Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Abstract

Provided is a compound represented by a formula (1). In the formula (1), Z1 to Z3 are each a nitrogen atom or C(R31), with at least two of Z1 to Z3 being nitrogen atoms, R1 to R8, R11 to R18, and R21 to R28 form rings or are hydrogen atoms, substituent groups, and the like, but satisfy at least one condition selected from the group consisting of condition (i) (at least one of R1 to R8 is a substituted or unsubstituted phenyl group), condition (ii) (at least one of R11 to R18 is a substituted or unsubstituted phenyl group), and condition (iii) (at least one of R21 to R28 is a substituted or unsubstituted phenyl group). p is 4, and the four Ax moieties form rings or are hydrogen atoms, substituent groups, and the like.

Description

Compound, material for organic electroluminescence device, organic electroluminescence device and electronic device

[0001] The present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device.

[0002] When a voltage is applied to an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The injected holes and electrons then recombine in the light-emitting layer to form excitons. According to the statistical law of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons at a rate of 75%. Fluorescent organic EL devices that utilize light emission from singlet excitons are increasingly being applied to full-color displays such as mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. In order to improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (see, for example, Patent Documents 1 and 2). Examples of the performance of organic EL devices include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0003] U.S. Pat. No. 1,515,483 U.S. Pat. No. 1,547,009

[0004] An object of the present invention is to provide a compound capable of extending the life of an organic electroluminescence device, to provide a material for an organic electroluminescence device containing the compound, to provide an organic electroluminescence device containing the compound, and to provide an electronic device equipped with the organic electroluminescence device.

[0005] According to one aspect of the present invention, there is provided a compound represented by the following formula (1):

[0006]

[0007] (In the formula (1), Z １ , Z ２ , and Z ３ are each independently a nitrogen atom, or C(R３１ ), where Z １ ~Z ３ At least two of R are nitrogen atoms; １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , and R １８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ２１ , R ２２ , R ２３ , R ２４ , R ２５ , R ２６ , R ２７ , and R ２８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３１ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ ), a group represented by —B(OR ９３８ ) (OR ９３９ a group represented by —O—S(═O) ２ (R ９４０ 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, provided that at least one condition selected from the group consisting of the following conditions (i), (ii), and (iii) is satisfied: Condition (i): R １ ~R ８ Condition (ii): At least one of R １１ ~R １８ Condition (iii): At least one of R ２１ ~R ２８At least one of the four Ax's is a substituted or unsubstituted phenyl group. p is 4, and at least one pair of adjacent two or more Ax's are not bonded to each other, and each Ax is independently a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -C(R ９０１Ｂ ) (R ９０２Ｂ ) (R ９０３Ｂ a group represented by —Si(R ９０１Ａ ) (R ９０２Ａ ) (R ９０３Ａ 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, ９０１ ~R ９０７ , R ８０１ ~R ８０２ , and R ９３１ ~R ９４０ are each independently 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１Ａ , R ９０２Ａ , R ９０３Ａ , R ９０１Ｂ , R ９０２Ｂ , and R ９０３Ｂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, R ９３１ If there are multiple R ９３１ are the same or different from each other, R ９３２ If there are multiple R ９３２ are the same or different from each other, R ９３３ If there are multiple R ９３３ are the same or different from each other, R ９３４ If there are multiple R ９３４ are the same or different from each other, R ９３５ If there are multiple R ９３５ are the same or different from each other, R ９３６ If there are multiple R ９３６ are the same or different from each other, R ９３７ If there are multiple R ９３７ are the same or different from each other, R ９３８ If there are multiple R ９３８ are the same or different from each other, R ９３９ If there are multiple R ９３９ are the same or different from each other, R ９４０ If there are multiple R ９４０ are the same or different from each other, R ９０１Ａ If there are multiple R ９０１Ａ are the same or different from each other, R ９０２Ａ If there are multiple R ９０２Ａ are the same or different from each other, R ９０３ＡIf there are multiple R ９０３Ａ are the same or different from each other, R ９０１Ｂ If there are multiple R ９０１Ｂ are the same or different from each other, R ９０２Ｂ If there are multiple R ９０２Ｂ are the same or different from each other, R ９０３Ｂ If there are multiple R ９０３Ｂ are the same or different from each other.)

[0008] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device, which contains a compound according to one aspect of the present invention.

[0009] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising a cathode, an anode, and an emitting unit disposed between the cathode and the anode, wherein the emitting unit contains a compound according to one aspect of the present invention as a first compound.

[0010] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention.

[0011] According to one aspect of the present invention, it is possible to provide a compound that can extend the life of an organic electroluminescence device, to provide a material for an organic electroluminescence device containing the compound, to provide an organic electroluminescence device containing the compound, and to provide an electronic device equipped with the organic electroluminescence device.

[0012] 1 is a schematic diagram of an apparatus for measuring transient PL; FIG. 2 is a diagram showing an example of a decay curve of transient PL; FIG. 3 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention; FIG. 4 is a diagram showing the energy levels and energy transfer relationship of a first host material, a sensitizing material, and a fluorescent material in an emission layer of an example of an organic electroluminescence element according to a fourth embodiment of the present invention; FIG. 5 is a diagram showing the energy levels and energy transfer relationship of a first host material, a sensitizing material, and a fluorescent material in an emission layer of an example of an organic electroluminescence element according to the fourth embodiment of the present invention; FIG. 6 is a diagram showing the energy levels and energy transfer relationship of a first host material, a second host material, a sensitizing material, and a fluorescent material in an emission layer of an example of an organic electroluminescence element according to a fifth embodiment of the present invention; FIG. 7 is a diagram showing the energy levels and energy transfer relationship of a sensitizing material and a fluorescent material in an emission layer of an example of an organic electroluminescence element according to a sixth embodiment of the present invention; and FIG. 8 is a diagram showing the energy levels and energy transfer relationship of a second host material, a sensitizing material, and a fluorescent material in an emission layer of an example of an organic electroluminescence element according to a seventh embodiment of the present invention.

