 492 are independently synonymous with R 461 to R 471 in the general formula (45).
  • R801 , R802 and R803 are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
  • R 801 there are a plurality a plurality of R 801 is the same or different from each other, If R 802 there are a plurality, a plurality of R 802 is the same or different from each other, If R 803 there are a plurality, a plurality of R 803 may or different are identical to one another. )
  • R 501 to R 507 and R 511 to R 517 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 501 to R 507 and R 511 to R 517 , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms.
  • R 521 and R 522 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocycl
  • One set of two or more adjacent sets of R 501 to R 507 and R 511 to R 517 " is, for example, a set of R 501 and R 502 , a set of R 502 and R 503 , and R. It is a combination of a set of 503 and R 504 , a set of R 505 and R 506 , a set of R 506 and R 507 , a set of R 501 , R 502 and R 503, and the like.
  • At least one, preferably two , of R 501 to R 507 and R 511 to R 517 are groups represented by -N (R 906 ) (R 907).
  • R 501 to R 507 and R 511 to R 517 are independent of each other.
  • the compound represented by the general formula (5) is a compound represented by the following general formula (52).
  • R 531 to R 534 and R 541 to R 544 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 531 to R 534 , R 541 to R 544 , and R 551 and R 552 , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
  • Hydrogen atom A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • R 561 to R 564 are independent of each other.
  • the compound represented by the general formula (5) is a compound represented by the following general formula (53).
  • R 551 , R 552 and R 561 to R 564 are independently synonymous with R 551 , R 552 and R 561 to R 564 in the general formula (52), respectively.
  • R 561 to R 564 in the general formula (52) and the general formula (53) are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms (preferably phenyl groups). ).
  • R 521 and R 522 in the general formula (5) and R 551 and R 552 in the general formula (52) and the general formula (53) are hydrogen atoms.
  • the substituent in the case of "substitutable or unsubstituted" in the general formula (5), general formula (52) and general formula (53) is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms.
  • Ring a, ring b and ring c are independent of each other.
  • R 601 and R 602 independently combine with the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.
  • R601 and R602 which do not form the substituted or unsubstituted heterocycle, are independently Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms. )
  • Rings a, b, and c are rings (substituted or unsubstituted ring-forming carbon atoms 6 to 50) that are condensed into the fused bicyclic structure at the center of the general formula (6) composed of a boron atom and two nitrogen atoms.
  • the "aromatic hydrocarbon rings" of the a ring, b ring and c ring have the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group”.
  • the "aromatic hydrocarbon ring" of the a ring contains three carbon atoms on the condensed bicyclic structure at the center of the general formula (6) as ring-forming atoms.
  • the "aromatic hydrocarbon ring" of the b ring and the c ring contains two carbon atoms on the condensed bicyclic structure at the center of the general formula (6) as ring-forming atoms.
  • the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms” include a compound in which a hydrogen atom is introduced into the "aryl group” described in the specific example group G1.
  • the "heterocycle” of the a ring, b ring and c ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group”.
  • the "heterocycle” of the a ring contains three carbon atoms on the condensed bicyclic structure at the center of the general formula (6) as ring-forming atoms.
  • the "heterocycle" of the b ring and the c ring contains two carbon atoms on the condensed bicyclic structure at the center of the general formula (6) as ring-forming atoms.
  • Specific examples of the "heterocyclic ring having 5 to 50 substituted or unsubstituted ring-forming atoms” include a compound in which a hydrogen atom is introduced into the "heterocyclic group" described in the specific example group G2.
  • R 601 and R 602 may be independently bonded to the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle.
  • the heterocycle in this case contains a nitrogen atom on the condensed bicyclic structure at the center of the general formula (6).
  • the heterocycle in this case may contain a heteroatom other than the nitrogen atom.
  • R 601 may be bonded to the a ring to form a nitrogen-containing heterocycle in which the ring containing R 601 and the a ring are condensed (or three-ring condensation or more).
  • Specific examples of the nitrogen-containing heterocycle include compounds corresponding to heterocyclic groups containing nitrogen and having two or more ring condensations in the specific example group G2. The same applies when R 601 binds to the b ring, R 602 binds to the a ring, and R 602 binds to the c ring.
  • the a ring, b ring, and c ring in the general formula (6) are independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms. In one embodiment, the a ring, b ring and c ring in the general formula (6) are independently substituted or unsubstituted benzene rings or naphthalene rings, respectively.
  • R 601 and R 602 in the general formula (6) are independent of each other.
  • the compound represented by the general formula (6) is a compound represented by the following general formula (62).
  • R 601A combines with one or more selected from the group consisting of R 611 and R 621 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 602A combines with one or more selected from the group consisting of R 613 and R 614 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 601A and R 602A which do not form the substituted or unsubstituted heterocycle, are independently Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
  • R 611 to R 621 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 611 to R 621 , which do not form the substituted or unsubstituted heterocycle, do not form the monocycle, and do not form the condensed ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms. )
  • R 601A and R 602A of the general formula (62) are groups corresponding to R 601 and R 602 of the general formula (6), respectively.
  • R 601A and R 611 may be bonded to form a nitrogen-containing heterocycle in which a ring containing these and a benzene ring corresponding to the a ring are condensed to form a bicyclic condensation (or tricyclic condensation or more).
