WO2022270296A1 - Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device - Google Patents

Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device Download PDF

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WO2022270296A1
WO2022270296A1 PCT/JP2022/022952 JP2022022952W WO2022270296A1 WO 2022270296 A1 WO2022270296 A1 WO 2022270296A1 JP 2022022952 W JP2022022952 W JP 2022022952W WO 2022270296 A1 WO2022270296 A1 WO 2022270296A1
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group
substituted
ring
unsubstituted
single bond
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Japanese (ja)
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佑典 高橋
匡 羽毛田
将太 田中
拓人 深見
司 澤藤
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出光興産株式会社
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Priority to KR1020237043377A priority Critical patent/KR20240026282A/en
Priority to CN202280039275.9A priority patent/CN117480152A/en
Publication of WO2022270296A1 publication Critical patent/WO2022270296A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/156—Hole transporting layers comprising a multilayered structure
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

Definitions

  • the present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device including the organic electroluminescence device.
  • an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode.
  • an organic EL element When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes from the anode side into the light-emitting region. It emits light when the state returns to the ground state. Therefore, development of a material that efficiently transports electrons or holes to the light-emitting region and facilitates recombination of electrons and holes is important for obtaining high-performance organic EL devices.
  • Patent Documents 1 and 2 disclose compounds used as materials for organic electroluminescence elements.
  • the present invention has been made to solve the above problems, and provides a compound that further improves the performance of an organic EL device, an organic EL device with improved device performance, and an electronic device containing such an organic EL device. intended to provide
  • organic EL devices containing the compound represented by the following formula (1) have better performance. found to be improved.
  • the present invention provides a compound represented by formula (1) below.
  • N * is the central nitrogen atom
  • R 1A to R 5A , R 1B to R 5B , and R 1D to R 5D are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted 6 to 6 ring carbon atoms. 12 aryl groups.
  • R 1A to R 5A is a single bond that binds to *a; one selected from R 1B to R 5B is a single bond that bonds to *b; one selected from R 1D to R 5D is a single bond that bonds to *d; Adjacent two selected from R 1A to R 5A which are not single bonds, adjacent two selected from R 1B to R 5B which are not single bonds, and R 1D to R 5D which are not single bonds adjacent two are not bonded to each other and thus do not form a ring structure; Benzene ring A and benzene ring B are not crosslinked.
  • m is 0 or 1; However, when m is 0, *d is bound to the central nitrogen atom N * .
  • R 1C to R 4C , R 1U to R 8U and R 1V to R 8V are hydrogen atoms. however, one selected from R 1U to R 8U is a single bond that binds to *u; one selected from R 1V to R 8V is a single bond that binds to *v; Benzene ring B and naphthalene ring U and benzene ring C and naphthalene ring V are not crosslinked.
  • Ar is represented by any one of the following formulas (1-a) to (1-e). (In formula (1-a), ** represents the binding position to the above *d.
  • R 1 to R 5 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group. however, one selected from R 1 to R 5 is a single bond that bonds to *e, and the other one selected from R 1 to R 5 is a single bond that bonds to *f; adjacent two selected from R 1 to R 5 which are not single bonds are not bonded to each other and therefore do not form a ring structure; When m is 1, n is 1, and l is 0, the following (i) or (ii) is satisfied, When m is 1, n is 0, and l is 1, the following (iii) or (iv) is satisfied.
  • R 3D is a single bond bonded to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond bonded to *e;
  • one selected from R 1D , R 2D , R 4D and R 5D is a single bond that bonds to *d, and one selected from R 1 to R 5 is a single bond that bonds to *e .
  • R 3D is a single bond that bonds to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond that bonds to *f.
  • R 11 and Ar 12 are groups represented by the following formula (i). (In formula (i), *** represents the binding position.
  • R 11 to R 15 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms. however, Two adjacent groups selected from R 11 to R 15 and two adjacent groups selected from R 21 to R 25 may combine with each other to form a substituted or unsubstituted benzene ring.
  • n is an integer of 0 to 2, and when n is 0, (Ar 11 ) 0 represents a hydrogen atom; l is an integer of 0 to 2, and when l is 0, (Ar 12 ) 0 represents a hydrogen atom. ) (In formula (1-b), ** represents the binding position to the above *d.
  • R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • R 21 to R 28 is a single bond that bonds to *g
  • the other one selected from R 21 to R 28 is a single bond that bonds to *h
  • R 21 to Still another one selected from R 28 is a single bond attached to *i
  • Adjacent two groups selected from R 21 to R 28 which are not single bonds are not bonded to each other and therefore do not form a ring structure.
  • Ar 13 and Ar 14 are groups represented by the following formula (ii). (In formula (ii), *** represents the binding position.
  • R 31 to R 35 are hydrogen atoms.
  • R 41 to R 52 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • R 41 to R 52 is a single bond that bonds to *j
  • the other one selected from R 41 to R 52 is a single bond that bonds to *k
  • R 41 to Further one selected from R 52 is a single bond attached to *l
  • Adjacent two selected from R 41 to R 52 which are not single bonds are not bonded to each other and thus do not form a ring structure.
  • Ar 15 and Ar 16 are groups represented by the above formula (ii). q is 0 or 1, and when q is 0 (Ar 15 ) 0 represents a hydrogen atom; r is 0 or 1, and (Ar 16 ) 0 represents a hydrogen atom when r is 0; ) (In formula (1-d), ** represents the binding position to the above *d.
  • R 61 to R 70 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. however, One selected from R 61 to R 70 is a single bond that bonds to *m, the other one selected from R 61 to R 70 is a single bond that bonds to *n, and R 61 to Still another one selected from R 70 is a single bond attached to *o, Adjacent two groups selected from R 61 to R 70 which are not single bonds are not bonded to each other and therefore do not form a ring structure.
  • Ar 17 and Ar 18 are groups represented by the above formula (ii).
  • R 81 to R 88 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • R A and R B are each independently a methyl group or a substituted or unsubstituted phenyl group.
  • * p is bound to one selected from R 81 to R 88 , R A and R B ; when R A or R B is attached to *l, R A or R B attached to *l is a methylene group or a substituted or unsubstituted phenylene group; when one selected from R 81 to R 88 is bonded to *l, one selected from R 81 to R 88 bonded to *l is a single bond; Adjacent two selected from R 81 to R 88 which are not single bonds may be bonded to each other to form a substituted or unsubstituted benzene ring, * R A and R B that are not bonded to l may combine to form a spiro ring. ))
  • the present invention provides an organic EL device material containing the compound represented by the formula (1).
  • the present invention is an organic electroluminescent device comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer comprises a light-emitting layer, and at least one of the organic layers
  • an organic electroluminescence device in which one layer contains the compound represented by the formula (1).
  • the present invention provides an electronic device including the organic electroluminescence element.
  • An organic EL device containing the compound represented by formula (1) exhibits improved device performance.
  • FIG. 1 is a schematic diagram showing an example of a layer structure of an organic EL element according to one aspect of the present invention
  • FIG. FIG. 4 is a schematic diagram showing another example of the layer structure of the organic EL element according to one aspect of the present invention
  • FIG. 4 is a schematic diagram showing another example of the layer structure of the organic EL element according to one aspect of the present invention
  • a hydrogen atom includes isotopes with different neutron numbers, ie, protium, deuterium, and tritium.
  • a hydrogen atom that is, a hydrogen atom, a deuterium atom, or Assume that the tritium atoms are bonded.
  • the number of ring-forming carbon atoms refers to the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). represents the number of carbon atoms among the atoms that When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same applies to the "number of ring-forming carbon atoms" described below unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms
  • the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
  • the number of ring-forming carbon atoms in the benzene ring substituted with the alkyl group is 6.
  • the naphthalene ring substituted with an alkyl group has 10 ring-forming carbon atoms.
  • the number of ring-forming atoms refers to compounds (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compound, and heterocyclic compound) represents the number of atoms constituting the ring itself. Atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom that constitutes a ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below unless otherwise specified.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of atoms forming the pyridine ring. Therefore, the number of ring-forming atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is 6.
  • the expression "substituted or unsubstituted XX to YY carbon number ZZ group” represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in the substituents.
  • "YY” is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and "YY” means an integer of 2 or more.
  • an unsubstituted ZZ group represents a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group is a "substituted or unsubstituted ZZ group”. is a "substituted ZZ group”.
  • "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
  • a hydrogen atom in the "unsubstituted ZZ group” is a protium atom, a deuterium atom, or a tritium atom.
  • substituted in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substituted in the case of "a BB group substituted with an AA group” similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the number of ring-forming carbon atoms in the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
  • the number of ring-forming atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified. be.
  • the number of carbon atoms in the "unsubstituted alkyl group” described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
  • the number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified. be.
  • the number of ring-forming carbon atoms of the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
  • the number of ring-forming atoms of the "unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5, unless otherwise specified herein. ⁇ 18.
  • the number of carbon atoms in the "unsubstituted alkylene group” described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
  • unsubstituted aryl group refers to the case where "substituted or unsubstituted aryl group” is “unsubstituted aryl group", and substituted aryl group is “substituted or unsubstituted aryl group” It refers to a "substituted aryl group”.
  • aryl group includes both "unsubstituted aryl group” and “substituted aryl group”.
  • a "substituted aryl group” means a group in which one or more hydrogen atoms of an "unsubstituted aryl group” are replaced with a substituent.
  • substituted aryl group examples include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group” of Specific Example Group G1A below is replaced with a substituent, and a substituted aryl group of Specific Example Group G1B below.
  • Examples include:
  • the examples of the "unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are only examples, and the “substituted aryl group” described herein includes the following specific examples A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group” of Group G1B is further replaced with a substituent, and the hydrogen atom of the substituent in the "substituted aryl group” of Specific Example Group G1B below Furthermore, groups substituted with substituents are also included.
  • aryl group (specific example group G1A): phenyl group, a p-biphenyl group, m-biphenyl group, an o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chryseny
  • Substituted aryl group (specific example group G1B): an o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, an ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, an ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl) fluorenyl group, a cyanophenyl group, a
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
  • a “heterocyclic group” as described herein is a monocyclic group or a condensed ring group.
  • a “heterocyclic group” as described herein is either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • specific examples of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic groups (specific example group G2A), and substituted heterocyclic groups ( Specific example group G2B) and the like can be mentioned.
  • unsubstituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”, and substituted heterocyclic group refers to “substituted or unsubstituted "Heterocyclic group” refers to a "substituted heterocyclic group”.
  • heterocyclic group refers to a "substituted heterocyclic group”.
  • a “substituted heterocyclic group” means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” of the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups of the following specific example group G2B. mentioned.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are only examples, and the "substituted heterocyclic group” described herein specifically includes A group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of Example Group G2B is further replaced with a substituent, and a substituent in the "substituted heterocyclic group" of Specific Example Group G2B A group in which the hydrogen atom of is further replaced with a substituent is also included.
  • Specific example group G2A includes, for example, the following nitrogen atom-containing unsubstituted heterocyclic groups (specific example group G2A1), oxygen atom-containing unsubstituted heterocyclic groups (specific example group G2A2), sulfur atom-containing unsubstituted (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • nitrogen atom-containing unsubstituted heterocyclic groups specifically example group G2A1
  • oxygen atom-containing unsubstituted heterocyclic groups specifically example group G2A2
  • sulfur atom-containing unsubstituted specifically example group G2A3
  • a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), substituted heterocyclic group containing an oxygen atom (specific example group G2B2), substituted heterocyclic ring containing a sulfur atom group (specific example group G2B3), and one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) as a substituent Including substituted groups (example group G2B4).
  • an unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, quinolyl group, an isoquinolyl group, cinnolyl group, a phthalazinyl group, a quinazolinyl
  • an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, azanaphthobenzofuranyl group and diazanaphthobenzofuranyl group;
  • thienyl group an unsubstituted heterocyclic group containing a sulfur atom
  • thienyl group a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothiopheny
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic groups derived from the represented ring structures include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 .
  • a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl) phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group and a biphenylylquinazolinyl group;
  • a substituted heterocyclic group containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, A t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
  • a substituted heterocyclic group containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
  • the "one or more hydrogen atoms of the monovalent heterocyclic group” means that at least one of the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, XA and YA is NH.
  • unsubstituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is “unsubstituted alkyl group”
  • substituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is It refers to a "substituted alkyl group”.
  • alkyl group includes both an "unsubstituted alkyl group” and a "substituted alkyl group”.
  • a “substituted alkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group” (specific example group G3A) are replaced with substituents, and substituted alkyl groups (specific examples Examples of group G3B) and the like can be mentioned.
  • the alkyl group in the "unsubstituted alkyl group” means a chain alkyl group.
  • the "unsubstituted alkyl group” includes a linear “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are only examples, and the "substituted alkyl group” described herein includes specific example group G3B A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group” of Specific Example Group G3B is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group” of Specific Example Group G3B is further replaced by a substituent included.
  • Unsubstituted alkyl group (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group.
  • Substituted alkyl group (specific example group G3B): a heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group;
  • Substituted or unsubstituted alkenyl group Specific examples of the "substituted or unsubstituted alkenyl group" described in the specification (specific example group G4) include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B) and the like.
  • unsubstituted alkenyl group refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group", "substituted alkenyl group” means "substituted or unsubstituted alkenyl group ” is a “substituted alkenyl group”.
  • alkenyl group simply referring to an “alkenyl group” includes both an “unsubstituted alkenyl group” and a “substituted alkenyl group”.
  • a “substituted alkenyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include groups in which the following "unsubstituted alkenyl group” (specific example group G4A) has a substituent, and substituted alkenyl groups (specific example group G4B). be done.
  • Unsubstituted alkenyl group (specific example group G4A): a vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.
  • Substituted alkenyl group (specific example group G4B): 1,3-butandienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, a 2-methylallyl group and a 1,2-dimethylallyl group;
  • Substituted or unsubstituted alkynyl group Specific examples of the "substituted or unsubstituted alkynyl group" described in the specification (specific example group G5) include the following unsubstituted alkynyl groups (specific example group G5A).
  • unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group” is "unsubstituted alkynyl group”.
  • alkynyl group means "unsubstituted includes both "alkynyl group” and "substituted alkynyl group”.
  • a “substituted alkynyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group” (specific example group G5A) are replaced with substituents.
  • Substituted or unsubstituted cycloalkyl group Specific examples of the "substituted or unsubstituted cycloalkyl group” described in the specification (specific example group G6) include the following unsubstituted cycloalkyl groups (specific example group G6A), and substituted cycloalkyl groups ( Specific example group G6B) and the like can be mentioned.
  • unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group” is “unsubstituted cycloalkyl group", and substituted cycloalkyl group refers to "substituted or unsubstituted It refers to the case where "cycloalkyl group” is “substituted cycloalkyl group”.
  • cycloalkyl group means "unsubstituted cycloalkyl group” and “substituted cycloalkyl group”. including both.
  • a “substituted cycloalkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group” (specific example group G6A) are replaced with substituents, and substituted cycloalkyl groups (Specific example group G6B) and the like.
  • the examples of the "unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed here are only examples, and the "substituted cycloalkyl group” described herein specifically includes A group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the “substituted cycloalkyl group” of Example Group G6B is replaced with a substituent, and in the “substituted cycloalkyl group” of Specific Example Group G6B A group in which a hydrogen atom of a substituent is further replaced with a substituent is also included.
  • cycloalkyl group (specific example group G6A): a cyclopropyl group, cyclobutyl group, a cyclopentyl group, a cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • cycloalkyl group (specific example group G6B): 4-methylcyclohexyl group;
  • G7 A group represented by -Si (R 901 ) (R 902 ) (R 903 )
  • Specific examples of the group represented by —Si(R 901 )(R 902 )(R 903 ) described in the specification include: -Si(G1)(G1)(G1), - Si (G1) (G2) (G2), - Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3) and -Si(G6)(G6)(G6) is mentioned.
  • G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G1's in -Si(G1)(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -Si (G1) (G2) (G2) are the same or different from each other.
  • a plurality of G1's in -Si(G1)(G1)(G2) are the same or different from each other.
  • a plurality of G2 in -Si(G2)(G2)(G2) are the same or different from each other.
  • a plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other.
  • a plurality of G6 in -Si(G6)(G6)(G6) are the same or different from each other.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G9 A group represented by -S- (R 905 )
  • Specific examples of the group represented by -S-(R 905 ) described in the specification include: -S(G1), -S(G2), -S (G3) and -S (G6) is mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G1's in -N(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -N(G2)(G2) are the same or different from each other.
  • a plurality of G3s in -N(G3)(G3) are the same or different from each other.
  • a plurality of G6 in -N(G6)(G6) are the same or different from each other.
  • halogen atom described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • the "substituted or unsubstituted fluoroalkyl group” described in this specification means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a fluorine atom. Also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with fluorine atoms.
  • the carbon number of the “unsubstituted fluoroalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • a "substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of a “fluoroalkyl group” are replaced with a substituent.
  • substituted fluoroalkyl group described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and A group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group” is further replaced with a substituent is also included.
  • Specific examples of the "unsubstituted fluoroalkyl group” include groups in which one or more hydrogen atoms in the above “alkyl group” (specific example group G3) are replaced with fluorine atoms.
  • Substituted or unsubstituted haloalkyl group "Substituted or unsubstituted haloalkyl group” described herein means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom Also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the carbon number of the “unsubstituted haloalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • a "substituted haloalkyl group” means a group in which one or more hydrogen atoms of a “haloalkyl group” are replaced with a substituent.
  • the "substituted haloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent group, and a “substituted A group in which one or more hydrogen atoms of the substituent in the "haloalkyl group of" is further replaced with a substituent is also included.
  • Specific examples of the "unsubstituted haloalkyl group” include groups in which one or more hydrogen atoms in the above “alkyl group” (specific example group G3) are replaced with halogen atoms.
  • a haloalkyl group may be referred to as a halogenated alkyl group.
  • Substituted or unsubstituted alkoxy group A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group".
  • the carbon number of the "unsubstituted alkoxy group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • Substituted or unsubstituted alkylthio group A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), wherein G3 is the "substituted or unsubstituted alkyl group".
  • the carbon number of the “unsubstituted alkylthio group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • Substituted or unsubstituted aryloxy group Specific examples of the “substituted or unsubstituted aryloxy group” described in this specification are groups represented by —O(G1), where G1 is the “substituted or an unsubstituted aryl group”.
  • the number of ring-forming carbon atoms in the "unsubstituted aryloxy group” is 6-50, preferably 6-30, more preferably 6-18, unless otherwise specified in the specification.
  • ⁇ "Substituted or unsubstituted trialkylsilyl group” Specific examples of the "trialkylsilyl group” described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the group described in Specific Example Group G3. It is a "substituted or unsubstituted alkyl group”. A plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group” is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified in the specification.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the group described in Specific Example Group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • an "aralkyl group” is a group in which a hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one aspect of a “substituted alkyl group”.
  • An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group", and the number of carbon atoms in the "unsubstituted aralkyl group” is unless otherwise specified herein. , 7-50, preferably 7-30, more preferably 7-18.
  • substituted or unsubstituted aralkyl group include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • a substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl- 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group,
  • substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenyl, unless otherwise stated herein.
  • nantholinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-
  • a carbazolyl group is specifically any one of the following groups unless otherwise specified in the specification.
  • the (9-phenyl)carbazolyl group is specifically any one of the following groups, unless otherwise stated in the specification.
  • a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t- butyl group and the like.
  • the "substituted or unsubstituted arylene group” described herein is derived from the above "substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. is the base of the valence.
  • Specific examples of the “substituted or unsubstituted arylene group” include the “substituted or unsubstituted aryl group” described in specific example group G1 by removing one hydrogen atom on the aryl ring. Induced divalent groups and the like can be mentioned.
  • Substituted or unsubstituted divalent heterocyclic group Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group” described herein is the above “substituted or unsubstituted heterocyclic group” except that one hydrogen atom on the heterocyclic ring is removed. is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocyclic ring from the "substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include divalent groups derived by removing atoms.
  • Substituted or unsubstituted alkylene group Unless otherwise specified, the "substituted or unsubstituted alkylene group” described herein is derived from the above “substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. is the base of the valence. Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include the “substituted or unsubstituted alkyl group” described in specific example group G3 by removing one hydrogen atom on the alkyl chain. Induced divalent groups and the like can be mentioned.
  • the substituted or unsubstituted arylene group described in this specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • * represents a binding position.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Formulas Q9 and Q10 may be linked together through a single bond to form a ring.
  • * represents a binding position.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents a binding position.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein is.
  • Q 1 to Q 9 are each independently a hydrogen atom or a substituent.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • R 921 and R 922 when “one or more pairs of two or more adjacent pairs of R 921 to R 930 are combined to form a ring", is a pair of R 921 and R 922 , a pair of R 922 and R 923 , a pair of R 923 and R 924 , a pair of R 924 and R 930 , a pair of R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R 929 and R 921 .
  • one or more pairs means that two or more of the groups consisting of two or more adjacent groups may form a ring at the same time.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 925 and R 926 are bonded together to form ring Q B
  • the general formula (TEMP-103) The represented anthracene compound is represented by the following general formula (TEMP-104).
  • a group consisting of two or more adjacent pairs forms a ring is not limited to the case where a group consisting of two adjacent "two” is combined as in the above example, but It also includes the case where a pair is combined.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 922 and R 923 are bonded together to form ring Q C
  • the adjacent three R 921 , R 922 and R 923
  • the anthracene compound represented by the general formula (TEMP-103) has It is represented by the general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “condensed ring” to be formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when “one pair of adjacent pairs" forms a “single ring” or a “fused ring", the “single ring” or “fused ring” is a saturated ring, or Unsaturated rings can be formed.
  • ring Q A and ring Q B formed in the general formula (TEMP-104) are each a “monocyclic ring” or a "fused ring”.
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) form a condensed ring by condensing the ring Q A and the ring Q C. If the ring Q A in the general formula (TEMP-104) is a benzene ring, the ring Q A is monocyclic. When the ring Q A of the general formula (TEMP-104) is a naphthalene ring, the ring Q A is a condensed ring.
  • Unsaturated ring means an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a “saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.
  • Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in the specific example group G1 are terminated with a hydrogen atom.
  • Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups listed as specific examples in the specific example group G2 are terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in the specific example group G6 are terminated with a hydrogen atom.
  • Forming a ring means forming a ring only with a plurality of atoms of the mother skeleton, or with a plurality of atoms of the mother skeleton and one or more arbitrary elements.
  • the ring Q A formed by combining R 921 and R 922 shown in the general formula (TEMP-104) has the carbon atom of the anthracene skeleton to which R 921 is bonded and the anthracene skeleton to which R 922 is bonded. It means a ring formed by a skeleton carbon atom and one or more arbitrary elements.
  • R 921 and R 922 form a ring Q A , the carbon atom of the anthracene skeleton to which R 921 is bound, the carbon atom of the anthracene skeleton to which R 922 is bound, and four carbon atoms and form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.
  • the "arbitrary element” is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise specified in this specification.
  • a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an “optional substituent” described later.
  • the ring formed is a heterocycle.
  • One or more arbitrary elements constituting a monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, unless otherwise specified in the present specification. , more preferably 3 or more and 5 or less.
  • “monocyclic ring” and “condensed ring” “monocyclic ring” is preferred, unless otherwise stated in the present specification.
  • the “saturated ring” and the “unsaturated ring” the “unsaturated ring” is preferred, unless otherwise specified in the present specification.
  • “monocyclic” is preferably a benzene ring.
  • the “unsaturated ring” is preferably a benzene ring.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above “monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section “Substituents described herein” above.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above "monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section "Substituents described herein" above. The above is the case where “one or more pairs of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic ring", and “one or more pairs of two or more adjacent pairs are combined with each other to form a substituted or unsubstituted condensed ring"("combine to form a ring").
  • the substituent in the case of “substituted or unsubstituted” is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R 901 ) (R 902 ) (R 903 ), —O—(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), halogen atom, cyano group, nitro group, a group selected from the group consisting of an unsubstituted aryl group
  • the two or more R 901 are the same or different from each other, when two or more R 902 are present, the two or more R 902 are the same or different from each other; when two or more R 903 are present, the two or more R 903 are the same or different from each other, when two or more R 904 are present, the two or more R 904 are the same or different from each other; when two or more R 905 are present, the two or more R 905 are the same or different from each other, when two or more R 906 are present, the two or more R 906 are the same or different from each other; When two or more R 907 are present, the two or more R 907 are the same or different from each other.
  • the substituents referred to above as "substituted or unsubstituted” are an alkyl group having 1 to 50 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituents referred to above as "substituted or unsubstituted” are an alkyl group having 1 to 18 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may form a “saturated ring” or an “unsaturated ring”, preferably a substituted or unsubstituted saturated 5 forming a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
  • any substituent may have further substituents. Substituents further possessed by the optional substituents are the same as the above optional substituents.
  • the numerical range represented using “AA to BB” has the numerical value AA described before “AA to BB” as the lower limit, and the numerical value BB described after “AA to BB” as the upper limit.
  • invention compounds The compounds of the present invention are described below.
  • the compound of the present invention is represented by the following formula (1).
  • the compounds of the present invention represented by formula (1) and formulas included in formula (1) described later may be simply referred to as "invention compounds”.
  • N * is the central nitrogen atom
  • R 1A to R 5A , R 1B to R 5B , and R 1D to R 5D are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted 6 to 6 ring carbon atoms. 12 aryl groups.
  • R 1A to R 5A is a single bond that binds to *a; one selected from R 1B to R 5B is a single bond that bonds to *b; one selected from R 1D to R 5D is a single bond that bonds to *d; Adjacent two selected from R 1A to R 5A which are not single bonds, adjacent two selected from R 1B to R 5B which are not single bonds, and R 1D to R 5D which are not single bonds adjacent two are not bonded to each other and thus do not form a ring structure; Benzene ring A and benzene ring B are not crosslinked.
  • the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 1A to R 5A , R 1B to R 5B and R 1D to R 5D is preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group or t-butyl group, more preferably methyl group, ethyl group, isopropyl group or t-butyl group, still more preferably methyl group or t-butyl group is the base.
  • the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R 1A to R 5A , R 1B to R 5B and R 1D to R 5D is preferably a phenyl group, a biphenylyl group or a naphthyl group. , more preferably a phenyl group or a naphthyl group, and still more preferably a phenyl group.
  • R 3A is preferably a single bond attached to *a.
  • one selected from R 2B to R 4B is preferably a single bond that bonds to *b, and R 3B is more preferably a single bond that bonds to *b.
  • one selected from R 2D to R 4D is preferably a single bond that bonds to *d, and R 3D is more preferably a single bond that bonds to *d.
  • R 1A to R 5A that are not single bonds, R 1B to R 5B that are not single bonds, and R 1D to R 5D that are not single bonds are preferably hydrogen atoms.
  • n is 0 or 1; However, when m is 0, *d is bound to the central nitrogen atom N * . In one aspect of the present invention, m is preferably 0. In another aspect of the invention, m is preferably one.
  • R 1C to R 4C , R 1U to R 8U and R 1V to R 8V are hydrogen atoms. however, one selected from R 1U to R 8U is a single bond that binds to *u; one selected from R 1V to R 8V is a single bond that binds to *v; Benzene ring B and naphthalene ring U and benzene ring C and naphthalene ring V are not crosslinked.
  • one selected from R 1U , R 4U , R 5U and R 8U is preferably a single bond that binds to *u. In one aspect of the present invention, one selected from R 1V , R 4V , R 5V and R 8V is preferably a single bond that binds to *v.
  • Ar is represented by any one of the following formulas (1-a) to (1-e).
  • R 1 to R 5 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group.
  • one selected from R 1 to R 5 is a single bond that bonds to *e, and the other one selected from R 1 to R 5 is a single bond that bonds to *f; adjacent two selected from R 1 to R 5 which are not single bonds are not bonded to each other and therefore do not form a ring structure;
  • m 1, n is 1, and l is 0, the following (i) or (ii) is satisfied,
  • m 1, n is 0, and l is 1, the following (iii) or (iv) is satisfied.
  • R 3D is a single bond bonded to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond bonded to *e;
  • one selected from R 1D , R 2D , R 4D and R 5D is a single bond that bonds to *d, and one selected from R 1 to R 5 is a single bond that bonds to *e .
  • R 3D is a single bond that bonds to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond that bonds to *f.
  • one selected from R 1D , R 2D , R 4D and R 5D is a single bond that binds to *d, and one selected from R 1 to R 5 is a single bond that binds to *f .
  • R 1 to R 5 The unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 1 to R 5 is as described above for R 1A to R 5A , R 1B to R 5B , and R 1D to R 5D . is the same.
  • R 1 to R 5 that are not single bonds are preferably hydrogen atoms.
  • Ar 11 and Ar 12 are groups represented by the following formula (i).
  • R 11 to R 15 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms. however, Two adjacent groups selected from R 11 to R 15 and two adjacent groups selected from R 21 to R 25 may combine with each other to form a substituted or unsubstituted benzene ring.
  • the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 11 to R 15 is as described above for R 1A to R 5A , R 1B to R 5B and R 1D to R 5D . is the same.
  • R 11 to R 15 that are not single bonds are preferably hydrogen atoms.
  • n may be 0, in another aspect of the invention, n may be 1, and in yet another aspect of the invention, n may be 2. .
  • l may be 0, in another aspect of the invention, l may be 1, and in yet another aspect of the invention, l may be 2. .
  • Formula (1-a) is preferably represented by the following formula.
  • R is omitted for simplification.
  • R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. however, One selected from R 21 to R 28 is a single bond that bonds to *g, the other one selected from R 21 to R 28 is a single bond that bonds to *h, and R 21 to Still another one selected from R 28 is a single bond attached to *i, Adjacent two groups selected from R 21 to R 28 which are not single bonds are not bonded to each other and therefore do not form a ring structure.
  • the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 21 to R 28 is preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl or t-butyl group, more preferably methyl group, ethyl group, isopropyl group, or t-butyl group, still more preferably methyl group or t-butyl group.
  • the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by R 21 to R 28 is preferably a phenyl group, a biphenylyl group or a naphthyl group, more preferably a phenyl group or a naphthyl group. and more preferably a phenyl group.
  • R 21 to R 28 which are not single bonds are preferably hydrogen atoms.
  • one selected from R 21 , R 24 , R 25 and R 28 is preferably a single bond that bonds to *g.
  • the other one selected from R 21 , R 24 , R 25 and R 28 is preferably a single bond that binds to *h, and R 21 , R 24 and R 25 , and R 28 is preferably a single bond that bonds to *i.
  • Ar 13 and Ar 14 are groups represented by the following formula (ii).
  • R 31 to R 35 are hydrogen atoms.
  • o is 0 or 1, and when o is 0 (Ar 13 ) 0 represents a hydrogen atom; p is 0 or 1, and (Ar 14 ) 0 represents a hydrogen atom when p is 0;
  • o may be 0, and in another aspect of the invention, o may be 1. In one aspect of the invention, p may be 0, and in another aspect of the invention, p may be 1.
  • R 41 to R 52 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. however, One selected from R 41 to R 52 is a single bond that bonds to *j, the other one selected from R 41 to R 52 is a single bond that bonds to *k, and R 41 to Further one selected from R 52 is a single bond attached to *l, Adjacent two selected from R 41 to R 52 which are not single bonds are not bonded to each other and thus do not form a ring structure.
  • the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 41 to R 52 is as described above for R 21 to R 28 , and the preferred groups are also the same.
  • the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by R 41 to R 52 is as described above for R 21 to R 28 , and preferred groups are also the same.
  • R 41 to R 52 that are not single bonds are preferably hydrogen atoms.
  • Ar 15 and Ar 16 are groups represented by the above formula (ii). q is 0 or 1, and when q is 0 (Ar 15 ) 0 represents a hydrogen atom; r is 0 or 1, and (Ar 16 ) 0 represents a hydrogen atom when r is 0;
  • q may be 0, and in another aspect of the invention, q may be 1.
  • r may be 0, and in another aspect of the invention, r may be 1.
  • R 61 to R 70 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. however, One selected from R 61 to R 70 is a single bond that bonds to *m, the other one selected from R 61 to R 70 is a single bond that bonds to *n, and R 61 to Still another one selected from R 70 is a single bond attached to *o, Adjacent two groups selected from R 61 to R 70 which are not single bonds are not bonded to each other and therefore do not form a ring structure.
  • the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 61 to R 70 is as described above for R 21 to R 28 , and the preferred groups are also the same.
  • the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by R 61 to R 70 is as described above for R 21 to R 28 , and preferred groups are also the same.
  • R 61 to R 70 which are not single bonds are preferably hydrogen atoms.
  • one selected from R 69 and R 70 is preferably a single bond that bonds to *m. In one aspect of the present invention, the other one selected from R 69 and R 70 is preferably a single bond that binds to *n or *o.
  • Ar 17 and Ar 18 are groups represented by the above formula (ii). s is 0 or 1, and when s is 0 (Ar 17 ) 0 represents a hydrogen atom, t is 0 or 1, and (Ar 18 ) 0 represents a hydrogen atom when t is 0;
  • s may be 0, and in another aspect of the invention, s may be 1.
  • t may be 0, and in another aspect of the invention, t may be 1.
  • R 81 to R 88 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • R A and R B are each independently a methyl group or a substituted or unsubstituted phenyl group.
  • * p is bound to one selected from R 81 to R 88 , R A and R B ; when R A or R B is attached to *l, R A or R B attached to *l is a methylene group or a substituted or unsubstituted phenylene group; when one selected from R 81 to R 88 is bonded to *l, one selected from R 81 to R 88 bonded to *l is a single bond; Adjacent two selected from R 81 to R 88 which are not single bonds may be bonded to each other to form a substituted or unsubstituted benzene ring, * R A and R B that are not bonded to l may combine to form a spiro ring.
  • the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 81 to R 88 is as described above for R 21 to R 28 , and the preferred groups are also the same.
  • the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by R 81 to R 88 is as described above for R 21 to R 28 , and preferred groups are also the same.
  • R A and R B may be a methyl group or a substituted or unsubstituted phenyl group, one being a methyl group and the other being a substituted or unsubstituted phenyl may be a base.
  • Ar is preferably represented by the formula (1-a), (1-b) or (1-d), more preferably represented by the formula (1-b) or (1-d) preferable.
  • m is preferably 0 when Ar is represented by the formula (1-b).
  • m is preferably 1 when Ar is represented by formula (1-a) or (1-d).
  • the invention compound is preferably a compound represented by the following formula (1-1), more preferably a compound represented by the following formula (1-2).
  • N * , R1A to R5A , R1B to R5B, R1C to R4C, R1D to R5D, R2U to R8U, R1V to R7V , Ar , m , * a , *b, * d, benzene ring A to benzene ring D, naphthalene ring U, and naphthalene ring V are as defined in formula (1).
  • (A-1) All of R 1A to R 5A that are not single bonds bonded to *a may be hydrogen atoms
  • All of R 1B to R 5B that are not single bonds bonded to *b may be hydrogen atoms
  • (A-3) all of R 1C to R 4C may be hydrogen atoms
  • All of R 1D to R 5D that are not single bonds bonded to *d may be hydrogen atoms
  • (A-5) All of R 1U to R 8U that are not single bonds bonded to *u may be hydrogen atoms
  • All of R 1V to R 8V that are not single bonds bonded to *v may be hydrogen atoms
  • (A-7) all of R 1 to R 5 that are not single bonds bonded to *e and *f may be hydrogen atoms
  • (A-8) all of R 11 to R 15 may be hydrogen atoms
  • hydrogen atom as used herein includes protium, deuterium, and tritium atoms. Accordingly, invention compounds may contain naturally occurring deuterium atoms. Alternatively, deuterium atoms may be intentionally introduced into the invention compound A by using a deuterated compound as part or all of the raw material compound. Accordingly, in one aspect of the invention, the compounds of the invention contain at least one deuterium atom. That is, the compound of the invention may be a compound represented by formula (1) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.
  • the deuteration rate of the invention compound depends on the deuteration rate of the starting compound used. Even if a raw material with a given deuteration rate is used, it may still contain a certain proportion of natural proton isotopes. Therefore, the aspect of the deuteration rate of the compound of the invention shown below is the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula, and the ratio in consideration of trace isotopes derived from nature. included.
  • the deuteration rate of the compound of the invention is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more.
  • Invention compounds may be mixtures containing deuterated and non-deuterated compounds, mixtures of two or more compounds having different deuteration rates.
  • the deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and 100% or more. %.
  • the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the invention is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more, and 100 % or less.
  • Invention compounds can be easily produced by those skilled in the art by referring to the following synthesis examples and known synthesis methods.
  • D represents a deuterium atom.
  • the organic EL device material that is one aspect of the present invention contains the invention compound.
  • the content of the invention compound in the organic EL device material is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), and 50% by mass or more (including 100% more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%).
  • the organic EL device material, which is one aspect of the present invention, is useful for manufacturing organic EL devices.
  • Organic EL Element that is one aspect of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layers comprise a light-emitting layer, and at least one layer of the organic layers comprises an invention compound.
  • the organic layer containing the compound of the invention include a hole-transporting zone provided between the anode and the light-emitting layer (hole-injection layer, hole-transporting layer, electron-blocking layer, exciton-blocking layer, etc.), light-emitting layer .
  • the inventive compound is preferably a material for the hole-transporting zone or light-emitting layer of a fluorescent or phosphorescent EL device, more preferably a material for the hole-transporting zone, even more preferably a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, or an excitation layer. It is used as a material for electron-blocking layers, particularly preferably as a material for hole-injecting layers or hole-transporting layers.
  • the organic EL device may be a fluorescent or phosphorescent monochromatic light emitting device, a fluorescent/phosphorescent hybrid white light emitting device, or a simple type having a single light emitting unit. However, it may be of a tandem type having a plurality of light-emitting units, and among these, it is preferably a fluorescent light-emitting device.
  • the term “light-emitting unit” refers to a minimum unit that includes organic layers, at least one layer of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.
  • the light-emitting unit may be of a multilayer type having a plurality of phosphorescent-emitting layers or fluorescent-emitting layers.
  • a space layer may be provided for the purpose of preventing the excitons from diffusing into the fluorescence-emitting layer.
  • a typical layer structure of a simple light-emitting unit is shown below. Layers in brackets are optional.
  • Each of the phosphorescent or fluorescent light-emitting layers may exhibit different emission colors.
  • (hole injection layer/) hole transport layer/first phosphorescent-emitting layer (red emission)/second phosphorescent-emitting layer (green emission)/space layer/fluorescence emission examples thereof include a layer structure such as layer (blue light emitting)/electron transport layer.
  • An electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or space layer.
  • a hole-blocking layer may be appropriately provided between each light-emitting layer and the electron-transporting layer.
  • an electron-blocking layer or a hole-blocking layer By providing an electron-blocking layer or a hole-blocking layer, electrons or holes can be confined in the light-emitting layer, the probability of charge recombination in the light-emitting layer can be increased, and the light-emitting efficiency can be improved.
  • the first light-emitting unit and the second light-emitting unit can be independently selected from the light-emitting units described above, for example.
  • the intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron withdrawal layer, a connection layer, or an intermediate insulating layer, and provides electrons to the first light-emitting unit and holes to the second light-emitting unit.
  • Known material configurations can be used to supply.
  • FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL element according to one aspect of the present invention.
  • the organic EL element 1 has a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 10 arranged between the anode 3 and the cathode 4 .
  • the light-emitting unit 10 has a light-emitting layer 5 .
  • a hole transport zone 6 (a hole injection layer, a hole transport layer, etc.) is provided between the light emitting layer 5 and the anode 3
  • an electron transport zone 7 an electron injection layer, an electron transport layer, etc. is provided between the light emitting layer 5 and the cathode 4. etc.).
  • an electron blocking layer (not shown) and a hole blocking layer (not shown) may be provided on the anode 3 side of the light emitting layer 5 and the cathode 4 side of the light emitting layer 5, respectively.
  • electrons and holes can be confined in the light-emitting layer 5, and the exciton generation efficiency in the light-emitting layer 5 can be further increased.
  • FIG. 2 is a schematic diagram showing another configuration of the organic EL element according to one aspect of the present invention.
  • the organic EL element 11 has a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 20 arranged between the anode 3 and the cathode 4 .
  • the light-emitting unit 20 has a light-emitting layer 5 .
  • a hole-transporting zone located between the anode 3 and the light-emitting layer 5 is formed from a hole-injecting layer 6a, a first hole-transporting layer 6b and a second hole-transporting layer 6c.
  • the electron-transporting zone located between the light-emitting layer 5 and the cathode 4 is formed of a first electron-transporting layer 7a and a second electron-transporting layer 7b.
  • FIG. 3 is a schematic diagram showing another configuration of the organic EL element according to one aspect of the present invention.
  • the organic EL element 12 has a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 30 arranged between the anode 3 and the cathode 4 .
  • the light-emitting unit 30 has a light-emitting layer 5 .
  • a hole-transporting zone located between the anode 3 and the light-emitting layer 5 is formed from a hole-injecting layer 6a, a first hole-transporting layer 6b, a second hole-transporting layer 6c and a third hole-transporting layer 6d.
  • the electron-transporting zone located between the light-emitting layer 5 and the cathode 4 is formed of a first electron-transporting layer 7a and a second electron-transporting layer 7b.
  • a host combined with a fluorescent dopant material is called a fluorescent host
  • a host combined with a phosphorescent dopant material is called a phosphorescent host.
  • Fluorescent hosts and phosphorescent hosts are not distinguished only by molecular structure. That is, the phosphorescent host means a material that contains a phosphorescent dopant and forms a phosphorescent light-emitting layer, and does not mean that it cannot be used as a material for forming a fluorescent light-emitting layer. The same is true for fluorescent hosts.
  • the substrate is used as a support for the organic EL device.
  • a plate of glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic deposition films can also be used.
  • Anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more).
  • a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more).
  • ITO Indium Tin Oxide
  • indium oxide-tin oxide containing silicon or silicon oxide indium oxide-zinc oxide
  • indium oxide containing tungsten oxide and zinc oxide Graphene etc.
  • gold Au
  • platinum Pt
  • nickel Ni
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • iron Fe
  • Co cobalt
  • Cu copper
  • palladium Pd
  • titanium Ti
  • nitrides of the above metals for example, titanium nitride
  • indium oxide-zinc oxide is a target in which 1 to 10 wt% of zinc oxide is added to indium oxide
  • indium oxide containing tungsten oxide and zinc oxide is a target in which 0.5 to 5 wt% of tungsten oxide is added to indium oxide. %, and 0.1 to 1 wt % of zinc oxide
  • it can be formed by a sputtering method.
  • it may be produced by a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method, or the like.
  • the organic layer may contain a hole-transporting zone between the anode and the light-emitting layer.
  • the hole-transporting zone is composed of a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, and the like. It is preferred that the hole-transporting zone comprises an invention compound. At least one of these layers constituting the hole-transporting layer preferably contains the invention compound, and particularly preferably the hole-transporting layer contains the invention compound.
  • the hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode. , alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Groups 1 and 2 of the Periodic Table of the Elements) can be used.
  • Elements belonging to group 1 or 2 of the periodic table which are materials with a small work function, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium Alkaline earth metals such as (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these can also be used.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such as europium (Eu) and ytterbium (Yb)
  • Yb ytterbium
  • alloys containing these can also be used.
  • the hole-injection layer is a layer containing a material with high hole-injection properties (hole-injection material), and is located between the anode and the light-emitting layer or, if present, with the hole-transport layer. formed between the anodes.
  • Hole-injecting materials other than invention compounds include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. material, tungsten oxide, manganese oxide, or the like can be used.
  • Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.
  • poly(N-vinylcarbazole) (abbreviation: PVK)
  • poly(4-vinyltriphenylamine) (abbreviation: PVTPA)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N'-[4-(4-diphenylamino) phenyl]phenyl-N'-phenylamino ⁇ phenyl)methacrylamide]
  • PTPDMA poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine]
  • polymer compounds such as Poly-TPD).
  • polymer compounds added with acids such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS) are used.
  • PDOT/PSS poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid)
  • PAni/PSS polyaniline/poly(styrenesulfonic acid)
  • acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).
  • HAT hexaazatriphenylene
  • R 221 to R 226 are each independently a cyano group, —CONH 2 , a carboxyl group, or —COOR 227 (R 227 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms).
  • R 227 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, cyclohexyl group and the like.
  • Hole-transporting layer is a layer containing a material with high hole-transporting properties (hole-transporting material), and is located between the anode and the light-emitting layer or, if present, with the hole-injecting layer. It is formed between the light emitting layers.
  • Invention compounds may be used in the hole-transporting layer alone or in combination with the following compounds.
  • the hole transport layer may have a single layer structure or a multilayer structure including two or more layers.
  • the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole-transporting zone may include a first hole-transporting layer on the anode side and a second hole-transporting layer on the cathode side.
  • the hole transport layer may have a three-layer structure including a first hole transport layer, a second hole transport layer and a third hole transport layer in order from the anode side. That is, the third hole-transporting layer may be arranged between the second hole-transporting layer and the light-emitting layer.
  • the hole-transporting layer having the single-layer structure is preferably adjacent to the light-emitting layer, and the hole-transporting layer closest to the cathode in the multilayer structure, for example, the two-layer structure It is preferable that the second hole-transporting layer of (1) and the third hole-transporting layer of the three-layer structure are adjacent to the light-emitting layer.
  • an electron A blocking layer or the like may be interposed between the hole-transporting layer and the light-emitting layer in the single-layer structure, or between the hole-transporting layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.
  • At least one of the first hole transport layer and the second hole transport layer contains the compound of the present invention.
  • the compound of the invention may be contained in either the first hole-transporting layer or the second hole-transporting layer, or may be contained in both. good.
  • at least one of the first to third hole transport layers contains the invention compound.
  • the compound of the present invention may be contained in only one of the first to third hole-transporting layers, or may be contained in only any two of the first to third hole-transporting layers. may be included or may be included in all.
  • the invention compound is preferably contained in the second hole transport layer. Specifically, the invention compound is contained only in the second hole transport layer or the invention compound is contained in the first hole transport layer. It is preferably included in the hole transport layer and the second hole transport layer. In one aspect of the present invention, the invention compound contained in one or both of the first hole-transport layer and the second hole-transport layer, and at least one or more of the first to third hole-transport layers
  • the compound of the invention contained in is preferably a light hydrogen form from the viewpoint of production cost.
  • the aforementioned light hydrogen compound means an invention compound in which all hydrogen atoms in the invention compound are hydrogen atoms.
  • one or both of the first hole transport layer and the second hole transport layer, and at least one or more of the first to third hole transport layers are substantially hydrogen-containing It includes an organic EL device containing an invention compound consisting only of a body.
  • invention compound consisting essentially of a light hydrogen body means that the content of the light hydrogen body in the total amount of the invention compounds is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each including 100%).
  • aromatic amine compounds examples include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) and N,N'-bis(3-methylphenyl)-N , N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4-phenyl-4′-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4′,4′′-tris(N,N -diphenylamino)triphenylamine
  • carbazole derivatives examples include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).
  • anthracene derivatives examples include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and , 9,10-diphenylanthracene (abbreviation: DAnth).
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • a compound other than the above may be used as long as the compound has higher hole-transporting property than electron-transporting property.
  • the first hole transport layer preferably contains a compound represented by the following formula (11) or (12).
  • L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted is a divalent heterocyclic group having 5 to 50 ring-forming atoms, k is 1, 2, 3 or 4; when k is 1, L E2 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms; When k is 2, 3 or 4, the plurality of L E2 are the same or different from each other, When k is 2, 3 or 4, a
  • R 901 to R 907 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
  • the plurality of R 901 are the same or different from each other
  • the multiple R 902 are the same or different from each other
  • the multiple R 903 are the same or different from each other
  • the multiple R 904 are the same or different from each other
  • the multiple R 905 the multiple R 905 are the same or different from each other
  • the multiple R 905 are the same or different from each other,
  • R 906 When there is a plurality of R 901 , the plurality of R 901 are the same or different from
  • the first hole transport layer may contain one compound represented by formulas (11) and (12), or the compounds represented by formulas (11) and (12) may contain a plurality of types.
  • A1, B1, C1, A2, B2, C2, and D2 are preferably each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, and substituted or unsubstituted selected from carbazolyl groups; More preferably, at least one of A1, B1 and C1 in formula (11) and at least one of A2, B2, C2 and D2 in formula (12) are substituted or unsubstituted biphenyl substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstitute
  • the fluorenyl group that A1, B1, C1, A2, B2, C2, and D2 can take may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group, a 9,9- It may be a diphenylfluorenyl group. Further, the substituents at the 9-position may form a ring together, for example, the substituents at the 9-position may form a fluorene skeleton or a xanthene skeleton.
  • L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms.
  • the light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used.
  • a fluorescent light-emitting material or a phosphorescent light-emitting material can be used as the dopant material.
  • a fluorescent light-emitting material is a compound that emits light from a singlet excited state
  • a phosphorescent light-emitting material is a compound that emits light from a triplet excited state.
  • the light-emitting layer is a single layer.
  • the light emitting layer includes a first light emitting layer and a second light emitting layer.
  • a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, or the like can be used as a blue fluorescent light-emitting material that can be used in the light-emitting layer.
  • N,N′-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4-(9H -carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H -carbazol-3-yl)triphenylamine (abbreviation: PCBAPA) and the like.
  • An aromatic amine derivative or the like can be used as a greenish fluorescent light-emitting material that can be used in the light-emitting layer.
  • N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA)
  • N-[9,10-bis(1,1 '-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine abbreviation: 2PCABPhA
  • a tetracene derivative, a diamine derivative, or the like can be used as a red fluorescent light-emitting material that can be used in the light-emitting layer.
  • N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine abbreviation: p-mPhTD
  • 7,14-diphenyl-N,N,N', and N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine abbreviation: p-mPhAFD.
  • the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).
  • Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer.
  • An iridium complex or the like is used as a greenish phosphorescent material that can be used in the light-emitting layer.
  • Tris (2-phenylpyridinato-N, C2') iridium (III) (abbreviation: Ir (ppy) 3), bis (2-phenylpyridinato-N, C2') iridium (III) acetylacetonate ( Abbreviations: Ir (ppy) 2 (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) 2 (acac)), bis (benzo[ h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)) and the like.
  • Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the light-emitting layer.
  • bis[2-(2′-benzo[4,5- ⁇ ]thienyl)pyridinato-N,C3′]iridium(III) acetylacetonate abbreviation: Ir(btp)2(acac)
  • Bis(1-phenylisoquinolinato-N,C2′)iridium(III) acetylacetonate abbreviation: Ir(piq)2(acac)
  • (acetylacetonato)bis[2,3-bis(4-fluoro Phenyl)quinoxalinato]iridium (III) abbreviation: Ir(Fdpq)2(acac)
  • tris (acetylacetonate) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) 3 (Phen)
  • tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) (abbreviation: Eu (DBM) 3 (Phen)
  • tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: Eu ( Rare-earth metal complexes such as TTA)3(Phen)) can be used as phosphorescent light-emitting materials because they emit light from rare-earth metal ions (electronic transitions between different multiplicities).
  • the light-emitting layer may have a structure in which the above-described dopant material is dispersed in another material (host material). It is preferable to use a material whose lowest unoccupied molecular orbital level (LUMO level) is higher than that of the dopant material and whose highest occupied molecular orbital level (HOMO level) is lower.
  • LUMO level lowest unoccupied molecular orbital level
  • HOMO level highest occupied molecular orbital level
  • host materials include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; (3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.
  • tris(8-quinolinolato)aluminum (III) (abbreviation: Alq)
  • tris(4-methyl-8-quinolinolato)aluminum (III) (abbreviation: Almq3)
  • bis(10-hydroxybenzo[h]quinolinato)beryllium (II) (abbreviation: BeBq2)
  • bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) abbreviation: BAlq
  • bis(8-quinolinolato)zinc (II) (abbreviation: Znq)
  • bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ)
  • other metal complexes 2-(4-biphenylyl)-5-(
  • anthracene compound As a host material, it is preferable to use the following anthracene compound as a host material.
  • the light-emitting layer when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer includes the second light-emitting layer. It is different from the constituent ingredients.
  • the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer
  • the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer. Different aspects are included.
  • the light-emitting layer may contain a light-emitting compound that emits fluorescent light with a main peak wavelength of 500 nm or less.
  • a method for measuring the main peak wavelength of a compound is as follows. A 5 ⁇ mol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300K). The emission spectrum can be measured with a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the main peak wavelength. In this specification, the main peak wavelength may be referred to as fluorescence emission main peak wavelength (FL-peak).
  • the luminescent compound that emits fluorescence with a main peak wavelength of 500 nm or less may be the dopant material or the host material.
  • the light-emitting layer is a single layer, only one of the dopant material and the host material may be a light-emitting compound that emits fluorescence with a main peak wavelength of 500 nm or less, or both materials have a main peak wavelength of A light-emitting compound that emits fluorescence at 500 nm or less may also be used. Further, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, only one of the first light-emitting layer and the second light-emitting layer emits fluorescence having a main peak wavelength of 500 nm or less.
  • both light-emitting layers may contain a light-emitting compound that emits fluorescent light having a main peak wavelength of 500 nm or less.
  • the first light-emitting layer contains a light-emitting compound that emits fluorescence with a main peak wavelength of 500 nm or less
  • only one of the dopant material and the host material contained in the first light-emitting layer has a main peak wavelength of It may be a luminescent compound that emits fluorescence at 500 nm or less, or both materials may be luminescent compounds that emit fluorescence with a main peak wavelength of 500 nm or less.
  • the second light-emitting layer contains a light-emitting compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less
  • only one of the dopant material and the host material contained in the second light-emitting layer has a main peak wavelength of It may be a luminescent compound that emits fluorescence at 500 nm or less, or both materials may be luminescent compounds that emit fluorescence with a main peak wavelength of 500 nm or less.
  • the electron-transporting layer is a layer containing a material with high electron-transporting properties (electron-transporting material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron-injecting layer and the light-emitting layer.
  • the electron transport layer may have a single layer structure or a multilayer structure including two or more layers.
  • the electron transport layer may have a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side).
  • the single-layer electron-transporting layer is preferably adjacent to the light-emitting layer, and the electron-transporting layer closest to the anode in the multilayer structure, for example, the second electron-transporting layer of the two-layer structure. 1
  • the electron-transporting layer is preferably adjacent to the light-emitting layer.
  • a hole-blocking layer as described below is provided between the electron-transporting layer and the light-emitting layer in the single-layer structure, or between the electron-transporting layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. A layer or the like may be interposed.
  • metal complexes such as aluminum complexes, beryllium complexes and zinc complexes
  • heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives
  • Polymer compounds can be used.
  • metal complexes examples include tris(8-quinolinolato)aluminum (III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato ) beryllium (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) (abbreviation: Znq ), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).
  • Alq tris(8-quinolinolato)aluminum
  • heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5 -(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5- (4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2 ,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4′-bis(5-methylbenzoxa
  • polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9, 9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).
  • the above material is a material having an electron mobility of 10 ⁇ 6 cm 2 /Vs or more. Materials other than those described above may be used for the electron transport layer as long as the material has higher electron transport properties than hole transport properties.
  • the electron injection layer is a layer containing a material with high electron injection properties.
  • the electron injection layer contains alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), europium (Eu) and ytterbium (Yb).
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr)
  • Eu europium
  • Yb ytterbium
  • Rare earth metals such as and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, and rare earth metal oxides.
  • a material having an electron-transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq may be used.
  • electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer.
  • Such a composite material has excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor.
  • the organic compound is preferably a material that is excellent in transporting the received electrons.
  • the material (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer described above is used. be able to.
  • the electron donor any material can be used as long as it exhibits an electron donating property with respect to the organic compound.
  • alkali metals, alkaline earth metals and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide and barium oxide.
  • Lewis bases such as magnesium oxide can also be used.
  • An organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.
  • Cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less).
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca ), alkaline earth metals such as strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
  • a vacuum deposition method and a sputtering method can be used.
  • a coating method, an inkjet method, or the like can be used.
  • a cathode is formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the magnitude of the work function. can do. These conductive materials can be deposited using a sputtering method, an inkjet method, a spin coating method, or the like.
  • an insulating layer made of an insulating thin film layer may be inserted between the pair of electrodes.
  • materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. , germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like. A mixture or laminate of these materials may also be used.
  • the space layer is, for example, when a fluorescent-emitting layer and a phosphorescent-emitting layer are laminated, for the purpose of preventing excitons generated in the phosphorescent-emitting layer from diffusing into the fluorescent-emitting layer or adjusting the carrier balance. It is a layer provided between the fluorescent-emitting layer and the phosphorescent-emitting layer. A space layer can also be provided between a plurality of phosphorescent-emitting layers. Since the space layer is provided between the light-emitting layers, it is preferably made of a material having both electron-transporting properties and hole-transporting properties. Moreover, the triplet energy is preferably 2.6 eV or more in order to prevent diffusion of the triplet energy in the adjacent phosphorescent-emitting layer. Materials used for the space layer include those similar to those used for the above-described hole transport layer.
  • Blocking layers such as electron blocking layers, hole blocking layers, exciton blocking layers, etc. may be provided adjacent to the light-emitting layer.
  • the electron-blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole-transporting layer
  • the hole-blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron-transporting layer.
  • the exciton-blocking layer has the function of preventing the excitons generated in the light-emitting layer from diffusing to surrounding layers and confining the excitons within the light-emitting layer.
  • Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like.
  • a vapor deposition method such as a vacuum vapor deposition method or a molecular beam vapor deposition method (MBE method), or a dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like using a solution of a compound forming a layer.
  • MBE method molecular beam vapor deposition method
  • the film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur. 10 nm to 0.2 ⁇ m is more preferred.
  • the total thickness of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less. In this case, it is preferably 40 nm or more and 130 nm or less.
  • the thickness of the second hole transport layer is 20 nm or more. It is preferably 25 nm or more, more preferably 35 nm or more, and preferably 100 nm or less.
  • the hole-transporting layer adjacent to the light-emitting layer has a thickness of 20 nm or more.
  • the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer satisfy the relationship 0.3 ⁇ D2/D1 ⁇ 4.0. . It preferably satisfies the relationship 0.5 ⁇ D2/D1 ⁇ 3.5, and more preferably satisfies the relationship 0.75 ⁇ D2/D1 ⁇ 3.0.
  • Embodiments of the organic EL element of the present invention include, for example, The organic EL device having the two-layer structure of the hole transport layer, - a first embodiment, wherein the second hole-transporting layer comprises a compound of the invention and the first hole-transporting layer does not comprise a compound of the invention; - a second embodiment in which both the first hole-transporting layer and the second hole-transporting layer comprise a compound of the invention; - a third embodiment, wherein the first hole-transporting layer comprises a compound of the invention and the second hole-transporting layer does not comprise a compound of the invention; An organic EL device having a hole transport layer having a three-layer structure, - a fourth embodiment, wherein the first hole-transporting layer comprises a compound of the invention and the second and third hole-transporting layers do not comprise a compound of the invention; - a fifth embodiment, wherein the second hole-transporting layer comprises a compound of the invention and the first and third hole-transporting layers do not comprise a compound of the invention
  • the organic EL element can be used for display parts such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic equipment such as light-emitting devices for lighting and vehicle lamps.
  • compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 75 nm.
  • Compound 1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.
  • compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 20 nm.
  • the mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1.
  • the compound ET-1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm.
  • compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 25 nm.
  • the mass ratio of compound ET-2 and Liq (ET-2:Liq) was 50:50.
  • Yb was deposited on the second electron transport layer to form an electron injecting electrode with a thickness of 1 nm.
  • metal Al was vapor-deposited on this electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.
  • the layer structure of the organic EL device of Example 1 thus obtained is shown below.
  • EQE External Quantum Efficiency
  • Example 2 and Comparative Example 1 Each organic EL device was produced in the same manner as in Example 1 except that Compound 2 (Example 2) and Comparative Compound 1 (Comparative Example 1) were used instead of Compound 1, and the external quantum efficiency was measured. Table 1 shows the results.
  • compound HT-2 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm.
  • compound 3 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.
  • compound BH-2 (host material) and compound BD-2 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 25 nm.
  • the mass ratio of compound BH-2 to compound BD-2 (BH-2:BD-2) was 96:4.
  • the compound ET-3 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer with a thickness of 10 nm.
  • compound ET-4 was deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm.
  • LiF was vapor-deposited on the second electron-transporting layer to form an electron-injecting electrode with a film thickness of 1 nm.
  • metal Al was vapor-deposited on this electron-injecting electrode to form a metal cathode with a film thickness of 50 nm.
  • the layer structure of the organic EL element of Example 3 thus obtained is shown below.
  • Examples 4-9 and Comparative Examples 2 and 3 Each organic EL element was produced in the same manner as in Example 3 except that Compounds 4 to 9 (Examples 4 to 9) and Comparative Compounds 2 and 3 (Comparative Examples 2 and 3) were used instead of Compound 3. , measured the external quantum efficiency. Table 2 shows the results.
  • the monoamines (compounds of Examples 3 to 9) that satisfy the requirements of the present invention are compared to the monoamines (comparative compounds of Comparative Examples 2 and 3) that do not satisfy the requirements of the present invention. to provide an organic EL device with improved external quantum efficiency.
  • the obtained residue was purified by silica gel column chromatography and recrystallization to obtain 2.35 g of white solid. Yield was 50%.
  • a white solid was obtained in the same manner as in Synthesis Example 1, except that Intermediate B was used instead of Intermediate A.
  • a white solid was obtained in the same manner as in Synthesis Example 1 except that Intermediate C was used in place of 1-(4'-chloro[1,1'-biphenyl]-4-yl)naphthalene.
  • a white solid was obtained in the same manner as in Synthesis Example 1 except that N-[3-(1-naphthalenyl)phenyl][1,1′-biphenyl]-2-amine was used instead of Intermediate A.
  • a white solid was obtained in the same manner as in Synthesis Example 1 except that N-[3-(2-naphthalenyl)phenyl][1,1′-biphenyl]-4-amine was used instead of Intermediate A.
  • a white solid was obtained in the same manner as in Synthesis Example 1 except that N-[3-(1-naphthalenyl)phenyl][1,1′-biphenyl]-4-amine was used instead of Intermediate A.