[0013] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0014] In this specification, in a chemical structural formula, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0015] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same 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. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. When a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of a benzene ring substituted with an alkyl group is 6. Furthermore, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0016] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0017] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0018] In this specification, the "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0019] In this specification, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. Furthermore, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0020] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0021] The number of ring carbon atoms of an "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring atoms of an "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring carbon atoms of an "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. Unless otherwise specified herein, the number of ring carbon atoms of an "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18. Unless otherwise specified herein, the number of ring atoms of an "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18. Unless otherwise specified herein, the number of carbon atoms of an "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0022] "Substituted or Unsubstituted Aryl Group" Specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl group" described herein include the following unsubstituted aryl group (Specific Example Group G1A) and substituted aryl group (Specific Example Group G1B). (Here, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents in the "unsubstituted aryl group" of the following Specific Example Group G1A, and examples of the substituted aryl group of the following Specific Example Group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent.

[0023] Unsubstituted aryl groups (specific example group G1A): a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a benzanthryl 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, a pentacenyl group, a fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, perylenyl group, and monovalent aryl groups derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15):

[0024]

[0025]

[0026] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl groups, and monovalent groups derived from the ring structures represented by the above general formulae (TEMP-1) to (TEMP-15), in which one or more hydrogen atoms are replaced with substituents.

[0027] "Substituted or Unsubstituted Heterocyclic Group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described herein is a monocyclic group or a fused ring group. The "heterocyclic group" described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, an unsubstituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and 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 substituents. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of an "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of substituted heterocyclic groups in the following specific example group G2B. The examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification also include groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent.

[0028] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0029] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).

[0030] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): a 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, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.

[0031] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a 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, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0032] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0033] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0034]

[0035]

[0036] In the general formulae (TEMP-16) to (TEMP-33), X Ａ and Y Ａ are each independently an oxygen atom, a sulfur atom, NH, or CH ２ However, X Ａ and Y Ａ At least one of X is an oxygen atom, a sulfur atom, or NH. Ａ and Y Ａ At least one of the groups is NH or CH ２ In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may contain any of these NH, CH ２ and monovalent groups obtained by removing one hydrogen atom from the group consisting of:

[0037] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0038] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0039] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0040] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):

[0041] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X Ａ and Y Ａ a hydrogen atom bonded to a nitrogen atom when at least one of Ａ and Y Ａ One of them is CH ２ and n is 0 or more. The methylene group in the formula (I) is one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the formula (I).

[0042] "Substituted or Unsubstituted Alkyl Group" Specific examples (Specific Example Group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (Specific Example Group G3A) and substituted alkyl group (Specific Example Group G3B). (Here, the term "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the term "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, the term "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with substituents. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (Specific Example Group G3A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in an "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the term "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes groups in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent.

[0043] Unsubstituted alkyl groups (specific example group G3A): a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.

[0044] Substituted alkyl groups (specific example group G3B): a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.

[0045] "Substituted or Unsubstituted Alkenyl Group" Specific examples (Specific Example Group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (Specific Example Group G4A) and substituted alkenyl group (Specific Example Group G4B). (Here, an unsubstituted alkenyl group refers to a case where a "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and a "substituted alkenyl group" refers to a case where a "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply refers to both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with substituents. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent.

[0046] Unsubstituted alkenyl groups (specific example group G4A): a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.

[0047] Substituted alkenyl groups (specific example group G4B): a 1,3-butadienyl group, a 1-methylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, and a 1,2-dimethylallyl group.

[0048] - "Substituted or Unsubstituted Alkynyl Group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, an unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, the term "alkynyl group" includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent.

[0049] Unsubstituted alkynyl groups (specific example group G5A): ethynyl groups.

[0050] "Substituted or Unsubstituted Cycloalkyl Group" Specific examples (Specific Example Group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply refers to both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with substituents. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (Specific Example Group G6A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted cycloalkyl group (Specific Example Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described in this specification also include groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl groups" of specific example group G6B are replaced with substituents, and groups in which a hydrogen atom of a substituent in the "substituted cycloalkyl groups" of specific example group G6B is further replaced with a substituent.

[0051] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.

[0052] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0053] -Si(R ９０１ ) (R ９０２ ) (R ９０３ A group represented by —Si(R ９０１ ) (R ９０２) (R ９０３ Specific examples (specific example group G7) of the group represented by the formula (G1) 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). 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. The multiple G1s in -Si(G1)(G1)(G1) may be the same or different. - Multiple G2 in Si(G1)(G2)(G2) are the same as or different from each other. - Multiple G1 in Si(G1)(G1)(G2) are the same as or different from each other. - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other. - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other. - Multiple G6 in Si(G6)(G6)(G6) are the same as or different from each other.

[0054] ・「-O-(R ９０４ A group represented by —O—(R ９０４ ) (Specific example group G8) includes -O(G1), -O(G2), -O(G3), and -O(G6). 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.

[0055] ・"-S-(R ９０５ A group represented by —S—(R ９０５) (Specific example group G9) includes -S(G1), -S(G2), -S(G3), and -S(G6). 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.

[0056] ・「-N(R ９０６ ) (R ９０７ A group represented by —N(R ９０６ ) (R ９０７ Specific examples (specific example group G10) of groups represented by the formula (G1) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). 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. Multiple G1s in -N(G1)(G1) may be the same as or different from one another. Multiple G2s in -N(G2)(G2) may be the same as or different from one another. Multiple G3s in -N(G3)(G3) may be the same as or different from one another. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0057] "Halogen Atom" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0058] "Substituted or unsubstituted fluoroalkyl group" The term "substituted or unsubstituted fluoroalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The term "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "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" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms have been replaced with fluorine atoms.