  • Specific examples of the nitrogen-containing heterocycle include compounds corresponding to heterocyclic groups containing nitrogen and having two or more ring condensations in the specific example group G2. The same applies to the case where R 601A and R 621 are combined, the case where R 602A and R 613 are combined, and the case where R 602A and R 614 are combined.
  • R 611 to R 621 may combine with each other to form a substituted or unsubstituted monocycle, or they may combine with each other to form a substituted or unsubstituted fused ring.
  • R 611 and R 612 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed with a 6-membered ring to which they are bonded.
  • the formed fused ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.
  • R 611 to R 621 which do not contribute to ring formation, are independent of each other.
  • R 611 to R 621 which do not contribute to ring formation, are independent of each other.
  • Hydrogen atom A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms.
  • R 611 to R 621 which do not contribute to ring formation, are independent of each other. It is a hydrogen atom or an substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 611 to R 621 which do not contribute to ring formation, are independent of each other.
  • At least one of R 611 to R 621 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the general formula (62) is a compound represented by the following general formula (63).
  • R 631 combines with R 646 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 633 combines with R 647 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 634 combines with R 651 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 641 combines with R 642 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 631 to R 651 Combine with each other to form a substituted or unsubstituted monocycle, Bond to each other to form substituted or unsubstituted fused rings, or not to each other R 631 to R 651 , which do not form the substituted or unsubstituted heterocycle, do not form the monocycle, and do not form the condensed ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903), A group represented by -O- (R 904), A group represented by -S- (R 905), A group represented by -N (R 906 ) (R 907), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms. )
  • R 631 may be combined with R 646 to form a substituted or unsubstituted heterocycle.
  • R 631 and R 646 are bonded to form a nitrogen-containing heterocycle having three or more ring condensations in which a benzene ring to which R 646 is bonded, a ring containing N, and a benzene ring corresponding to the a ring are condensed.
  • the nitrogen-containing heterocycle include compounds corresponding to heterocyclic groups containing nitrogen and having three or more ring condensations in the specific example group G2. The same applies when R 633 and R 647 are combined, when R 634 and R 651 are combined, and when R 641 and R 642 are combined.
  • R 631 to R 651 which do not contribute to ring formation, are independent of each other.
  • R 631 to R 651 which do not contribute to ring formation, are independent of each other.
  • Hydrogen atom A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atomic atoms.
  • R 631 to R 651 which do not contribute to ring formation, are independent of each other. It is a hydrogen atom or an substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 631 to R 651 which do not contribute to ring formation, are independent of each other.
  • At least one of R 631 to R 651 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63A).
  • R 661 is Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, A cycloalkyl group having 3 to 50 substituted or unsubstituted ring-forming carbon atoms, or an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms.
  • R 662 to R 665 are independent of each other.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms.
  • R 661 to R 665 are independent of each other.
  • R 661 to R 665 are independently substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63B).
  • R 671 and R 672 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A group represented by ⁇ N (R 906 ) (R 907 ), or an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 50.
  • R 673 to R 675 are independent of each other.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A group represented by ⁇ N (R 906 ) (R 907 ), or an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 50. )
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63B').
  • R 672 to R 675 are independently synonymous with R 672 to R 675 in the general formula (63B).
  • At least one of R 671 to R 675 Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A group represented by ⁇ N (R 906 ) (R 907 ), or an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 50.
  • R 672 is Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, A group represented by ⁇ N (R 906 ) (R 907 ), or an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 50.
  • R 671 and R 673 to R 675 are independent of each other.
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63C).
  • R 681 and R 682 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms. R 683 to R 686 are independent of each other.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms.
  • the compound represented by the general formula (63) is a compound represented by the following general formula (63C').
  • R 683 to R 686 are independently synonymous with R 683 to R 686 in the general formula (63C).
  • R 681 to R 686 are independent of each other.
  • R 681 to R 686 are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
  • an intermediate is first formed by binding the a ring, the b ring and the c ring with a linking group (a group containing N-R 601 and a group containing N-R 602).
  • the final product can be produced by producing (first reaction) and bonding the a ring, b ring and c ring with a linking group (group containing a boron atom) (second reaction).
  • first reaction an amination reaction such as the Buchwald-Hartwig reaction can be applied.
  • a tandem hetero Friedel-Crafts reaction or the like can be applied.

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PCT/JP2021/005077 2020-02-14 2021-02-10 有機エレクトロルミネッセンス素子及び電子機器 Ceased WO2021162057A1 (ja)

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US17/860,631 US20220393113A1 (en) 2020-02-14 2022-07-08 Organic electroluminescent element and electronic device
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WO2023190597A1 (ja) * 2022-03-29 2023-10-05 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器

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