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Abstract

A compound represented by formula (1) (In formula (1), N*, R1A-R5A, R1B-R5B, R1C-R4C, R1D-R5D, R1U-R8U, R1V-R7V, Ar, m, *a, *b, *d, *u, *v, benzene ring A-benzene ring D, naphthalene ring U, and naphthalene ring V are as defined in formula (1).), an organic electroluminescent element including said compound, and an electronic device including such an organic electroluminescent element.

Description

化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器Compounds, materials for organic electroluminescence devices, organic electroluminescence devices, and electronic devices
　本発明は、化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び該有機エレクトロルミネッセンス素子を含む電子機器に関する。 The present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device including the organic electroluminescence device.
　一般に有機エレクトロルミネッセンス素子（以下、“有機ＥＬ素子”と記載することもある）は陽極、陰極、及び陽極と陰極に挟まれた有機層から構成されている。両電極間に電圧が印加されると、陰極側から電子、陽極側から正孔が発光領域に注入され、注入された電子と正孔は発光領域において再結合して励起状態を生成し、励起状態が基底状態に戻る際に光を放出する。従って、電子又は正孔を発光領域に効率よく輸送し、電子と正孔との再結合を容易にする材料の開発は高性能有機ＥＬ素子を得る上で重要である。 Generally, an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes from the anode side into the light-emitting region. It emits light when the state returns to the ground state. Therefore, development of a material that efficiently transports electrons or holes to the light-emitting region and facilitates recombination of electrons and holes is important for obtaining high-performance organic EL devices.
　特許文献１及び２には、有機エレクトロルミネッセンス素子用材料として使用する化合物が開示されている。 Patent Documents 1 and 2 disclose compounds used as materials for organic electroluminescence elements.
国際公開第２０２１／０７０９６５号WO2021/070965 国際公開第２０２１／０２５３７２号WO2021/025372
　従来、多くの有機ＥＬ素子用の化合物が報告されているが、有機ＥＬ素子の性能を更に向上させる化合物が依然として求められている。 Although many compounds for organic EL devices have been reported in the past, there is still a demand for compounds that further improve the performance of organic EL devices.
　本発明は、前記の課題を解決するためになされたもので、有機ＥＬ素子の性能をより改善する化合物、素子性能がより改善された有機ＥＬ素子、そのような有機ＥＬ素子を含む電子機器を提供することを目的とする。 The present invention has been made to solve the above problems, and provides a compound that further improves the performance of an organic EL device, an organic EL device with improved device performance, and an electronic device containing such an organic EL device. intended to provide
　本発明者らは、特許文献１及び２に記載の化合物を含む有機ＥＬ素子の性能について鋭意研究を重ねた結果、下記式（１）で表される化合物を含む有機ＥＬ素子は、性能がより改善されることを見出した。 The present inventors have extensively studied the performance of organic EL devices containing the compounds described in Patent Documents 1 and 2. As a result, organic EL devices containing the compound represented by the following formula (1) have better performance. found to be improved.
　一態様において、本発明は下記式（１）で表される化合物を提供する。
Figure JPOXMLDOC01-appb-C000011
（式（１）中、
　Ｎ＊は中心窒素原子であり、
　Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、及びＲ１Ｄ～Ｒ５Ｄは、それぞれ独立して、水素原子、無置換の炭素数１～６のアルキル基、又は無置換の環形成炭素数６～１２のアリール基である。
　ただし、
　Ｒ１Ａ～Ｒ５Ａから選ばれる１つは＊ａに結合する単結合であり、
　Ｒ１Ｂ～Ｒ５Ｂから選ばれる１つは＊ｂに結合する単結合であり、
　Ｒ１Ｄ～Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、
　前記単結合ではないＲ１Ａ～Ｒ５Ａから選ばれる隣接する２つ、前記単結合ではないＲ１Ｂ～Ｒ５Ｂから選ばれる隣接する２つ、及び前記単結合ではないＲ１Ｄ～Ｒ５Ｄから選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成せず、
　ベンゼン環Ａとベンゼン環Ｂは架橋しない。
 
　ｍは０又は１である。
　ただし、ｍが０のとき、＊ｄが中心窒素原子Ｎ＊に結合する。
 
　Ｒ１Ｃ～Ｒ４Ｃ、Ｒ１Ｕ～Ｒ８Ｕ、及びＲ１Ｖ～Ｒ８Ｖは、水素原子である。
　ただし、
　Ｒ１Ｕ～Ｒ８Ｕから選ばれる１つは＊ｕに結合する単結合であり、
　Ｒ１Ｖ～Ｒ８Ｖから選ばれる１つは＊ｖに結合する単結合であり、
　ベンゼン環Ｂとナフタレン環Ｕ、ベンゼン環Ｃとナフタレン環Ｖは、架橋しない。
 
　Ａｒは、下記式（１－ａ）～（１－ｅ）のいずれかで表される。
Figure JPOXMLDOC01-appb-C000012
（式（１－ａ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ１～Ｒ５は、それぞれ独立して、水素原子、無置換の炭素数１～６のアルキル基、又は無置換のフェニル基である。
　ただし、
　前記Ｒ１～Ｒ５から選ばれる１つは＊ｅに結合する単結合であり、前記Ｒ１～Ｒ５から選ばれる他の１つは＊ｆに結合する単結合であり、
　前記単結合ではないＲ１～Ｒ５から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成せず、
　ｍが１でｎが１でｌが０のとき下記（ｉ）又は（ｉｉ）を満たし、
　ｍが１でｎが０でｌが１のとき、下記（ｉｉｉ）又は（ｉｖ）を満たす。
（ｉ）Ｒ３Ｄは＊ｄに結合する単結合であり、Ｒ１、Ｒ２、Ｒ４、及びＲ５から選ばれる１つは＊ｅに結合する単結合である。
（ｉｉ）Ｒ１Ｄ、Ｒ２Ｄ、Ｒ４Ｄ、Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、Ｒ１～Ｒ５から選ばれる１つは＊ｅに結合する単結合である。
（ｉｉｉ）Ｒ３Ｄは＊ｄに結合する単結合であり、Ｒ１、Ｒ２、Ｒ４、及びＲ５から選ばれる１つは＊ｆに結合する単結合である。
（ｉｖ）Ｒ１Ｄ、Ｒ２Ｄ、Ｒ４Ｄ、Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、Ｒ１～Ｒ５から選ばれる１つは＊ｆに結合する単結合である。
 
　Ａｒ１１及びＡｒ１２は、下記式（ｉ）で表される基である。
Figure JPOXMLDOC01-appb-C000013
（式（ｉ）中、
　＊＊＊は、結合位置を表す。
　Ｒ１１～Ｒ１５は、それぞれ独立して、水素原子又は無置換の炭素数１～６のアルキル基である。
　ただし、
　Ｒ１１～Ｒ１５から選ばれる隣接する２つ、及びＲ２１～Ｒ２５から選ばれる隣接する２つは、互いに結合して、置換もしくは無置換のベンゼン環を形成してもよい。）
 
　ｎは０～２の整数であり、ｎが０のとき、（Ａｒ１１）０は水素原子を表わし、
　ｌは０～２の整数であり、ｌが０のとき、（Ａｒ１２）０は水素原子を表わす。）
 
Figure JPOXMLDOC01-appb-C000014
（式（１－ｂ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ２１～Ｒ２８は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
　ただし、
　前記Ｒ２１～Ｒ２８から選ばれる１つは＊ｇに結合する単結合であり、前記Ｒ２１～Ｒ２８から選ばれる他の１つは＊ｈに結合する単結合であり、前記Ｒ２１～Ｒ２８から選ばれるさらに他の１つは＊ｉに結合する単結合であり、
　前記単結合ではないＲ２１～Ｒ２８から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。
 
　Ａｒ１３及びＡｒ１４は、下記式（ｉｉ）で表される基である。
Figure JPOXMLDOC01-appb-C000015
（式（ｉｉ）中、
　＊＊＊は、結合位置を表す。
　Ｒ３１～Ｒ３５は、水素原子である。）
 
　ｏは０、又は１であり、ｏが０のとき（Ａｒ１３）０は水素原子を表わし、
　ｐは０、又は１であり、ｐが０のとき（Ａｒ１４）０は水素原子を表わす。）
 
Figure JPOXMLDOC01-appb-C000016
（式（１－ｃ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ４１～Ｒ５２は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
　ただし、
　前記Ｒ４１～Ｒ５２から選ばれる１つは＊ｊに結合する単結合であり、前記Ｒ４１～Ｒ５２から選ばれる他の１つは＊ｋに結合する単結合であり、前記Ｒ４１～Ｒ５２から選ばれるさらに他の１つは＊ｌに結合する単結合であり、
　前記単結合ではないＲ４１～Ｒ５２から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。
 
　Ａｒ１５及びＡｒ１６は、前記式（ｉｉ）で表される基である。
　ｑは０、又は１であり、ｑが０のとき（Ａｒ１５）０は水素原子を表わし、
　ｒは０、又は１であり、ｒが０のとき（Ａｒ１６）０は水素原子を表わす。）
 
Figure JPOXMLDOC01-appb-C000017
（式（１－ｄ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ６１～Ｒ７０は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
　ただし、
　前記Ｒ６１～Ｒ７０から選ばれる１つは＊ｍに結合する単結合であり、前記Ｒ６１～Ｒ７０から選ばれる他の１つは＊ｎに結合する単結合であり、前記Ｒ６１～Ｒ７０から選ばれるさらに他の１つは＊ｏに結合する単結合であり、
　前記単結合ではないＲ６１～Ｒ７０から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。
 
　Ａｒ１7及びＡｒ１８は、前記式（ｉｉ）で表される基である。
　ｓは０、又は１であり、ｓが０のとき（Ａｒ１７）０は水素原子を表わし、
　ｔは０、又は１であり、ｔが０のとき（Ａｒ１８）０は水素原子を表わす。
 
Figure JPOXMLDOC01-appb-C000018
（式（１－ｅ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ８１～Ｒ８８は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
　ＲＡ及びＲＢは、それぞれ独立して、メチル基、置換もしくは無置換のフェニル基である。
　ただし、
　＊ｐは、前記Ｒ８１～Ｒ８８、ＲＡ及びＲＢから選ばれる１つに結合し、
　ＲＡ又はＲＢが＊ｌに結合する場合、＊ｌに結合するＲＡ又はＲＢはメチレン基又は置換もしくは無置換のフェニレン基であり、
　前記Ｒ８１～Ｒ８８から選ばれる１つが＊ｌに結合する場合、＊ｌに結合する前記Ｒ８１～Ｒ８８から選ばれる１つは単結合であり、
　前記単結合ではないＲ８１～Ｒ８８から選ばれる隣接する２つは、互いに結合して、置換もしくは無置換のベンゼン環を形成してもよく、
　＊ｌに結合しないＲＡとＲＢが結合して、スピロ環を形成してもよい。）） In one aspect, the present invention provides a compound represented by formula (1) below.
Figure JPOXMLDOC01-appb-C000011
(In formula (1),
N * is the central nitrogen atom,
R 1A to R 5A , R 1B to R 5B , and R 1D to R 5D are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted 6 to 6 ring carbon atoms. 12 aryl groups.
however,
one selected from R 1A to R 5A is a single bond that binds to *a;
one selected from R 1B to R 5B is a single bond that bonds to *b;
one selected from R 1D to R 5D is a single bond that bonds to *d;
Adjacent two selected from R 1A to R 5A which are not single bonds, adjacent two selected from R 1B to R 5B which are not single bonds, and R 1D to R 5D which are not single bonds adjacent two are not bonded to each other and thus do not form a ring structure;
Benzene ring A and benzene ring B are not crosslinked.

m is 0 or 1;
However, when m is 0, *d is bound to the central nitrogen atom N * .

R 1C to R 4C , R 1U to R 8U and R 1V to R 8V are hydrogen atoms.
however,
one selected from R 1U to R 8U is a single bond that binds to *u;
one selected from R 1V to R 8V is a single bond that binds to *v;
Benzene ring B and naphthalene ring U and benzene ring C and naphthalene ring V are not crosslinked.

Ar is represented by any one of the following formulas (1-a) to (1-e).
Figure JPOXMLDOC01-appb-C000012
(In formula (1-a),
** represents the binding position to the above *d.
R 1 to R 5 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group.
however,
one selected from R 1 to R 5 is a single bond that bonds to *e, and the other one selected from R 1 to R 5 is a single bond that bonds to *f;
adjacent two selected from R 1 to R 5 which are not single bonds are not bonded to each other and therefore do not form a ring structure;
When m is 1, n is 1, and l is 0, the following (i) or (ii) is satisfied,
When m is 1, n is 0, and l is 1, the following (iii) or (iv) is satisfied.
(i) R 3D is a single bond bonded to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond bonded to *e;
(ii) one selected from R 1D , R 2D , R 4D and R 5D is a single bond that bonds to *d, and one selected from R 1 to R 5 is a single bond that bonds to *e .
(iii) R 3D is a single bond that bonds to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond that bonds to *f.
(iv) one selected from R 1D , R 2D , R 4D and R 5D is a single bond that binds to *d, and one selected from R 1 to R 5 is a single bond that binds to *f .

Ar 11 and Ar 12 are groups represented by the following formula (i).
Figure JPOXMLDOC01-appb-C000013
(In formula (i),
*** represents the binding position.
R 11 to R 15 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms.
however,
Two adjacent groups selected from R 11 to R 15 and two adjacent groups selected from R 21 to R 25 may combine with each other to form a substituted or unsubstituted benzene ring. )
 
n is an integer of 0 to 2, and when n is 0, (Ar 11 ) 0 represents a hydrogen atom;
l is an integer of 0 to 2, and when l is 0, (Ar 12 ) 0 represents a hydrogen atom. )

Figure JPOXMLDOC01-appb-C000014
(In formula (1-b),
** represents the binding position to the above *d.
R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
however,
One selected from R 21 to R 28 is a single bond that bonds to *g, the other one selected from R 21 to R 28 is a single bond that bonds to *h, and R 21 to Still another one selected from R 28 is a single bond attached to *i,
Adjacent two groups selected from R 21 to R 28 which are not single bonds are not bonded to each other and therefore do not form a ring structure.

Ar 13 and Ar 14 are groups represented by the following formula (ii).
Figure JPOXMLDOC01-appb-C000015
(In formula (ii),
*** represents the binding position.
R 31 to R 35 are hydrogen atoms. )

o is 0 or 1, and when o is 0 (Ar 13 ) 0 represents a hydrogen atom;
p is 0 or 1, and (Ar 14 ) 0 represents a hydrogen atom when p is 0; )

Figure JPOXMLDOC01-appb-C000016
(In formula (1-c),
** represents the binding position to the above *d.
R 41 to R 52 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
however,
One selected from R 41 to R 52 is a single bond that bonds to *j, the other one selected from R 41 to R 52 is a single bond that bonds to *k, and R 41 to Further one selected from R 52 is a single bond attached to *l,
Adjacent two selected from R 41 to R 52 which are not single bonds are not bonded to each other and thus do not form a ring structure.

Ar 15 and Ar 16 are groups represented by the above formula (ii).
q is 0 or 1, and when q is 0 (Ar 15 ) 0 represents a hydrogen atom;
r is 0 or 1, and (Ar 16 ) 0 represents a hydrogen atom when r is 0; )

Figure JPOXMLDOC01-appb-C000017
(In formula (1-d),
** represents the binding position to the above *d.
R 61 to R 70 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
however,
One selected from R 61 to R 70 is a single bond that bonds to *m, the other one selected from R 61 to R 70 is a single bond that bonds to *n, and R 61 to Still another one selected from R 70 is a single bond attached to *o,
Adjacent two groups selected from R 61 to R 70 which are not single bonds are not bonded to each other and therefore do not form a ring structure.