[0059] "Substituted or unsubstituted haloalkyl group" As used herein, a "substituted or unsubstituted haloalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. Note that the "substituted haloalkyl group" described herein also includes a "substituted haloalkyl group" in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain are further replaced with a substituent, and a "substituted haloalkyl group" in which one or more hydrogen atoms of the substituent are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. A haloalkyl group may also be referred to as a halogenated alkyl group.

[0060] - "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 a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0061] - "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0062] - "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0063] - "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0064] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from one another. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0065] "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), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3, 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 embodiment 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 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

[0066] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.

[0067] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

[0068] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0069]

[0070] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0071]

[0072] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0073] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0074]

[0075] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0076] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.

[0077] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0078] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0079] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

[0080] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).

[0081]

[0082]

[0083] In the general formulae (TEMP-42) to (TEMP-52), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0084]

[0085] In the general formulae (TEMP-53) to (TEMP-62), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. ９ and Q １０ may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents the bonding position.

[0086]

[0087] In the general formulae (TEMP-63) to (TEMP-68), Q １ ~Q ８ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0088] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).

[0089]

[0090]

[0091]

[0092] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0093]

[0094]

[0095]

[0096]

[0097] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0098] The above is the explanation of "substituents described in this specification."

[0099] "When bonded to form a ring" In this specification, when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other," it means when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle," when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring," and when "one or more pairs of adjacent groups do not bond to each other." In this specification, the cases when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle" and "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when bonded to form a ring") will be explained below. An anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be described as an example.

[0100]

[0101] For example, R ９２１~R ９３０ In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the pair of adjacent two groups is R ９２１ and R ９２２ Paired with R ９２２ and R ９２３ Paired with R ９２３ and R ９２４ Paired with R ９２４ and R ９３０ Paired with R ９３０ and R ９２５ Paired with R ９２５ and R ９２６ Paired with R ９２６ and R ９２７ Paired with R ９２７ and R ９２８ Paired with R ９２８ and R ９２９ and R ９２９ and R ９２１ It is paired with.

[0102] The above-mentioned "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and simultaneously form R ９２５ and R ９２６ and are bonded to each other to form ring Q Ｂ When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0103]

[0104] The case where a "set of two or more adjacent groups" forms a ring includes not only the case where a set of "two" adjacent groups is bonded as in the above example, but also the case where a set of "three or more" adjacent groups is bonded. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and R ９２２ and R ９２３ and are bonded to each other to form ring Q Ｃ and three adjacent (R ９２１ , R ９２２ and R９２３ In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): Ａ and Ring Q Ｃ is R ９２２ Share.

[0105]

[0106] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), Ａ and Ring Q Ｂ are "monocyclic rings" or "fused rings". Ａ , and ring Q Ｃ is a "fused ring". Ａ and Tamaki Q Ｃ That is, Ring Q Ａ and Tamaki Q Ｃ The ring Q in the general formula (TMEP-104) is fused to form a fused ring. Ａ is a benzene ring, then ring Q Ａ The ring Q in the general formula (TMEP-104) is a monocyclic ring. Ａ is a naphthalene ring, then ring Q Ａ is a fused ring.

[0107] The term "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of aromatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of aromatic heterocyclic rings include structures in which the aromatic heterocyclic groups given as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups given 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 main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R ９２１ and R ９２２ and a ring Q formed by bonding together Ａ is R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. ９２１ and R ９２２ Todekan Q Ａ In the case where R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ When a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, R ９２１ and R ９２２ The ring formed by

[0108] Here, unless otherwise specified herein, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In any element (for example, in the case of carbon or nitrogen), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When any element other than a carbon element is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more arbitrary elements" constituting the monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of the "monocycle" and the "fused ring," the "monocycle" is preferred. Unless otherwise specified herein, of the "saturated ring" and the "unsaturated ring," the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocycle" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0109] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." The above is an explanation of the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0110] In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, 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 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ are each independently 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ９０１ When there are two or more R９０１ are the same or different from each other, R ９０２ When there are two or more R ９０２ are the same or different from each other, R ９０３ When there are two or more R ９０３ are the same or different from each other, R ９０４ When there are two or more R ９０４ are the same or different from each other, R ９０５ When there are two or more R ９０５ are the same or different from each other, R ９０６ When there are two or more R ９０６ are the same or different from each other, R ９０７ When there are two or more R ９０７ are the same or different from each other.

[0111] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

[0112] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[0113] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."

[0114] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-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. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituents further possessed by the optional substituent are the same as those of the optional substituents described above.

[0115] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0116] [First embodiment] <Compound> The compound according to the first embodiment is a compound represented by the following formula (1).

[0117]

[0118] (In the formula (1), Z １ , Z ２ , and Z ３ are each independently a nitrogen atom, or C(R ３１ ), where Z １ ~Z ３ At least two of R are nitrogen atoms; １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , and R １８one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ２１ , R ２２ , R ２３ , R ２４ , R ２５ , R ２６ , R ２７ , and R ２８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３１ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R９３５ ), a group represented by —B(R ９３６ ) (R ９３７ ), a group represented by —B(OR ９３８ ) (OR ９３９ a group represented by —O—S(═O) ２ (R ９４０ 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, provided that at least one condition selected from the group consisting of the following conditions (i), (ii), and (iii) is satisfied: Condition (i): R １ ~R ８ Condition (ii): At least one of R １１ ~R １８ Condition (iii): At least one of R ２１ ~R ２８ At least one of the four Ax's is a substituted or unsubstituted phenyl group. p is 4, and at least one pair of adjacent two or more Ax's are not bonded to each other, and each Ax is independently a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -C(R ９０１Ｂ ) (R ９０２Ｂ ) (R ９０３Ｂ a group represented by —Si(R ９０１Ａ ) (R ９０２Ａ ) (R ９０３Ａ 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, ９０１ ~R ９０７ , R ８０１ ~R ８０２ , and R ９３１ ~R ９４０ are each independently 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R９０１Ａ , R ９０２Ａ , R ９０３Ａ , R ９０１Ｂ , R ９０２Ｂ , and R ９０３Ｂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, R ９３１ If there are multiple R ９３１ are the same or different from each other, R ９３２ If there are multiple R ９３２ are the same or different from each other, R ９３３ If there are multiple R ９３３ are the same or different from each other, R ９３４ If there are multiple R ９３４ are the same or different from each other, R ９３５ If there are multiple R ９３５are the same or different from each other, R ９３６ If there are multiple R ９３６ are the same or different from each other, R ９３７ If there are multiple R ９３７ are the same or different from each other, R ９３８ If there are multiple R ９３８ are the same or different from each other, R ９３９ If there are multiple R ９３９ are the same or different from each other, R ９４０ If there are multiple R ９４０ are the same or different from each other, R ９０１Ａ If there are multiple R ９０１Ａ are the same or different from each other, R ９０２Ａ If there are multiple R ９０２Ａ are the same or different from each other, R ９０３Ａ If there are multiple R ９０３Ａ are the same or different from each other, R ９０１Ｂ If there are multiple R ９０１Ｂ are the same or different from each other, R ９０２Ｂ If there are multiple R ９０２Ｂ are the same or different from each other, R ９０３Ｂ If there are multiple R ９０３Ｂ are the same or different from each other.)

[0119] The compound according to this embodiment can extend the life of an organic electroluminescence device.

[0120] In one embodiment, the compound represented by formula (1) is １ ~Z ３ Any one of C(R ３１ ), then R ３１ and R which does not form a substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ ~R ８ , R １１ ~R １８ , and R ２１~R ２８ In one embodiment, the compound represented by formula (1) is １ ~Z ３ Any one of C(R ３１ ), then R ３１ and Ax that does not form a substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring are not bonded to each other.

[0121] In one embodiment of the compound represented by formula (1), Ax which does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring is R １ ~R ８ In one embodiment of the compound represented by formula (1), Ax that does not form a substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring is R １１ ~R １８ In one embodiment of the compound represented by formula (1), Ax that does not form a substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring is R ２１ ~R ２８ does not combine with

[0122] The compound represented by the formula (1) preferably satisfies the condition (i). It is also preferable that the compound represented by the formula (1) satisfies only the condition (i).

[0123] In the compound represented by formula (1), R １ ~R ８ It is also preferable that no pair of two or more adjacent groups among the above are bonded to each other.

[0124] In the compound represented by formula (1), R １１ ~R １８ It is also preferable that no pair of two or more adjacent groups among the above are bonded to each other.

[0125] In the compound represented by formula (1), R ２１ ~R ２８ It is also preferable that no pair of two or more adjacent groups among the above are bonded to each other.

[0126] In the compound represented by formula (1), R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ , and R ３１ It is also preferable that at least one of the groups is a deuterium atom.

[0127] In the compound represented by formula (1), it is also preferred that the hydrogen atoms possessed by the substituted or unsubstituted phenyl group under at least one condition selected from the group consisting of the conditions (i), (ii), and (iii) are protium atoms or deuterium atoms. In the compound represented by formula (1), it is also preferred that all of the hydrogen atoms possessed by the substituted or unsubstituted phenyl group under at least one condition selected from the group consisting of the conditions (i), (ii), and (iii) are deuterium atoms.

[0128] In the compound represented by the formula (1), it is also preferable that all of the hydrogen atoms possessed by the substituted or unsubstituted phenyl group in the condition (i) are deuterium atoms.

[0129] In the compound represented by the formula (1), it is also preferable that all of the hydrogen atoms possessed by the substituted or unsubstituted phenyl group in the condition (ii) are deuterium atoms.

[0130] In the compound represented by the formula (1), it is also preferable that all of the hydrogen atoms of the substituted or unsubstituted phenyl group in the condition (iii) are deuterium atoms.

[0131] In the compound represented by the formula (1), Z １ ~Z ３ Two of the nitrogen atoms are nitrogen atoms, and Z １ ~Z ３ One of them is C(R ３１ In the compound represented by formula (1), Z １ ~Z ３ Two of the nitrogen atoms are nitrogen atoms, and Z １ ~Z ３ One of them is C(R３１ ) and R ３１ It is also preferred that is a hydrogen atom.

[0132] In the compound represented by the formula (1), Z １ is a nitrogen atom, and Z ２ and Z ３ Any of Z is a nitrogen atom, and Z is not a nitrogen atom. ２ and Z ３ is C(R ３１ ) and R ３１ It is also preferred that is a hydrogen atom.

[0133] In the compound represented by the formula (1), Z １ ~Z ３ It is also preferred that all of are nitrogen atoms.

[0134] In the compound represented by the formula (1), Z ２ It is also preferred that is a nitrogen atom.

[0135] In the compound represented by the formula (1), Z １ ~Z ３ Two of the nitrogen atoms are nitrogen atoms, and Z １ ~Z ３ One of them is C(R ３１ ), then Z １ and Z ２ is a nitrogen atom, and Z ３ is C(R ３１ ) is more preferable.

[0136] In the compound represented by the formula (1), Z １ ~Z ３ Two of the nitrogen atoms are nitrogen atoms, and Z １ ~Z ３ One of them is C(R ３１ ), then Z １ and Z ３ is a nitrogen atom, and Z ２ is C(R ３１ ) is more preferable.

[0137] In the compound represented by the formula (1), Z １ ~Z ３ Two of the nitrogen atoms are nitrogen atoms, and Z １~Z ３ One of them is C(R ３１ ), then Z ２ and Z ３ is a nitrogen atom, and Z １ is C(R ３１ ) may also be used.

[0138] In the compound represented by formula (1), the substituted or unsubstituted phenyl group in at least one condition selected from the group consisting of conditions (i), (ii), and (iii) is preferably an unsubstituted phenyl group.

[0139] In the compound represented by the formula (1), the substituted or unsubstituted phenyl group in the condition (i) is preferably an unsubstituted phenyl group.