Ar 17 and Ar 18 are groups represented by the above formula (ii).
s is 0 or 1, and when s is 0 (Ar 17 ) 0 represents a hydrogen atom,
t is 0 or 1, and (Ar 18 ) 0 represents a hydrogen atom when t is 0;

Figure JPOXMLDOC01-appb-C000018
(In formula (1-e),
** represents the binding position to the above *d.
R 81 to R 88 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
R A and R B are each independently a methyl group or a substituted or unsubstituted phenyl group.
however,
* p is bound to one selected from R 81 to R 88 , R A and R B ;
when R A or R B is attached to *l, R A or R B attached to *l is a methylene group or a substituted or unsubstituted phenylene group;
when one selected from R 81 to R 88 is bonded to *l, one selected from R 81 to R 88 bonded to *l is a single bond;
Adjacent two selected from R 81 to R 88 which are not single bonds may be bonded to each other to form a substituted or unsubstituted benzene ring,
* R A and R B that are not bonded to l may combine to form a spiro ring. ))
　他の態様において、本発明は前記式（１）で表される化合物を含む有機ＥＬ素子用材料を提供する。 In another aspect, the present invention provides an organic EL device material containing the compound represented by the formula (1).
　さらに他の態様において、本発明は、陰極、陽極、及び該陰極と該陽極の間に有機層を含む、有機エレクトロルミネッセンス素子であって、該有機層が発光層を含み、該有機層の少なくとも１層が前記式（１）で表される化合物を含む有機エレクトロルミネッセンス素子を提供する。 In still another aspect, the present invention is an organic electroluminescent device comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer comprises a light-emitting layer, and at least one of the organic layers Provided is an organic electroluminescence device in which one layer contains the compound represented by the formula (1).
　さらに他の態様において、本発明は、前記有機エレクトロルミネッセンス素子を含む電子機器を提供する。 In still another aspect, the present invention provides an electronic device including the organic electroluminescence element.
　前記式（１）で表される化合物を含む有機ＥＬ素子は改善された素子性能を示す。 An organic EL device containing the compound represented by formula (1) exhibits improved device performance.
本発明の一態様に係る有機ＥＬ素子の層構成の一例を示す概略図である。1 is a schematic diagram showing an example of a layer structure of an organic EL element according to one aspect of the present invention; FIG. 本発明の一態様に係る有機ＥＬ素子の層構成の他の例を示す概略図である。FIG. 4 is a schematic diagram showing another example of the layer structure of the organic EL element according to one aspect of the present invention; 本発明の一態様に係る有機ＥＬ素子の層構成の他の例を示す概略図である。FIG. 4 is a schematic diagram showing another example of the layer structure of the organic EL element according to one aspect of the present invention;
［定義］
　本明細書において、水素原子とは、中性子数が異なる同位体、即ち、軽水素（protium）、重水素（deuterium）、及び三重水素（tritium）を包含する。 [definition]
As used herein, a hydrogen atom includes isotopes with different neutron numbers, ie, protium, deuterium, and tritium.
　本明細書において、化学構造式中、「Ｒ」等の記号や重水素原子を表す「Ｄ」が明示されていない結合可能位置には、水素原子、即ち、軽水素原子、重水素原子、又は三重水素原子が結合しているものとする。 In the present specification, in the chemical structural formula, a hydrogen atom, that is, a hydrogen atom, a deuterium atom, or Assume that the tritium atoms are bonded.
　本明細書において、環形成炭素数とは、原子が環状に結合した構造の化合物（例えば、単環化合物、縮合環化合物、架橋化合物、炭素環化合物、及び複素環化合物）の当該環自体を構成する原子のうちの炭素原子の数を表す。当該環が置換基によって置換される場合、置換基に含まれる炭素は環形成炭素数には含まない。以下で記される「環形成炭素数」については、別途記載のない限り同様とする。例えば、ベンゼン環は環形成炭素数が６であり、ナフタレン環は環形成炭素数が１０であり、ピリジン環は環形成炭素数５であり、フラン環は環形成炭素数４である。また、例えば、９，９－ジフェニルフルオレニル基の環形成炭素数は１３であり、９，９’－スピロビフルオレニル基の環形成炭素数は２５である。
　また、ベンゼン環に置換基として、例えば、アルキル基が置換している場合、当該アルキル基の炭素数は、ベンゼン環の環形成炭素数に含めない。そのため、アルキル基が置換しているベンゼン環の環形成炭素数は、６である。また、ナフタレン環に置換基として、例えば、アルキル基が置換している場合、当該アルキル基の炭素数は、ナフタレン環の環形成炭素数に含めない。そのため、アルキル基が置換しているナフタレン環の環形成炭素数は、１０である。 As used herein, the number of ring-forming carbon atoms refers to the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). represents the number of carbon atoms among the atoms that When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same applies to the "number of ring-forming carbon atoms" described below unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Further, for example, the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms, and the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
When the benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms in the alkyl group is not included in the number of ring-forming carbon atoms in the benzene ring. Therefore, the number of ring-forming carbon atoms in the benzene ring substituted with the alkyl group is 6. When the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms in the alkyl group is not included in the number of carbon atoms in the naphthalene ring. Therefore, the naphthalene ring substituted with an alkyl group has 10 ring-forming carbon atoms.
　本明細書において、環形成原子数とは、原子が環状に結合した構造（例えば、単環、縮合環、及び環集合）の化合物（例えば、単環化合物、縮合環化合物、架橋化合物、炭素環化合物、及び複素環化合物）の当該環自体を構成する原子の数を表す。環を構成しない原子（例えば、環を構成する原子の結合を終端する水素原子）や、当該環が置換基によって置換される場合の置換基に含まれる原子は環形成原子数には含まない。以下で記される「環形成原子数」については、別途記載のない限り同様とする。例えば、ピリジン環の環形成原子数は６であり、キナゾリン環の環形成原子数は１０であり、フラン環の環形成原子数は５である。例えば、ピリジン環に結合している水素原子、又は置換基を構成する原子の数は、ピリジン環形成原子数の数に含めない。そのため、水素原子、又は置換基が結合しているピリジン環の環形成原子数は、６である。また、例えば、キナゾリン環の炭素原子に結合している水素原子、又は置換基を構成する原子については、キナゾリン環の環形成原子数の数に含めない。そのため、水素原子、又は置換基が結合しているキナゾリン環の環形成原子数は１０である。 In the present specification, the number of ring-forming atoms refers to compounds (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compound, and heterocyclic compound) represents the number of atoms constituting the ring itself. Atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom that constitutes a ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below unless otherwise specified. For example, the pyridine ring has 6 ring-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming atoms. For example, hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of atoms forming the pyridine ring. Therefore, the number of ring-forming atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is 6. Further, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are 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 hydrogen atoms or substituents are bonded is 10.
　本明細書において、「置換もしくは無置換の炭素数ＸＸ～ＹＹのＺＺ基」という表現における「炭素数ＸＸ～ＹＹ」は、ＺＺ基が無置換である場合の炭素数を表し、置換されている場合の置換基の炭素数を含めない。ここで、「ＹＹ」は、「ＸＸ」よりも大きく、「ＸＸ」は、１以上の整数を意味し、「ＹＹ」は、２以上の整数を意味する。 In the present specification, the expression "substituted or unsubstituted XX to YY carbon number ZZ group" represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in the substituents. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
　本明細書において、「置換もしくは無置換の原子数ＸＸ～ＹＹのＺＺ基」という表現における「原子数ＸＸ～ＹＹ」は、ＺＺ基が無置換である場合の原子数を表し、置換されている場合の置換基の原子数を含めない。ここで、「ＹＹ」は、「ＸＸ」よりも大きく、「ＸＸ」は、１以上の整数を意味し、「ＹＹ」は、２以上の整数を意味する。 In the present specification, the term “substituted or unsubstituted ZZ group having an atomic number of XX to YY”, “the atomic number of XX to YY” represents the number of atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of atoms of the substituents in the case. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
　本明細書において、無置換のＺＺ基とは「置換もしくは無置換のＺＺ基」が「無置換のＺＺ基」である場合を表し、置換のＺＺ基とは「置換もしくは無置換のＺＺ基」が「置換のＺＺ基」である場合を表す。
　本明細書において、「置換もしくは無置換のＺＺ基」という場合における「無置換」とは、ＺＺ基における水素原子が置換基と置き換わっていないことを意味する。「無置換のＺＺ基」における水素原子は、軽水素原子、重水素原子、又は三重水素原子である。
　また、本明細書において、「置換もしくは無置換のＺＺ基」という場合における「置換」とは、ＺＺ基における１つ以上の水素原子が、置換基と置き換わっていることを意味する。「ＡＡ基で置換されたＢＢ基」という場合における「置換」も同様に、ＢＢ基における１つ以上の水素原子が、ＡＡ基と置き換わっていることを意味する。 In the present specification, an unsubstituted ZZ group represents a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group is a "substituted or unsubstituted ZZ group". is a "substituted ZZ group".
As used herein, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. A hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
Further, in the present specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. "Substituted" in the case of "a BB group substituted with an AA group" similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.
「本明細書に記載の置換基」
　以下、本明細書に記載の置換基について説明する。 "substituents described herein"
The substituents described in this specification are described below.
　本明細書に記載の「無置換のアリール基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
　本明細書に記載の「無置換の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
　本明細書に記載の「無置換のアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。
　本明細書に記載の「無置換のアルケニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
　本明細書に記載の「無置換のアルキニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
　本明細書に記載の「無置換のシクロアルキル基」の環形成炭素数は、本明細書に別途記載のない限り、３～５０であり、好ましくは３～２０、より好ましくは３～６である。
　本明細書に記載の「無置換のアリーレン基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
　本明細書に記載の「無置換の２価の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
　本明細書に記載の「無置換のアルキレン基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。 The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
The number of ring-forming atoms of the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified. be.
The number of carbon atoms in the "unsubstituted alkyl group" described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified. be.
The number of ring-forming carbon atoms of the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
The number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5, unless otherwise specified herein. ~18.
The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
・「置換もしくは無置換のアリール基」
　本明細書に記載の「置換もしくは無置換のアリール基」の具体例（具体例群Ｇ１）としては、以下の無置換のアリール基（具体例群Ｇ１Ａ）及び置換のアリール基（具体例群Ｇ１Ｂ）等が挙げられる。（ここで、無置換のアリール基とは「置換もしくは無置換のアリール基」が「無置換のアリール基」である場合を指し、置換のアリール基とは「置換もしくは無置換のアリール基」が「置換のアリール基」である場合を指す。）本明細書において、単に「アリール基」という場合は、「無置換のアリール基」と「置換のアリール基」の両方を含む。
　「置換のアリール基」は、「無置換のアリール基」の１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアリール基」としては、例えば、下記具体例群Ｇ１Ａの「無置換のアリール基」の１つ以上の水素原子が置換基と置き換わった基、及び下記具体例群Ｇ１Ｂの置換のアリール基の例等が挙げられる。尚、ここに列挙した「無置換のアリール基」の例、及び「置換のアリール基」の例は、一例に過ぎず、本明細書に記載の「置換のアリール基」には、下記具体例群Ｇ１Ｂの「置換のアリール基」におけるアリール基自体の炭素原子に結合する水素原子がさらに置換基と置き換わった基、及び下記具体例群Ｇ１Ｂの「置換のアリール基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・"Substituted or unsubstituted aryl group"
Specific examples of the "substituted or unsubstituted aryl group" described in the specification (specific example group G1) include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B ) and the like. (Here, unsubstituted aryl group refers to the case where "substituted or unsubstituted aryl group" is "unsubstituted aryl group", and substituted aryl group is "substituted or unsubstituted aryl group" It refers to a "substituted aryl group".) In the present specification, the term "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group".
A "substituted aryl group" means a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" of Specific Example Group G1A below is replaced with a substituent, and a substituted aryl group of Specific Example Group G1B below. Examples include: The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are only examples, and the "substituted aryl group" described herein includes the following specific examples A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of Group G1B is further replaced with a substituent, and the hydrogen atom of the substituent in the "substituted aryl group" of Specific Example Group G1B below Furthermore, groups substituted with substituents are also included.
・無置換のアリール基（具体例群Ｇ１Ａ）：
フェニル基、
ｐ－ビフェニル基、
ｍ－ビフェニル基、
ｏ－ビフェニル基、
ｐ－ターフェニル－４－イル基、
ｐ－ターフェニル－３－イル基、
ｐ－ターフェニル－２－イル基、
ｍ－ターフェニル－４－イル基、
ｍ－ターフェニル－３－イル基、
ｍ－ターフェニル－２－イル基、
ｏ－ターフェニル－４－イル基、
ｏ－ターフェニル－３－イル基、
ｏ－ターフェニル－２－イル基、
１－ナフチル基、
２－ナフチル基、
アントリル基、
ベンゾアントリル基、
フェナントリル基、
ベンゾフェナントリル基、
フェナレニル基、
ピレニル基、
クリセニル基、
ベンゾクリセニル基、
トリフェニレニル基、
ベンゾトリフェニレニル基、
テトラセニル基、
ペンタセニル基、
フルオレニル基、
９，９’－スピロビフルオレニル基、
ベンゾフルオレニル基、
ジベンゾフルオレニル基、
フルオランテニル基、
ベンゾフルオランテニル基、
ペリレニル基、及び
下記一般式（ＴＥＭＰ－１）～（ＴＥＭＰ－１５）で表される環構造から１つの水素原子を除くことにより誘導される１価のアリール基。 - Unsubstituted aryl group (specific example group G1A):
phenyl group,
a p-biphenyl group,
m-biphenyl group,
an o-biphenyl group,
p-terphenyl-4-yl group,
p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
anthryl group,
benzoanthryl group,
a phenanthryl group,
a benzophenanthryl group,
a phenalenyl group,
a pyrenyl group,
a chrysenyl group,
a benzochrysenyl group,
a triphenylenyl group,
a benzotriphenylenyl group,
a tetracenyl group,
pentacenyl group,
fluorenyl group,
9,9′-spirobifluorenyl group,
benzofluorenyl group,
a dibenzofluorenyl group,
a fluoranthenyl group,
a benzofluoranthenyl group,
A perylenyl group and a monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
・置換のアリール基（具体例群Ｇ１Ｂ）：
ｏ－トリル基、
ｍ－トリル基、
ｐ－トリル基、
パラ－キシリル基、
メタ－キシリル基、
オルト－キシリル基、
パラ－イソプロピルフェニル基、
メタ－イソプロピルフェニル基、
オルト－イソプロピルフェニル基、
パラ－ｔ－ブチルフェニル基、
メタ－ｔ－ブチルフェニル基、
オルト－ｔ－ブチルフェニル基、
３，４，５－トリメチルフェニル基、
９，９－ジメチルフルオレニル基、
９，９－ジフェニルフルオレニル基
９，９－ビス（４－メチルフェニル）フルオレニル基、
９，９－ビス（４－イソプロピルフェニル）フルオレニル基、
９，９－ビス（４－ｔ－ブチルフェニル）フルオレニル基、
シアノフェニル基、
トリフェニルシリルフェニル基、
トリメチルシリルフェニル基、
フェニルナフチル基、
ナフチルフェニル基、及び
前記一般式（ＴＥＭＰ－１）～（ＴＥＭＰ－１５）で表される環構造から誘導される１価の基の１つ以上の水素原子が置換基と置き換わった基。 - Substituted aryl group (specific example group G1B):
an o-tolyl group,
m-tolyl group,
p-tolyl group,
para-xylyl group,
meta-xylyl group,
an ortho-xylyl group,
para-isopropylphenyl group,
meta-isopropylphenyl group,
an ortho-isopropylphenyl group,
para-t-butylphenyl group,
meta-t-butylphenyl group,
ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group,
9,9-bis(4-isopropylphenyl)fluorenyl group,
9,9-bis(4-t-butylphenyl) fluorenyl group,
a cyanophenyl group,
a triphenylsilylphenyl group,
a trimethylsilylphenyl group,
a phenylnaphthyl group,
A naphthylphenyl group and a group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the general formulas (TEMP-1) to (TEMP-15) is replaced with a substituent.
・「置換もしくは無置換の複素環基」
　本明細書に記載の「複素環基」は、環形成原子にヘテロ原子を少なくとも１つ含む環状の基である。ヘテロ原子の具体例としては、窒素原子、酸素原子、硫黄原子、ケイ素原子、リン原子、及びホウ素原子が挙げられる。
　本明細書に記載の「複素環基」は、単環の基であるか、又は縮合環の基である。
　本明細書に記載の「複素環基」は、芳香族複素環基であるか、又は非芳香族複素環基である。
　本明細書に記載の「置換もしくは無置換の複素環基」の具体例（具体例群Ｇ２）としては、以下の無置換の複素環基（具体例群Ｇ２Ａ）、及び置換の複素環基（具体例群Ｇ２Ｂ）等が挙げられる。（ここで、無置換の複素環基とは「置換もしくは無置換の複素環基」が「無置換の複素環基」である場合を指し、置換の複素環基とは「置換もしくは無置換の複素環基」が「置換の複素環基」である場合を指す。）本明細書において、単に「複素環基」という場合は、「無置換の複素環基」と「置換の複素環基」の両方を含む。
　「置換の複素環基」は、「無置換の複素環基」の１つ以上の水素原子が置換基と置き換わった基を意味する。「置換の複素環基」の具体例は、下記具体例群Ｇ２Ａの「無置換の複素環基」の水素原子が置き換わった基、及び下記具体例群Ｇ２Ｂの置換の複素環基の例等が挙げられる。尚、ここに列挙した「無置換の複素環基」の例や「置換の複素環基」の例は、一例に過ぎず、本明細書に記載の「置換の複素環基」には、具体例群Ｇ２Ｂの「置換の複素環基」における複素環基自体の環形成原子に結合する水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ２Ｂの「置換の複素環基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・"Substituted or unsubstituted heterocyclic group"
As used herein, a "heterocyclic group" is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
A "heterocyclic group" as described herein is a monocyclic group or a condensed ring group.
A "heterocyclic group" as described herein is either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
Specific examples of the "substituted or unsubstituted heterocyclic group" described herein (specific example group G2) include the following unsubstituted heterocyclic groups (specific example group G2A), and substituted heterocyclic groups ( Specific example group G2B) and the like can be mentioned. (Here, unsubstituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”, and substituted heterocyclic group refers to “substituted or unsubstituted "Heterocyclic group" refers to a "substituted heterocyclic group".) In the present specification, simply referring to a "heterocyclic group" means "unsubstituted heterocyclic group" and "substituted heterocyclic group". including both.
A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups of the following specific example group G2B. mentioned. The examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described herein specifically includes A group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of Example Group G2B is further replaced with a substituent, and a substituent in the "substituted heterocyclic group" of Specific Example Group G2B A group in which the hydrogen atom of is further replaced with a substituent is also included.
　具体例群Ｇ２Ａは、例えば、以下の窒素原子を含む無置換の複素環基（具体例群Ｇ２Ａ１）、酸素原子を含む無置換の複素環基（具体例群Ｇ２Ａ２）、硫黄原子を含む無置換の複素環基（具体例群Ｇ２Ａ３）、及び下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から１つの水素原子を除くことにより誘導される１価の複素環基（具体例群Ｇ２Ａ４）を含む。 Specific example group G2A includes, for example, the following nitrogen atom-containing unsubstituted heterocyclic groups (specific example group G2A1), oxygen atom-containing unsubstituted heterocyclic groups (specific example group G2A2), sulfur atom-containing unsubstituted (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
　具体例群Ｇ２Ｂは、例えば、以下の窒素原子を含む置換の複素環基（具体例群Ｇ２Ｂ１）、酸素原子を含む置換の複素環基（具体例群Ｇ２Ｂ２）、硫黄原子を含む置換の複素環基（具体例群Ｇ２Ｂ３）、及び下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基の１つ以上の水素原子が置換基と置き換わった基（具体例群Ｇ２Ｂ４）を含む。 Specific example group G2B includes, for example, the following substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), substituted heterocyclic group containing an oxygen atom (specific example group G2B2), substituted heterocyclic ring containing a sulfur atom group (specific example group G2B3), and one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) as a substituent Including substituted groups (example group G2B4).
・窒素原子を含む無置換の複素環基（具体例群Ｇ２Ａ１）：
ピロリル基、
イミダゾリル基、
ピラゾリル基、
トリアゾリル基、
テトラゾリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ピリジル基、
ピリダジニル基、
ピリミジニル基、
ピラジニル基、
トリアジニル基、
インドリル基、
イソインドリル基、
インドリジニル基、
キノリジニル基、
キノリル基、
イソキノリル基、
シンノリル基、
フタラジニル基、
キナゾリニル基、
キノキサリニル基、
ベンゾイミダゾリル基、
インダゾリル基、
フェナントロリニル基、
フェナントリジニル基、
アクリジニル基、
フェナジニル基、
カルバゾリル基、
ベンゾカルバゾリル基、
モルホリノ基、
フェノキサジニル基、
フェノチアジニル基、
アザカルバゾリル基、及びジアザカルバゾリル基。 - an unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):
pyrrolyl group,
an imidazolyl group,
a pyrazolyl group,
a triazolyl group,
a tetrazolyl group,
an oxazolyl group,
an isoxazolyl group,
an oxadiazolyl group,
a thiazolyl group,
an isothiazolyl group,
a thiadiazolyl group,
a pyridyl group,
a pyridazinyl group,
a pyrimidinyl group,
pyrazinyl group,
a triazinyl group,
an indolyl group,
an isoindolyl group,
an indolizinyl group,
a quinolidinyl group,
quinolyl group,
an isoquinolyl group,
cinnolyl group,
a phthalazinyl group,
a quinazolinyl group,
a quinoxalinyl group,
a benzimidazolyl group,
an indazolyl group,
a phenanthrolinyl group,
a phenanthridinyl group,
acridinyl group,
phenazinyl group,
a carbazolyl group,
a benzocarbazolyl group,
a morpholino group,
a phenoxazinyl group,
a phenothiazinyl group,
an azacarbazolyl group and a diazacarbazolyl group;
・酸素原子を含む無置換の複素環基（具体例群Ｇ２Ａ２）：
フリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
キサンテニル基、
ベンゾフラニル基、
イソベンゾフラニル基、
ジベンゾフラニル基、
ナフトベンゾフラニル基、
ベンゾオキサゾリル基、
ベンゾイソキサゾリル基、
フェノキサジニル基、
モルホリノ基、
ジナフトフラニル基、
アザジベンゾフラニル基、
ジアザジベンゾフラニル基、
アザナフトベンゾフラニル基、及び
ジアザナフトベンゾフラニル基。 - an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):
furyl group,
an oxazolyl group,
an isoxazolyl group,
an oxadiazolyl group,
xanthenyl group,
benzofuranyl group,
an isobenzofuranyl group,
a dibenzofuranyl group,
a naphthobenzofuranyl group,
a benzoxazolyl group,
a benzisoxazolyl group,
a phenoxazinyl group,
a morpholino group,
a dinaphthofuranyl group,
an azadibenzofuranyl group,
a diazadibenzofuranyl group,
azanaphthobenzofuranyl group and diazanaphthobenzofuranyl group;
・硫黄原子を含む無置換の複素環基（具体例群Ｇ２Ａ３）：
チエニル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ベンゾチオフェニル基（ベンゾチエニル基）、
イソベンゾチオフェニル基（イソベンゾチエニル基）、
ジベンゾチオフェニル基（ジベンゾチエニル基）、
ナフトベンゾチオフェニル基（ナフトベンゾチエニル基）、
ベンゾチアゾリル基、
ベンゾイソチアゾリル基、
フェノチアジニル基、
ジナフトチオフェニル基（ジナフトチエニル基）、
アザジベンゾチオフェニル基（アザジベンゾチエニル基）、
ジアザジベンゾチオフェニル基（ジアザジベンゾチエニル基）、
アザナフトベンゾチオフェニル基（アザナフトベンゾチエニル基）、及び
ジアザナフトベンゾチオフェニル基（ジアザナフトベンゾチエニル基）。 - an unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):
thienyl group,
a thiazolyl group,
an isothiazolyl group,
a thiadiazolyl group,
benzothiophenyl group (benzothienyl group),
isobenzothiophenyl group (isobenzothienyl group),
dibenzothiophenyl group (dibenzothienyl group),
naphthobenzothiophenyl group (naphthobenzothienyl group),
a benzothiazolyl group,
a benzoisothiazolyl group,
a phenothiazinyl group,
a dinaphthothiophenyl group (dinaphthothienyl group),
azadibenzothiophenyl group (azadibenzothienyl group),
diazadibenzothiophenyl group (diazadibenzothienyl group),
Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group) and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
・下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から１つの水素原子を除くことにより誘導される１価の複素環基（具体例群Ｇ２Ａ４）： - 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):
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
　前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）において、ＸＡ及びＹＡは、それぞれ独立に、酸素原子、硫黄原子、ＮＨ、又はＣＨ２である。ただし、ＸＡ及びＹＡのうち少なくとも１つは、酸素原子、硫黄原子、又はＮＨである。
　前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）において、ＸＡ及びＹＡの少なくともいずれかがＮＨ、又はＣＨ２である場合、前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基には、これらＮＨ、又はＣＨ２から１つの水素原子を除いて得られる１価の基が含まれる。 In general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
In the general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH 2 , in the general formulas (TEMP-16) to (TEMP-33) The monovalent heterocyclic groups derived from the represented ring structures include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 .
・窒素原子を含む置換の複素環基（具体例群Ｇ２Ｂ１）：
（９－フェニル）カルバゾリル基、
（９－ビフェニリル）カルバゾリル基、
（９－フェニル）フェニルカルバゾリル基、
（９－ナフチル）カルバゾリル基、
ジフェニルカルバゾール－９－イル基、
フェニルカルバゾール－９－イル基、
メチルベンゾイミダゾリル基、
エチルベンゾイミダゾリル基、
フェニルトリアジニル基、
ビフェニリルトリアジニル基、
ジフェニルトリアジニル基、
フェニルキナゾリニル基、及び
ビフェニリルキナゾリニル基。 - A substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):
(9-phenyl)carbazolyl group,
(9-biphenylyl)carbazolyl group,
(9-phenyl) phenylcarbazolyl group,
(9-naphthyl)carbazolyl group,
diphenylcarbazol-9-yl group,
a phenylcarbazol-9-yl group,
a methylbenzimidazolyl group,
ethylbenzimidazolyl group,
a phenyltriazinyl group,
a biphenylyltriazinyl group,
a diphenyltriazinyl group,
a phenylquinazolinyl group and a biphenylylquinazolinyl group;
・酸素原子を含む置換の複素環基（具体例群Ｇ２Ｂ２）：
フェニルジベンゾフラニル基、
メチルジベンゾフラニル基、
ｔ－ブチルジベンゾフラニル基、及び
スピロ［９Ｈ－キサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基。 - A substituted heterocyclic group containing an oxygen atom (specific example group G2B2):
phenyldibenzofuranyl group,
methyldibenzofuranyl group,
A t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
・硫黄原子を含む置換の複素環基（具体例群Ｇ２Ｂ３）：
フェニルジベンゾチオフェニル基、
メチルジベンゾチオフェニル基、
ｔ－ブチルジベンゾチオフェニル基、及び
スピロ［９Ｈ－チオキサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基。 - A substituted heterocyclic group containing a sulfur atom (specific example group G2B3):
phenyldibenzothiophenyl group,
a methyldibenzothiophenyl group,
A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
・前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基の１つ以上の水素原子が置換基と置き換わった基（具体例群Ｇ２Ｂ４）： - A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the general formulas (TEMP-16) to (TEMP-33) is replaced with a substituent (specific example group G2B4 ):
　前記「１価の複素環基の１つ以上の水素原子」とは、該１価の複素環基の環形成炭素原子に結合している水素原子、ＸＡ及びＹＡの少なくともいずれかがＮＨである場合の窒素原子に結合している水素原子、及びＸＡ及びＹＡの一方がＣＨ２である場合のメチレン基の水素原子から選ばれる１つ以上の水素原子を意味する。 The "one or more hydrogen atoms of the monovalent heterocyclic group" means that at least one of the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, XA and YA is NH. one or more hydrogen atoms selected from a hydrogen atom bonded to a nitrogen atom when one of XA and YA is CH2, and a hydrogen atom of a methylene group when one of XA and YA is CH2.
・「置換もしくは無置換のアルキル基」
　本明細書に記載の「置換もしくは無置換のアルキル基」の具体例（具体例群Ｇ３）としては、以下の無置換のアルキル基（具体例群Ｇ３Ａ）及び置換のアルキル基（具体例群Ｇ３Ｂ）が挙げられる。（ここで、無置換のアルキル基とは「置換もしくは無置換のアルキル基」が「無置換のアルキル基」である場合を指し、置換のアルキル基とは「置換もしくは無置換のアルキル基」が「置換のアルキル基」である場合を指す。）以下、単に「アルキル基」という場合は、「無置換のアルキル基」と「置換のアルキル基」の両方を含む。
　「置換のアルキル基」は、「無置換のアルキル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルキル基」の具体例としては、下記の「無置換のアルキル基」（具体例群Ｇ３Ａ）における１つ以上の水素原子が置換基と置き換わった基、及び置換のアルキル基（具体例群Ｇ３Ｂ）の例等が挙げられる。本明細書において、「無置換のアルキル基」におけるアルキル基は、鎖状のアルキル基を意味する。そのため、「無置換のアルキル基」は、直鎖である「無置換のアルキル基」、及び分岐状である「無置換のアルキル基」が含まれる。尚、ここに列挙した「無置換のアルキル基」の例や「置換のアルキル基」の例は、一例に過ぎず、本明細書に記載の「置換のアルキル基」には、具体例群Ｇ３Ｂの「置換のアルキル基」におけるアルキル基自体の水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ３Ｂの「置換のアルキル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・"Substituted or unsubstituted alkyl group"
Specific examples of the "substituted or unsubstituted alkyl group" described in the specification (specific example group G3) include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B ). (Here, unsubstituted alkyl group refers to the case where "substituted or unsubstituted alkyl group" is "unsubstituted alkyl group", and substituted alkyl group refers to the case where "substituted or unsubstituted alkyl group" is It refers to a "substituted alkyl group".) Hereinafter, simply referred to as an "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group".
A "substituted alkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (specific example group G3A) are replaced with substituents, and substituted alkyl groups (specific examples Examples of group G3B) and the like can be mentioned. As used herein, 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 examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described herein includes specific example group G3B A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group" of Specific Example Group G3B is further replaced by a substituent included.
・無置換のアルキル基（具体例群Ｇ３Ａ）：
メチル基、
エチル基、
ｎ－プロピル基、
イソプロピル基、
ｎ－ブチル基、
イソブチル基、
ｓ－ブチル基、及び
ｔ－ブチル基。 - 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.
・置換のアルキル基（具体例群Ｇ３Ｂ）：
ヘプタフルオロプロピル基（異性体を含む）、
ペンタフルオロエチル基、
２，２，２－トリフルオロエチル基、及び
トリフルオロメチル基。 - Substituted alkyl group (specific example group G3B):
a heptafluoropropyl group (including isomers),
pentafluoroethyl group,
2,2,2-trifluoroethyl group and trifluoromethyl group;
・「置換もしくは無置換のアルケニル基」
　本明細書に記載の「置換もしくは無置換のアルケニル基」の具体例（具体例群Ｇ４）としては、以下の無置換のアルケニル基（具体例群Ｇ４Ａ）、及び置換のアルケニル基（具体例群Ｇ４Ｂ）等が挙げられる。（ここで、無置換のアルケニル基とは「置換もしくは無置換のアルケニル基」が「無置換のアルケニル基」である場合を指し、「置換のアルケニル基」とは「置換もしくは無置換のアルケニル基」が「置換のアルケニル基」である場合を指す。）本明細書において、単に「アルケニル基」という場合は、「無置換のアルケニル基」と「置換のアルケニル基」の両方を含む。
　「置換のアルケニル基」は、「無置換のアルケニル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルケニル基」の具体例としては、下記の「無置換のアルケニル基」（具体例群Ｇ４Ａ）が置換基を有する基、及び置換のアルケニル基（具体例群Ｇ４Ｂ）の例等が挙げられる。尚、ここに列挙した「無置換のアルケニル基」の例や「置換のアルケニル基」の例は、一例に過ぎず、本明細書に記載の「置換のアルケニル基」には、具体例群Ｇ４Ｂの「置換のアルケニル基」におけるアルケニル基自体の水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ４Ｂの「置換のアルケニル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・ "Substituted or unsubstituted alkenyl group"
Specific examples of the "substituted or unsubstituted alkenyl group" described in the specification (specific example group G4) include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B) and the like. (Here, unsubstituted alkenyl group refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", "substituted alkenyl group" means "substituted or unsubstituted alkenyl group ” is a “substituted alkenyl group”.) In the present specification, simply referring to an “alkenyl group” includes both an “unsubstituted alkenyl group” and a “substituted alkenyl group”.
A "substituted alkenyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include groups in which the following "unsubstituted alkenyl group" (specific example group G4A) has a substituent, and substituted alkenyl groups (specific example group G4B). be done. The examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described herein includes specific example group G4B A group in which the hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkenyl group" of Specific Example Group G4B is further replaced by a substituent included.
・無置換のアルケニル基（具体例群Ｇ４Ａ）：
ビニル基、
アリル基、
１－ブテニル基、
２－ブテニル基、及び
３－ブテニル基。 - Unsubstituted alkenyl group (specific example group G4A):
a vinyl group,
allyl group,
1-butenyl group,
2-butenyl group, and 3-butenyl group.
・置換のアルケニル基（具体例群Ｇ４Ｂ）：
１，３－ブタンジエニル基、
１－メチルビニル基、
１－メチルアリル基、
１，１－ジメチルアリル基、
２－メチルアリル基、及び
１，２－ジメチルアリル基。 - Substituted alkenyl group (specific example group G4B):
1,3-butandienyl group,
1-methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
a 2-methylallyl group and a 1,2-dimethylallyl group;
・「置換もしくは無置換のアルキニル基」
　本明細書に記載の「置換もしくは無置換のアルキニル基」の具体例（具体例群Ｇ５）としては、以下の無置換のアルキニル基（具体例群Ｇ５Ａ）等が挙げられる。（ここで、無置換のアルキニル基とは、「置換もしくは無置換のアルキニル基」が「無置換のアルキニル基」である場合を指す。）以下、単に「アルキニル基」という場合は、「無置換のアルキニル基」と「置換のアルキニル基」の両方を含む。
　「置換のアルキニル基」は、「無置換のアルキニル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルキニル基」の具体例としては、下記の「無置換のアルキニル基」（具体例群Ｇ５Ａ）における１つ以上の水素原子が置換基と置き換わった基等が挙げられる。 ・ "Substituted or unsubstituted alkynyl group"
Specific examples of the "substituted or unsubstituted alkynyl group" described in the specification (specific example group G5) include the following unsubstituted alkynyl groups (specific example group G5A). (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) Hereinafter, simply referred to as "alkynyl group" means "unsubstituted includes both "alkynyl group" and "substituted alkynyl group".
A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents.
・無置換のアルキニル基（具体例群Ｇ５Ａ）：
エチニル基 - Unsubstituted alkynyl group (specific example group G5A):
ethynyl group
・「置換もしくは無置換のシクロアルキル基」
　本明細書に記載の「置換もしくは無置換のシクロアルキル基」の具体例（具体例群Ｇ６）としては、以下の無置換のシクロアルキル基（具体例群Ｇ６Ａ）、及び置換のシクロアルキル基（具体例群Ｇ６Ｂ）等が挙げられる。（ここで、無置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「無置換のシクロアルキル基」である場合を指し、置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「置換のシクロアルキル基」である場合を指す。）本明細書において、単に「シクロアルキル基」という場合は、「無置換のシクロアルキル基」と「置換のシクロアルキル基」の両方を含む。
　「置換のシクロアルキル基」は、「無置換のシクロアルキル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のシクロアルキル基」の具体例としては、下記の「無置換のシクロアルキル基」（具体例群Ｇ６Ａ）における１つ以上の水素原子が置換基と置き換わった基、及び置換のシクロアルキル基（具体例群Ｇ６Ｂ）の例等が挙げられる。尚、ここに列挙した「無置換のシクロアルキル基」の例や「置換のシクロアルキル基」の例は、一例に過ぎず、本明細書に記載の「置換のシクロアルキル基」には、具体例群Ｇ６Ｂの「置換のシクロアルキル基」におけるシクロアルキル基自体の炭素原子に結合する１つ以上の水素原子が置換基と置き換わった基、及び具体例群Ｇ６Ｂの「置換のシクロアルキル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・ "Substituted or unsubstituted cycloalkyl group"
Specific examples of the "substituted or unsubstituted cycloalkyl group" described in the specification (specific example group G6) include the following unsubstituted cycloalkyl groups (specific example group G6A), and substituted cycloalkyl groups ( Specific example group G6B) and the like can be mentioned. (Here, unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group", and substituted cycloalkyl group refers to "substituted or unsubstituted It refers to the case where "cycloalkyl group" is "substituted cycloalkyl group".) In the present specification, simply referring to "cycloalkyl group" means "unsubstituted cycloalkyl group" and "substituted cycloalkyl group". including both.
A "substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group" (specific example group G6A) are replaced with substituents, and substituted cycloalkyl groups (Specific example group G6B) and the like. The examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are only examples, and the "substituted cycloalkyl group" described herein specifically includes A group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the “substituted cycloalkyl group” of Example Group G6B is replaced with a substituent, and in the “substituted cycloalkyl group” of Specific Example Group G6B A group in which a hydrogen atom of a substituent is further replaced with a substituent is also included.
・無置換のシクロアルキル基（具体例群Ｇ６Ａ）：
シクロプロピル基、
シクロブチル基、
シクロペンチル基、
シクロヘキシル基、
１－アダマンチル基、
２－アダマンチル基、
１－ノルボルニル基、及び
２－ノルボルニル基。 - Unsubstituted cycloalkyl group (specific example group G6A):
a cyclopropyl group,
cyclobutyl group,
a cyclopentyl group,
a cyclohexyl group,
1-adamantyl group,
2-adamantyl group,
1-norbornyl group and 2-norbornyl group.
・置換のシクロアルキル基（具体例群Ｇ６Ｂ）：
４－メチルシクロヘキシル基。 - Substituted cycloalkyl group (specific example group G6B):
4-methylcyclohexyl group;
・「－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）で表される基」
　本明細書に記載の－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）で表される基の具体例（具体例群Ｇ７）としては、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）、
－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）、
－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）、及び
－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）
が挙げられる。ここで、
　Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
　Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
　Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
　Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。
　－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）における複数のＧ１は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）における複数のＧ１は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）における複数のＧ６は、互いに同一であるか、又は異なる。 - "A group represented by -Si (R 901 ) (R 902 ) (R 903 )"
Specific examples of the group represented by —Si(R 901 )(R 902 )(R 903 ) described in the specification (specific example group G7) include:
-Si(G1)(G1)(G1),
- Si (G1) (G2) (G2),
- Si (G1) (G1) (G2),
-Si(G2)(G2)(G2),
-Si(G3)(G3)(G3) and -Si(G6)(G6)(G6)
is mentioned. here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
A plurality of G1's in -Si(G1)(G1)(G1) are the same or different from each other.
A plurality of G2 in -Si (G1) (G2) (G2) are the same or different from each other.
A plurality of G1's in -Si(G1)(G1)(G2) are the same or different from each other.
A plurality of G2 in -Si(G2)(G2)(G2) are the same or different from each other.
A plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other.
A plurality of G6 in -Si(G6)(G6)(G6) are the same or different from each other.
・「－Ｏ－（Ｒ９０４）で表される基」
　本明細書に記載の－Ｏ－（Ｒ９０４）で表される基の具体例（具体例群Ｇ８）としては、
－Ｏ（Ｇ１）、
－Ｏ（Ｇ２）、
－Ｏ（Ｇ３）、及び
－Ｏ（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
　Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
　Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
　Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。 - "A group represented by -O- (R 904 )"
Specific examples of the group represented by —O—(R 904 ) described in the specification (specific example group G8) include:
-O(G1),
-O(G2),
-O (G3), and -O (G6)
is mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
・「－Ｓ－（Ｒ９０５）で表される基」
　本明細書に記載の－Ｓ－（Ｒ９０５）で表される基の具体例（具体例群Ｇ９）としては、
－Ｓ（Ｇ１）、
－Ｓ（Ｇ２）、
－Ｓ（Ｇ３）、及び
－Ｓ（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
　Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
　Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
　Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。 - "A group represented by -S- (R 905 )"
Specific examples of the group represented by -S-(R 905 ) described in the specification (specific example group G9) include:
-S(G1),
-S(G2),
-S (G3) and -S (G6)
is mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
・「－Ｎ（Ｒ９０６）（Ｒ９０７）で表される基」
　本明細書に記載の－Ｎ（Ｒ９０６）（Ｒ９０７）で表される基の具体例（具体例群Ｇ１０）としては、
－Ｎ（Ｇ１）（Ｇ１）、
－Ｎ（Ｇ２）（Ｇ２）、
－Ｎ（Ｇ１）（Ｇ２）、
－Ｎ（Ｇ３）（Ｇ３）、及び
－Ｎ（Ｇ６）（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
　Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
　Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
　Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。
　－Ｎ（Ｇ１）（Ｇ１）における複数のＧ１は、互いに同一であるか、又は異なる。
　－Ｎ（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
　－Ｎ（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。
　－Ｎ（Ｇ６）（Ｇ６）における複数のＧ６は、互いに同一であるか、又は異なる。 - "A group represented by -N (R 906 ) (R 907 )"
Specific examples of the group represented by —N(R 906 )(R 907 ) described in the specification (specific example group G10) include:
- N (G1) (G1),
-N(G2)(G2),
- N (G1) (G2),
-N (G3) (G3) and -N (G6) (G6)
is mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
A plurality of G1's in -N(G1)(G1) are the same or different from each other.
A plurality of G2 in -N(G2)(G2) are the same or different from each other.
A plurality of G3s in -N(G3)(G3) are the same or different from each other.
A plurality of G6 in -N(G6)(G6) are the same or different from each other.
・「ハロゲン原子」
　本明細書に記載の「ハロゲン原子」の具体例（具体例群Ｇ１１）としては、フッ素原子、塩素原子、臭素原子、及びヨウ素原子等が挙げられる。 ・"Halogen atom"
Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
・「置換もしくは無置換のフルオロアルキル基」
　本明細書に記載の「置換もしくは無置換のフルオロアルキル基」は、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している少なくとも１つの水素原子がフッ素原子と置き換わった基を意味し、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している全ての水素原子がフッ素原子で置き換わった基（パーフルオロ基）も含む。「無置換のフルオロアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。「置換のフルオロアルキル基」は、「フルオロアルキル基」の１つ以上の水素原子が置換基と置き換わった基を意味する。尚、本明細書に記載の「置換のフルオロアルキル基」には、「置換のフルオロアルキル基」におけるアルキル鎖の炭素原子に結合する１つ以上の水素原子がさらに置換基と置き換わった基、及び「置換のフルオロアルキル基」における置換基の１つ以上の水素原子がさらに置換基と置き換わった基も含まれる。「無置換のフルオロアルキル基」の具体例としては、前記「アルキル基」（具体例群Ｇ３）における１つ以上の水素原子がフッ素原子と置き換わった基の例等が挙げられる。 ・"Substituted or unsubstituted fluoroalkyl group"
The "substituted or unsubstituted fluoroalkyl group" described in this specification means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom. Also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The carbon number of the “unsubstituted fluoroalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification. A "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. In addition, the "substituted fluoroalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and A group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" is further replaced with a substituent is also included. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above "alkyl group" (specific example group G3) are replaced with fluorine atoms.
・「置換もしくは無置換のハロアルキル基」
　本明細書に記載の「置換もしくは無置換のハロアルキル基」は、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している少なくとも１つの水素原子がハロゲン原子と置き換わった基を意味し、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している全ての水素原子がハロゲン原子で置き換わった基も含む。「無置換のハロアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。「置換のハロアルキル基」は、「ハロアルキル基」の１つ以上の水素原子が置換基と置き換わった基を意味する。尚、本明細書に記載の「置換のハロアルキル基」には、「置換のハロアルキル基」におけるアルキル鎖の炭素原子に結合する１つ以上の水素原子がさらに置換基と置き換わった基、及び「置換のハロアルキル基」における置換基の１つ以上の水素原子がさらに置換基と置き換わった基も含まれる。「無置換のハロアルキル基」の具体例としては、前記「アルキル基」（具体例群Ｇ３）における１つ以上の水素原子がハロゲン原子と置き換わった基の例等が挙げられる。ハロアルキル基をハロゲン化アルキル基と称する場合がある。 - "substituted or unsubstituted haloalkyl group"
"Substituted or unsubstituted haloalkyl group" described herein means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom Also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The carbon number of the “unsubstituted haloalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification. A "substituted haloalkyl group" means a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. In addition, the "substituted haloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted haloalkyl group" are further replaced with a substituent group, and a "substituted A group in which one or more hydrogen atoms of the substituent in the "haloalkyl group of" is further replaced with a substituent is also included. Specific examples of the "unsubstituted haloalkyl group" include groups in which one or more hydrogen atoms in the above "alkyl group" (specific example group G3) are replaced with halogen atoms. A haloalkyl group may be referred to as a halogenated alkyl group.
・「置換もしくは無置換のアルコキシ基」
　本明細書に記載の「置換もしくは無置換のアルコキシ基」の具体例としては、－Ｏ（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。「無置換のアルコキシ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。 ・ "Substituted or unsubstituted alkoxy group"
A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group". The carbon number of the "unsubstituted alkoxy group" is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
・「置換もしくは無置換のアルキルチオ基」
　本明細書に記載の「置換もしくは無置換のアルキルチオ基」の具体例としては、－Ｓ（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。「無置換のアルキルチオ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。 ・ "Substituted or unsubstituted alkylthio group"
A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), wherein G3 is the "substituted or unsubstituted alkyl group". The carbon number of the “unsubstituted alkylthio group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
・「置換もしくは無置換のアリールオキシ基」
　本明細書に記載の「置換もしくは無置換のアリールオキシ基」の具体例としては、－Ｏ（Ｇ１）で表される基であり、ここで、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。「無置換のアリールオキシ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０であり、より好ましくは６～１８である。 ・ "Substituted or unsubstituted aryloxy group"
Specific examples of the “substituted or unsubstituted aryloxy group” described in this specification are groups represented by —O(G1), where G1 is the “substituted or an unsubstituted aryl group". The number of ring-forming carbon atoms in the "unsubstituted aryloxy group" is 6-50, preferably 6-30, more preferably 6-18, unless otherwise specified in the specification.
・「置換もしくは無置換のアリールチオ基」
　本明細書に記載の「置換もしくは無置換のアリールチオ基」の具体例としては、－Ｓ（Ｇ１）で表される基であり、ここで、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。「無置換のアリールチオ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０であり、より好ましくは６～１８である。 ・"Substituted or unsubstituted arylthio group"
Specific examples of the "substituted or unsubstituted arylthio group" described in this specification are groups represented by -S(G1), wherein G1 is the "substituted or unsubstituted unsubstituted aryl group". The number of ring-forming carbon atoms in the "unsubstituted arylthio group" is 6-50, preferably 6-30, more preferably 6-18, unless otherwise specified in the specification.
・「置換もしくは無置換のトリアルキルシリル基」
　本明細書に記載の「トリアルキルシリル基」の具体例としては、－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。「トリアルキルシリル基」の各アルキル基の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０であり、より好ましくは１～６である。 ・"Substituted or unsubstituted trialkylsilyl group"
Specific examples of the "trialkylsilyl group" described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the group described in Specific Example Group G3. It is a "substituted or unsubstituted alkyl group". A plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified in the specification.
・「置換もしくは無置換のアラルキル基」
　本明細書に記載の「置換もしくは無置換のアラルキル基」の具体例としては、－（Ｇ３）－（Ｇ１）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」であり、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。従って、「アラルキル基」は、「アルキル基」の水素原子が置換基としての「アリール基」と置き換わった基であり、「置換のアルキル基」の一態様である。「無置換のアラルキル基」は、「無置換のアリール基」が置換した「無置換のアルキル基」であり、「無置換のアラルキル基」の炭素数は、本明細書に別途記載のない限り、７～５０であり、好ましくは７～３０であり、より好ましくは７～１８である。
　「置換もしくは無置換のアラルキル基」の具体例としては、ベンジル基、１－フェニルエチル基、２－フェニルエチル基、１－フェニルイソプロピル基、２－フェニルイソプロピル基、フェニル－ｔ－ブチル基、α－ナフチルメチル基、１－α－ナフチルエチル基、２－α－ナフチルエチル基、１－α－ナフチルイソプロピル基、２－α－ナフチルイソプロピル基、β－ナフチルメチル基、１－β－ナフチルエチル基、２－β－ナフチルエチル基、１－β－ナフチルイソプロピル基、及び２－β－ナフチルイソプロピル基等が挙げられる。 ・"Substituted or unsubstituted aralkyl group"
A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), wherein G3 is the group described in Specific Example Group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one aspect of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms in the "unsubstituted aralkyl group" is unless otherwise specified herein. , 7-50, preferably 7-30, more preferably 7-18.
Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α -naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group , 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.
　本明細書に記載の置換もしくは無置換のアリール基は、本明細書に別途記載のない限り、好ましくはフェニル基、ｐ－ビフェニル基、ｍ－ビフェニル基、ｏ－ビフェニル基、ｐ－ターフェニル－４－イル基、ｐ－ターフェニル－３－イル基、ｐ－ターフェニル－２－イル基、ｍ－ターフェニル－４－イル基、ｍ－ターフェニル－３－イル基、ｍ－ターフェニル－２－イル基、ｏ－ターフェニル－４－イル基、ｏ－ターフェニル－３－イル基、ｏ－ターフェニル－２－イル基、１－ナフチル基、２－ナフチル基、アントリル基、フェナントリル基、ピレニル基、クリセニル基、トリフェニレニル基、フルオレニル基、９，９’－スピロビフルオレニル基、９，９－ジメチルフルオレニル基、及び９，９－ジフェニルフルオレニル基等である。 A substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl- 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.
　本明細書に記載の置換もしくは無置換の複素環基は、本明細書に別途記載のない限り、好ましくはピリジル基、ピリミジニル基、トリアジニル基、キノリル基、イソキノリル基、キナゾリニル基、ベンゾイミダゾリル基、フェナントロリニル基、カルバゾリル基（１－カルバゾリル基、２－カルバゾリル基、３－カルバゾリル基、４－カルバゾリル基、又は９－カルバゾリル基）、ベンゾカルバゾリル基、アザカルバゾリル基、ジアザカルバゾリル基、ジベンゾフラニル基、ナフトベンゾフラニル基、アザジベンゾフラニル基、ジアザジベンゾフラニル基、ジベンゾチオフェニル基、ナフトベンゾチオフェニル基、アザジベンゾチオフェニル基、ジアザジベンゾチオフェニル基、（９－フェニル）カルバゾリル基（（９－フェニル）カルバゾール－１－イル基、（９－フェニル）カルバゾール－２－イル基、（９－フェニル）カルバゾール－３－イル基、又は（９－フェニル）カルバゾール－４－イル基）、（９－ビフェニリル）カルバゾリル基、（９－フェニル）フェニルカルバゾリル基、ジフェニルカルバゾール－９－イル基、フェニルカルバゾール－９－イル基、フェニルトリアジニル基、ビフェニリルトリアジニル基、ジフェニルトリアジニル基、フェニルジベンゾフラニル基、及びフェニルジベンゾチオフェニル基等である。 The substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenyl, unless otherwise stated herein. nantholinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyl group riazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, phenyldibenzothiophenyl group and the like.
　本明細書において、カルバゾリル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。 In the present specification, a carbazolyl group is specifically any one of the following groups unless otherwise specified in the specification.
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000023
　本明細書において、（９－フェニル）カルバゾリル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。 In the present specification, the (9-phenyl)carbazolyl group is specifically any one of the following groups, unless otherwise stated in the specification.
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000024
　前記一般式（ＴＥＭＰ－Ｃｚ１）～（ＴＥＭＰ－Ｃｚ９）中、＊は、結合位置を表す。 In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a binding position.
　本明細書において、ジベンゾフラニル基、及びジベンゾチオフェニル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。 As used herein, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified.
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025
　前記一般式（ＴＥＭＰ－３４）～（ＴＥＭＰ－４１）中、＊は、結合位置を表す。 In the general formulas (TEMP-34) to (TEMP-41), * represents a binding position.
　本明細書に記載の置換もしくは無置換のアルキル基は、本明細書に別途記載のない限り、好ましくはメチル基、エチル基、プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、及びｔ－ブチル基等である。 The substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t- butyl group and the like.
・「置換もしくは無置換のアリーレン基」
　本明細書に記載の「置換もしくは無置換のアリーレン基」は、別途記載のない限り、上記「置換もしくは無置換のアリール基」からアリール環上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換のアリーレン基」の具体例（具体例群Ｇ１２）としては、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」からアリール環上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 ・"Substituted or unsubstituted arylene group"
Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is derived from the above "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. is the base of the valence. Specific examples of the “substituted or unsubstituted arylene group” (specific example group G12) include the “substituted or unsubstituted aryl group” described in specific example group G1 by removing one hydrogen atom on the aryl ring. Induced divalent groups and the like can be mentioned.
・「置換もしくは無置換の２価の複素環基」
　本明細書に記載の「置換もしくは無置換の２価の複素環基」は、別途記載のない限り、上記「置換もしくは無置換の複素環基」から複素環上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換の２価の複素環基」の具体例（具体例群Ｇ１３）としては、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」から複素環上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 ・ "Substituted or unsubstituted divalent heterocyclic group"
Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described herein is the above "substituted or unsubstituted heterocyclic group" except that one hydrogen atom on the heterocyclic ring is removed. is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocyclic ring from the "substituted or unsubstituted heterocyclic group" described in specific example group G2. Examples include divalent groups derived by removing atoms.
・「置換もしくは無置換のアルキレン基」
　本明細書に記載の「置換もしくは無置換のアルキレン基」は、別途記載のない限り、上記「置換もしくは無置換のアルキル基」からアルキル鎖上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換のアルキレン基」の具体例（具体例群Ｇ１４）としては、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」からアルキル鎖上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 ・ "Substituted or unsubstituted alkylene group"
Unless otherwise specified, the "substituted or unsubstituted alkylene group" described herein is derived from the above "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. is the base of the valence. Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include the “substituted or unsubstituted alkyl group” described in specific example group G3 by removing one hydrogen atom on the alkyl chain. Induced divalent groups and the like can be mentioned.
　本明細書に記載の置換もしくは無置換のアリーレン基は、本明細書に別途記載のない限り、好ましくは下記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－６８）のいずれかの基である。 The substituted or unsubstituted arylene group described in this specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027
　前記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－５２）中、Ｑ１～Ｑ１０は、それぞれ独立に、水素原子、又は置換基である。
　前記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－５２）中、＊は、結合位置を表す。 In general formulas (TEMP-42) to (TEMP-52), Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
In the general formulas (TEMP-42) to (TEMP-52), * represents a binding position.
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000028
　前記一般式（ＴＥＭＰ－５３）～（ＴＥＭＰ－６２）中、Ｑ１～Ｑ１０は、それぞれ独立に、水素原子、又は置換基である。
　式Ｑ９及びＱ１０は、単結合を介して互いに結合して環を形成してもよい。
　前記一般式（ＴＥＭＰ－５３）～（ＴＥＭＰ－６２）中、＊は、結合位置を表す。 In general formulas (TEMP-53) to (TEMP-62), Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
Formulas Q9 and Q10 may be linked together through a single bond to form a ring.
In the general formulas (TEMP-53) to (TEMP-62), * represents a binding position.
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000029
　前記一般式（ＴＥＭＰ－６３）～（ＴＥＭＰ－６８）中、Ｑ１～Ｑ８は、それぞれ独立に、水素原子、又は置換基である。
　前記一般式（ＴＥＭＰ－６３）～（ＴＥＭＰ－６８）中、＊は、結合位置を表す。 In general formulas (TEMP-63) to (TEMP-68), Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
In the general formulas (TEMP-63) to (TEMP-68), * represents a binding position.
　本明細書に記載の置換もしくは無置換の２価の複素環基は、本明細書に別途記載のない限り、好ましくは下記一般式（ＴＥＭＰ－６９）～（ＴＥＭＰ－１０２）のいずれかの基である。 The substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein is.
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032
　前記一般式（ＴＥＭＰ－６９）～（ＴＥＭＰ－８２）中、Ｑ１～Ｑ９は、それぞれ独立に、水素原子、又は置換基である。 In general formulas (TEMP-69) to (TEMP-82), Q 1 to Q 9 are each independently a hydrogen atom or a substituent.
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000036
Figure JPOXMLDOC01-appb-C000036
　前記一般式（ＴＥＭＰ－８３）～（ＴＥＭＰ－１０２）中、Ｑ１～Ｑ８は、それぞれ独立に、水素原子、又は置換基である。 In general formulas (TEMP-83) to (TEMP-102), Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
　以上が、「本明細書に記載の置換基」についての説明である。 The above is the description of the "substituents described in this specification".
・「結合して環を形成する場合」
　本明細書において、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合せず」という場合は、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合と、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合と、「隣接する２つ以上からなる組の１組以上が、互いに結合しない」場合と、を意味する。
　本明細書における、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合、及び「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合（以下、これらの場合をまとめて「結合して環を形成する場合」と称する場合がある。）について、以下、説明する。母骨格がアントラセン環である下記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物の場合を例として説明する。 ・"When combining to form a ring"
As used herein, "one or more pairs of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted condensed ring. The phrases "form or are not bonded to each other" refer to "at least one pair of two or more adjacent pairs bonded together to form a substituted or unsubstituted monocyclic ring" and "adjacent are bonded to each other to form a substituted or unsubstituted condensed ring" and "one or more adjacent pairs of two or more are not bonded to each other. ' means if.
In the present specification, when "one or more pairs of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic ring", and "one of two or more adjacent pairs In the case where two or more groups combine with each other to form a substituted or unsubstituted condensed ring (hereinafter, these cases may be collectively referred to as "the case where they combine to form a ring"), the following ,explain. An anthracene compound represented by the following general formula (TEMP-103) having an anthracene ring as a base skeleton will be described as an example.
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000037
　例えば、Ｒ９２１～Ｒ９３０のうちの「隣接する２つ以上からなる組の１組以上が、互いに結合して、環を形成する」場合において、１組となる隣接する２つからなる組とは、Ｒ９２１とＲ９２２との組、Ｒ９２２とＲ９２３との組、Ｒ９２３とＲ９２４との組、Ｒ９２４とＲ９３０との組、Ｒ９３０とＲ９２５との組、Ｒ９２５とＲ９２６との組、Ｒ９２６とＲ９２７との組、Ｒ９２７とＲ９２８との組、Ｒ９２８とＲ９２９との組、並びにＲ９２９とＲ９２１との組である。 For example, when "one or more pairs of two or more adjacent pairs of R 921 to R 930 are combined to form a ring", is a pair of R 921 and R 922 , a pair of R 922 and R 923 , a pair of R 923 and R 924 , a pair of R 924 and R 930 , a pair of R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R 929 and R 921 .
　上記「１組以上」とは、上記隣接する２つ以上からなる組の２組以上が同時に環を形成してもよいことを意味する。例えば、Ｒ９２１とＲ９２２とが互いに結合して環ＱＡを形成し、同時にＲ９２５とＲ９２６とが互いに結合して環ＱＢを形成した場合は、前記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物は、下記一般式（ＴＥＭＰ－１０４）で表される。 The above-mentioned "one or more pairs" means that two or more of the groups consisting of two or more adjacent groups may form a ring at the same time. For example, when R 921 and R 922 are bonded together to form ring Q A , and R 925 and R 926 are bonded together to form ring Q B , the general formula (TEMP-103) The represented anthracene compound is represented by the following general formula (TEMP-104).
Figure JPOXMLDOC01-appb-C000038
Figure JPOXMLDOC01-appb-C000038
　「隣接する２つ以上からなる組」が環を形成する場合とは、前述の例のように隣接する「２つ」からなる組が結合する場合だけではなく、隣接する「３つ以上」からなる組が結合する場合も含む。例えば、Ｒ９２１とＲ９２２とが互いに結合して環ＱＡを形成し、かつ、Ｒ９２２とＲ９２３とが互いに結合して環ＱＣを形成し、互いに隣接する３つ（Ｒ９２１、Ｒ９２２及びＲ９２３）からなる組が互いに結合して環を形成して、アントラセン母骨格に縮合する場合を意味し、この場合、前記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物は、下記一般式（ＴＥＭＰ－１０５）で表される。下記一般式（ＴＥＭＰ－１０５）において、環ＱＡ及び環ＱＣは、Ｒ９２２を共有する。 The case where "a group consisting of two or more adjacent pairs" forms a ring is not limited to the case where a group consisting of two adjacent "two" is combined as in the above example, but It also includes the case where a pair is combined. For example, R 921 and R 922 are bonded together to form ring Q A , and R 922 and R 923 are bonded together to form ring Q C , and the adjacent three (R 921 , R 922 and R 923 ) are combined to form a ring and condensed to the anthracene base skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) has It is represented by the general formula (TEMP-105). In the general formula (TEMP-105) below, ring Q A and ring Q C share R 922 .
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-C000039
　形成される「単環」、又は「縮合環」は、形成された環のみの構造として、飽和の環であっても不飽和の環であってもよい。「隣接する２つからなる組の１組」が「単環」、又は「縮合環」を形成する場合であっても、当該「単環」、又は「縮合環」は、飽和の環、又は不飽和の環を形成することができる。例えば、前記一般式（ＴＥＭＰ－１０４）において形成された環ＱＡ及び環ＱＢは、それぞれ、「単環」又は「縮合環」である。また、前記一般式（ＴＥＭＰ－１０５）において形成された環ＱＡ、及び環ＱＣは、「縮合環」である。前記一般式（ＴＥＭＰ－１０５）の環ＱＡと環ＱＣとは、環ＱＡと環ＱＣとが縮合することによって縮合環となっている。前記一般式（ＴＥＭＰ－１０４）の環ＱＡがベンゼン環であれば、環ＱＡは、単環である。前記一般式（ＴＥＭＰ－１０４）の環ＱＡがナフタレン環であれば、環ＱＡは、縮合環である。 The "monocyclic ring" or "condensed ring" to be formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one pair of adjacent pairs" forms a "single ring" or a "fused ring", the "single ring" or "fused ring" is a saturated ring, or Unsaturated rings can be formed. For example, ring Q A and ring Q B formed in the general formula (TEMP-104) are each a "monocyclic ring" or a "fused ring". Moreover, the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”. The ring Q A and the ring Q C in the general formula (TEMP-105) form a condensed ring by condensing the ring Q A and the ring Q C. If the ring Q A in the general formula (TEMP-104) is a benzene ring, the ring Q A is monocyclic. When the ring Q A of the general formula (TEMP-104) is a naphthalene ring, the ring Q A is a condensed ring.
　「不飽和の環」とは、芳香族炭化水素環、又は芳香族複素環を意味する。「飽和の環」とは、脂肪族炭化水素環、又は非芳香族複素環を意味する。
　芳香族炭化水素環の具体例としては、具体例群Ｇ１において具体例として挙げられた基が水素原子によって終端された構造が挙げられる。
　芳香族複素環の具体例としては、具体例群Ｇ２において具体例として挙げられた芳香族複素環基が水素原子によって終端された構造が挙げられる。
　脂肪族炭化水素環の具体例としては、具体例群Ｇ６において具体例として挙げられた基が水素原子によって終端された構造が挙げられる。
　「環を形成する」とは、母骨格の複数の原子のみ、あるいは母骨格の複数の原子とさらに１以上の任意の元素で環を形成することを意味する。例えば、前記一般式（ＴＥＭＰ－１０４）に示す、Ｒ９２１とＲ９２２とが互いに結合して形成された環ＱＡは、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２が結合するアントラセン骨格の炭素原子と、１以上の任意の元素とで形成する環を意味する。具体例としては、Ｒ９２１とＲ９２２とで環ＱＡを形成する場合において、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２とが結合するアントラセン骨格の炭素原子と、４つの炭素原子とで単環の不飽和の環を形成する場合、Ｒ９２１とＲ９２２とで形成する環は、ベンゼン環である。 "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. A "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.
Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in the specific example group G1 are terminated with a hydrogen atom.
Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups listed as specific examples in the specific example group G2 are terminated with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in the specific example group G6 are terminated with a hydrogen atom.
"Forming a ring" means forming a ring only with a plurality of atoms of the mother skeleton, or with a plurality of atoms of the mother skeleton and one or more arbitrary elements. For example, the ring Q A formed by combining R 921 and R 922 shown in the general formula (TEMP-104) has the carbon atom of the anthracene skeleton to which R 921 is bonded and the anthracene skeleton to which R 922 is bonded. It means a ring formed by a skeleton carbon atom and one or more arbitrary elements. As a specific example, when R 921 and R 922 form a ring Q A , the carbon atom of the anthracene skeleton to which R 921 is bound, the carbon atom of the anthracene skeleton to which R 922 is bound, and four carbon atoms and form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.
　ここで、「任意の元素」は、本明細書に別途記載のない限り、好ましくは、炭素元素、窒素元素、酸素元素、及び硫黄元素からなる群から選択される少なくとも１種の元素である。任意の元素において（例えば、炭素元素、又は窒素元素の場合）、環を形成しない結合は、水素原子等で終端されてもよいし、後述する「任意の置換基」で置換されてもよい。炭素元素以外の任意の元素を含む場合、形成される環は複素環である。
　単環または縮合環を構成する「１以上の任意の元素」は、本明細書に別途記載のない限り、好ましくは２個以上１５個以下であり、より好ましくは３個以上１２個以下であり、さらに好ましくは３個以上５個以下である。
　本明細書に別途記載のない限り、「単環」、及び「縮合環」のうち、好ましくは「単環」である。
　本明細書に別途記載のない限り、「飽和の環」、及び「不飽和の環」のうち、好ましくは「不飽和の環」である。
　本明細書に別途記載のない限り、「単環」は、好ましくはベンゼン環である。
　本明細書に別途記載のない限り、「不飽和の環」は、好ましくはベンゼン環である。
　「隣接する２つ以上からなる組の１組以上」が、「互いに結合して、置換もしくは無置換の単環を形成する」場合、又は「互いに結合して、置換もしくは無置換の縮合環を形成する」場合、本明細書に別途記載のない限り、好ましくは、隣接する２つ以上からなる組の１組以上が、互いに結合して、母骨格の複数の原子と、１個以上１５個以下の炭素元素、窒素元素、酸素元素、及び硫黄元素からなる群から選択される少なくとも１種の元素とからなる置換もしくは無置換の「不飽和の環」を形成する。 Here, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise specified in this specification. In any element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "optional substituent" described later. When it contains any element other than the carbon atom, the ring formed is a heterocycle.
"One or more arbitrary elements" constituting a monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, unless otherwise specified in the present specification. , more preferably 3 or more and 5 or less.
Among "monocyclic ring" and "condensed ring", "monocyclic ring" is preferred, unless otherwise stated in the present specification.
Of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred, unless otherwise specified in the present specification.
Unless otherwise stated herein, "monocyclic" is preferably a benzene ring.
Unless otherwise stated herein, the "unsaturated ring" is preferably a benzene ring.
When "one or more pairs of two or more adjacent pairs" are "bonded to each other to form a substituted or unsubstituted monocyclic ring", or "bonded to each other to form a substituted or unsubstituted condensed ring When forming, unless otherwise stated herein, preferably one or more sets of two or more adjacent groups are bonded together to form a plurality of atoms of the backbone and 1 or more 15 It forms a substituted or unsubstituted "unsaturated ring" with at least one element selected from the group consisting of the following carbon, nitrogen, oxygen and sulfur elements.
　上記の「単環」、又は「縮合環」が置換基を有する場合の置換基は、例えば後述する「任意の置換基」である。上記の「単環」、又は「縮合環」が置換基を有する場合の置換基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基である。
　上記の「飽和の環」、又は「不飽和の環」が置換基を有する場合の置換基は、例えば後述する「任意の置換基」である。上記の「単環」、又は「縮合環」が置換基を有する場合の置換基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基である。
　以上が、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合、及び「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合（「結合して環を形成する場合」）についての説明である。 When the above "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents in the case where the above "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section "Substituents described herein" above.
When the above "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents in the case where the above "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section "Substituents described herein" above.
The above is the case where "one or more pairs of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic ring", and "one or more pairs of two or more adjacent pairs are combined with each other to form a substituted or unsubstituted condensed ring"("combine to form a ring").
・「置換もしくは無置換の」という場合の置換基
　本明細書における一実施形態においては、前記「置換もしくは無置換の」という場合の置換基（本明細書において、「任意の置換基」と呼ぶことがある。）は、例えば、無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、及び
無置換の環形成原子数５～５０の複素環基
からなる群から選択される基等であり、
　ここで、Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の複素環基である。
　Ｒ９０１が２個以上存在する場合、２個以上のＲ９０１は、互いに同一であるか、又は異なり、
　Ｒ９０２が２個以上存在する場合、２個以上のＲ９０２は、互いに同一であるか、又は異なり、
　Ｒ９０３が２個以上存在する場合、２個以上のＲ９０３は、互いに同一であるか、又は異なり、
　Ｒ９０４が２個以上存在する場合、２個以上のＲ９０４は、互いに同一であるか、又は異なり、
　Ｒ９０５が２個以上存在する場合、２個以上のＲ９０５は、互いに同一であるか、又は異なり、
　Ｒ９０６が２個以上存在する場合、２個以上のＲ９０６は、互いに同一であるか、又は異なり、
　Ｒ９０７が２個以上存在する場合、２個以上のＲ９０７は、互いに同一であるか又は異なる。 - Substituent in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (herein referred to as "optional substituent") ) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms,
an unsubstituted alkenyl group having 2 to 50 carbon atoms,
an unsubstituted alkynyl group having 2 to 50 carbon atoms,
an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R 901 ) (R 902 ) (R 903 ),
—O—(R 904 ),
-S-(R 905 ),
-N(R 906 )(R 907 ),
halogen atom, cyano group, nitro group,
a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms;
Here, R 901 to R 907 are each independently
hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
when two or more R 901 are present, the two or more R 901 are the same or different from each other,
when two or more R 902 are present, the two or more R 902 are the same or different from each other;
when two or more R 903 are present, the two or more R 903 are the same or different from each other,
when two or more R 904 are present, the two or more R 904 are the same or different from each other;
when two or more R 905 are present, the two or more R 905 are the same or different from each other,
when two or more R 906 are present, the two or more R 906 are the same or different from each other;
When two or more R 907 are present, the two or more R 907 are the same or different from each other.
　一実施形態においては、前記「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の複素環基
からなる群から選択される基である。 In one embodiment, the substituents referred to above as "substituted or unsubstituted" are
an alkyl group having 1 to 50 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
　一実施形態においては、前記「置換もしくは無置換の」という場合の置換基は、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、及び
環形成原子数５～１８の複素環基
からなる群から選択される基である。 In one embodiment, the substituents referred to above as "substituted or unsubstituted" are
an alkyl group having 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
　上記任意の置換基の各基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基の具体例である。 Specific examples of each group of the above optional substituents are specific examples of the substituents described in the section "Substituents described in the specification" above.
　本明細書において別途記載のない限り、隣接する任意の置換基同士で、「飽和の環」、又は「不飽和の環」を形成してもよく、好ましくは、置換もしくは無置換の飽和の５員環、置換もしくは無置換の飽和の６員環、置換もしくは無置換の不飽和の５員環、又は置換もしくは無置換の不飽和の６員環を形成し、より好ましくは、ベンゼン環を形成する。
　本明細書において別途記載のない限り、任意の置換基は、さらに置換基を有してもよい。任意の置換基がさらに有する置換基としては、上記任意の置換基と同様である。 Unless otherwise stated in this specification, any adjacent substituents may form a “saturated ring” or an “unsaturated ring”, preferably a substituted or unsubstituted saturated 5 forming a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
Unless stated otherwise herein, any substituent may have further substituents. Substituents further possessed by the optional substituents are the same as the above optional substituents.
　本明細書において、「ＡＡ～ＢＢ」を用いて表される数値範囲は、「ＡＡ～ＢＢ」の前に記載される数値ＡＡを下限値とし、「ＡＡ～ＢＢ」の後に記載される数値ＢＢを上限値として含む範囲を意味する。 In this specification, the numerical range represented using "AA to BB" has the numerical value AA described before "AA to BB" as the lower limit, and the numerical value BB described after "AA to BB" as the upper limit.
　以下、本発明の化合物を説明する。
　本発明の化合物は下記式（１）で表される。ただし、以下、式（１）及び後述する式（１）に含まれる式で表される本発明の化合物を単に“発明化合物”と称することがある。
Figure JPOXMLDOC01-appb-C000040
 The compounds of the present invention are described below.
The compound of the present invention is represented by the following formula (1). However, hereinafter, the compounds of the present invention represented by formula (1) and formulas included in formula (1) described later may be simply referred to as "invention compounds".
Figure JPOXMLDOC01-appb-C000040
　以下、式（１）及び後述する式（１）に含まれる式中の記号を説明する。なお、同じ記号は同じ意味を有する。 The symbols in formula (1) and formula (1) to be described later will be described below. The same symbols have the same meanings.
　式（１）中、
　Ｎ＊は中心窒素原子であり、
　Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、及びＲ１Ｄ～Ｒ５Ｄは、それぞれ独立して、水素原子、無置換の炭素数１～６のアルキル基、又は無置換の環形成炭素数６～１２のアリール基である。
　ただし、
　Ｒ１Ａ～Ｒ５Ａから選ばれる１つは＊ａに結合する単結合であり、
　Ｒ１Ｂ～Ｒ５Ｂから選ばれる１つは＊ｂに結合する単結合であり、
　Ｒ１Ｄ～Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、
　前記単結合ではないＲ１Ａ～Ｒ５Ａから選ばれる隣接する２つ、前記単結合ではないＲ１Ｂ～Ｒ５Ｂから選ばれる隣接する２つ、及び前記単結合ではないＲ１Ｄ～Ｒ５Ｄから選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成せず、
　ベンゼン環Ａとベンゼン環Ｂは架橋しない。 In formula (1),
N * is the central nitrogen atom,
R 1A to R 5A , R 1B to R 5B , and R 1D to R 5D are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted 6 to 6 ring carbon atoms. 12 aryl groups.
however,
one selected from R 1A to R 5A is a single bond that binds to *a;
one selected from R 1B to R 5B is a single bond that bonds to *b;
one selected from R 1D to R 5D is a single bond that bonds to *d;
Adjacent two selected from R 1A to R 5A which are not single bonds, adjacent two selected from R 1B to R 5B which are not single bonds, and R 1D to R 5D which are not single bonds adjacent two are not bonded to each other and thus do not form a ring structure;
Benzene ring A and benzene ring B are not crosslinked.
　Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、及びＲ１Ｄ～Ｒ５Ｄが表す前記無置換の炭素数１～６のアルキル基は、好ましくはメチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｓ－ブチル基、又はｔ－ブチル基であり、より好ましくはメチル基、エチル基、イソプロピル基、又はｔ－ブチル基であり、さらに好ましくはメチル基又はｔ－ブチル基である。 The unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 1A to R 5A , R 1B to R 5B and R 1D to R 5D is preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group or t-butyl group, more preferably methyl group, ethyl group, isopropyl group or t-butyl group, still more preferably methyl group or t-butyl group is the base.
　Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、及びＲ１Ｄ～Ｒ５Ｄが表す前記無置換の環形成炭素数６～１２のアリール基は、好ましくはフェニル基、ビフェニルイル基、又はナフチル基であり、より好ましくはフェニル基、又はナフチル基であり、さらに好ましくはフェニル基である。 The unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R 1A to R 5A , R 1B to R 5B and R 1D to R 5D is preferably a phenyl group, a biphenylyl group or a naphthyl group. , more preferably a phenyl group or a naphthyl group, and still more preferably a phenyl group.
　本発明の一態様において、Ｒ３Ａは＊ａに結合する単結合であることが好ましい。
　また、本発明の一態様において、Ｒ２Ｂ～Ｒ４Ｂから選ばれる１つは＊ｂに結合する単結合であることが好ましく、Ｒ３Ｂは＊ｂに結合する単結合であることがより好ましい。
　また、本発明の一態様において、Ｒ２Ｄ～Ｒ４Ｄから選ばれる１つは＊ｄに結合する単結合であることが好ましく、Ｒ３Ｄは＊ｄに結合する単結合であることがより好ましい。 In one aspect of the present invention, R 3A is preferably a single bond attached to *a.
In one aspect of the present invention, one selected from R 2B to R 4B is preferably a single bond that bonds to *b, and R 3B is more preferably a single bond that bonds to *b.
In one aspect of the present invention, one selected from R 2D to R 4D is preferably a single bond that bonds to *d, and R 3D is more preferably a single bond that bonds to *d.
　単結合ではないＲ１Ａ～Ｒ５Ａ、単結合ではないＲ１Ｂ～Ｒ５Ｂ、単結合ではないＲ１Ｄ～Ｒ５Ｄは、水素原子であることが好ましい。 R 1A to R 5A that are not single bonds, R 1B to R 5B that are not single bonds, and R 1D to R 5D that are not single bonds are preferably hydrogen atoms.
　ｍは０又は１である。
　ただし、ｍが０のとき、＊ｄが中心窒素原子Ｎ＊に結合する。
　本発明の一態様において、ｍは０であることが好ましい。
　本発明の他の態様において、ｍは１であることが好ましい。 m is 0 or 1;
However, when m is 0, *d is bound to the central nitrogen atom N * .
In one aspect of the present invention, m is preferably 0.
In another aspect of the invention, m is preferably one.
　Ｒ１Ｃ～Ｒ４Ｃ、Ｒ１Ｕ～Ｒ８Ｕ、及びＲ１Ｖ～Ｒ８Ｖは、水素原子である。
　ただし、
　Ｒ１Ｕ～Ｒ８Ｕから選ばれる１つは＊ｕに結合する単結合であり、
　Ｒ１Ｖ～Ｒ８Ｖから選ばれる１つは＊ｖに結合する単結合であり、
　ベンゼン環Ｂとナフタレン環Ｕ、ベンゼン環Ｃとナフタレン環Ｖは、架橋しない。 R 1C to R 4C , R 1U to R 8U and R 1V to R 8V are hydrogen atoms.
however,
one selected from R 1U to R 8U is a single bond that binds to *u;
one selected from R 1V to R 8V is a single bond that binds to *v;
Benzene ring B and naphthalene ring U and benzene ring C and naphthalene ring V are not crosslinked.
　本発明の一態様において、Ｒ１Ｕ、Ｒ４Ｕ、Ｒ５Ｕ、及びＲ８Ｕから選ばれる１つが＊ｕに結合する単結合であることが好ましい。
　また、本発明の一態様において、Ｒ１Ｖ、Ｒ４Ｖ、Ｒ５Ｖ、及びＲ８Ｖから選ばれる１つが＊ｖに結合する単結合であることが好ましい。 In one aspect of the present invention, one selected from R 1U , R 4U , R 5U and R 8U is preferably a single bond that binds to *u.
In one aspect of the present invention, one selected from R 1V , R 4V , R 5V and R 8V is preferably a single bond that binds to *v.
　Ａｒは、下記式（１－ａ）～（１－ｅ）のいずれかで表される。 Ar is represented by any one of the following formulas (1-a) to (1-e).
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-C000041
　式（１－ａ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ１～Ｒ５は、それぞれ独立して、水素原子、無置換の炭素数１～６のアルキル基、又は無置換のフェニル基である。
　ただし、
　前記Ｒ１～Ｒ５から選ばれる１つは＊ｅに結合する単結合であり、前記Ｒ１～Ｒ５から選ばれる他の１つは＊ｆに結合する単結合であり、
　前記単結合ではないＲ１～Ｒ５から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成せず、