[0140] In the compound represented by the formula (1), the substituted or unsubstituted phenyl group in the condition (ii) is preferably an unsubstituted phenyl group.

[0141] In the compound represented by the formula (1), the substituted or unsubstituted phenyl group in the condition (iii) is preferably an unsubstituted phenyl group.

[0142] The compound represented by the formula (1) satisfies the condition (i) and has R which is not a substituted or unsubstituted phenyl group. １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ It is also preferable that R is a hydrogen atom. １ ~R ８ At least one of R is a substituted or unsubstituted phenyl group, and the remaining R is not a substituted or unsubstituted phenyl group. １ ~R ８ And, R １１ ~R １８ and R ２１ ~R ２８ and are preferably both hydrogen atoms.

[0143] The compound represented by the formula (1) satisfies the condition (i) and R １ ~R８ It is more preferable that at least one of the groups is an unsubstituted phenyl group.

[0144] The compound represented by the formula (1) satisfies the condition (i) and R １ ~R ８ At least one of R is a substituted or unsubstituted phenyl group, １ ~R ８ It is also preferred that the remainder of all be hydrogen atoms.

[0145] The compound represented by the formula (1) satisfies the condition (i) and R １ ~R ８ At least one of R is a substituted or unsubstituted phenyl group, １ ~R ８ It is also preferable that the remaining atoms are all deuterium atoms. The compound represented by the formula (1) satisfies the condition (i) and R １ ~R ８ one of R is a substituted or unsubstituted phenyl group; １ ~R ８ It is also preferable that the remaining atoms are all deuterium atoms. The compound represented by the formula (1) satisfies the condition (i) and R ２ ~R ７ one of R is an unsubstituted phenyl group, １ ~R ８ It is also preferred that the remainder of all be deuterium atoms.

[0146] The compound represented by the formula (1) does not satisfy the condition (ii), and R １１ ~R １８ It is also preferred that all of are deuterium atoms.

[0147] The compound represented by the formula (1) does not satisfy the condition (iii) and R ２１ ~R ２８ It is also preferred that all of are deuterium atoms.

[0148] The compound represented by the formula (1) does not satisfy the conditions (ii) and (iii), and R １１ ~R １８ and R ２１ ~R ２８It is also preferred that all of are deuterium atoms.

[0149] In one embodiment of the compound represented by formula (1), one or more pairs of two or more adjacent Ax's are not bonded to each other.

[0150] In the compound represented by the formula (1), each of the four Ax independently represents a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R ９０１Ａ ) (R ９０２Ａ ) (R ９０３Ａ ), 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.

[0151] R in Ax ９０１Ａ , R ９０２Ａ and R ９０３Ａ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0152] In the compound represented by the formula (1), each of the four Ax independently represents a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, —Si(R ９０１Ａ ) (R ９０２Ａ ) (R ９０３Ａ ) a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; ９０１Ａ , R ９０２Ａ and R ９０３Ａ are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms.

[0153] In the compound represented by formula (1), it is also preferable that at least one of the four Ax is a group represented by the following formula (A-10x) or formula (A-10y).

[0154]

[0155] [(In the formula (A-10x), R １１Ｅ ~R １９Ｅ any one of the R １１Ｅ ~R １９Ｅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.) (In the formula (A-10y), X Ｅ is an oxygen atom, a sulfur atom, or C(R ２９１Ｅ ) (R ２９２Ｅ ) and R ２１Ｅ ~R ２８Ｅ , R ２９１Ｅ and R ２９２Ｅ any one of the four Ax is a bonding position to a ring-forming carbon of the benzene ring to which any one of the four Ax is bonded in the formula (1), ２９１Ｅ and R ２９２Ｅ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R ２１Ｅ ~R ２８Ｅ and R that is not the bonding position, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. ２９１Ｅ and R ２９２Ｅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0156] In the compound represented by the formula (1), at least one of the four Ax is X Ｅ is C(R ２９１Ｅ ) (R ２９２ＥThat is, in the compound represented by formula (1), at least one of the four Ax is a group represented by formula (A-10y), and X in the group represented by formula (A-10y) is preferably a group represented by formula (A-10y). Ｅ But C(R ２９１Ｅ ) (R ２９２Ｅ ) is also preferred.

[0157] In the compound represented by the formula (1), at least one of the four Ax is a group represented by the formula (A-10x), or X Ｅ is also preferably a group represented by the above formula (A-10y) in which is an oxygen atom or a sulfur atom.

[0158] In the compound represented by formula (1), it is also preferable that at least one of the four Ax is a group represented by the following formula (A-10x): １９Ｅ is the bonding position of the ring carbon of the benzene ring to which any of the four Ax's is bonded in the formula (1), and R １１Ｅ ~R １８Ｅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0159] In one embodiment of the group represented by formula (A-10x), R １１Ｅ ~R １８Ｅ In one embodiment of the group represented by formula (A-10y), R ２１Ｅ ~R ２８Ｅ is preferably a hydrogen atom.

[0160] In one embodiment of the group represented by formula (A-10y), X Ｅ is preferably an oxygen atom. In one embodiment of the group represented by formula (A-10y), X Ｅ is an oxygen atom, and R is not the bonding position. ２１Ｅ ~R２８Ｅ is preferably a hydrogen atom.

[0161] In the compound represented by formula (1), it is also preferable that at least one of the four Ax is a group represented by formula (A-10z) below.

[0162]

[0163] (In the formula (A-10z), R ３０Ｅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, and a plurality of R ３０Ｅ are the same or different. * represents a bonding position.)

[0164] In one embodiment of the group represented by formula (A-10z), R ３０Ｅ is preferably a hydrogen atom.

[0165] In the compound represented by formula (1), when at least one of the four Ax is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferably a substituted or unsubstituted phenyl group, and more preferably an unsubstituted phenyl group. That is, in the compound represented by formula (1), when at least one of the four Ax is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferably a substituted or unsubstituted phenyl group, and more preferably an unsubstituted phenyl group.