　ｍが１でｎが１でｌが０のとき下記（ｉ）又は（ｉｉ）を満たし、
　ｍが１でｎが０でｌが１のとき、下記（ｉｉｉ）又は（ｉｖ）を満たす。
（ｉ）Ｒ３Ｄは＊ｄに結合する単結合であり、Ｒ１、Ｒ２、Ｒ４、及びＲ５から選ばれる１つは＊ｅに結合する単結合である。
（ｉｉ）Ｒ１Ｄ、Ｒ２Ｄ、Ｒ４Ｄ、Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、Ｒ１～Ｒ５から選ばれる１つは＊ｅに結合する単結合である。
（ｉｉｉ）Ｒ３Ｄは＊ｄに結合する単結合であり、Ｒ１、Ｒ２、Ｒ４、及びＲ５から選ばれる１つは＊ｆに結合する単結合である。
（ｉｖ）Ｒ１Ｄ、Ｒ２Ｄ、Ｒ４Ｄ、Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、Ｒ１～Ｒ５から選ばれる１つは＊ｆに結合する単結合である。 In formula (1-a),
** represents the binding position to the above *d.
R 1 to R 5 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group.
however,
one selected from R 1 to R 5 is a single bond that bonds to *e, and the other one selected from R 1 to R 5 is a single bond that bonds to *f;
adjacent two selected from R 1 to R 5 which are not single bonds are not bonded to each other and therefore do not form a ring structure;
When m is 1, n is 1, and l is 0, the following (i) or (ii) is satisfied,
When m is 1, n is 0, and l is 1, the following (iii) or (iv) is satisfied.
(i) R 3D is a single bond bonded to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond bonded to *e;
(ii) one selected from R 1D , R 2D , R 4D and R 5D is a single bond that bonds to *d, and one selected from R 1 to R 5 is a single bond that bonds to *e .
(iii) R 3D is a single bond that bonds to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond that bonds to *f.
(iv) one selected from R 1D , R 2D , R 4D and R 5D is a single bond that binds to *d, and one selected from R 1 to R 5 is a single bond that binds to *f .
　Ｒ１～Ｒ５が表す前記無置換の炭素数１～６のアルキル基は、Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、及びＲ１Ｄ～Ｒ５Ｄにおいて上記したとおりであり、好ましい基等についても同じである。 The unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 1 to R 5 is as described above for R 1A to R 5A , R 1B to R 5B , and R 1D to R 5D . is the same.
　単結合ではないＲ１～Ｒ５は、水素原子であることが好ましい。 R 1 to R 5 that are not single bonds are preferably hydrogen atoms.
　Ａｒ１１及びＡｒ１２は、下記式（ｉ）で表される基である。 Ar 11 and Ar 12 are groups represented by the following formula (i).
Figure JPOXMLDOC01-appb-C000042
Figure JPOXMLDOC01-appb-C000042
　式（ｉ）中、
　＊＊＊は、結合位置を表す。
　Ｒ１１～Ｒ１５は、それぞれ独立して、水素原子又は無置換の炭素数１～６のアルキル基である。
　ただし、
　Ｒ１１～Ｒ１５から選ばれる隣接する２つ、及びＲ２１～Ｒ２５から選ばれる隣接する２つは、互いに結合して、置換もしくは無置換のベンゼン環を形成してもよい。 In formula (i),
*** represents the binding position.
R 11 to R 15 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms.
however,
Two adjacent groups selected from R 11 to R 15 and two adjacent groups selected from R 21 to R 25 may combine with each other to form a substituted or unsubstituted benzene ring.
　Ｒ１１～Ｒ１５が表す前記無置換の炭素数１～６のアルキル基は、Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、及びＲ１Ｄ～Ｒ５Ｄにおいて上記したとおりであり、好ましい基等についても同じである。 The unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 11 to R 15 is as described above for R 1A to R 5A , R 1B to R 5B and R 1D to R 5D . is the same.
　単結合ではないＲ１１～Ｒ１５は、水素原子であることが好ましい。 R 11 to R 15 that are not single bonds are preferably hydrogen atoms.
　式（１－ａ）中、ｎは０～２の整数であり、ｎが０のとき、（Ａｒ１１）０は水素原子を表わし、
　ｌは０～２の整数であり、ｌが０のとき、（Ａｒ１２）０は水素原子を表わす。 In formula (1-a), n is an integer of 0 to 2, and when n is 0, (Ar 11 ) 0 represents a hydrogen atom;
l is an integer of 0 to 2, and when l is 0, (Ar 12 ) 0 represents a hydrogen atom.
　本発明の一態様において、ｎは０であってもよく、本発明の他の態様において、ｎは１であってもよく、本発明のさらに他の態様において、ｎは２であってもよい。
　本発明の一態様において、ｌは０であってもよく、本発明の他の態様において、ｌは１であってもよく、本発明のさらに他の態様において、ｌは２であってもよい。 In one aspect of the invention, n may be 0, in another aspect of the invention, n may be 1, and in yet another aspect of the invention, n may be 2. .
In one aspect of the invention, l may be 0, in another aspect of the invention, l may be 1, and in yet another aspect of the invention, l may be 2. .
　式（１－ａ）は、好ましくは下記式で表される。下記式においてＲは簡略化のために省略した。 Formula (1-a) is preferably represented by the following formula. In the following formula, R is omitted for simplification.
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000044
　式（１－ｂ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ２１～Ｒ２８は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
　ただし、
　前記Ｒ２１～Ｒ２８から選ばれる１つは＊ｇに結合する単結合であり、前記Ｒ２１～Ｒ２８から選ばれる他の１つは＊ｈに結合する単結合であり、前記Ｒ２１～Ｒ２８から選ばれるさらに他の１つは＊ｉに結合する単結合であり、
　前記単結合ではないＲ２１～Ｒ２８から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。 In formula (1-b),
** represents the binding position to the above *d.
R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
however,
One selected from R 21 to R 28 is a single bond that bonds to *g, the other one selected from R 21 to R 28 is a single bond that bonds to *h, and R 21 to Still another one selected from R 28 is a single bond attached to *i,
Adjacent two groups selected from R 21 to R 28 which are not single bonds are not bonded to each other and therefore do not form a ring structure.
　Ｒ２１～Ｒ２８が表す前記置換もしくは無置換の炭素数１～６のアルキル基は、好ましくはメチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｓ－ブチル基、又はｔ－ブチル基であり、より好ましくはメチル基、エチル基、イソプロピル基、又はｔ－ブチル基であり、さらに好ましくはメチル基又はｔ－ブチル基である。 The substituted or unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 21 to R 28 is preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl or t-butyl group, more preferably methyl group, ethyl group, isopropyl group, or t-butyl group, still more preferably methyl group or t-butyl group.
　Ｒ２１～Ｒ２８が表す前記置換もしくは無置換の環形成炭素数６～１２のアリール基は、好ましくはフェニル基、ビフェニルイル基、又はナフチル基であり、より好ましくはフェニル基、又はナフチル基であり、さらに好ましくはフェニル基である。 The substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by R 21 to R 28 is preferably a phenyl group, a biphenylyl group or a naphthyl group, more preferably a phenyl group or a naphthyl group. and more preferably a phenyl group.
　単結合ではないＲ２１～Ｒ２８は、水素原子であることが好ましい。 R 21 to R 28 which are not single bonds are preferably hydrogen atoms.
　本発明の一態様において、Ｒ２１、Ｒ２４、Ｒ２５、及びＲ２８から選ばれる１つは＊ｇに結合する単結合であることが好ましい。
　また、本発明の一態様において、Ｒ２１、Ｒ２４、Ｒ２５、及びＲ２８から選ばれる他の１つは＊ｈに結合する単結合であることが好ましく、Ｒ２１、Ｒ２４、Ｒ２５、及びＲ２８から選ばれるさらに他の１つは＊ｉに結合する単結合であることが好ましい。 In one aspect of the present invention, one selected from R 21 , R 24 , R 25 and R 28 is preferably a single bond that bonds to *g.
In one aspect of the present invention, the other one selected from R 21 , R 24 , R 25 and R 28 is preferably a single bond that binds to *h, and R 21 , R 24 and R 25 , and R 28 is preferably a single bond that bonds to *i.
　Ａｒ１３及びＡｒ１４は、下記式（ｉｉ）で表される基である。 Ar 13 and Ar 14 are groups represented by the following formula (ii).
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000045
　式（ｉｉ）中、
　＊＊＊は、結合位置を表す。
　Ｒ３１～Ｒ３５は、水素原子である。 In formula (ii),
*** represents the binding position.
R 31 to R 35 are hydrogen atoms.
　式（１－ｂ）中、
　ｏは０、又は１であり、ｏが０のとき（Ａｒ１３）０は水素原子を表わし、
　ｐは０、又は１であり、ｐが０のとき（Ａｒ１４）０は水素原子を表わす。 In formula (1-b),
o is 0 or 1, and when o is 0 (Ar 13 ) 0 represents a hydrogen atom;
p is 0 or 1, and (Ar 14 ) 0 represents a hydrogen atom when p is 0;
　本発明の一態様において、ｏは０であってもよく、本発明の他の態様において、ｏは１であってもよい。
　本発明の一態様において、ｐは０であってもよく、本発明の他の態様において、ｐは１であってもよい。 In one aspect of the invention, o may be 0, and in another aspect of the invention, o may be 1.
In one aspect of the invention, p may be 0, and in another aspect of the invention, p may be 1.
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000046
　式（１－ｃ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ４１～Ｒ５２は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
　ただし、
　前記Ｒ４１～Ｒ５２から選ばれる１つは＊ｊに結合する単結合であり、前記Ｒ４１～Ｒ５２から選ばれる他の１つは＊ｋに結合する単結合であり、前記Ｒ４１～Ｒ５２から選ばれるさらに他の１つは＊ｌに結合する単結合であり、
　前記単結合ではないＲ４１～Ｒ５２から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。 In formula (1-c),
** represents the binding position to the above *d.
R 41 to R 52 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
however,
One selected from R 41 to R 52 is a single bond that bonds to *j, the other one selected from R 41 to R 52 is a single bond that bonds to *k, and R 41 to Further one selected from R 52 is a single bond attached to *l,
Adjacent two selected from R 41 to R 52 which are not single bonds are not bonded to each other and thus do not form a ring structure.
　Ｒ４１～Ｒ５２が表す前記置換もしくは無置換の炭素数１～６のアルキル基は、Ｒ２１～Ｒ２８において上記したとおりであり、好ましい基等についても同じである。 The substituted or unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 41 to R 52 is as described above for R 21 to R 28 , and the preferred groups are also the same.
　Ｒ４１～Ｒ５２が表す前記置換もしくは無置換の環形成炭素数６～１２のアリール基は、Ｒ２１～Ｒ２８において上記したとおりであり、好ましい基等についても同じである。 The substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by R 41 to R 52 is as described above for R 21 to R 28 , and preferred groups are also the same.
　単結合ではないＲ４１～Ｒ５２は、水素原子であることが好ましい。 R 41 to R 52 that are not single bonds are preferably hydrogen atoms.
　Ａｒ１５及びＡｒ１６は、前記式（ｉｉ）で表される基である。
　ｑは０、又は１であり、ｑが０のとき（Ａｒ１５）０は水素原子を表わし、
　ｒは０、又は１であり、ｒが０のとき（Ａｒ１６）０は水素原子を表わす。 Ar 15 and Ar 16 are groups represented by the above formula (ii).
q is 0 or 1, and when q is 0 (Ar 15 ) 0 represents a hydrogen atom;
r is 0 or 1, and (Ar 16 ) 0 represents a hydrogen atom when r is 0;
　本発明の一態様において、ｑは０であってもよく、本発明の他の態様において、ｑは１であってもよい。
　本発明の一態様において、ｒは０であってもよく、本発明の他の態様において、ｒは１であってもよい。 In one aspect of the invention, q may be 0, and in another aspect of the invention, q may be 1.
In one aspect of the invention, r may be 0, and in another aspect of the invention, r may be 1.
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000047
　式（１－ｄ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ６１～Ｒ７０は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
　ただし、
　前記Ｒ６１～Ｒ７０から選ばれる１つは＊ｍに結合する単結合であり、前記Ｒ６１～Ｒ７０から選ばれる他の１つは＊ｎに結合する単結合であり、前記Ｒ６１～Ｒ７０から選ばれるさらに他の１つは＊ｏに結合する単結合であり、
　前記単結合ではないＲ６１～Ｒ７０から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。 In formula (1-d),
** represents the binding position to the above *d.
R 61 to R 70 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
however,
One selected from R 61 to R 70 is a single bond that bonds to *m, the other one selected from R 61 to R 70 is a single bond that bonds to *n, and R 61 to Still another one selected from R 70 is a single bond attached to *o,
Adjacent two groups selected from R 61 to R 70 which are not single bonds are not bonded to each other and therefore do not form a ring structure.
　Ｒ６１～Ｒ７０が表す前記置換もしくは無置換の炭素数１～６のアルキル基は、Ｒ２１～Ｒ２８において上記したとおりであり、好ましい基等についても同じである。 The substituted or unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 61 to R 70 is as described above for R 21 to R 28 , and the preferred groups are also the same.
　Ｒ６１～Ｒ７０が表す前記置換もしくは無置換の環形成炭素数６～１２のアリール基は、Ｒ２１～Ｒ２８において上記したとおりであり、好ましい基等についても同じである。 The substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by R 61 to R 70 is as described above for R 21 to R 28 , and preferred groups are also the same.
　単結合ではないＲ６１～Ｒ７０は、水素原子であることが好ましい。 R 61 to R 70 which are not single bonds are preferably hydrogen atoms.
　本発明の一態様において、Ｒ６９、及びＲ７０から選ばれる１つは＊ｍに結合する単結合であることが好ましい。
　また、本発明の一態様において、Ｒ６９、及びＲ７０から選ばれる他の１つは＊ｎ又は＊ｏに結合する単結合であることが好ましい。 In one aspect of the present invention, one selected from R 69 and R 70 is preferably a single bond that bonds to *m.
In one aspect of the present invention, the other one selected from R 69 and R 70 is preferably a single bond that binds to *n or *o.
　Ａｒ１7及びＡｒ１８は、前記式（ｉｉ）で表される基である。
　ｓは０、又は１であり、ｓが０のとき（Ａｒ１７）０は水素原子を表わし、
　ｔは０、又は１であり、ｔが０のとき（Ａｒ１８）０は水素原子を表わす。 Ar 17 and Ar 18 are groups represented by the above formula (ii).
s is 0 or 1, and when s is 0 (Ar 17 ) 0 represents a hydrogen atom,
t is 0 or 1, and (Ar 18 ) 0 represents a hydrogen atom when t is 0;
　本発明の一態様において、ｓは０であってもよく、本発明の他の態様において、ｓは１であってもよい。
　本発明の一態様において、ｔは０であってもよく、本発明の他の態様において、ｔは１であってもよい。 In one aspect of the invention, s may be 0, and in another aspect of the invention, s may be 1.
In one aspect of the invention, t may be 0, and in another aspect of the invention, t may be 1.
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000048
　式（１－ｅ）中、
　＊＊は、前記＊ｄへの結合位置を表す。
　Ｒ８１～Ｒ８８は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
　ＲＡ及びＲＢは、それぞれ独立して、メチル基、置換もしくは無置換のフェニル基である。
　ただし、
　＊ｐは、前記Ｒ８１～Ｒ８８、ＲＡ及びＲＢから選ばれる１つに結合し、
　ＲＡ又はＲＢが＊ｌに結合する場合、＊ｌに結合するＲＡ又はＲＢはメチレン基又は置換もしくは無置換のフェニレン基であり、
　前記Ｒ８１～Ｒ８８から選ばれる１つが＊ｌに結合する場合、＊ｌに結合する前記Ｒ８１～Ｒ８８から選ばれる１つは単結合であり、
　前記単結合ではないＲ８１～Ｒ８８から選ばれる隣接する２つは、互いに結合して、置換もしくは無置換のベンゼン環を形成してもよく、
　＊ｌに結合しないＲＡとＲＢが結合して、スピロ環を形成してもよい。 In formula (1-e),
** represents the binding position to the above *d.
R 81 to R 88 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
R A and R B are each independently a methyl group or a substituted or unsubstituted phenyl group.
however,
* p is bound to one selected from R 81 to R 88 , R A and R B ;
when R A or R B is attached to *l, R A or R B attached to *l is a methylene group or a substituted or unsubstituted phenylene group;
when one selected from R 81 to R 88 is bonded to *l, one selected from R 81 to R 88 bonded to *l is a single bond;
Adjacent two selected from R 81 to R 88 which are not single bonds may be bonded to each other to form a substituted or unsubstituted benzene ring,
* R A and R B that are not bonded to l may combine to form a spiro ring.
　Ｒ８１～Ｒ８８が表す前記置換もしくは無置換の炭素数１～６のアルキル基は、Ｒ２１～Ｒ２８において上記したとおりであり、好ましい基等についても同じである。 The substituted or unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 81 to R 88 is as described above for R 21 to R 28 , and the preferred groups are also the same.
　Ｒ８１～Ｒ８８が表す前記置換もしくは無置換の環形成炭素数６～１２のアリール基は、Ｒ２１～Ｒ２８において上記したとおりであり、好ましい基等についても同じである。 The substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by R 81 to R 88 is as described above for R 21 to R 28 , and preferred groups are also the same.
　本発明の一態様において、ＲＡ及びＲＢは、メチル基であってもよく、置換もしくは無置換のフェニル基であってもよく、一方がメチル基であり、他方が置換もしくは無置換のフェニル基であってもよい。 In one aspect of the present invention, R A and R B may be a methyl group or a substituted or unsubstituted phenyl group, one being a methyl group and the other being a substituted or unsubstituted phenyl may be a base.
　Ａｒは、前記式（１－ａ）、（１－ｂ）又は（１－ｄ）で表されることが好ましく、前記式（１－ｂ）又は（１－ｄ）で表されることがより好ましい。
　本発明の一態様において、Ａｒは前記式（１－ｂ）で表される場合、ｍは０であることが好ましい。
　本発明の他の態様において、Ａｒは前記式（１－ａ）又は（１－ｄ）で表される場合、ｍは１であることが好ましい。 Ar is preferably represented by the formula (1-a), (1-b) or (1-d), more preferably represented by the formula (1-b) or (1-d) preferable.
In one aspect of the present invention, m is preferably 0 when Ar is represented by the formula (1-b).
In another aspect of the present invention, m is preferably 1 when Ar is represented by formula (1-a) or (1-d).
　発明化合物は、下記式（１－１）で表される化合物であることが好ましく、下記式（１－２）で表される化合物であることがより好ましい。 The invention compound is preferably a compound represented by the following formula (1-1), more preferably a compound represented by the following formula (1-2).
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000049
　式（１－１）中、
　Ｎ＊、Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、Ｒ１Ｃ～Ｒ４Ｃ、Ｒ１Ｄ～Ｒ５Ｄ、Ｒ２Ｕ～Ｒ８Ｕ、Ｒ１Ｖ～Ｒ７Ｖ、Ａｒ、ｍ、＊ａ、＊ｂ、＊ｄ、ベンゼン環Ａ～ベンゼン環Ｄ、ナフタレン環Ｕ、及びナフタレン環Ｖは、式（１）で定義したとおりである。 In formula (1-1),
N * , R1A to R5A , R1B to R5B, R1C to R4C, R1D to R5D, R2U to R8U, R1V to R7V , Ar , m , * a , *b, * d, benzene ring A to benzene ring D, naphthalene ring U, and naphthalene ring V are as defined in formula (1).
Figure JPOXMLDOC01-appb-C000050
Figure JPOXMLDOC01-appb-C000050
　式（１－２）中、
　Ｎ＊、Ｒ１Ａ、Ｒ２Ａ、Ｒ４Ａ、Ｒ５Ａ、Ｒ１Ｂ、Ｒ２Ｂ、Ｒ４Ｂ、Ｒ５Ｂ、Ｒ１Ｃ～Ｒ４Ｃ、Ｒ１Ｄ～Ｒ５Ｄ、Ｒ２Ｕ～Ｒ８Ｕ、Ｒ１Ｖ～Ｒ７Ｖ、Ａｒ、ｍ、＊ｄ、ベンゼン環Ａ～ベンゼン環Ｄ、ナフタレン環Ｕ、及びナフタレン環Ｖは、式（１）で定義したとおりである。 In formula (1-2),
N * , R 1A , R 2A , R 4A , R 5A , R 1B , R 2B , R 4B , R 5B , R 1C to R 4C , R 1D to R 5D , R 2U to R 8U , R 1V to R 7V , Ar, m, *d, benzene ring A to benzene ring D, naphthalene ring U, and naphthalene ring V are as defined in formula (1).
　本発明の一態様において、
（Ａ－１）＊ａに結合する単結合ではないＲ１Ａ～Ｒ５Ａのすべてが水素原子であってもよく、
（Ａ－２）＊ｂに結合する単結合ではないＲ１Ｂ～Ｒ５Ｂのすべてが水素原子であってもよく、
（Ａ－３）Ｒ１Ｃ～Ｒ４Ｃのすべてが水素原子であってもよく、
（Ａ－４）＊ｄに結合する単結合ではないＲ１Ｄ～Ｒ５Ｄのすべてが水素原子であってもよく、
（Ａ－５）＊ｕに結合する単結合ではないＲ１Ｕ～Ｒ８Ｕのすべてが水素原子であってもよく、
（Ａ－６）＊ｖに結合する単結合ではないＲ１Ｖ～Ｒ８Ｖのすべてが水素原子であってもよく、
（Ａ－７）＊ｅ及び＊ｆに結合する単結合ではないＲ１～Ｒ５のすべてが水素原子であってもよく、
（Ａ－８）Ｒ１１～Ｒ１５のすべてが水素原子であってもよく、
（Ａ－９）＊ｇ、＊ｈ、及び＊ｉに結合する単結合ではないＲ２１～Ｒ２８のすべてが水素原子であってもよく、
（Ａ－１０）Ｒ３１～Ｒ３５のすべてが水素原子であってもよく、
（Ａ－１１）＊ｊ、＊ｋ、及び＊ｌに結合する単結合ではないＲ４１～Ｒ５２のすべてが水素原子であってもよく、
（Ａ－１２）＊ｍ、＊ｎ、及び＊ｏに結合する単結合ではないＲ６１～Ｒ７０のすべてが水素原子であってもよく、
（Ａ－１３）＊ｐに結合する単結合ではないＲ８１～Ｒ８８のすべてが水素原子であってもよい。
  In one aspect of the present invention,
(A-1) All of R 1A to R 5A that are not single bonds bonded to *a may be hydrogen atoms,
(A-2) All of R 1B to R 5B that are not single bonds bonded to *b may be hydrogen atoms,
(A-3) all of R 1C to R 4C may be hydrogen atoms;
(A-4) All of R 1D to R 5D that are not single bonds bonded to *d may be hydrogen atoms,
(A-5) All of R 1U to R 8U that are not single bonds bonded to *u may be hydrogen atoms,
(A-6) All of R 1V to R 8V that are not single bonds bonded to *v may be hydrogen atoms,
(A-7) all of R 1 to R 5 that are not single bonds bonded to *e and *f may be hydrogen atoms;
(A-8) all of R 11 to R 15 may be hydrogen atoms,
(A-9) all of R 21 to R 28 that are not single bonds bonded to *g, *h, and *i may be hydrogen atoms;
(A-10) all of R 31 to R 35 may be hydrogen atoms,
(A-11) all of R 41 to R 52 that are not single bonds bonded to *j, *k, and *l may be hydrogen atoms;
(A-12) all of R 61 to R 70 that are not single bonds bonded to *m, *n, and *o may be hydrogen atoms;
All of R 81 to R 88 which are not single bonds bonded to (A-13)*p may be hydrogen atoms.
　上記したように、本明細書において使用する「水素原子」は軽水素原子、重水素原子、及び三重水素原子を包含する。従って、発明化合物は天然由来の重水素原子を含んでいてもよい。
　又、原料化合物の一部又は全てに重水素化した化合物を使用することにより、発明化合物Ａに重水素原子を意図的に導入してもよい。従って、本発明の一態様において、発明化合物は少なくとも１個の重水素原子を含む。すなわち、発明化合物は、式（１）で表される化合物であって、該化合物に含まれる水素原子の少なくとも一つが重水素原子である化合物であってもよい。 As noted above, "hydrogen atom" as used herein includes protium, deuterium, and tritium atoms. Accordingly, invention compounds may contain naturally occurring deuterium atoms.
Alternatively, deuterium atoms may be intentionally introduced into the invention compound A by using a deuterated compound as part or all of the raw material compound. Accordingly, in one aspect of the invention, the compounds of the invention contain at least one deuterium atom. That is, the compound of the invention may be a compound represented by formula (1) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.
　単結合ではないＲ１Ａ～Ｒ５Ａのいずれかが表す水素原子；単結合ではないＲ１Ａ～Ｒ５Ａのいずれかが表す無置換のアルキル基、又はアリール基が有する水素原子；
　単結合ではないＲ１Ｂ～Ｒ５Ｂのいずれかが表す水素原子；単結合ではないＲ１Ｂ～Ｒ５Ｂのいずれかが表す無置換のアルキル基、又はアリール基が有する水素原子；
　Ｒ１Ｃ～Ｒ４Ｃのいずれかが表す水素原子；
　単結合ではないＲ１Ｄ～Ｒ５Ｄのいずれかが表す水素原子；単結合ではないＲ１Ｄ～Ｒ５Ｄのいずれかが表す無置換のアルキル基、又はアリール基が有する水素原子；
　単結合ではないＲ１Ｕ～Ｒ８Ｕのいずれかが表す水素原子；
　単結合ではないＲ１Ｖ～Ｒ８Ｖのいずれかが表す水素原子；
　単結合ではないＲ１～Ｒ５のいずれかが表す水素原子；単結合ではないＲ１～Ｒ５のいずれかが表す無置換のアルキル基、又はフェニル基が有する水素原子；
　Ｒ１１～Ｒ１５のいずれかが表す水素原子；Ｒ１１～Ｒ１５のいずれかが表す無置換のアルキル基が有する水素原子；
　単結合ではないＲ２１～Ｒ２８のいずれかが表す水素原子；単結合ではないＲ２１～Ｒ２８のいずれかが表す置換もしくは無置換のアルキル基、又はアリール基が有する水素原子；
　Ｒ３１～Ｒ３５のいずれかが表す水素原子；Ｒ３１～Ｒ３５のいずれかが表す無置換のアルキル基、又はアリール基が有する水素原子；
　単結合ではないＲ４１～Ｒ５２のいずれかが表す水素原子；単結合ではないＲ４１～Ｒ５２のいずれかが表す置換もしくは無置換のアルキル基、又はアリール基が有する水素原子；
　単結合ではないＲ６１～Ｒ７０のいずれかが表す水素原子；単結合ではないＲ６１～Ｒ７０のいずれかが表す無置換のアルキル基、又はアリール基が有する水素原子；
　単結合ではないＲ８１～Ｒ８８のいずれかが表す水素原子；単結合ではないＲ８１～Ｒ８８のいずれかが表す無置換のアルキル基、又はアリール基が有する水素原子；
　ＲＡ及びＲＢのいずれかが表すメチル基、メチレン基、置換もしくは無置換のフェニル基、又はフェニレン基が有する水素原子から選ばれる少なくとも一つの水素原子が重水素原子であってもよい。 A hydrogen atom represented by any one of R 1A to R 5A which is not a single bond; A hydrogen atom possessed by an unsubstituted alkyl group or an aryl group represented by any one of R 1A to R 5A which is not a single bond;
A hydrogen atom represented by any one of R 1B to R 5B which is not a single bond; A hydrogen atom possessed by an unsubstituted alkyl group or an aryl group represented by any one of R 1B to R 5B which is not a single bond;
a hydrogen atom represented by any one of R 1C to R 4C ;
A hydrogen atom represented by any one of R 1D to R 5D which is not a single bond; A hydrogen atom possessed by an unsubstituted alkyl group or an aryl group represented by any one of R 1D to R 5D which is not a single bond;
a hydrogen atom represented by any one of R 1U to R 8U which is not a single bond;
a hydrogen atom represented by any one of R 1V to R 8V which is not a single bond;
A hydrogen atom represented by any one of R 1 to R 5 which is not a single bond; A hydrogen atom possessed by an unsubstituted alkyl group or a phenyl group represented by any one of R 1 to R 5 which is not a single bond;
a hydrogen atom represented by any one of R 11 to R 15 ; a hydrogen atom possessed by an unsubstituted alkyl group represented by any one of R 11 to R 15 ;
hydrogen atom represented by any one of R 21 to R 28 which is not a single bond; hydrogen atom possessed by a substituted or unsubstituted alkyl group or aryl group represented by any one of R 21 to R 28 which is not a single bond;
hydrogen atom represented by any one of R 31 to R 35 ; hydrogen atom possessed by an unsubstituted alkyl group or aryl group represented by any one of R 31 to R 35 ;
hydrogen atom represented by any one of R 41 to R 52 which is not a single bond; hydrogen atom possessed by a substituted or unsubstituted alkyl group or aryl group represented by any one of R 41 to R 52 which is not a single bond;
hydrogen atom represented by any one of R 61 to R 70 which is not a single bond; hydrogen atom possessed by an unsubstituted alkyl group or aryl group represented by any one of R 61 to R 70 which is not a single bond;
hydrogen atom represented by any one of R 81 to R 88 which is not a single bond; hydrogen atom possessed by an unsubstituted alkyl group or aryl group represented by any one of R 81 to R 88 which is not a single bond;
At least one hydrogen atom selected from hydrogen atoms of a methyl group, a methylene group, a substituted or unsubstituted phenyl group, or a phenylene group represented by any one of RA and RB may be a deuterium atom.
　発明化合物の重水素化率は、使用する原料化合物の重水素化率に依存する。所定の重水素化率の原料を用いたとしても、天然由来の一定の割合で軽水素同位体が含まれ得る。従って、下記で示される発明化合物の重水素化率の態様は、単に化学式で表される重水素原子の数をカウントして求められる割合に対し、天然由来の微量の同位体を考慮した比率が含まれる。
　発明化合物の重水素化率は、好ましくは１％以上、より好ましくは３％以上、さらに好ましくは５％以上、よりさらに好ましくは１０％以上、よりさらに好ましくは５０％以上である。 The deuteration rate of the invention compound depends on the deuteration rate of the starting compound used. Even if a raw material with a given deuteration rate is used, it may still contain a certain proportion of natural proton isotopes. Therefore, the aspect of the deuteration rate of the compound of the invention shown below is the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula, and the ratio in consideration of trace isotopes derived from nature. included.
The deuteration rate of the compound of the invention is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more.
　発明化合物は、重水素化された化合物と重水素化されていない化合物を含む混合物、異なる重水素化率を有する２以上の化合物の混合物であってもよい。このような混合物の重水素化率は、好ましくは１％以上、より好ましくは３％以上、さらに好ましくは５％以上、よりさらに好ましくは１０％以上、よりさらに好ましくは５０％以上、かつ、１００％未満である。
また、発明化合物中の全水素原子数に対する重水素原子数の割合は、好ましくは１％以上、より好ましくは３％以上、さらに好ましくは５％以上、よりさらに好ましくは１０％以上、かつ、１００％以下である。 Invention compounds may be mixtures containing deuterated and non-deuterated compounds, mixtures of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and 100% or more. %.
Further, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the invention is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more, and 100 % or less.
　上記各式の定義に含まれる「置換もしくは無置換の」という場合の置換基（任意の置換基）の詳細は、「「置換もしくは無置換の」という場合の置換基」において記載したとおりである。 Details of the substituents (optional substituents) in the case of “substituted or unsubstituted” included in the definition of each formula above are as described in “Substituents in the case of “substituted or unsubstituted””. .
　発明化合物は、当業者であれば、下記合成例及び公知の合成方法を参考にして容易に製造することができる。 Invention compounds can be easily produced by those skilled in the art by referring to the following synthesis examples and known synthesis methods.
　以下に発明化合物の具体例を示すが、以下の例示化合物に限定されるものではない。
　下記具体例中、Ｄは重水素原子を示す。 Specific examples of the compounds of the invention are shown below, but are not limited to the following exemplary compounds.
In the following specific examples, D represents a deuterium atom.
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000055
Figure JPOXMLDOC01-appb-C000055
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000057
Figure JPOXMLDOC01-appb-C000057
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000061
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Figure JPOXMLDOC01-appb-C000217
有機ＥＬ素子用材料
　本発明の一態様である有機ＥＬ素子用材料は発明化合物を含む。有機ＥＬ素子用材料における発明化合物の含有量は、１質量％以上（１００％を含む）であり、１０質量％以上（１００％を含む）であることが好ましく、５０質量％以上（１００％を含む）であることがより好ましく、８０質量％以上（１００％を含む）であることがさらに好ましく、９０質量％以上（１００％を含む）であることが特に好ましい。本発明の一態様である有機ＥＬ素子用材料は、有機ＥＬ素子の製造に有用である。 Organic EL Device Material The organic EL device material that is one aspect of the present invention contains the invention compound. The content of the invention compound in the organic EL device material is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), and 50% by mass or more (including 100% more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The organic EL device material, which is one aspect of the present invention, is useful for manufacturing organic EL devices.
有機ＥＬ素子
　本発明の一態様である有機ＥＬ素子は陽極、陰極、及び該陽極と陰極の間に配置された有機層を含む。該有機層は発光層を含み、該有機層の少なくとも一層が発明化合物を含む。
　発明化合物が含まれる有機層の例としては、陽極と発光層との間に設けられる正孔輸送帯域（正孔注入層、正孔輸送層、電子阻止層、励起子阻止層等）、発光層、スペース層、陰極と発光層との間に設けられる電子輸送帯域（電子注入層、電子輸送層、正孔阻止層等）等が挙げられるが、これらに限定されるものではない。発明化合物は好ましくは蛍光又は燐光ＥＬ素子の正孔輸送帯域又は発光層の材料、より好ましくは正孔輸送帯域の材料、更に好ましくは正孔注入層、正孔輸送層、電子阻止層、又は励起子阻止層の材料、特に好ましくは正孔注入層又は正孔輸送層の材料として用いられる。 Organic EL Element An organic EL element that is one aspect of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layers comprise a light-emitting layer, and at least one layer of the organic layers comprises an invention compound.
Examples of the organic layer containing the compound of the invention include a hole-transporting zone provided between the anode and the light-emitting layer (hole-injection layer, hole-transporting layer, electron-blocking layer, exciton-blocking layer, etc.), light-emitting layer . The inventive compound is preferably a material for the hole-transporting zone or light-emitting layer of a fluorescent or phosphorescent EL device, more preferably a material for the hole-transporting zone, even more preferably a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, or an excitation layer. It is used as a material for electron-blocking layers, particularly preferably as a material for hole-injecting layers or hole-transporting layers.
　本発明の一態様である有機ＥＬ素子は、蛍光又は燐光発光型の単色発光素子であっても、蛍光／燐光ハイブリッド型の白色発光素子であってもよいし、単独の発光ユニットを有するシンプル型であっても、複数の発光ユニットを有するタンデム型であってもよく、中でも、蛍光発光型の素子であることが好ましい。ここで、「発光ユニット」とは、有機層を含み、そのうちの少なくとも一層が発光層であり、注入された正孔と電子が再結合することにより発光する最小単位をいう。 The organic EL device according to one embodiment of the present invention may be a fluorescent or phosphorescent monochromatic light emitting device, a fluorescent/phosphorescent hybrid white light emitting device, or a simple type having a single light emitting unit. However, it may be of a tandem type having a plurality of light-emitting units, and among these, it is preferably a fluorescent light-emitting device. Here, the term “light-emitting unit” refers to a minimum unit that includes organic layers, at least one layer of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.
　例えば、シンプル型有機ＥＬ素子の代表的な素子構成としては、以下の素子構成を挙げることができる。
（１）陽極／発光ユニット／陰極
　また、上記発光ユニットは、燐光発光層や蛍光発光層を複数有する多層型であってもよく、その場合、各発光層の間に、燐光発光層で生成された励起子が蛍光発光層に拡散することを防ぐ目的で、スペース層を有していてもよい。シンプル型発光ユニットの代表的な層構成を以下に示す。括弧内の層は任意である。
（ａ）（正孔注入層／）正孔輸送層／蛍光発光層／電子輸送層（／電子注入層）
（ｂ）（正孔注入層／）正孔輸送層／第１蛍光発光層／第２蛍光発光層／電子輸送層（／電子注入層）
（ｃ）（正孔注入層／）正孔輸送層／燐光発光層／スペース層／蛍光発光層／電子輸送層（／電子注入層）
（ｄ）（正孔注入層／）正孔輸送層／第１燐光発光層／第２燐光発光層／スペース層／蛍光発光層／電子輸送層（／電子注入層）
（ｅ）（正孔注入層／）正孔輸送層／燐光発光層／スペース層／第１蛍光発光層／第２蛍光発光層／電子輸送層（／電子注入層）
（ｆ）（正孔注入層／）正孔輸送層／電子阻止層／蛍光発光層／電子輸送層（／電子注入層）
（ｇ）（正孔注入層／）正孔輸送層／励起子阻止層／蛍光発光層／電子輸送層（／電子注入層）
（ｈ）（正孔注入層／）第１正孔輸送層／第２正孔輸送層／蛍光発光層／電子輸送層（／電子注入層）
（ｉ）（正孔注入層／）第１正孔輸送層／第２正孔輸送層／蛍光発光層／第１電子輸送層／第２電子輸送層（／電子注入層）
（ｊ）（正孔注入層／）正孔輸送層／蛍光発光層／正孔阻止層／電子輸送層（／電子注入層）
（ｋ）（正孔注入層／）正孔輸送層／蛍光発光層／励起子阻止層／電子輸送層（／電子注入層） For example, as a representative device configuration of the simple type organic EL device, the following device configuration can be mentioned.
(1) Anode/light-emitting unit/cathode The light-emitting unit may be of a multilayer type having a plurality of phosphorescent-emitting layers or fluorescent-emitting layers. A space layer may be provided for the purpose of preventing the excitons from diffusing into the fluorescence-emitting layer. A typical layer structure of a simple light-emitting unit is shown below. Layers in brackets are optional.
(a) (Hole Injection Layer/) Hole Transport Layer/Fluorescent Emitting Layer/Electron Transport Layer (/Electron Injection Layer)
(b) (Hole Injection Layer/) Hole Transport Layer/First Fluorescent Layer/Second Fluorescent Layer/Electron Transport Layer (/Electron Injection Layer)
(c) (Hole injection layer/) Hole transport layer/Phosphorescent layer/Space layer/Fluorescent layer/Electron transport layer (/Electron injection layer)
(d) (hole injection layer/) hole transport layer/first phosphorescence-emitting layer/second phosphorescence-emitting layer/space layer/fluorescence-emitting layer/electron transport layer (/electron injection layer)
(e) (Hole Injection Layer/) Hole Transport Layer/Phosphorescent Layer/Space Layer/First Fluorescent Layer/Second Fluorescent Layer/Electron Transport Layer (/Electron Injection Layer)
(f) (Hole Injection Layer/) Hole Transport Layer/Electron Blocking Layer/Fluorescent Emitting Layer/Electron Transport Layer (/Electron Injection Layer)
(g) (Hole Injection Layer/) Hole Transport Layer/Exciton Blocking Layer/Fluorescent Emitting Layer/Electron Transport Layer (/Electron Injection Layer)
(h) (Hole Injection Layer/) First Hole Transport Layer/Second Hole Transport Layer/Fluorescent Emitting Layer/Electron Transport Layer (/Electron Injection Layer)
(i) (Hole Injection Layer/) First Hole Transport Layer/Second Hole Transport Layer/Fluorescence Emitting Layer/First Electron Transport Layer/Second Electron Transport Layer (/Electron Injection Layer)
(j) (hole-injection layer/) hole-transport layer/fluorescence-emitting layer/hole-blocking layer/electron-transport layer (/electron-injection layer)
(k) (Hole Injection Layer/) Hole Transport Layer/Fluorescence Emitting Layer/Exciton Blocking Layer/Electron Transport Layer (/Electron Injection Layer)
　上記各燐光又は蛍光発光層は、それぞれ互いに異なる発光色を示すものとすることができる。具体的には、上記発光ユニット（ｆ）において、（正孔注入層／）正孔輸送層／第１燐光発光層（赤色発光）／第２燐光発光層（緑色発光）／スペース層／蛍光発光層（青色発光）／電子輸送層といった層構成等が挙げられる。
　なお、各発光層と正孔輸送層あるいはスペース層との間には、適宜、電子阻止層を設けてもよい。また、各発光層と電子輸送層との間には、適宜、正孔阻止層を設けてもよい。電子阻止層や正孔阻止層を設けることで、電子又は正孔を発光層内に閉じ込めて、発光層における電荷の再結合確率を高め、発光効率を向上させることができる。 Each of the phosphorescent or fluorescent light-emitting layers may exhibit different emission colors. Specifically, in the light-emitting unit (f), (hole injection layer/) hole transport layer/first phosphorescent-emitting layer (red emission)/second phosphorescent-emitting layer (green emission)/space layer/fluorescence emission Examples thereof include a layer structure such as layer (blue light emitting)/electron transport layer.
An electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or space layer. A hole-blocking layer may be appropriately provided between each light-emitting layer and the electron-transporting layer. By providing an electron-blocking layer or a hole-blocking layer, electrons or holes can be confined in the light-emitting layer, the probability of charge recombination in the light-emitting layer can be increased, and the light-emitting efficiency can be improved.
　タンデム型有機ＥＬ素子の代表的な素子構成としては、以下の素子構成を挙げることができる。
（２）陽極／第１発光ユニット／中間層／第２発光ユニット／陰極
　ここで、上記第１発光ユニット及び第２発光ユニットとしては、例えば、それぞれ独立に上述の発光ユニットから選択することができる。
　上記中間層は、一般的に、中間電極、中間導電層、電荷発生層、電子引抜層、接続層、中間絶縁層とも呼ばれ、第１発光ユニットに電子を、第２発光ユニットに正孔を供給する、公知の材料構成を用いることができる。 As a representative device configuration of the tandem-type organic EL device, the following device configuration can be mentioned.
(2) Anode/first light-emitting unit/intermediate layer/second light-emitting unit/cathode Here, the first light-emitting unit and the second light-emitting unit can be independently selected from the light-emitting units described above, for example. .
The intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron withdrawal layer, a connection layer, or an intermediate insulating layer, and provides electrons to the first light-emitting unit and holes to the second light-emitting unit. Known material configurations can be used to supply.
　図１は本発明の一態様に係る有機ＥＬ素子の構成の一例を示す概略図である。有機ＥＬ素子１は、基板２、陽極３、陰極４、及び該陽極３と陰極４との間に配置された発光ユニット１０を有する。発光ユニット１０は、発光層５を有する。発光層５と陽極３との間に正孔輸送帯域６（正孔注入層、正孔輸送層等）、発光層５と陰極４との間に電子輸送帯域７（電子注入層、電子輸送層等）を有する。また、発光層５の陽極３側に電子阻止層（図示せず）を、発光層５の陰極４側に正孔阻止層（図示せず）を、それぞれ設けてもよい。これにより、電子や正孔を発光層５に閉じ込めて、発光層５における励起子の生成効率をさらに高めることができる。 FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL element according to one aspect of the present invention. The organic EL element 1 has a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 10 arranged between the anode 3 and the cathode 4 . The light-emitting unit 10 has a light-emitting layer 5 . A hole transport zone 6 (a hole injection layer, a hole transport layer, etc.) is provided between the light emitting layer 5 and the anode 3, and an electron transport zone 7 (an electron injection layer, an electron transport layer, etc.) is provided between the light emitting layer 5 and the cathode 4. etc.). Further, an electron blocking layer (not shown) and a hole blocking layer (not shown) may be provided on the anode 3 side of the light emitting layer 5 and the cathode 4 side of the light emitting layer 5, respectively. As a result, electrons and holes can be confined in the light-emitting layer 5, and the exciton generation efficiency in the light-emitting layer 5 can be further increased.
　図２は、本発明の一態様に係る有機ＥＬ素子の他の構成を示す概略図である。有機ＥＬ素子１１は、基板２、陽極３、陰極４、及び該陽極３と陰極４との間に配置された発光ユニット２０を有する。発光ユニット２０は、発光層５を有する。陽極３と発光層５の間に配置された正孔輸送帯域は、正孔注入層６ａ、第１正孔輸送層６ｂ及び第２正孔輸送層６ｃから形成されている。また、発光層５と陰極４の間に配置された電子輸送帯域は、第１電子輸送層７ａ及び第２電子輸送層７ｂから形成されている。 FIG. 2 is a schematic diagram showing another configuration of the organic EL element according to one aspect of the present invention. The organic EL element 11 has a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 20 arranged between the anode 3 and the cathode 4 . The light-emitting unit 20 has a light-emitting layer 5 . A hole-transporting zone located between the anode 3 and the light-emitting layer 5 is formed from a hole-injecting layer 6a, a first hole-transporting layer 6b and a second hole-transporting layer 6c. Also, the electron-transporting zone located between the light-emitting layer 5 and the cathode 4 is formed of a first electron-transporting layer 7a and a second electron-transporting layer 7b.