[0166] In the compound represented by the formula (1), it is also preferable that the four Ax's are hydrogen atoms.

[0167] In one embodiment of the compound represented by formula (1), when four Ax are hydrogen atoms, four Ax are protium atoms. In one embodiment of the compound represented by formula (1), when four Ax are hydrogen atoms, four Ax are deuterium atoms.

[0168] In the compound represented by the formula (1), at least one of the four Ax is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R ９０１Ａ ) (R ９０２Ａ ) (R ９０３Ａ ), 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.

[0169] In the compound represented by formula (1), it is preferable that the four Ax are not substituted or unsubstituted fluoroalkyl groups.

[0170] The compound represented by the formula (1) is preferably a compound represented by the following formula (1A):

[0171]

[0172] (In the formula (1A), Z １ ~Z ３ , and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are Z in the formula (1), respectively. １ ~Z ３ , and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ is synonymous with A １ , A ２ , A ３ and A ４ each independently has the same meaning as Ax in formula (1).

[0173] In the formula (1A), A １ ~A ４ are each independently a hydrogen atom or a deuterium atom, and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８are each preferably independently a hydrogen atom or a deuterium atom.

[0174] In the formula (1A), R satisfies the condition (i) and is not a substituted or unsubstituted phenyl group. １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are all deuterium atoms, and A １ ~A ４ In the formula (1A), it is also preferable that all of R are deuterium atoms and R is not a substituted or unsubstituted phenyl group and satisfies the condition (i). １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are all deuterium atoms, and A １ ~A ４ In the formula (1A), it is also preferable that all of R are hydrogen atoms. １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are all deuterium atoms, and A １ ~A ４ are also preferably all hydrogen atoms or all deuterium atoms.

[0175] In the formula (1A), Z ２ is a nitrogen atom, and Z １ and Z ３ is a nitrogen atom, and Z １ and Z ３ The other is C(R ３１ ), then R ３１ is preferably a protium atom or a deuterium atom.

[0176] The compound represented by formula (1) is also preferably a compound represented by formula (101), formula (102), formula (103), or formula (104) below.

[0177]

[0178]

[0179]

[0180]

[0181] (In the formulas (101), (102), (103), and (104), Z １ ~Z ３ , and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are Z in the formula (1), respectively. １ ~Z ３ , and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ is synonymous with A １ ~A ４ each independently has the same meaning as Ax in formula (1), １０１ , R １０２ , R １０３ , R １０４ , and R １０５ is a hydrogen atom.)

[0182] In one embodiment of the compounds represented by the formula (101), the formula (102), the formula (103), and the formula (104), R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ In one embodiment of the compounds represented by the formula (101), the formula (102), the formula (103), and the formula (104), A １ ~A ４ Any pair of two or more adjacent ones of these is not bonded to each other.

[0183] In one embodiment of the compound represented by formula (101), R １０１ ~R１０５ are all R ５ , R ７ , or R ８ In one embodiment of the compound represented by formula (102), R １０１ ~R １０５ are all R ５ , R ６ , or R ７ In one embodiment of the compound represented by formula (102), R １０１ ~R １０５ are all A １ ~A ４ In one embodiment of the compound represented by formula (103), R １０１ ~R １０５ are all R ６ , R ７ , or R ８ In one embodiment of the compound represented by formula (104), R １０１ ~R １０５ are all R ５ , R ６ , or and R ８ It does not combine with .

[0184] In the formulas (101), (102), (103), and (104), A １ ~A ４ , and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ is also preferably a hydrogen atom.

[0185] In the formulas (101), (102), (103), and (104), A １ ~A ４ , and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ is also preferably a hydrogen atom.

[0186] In the formulas (101), (102), (103), and (104), R１ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ , and R ３１ At least one selected from the group consisting of is a deuterium atom, and R １０１ ~R １０５ It is also preferred that all of are hydrogen atoms.

[0187] In the formulas (101), (102), (103), and (104), R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ , and R ３１ At least one selected from the group consisting of is a deuterium atom, and R １０１ ~R １０５ It is also preferred that all of are deuterium atoms.

[0188] In the formulas (101), (102), (103), and (104), Z １ ~Z ３ Among them, at least Z １ is a nitrogen atom, and C(R ３１ ) R ３１ are deuterium atoms, and A １ ~A ４ are hydrogen atoms, and R ５ ~R ８ are hydrogen atoms, and R １ ~R ４ , R １１ ~R １８ , and R ２１ ~R ２８ are deuterium atoms, and R １０１ ~R １０５ It is also preferred that all of are deuterium atoms.

[0189] In the formulas (101), (102), (103), and (104), Z １ ~Z ３ Among them, at least Z １ is a nitrogen atom, and C(R ３１ ) R３１ are deuterium atoms, and A １ ~A ４ are hydrogen atoms, and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are deuterium atoms, and R １０１ ~R １０５ It is also preferred that all of are deuterium atoms.

[0190] In the formulas (101), (102), (103), and (104), R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ It is also preferred that is a deuterium atom.

[0191] In the formulas (101), (102), (103), and (104), R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ is a deuterium atom, and A １ ~A ４ It is also preferred that is a hydrogen atom.

[0192] In the formulas (101), (102), (103), and (104), R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ is a deuterium atom, and A １ ~A ４ It is also preferred that is a hydrogen atom.

[0193] In the formulas (101), (102), (103), and (104), Z １ , Z ２ and Z ３ It is also preferred that is a nitrogen atom.

[0194] In the formulas (101), (102), (103), and (104), Z ２ is a nitrogen atom, and Z １ and Z ３ It is also preferred that at least one of the groups is a nitrogen atom.

[0195] In the formulas (101), (102), (103), and (104), Z ２ is a nitrogen atom, and Z １ and Z ３ is a nitrogen atom, and Z １ and Z ３ The other is C(R ３１ ) is also preferred.