　図３は、本発明の一態様に係る有機ＥＬ素子の他の構成を示す概略図である。有機ＥＬ素子１２は、基板２、陽極３、陰極４、及び該陽極３と陰極４との間に配置された発光ユニット３０を有する。発光ユニット３０は、発光層５を有する。陽極３と発光層５の間に配置された正孔輸送帯域は、正孔注入層６ａ、第１正孔輸送層６ｂ、第２正孔輸送層６ｃ、及び第３正孔輸送層６ｄから形成されている。また、発光層５と陰極４の間に配置された電子輸送帯域は、第１電子輸送層７ａ及び第２電子輸送層７ｂから形成されている。 FIG. 3 is a schematic diagram showing another configuration of the organic EL element according to one aspect of the present invention. The organic EL element 12 has a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 30 arranged between the anode 3 and the cathode 4 . The light-emitting unit 30 has a light-emitting layer 5 . A hole-transporting zone located between the anode 3 and the light-emitting layer 5 is formed from a hole-injecting layer 6a, a first hole-transporting layer 6b, a second hole-transporting layer 6c and a third hole-transporting layer 6d. It is Also, the electron-transporting zone located between the light-emitting layer 5 and the cathode 4 is formed of a first electron-transporting layer 7a and a second electron-transporting layer 7b.
　なお、本発明において、蛍光ドーパント材料（蛍光発光材料）と組み合わされたホストを蛍光ホストと称し、燐光ドーパント材料と組み合わされたホストを燐光ホストと称する。蛍光ホストと燐光ホストは分子構造のみにより区分されるものではない。すなわち、燐光ホストとは、燐光ドーパントを含有する燐光発光層を形成する材料を意味し、蛍光発光層を形成する材料として利用できないことを意味しているわけではない。蛍光ホストについても同様である。 In the present invention, a host combined with a fluorescent dopant material (fluorescent light-emitting material) is called a fluorescent host, and a host combined with a phosphorescent dopant material is called a phosphorescent host. Fluorescent hosts and phosphorescent hosts are not distinguished only by molecular structure. That is, the phosphorescent host means a material that contains a phosphorescent dopant and forms a phosphorescent light-emitting layer, and does not mean that it cannot be used as a material for forming a fluorescent light-emitting layer. The same is true for fluorescent hosts.
基板
　基板は、有機ＥＬ素子の支持体として用いられる。基板としては、例えば、ガラス、石英、プラスチックなどの板を用いることができる。また、可撓性基板を用いてもよい。可撓性基板としては、例えば、ポリカーボネート、ポリアリレート、ポリエーテルスルフォン、ポリプロピレン、ポリエステル、ポリフッ化ビニル、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。また、無機蒸着フィルムを用いることもできる。 Substrate The substrate is used as a support for the organic EL device. As the substrate, for example, a plate of glass, quartz, plastic, or the like can be used. Alternatively, a flexible substrate may be used. Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic deposition films can also be used.
陽極
　基板上に形成される陽極には、仕事関数の大きい（具体的には４．０ｅＶ以上）金属、合金、電気伝導性化合物、およびこれらの混合物などを用いることが好ましい。具体的には、例えば、酸化インジウム－酸化スズ（ＩＴＯ：Ｉｎｄｉｕｍ　Ｔｉｎ　Ｏｘｉｄｅ）、珪素もしくは酸化珪素を含有した酸化インジウム－酸化スズ、酸化インジウム－酸化亜鉛、酸化タングステンおよび酸化亜鉛を含有した酸化インジウム、グラフェン等が挙げられる。この他、金（Ａｕ）、白金（Ｐｔ）、ニッケル（Ｎｉ）、タングステン（Ｗ）、クロム（Ｃｒ）、モリブデン（Ｍｏ）、鉄（Ｆｅ）、コバルト（Ｃｏ）、銅（Ｃｕ）、パラジウム（Ｐｄ）、チタン（Ｔｉ）、または前記金属の窒化物（例えば、窒化チタン）等が挙げられる。 Anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, Graphene etc. are mentioned. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or nitrides of the above metals (for example, titanium nitride).
　これらの材料は、通常、スパッタリング法により成膜される。例えば、酸化インジウム－酸化亜鉛は、酸化インジウムに対し１～１０ｗｔ％の酸化亜鉛を加えたターゲットを、酸化タングステンおよび酸化亜鉛を含有した酸化インジウムは、酸化インジウムに対し酸化タングステンを０．５～５ｗｔ％、酸化亜鉛を０．１～１ｗｔ％含有したターゲットを用いることにより、スパッタリング法で形成することができる。その他、真空蒸着法、塗布法、インクジェット法、スピンコート法などにより作製してもよい。 These materials are usually deposited by a sputtering method. For example, indium oxide-zinc oxide is a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide is a target in which 0.5 to 5 wt% of tungsten oxide is added to indium oxide. %, and 0.1 to 1 wt % of zinc oxide, it can be formed by a sputtering method. In addition, it may be produced by a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method, or the like.
正孔輸送帯域
　上述したように、前記有機層が前記陽極と前記発光層の間に正孔輸送帯域を含んでいてもよい。正孔輸送帯域は、正孔注入層、正孔輸送層、電子阻止層等から構成される。正孔輸送帯域が発明化合物を含むことが好ましい。正孔輸送層を構成するこれらの層のうち少なくとも一つの層に発明化合物を含むことが好ましく、特に正孔輸送層に発明化合物を含むことがより好ましい。 Hole-Transporting Zone As mentioned above, the organic layer may contain a hole-transporting zone between the anode and the light-emitting layer. The hole-transporting zone is composed of a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, and the like. It is preferred that the hole-transporting zone comprises an invention compound. At least one of these layers constituting the hole-transporting layer preferably contains the invention compound, and particularly preferably the hole-transporting layer contains the invention compound.
　陽極に接して形成される正孔注入層は、陽極の仕事関数に関係なく正孔注入が容易である材料を用いて形成されるため、電極材料として一般的に使用される材料（例えば、金属、合金、電気伝導性化合物、およびこれらの混合物、元素周期表の第１族または第２族に属する元素）を用いることができる。
　仕事関数の小さい材料である、元素周期表の第１族または第２族に属する元素、すなわちリチウム（Ｌｉ）やセシウム（Ｃｓ）等のアルカリ金属、およびマグネシウム（Ｍｇ）、カルシウム（Ｃａ）、ストロンチウム（Ｓｒ）等のアルカリ土類金属、およびこれらを含む合金（例えば、ＭｇＡｇ、ＡｌＬｉ）、ユーロピウム（Ｅｕ）、イッテルビウム（Ｙｂ）等の希土類金属およびこれらを含む合金等を用いることもできる。なお、アルカリ金属、アルカリ土類金属、およびこれらを含む合金を用いて陽極を形成する場合には、真空蒸着法やスパッタリング法を用いることができる。さらに、銀ペーストなどを用いる場合には、塗布法やインクジェット法などを用いることができる。 The hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode. , alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Groups 1 and 2 of the Periodic Table of the Elements) can be used.
Elements belonging to group 1 or 2 of the periodic table, which are materials with a small work function, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium Alkaline earth metals such as (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these can also be used. In addition, when forming an anode using an alkali metal, an alkaline-earth metal, and the alloy containing these, a vacuum deposition method and a sputtering method can be used. Furthermore, when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.
正孔注入層
　正孔注入層は、正孔注入性の高い材料（正孔注入性材料）を含む層であり、陽極と発光層の間、又は、存在する場合には、正孔輸送層と陽極の間に形成される。 Hole-Injection Layer The hole-injection layer is a layer containing a material with high hole-injection properties (hole-injection material), and is located between the anode and the light-emitting layer or, if present, with the hole-transport layer. formed between the anodes.
　発明化合物以外の正孔注入性材料としては、モリブデン酸化物、チタン酸化物、バナジウム酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、タンタル酸化物、銀酸化物、タングステン酸化物、マンガン酸化物等を用いることができる。 Hole-injecting materials other than invention compounds include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. material, tungsten oxide, manganese oxide, or the like can be used.
　低分子の有機化合物である４，４’，４’’－トリス（Ｎ，Ｎ－ジフェニルアミノ）トリフェニルアミン（略称：ＴＤＡＴＡ）、４，４’，４’’－トリス［Ｎ－（３－メチルフェニル）－Ｎ－フェニルアミノ］トリフェニルアミン（略称：ＭＴＤＡＴＡ）、４，４’－ビス［Ｎ－（４－ジフェニルアミノフェニル）－Ｎ－フェニルアミノ］ビフェニル（略称：ＤＰＡＢ）、４，４’－ビス（Ｎ－｛４－［Ｎ’－（３－メチルフェニル）－Ｎ’－フェニルアミノ］フェニル｝－Ｎ－フェニルアミノ）ビフェニル（略称：ＤＮＴＰＤ）、１，３，５－トリス［Ｎ－（４－ジフェニルアミノフェニル）－Ｎ－フェニルアミノ］ベンゼン（略称：ＤＰＡ３Ｂ）、３－［Ｎ－（９－フェニルカルバゾール－３－イル）－Ｎ－フェニルアミノ］－９－フェニルカルバゾール（略称：ＰＣｚＰＣＡ１）、３，６－ビス［Ｎ－（９－フェニルカルバゾール－３－イル）－Ｎ－フェニルアミノ］－９－フェニルカルバゾール（略称：ＰＣｚＰＣＡ２）、３－［Ｎ－（１－ナフチル）－Ｎ－（９－フェニルカルバゾール－３－イル）アミノ］－９－フェニルカルバゾール（略称：ＰＣｚＰＣＮ１）等の芳香族アミン化合物等も正孔注入層材料として挙げられる。 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3- methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4 '-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N -(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N Aromatic amine compounds such as -(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) can also be used as hole injection layer materials.
　高分子化合物（オリゴマー、デンドリマー、ポリマー等）を用いることもできる。例えば、ポリ（Ｎ－ビニルカルバゾール）（略称：ＰＶＫ）、ポリ（４－ビニルトリフェニルアミン）（略称：ＰＶＴＰＡ）、ポリ［Ｎ－（４－｛Ｎ’－［４－（４－ジフェニルアミノ）フェニル］フェニル－Ｎ’－フェニルアミノ｝フェニル）メタクリルアミド］（略称：ＰＴＰＤＭＡ）、ポリ［Ｎ，Ｎ’－ビス（４－ブチルフェニル）－Ｎ，Ｎ’－ビス（フェニル）ベンジジン］（略称：Ｐｏｌｙ－ＴＰＤ）などの高分子化合物が挙げられる。また、ポリ（３，４－エチレンジオキシチオフェン）／ポリ（スチレンスルホン酸）（ＰＥＤＯＴ／ＰＳＳ）、ポリアニリン／ポリ（スチレンスルホン酸）（ＰＡｎｉ／ＰＳＳ）等の酸を添加した高分子化合物を用いることもできる。 Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino) phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: polymer compounds such as Poly-TPD). In addition, polymer compounds added with acids such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS) are used. can also
　さらに、下記式（Ｋ）で表されるヘキサアザトリフェニレン（ＨＡＴ）化合物などのアクセプター材料を用いることも好ましい。
Figure JPOXMLDOC01-appb-C000218
 Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).
Figure JPOXMLDOC01-appb-C000218
（上記式中、Ｒ２２１～Ｒ２２６は、それぞれ独立にシアノ基、－ＣＯＮＨ２、カルボキシル基、又は－ＣＯＯＲ２２７（Ｒ２２７は炭素数１～２０のアルキル基又は炭素数３～２０のシクロアルキル基を表す）を表す。また、Ｒ２２１及びＲ２２２、Ｒ２２３及びＲ２２４、及びＲ２２５及びＲ２２６から選ばれる隣接する２つが互いに結合して－ＣＯ－Ｏ－ＣＯ－で示される基を形成してもよい。）
　Ｒ２２７としては、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔ－ブチル基、シクロペンチル基、シクロヘキシル基等が挙げられる。 (In the above formula, R 221 to R 226 are each independently a cyano group, —CONH 2 , a carboxyl group, or —COOR 227 (R 227 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, adjacent two selected from R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 are bonded to each other to form a group represented by —CO—O—CO— may form.)
Examples of R 227 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, cyclohexyl group and the like.
正孔輸送層
　正孔輸送層は、正孔輸送性の高い材料（正孔輸送性材料）を含む層であり、陽極と発光層の間、又は、存在する場合には、正孔注入層と発光層の間に形成される。発明化合物を単独で又は下記の化合物と組み合わせて正孔輸送層に用いてもよい。 Hole-transporting layer The hole-transporting layer is a layer containing a material with high hole-transporting properties (hole-transporting material), and is located between the anode and the light-emitting layer or, if present, with the hole-injecting layer. It is formed between the light emitting layers. Invention compounds may be used in the hole-transporting layer alone or in combination with the following compounds.
　正孔輸送層は、単層構造でもよく、２以上の層を含む多層構造でもよい。例えば、正孔輸送層は第１正孔輸送層（陽極側）と第２正孔輸送層（陰極側）を含む２層構造であってもよい。つまり、上記正孔輸送帯域が陽極側の第１正孔輸送層と陰極側の第２正孔輸送層を含んでいてもよい。また、正孔輸送層は陽極側から順に第１正孔輸送層と第２正孔輸送層と第３正孔輸送層を含む３層構造であってもよい。つまり、第２正孔輸送層と発光層との間に、第３正孔輸送層が配置されていてもよい。
　本発明の一態様において、前記単層構造の正孔輸送層は発光層に隣接していることが好ましく、又、前記多層構造中の最も陰極に近い正孔輸送層、例えば、上記２層構造の第２正孔輸送層や上記３層構造の第３正孔輸送層は発光層に隣接していることが好ましい。本発明の他の態様において、前記単層構造の正孔輸送層と発光層の間に、又は、前記多層構造中の最も発光層に近い正孔輸送層と発光層の間に、後述する電子阻止層などを介在させてもよい。
　本発明に係る有機エレクトロルミネッセンス素子の一態様において、前記第１正孔輸送層及び前記第２正孔輸送層の少なくとも一方が発明化合物を含む。具体的には、前記２層構造の正孔輸送層において、発明化合物は第１正孔輸送層と第２正孔輸送層の一方に含まれていてもよいし、双方に含まれていてもよい。また、他の態様において、上記第１～第３正孔輸送層のうち少なくとも一つが発明化合物を含む。具体的には、上記３層構造の正孔輸送層において、発明化合物は第１～第３正孔輸送層のうち一つのみに含まれていてもよいし、いずれか２つのみに含まれていてもよいし、全てに含まれていてもよい。
　本発明の一態様においては、発明化合物が第２正孔輸送層に含まれるのが好ましく、具体的には、発明化合物が第２正孔輸送層のみに含まれるか、発明化合物が第１正孔輸送層と第２正孔輸送層に含まれるのが好ましい。
　本発明の一態様において、前記第１正孔輸送層と前記第２正孔輸送層の一方又は双方に含まれる発明化合物や、前記第１～第３正孔輸送層のうち少なくとも一つ又は複数に含まれる発明化合物は、製造コストの観点から、軽水素体であることが好ましい。
　前記軽水素体とは、発明化合物中のすべての水素原子が軽水素原子である発明化合物のことである。
　従って、本発明は、前記第１正孔輸送層と前記第２正孔輸送層の一方又は双方や、前記第１～第３正孔輸送層のうち少なくとも一つ又は複数が実質的に軽水素体のみからなる発明化合物を含む有機ＥＬ素子を含む。「実質的に軽水素体のみからなる発明化合物」とは、発明化合物の総量に対する軽水素体の含有割合が、９０モル％以上、好ましくは９５モル％以上、より好ましくは９９モル％以上（それぞれ１００％を含む）であることを意味する。 The hole transport layer may have a single layer structure or a multilayer structure including two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole-transporting zone may include a first hole-transporting layer on the anode side and a second hole-transporting layer on the cathode side. Also, the hole transport layer may have a three-layer structure including a first hole transport layer, a second hole transport layer and a third hole transport layer in order from the anode side. That is, the third hole-transporting layer may be arranged between the second hole-transporting layer and the light-emitting layer.
In one aspect of the present invention, the hole-transporting layer having the single-layer structure is preferably adjacent to the light-emitting layer, and the hole-transporting layer closest to the cathode in the multilayer structure, for example, the two-layer structure It is preferable that the second hole-transporting layer of (1) and the third hole-transporting layer of the three-layer structure are adjacent to the light-emitting layer. In another aspect of the present invention, between the hole-transporting layer and the light-emitting layer in the single-layer structure, or between the hole-transporting layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer, an electron A blocking layer or the like may be interposed.
In one aspect of the organic electroluminescence device according to the present invention, at least one of the first hole transport layer and the second hole transport layer contains the compound of the present invention. Specifically, in the hole-transporting layer having the two-layer structure, the compound of the invention may be contained in either the first hole-transporting layer or the second hole-transporting layer, or may be contained in both. good. In another aspect, at least one of the first to third hole transport layers contains the invention compound. Specifically, in the hole-transporting layer having the three-layer structure, the compound of the present invention may be contained in only one of the first to third hole-transporting layers, or may be contained in only any two of the first to third hole-transporting layers. may be included or may be included in all.
In one aspect of the present invention, the invention compound is preferably contained in the second hole transport layer. Specifically, the invention compound is contained only in the second hole transport layer or the invention compound is contained in the first hole transport layer. It is preferably included in the hole transport layer and the second hole transport layer.
In one aspect of the present invention, the invention compound contained in one or both of the first hole-transport layer and the second hole-transport layer, and at least one or more of the first to third hole-transport layers The compound of the invention contained in is preferably a light hydrogen form from the viewpoint of production cost.
The aforementioned light hydrogen compound means an invention compound in which all hydrogen atoms in the invention compound are hydrogen atoms.
Therefore, in the present invention, one or both of the first hole transport layer and the second hole transport layer, and at least one or more of the first to third hole transport layers are substantially hydrogen-containing It includes an organic EL device containing an invention compound consisting only of a body. The term "invention compound consisting essentially of a light hydrogen body" means that the content of the light hydrogen body in the total amount of the invention compounds is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each including 100%).
　発明化合物以外の正孔輸送層材料としては、例えば、芳香族アミン化合物、カルバゾール誘導体、アントラセン誘導体等を使用することができる。
　芳香族アミン化合物としては、例えば、４，４’－ビス［Ｎ－（１－ナフチル）－Ｎ－フェニルアミノ］ビフェニル（略称：ＮＰＢ）やＮ，Ｎ’－ビス（３－メチルフェニル）－Ｎ，Ｎ’－ジフェニル－［１，１’－ビフェニル］－４，４’－ジアミン（略称：ＴＰＤ）、４－フェニル－４’－（９－フェニルフルオレン－９－イル）トリフェニルアミン（略称：ＢＡＦＬＰ）、４，４’－ビス［Ｎ－（９，９－ジメチルフルオレン－２－イル）－Ｎ－フェニルアミノ］ビフェニル（略称：ＤＦＬＤＰＢｉ）、４，４’，４”－トリス（Ｎ，Ｎ－ジフェニルアミノ）トリフェニルアミン（略称：ＴＤＡＴＡ）、４，４’，４”－トリス［Ｎ－（３－メチルフェニル）－Ｎ－フェニルアミノ］トリフェニルアミン（略称：ＭＴＤＡＴＡ）、及び、４，４’－ビス［Ｎ－（スピロ－９，９’－ビフルオレン－２－イル）－Ｎ―フェニルアミノ］ビフェニル（略称：ＢＳＰＢ）が挙げられる。上記化合物は、１０－６ｃｍ２／Ｖｓ以上の正孔移動度を有する。 As hole transport layer materials other than invention compounds, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives and the like can be used.
Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) and N,N'-bis(3-methylphenyl)-N , N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4-phenyl-4′-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4′,4″-tris(N,N -diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4, 4′-bis[N-(spiro-9,9′-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The compound has a hole mobility of 10 −6 cm 2 /Vs or higher.
　カルバゾール誘導体としては、例えば、４，４’－ジ（９－カルバゾリル）ビフェニル（略称：ＣＢＰ）、９－［４－（９－カルバゾリル）フェニル］－１０－フェニルアントラセン（略称：ＣｚＰＡ）、及び、９－フェニル－３－［４－（１０－フェニル－９－アントリル）フェニル］－９Ｈ－カルバゾール（略称：ＰＣｚＰＡ）が挙げられる。
　アントラセン誘導体としては、例えば、２－ｔ－ブチル－９，１０－ジ（２－ナフチル）アントラセン（略称：ｔ－ＢｕＤＮＡ）、９，１０－ジ（２－ナフチル）アントラセン（略称：ＤＮＡ）、及び、９，１０－ジフェニルアントラセン（略称：ＤＰＡｎｔｈ）が挙げられる。
　ポリ（Ｎ－ビニルカルバゾール）（略称：ＰＶＫ）やポリ（４－ビニルトリフェニルアミン）（略称：ＰＶＴＰＡ）等の高分子化合物を用いることもできる。
　ただし、電子輸送性よりも正孔輸送性の方が高い化合物であれば、上記以外の化合物を用いてもよい。 Examples of carbazole derivatives include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).
Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and , 9,10-diphenylanthracene (abbreviation: DAnth).
Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
However, a compound other than the above may be used as long as the compound has higher hole-transporting property than electron-transporting property.
　本発明に係る有機ＥＬ素子の一態様において、前記第１正孔輸送層が、下記の式（１１）又は式（１２）で表される化合物を含むことが好ましい。
Figure JPOXMLDOC01-appb-C000219
［前記式（１１）及び式（１２）中、
　ＬＡ１、ＬＢ１、ＬＣ１、ＬＡ２、ＬＢ２、ＬＣ２及びＬＤ２は、それぞれ独立に、単結合、置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は置換もしくは無置換の環形成原子数５～５０の２価の複素環基であり、
　ｋは、１、２、３又は４であり、
　ｋが１の場合、ＬＥ２は、置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は置換もしくは無置換の環形成原子数５～５０の２価の複素環基であり、
　ｋが２、３又は４の場合、複数のＬＥ２は、互いに同一であるか、又は異なり、
　ｋが２、３又は４の場合、複数のＬＥ２は、互いに結合して置換もしくは無置換の単環を形成するか、互いに結合して置換もしくは無置換の縮合環を形成するか、又は互いに結合せず、
　前記単環を形成せず、かつ前記縮合環を形成しないＬＥ２は、置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は置換もしくは無置換の環形成原子数５～５０の２価の複素環基であり、
　Ａ１、Ｂ１、Ｃ１、Ａ２、Ｂ２、Ｃ２、及びＤ２は、それぞれ独立に、置換もしくは無置換の環形成炭素数６～５０のアリール基、置換もしくは無置換の環形成原子数５～５０の複素環基、又は－Ｓｉ（Ｒ’９０１）（Ｒ’９０２）（Ｒ’９０３）であり、
　Ｒ’９０１、Ｒ’９０２及びＲ’９０３は、それぞれ独立に、置換もしくは無置換の環形成炭素数６～５０のアリール基であり、
　Ｒ’９０１が複数存在する場合、複数のＲ’９０１は、互いに同一であるか、又は異なり、
　Ｒ’９０２が複数存在する場合、複数のＲ’９０２は、互いに同一であるか、又は異なり、
　Ｒ’９０３が複数存在する場合、複数のＲ’９０３は、互いに同一であるか、又は異なる。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、水素原子、
　置換もしくは無置換の炭素数１～５０のアルキル基、
　置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　置換もしくは無置換の環形成原子数５～５０の複素環基であり、
　Ｒ９０１が複数ある場合、複数のＲ９０１は、互いに同一であるか、又は異なり、
　Ｒ９０２が複数ある場合、複数のＲ９０２は、互いに同一であるか、又は異なり、
　Ｒ９０３が複数ある場合、複数のＲ９０３は、互いに同一であるか、又は異なり、
　Ｒ９０４が複数ある場合、複数のＲ９０４は、互いに同一であるか、又は異なり、
　Ｒ９０５が複数ある場合、複数のＲ９０５は、互いに同一であるか、又は異なり、
　Ｒ９０６が複数ある場合、複数のＲ９０６は、互いに同一であるか、又は異なり、
　Ｒ９０７が複数ある場合、複数のＲ９０７は、互いに同一であるか、又は異なる。］ In one aspect of the organic EL device according to the present invention, the first hole transport layer preferably contains a compound represented by the following formula (11) or (12).
Figure JPOXMLDOC01-appb-C000219
[In the above formulas (11) and (12),
L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted is a divalent heterocyclic group having 5 to 50 ring-forming atoms,
k is 1, 2, 3 or 4;
when k is 1, L E2 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms;
When k is 2, 3 or 4, the plurality of L E2 are the same or different from each other,
When k is 2, 3 or 4, a plurality of L E2 are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or do not combine
L E2 that does not form a single ring and does not form a condensed ring is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted 2 having 5 to 50 ring-forming atoms is a valent heterocyclic group,
A 1 , B 1 , C 1 , A 2 , B 2 , C 2 and D 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted ring-forming a heterocyclic group having 5 to 50 atoms, or -Si(R' 901 ) (R' 902 ) (R' 903 );
R' 901 , R' 902 and R' 903 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
When multiple R' 901 are present, the multiple R' 901 are the same or different from each other,
When there are multiple R' 902 , the multiple R' 902 are the same or different from each other,
When multiple R' 903 are present, the multiple R' 903 are the same or different from each other.
R 901 to R 907 each independently represent a hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
When there is a plurality of R 901 , the plurality of R 901 are the same or different from each other,
When there are multiple R 902 , the multiple R 902 are the same or different from each other,
When there are multiple R 903 , the multiple R 903 are the same or different from each other,
When there are multiple R 904 , the multiple R 904 are the same or different from each other,
When there are multiple R 905 , the multiple R 905 are the same or different from each other,
When there are multiple R 906 , the multiple R 906 are the same or different from each other,
When there is a plurality of R 907 , the plurality of R 907 are the same or different from each other. ]
　なお、前記第１正孔輸送層は、式（１１）及び式（１２）で表される化合物を１種含有していてもよいし、式（１１）及び式（１２）で表される化合物を複数種含有していてもよい。 The first hole transport layer may contain one compound represented by formulas (11) and (12), or the compounds represented by formulas (11) and (12) may contain a plurality of types.
　式（１１）及び式（１２）において、Ａ１、Ｂ１、Ｃ１、Ａ２、Ｂ２、Ｃ２、及びＤ２は、好ましくは、それぞれ独立に、置換もしくは無置換のフェニレン基、置換もしくは無置換のビフェニル基、置換もしくは無置換のターフェニル基、置換もしくは無置換のナフチル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンソフラニル基、置換もしくは無置換のジベンゾチオフェニル基、及び、置換もしくは無置換のカルバゾリル基から選択される。
　また、より好ましくは、式（１１）において、Ａ１、Ｂ１及びＣ１のうち少なくとも一つ、及び、式（１２）において、Ａ２、Ｂ２、Ｃ２及びＤ２のうち少なくとも一つが、置換もしくは無置換のビフェニル基、置換もしくは無置換のターフェニル基、置換もしくは無置換のナフチル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンソフラニル基、又は、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のカルバゾリル基である。 In formulas (11) and (12), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, and substituted or unsubstituted selected from carbazolyl groups;
More preferably, at least one of A1, B1 and C1 in formula (11) and at least one of A2, B2, C2 and D2 in formula (12) are substituted or unsubstituted biphenyl substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted It is a substituted carbazolyl group.
　Ａ１、Ｂ１、Ｃ１、Ａ２、Ｂ２、Ｃ２、及びＤ２がとり得るフルオレニル基は、９位に置換基を有していてもよく、例えば、９，９－ジメチルフルオレニル基、９，９－ジフェニルフルオレニル基であってもよい。また、９位の置換基同士で環を形成していてもよく、例えば、９位の置換基同士でフルオレン骨格やキサンテン骨格を形成してもよい。 The fluorenyl group that A1, B1, C1, A2, B2, C2, and D2 can take may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group, a 9,9- It may be a diphenylfluorenyl group. Further, the substituents at the 9-position may form a ring together, for example, the substituents at the 9-position may form a fluorene skeleton or a xanthene skeleton.
　ＬＡ１、ＬＢ１、ＬＣ１、ＬＡ２、ＬＢ２、ＬＣ２及びＬＤ２は、好ましくは、それぞれ独立に、単結合、置換もしくは無置換の環形成炭素数６～１２のアリーレン基である。 L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms.
　式（１１）及び式（１２）で表される化合物の具体例としては、例えば、以下の化合物が挙げられる。
Figure JPOXMLDOC01-appb-C000220
 Specific examples of the compounds represented by formulas (11) and (12) include the following compounds.
Figure JPOXMLDOC01-appb-C000220
発光層のドーパント材料
　発光層は、発光性の高い材料（ドーパント材料）を含む層であり、種々の材料を用いることができる。例えば、蛍光発光材料や燐光発光材料をドーパント材料として用いることができる。蛍光発光材料は一重項励起状態から発光する化合物であり、燐光発光材料は三重項励起状態から発光する化合物である。
　本発明に係る有機ＥＬ素子の一態様において、発光層は単一の層である。
　また、本発明に係る有機ＥＬ素子の他の一態様において、発光層は第１の発光層と第２の発光層とを含む。 Dopant Material of Light-Emitting Layer The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, a fluorescent light-emitting material or a phosphorescent light-emitting material can be used as the dopant material. A fluorescent light-emitting material is a compound that emits light from a singlet excited state, and a phosphorescent light-emitting material is a compound that emits light from a triplet excited state.
In one aspect of the organic EL device according to the present invention, the light-emitting layer is a single layer.
Further, in another aspect of the organic EL device according to the present invention, the light emitting layer includes a first light emitting layer and a second light emitting layer.
　発光層に用いることができる青色系の蛍光発光材料として、ピレン誘導体、スチリルアミン誘導体、クリセン誘導体、フルオランテン誘導体、フルオレン誘導体、ジアミン誘導体、トリアリールアミン誘導体等が使用できる。具体的には、Ｎ，Ｎ’－ビス［４－（９Ｈ－カルバゾール－９－イル）フェニル］－Ｎ，Ｎ’－ジフェニルスチルベン－４，４’－ジアミン（略称：ＹＧＡ２Ｓ）、４－（９Ｈ－カルバゾール－９－イル）－４’－（１０－フェニル－９－アントリル）トリフェニルアミン（略称：ＹＧＡＰＡ）、４－（１０－フェニル－９－アントリル）－４’－（９－フェニル－９Ｈ－カルバゾール－３－イル）トリフェニルアミン（略称：ＰＣＢＡＰＡ）などが挙げられる。 A pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, or the like can be used as a blue fluorescent light-emitting material that can be used in the light-emitting layer. Specifically, N,N′-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4-(9H -carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H -carbazol-3-yl)triphenylamine (abbreviation: PCBAPA) and the like.
　発光層に用いることができる緑色系の蛍光発光材料として、芳香族アミン誘導体等を使用できる。具体的には、Ｎ－（９，１０－ジフェニル－２－アントリル）－Ｎ，９－ジフェニル－９Ｈ－カルバゾール－３－アミン（略称：２ＰＣＡＰＡ）、Ｎ－［９，１０－ビス（１，１’－ビフェニル－２－イル）－２－アントリル］－Ｎ，９－ジフェニル－９Ｈ－カルバゾール－３－アミン（略称：２ＰＣＡＢＰｈＡ）、Ｎ－（９，１０－ジフェニル－２－アントリル）－Ｎ，Ｎ’，Ｎ’－トリフェニル－１，４－フェニレンジアミン（略称：２ＤＰＡＰＡ）、Ｎ－［９，１０－ビス（１，１’－ビフェニル－２－イル）－２－アントリル］－Ｎ，Ｎ’，Ｎ’－トリフェニル－１，４－フェニレンジアミン（略称：２ＤＰＡＢＰｈＡ）、Ｎ－［９，１０－ビス（１，１’－ビフェニル－２－イル）］－Ｎ－［４－（９Ｈ－カルバゾール－９－イル）フェニル］－Ｎ－フェニルアントラセン－２－アミン（略称：２ＹＧＡＢＰｈＡ）、Ｎ，Ｎ，９－トリフェニルアントラセン－９－アミン（略称：ＤＰｈＡＰｈＡ）などが挙げられる。 An aromatic amine derivative or the like can be used as a greenish fluorescent light-emitting material that can be used in the light-emitting layer. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1 '-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N ',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N' , N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1′-biphenyl-2-yl)]-N-[4-(9H-carbazole -9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.
　発光層に用いることができる赤色系の蛍光発光材料として、テトラセン誘導体、ジアミン誘導体等が使用できる。具体的には、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラキス（４－メチルフェニル）テトラセン－５，１１－ジアミン（略称：ｐ－ｍＰｈＴＤ）、７，１４－ジフェニル－Ｎ，Ｎ，Ｎ’，Ｎ’－テトラキス（４－メチルフェニル）アセナフト［１，２－ａ］フルオランテン－３，１０－ジアミン（略称：ｐ－ｍＰｈＡＦＤ）などが挙げられる。 A tetracene derivative, a diamine derivative, or the like can be used as a red fluorescent light-emitting material that can be used in the light-emitting layer. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N', and N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).
　本発明の一態様において、発光層が蛍光発光材料（蛍光ドーパント材料）を含むことが好ましい。 In one aspect of the present invention, the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).
　発光層に用いることができる青色系の燐光発光材料として、イリジウム錯体、オスミウム錯体、白金錯体等の金属錯体が使用される。具体的には、ビス［２－（４’，６’－ジフルオロフェニル）ピリジナト－Ｎ，Ｃ２’］イリジウム（ＩＩＩ）テトラキス（１－ピラゾリル）ボラート（略称：ＦＩｒ６）、ビス［２－（４’，６’－ジフルオロフェニル）ピリジナト－Ｎ，Ｃ２’］イリジウム（ＩＩＩ）ピコリナート（略称：ＦＩｒｐｉｃ）、ビス［２－（３’，５’ビストリフルオロメチルフェニル）ピリジナト－Ｎ，Ｃ２’］イリジウム（ＩＩＩ）ピコリナート（略称：Ｉｒ（ＣＦ３ｐｐｙ）２（ｐｉｃ））、ビス［２－（４’，６’－ジフルオロフェニル）ピリジナト－Ｎ，Ｃ２’］イリジウム（ＩＩＩ）アセチルアセトナート（略称：ＦＩｒａｃａｃ）などが挙げられる。 Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer. Specifically, bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4′ ,6′-difluorophenyl)pyridinato-N,C2′]iridium (III) picolinate (abbreviation: FIrpic), bis[2-(3′,5′bistrifluoromethylphenyl)pyridinato-N,C2′]iridium (III ) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III) acetylacetonate (abbreviation: FIracac), etc. mentioned.
　発光層に用いることができる緑色系の燐光発光材料として、イリジウム錯体等が使用される。トリス（２－フェニルピリジナト－Ｎ，Ｃ２’）イリジウム（ＩＩＩ）（略称：Ｉｒ（ｐｐｙ）３）、ビス（２－フェニルピリジナト－Ｎ，Ｃ２’）イリジウム（ＩＩＩ）アセチルアセトナート（略称：Ｉｒ（ｐｐｙ）２（ａｃａｃ））、ビス（１，２－ジフェニル－１Ｈ－ベンゾイミダゾラト）イリジウム（ＩＩＩ）アセチルアセトナート（略称：Ｉｒ（ｐｂｉ）２（ａｃａｃ））、ビス（ベンゾ［ｈ］キノリナト）イリジウム（ＩＩＩ）アセチルアセトナート（略称：Ｉｒ（ｂｚｑ）２（ａｃａｃ））などが挙げられる。 An iridium complex or the like is used as a greenish phosphorescent material that can be used in the light-emitting layer. Tris (2-phenylpyridinato-N, C2') iridium (III) (abbreviation: Ir (ppy) 3), bis (2-phenylpyridinato-N, C2') iridium (III) acetylacetonate ( Abbreviations: Ir (ppy) 2 (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) 2 (acac)), bis (benzo[ h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)) and the like.
　発光層に用いることができる赤色系の燐光発光材料として、イリジウム錯体、白金錯体、テルビウム錯体、ユーロピウム錯体等の金属錯体が使用される。具体的には、ビス［２－（２’－ベンゾ［４，５－α］チエニル）ピリジナト－Ｎ，Ｃ３’］イリジウム（ＩＩＩ）アセチルアセトナート（略称：Ｉｒ（ｂｔｐ）２（ａｃａｃ））、ビス（１－フェニルイソキノリナト－Ｎ，Ｃ２’）イリジウム（ＩＩＩ）アセチルアセトナート（略称：Ｉｒ（ｐｉｑ）２（ａｃａｃ））、（アセチルアセトナート）ビス［２，３－ビス（４－フルオロフェニル）キノキサリナト］イリジウム（ＩＩＩ）（略称：Ｉｒ（Ｆｄｐｑ）２（ａｃａｃ））、２，３，７，８，１２，１３，１７，１８－オクタエチル－２１Ｈ，２３Ｈ－ポルフィリン白金（ＩＩ）（略称：ＰｔＯＥＰ）等の有機金属錯体が挙げられる。 Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the light-emitting layer. Specifically, bis[2-(2′-benzo[4,5-α]thienyl)pyridinato-N,C3′]iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), Bis(1-phenylisoquinolinato-N,C2′)iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluoro Phenyl)quinoxalinato]iridium (III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum (II) (abbreviation: : PtOEP) and other organometallic complexes.
　また、トリス（アセチルアセトナート）（モノフェナントロリン）テルビウム（ＩＩＩ）（略称：Ｔｂ（ａｃａｃ）３（Ｐｈｅｎ））、トリス（１，３－ジフェニル－１，３－プロパンジオナト）（モノフェナントロリン）ユーロピウム（ＩＩＩ）（略称：Ｅｕ（ＤＢＭ）３（Ｐｈｅｎ））、トリス［１－（２－テノイル）－３，３，３－トリフルオロアセトナト］（モノフェナントロリン）ユーロピウム（ＩＩＩ）（略称：Ｅｕ（ＴＴＡ）３（Ｐｈｅｎ））等の希土類金属錯体は、希土類金属イオンからの発光（異なる多重度間の電子遷移）であるため、燐光発光材料として用いることができる。 In addition, tris (acetylacetonate) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) 3 (Phen)), tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) (abbreviation: Eu (DBM) 3 (Phen)), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: Eu ( Rare-earth metal complexes such as TTA)3(Phen)) can be used as phosphorescent light-emitting materials because they emit light from rare-earth metal ions (electronic transitions between different multiplicities).
発光層のホスト材料
　発光層は、上述したドーパント材料を他の材料（ホスト材料）に分散させた構成としてもよい。ドーパント材料よりも最低空軌道準位（ＬＵＭＯ準位）が高く、最高占有軌道準位（ＨＯＭＯ準位）が低い材料を用いることが好ましい。 Host Material of Light-Emitting Layer The light-emitting layer may have a structure in which the above-described dopant material is dispersed in another material (host material). It is preferable to use a material whose lowest unoccupied molecular orbital level (LUMO level) is higher than that of the dopant material and whose highest occupied molecular orbital level (HOMO level) is lower.
　ホスト材料としては、例えば
（１）アルミニウム錯体、ベリリウム錯体、又は亜鉛錯体等の金属錯体、
（２）オキサジアゾール誘導体、ベンゾイミダゾール誘導体、又はフェナントロリン誘導体等の複素環化合物、
（３）カルバゾール誘導体、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、又はクリセン誘導体等の縮合芳香族化合物、
（４）トリアリールアミン誘導体又は縮合多環芳香族アミン誘導体等の芳香族アミン化合物が使用される。 Examples of host materials include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes;
(2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives;
(3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives;
(4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.
　例えば、トリス（８－キノリノラト）アルミニウム（ＩＩＩ）（略称：Ａｌｑ）、トリス（４－メチル－８－キノリノラト）アルミニウム（ＩＩＩ）（略称：Ａｌｍｑ３）、ビス（１０－ヒドロキシベンゾ［ｈ］キノリナト）ベリリウム（ＩＩ）（略称：ＢｅＢｑ２）、ビス（２－メチル－８－キノリノラト）（４－フェニルフェノラト）アルミニウム（ＩＩＩ）（略称：ＢＡｌｑ）、ビス（８－キノリノラト）亜鉛（ＩＩ）（略称：Ｚｎｑ）、ビス［２－（２－ベンゾオキサゾリル）フェノラト］亜鉛（ＩＩ）（略称：ＺｎＰＢＯ）、ビス［２－（２－ベンゾチアゾリル）フェノラト］亜鉛（ＩＩ）（略称：ＺｎＢＴＺ）などの金属錯体；
　２－（４－ビフェニリル）－５－（４－ｔｅｒｔ－ブチルフェニル）－１，３，４－オキサジアゾール（略称：ＰＢＤ）、１，３－ビス［５－（ｐ－ｔｅｒｔ－ブチルフェニル）－１，３，４－オキサジアゾール－２－イル］ベンゼン（略称：ＯＸＤ－７）、３－（４－ビフェニリル）－４－フェニル－５－（４－ｔｅｒｔ－ブチルフェニル）－１，２，４－トリアゾール（略称：ＴＡＺ）、２，２’，２’’－（１，３，５－ベンゼントリイル）トリス（１－フェニル－１Ｈ－ベンゾイミダゾール）（略称：ＴＰＢＩ）、バソフェナントロリン（略称：ＢＰｈｅｎ）、バソキュプロイン（略称：ＢＣＰ）などの複素環化合物；
　９－［４－（１０－フェニル－９－アントリル）フェニル］－９Ｈ－カルバゾール（略称：ＣｚＰＡ）、３，６－ジフェニル－９－［４－（１０－フェニル－９－アントリル）フェニル］－９Ｈ－カルバゾール（略称：ＤＰＣｚＰＡ）、９，１０－ビス（３，５－ジフェニルフェニル）アントラセン（略称：ＤＰＰＡ）、９，１０－ジ（２－ナフチル）アントラセン（略称：ＤＮＡ）、２－ｔｅｒｔ－ブチル－９，１０－ジ（２－ナフチル）アントラセン（略称：ｔ－ＢｕＤＮＡ）、９，９’－ビアントリル（略称：ＢＡＮＴ）、９，９’－（スチルベン－３，３’－ジイル）ジフェナントレン（略称：ＤＰＮＳ）、９，９’－（スチルベン－４，４’－ジイル）ジフェナントレン（略称：ＤＰＮＳ２）、３，３’，３’’－（ベンゼン－１，３，５－トリイル）トリピレン（略称：ＴＰＢ３）、９，１０－ジフェニルアントラセン（略称：ＤＰＡｎｔｈ）、６，１２－ジメトキシ－５，１１－ジフェニルクリセンなどの縮合芳香族化合物；及び
　Ｎ，Ｎ－ジフェニル－９－［４－（１０－フェニル－９－アントリル）フェニル］－９Ｈ－カルバゾール－３－アミン（略称：ＣｚＡ１ＰＡ）、４－（１０－フェニル－９－アントリル）トリフェニルアミン（略称：ＤＰｈＰＡ）、Ｎ，９－ジフェニル－Ｎ－［４－（１０－フェニル－９－アントリル）フェニル］－９Ｈ－カルバゾール－３－アミン（略称：ＰＣＡＰＡ）、Ｎ，９－ジフェニル－Ｎ－｛４－［４－（１０－フェニル－９－アントリル）フェニル］フェニル｝－９Ｈ－カルバゾール－３－アミン（略称：ＰＣＡＰＢＡ）、Ｎ－（９，１０－ジフェニル－２－アントリル）－Ｎ，９－ジフェニル－９Ｈ－カルバゾール－３－アミン（略称：２ＰＣＡＰＡ）、４，４’－ビス［Ｎ－（１－ナフチル）－Ｎ－フェニルアミノ］ビフェニル（略称：ＮＰＢまたはα－ＮＰＤ）、Ｎ，Ｎ’－ビス（３－メチルフェニル）－Ｎ，Ｎ’－ジフェニル－［１，１’－ビフェニル］－４，４’－ジアミン（略称：ＴＰＤ）、４，４’－ビス［Ｎ－（９，９－ジメチルフルオレン－２－イル）－Ｎ－フェニルアミノ］ビフェニル（略称：ＤＦＬＤＰＢｉ）、４，４’－ビス［Ｎ－（スピロ－９，９’－ビフルオレン－２－イル）－Ｎ―フェニルアミノ］ビフェニル（略称：ＢＳＰＢ）などの芳香族アミン化合物を用いることができる。ホスト材料は複数種用いてもよい。 For example, tris(8-quinolinolato)aluminum (III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) (abbreviation: Znq) ), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and other metal complexes ;
2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2 ,4-triazole (abbreviation: TAZ), 2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline ( Heterocyclic compounds such as abbreviation: BPhen) and bathocuproine (abbreviation: BCP);
9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H -carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl -9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9′-bianthryl (abbreviation: BANT), 9,9′-(stilbene-3,3′-diyl)diphenanthrene ( DPNS), 9,9′-(stilbene-4,4′-diyl)diphenanthrene (abbreviation: DPNS2), 3,3′,3″-(benzene-1,3,5-triyl)tripylene ( abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), condensed aromatic compounds such as 6,12-dimethoxy-5,11-diphenylchrysene; and N,N-diphenyl-9-[4-(10 -Phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N -[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9- anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N′-bis(3-methylphenyl)-N,N '-Diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenyl Aromatic amine compounds such as amino]biphenyl (abbreviation: DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. A plurality of host materials may be used.
　特に、青色蛍光素子の場合には、下記のアントラセン化合物をホスト材料として用いることが好ましい。 Especially in the case of a blue fluorescent device, it is preferable to use the following anthracene compound as a host material.
Figure JPOXMLDOC01-appb-C000221
Figure JPOXMLDOC01-appb-C000221
Figure JPOXMLDOC01-appb-C000222
Figure JPOXMLDOC01-appb-C000222
Figure JPOXMLDOC01-appb-C000223
Figure JPOXMLDOC01-appb-C000223
　本発明に係る有機ＥＬ素子の一態様において、発光層が第１の発光層と第２の発光層とを含む場合、第１の発光層を構成する成分の少なくとも一つが第２の発光層を構成する成分とは異なる。例えば、第１の発光層に含まれるドーパント材料が第２の発光層に含まれるドーパント材料と異なる態様や、第１の発光層に含まれるホスト材料が第２の発光層に含まれるホスト材料と異なる態様が挙げられる。 In one aspect of the organic EL device according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer includes the second light-emitting layer. It is different from the constituent ingredients. For example, the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, and the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer. Different aspects are included.
　本実施形態に係る有機ＥＬ素子において、発光層は、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物を含有していてもよい。 In the organic EL device according to this embodiment, the light-emitting layer may contain a light-emitting compound that emits fluorescent light with a main peak wavelength of 500 nm or less.
　化合物の主ピーク波長の測定方法は、次の通りである。測定対象となる化合物の５μｍｏｌ／Ｌトルエン溶液を調製して石英セルに入れ、常温（３００Ｋ）でこの試料の発光スペクトル（縦軸：発光強度、横軸：波長とする。）を測定する。発光スペクトルは、株式会社日立ハイテクサイエンス製の分光蛍光光度計（装置名：Ｆ－７０００）により測定できる。なお、発光スペクトル測定装置は、ここで用いた装置に限定されない。
　発光スペクトルにおいて、発光強度が最大となる発光スペクトルのピーク波長を主ピーク波長とする。なお、本明細書において、主ピーク波長を蛍光発光主ピーク波長（ＦＬ－ｐｅａｋ）と称する場合がある。 A method for measuring the main peak wavelength of a compound is as follows. A 5 μmol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300K). The emission spectrum can be measured with a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd. Note that the emission spectrum measuring device is not limited to the device used here.
In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the main peak wavelength. In this specification, the main peak wavelength may be referred to as fluorescence emission main peak wavelength (FL-peak).
　主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物は、上記ドーパント材料であってもよいし、上記ホスト材料であってもよい。 The luminescent compound that emits fluorescence with a main peak wavelength of 500 nm or less may be the dopant material or the host material.
　発光層が単一の層である場合、ドーパント材料とホスト材料のうち一方のみが主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物であってもよいし、両方の材料の主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物であってもよい。
　また、発光層が第１の発光層と第２の発光層とを含む場合、第１の発光層と第２の発光層のうち一方のみが、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物を含んでいてもよいし、両方の発光層が、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物を含んでいてもよい。そして、第１の発光層が、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物を含む場合、第１の発光層に含まれるドーパント材料とホスト材料のうち一方のみが、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物であってもよいし、両方の材料が、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物であってもよい。また、第２の発光層が、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物を含む場合、第２の発光層に含まれるドーパント材料とホスト材料のうち一方のみが、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物であってもよいし、両方の材料が、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物であってもよい。 When the light-emitting layer is a single layer, only one of the dopant material and the host material may be a light-emitting compound that emits fluorescence with a main peak wavelength of 500 nm or less, or both materials have a main peak wavelength of A light-emitting compound that emits fluorescence at 500 nm or less may also be used.
Further, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, only one of the first light-emitting layer and the second light-emitting layer emits fluorescence having a main peak wavelength of 500 nm or less. Alternatively, both light-emitting layers may contain a light-emitting compound that emits fluorescent light having a main peak wavelength of 500 nm or less. When the first light-emitting layer contains a light-emitting compound that emits fluorescence with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material contained in the first light-emitting layer has a main peak wavelength of It may be a luminescent compound that emits fluorescence at 500 nm or less, or both materials may be luminescent compounds that emit fluorescence with a main peak wavelength of 500 nm or less. Further, when the second light-emitting layer contains a light-emitting compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material contained in the second light-emitting layer has a main peak wavelength of It may be a luminescent compound that emits fluorescence at 500 nm or less, or both materials may be luminescent compounds that emit fluorescence with a main peak wavelength of 500 nm or less.
電子輸送層
　電子輸送層は電子輸送性の高い材料（電子輸送性材料）を含む層であり、発光層と陰極の間、又は、存在する場合は、電子注入層と発光層の間に形成される。
　電子輸送層は、単層構造でもよく、２以上の層を含む多層構造でもよい。例えば、電子輸送層は第１電子輸送層（陽極側）と第２電子輸送層（陰極側）を含む２層構造であってもよい。本発明の一態様において、前記単層構造の電子輸送層は発光層に隣接していることが好ましく、又、前記多層構造中の最も陽極に近い電子輸送層、例えば、上記２層構造の第１電子輸送層、は発光層に隣接していることが好ましい。本発明の他の態様において、前記単層構造の電子輸送層と発光層の間に、又は、前記多層構造中の最も発光層に近い電子輸送層と発光層の間に、後述する正孔阻止層などを介在させてもよい。 Electron-transporting layer The electron-transporting layer is a layer containing a material with high electron-transporting properties (electron-transporting material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron-injecting layer and the light-emitting layer. be.
The electron transport layer may have a single layer structure or a multilayer structure including two or more layers. For example, the electron transport layer may have a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the present invention, the single-layer electron-transporting layer is preferably adjacent to the light-emitting layer, and the electron-transporting layer closest to the anode in the multilayer structure, for example, the second electron-transporting layer of the two-layer structure. 1 The electron-transporting layer is preferably adjacent to the light-emitting layer. In another aspect of the present invention, between the electron-transporting layer and the light-emitting layer in the single-layer structure, or between the electron-transporting layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer, a hole-blocking layer as described below is provided. A layer or the like may be interposed.
　電子輸送層には、例えば、
（１）アルミニウム錯体、ベリリウム錯体、亜鉛錯体等の金属錯体、
（２）イミダゾール誘導体、ベンゾイミダゾール誘導体、アジン誘導体、カルバゾール誘導体、フェナントロリン誘導体等の複素芳香族化合物、
（３）高分子化合物を使用することができる。 For the electron transport layer, for example,
(1) metal complexes such as aluminum complexes, beryllium complexes and zinc complexes;
(2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives;
(3) Polymer compounds can be used.
　金属錯体としては、例えば、トリス（８－キノリノラト）アルミニウム（ＩＩＩ）（略称：Ａｌｑ）、トリス（４－メチル－８－キノリノラト）アルミニウム（略称：Ａｌｍｑ３）、ビス（１０－ヒドロキシベンゾ［ｈ］キノリナト）ベリリウム（略称：ＢｅＢｑ2）、ビス（２－メチル－８－キノリノラト）（４－フェニルフェノラト）アルミニウム（ＩＩＩ）（略称：ＢＡｌｑ）、ビス（８－キノリノラト）亜鉛（ＩＩ）（略称：Ｚｎｑ）、ビス［２－（２－ベンゾオキサゾリル）フェノラト］亜鉛（ＩＩ）（略称：ＺｎＰＢＯ）、ビス［２－（２－ベンゾチアゾリル）フェノラト］亜鉛（ＩＩ）（略称：ＺｎＢＴＺ）が挙げられる。 Examples of metal complexes include tris(8-quinolinolato)aluminum (III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato ) beryllium (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) (abbreviation: Znq ), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).
　複素芳香族化合物としては、例えば、２－（４－ビフェニリル）－５－（４－ｔｅｒｔ－ブチルフェニル）－１，３，４－オキサジアゾール（略称：ＰＢＤ）、１，３－ビス［５－（ｐ-ｔｅｒｔ－ブチルフェニル）－１，３，４－オキサジアゾール－２－イル］ベンゼン（略称：ＯＸＤ－７）、３－（４－ｔｅｒｔ－ブチルフェニル）－４－フェニル－５－（４－ビフェニリル）－１，２，４－トリアゾール（略称：ＴＡＺ）、３－（４－ｔｅｒｔ－ブチルフェニル）－４－（４－エチルフェニル）－５－（４－ビフェニリル）－１，２，４－トリアゾール（略称：ｐ－ＥｔＴＡＺ）、バソフェナントロリン（略称：ＢＰｈｅｎ）、バソキュプロイン（略称：ＢＣＰ）、４，４’－ビス（５－メチルベンゾオキサゾール－２－イル）スチルベン（略称：ＢｚＯｓ）が挙げられる。 Examples of heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5 -(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5- (4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2 ,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) is mentioned.
　高分子化合物としては、例えば、ポリ［（９，９－ジヘキシルフルオレン－２，７－ジイル）－ｃｏ－（ピリジン－３，５－ジイル）］（略称：ＰＦ－Ｐｙ）、ポリ［（９，９－ジオクチルフルオレン－２，７－ジイル）－ｃｏ－（２，２’－ビピリジン－６，６’－ジイル）］（略称：ＰＦ－ＢＰｙ）が挙げられる。 Examples of polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9, 9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).
　上記材料は、１０－６ｃｍ２／Ｖｓ以上の電子移動度を有する材料である。なお、正孔輸送性よりも電子輸送性の高い材料であれば、上記以外の材料を電子輸送層に用いてもよい。 The above material is a material having an electron mobility of 10 −6 cm 2 /Vs or more. Materials other than those described above may be used for the electron transport layer as long as the material has higher electron transport properties than hole transport properties.
電子注入層
　電子注入層は、電子注入性の高い材料を含む層である。電子注入層には、リチウム（Ｌｉ）、セシウム（Ｃｓ）等のアルカリ金属、マグネシウム（Ｍｇ）、カルシウム（Ｃａ）、ストロンチウム（Ｓｒ）等のアルカリ土類金属、ユーロピウム（Ｅｕ）、イッテルビウム（Ｙｂ）等の希土類金属、及びこれらの金属を含む化合物を用いることができる。そのような化合物としては、例えば、アルカリ金属酸化物、アルカリ金属ハロゲン化物、アルカリ金属含有有機錯体、アルカリ土類金属酸化物、アルカリ土類金属ハロゲン化物、アルカリ土類金属含有有機錯体、希土類金属酸化物、希土類金属ハロゲン化物、及び希土類金属含有有機錯体が挙げられる。また、これらの化合物を複数混合して用いることもできる。
　その他、電子輸送性を有する材料にアルカリ金属、アルカリ土類金属、またはそれらの化合物を含有させたもの、具体的にはＡｌｑ中にマグネシウム（Ｍｇ）を含有させたもの等を用いてもよい。なお、この場合には、陰極からの電子注入をより効率良く行うことができる。
　あるいは、電子注入層に、有機化合物と電子供与体（ドナー）とを混合してなる複合材料を用いてもよい。このような複合材料は、有機化合物が電子供与体から電子を受け取るため、電子注入性および電子輸送性に優れている。この場合、有機化合物としては、受け取った電子の輸送に優れた材料であることが好ましく、具体的には、例えば上述した電子輸送層を構成する材料（金属錯体や複素芳香族化合物等）を用いることができる。電子供与体としては、有機化合物に対し電子供与性を示す材料であればよい。具体的には、アルカリ金属、アルカリ土類金属及び希土類金属が好ましく、リチウム、セシウム、マグネシウム、カルシウム、エルビウム、イッテルビウム等が挙げられる。また、アルカリ金属酸化物やアルカリ土類金属酸化物が好ましく、リチウム酸化物、カルシウム酸化物、バリウム酸化物等が挙げられる。また、酸化マグネシウムのようなルイス塩基を用いることもできる。また、テトラチアフルバレン（略称：ＴＴＦ）等の有機化合物を用いることもできる。 Electron Injection Layer The electron injection layer is a layer containing a material with high electron injection properties. The electron injection layer contains alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), europium (Eu) and ytterbium (Yb). Rare earth metals such as and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, and rare earth metal oxides. compounds, rare earth metal halides, and rare earth metal-containing organic complexes. Also, a plurality of these compounds can be mixed and used.
In addition, a material having an electron-transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the received electrons. Specifically, for example, the material (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer described above is used. be able to. As the electron donor, any material can be used as long as it exhibits an electron donating property with respect to the organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium and ytterbium. Further, alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide and barium oxide. Lewis bases such as magnesium oxide can also be used. An organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.
陰極
　陰極には、仕事関数の小さい（具体的には３．８ｅＶ以下）金属、合金、電気伝導性化合物、およびこれらの混合物などを用いることが好ましい。このような陰極材料の具体例としては、元素周期表の第１族または第２族に属する元素、すなわちリチウム（Ｌｉ）やセシウム（Ｃｓ）等のアルカリ金属、およびマグネシウム（Ｍｇ）、カルシウム（Ｃａ）、ストロンチウム（Ｓｒ）等のアルカリ土類金属、およびこれらを含む合金（例えば、ＭｇＡｇ、ＡｌＬｉ）、ユーロピウム（Ｅｕ）、イッテルビウム（Ｙｂ）等の希土類金属およびこれらを含む合金等が挙げられる。
　なお、アルカリ金属、アルカリ土類金属、これらを含む合金を用いて陰極を形成する場合には、真空蒸着法やスパッタリング法を用いることができる。また、銀ペーストなどを用いる場合には、塗布法やインクジェット法などを用いることができる。
　なお、電子注入層を設けることにより、仕事関数の大小に関わらず、Ａｌ、Ａｇ、ＩＴＯ、グラフェン、珪素もしくは酸化珪素を含有した酸化インジウム－酸化スズ等様々な導電性材料を用いて陰極を形成することができる。これらの導電性材料は、スパッタリング法やインクジェット法、スピンコート法等を用いて成膜することができる。 Cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca ), alkaline earth metals such as strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
In addition, when forming a cathode using an alkali metal, an alkaline-earth metal, and the alloy containing these, a vacuum deposition method and a sputtering method can be used. Moreover, when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.
By providing an electron injection layer, a cathode is formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the magnitude of the work function. can do. These conductive materials can be deposited using a sputtering method, an inkjet method, a spin coating method, or the like.
絶縁層
　有機ＥＬ素子は、超薄膜に電界を印加するために、リークやショートによる画素欠陥が生じやすい。これを防止するために、一対の電極間に絶縁性の薄膜層からなる絶縁層を挿入してもよい。
　絶縁層に用いられる材料としては、例えば、酸化アルミニウム、弗化リチウム、酸化リチウム、弗化セシウム、酸化セシウム、酸化マグネシウム、弗化マグネシウム、酸化カルシウム、弗化カルシウム、窒化アルミニウム、酸化チタン、酸化珪素、酸化ゲルマニウム、窒化珪素、窒化ホウ素、酸化モリブデン、酸化ルテニウム、酸化バナジウム等が挙げられる。なお、これらの混合物や積層物を用いてもよい。 Insulating layer Since an electric field is applied to an ultra-thin organic EL element, pixel defects due to leaks and short circuits are likely to occur. In order to prevent this, an insulating layer made of an insulating thin film layer may be inserted between the pair of electrodes.
Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. , germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like. A mixture or laminate of these materials may also be used.
スペース層
　上記スペース層とは、例えば、蛍光発光層と燐光発光層とを積層する場合に、燐光発光層で生成する励起子を蛍光発光層に拡散させない、あるいは、キャリアバランスを調整する目的で、蛍光発光層と燐光発光層との間に設けられる層である。また、スペース層は、複数の燐光発光層の間に設けることもできる。
　スペース層は発光層間に設けられるため、電子輸送性と正孔輸送性を兼ね備える材料であることが好ましい。また、隣接する燐光発光層内の三重項エネルギーの拡散を防ぐため、三重項エネルギーが２．６ｅＶ以上であることが好ましい。スペース層に用いられる材料としては、上述の正孔輸送層に用いられるものと同様のものが挙げられる。 Space layer The space layer is, for example, when a fluorescent-emitting layer and a phosphorescent-emitting layer are laminated, for the purpose of preventing excitons generated in the phosphorescent-emitting layer from diffusing into the fluorescent-emitting layer or adjusting the carrier balance. It is a layer provided between the fluorescent-emitting layer and the phosphorescent-emitting layer. A space layer can also be provided between a plurality of phosphorescent-emitting layers.
Since the space layer is provided between the light-emitting layers, it is preferably made of a material having both electron-transporting properties and hole-transporting properties. Moreover, the triplet energy is preferably 2.6 eV or more in order to prevent diffusion of the triplet energy in the adjacent phosphorescent-emitting layer. Materials used for the space layer include those similar to those used for the above-described hole transport layer.
阻止層
　電子阻止層、正孔阻止層、励起子阻止層などの阻止層を発光層に隣接して設けてもいい。電子阻止層とは発光層から正孔輸送層へ電子が漏れることを防ぐ層であり、正孔阻止層とは発光層から電子輸送層へ正孔が漏れることを防ぐ層である。励起子阻止層は発光層で生成した励起子が周辺の層へ拡散することを防止し、励起子を発光層内に閉じ込める機能を有する。 Blocking Layers Blocking layers such as electron blocking layers, hole blocking layers, exciton blocking layers, etc. may be provided adjacent to the light-emitting layer. The electron-blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole-transporting layer, and the hole-blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron-transporting layer. The exciton-blocking layer has the function of preventing the excitons generated in the light-emitting layer from diffusing to surrounding layers and confining the excitons within the light-emitting layer.
　前記有機ＥＬ素子の各層は従来公知の蒸着法、塗布法等により形成することができる。例えば、真空蒸着法、分子線蒸着法（ＭＢＥ法）などの蒸着法、あるいは、層を形成する化合物の溶液を用いた、ディッピング法、スピンコーティング法、キャスティング法、バーコート法、ロールコート法等の塗布法による公知の方法で形成することができる。 Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like. For example, a vapor deposition method such as a vacuum vapor deposition method or a molecular beam vapor deposition method (MBE method), or a dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like using a solution of a compound forming a layer. can be formed by a known method by the coating method of .
　各層の膜厚は特に制限されないが、一般に膜厚が薄すぎるとピンホール等の欠陥が生じやすく、逆に厚すぎると高い駆動電圧が必要となり効率が悪くなるため、通常５ｎｍ～１０μｍであり、１０ｎｍ～０．２μｍがより好ましい。 The film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur. 10 nm to 0.2 μm is more preferred.
　本発明の有機ＥＬ素子の一態様において、第１正孔輸送層の厚さと第２正孔輸送層の厚さの合計は、３０ｎｍ以上、１５０ｎｍ以下である。この場合、好ましくは、４０ｎｍ以上、１３０ｎｍ以下である。
　また、本発明の有機ＥＬ素子の一態様において、第２正孔輸送層の厚さは２０ｎｍ以上である。好ましくは２５ｎｍ以上であり、より好ましくは３５ｎｍ以上であり、また、好ましくは１００ｎｍ以下である。
　また、本発明の有機ＥＬ素子の一態様において、発光層と隣接する正孔輸送層が２０ｎｍ以上である。好ましくは２５ｎｍ以上であり、より好ましくは３０ｎｍ以上であり、また、好ましくは１００ｎｍ以下である。
　また、本発明の有機ＥＬ素子の一態様において、第１正孔輸送層の膜厚Ｄ１と第２正孔輸送層膜厚Ｄ２は、０．３＜Ｄ２／Ｄ１＜４．０の関係を満たす。好ましくは０．５＜Ｄ２／Ｄ１＜３．５関係を満たし、より好ましくは０．７５＜Ｄ２／Ｄ１＜３．０の関係を満たす。 In one aspect of the organic EL device of the present invention, the total thickness of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less. In this case, it is preferably 40 nm or more and 130 nm or less.
Moreover, in one aspect of the organic EL device of the present invention, the thickness of the second hole transport layer is 20 nm or more. It is preferably 25 nm or more, more preferably 35 nm or more, and preferably 100 nm or less.
In one aspect of the organic EL device of the present invention, the hole-transporting layer adjacent to the light-emitting layer has a thickness of 20 nm or more. It is preferably 25 nm or more, more preferably 30 nm or more, and preferably 100 nm or less.
In one aspect of the organic EL device of the present invention, the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer satisfy the relationship 0.3<D2/D1<4.0. . It preferably satisfies the relationship 0.5<D2/D1<3.5, and more preferably satisfies the relationship 0.75<D2/D1<3.0.
　本発明の有機ＥＬ素子の実施態様としては、例えば、
上記２層構成の正孔輸送層を有する有機ＥＬ素子であって、
・第２正孔輸送層が本発明の化合物を含み、第１正孔輸送層が本発明の化合物を含まない第１の実施態様；
・第１正孔輸送層及び第２正孔輸送層の双方が本発明の化合物を含む第２の実施態様；
・第１正孔輸送層が本発明の化合物を含み、第２正孔輸送層が本発明の化合物を含まない第３の実施態様；
上記３層構成の正孔輸送層を有する有機ＥＬ素子であって、
・第１正孔輸送層が本発明の化合物を含み、第２及び第３正孔輸送層が本発明の化合物を含まない第４の実施態様；
・第２正孔輸送層が本発明の化合物を含み、第１及び第３正孔輸送層が本発明の化合物を含まない第５の実施態様；
・第３正孔輸送層が本発明の化合物を含み、第１及び第２正孔輸送層が本発明の化合物を含まない第６の実施態様；
・第１及び第２正孔輸送層が本発明の化合物を含み、第３正孔輸送層が本発明の化合物を含まない第７の実施態様；
・第1及び第３正孔輸送層が本発明の化合物を含み、第２正孔輸送層が本発明の化合物を含まない第８の実施態様；
・第２及び第３正孔輸送層が本発明の化合物を含み、第１正孔輸送層が本発明の化合物を含まない第１０の実施態様；
・第１～第３正孔輸送層の全てが本発明の化合物を含む第１０の実施態様；などが挙げられる。 Embodiments of the organic EL element of the present invention include, for example,
The organic EL device having the two-layer structure of the hole transport layer,
- a first embodiment, wherein the second hole-transporting layer comprises a compound of the invention and the first hole-transporting layer does not comprise a compound of the invention;
- a second embodiment in which both the first hole-transporting layer and the second hole-transporting layer comprise a compound of the invention;
- a third embodiment, wherein the first hole-transporting layer comprises a compound of the invention and the second hole-transporting layer does not comprise a compound of the invention;
An organic EL device having a hole transport layer having a three-layer structure,
- a fourth embodiment, wherein the first hole-transporting layer comprises a compound of the invention and the second and third hole-transporting layers do not comprise a compound of the invention;
- a fifth embodiment, wherein the second hole-transporting layer comprises a compound of the invention and the first and third hole-transporting layers do not comprise a compound of the invention;
- a sixth embodiment, wherein the third hole-transporting layer comprises a compound of the invention and the first and second hole-transporting layers do not comprise a compound of the invention;
- a seventh embodiment, wherein the first and second hole-transporting layers comprise a compound of the invention and the third hole-transporting layer does not comprise a compound of the invention;
- an eighth embodiment, wherein the first and third hole-transporting layers comprise a compound of the invention and the second hole-transporting layer does not comprise a compound of the invention;
- a tenth embodiment, wherein the second and third hole-transporting layers comprise a compound of the invention and the first hole-transporting layer does not comprise a compound of the invention;
a tenth embodiment in which all of the first to third hole transport layers contain the compound of the present invention;
電子機器
　前記有機ＥＬ素子は、有機ＥＬパネルモジュール等の表示部品、テレビ、携帯電話、パーソナルコンピュータ等の表示装置、及び、照明、車両用灯具の発光装置等の電子機器に使用できる。 Electronic Equipment The organic EL element can be used for display parts such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic equipment such as light-emitting devices for lighting and vehicle lamps.
　以下、実施例を用いて本発明をさらに詳細に説明するが、本発明は以下の実施例に限定されるものではない。 The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.
実施例１及び２の有機ＥＬ素子の製造に用いた発明化合物
Figure JPOXMLDOC01-appb-C000224
 Inventive compounds used in the production of organic EL devices of Examples 1 and 2
Figure JPOXMLDOC01-appb-C000224
比較例１の有機ＥＬ素子の製造に用いた比較化合物
Figure JPOXMLDOC01-appb-C000225
 Comparative compound used in the production of the organic EL device of Comparative Example 1
Figure JPOXMLDOC01-appb-C000225
実施例１及び２、並びに比較例１の有機ＥＬ素子の製造に用いた他の化合物
Figure JPOXMLDOC01-appb-C000226
 Other compounds used in the production of organic EL devices of Examples 1 and 2 and Comparative Example 1
Figure JPOXMLDOC01-appb-C000226
有機ＥＬ素子（Ｉ）の作製
実施例１
　２５ｍｍ×７５ｍｍ×１．１ｍｍのＩＴＯ透明電極（陽極）付きガラス基板（ジオマテック株式会社製）を、イソプロピルアルコール中で５分間超音波洗浄した後、３０分間ＵＶオゾン洗浄した。ＩＴＯの膜厚は、１３０ｎｍとした。
　洗浄後のＩＴＯ透明電極付き前記ガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極が形成されている側の面上に透明電極を覆うようにして化合物ＨＴ-１と化合物ＨＡを共蒸着し、膜厚１０ｎｍの正孔注入層を形成した。化合物ＨＴ-１と化合物ＨＡの質量比（ＨＴ-１：ＨＡ）は９７：３であった。
　次に、正孔注入層上に化合物ＨＴ-１を蒸着し、膜厚７５ｎｍの第１正孔輸送層を形成した。
　次に、この第１正孔輸送層上に化合物1を蒸着し、膜厚１０ｎｍの第２正孔輸送層を形成した。
　次に、この第２正孔輸送層上に、化合物ＢＨ－１（ホスト材料）と化合物ＢＤ－１（ドーパント材料）を共蒸着し、膜厚２０ｎｍの発光層を形成した。化合物ＢＨ－１と化合物ＢＤ－１の質量比（ＢＨ－１：ＢＤ－１）は９９：１であった。
　次に、この発光層の上に、化合物ＥＴ－１を蒸着して膜厚５ｎｍの第１電子輸送層を形成した。
　次に、この第１電子輸送層上に、化合物ＥＴ－２とＬｉｑを共蒸着し、膜厚２５ｎｍの第２電子輸送層を形成した。化合物ＥＴ－２とＬｉｑの質量比（ＥＴ－２：Ｌｉｑ）は５０：５０であった。
　次に、この第２電子輸送層上に、Ｙｂを蒸着して膜厚１ｎｍの電子注入性電極を形成した。
　そして、この電子注入性電極上に金属Ａｌを蒸着して膜厚８０ｎｍの金属陰極を形成した。
　このようにして得られた実施例１の有機ＥＬ素子の層構成を以下に示す。
ITO　(130)/HT-1:HA=97:3　(10)/HT-1　(75)/化合物１　(10)/BH-1:BD-1=99:1　(20)/ET-1　(5)/ET-2:Liq=50:50　(25)/Yb　(1)/Al　(80)
　上記層構成において、括弧内の数字は膜厚（ｎｍ）であり、比は質量比である。 Preparation Example 1 of Organic EL Device (I)
A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was set to 130 nm.
After washing, the glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus. Vapor deposition to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3.
Next, compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 75 nm.
Next, Compound 1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.
Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1.
Next, the compound ET-1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm.
Next, compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 25 nm. The mass ratio of compound ET-2 and Liq (ET-2:Liq) was 50:50.
Next, Yb was deposited on the second electron transport layer to form an electron injecting electrode with a thickness of 1 nm.
Then, metal Al was vapor-deposited on this electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.
The layer structure of the organic EL device of Example 1 thus obtained is shown below.
ITO (130)/HT-1:HA=97:3 (10)/HT-1 (75)/compound 1 (10)/BH-1:BD-1=99:1 (20)/ET-1 ( 5)/ET-2:Liq=50:50(25)/Yb(1)/Al(80)
In the above layer structure, numbers in parentheses are film thicknesses (nm), and ratios are mass ratios.
外部量子効率（ＥＱＥ）の測定
　得られた有機ＥＬ素子を室温下、電流密度１０ｍＡ／ｃｍ２で直流定電流駆動した。輝度計（ミノルタ社製分光輝度放射計ＣＳ－１０００）を用いて輝度を測定し、その結果から外部量子効率（％）を求めた。結果を表１に示す。 Measurement of External Quantum Efficiency (EQE) The obtained organic EL device was driven at room temperature with a constant DC current at a current density of 10 mA/cm 2 . Luminance was measured using a luminance meter (spectroradiometer CS-1000 manufactured by Minolta), and the external quantum efficiency (%) was determined from the results. Table 1 shows the results.
実施例２及び比較例１
　化合物１の代わりに化合物２（実施例２）、及び比較化合物１（比較例１）を用いた以外は、実施例１と同様にして各有機ＥＬ素子を作製し、外部量子効率を測定した。結果を表１に示す。 Example 2 and Comparative Example 1
Each organic EL device was produced in the same manner as in Example 1 except that Compound 2 (Example 2) and Comparative Compound 1 (Comparative Example 1) were used instead of Compound 1, and the external quantum efficiency was measured. Table 1 shows the results.
Figure JPOXMLDOC01-appb-T000227
Figure JPOXMLDOC01-appb-T000227
　表１の結果から明らかなように、本発明の規定を満たしているモノアミン（実施例１及び２の化合物）が、本発明の規定を満たさないモノアミン（比較例１の比較化合物）に比べて、外部量子効率が改善された有機ＥＬ素子を提供する。 As is clear from the results in Table 1, the monoamines (compounds of Examples 1 and 2) that satisfy the requirements of the present invention, compared to the monoamines (comparative compound of Comparative Example 1) that do not satisfy the requirements of the present invention, An organic EL device with improved external quantum efficiency is provided.
実施例３～９の有機ＥＬ素子の製造に用いた発明化合物
Figure JPOXMLDOC01-appb-C000228
 Inventive compounds used in the production of organic EL devices of Examples 3 to 9
Figure JPOXMLDOC01-appb-C000228
比較例２及び３の有機ＥＬ素子の製造に用いた比較化合物
Figure JPOXMLDOC01-appb-C000229
 Comparative compounds used in the production of organic EL devices of Comparative Examples 2 and 3
Figure JPOXMLDOC01-appb-C000229
実施例３～９、並びに比較例２及び３の有機ＥＬ素子の製造に用いた他の化合物
Figure JPOXMLDOC01-appb-C000230
 Other compounds used in the production of the organic EL devices of Examples 3-9 and Comparative Examples 2 and 3
Figure JPOXMLDOC01-appb-C000230
有機ＥＬ素子（ＩＩ）の作製
実施例３
　２５ｍｍ×７５ｍｍ×１．１ｍｍのＩＴＯ透明電極（陽極）付きガラス基板（ジオマテック株式会社製）を、イソプロピルアルコール中で５分間超音波洗浄した後、３０分間ＵＶオゾン洗浄した。ＩＴＯの膜厚は、１３０ｎｍとした。
　洗浄後のＩＴＯ透明電極付き前記ガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極が形成されている側の面上に透明電極を覆うようにして化合物ＨＴ-２と化合物ＨＡを共蒸着し、膜厚１０ｎｍの正孔注入層を形成した。化合物ＨＴ-２と化合物ＨＡの質量比（ＨＴ-２：ＨＡ）は９７：３であった。
　次に、正孔注入層上に化合物ＨＴ-２を蒸着し、膜厚８０ｎｍの第１正孔輸送層を形成した。
　次に、この第１正孔輸送層上に化合物３を蒸着し、膜厚１０ｎｍの第２正孔輸送層を形成した。
　次に、この第２正孔輸送層上に、化合物ＢＨ－２（ホスト材料）と化合物ＢＤ－２（ドーパント材料）を共蒸着し、膜厚２５ｎｍの発光層を形成した。化合物ＢＨ－２と化合物ＢＤ－２の質量比（ＢＨ－２：ＢＤ－２）は９６：４であった。
　次に、この発光層の上に、化合物ＥＴ－３を蒸着して膜厚１０ｎｍの第１電子輸送層を形成した。
　次に、この第１電子輸送層上に、化合物ＥＴ－４を蒸着して膜厚１５ｎｍの第２電子輸送層を形成した。
　次に、この第２電子輸送層上に、ＬｉＦを蒸着して膜厚１ｎｍの電子注入性電極を形成した。
　そして、この電子注入性電極上に金属Ａｌを蒸着して膜厚５０ｎｍの金属陰極を形成した。
　このようにして得られた実施例３の有機ＥＬ素子の層構成を以下に示す。
ITO　(130)/HT-2:HA=97:3　(10)/HT-2　(80)/化合物3　(10)/BH-2:BD-2=96:4　(25)/ET-3　(10)/ET-4　(15)/LiF　(1)/Al　(50)
　上記層構成において、括弧内の数字は膜厚（ｎｍ）であり、比は質量比である。
　また、得られた有機ＥＬ素子の外部量子効率の測定結果を表２に示す。 Preparation Example 3 of Organic EL Device (II)
A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was set to 130 nm.
After washing, the glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus. Vapor deposition to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-2 to compound HA (HT-2:HA) was 97:3.
Next, compound HT-2 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm.
Next, compound 3 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.
Next, compound BH-2 (host material) and compound BD-2 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The mass ratio of compound BH-2 to compound BD-2 (BH-2:BD-2) was 96:4.
Next, the compound ET-3 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer with a thickness of 10 nm.
Next, compound ET-4 was deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm.
Next, LiF was vapor-deposited on the second electron-transporting layer to form an electron-injecting electrode with a film thickness of 1 nm.
Then, metal Al was vapor-deposited on this electron-injecting electrode to form a metal cathode with a film thickness of 50 nm.
The layer structure of the organic EL element of Example 3 thus obtained is shown below.
ITO (130)/HT-2:HA=97:3 (10)/HT-2 (80)/Compound 3 (10)/BH-2:BD-2=96:4 (25)/ET-3 ( 10)/ET-4(15)/LiF(1)/Al(50)
In the above layer structure, numbers in parentheses are film thicknesses (nm), and ratios are mass ratios.
Table 2 shows the measurement results of the external quantum efficiency of the obtained organic EL device.
実施例４～９並びに比較例２及び３
　化合物３の代わりに化合物４～９（実施例４～９）、並びに比較化合物２及び３（比較例２及び３）を用いた以外は、実施例３と同様にして各有機ＥＬ素子を作製し、外部量子効率を測定した。結果を表２に示す。 Examples 4-9 and Comparative Examples 2 and 3
Each organic EL element was produced in the same manner as in Example 3 except that Compounds 4 to 9 (Examples 4 to 9) and Comparative Compounds 2 and 3 (Comparative Examples 2 and 3) were used instead of Compound 3. , measured the external quantum efficiency. Table 2 shows the results.
Figure JPOXMLDOC01-appb-T000231
Figure JPOXMLDOC01-appb-T000231
　表２の結果から明らかなように、本発明の規定を満たしているモノアミン（実施例３～９の化合物）が、本発明の規定を満たさないモノアミン（比較例２及び３の比較化合物）に比べて、外部量子効率が改善された有機ＥＬ素子を提供する。 As is clear from the results in Table 2, the monoamines (compounds of Examples 3 to 9) that satisfy the requirements of the present invention are compared to the monoamines (comparative compounds of Comparative Examples 2 and 3) that do not satisfy the requirements of the present invention. to provide an organic EL device with improved external quantum efficiency.
合成例で合成した発明化合物
Figure JPOXMLDOC01-appb-C000232
 Invention compounds synthesized in Synthesis Examples
Figure JPOXMLDOC01-appb-C000232
中間体合成例１：中間体Ａの合成
Figure JPOXMLDOC01-appb-C000233
 Intermediate Synthesis Example 1: Synthesis of Intermediate A
Figure JPOXMLDOC01-appb-C000233
　アルゴン雰囲気下、３－（１－ナフタレニル）ベンゼンアミン　５．６８ｇ（２５．９ｍｍｏｌ）、１－ヨードナフタレン　６．５８ｇ（２５．９ｍｍｏｌ）、トリス（ジベンジリデンアセトン）ジパラジウム（０）　０．４７４ｇ，（０．５１８ｍｍｏｌ）、２，２’－ビス（ジフェニルホスフィノ）－１，１’－ビナフチル（ＢＩＮＡＰ）　０．６４５ｇ（１．０４ｍｍｏｌ）、ナトリウム－ｔ－ブトキシド　２．７４ｇ（２８．５ｍｍｏｌ）、トルエン　１３０ｍＬの混合物を１００℃にて７時間撹拌した。反応液を室温に冷却したのち、減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、８．９５ｇの白色固体である中間体Ａを得た。収率は８４％であった。 Under an argon atmosphere, 3-(1-naphthalenyl)benzenamine 5.68 g (25.9 mmol), 1-iodonaphthalene 6.58 g (25.9 mmol), tris(dibenzylideneacetone) dipalladium (0) 0.474 g, (0.518 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) 0.645 g (1.04 mmol), sodium-t-butoxide 2.74 g (28.5 mmol), A mixture of 130 mL of toluene was stirred at 100°C for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 8.95 g of Intermediate A as a white solid. Yield was 84%.
中間体合成例２：中間体Ｂの合成
Figure JPOXMLDOC01-appb-C000234
 Intermediate Synthesis Example 2: Synthesis of Intermediate B
Figure JPOXMLDOC01-appb-C000234
　中間体Ａの合成において１－ヨードナフタレンの代わりに１－（４－ブロモフェニル）ナフタレンを用いる他は同様の操作を行い、８．１８ｇの白色固体である中間体Ｂを得た。収率は９７％であった。 A similar operation was performed except that 1-(4-bromophenyl)naphthalene was used instead of 1-iodonaphthalene in the synthesis of Intermediate A to obtain 8.18 g of Intermediate B as a white solid. Yield was 97%.
中間体合成例３：中間体Ｃの合成
Figure JPOXMLDOC01-appb-C000235
 Intermediate Synthesis Example 3: Synthesis of Intermediate C
Figure JPOXMLDOC01-appb-C000235
　アルゴン雰囲気下、中間体Ｃ－１（２．８７ｇ、１０．０ｍｍｏｌ）、４－（１－ナフタレニル）フェニルボロン酸（２．６０ｇ、１０．５ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム（０）（４６２ｍｇ、０．４００ｍｍｏｌ）、２Ｍリン酸カリウム水溶液　１０ｍＬ（２０．０mmol）、１，４－ジオキサン（５０ｍｌ）を混合させ、８０℃で７時間加熱撹拌し放冷後、混合物をろ過しカラムクロマトグラフィーにて精製し３．０５ｇの白色固体を得た。収率は８４％であった。 Intermediate C-1 (2.87 g, 10.0 mmol), 4-(1-naphthalenyl)phenylboronic acid (2.60 g, 10.5 mmol), tetrakis(triphenylphosphine) palladium(0) ( 462 mg, 0.400 mmol), 10 mL (20.0 mmol) of 2M potassium phosphate aqueous solution, and 1,4-dioxane (50 ml) were mixed, heated with stirring at 80°C for 7 hours, allowed to cool, filtered, and subjected to column chromatography. to obtain 3.05 g of a white solid. Yield was 84%.
中間体合成例４：中間体Ｄの合成
Figure JPOXMLDOC01-appb-C000236
 Intermediate Synthesis Example 4: Synthesis of Intermediate D
Figure JPOXMLDOC01-appb-C000236
　中間体Ａの合成において１－ヨードナフタレンの代わりに１－（３－ブロモフェニル）ナフタレンを、３－（１－ナフタレニル）ベンゼンアミンの代わりに４’－（１－ナフタレニル）［１，１’－ビフェニル］－４－アミンを用いる他は同様の操作を行い、１１．７ｇの白色固体である中間体Ｄを得た。収率は９１％であった。 1-(3-bromophenyl)naphthalene in place of 1-iodonaphthalene and 4′-(1-naphthalenyl)[1,1′- in place of 3-(1-naphthalenyl)benzenamine in the synthesis of intermediate A A similar operation was performed except that biphenyl]-4-amine was used to obtain 11.7 g of Intermediate D as a white solid. Yield was 91%.
合成例１：化合物１の合成
Figure JPOXMLDOC01-appb-C000237
 Synthesis Example 1: Synthesis of Compound 1
Figure JPOXMLDOC01-appb-C000237
　アルゴン雰囲気下、中間体Ａ　２．５９ｇ（７．５０ｍｍｏｌ）、１－（４’－クロロ［１，１’－ビフェニル］－４－イル）ナフタレン　２．８３ｇ（９．００ｍｍｏｌ）、トリス（ジベンジリデンアセトン）ジパラジウム（０）　０．１３７ｇ，（０．１５０ｍｍｏｌ）、トリ－ｔｅｒｔ－ブチルホスホニウムテトラフルオロボラート　０．１７４ｇ（０．６００ｍｍｏｌ）、ナトリウム－ｔ－ブトキシド　１．０１ｇ（１０．５ｍｍｏｌ）、キシレン　７５ｍＬの混合物を１１０℃にて７時間撹拌した。反応液を室温に冷却したのち、減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーおよび再結晶にて精製し、２．３５ｇの白色固体を得た。収率は５０％であった。
　得られたものは、マススペクトル分析の結果化合物１であり、分子量６２３．８０に対しｍ／ｅ＝６２４であった。 Under an argon atmosphere, Intermediate A 2.59 g (7.50 mmol), 1-(4′-chloro[1,1′-biphenyl]-4-yl)naphthalene 2.83 g (9.00 mmol), tris(dibenzylidene Acetone)dipalladium (0) 0.137 g (0.150 mmol), tri-tert-butylphosphonium tetrafluoroborate 0.174 g (0.600 mmol), sodium-t-butoxide 1.01 g (10.5 mmol), A mixture of 75 mL of xylene was stirred at 110° C. for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 2.35 g of white solid. Yield was 50%.
The product obtained was compound 1 as a result of mass spectroscopic analysis, and m/e=624 for a molecular weight of 623.80.
合成例２：化合物２の合成
Figure JPOXMLDOC01-appb-C000238
 Synthesis Example 2: Synthesis of Compound 2
Figure JPOXMLDOC01-appb-C000238
　合成例１において中間体Ａの代わりに中間体Ｂを用いる他は同様の操作を行い、白色固体を得た。
　得られたものは、マススペクトル分析の結果化合物２であり、分子量６９９．９０に対しｍ／ｅ＝７００であった。 A white solid was obtained in the same manner as in Synthesis Example 1, except that Intermediate B was used instead of Intermediate A.
The obtained product was compound 2 as a result of mass spectroscopic analysis, and m/e=700 for a molecular weight of 699.90.
合成例３：化合物３の合成
Figure JPOXMLDOC01-appb-C000239
 Synthesis Example 3: Synthesis of Compound 3
Figure JPOXMLDOC01-appb-C000239
　合成例１において中間体Ａの代わりに中間体Ｂを、１－（４’－クロロ［１，１’－ビフェニル］－４－イル）ナフタレンの代わりに１－（４’－クロロ［１，１’－ビフェニル］－３－イル）ナフタレン用いる他は同様の操作を行い、白色固体を得た。
　得られたものは、マススペクトル分析の結果化合物３であり、分子量６９９．９０に対しｍ／ｅ＝７００であった。 Intermediate B in place of Intermediate A in Synthesis Example 1, 1-(4′-chloro[1,1 A white solid was obtained in the same manner except that '-biphenyl]-3-yl)naphthalene was used.
The obtained product was compound 3 as a result of mass spectroscopic analysis, and m/e=700 for a molecular weight of 699.90.
合成例４：化合物４の合成
Figure JPOXMLDOC01-appb-C000240
 Synthesis Example 4: Synthesis of Compound 4
Figure JPOXMLDOC01-appb-C000240
　合成例１において１－（４’－クロロ［１，１’－ビフェニル］－４－イル）ナフタレンの代わりに２－（４’－クロロ［１，１’－ビフェニル］－３－イル）ナフタレンを用いる他は同様の操作を行い、白色固体を得た。
　得られたものは、マススペクトル分析の結果化合物４であり、分子量６２３．８０に対しｍ／ｅ＝６２４であった。 In Synthesis Example 1, 2-(4'-chloro[1,1'-biphenyl]-3-yl)naphthalene was substituted for 1-(4'-chloro[1,1'-biphenyl]-4-yl)naphthalene. A white solid was obtained by performing the same operation except that it was used.
The obtained product was compound 4 as a result of mass spectroscopic analysis, and m/e=624 with a molecular weight of 623.80.
合成例５：化合物５の合成
Figure JPOXMLDOC01-appb-C000241
 Synthesis Example 5: Synthesis of Compound 5
Figure JPOXMLDOC01-appb-C000241
　合成例１において１－（４’－クロロ［１，１’－ビフェニル］－４－イル）ナフタレンの代わりに中間体Ｃを用いる他は同様の操作を行い、白色固体を得た。
　得られたものは、マススペクトル分析の結果化合物５であり、分子量６２７．８２に対しｍ／ｅ＝６２８であった。 A white solid was obtained in the same manner as in Synthesis Example 1 except that Intermediate C was used in place of 1-(4'-chloro[1,1'-biphenyl]-4-yl)naphthalene.
The obtained product was compound 5 as a result of mass spectroscopic analysis, and m/e=628 with a molecular weight of 627.82.
合成例６：化合物６の合成
Figure JPOXMLDOC01-appb-C000242
 Synthesis Example 6: Synthesis of Compound 6
Figure JPOXMLDOC01-appb-C000242
　合成例１において中間体Ａの代わりにＮ－［３－（１－ナフタレニル）フェニル］［１，１’－ビフェニル］－２－アミンを用いる他は同様の操作を行い、白色固体を得た。
　得られたものは、マススペクトル分析の結果化合物６であり、分子量６４９．８４に対しｍ／ｅ＝６５０であった。 A white solid was obtained in the same manner as in Synthesis Example 1 except that N-[3-(1-naphthalenyl)phenyl][1,1′-biphenyl]-2-amine was used instead of Intermediate A.
The obtained product was compound 6 as a result of mass spectroscopic analysis, and m/e=650 with a molecular weight of 649.84.
合成例７：化合物７の合成
Figure JPOXMLDOC01-appb-C000243
 Synthesis Example 7: Synthesis of Compound 7
Figure JPOXMLDOC01-appb-C000243
　合成例１において中間体Ａの代わりにＮ－［３－（２－ナフタレニル）フェニル］［１，１’－ビフェニル］－４－アミンを用いる他は同様の操作を行い、白色固体を得た。
　得られたものは、マススペクトル分析の結果化合物７であり、分子量６４９．８４に対しｍ／ｅ＝６５０であった。 A white solid was obtained in the same manner as in Synthesis Example 1 except that N-[3-(2-naphthalenyl)phenyl][1,1′-biphenyl]-4-amine was used instead of Intermediate A.
The obtained product was compound 7 as a result of mass spectrometry analysis, and m/e=650 for a molecular weight of 649.84.
合成例８：化合物８の合成
Figure JPOXMLDOC01-appb-C000244
 Synthesis Example 8: Synthesis of Compound 8
Figure JPOXMLDOC01-appb-C000244
　合成例１において中間体Ａの代わりにＮ－［３－（１－ナフタレニル）フェニル］［１，１’－ビフェニル］－４－アミンを用いる他は同様の操作を行い、白色固体を得た。
　得られたものは、マススペクトル分析の結果化合物８であり、分子量６４９．８４に対しｍ／ｅ＝６５０であった。 A white solid was obtained in the same manner as in Synthesis Example 1 except that N-[3-(1-naphthalenyl)phenyl][1,1′-biphenyl]-4-amine was used instead of Intermediate A.
The obtained product was compound 8 as a result of mass spectroscopic analysis, and m/e=650 with a molecular weight of 649.84.
合成例９：化合物９の合成
Figure JPOXMLDOC01-appb-C000245
 Synthesis Example 9: Synthesis of Compound 9
Figure JPOXMLDOC01-appb-C000245
　合成例１において中間体Ａの代わりに中間体Ｄを、１－（４’－クロロ［１，１’－ビフェニル］－４－イル）ナフタレンの代わりに２－ブロモ－１，１’：２’，１”－ターフェニルを用いる他は同様の操作を行い、白色固体を得た。
　得られたものは、マススペクトル分析の結果化合物９であり、分子量７２５．９４に対しｍ／ｅ＝７２６であった。 Intermediate D in place of Intermediate A in Synthesis Example 1 and 2-bromo-1,1′:2′ in place of 1-(4′-chloro[1,1′-biphenyl]-4-yl)naphthalene A white solid was obtained by the same procedure except that ,1″-terphenyl was used.
The obtained product was compound 9 as a result of mass spectroscopic analysis, and m/e=726 with a molecular weight of 725.94.
　１、１１、１２　有機ＥＬ素子
　２　基板
　３　陽極
　４　陰極
　５　発光層
　６　正孔輸送帯域（正孔輸送層）
　６ａ　正孔注入層
　６ｂ　第１正孔輸送層
　６ｃ　第２正孔輸送層
　６ｄ　第３正孔輸送層
　７　電子輸送帯域（電子輸送層）
　７ａ　第１電子輸送層
　７ｂ　第２電子輸送層
　１０、２０、３０　発光ユニット Reference Signs List 1, 11, 12 organic EL element 2 substrate 3 anode 4 cathode 5 light emitting layer 6 hole transport zone (hole transport layer)
6a hole injection layer 6b first hole transport layer 6c second hole transport layer 6d third hole transport layer 7 electron transport zone (electron transport layer)
7a first electron transport layer 7b second electron transport layer 10, 20, 30 light emitting unit