[0196] In the compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0197] In the compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is also preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0198] In the compounds according to this embodiment, all groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[0199] In the compounds according to this embodiment, when the term "substituted or unsubstituted" is used, the hydrogen atom in the "unsubstituted" group is preferably a protist atom or a deuterium atom.

[0200] The compound according to this embodiment is preferably a material used in an emitting layer. The compound according to this embodiment is preferably a host material. The compound according to this embodiment is preferably a thermally activated delayed fluorescent compound. The compound according to this embodiment may be a sensitizing material. The compound according to this embodiment may be both a sensitizing material and a thermally activated delayed fluorescent compound. In this specification, thermally activated delayed fluorescence may be referred to as delayed fluorescence. In this specification, the compound according to the first embodiment may be referred to as the first compound.

[0201] (Thermally activated delayed fluorescence) Delayed fluorescence is explained on pages 261 to 268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In this document, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is １３ It has been explained that if the transition probability can be reduced, reverse energy transfer from the excited triplet state, which normally has a low transition probability, to the excited singlet state occurs with high efficiency, resulting in the manifestation of thermally activated delayed fluorescence (TADF). Furthermore, Figure 10.38 in this document explains the mechanism of delayed fluorescence generation. The TADF mechanism utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet and triplet levels is used. Known examples of compounds exhibiting thermally activated delayed fluorescence (TADF properties) (hereinafter also referred to as TADF compounds) include compounds in which a donor moiety and an acceptor moiety are bonded within the molecule.

[0202] In general, delayed fluorescence can be confirmed by transient PL (Photoluminescence) measurement.

[0203] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a technique in which a sample is excited by irradiating it with a pulsed laser and then measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in TADF compounds is classified into emission components from singlet excitons generated during the initial PL excitation and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, emission from these singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emission from singlet excitons generated via triplet excitons, which have a long lifetime. Thus, there is a large time difference between emission from singlet excitons generated during the initial PL excitation and emission from singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be determined.

[0204] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Figure 1. An example of a method for measuring transient PL and an analysis of the behavior of delayed fluorescence will be described below.

[0205] 1 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in FIG.

[0206] The sample accommodated in the sample chamber 102 is obtained by forming a thin film on a quartz substrate, in which the doping material is doped at a concentration of 12 mass % relative to the matrix material.

[0207] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed in the sample chamber 102 to excite the doping material. Emission light is extracted in a direction 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by a spectrometer 103, forming a two-dimensional image in a streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity. Cutting out this two-dimensional image along a predetermined time axis yields an emission spectrum in which the vertical axis represents emission intensity and the horizontal axis represents wavelength. Furthermore, cutting out the two-dimensional image along the wavelength axis yields a decay curve (transient PL) in which the vertical axis represents the logarithm of emission intensity and the horizontal axis represents time.

[0208] For example, a thin film sample A was prepared as described above using the following compound HX1 as the matrix material and the following compound DX1 as the doping material, and transient PL measurement was carried out.

[0209]

[0210] Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following compound HX2 as a matrix material and the above-mentioned compound DX1 as a doping material.

[0211] FIG. 2 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0212]

[0213] As described above, transient PL measurement can be used to obtain an emission decay curve with the vertical axis representing emission intensity and the horizontal axis representing time. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly, is somewhat large.

[0214] Specifically, luminescence from delayed fluorescent materials includes prompt luminescence and delay luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength that the delayed fluorescent material absorbs. Delay luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0215] The amounts of Prompt luminescence and Delay luminescence and their ratio can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amounts of Prompt luminescence and Delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 1.

[0216] Furthermore, when the compound according to this embodiment is a delayed fluorescent compound, a sample prepared by the following method is used to measure the delayed fluorescence of the delayed fluorescent compound. For example, a delayed fluorescent compound according to this embodiment is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. To prevent quenching by oxygen, the sample solution is frozen and degassed, and then sealed in a lidded cell under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield is calculated according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0217] In this embodiment, the amount of prompt luminescence (prompt luminescence) of the compound to be measured is X Ｐ The amount of delayed light emission is set to X Ｄ When this is done, X Ｄ / X ＰThe amount and ratio of prompt luminescence and delay luminescence of compounds other than the delayed fluorescent compound in this specification are measured in the same manner as the amount and ratio of prompt luminescence and delay luminescence of the delayed fluorescent compound according to this embodiment.

[0218] (ΔST) In this embodiment, the lowest excited singlet energy S １ and the energy gap T at 77[K] ７７Ｋ The difference between (S １ -T ７７Ｋ ) is defined as ΔST.

[0219] (Relationship Between Triplet Energy and Energy Gap at 77 K) Here, the relationship between triplet energy and the energy gap at 77 K will be described. In this embodiment, the energy gap at 77 K differs from the triplet energy as typically defined. Triplet energy is measured as follows. First, a sample is prepared by dissolving a compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. A phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) is measured for this sample at low temperature (77 K). A tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated using a predetermined conversion formula based on the wavelength value at the intersection of the tangent line and the horizontal axis. Among the compounds according to this embodiment, the thermally activated delayed fluorescence compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 K), resulting in a mixture of excited singlet and excited triplet states. As a result, the spectrum measured in the same manner as above contains light emission from both the excited singlet state and the excited triplet state, and it is difficult to clearly distinguish which state the light emission is from, but the triplet energy value is considered to be basically dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that it is different in the strict sense, the value measured as follows is referred to as the energy gap T ７７ＫThe compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to obtain a solution with a concentration of 10 μmol / L, and this solution is placed in a quartz cell to be used as a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), and a tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. ｅｄｇｅ Based on the energy gap T at 77 [K], the amount of energy calculated from the following conversion formula (F1) is ７７Ｋ Conversion formula (F1): T ７７Ｋ [eV]=1239.85 / λ ｅｄｇｅ

[0220] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corporation. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.