Claims (25)

  1. 　下記式（１）で表される化合物。
    Figure JPOXMLDOC01-appb-C000001
    （式（１）中、
    　Ｎ＊は中心窒素原子であり、
    　Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、及びＲ１Ｄ～Ｒ５Ｄは、それぞれ独立して、水素原子、無置換の炭素数１～６のアルキル基、又は無置換の環形成炭素数６～１２のアリール基である。
    　ただし、
    　Ｒ１Ａ～Ｒ５Ａから選ばれる１つは＊ａに結合する単結合であり、
    　Ｒ１Ｂ～Ｒ５Ｂから選ばれる１つは＊ｂに結合する単結合であり、
    　Ｒ１Ｄ～Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、
    　前記単結合ではないＲ１Ａ～Ｒ５Ａから選ばれる隣接する２つ、前記単結合ではないＲ１Ｂ～Ｒ５Ｂから選ばれる隣接する２つ、及び前記単結合ではないＲ１Ｄ～Ｒ５Ｄから選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成せず、
    　ベンゼン環Ａとベンゼン環Ｂは架橋しない。
     
    　ｍは０又は１である。
    　ただし、ｍが０のとき、＊ｄが中心窒素原子Ｎ＊に結合する。
     
    　Ｒ１Ｃ～Ｒ４Ｃ、Ｒ１Ｕ～Ｒ８Ｕ、及びＲ１Ｖ～Ｒ８Ｖは、水素原子である。
    　ただし、
    　Ｒ１Ｕ～Ｒ８Ｕから選ばれる１つは＊ｕに結合する単結合であり、
    　Ｒ１Ｖ～Ｒ８Ｖから選ばれる１つは＊ｖに結合する単結合であり、
    　ベンゼン環Ｂとナフタレン環Ｕ、ベンゼン環Ｃとナフタレン環Ｖは、架橋しない。
     
    　Ａｒは、下記式（１－ａ）～（１－ｅ）のいずれかで表される。
    Figure JPOXMLDOC01-appb-C000002
    （式（１－ａ）中、
    　＊＊は、前記＊ｄへの結合位置を表す。
    　Ｒ１～Ｒ５は、それぞれ独立して、水素原子、無置換の炭素数１～６のアルキル基、又は無置換のフェニル基である。
    　ただし、
    　前記Ｒ１～Ｒ５から選ばれる１つは＊ｅに結合する単結合であり、前記Ｒ１～Ｒ５から選ばれる他の１つは＊ｆに結合する単結合であり、
    　前記単結合ではないＲ１～Ｒ５から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成せず、
    　ｍが１でｎが１でｌが０のとき下記（ｉ）又は（ｉｉ）を満たし、
    　ｍが１でｎが０でｌが１のとき、下記（ｉｉｉ）又は（ｉｖ）を満たす。
    （ｉ）Ｒ３Ｄは＊ｄに結合する単結合であり、Ｒ１、Ｒ２、Ｒ４、及びＲ５から選ばれる１つは＊ｅに結合する単結合である。
    （ｉｉ）Ｒ１Ｄ、Ｒ２Ｄ、Ｒ４Ｄ、Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、Ｒ１～Ｒ５から選ばれる１つは＊ｅに結合する単結合である。
    （ｉｉｉ）Ｒ３Ｄは＊ｄに結合する単結合であり、Ｒ１、Ｒ２、Ｒ４、及びＲ５から選ばれる１つは＊ｆに結合する単結合である。
    （ｉｖ）Ｒ１Ｄ、Ｒ２Ｄ、Ｒ４Ｄ、Ｒ５Ｄから選ばれる１つは＊ｄに結合する単結合であり、Ｒ１～Ｒ５から選ばれる１つは＊ｆに結合する単結合である。
     
    　Ａｒ１１及びＡｒ１２は、下記式（ｉ）で表される基である。
    Figure JPOXMLDOC01-appb-C000003
    （式（ｉ）中、
    　＊＊＊は、結合位置を表す。
    　Ｒ１１～Ｒ１５は、それぞれ独立して、水素原子又は無置換の炭素数１～６のアルキル基である。
    　ただし、
    　Ｒ１１～Ｒ１５から選ばれる隣接する２つ、及びＲ２１～Ｒ２５から選ばれる隣接する２つは、互いに結合して、置換もしくは無置換のベンゼン環を形成してもよい。）
     
    　ｎは０～２の整数であり、ｎが０のとき、（Ａｒ１１）０は水素原子を表わし、
    　ｌは０～２の整数であり、ｌが０のとき、（Ａｒ１２）０は水素原子を表わす。））
     
    Figure JPOXMLDOC01-appb-C000004
    （式（１－ｂ）中、
    　＊＊は、前記＊ｄへの結合位置を表す。
    　Ｒ２１～Ｒ２８は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
    　ただし、
    　前記Ｒ２１～Ｒ２８から選ばれる１つは＊ｇに結合する単結合であり、前記Ｒ２１～Ｒ２８から選ばれる他の１つは＊ｈに結合する単結合であり、前記Ｒ２１～Ｒ２８から選ばれるさらに他の１つは＊ｉに結合する単結合であり、
    　前記単結合ではないＲ２１～Ｒ２８から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。
     
    　Ａｒ１３及びＡｒ１４は、下記式（ｉｉ）で表される基である。
    Figure JPOXMLDOC01-appb-C000005
    （式（ｉｉ）中、
    　＊＊＊は、結合位置を表す。
    　Ｒ３１～Ｒ３５は、水素原子である。）
     
    　ｏは０、又は１であり、ｏが０のとき（Ａｒ１３）０は水素原子を表わし、
    　ｐは０、又は１であり、ｐが０のとき（Ａｒ１４）０は水素原子を表わす。））
     
    Figure JPOXMLDOC01-appb-C000006
    （式（１－ｃ）中、
    　＊＊は、前記＊ｄへの結合位置を表す。
    　Ｒ４１～Ｒ５２は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
    　ただし、
    　前記Ｒ４１～Ｒ５２から選ばれる１つは＊ｊに結合する単結合であり、前記Ｒ４１～Ｒ５２から選ばれる他の１つは＊ｋに結合する単結合であり、前記Ｒ４１～Ｒ５２から選ばれるさらに他の１つは＊ｌに結合する単結合であり、
    　前記単結合ではないＲ４１～Ｒ５２から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。
     
    　Ａｒ１５及びＡｒ１６は、前記式（ｉｉ）で表される基である。
    　ｑは０、又は１であり、ｑが０のとき（Ａｒ１５）０は水素原子を表わし、
    　ｒは０、又は１であり、ｒが０のとき（Ａｒ１６）０は水素原子を表わす。）
     
    Figure JPOXMLDOC01-appb-C000007
    （式（１－ｄ）中、
    　＊＊は、前記＊ｄへの結合位置を表す。
    　Ｒ６１～Ｒ７０は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
    　ただし、
    　前記Ｒ６１～Ｒ７０から選ばれる１つは＊ｍに結合する単結合であり、前記Ｒ６１～Ｒ７０から選ばれる他の１つは＊ｎに結合する単結合であり、前記Ｒ６１～Ｒ７０から選ばれるさらに他の１つは＊ｏに結合する単結合であり、
    　前記単結合ではないＲ６１～Ｒ７０から選ばれる隣接する２つは、互いに結合せず、したがって環構造を形成しない。
     
    　Ａｒ１7及びＡｒ１８は、前記式（ｉｉ）で表される基である。
    　ｓは０、又は１であり、ｓが０のとき（Ａｒ１７）０は水素原子を表わし、
    　ｔは０、又は１であり、ｔが０のとき（Ａｒ１８）０は水素原子を表わす。）
     
    Figure JPOXMLDOC01-appb-C000008
    （式（１－ｅ）中、
    　＊＊は、前記＊ｄへの結合位置を表す。
    　Ｒ８１～Ｒ８８は、それぞれ独立して、水素原子、置換もしくは無置換の炭素数１～６のアルキル基、又は置換もしくは無置換の環形成炭素数６～１２のアリール基である。
    　ＲＡ及びＲＢは、それぞれ独立して、メチル基、又は置換もしくは無置換のフェニル基である。
    　ただし、
    　＊ｐは、前記Ｒ８１～Ｒ８８、ＲＡ及びＲＢから選ばれる１つに結合し、
    　ＲＡ又はＲＢが＊ｐに結合する場合、＊ｐに結合するＲＡ又はＲＢはメチレン基又は置換もしくは無置換のフェニレン基であり、
    　前記Ｒ８１～Ｒ８８から選ばれる１つが＊ｐに結合する場合、＊ｐに結合する前記Ｒ８１～Ｒ８８から選ばれる１つは単結合であり、
    　前記単結合ではないＲ８１～Ｒ８８から選ばれる隣接する２つは、互いに結合して、置換もしくは無置換のベンゼン環を形成してもよく、
    　＊ｐに結合しないＲＡとＲＢが結合して、スピロ環を形成してもよい。））     A compound represented by the following formula (1).
    Figure JPOXMLDOC01-appb-C000001
    (In formula (1),
    N * is the central nitrogen atom,
    R 1A to R 5A , R 1B to R 5B , and R 1D to R 5D are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted 6 to 6 ring carbon atoms. 12 aryl groups.
    however,
    one selected from R 1A to R 5A is a single bond that binds to *a;
    one selected from R 1B to R 5B is a single bond that bonds to *b;
    one selected from R 1D to R 5D is a single bond that bonds to *d;
    Adjacent two selected from R 1A to R 5A which are not single bonds, adjacent two selected from R 1B to R 5B which are not single bonds, and R 1D to R 5D which are not single bonds adjacent two are not bonded to each other and thus do not form a ring structure;
    Benzene ring A and benzene ring B are not crosslinked.

    m is 0 or 1;
    However, when m is 0, *d is bound to the central nitrogen atom N * .

    R 1C to R 4C , R 1U to R 8U and R 1V to R 8V are hydrogen atoms.
    however,
    one selected from R 1U to R 8U is a single bond that binds to *u;
    one selected from R 1V to R 8V is a single bond that binds to *v;
    Benzene ring B and naphthalene ring U and benzene ring C and naphthalene ring V are not crosslinked.

    Ar is represented by any one of the following formulas (1-a) to (1-e).
    Figure JPOXMLDOC01-appb-C000002
    (In formula (1-a),
    ** represents the binding position to the above *d.
    R 1 to R 5 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group.
    however,
    one selected from R 1 to R 5 is a single bond that bonds to *e, and the other one selected from R 1 to R 5 is a single bond that bonds to *f;
    adjacent two selected from R 1 to R 5 which are not single bonds are not bonded to each other and therefore do not form a ring structure;
    When m is 1, n is 1, and l is 0, the following (i) or (ii) is satisfied,
    When m is 1, n is 0, and l is 1, the following (iii) or (iv) is satisfied.
    (i) R 3D is a single bond bonded to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond bonded to *e;
    (ii) one selected from R 1D , R 2D , R 4D and R 5D is a single bond that bonds to *d, and one selected from R 1 to R 5 is a single bond that bonds to *e .
    (iii) R 3D is a single bond that bonds to *d, and one selected from R 1 , R 2 , R 4 and R 5 is a single bond that bonds to *f.
    (iv) one selected from R 1D , R 2D , R 4D and R 5D is a single bond that binds to *d, and one selected from R 1 to R 5 is a single bond that binds to *f .

    Ar 11 and Ar 12 are groups represented by the following formula (i).
    Figure JPOXMLDOC01-appb-C000003
    (In formula (i),
    *** represents the binding position.
    R 11 to R 15 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms.
    however,
    Two adjacent groups selected from R 11 to R 15 and two adjacent groups selected from R 21 to R 25 may combine with each other to form a substituted or unsubstituted benzene ring. )
     
    n is an integer of 0 to 2, and when n is 0, (Ar 11 ) 0 represents a hydrogen atom;
    l is an integer of 0 to 2, and when l is 0, (Ar 12 ) 0 represents a hydrogen atom. ))

    Figure JPOXMLDOC01-appb-C000004
    (In formula (1-b),
    ** represents the binding position to the above *d.
    R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
    however,
    One selected from R 21 to R 28 is a single bond that bonds to *g, the other one selected from R 21 to R 28 is a single bond that bonds to *h, and R 21 to Still another one selected from R 28 is a single bond attached to *i,
    Adjacent two groups selected from R 21 to R 28 which are not single bonds are not bonded to each other and therefore do not form a ring structure.

    Ar 13 and Ar 14 are groups represented by the following formula (ii).
    Figure JPOXMLDOC01-appb-C000005
    (In formula (ii),
    *** represents the binding position.
    R 31 to R 35 are hydrogen atoms. )

    o is 0 or 1, and when o is 0 (Ar 13 ) 0 represents a hydrogen atom;
    p is 0 or 1, and (Ar 14 ) 0 represents a hydrogen atom when p is 0; ))

    Figure JPOXMLDOC01-appb-C000006
    (In formula (1-c),
    ** represents the binding position to the above *d.
    R 41 to R 52 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
    however,
    One selected from R 41 to R 52 is a single bond that bonds to *j, the other one selected from R 41 to R 52 is a single bond that bonds to *k, and R 41 to Further one selected from R 52 is a single bond attached to *l,
    Adjacent two selected from R 41 to R 52 which are not single bonds are not bonded to each other and thus do not form a ring structure.

    Ar 15 and Ar 16 are groups represented by the above formula (ii).
    q is 0 or 1, and when q is 0 (Ar 15 ) 0 represents a hydrogen atom;
    r is 0 or 1, and (Ar 16 ) 0 represents a hydrogen atom when r is 0; )

    Figure JPOXMLDOC01-appb-C000007
    (In formula (1-d),
    ** represents the binding position to the above *d.
    R 61 to R 70 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
    however,
    One selected from R 61 to R 70 is a single bond that bonds to *m, the other one selected from R 61 to R 70 is a single bond that bonds to *n, and R 61 to Still another one selected from R 70 is a single bond attached to *o,
    Adjacent two groups selected from R 61 to R 70 which are not single bonds are not bonded to each other and thus do not form a ring structure.

    Ar 17 and Ar 18 are groups represented by the above formula (ii).
    s is 0 or 1, and when s is 0 (Ar 17 ) 0 represents a hydrogen atom,
    t is 0 or 1, and (Ar 18 ) 0 represents a hydrogen atom when t is 0; )

    Figure JPOXMLDOC01-appb-C000008
    (In formula (1-e),
    ** represents the binding position to the above *d.
    R 81 to R 88 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
    R A and R B are each independently a methyl group or a substituted or unsubstituted phenyl group.
    however,
    * p is bound to one selected from R 81 to R 88 , R A and R B ;
    when R A or R B is attached to *p, R A or R B attached to *p is a methylene group or a substituted or unsubstituted phenylene group;
    when one selected from R 81 to R 88 is bonded to *p, one selected from R 81 to R 88 bonded to *p is a single bond;
    Adjacent two selected from R 81 to R 88 which are not single bonds may be bonded to each other to form a substituted or unsubstituted benzene ring,
    * R A and R B that are not bonded to p may combine to form a spiro ring. ))
  2. 　前記Ｒ１Ｕ、Ｒ４Ｕ、Ｒ５Ｕ、及びＲ８Ｕから選ばれる１つが、＊ｕに結合する単結合である、請求項１に記載の化合物。 2. The compound of claim 1, wherein one selected from R1U , R4U , R5U , and R8U is a single bond attached to *u.
  3. 　前記Ｒ１Ｖ、Ｒ４Ｖ、Ｒ５Ｖ、及びＲ８Ｖから選ばれる１つが、＊ｖに結合する単結合である、請求項１又は２に記載の化合物。 3. The compound according to claim 1 or 2, wherein one selected from R< 1V >, R <4V >, R< 5V > and R <8V > is a single bond attached to *v.
  4. 　下記式（１－１）で表される、請求項１～３のいずれか１項に記載の化合物。
    Figure JPOXMLDOC01-appb-C000009
    （式（１－１）中、
    　Ｎ＊、Ｒ１Ａ～Ｒ５Ａ、Ｒ１Ｂ～Ｒ５Ｂ、Ｒ１Ｃ～Ｒ４Ｃ、Ｒ１Ｄ～Ｒ５Ｄ、Ｒ２Ｕ～Ｒ８Ｕ、Ｒ１Ｖ～Ｒ７Ｖ、Ａｒ、ｍ、＊ａ、＊ｂ、＊ｄ、ベンゼン環Ａ～ベンゼン環Ｄ、ナフタレン環Ｕ、及びナフタレン環Ｖは、式（１）で定義したとおりである。）     The compound according to any one of claims 1 to 3, represented by the following formula (1-1).
    Figure JPOXMLDOC01-appb-C000009
    (In formula (1-1),
    N * , R1A to R5A , R1B to R5B, R1C to R4C, R1D to R5D, R2U to R8U, R1V to R7V , Ar , m , * a , *b, * d, benzene ring A to benzene ring D, naphthalene ring U, and naphthalene ring V are as defined in formula (1). )
  5. 　前記Ｒ３Ａは、＊ａに結合する単結合である、請求項１～４のいずれか１項に記載の化合物。 A compound according to any one of claims 1 to 4, wherein said R 3A is a single bond attached to *a.
  6. 　前記Ｒ３Ｂは、＊ｂに結合する単結合である、請求項１～５のいずれか１項に記載の化合物。 The compound of any one of claims 1-5, wherein said R 3B is a single bond attached to *b.
  7. 　下記式（１－２）で表される、請求項１～６のいずれか１項に記載の化合物。
    Figure JPOXMLDOC01-appb-C000010
    （式（１－２）中、
    　Ｎ＊、Ｒ１Ａ、Ｒ２Ａ、Ｒ４Ａ、Ｒ５Ａ、Ｒ１Ｂ、Ｒ２Ｂ、Ｒ４Ｂ、Ｒ５Ｂ、Ｒ１Ｃ～Ｒ４Ｃ、Ｒ１Ｄ～Ｒ５Ｄ、Ｒ２Ｕ～Ｒ８Ｕ、Ｒ１Ｖ～Ｒ７Ｖ、Ａｒ、ｍ、＊ｄ、ベンゼン環Ａ～ベンゼン環Ｄ、ナフタレン環Ｕ、及びナフタレン環Ｖは、式（１）で定義したとおりである。）     The compound according to any one of claims 1 to 6, represented by the following formula (1-2).
    Figure JPOXMLDOC01-appb-C000010
    (In formula (1-2),
    N * , R 1A , R 2A , R 4A , R 5A , R 1B , R 2B , R 4B , R 5B , R 1C to R 4C , R 1D to R 5D , R 2U to R 8U , R 1V to R 7V , Ar, m, *d, benzene ring A to benzene ring D, naphthalene ring U, and naphthalene ring V are as defined in formula (1). )
  8. 　前記Ａｒは、前記式（１－ａ）、（１－ｂ）又は（１－ｄ）で表される、請求項１～７のいずれか１項に記載の化合物。 The compound according to any one of claims 1 to 7, wherein said Ar is represented by said formula (1-a), (1-b) or (1-d).
  9. 　前記Ａｒは前記式（１－ｂ）で表される場合、ｍは０である、請求項１～８のいずれか１項に記載の化合物。 The compound according to any one of claims 1 to 8, wherein when said Ar is represented by said formula (1-b), m is 0.
  10. 　前記Ａｒは前記式（１－ａ）又は（１－ｄ）で表される場合、ｍは１である、請求項１～８のいずれか１項に記載の化合物。 The compound according to any one of claims 1 to 8, wherein when said Ar is represented by said formula (1-a) or (1-d), m is 1.
  11. 　＊ａに結合する単結合ではないＲ１Ａ～Ｒ５Ａのすべてが水素原子である、請求項１～６に記載の化合物。 The compound according to claims 1 to 6, wherein all of R 1A to R 5A that are not single bonds attached to *a are hydrogen atoms.
  12. 　＊ｂに結合する単結合ではないＲ１Ｂ～Ｒ５Ｂのすべてが水素原子である、請求項１～６に記載の化合物。 The compound according to any one of claims 1 to 6, wherein all of R 1B to R 5B that are not single bonds attached to *b are hydrogen atoms.
  13. 　前記化合物が、少なくとも１個の重水素原子を含む、請求項１～１２のいずれか１項に記載の化合物。 The compound according to any one of claims 1 to 12, wherein the compound contains at least one deuterium atom.
  14. 　請求項１～１３のいずれか１項に記載の化合物を含む、有機エレクトロルミネッセンス素子用材料。 A material for an organic electroluminescence device, containing the compound according to any one of claims 1 to 13.
  15. 　請求項１～１３のいずれかに記載の化合物が正孔輸送層材料である、請求項１４に記載の有機エレクトロルミネッセンス素子用材料。 The material for an organic electroluminescence device according to claim 14, wherein the compound according to any one of claims 1 to 13 is a hole transport layer material.
  16. 　陰極、陽極、及び該陰極と該陽極の間に有機層を有する有機エレクトロルミネッセンス素子であって、該有機層が発光層を含み、該有機層の少なくとも１層が請求項１～１３のいずれか１項に記載の化合物を含む、有機エレクトロルミネッセンス素子。 An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer comprises a light-emitting layer, and at least one of the organic layers is any one of claims 1 to 13. 2. An organic electroluminescence device comprising the compound according to item 1.
  17. 　前記有機層が前記陽極と前記発光層の間に正孔輸送帯域を含み、該正孔輸送帯域が請求項１～１３のいずれか１項に記載の化合物を含む、請求項１６に記載の有機エレクトロルミネッセンス素子。 Organic according to claim 16, wherein the organic layer comprises a hole-transporting zone between the anode and the light-emitting layer, the hole-transporting zone comprising a compound according to any one of claims 1-13. Electroluminescence device.
  18. 　前記正孔輸送帯域が陽極側の第１正孔輸送層と陰極側の第２正孔輸送層を含み、
    　前記第１正孔輸送層及び前記第２正孔輸送層の少なくとも一方が請求項１～１３のいずれか１項に記載の化合物を含む、請求項１７に記載の有機エレクトロルミネッセンス素子。     wherein the hole transport zone comprises a first hole transport layer on the anode side and a second hole transport layer on the cathode side;
    [18] The organic electroluminescence device according to [17], wherein at least one of the first hole transport layer and the second hole transport layer contains the compound according to any one of [1] to [13].
  19. 　前記第２正孔輸送層が請求項１～１３のいずれか１項に記載の化合物を含む、請求項１８に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to claim 18, wherein the second hole transport layer contains the compound according to any one of claims 1 to 13.
  20. 　前記発光層と前記第２正孔輸送層とが直接接している、請求項１８又は１９に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to claim 18 or 19, wherein the light emitting layer and the second hole transport layer are in direct contact.
  21. 　前記第１正孔輸送層の厚さと前記第２正孔輸送層の厚さの合計が、３０ｎｍ以上、１５０ｎｍ以下である、請求項１８～２０のいずれか１項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to any one of claims 18 to 20, wherein the total thickness of said first hole transport layer and said second hole transport layer is 30 nm or more and 150 nm or less.
  22. 　前記発光層が単一の層である、請求項１６～２１のいずれか１項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to any one of claims 16 to 21, wherein the light-emitting layer is a single layer.
  23. 　前記発光層は、主ピーク波長が５００ｎｍ以下の蛍光発光を示す発光性化合物を含有する、請求項１６～２２のいずれか１項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to any one of claims 16 to 22, wherein the light-emitting layer contains a light-emitting compound that emits fluorescence with a main peak wavelength of 500 nm or less.
  24. 　前記発光層が蛍光ドーパント材料を含む、請求項１６～２３のいずれか１項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to any one of claims 16 to 23, wherein the light-emitting layer contains a fluorescent dopant material.
  25. 　請求項１６～２４のいずれか１項に記載の有機エレクトロルミネッセンス素子を含む、電子機器。

          An electronic device comprising the organic electroluminescence device according to any one of claims 16 to 24.
PCT/JP2022/022952 2021-06-25 2022-06-07 Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device WO2022270296A1 (en)

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JP2018188433A (en) * 2017-05-10 2018-11-29 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． Amine compound and organic el device containing the same
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JP2018188433A (en) * 2017-05-10 2018-11-29 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． Amine compound and organic el device containing the same
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