[0221] (Lowest excited singlet energy S １ ) The lowest excited singlet energy S １The following method can be used as a measurement method (sometimes referred to as the solution method): A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. ｅｄｇｅ The lowest excited singlet energy is calculated by substituting [nm] into the following conversion formula (F2): Conversion formula (F2): S １ [eV]=1239.85 / λ ｅｄｇｅ An example of an absorption spectrum measuring device is a spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd., but is not limited to this.

[0222] A tangent to the fall of the absorption spectrum on the long wavelength side is drawn as follows: When moving along the spectral curve from the longest maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction of longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall of the absorption spectrum on the long wavelength side. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0223] (Method for Producing Compound According to This Embodiment) The compound according to this embodiment can be produced according to the synthesis method described in the Examples below, or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0224] (Specific Examples of Compounds According to This Embodiment) Specific examples of compounds according to this embodiment include the following compounds. However, the present invention is not limited to these specific examples. In this specification, among the specific examples of compounds, D may represent a deuterium atom, Me may represent a methyl group, Ph may represent a phenyl group, tBu may represent a tert-butyl group, and tAm may represent a tert-amyl group.

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300] Second Embodiment <Material for Organic Electroluminescence Device> The material for organic electroluminescence devices according to the second embodiment contains the compound according to the first embodiment. One embodiment includes a material for organic electroluminescence devices containing only the compound according to the first embodiment. Another embodiment includes a material for organic electroluminescence devices containing the compound according to the first embodiment and another compound different from the compound according to the first embodiment. In the material for organic electroluminescence devices according to the second embodiment, the compound according to the first embodiment is preferably a host material. In this specification, when the compound according to the first embodiment is a host material, the host material is referred to as a first host material. The material for organic electroluminescence devices according to one embodiment may contain a first host material (the compound according to the first embodiment) and another compound such as a dopant material. The material for organic electroluminescence devices according to one embodiment may contain a first host material (the compound according to the first embodiment), a second host material different from the first host material, and a dopant material. In the material for organic electroluminescence devices according to one embodiment, the first host material may be a sensitizing material. In the material for an organic electroluminescence device according to one embodiment, the first host material may be a sensitizing material and a delayed fluorescent compound.

[0301] [Third Embodiment] <Organic Electroluminescent Element> (Light-Emitting Unit) One aspect of the organic EL element according to the third embodiment includes an anode, a cathode, and an light-emitting unit disposed between the anode and the cathode. In one aspect, the light-emitting unit contains the compound according to the first embodiment as a first compound. In the organic EL element according to this embodiment, the light-emitting band is contained in the light-emitting unit. The light-emitting unit may have one or more layers containing at least one material selected from the group consisting of an organic compound and an inorganic material, in addition to the one or more light-emitting layers contained in the light-emitting band. The inorganic material is at least one of an inorganic compound and a simple substance. The light-emitting unit preferably includes one or more layers selected from the group consisting of a layer composed of an organic compound, a layer composed of an inorganic material, and a layer composed of both an organic compound and an inorganic material. In addition to the one or more light-emitting layers, examples of layers that the light-emitting unit may include include layers that can be used in organic EL elements. Layers that can be used in organic EL elements are not particularly limited, but include, for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a blocking layer.

[0302] In one aspect of the third embodiment, a hole transport layer is included between the anode and the light-emitting layer closest to the anode among the one or more light-emitting layers. In one aspect of the third embodiment, an electron transport layer is included between the cathode and the light-emitting layer closest to the cathode among the one or more light-emitting layers.

[0303] Fig. 3 shows a schematic configuration of an example of an organic EL element according to the third embodiment. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and an emitting unit 10 disposed between the anode 3 and the cathode 4. The emitting unit 10 is configured by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, an emitting layer 5, an electron transport layer 8, and an electron injection layer 9. The present invention is not limited to the configuration of the organic EL element shown in Fig. 3.

[0304] (Light-emitting layer) In a third embodiment, the light-emitting unit has one or more light-emitting layers. In a third embodiment, at least one layer of the one or more light-emitting layers contains the compound according to the first embodiment as a first compound. In a third embodiment, at least one layer of the one or more light-emitting layers contains the compound according to the first embodiment (first compound) as a first host material.

[0305] In one aspect of the third embodiment, at least one of the one or more emitting layers contains a first host material and a phosphorescent metal complex or a fluorescent material. In one aspect of the third embodiment, when at least one of the one or more emitting layers contains a fluorescent material, the emitting layer does not contain a phosphorescent metal complex. In one aspect of the third embodiment, when at least one of the one or more emitting layers contains a phosphorescent metal complex, the emitting layer does not contain a fluorescent material. In one aspect of the third embodiment, at least one of the one or more emitting layers may further contain a second host material.

[0306] In one aspect of the third embodiment, at least one layer of the one or more emissive layers contains a first host material and a dopant material. In one aspect of the third embodiment, the dopant material is a phosphorescent metal complex or a fluorescent material. In one aspect of the third embodiment, the first host material and the dopant material are contained in a single layer. For example, when the organic EL device has one emissive layer, the first host material and the dopant material are contained in the single emissive layer, and when the organic EL device has multiple emissive layers, the first host material and the dopant material are contained in any single emissive layer of the multiple emissive layers.

[0307] [First Host Material] In the third embodiment, the first host material is the compound according to the first embodiment (first compound). The first host material may be a sensitizing material. The embodiments in which the first host material is a sensitizing material will be described in the sixth and seventh embodiments.

[0308] [Second Host Material] In the third embodiment, the second host material may be the same as the second host material in the fifth embodiment described later.

[0309] Dopant Material In one aspect of the third embodiment, the dopant material is a phosphorescent metal complex or a fluorescent material.

[0310] (Phosphorescent Metal Complex) In the third embodiment, the phosphorescent metal complex preferably contains a heavy metal atom. In the third embodiment, the phosphorescent metal complex preferably contains one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0311] In the third embodiment, the phosphorescent metal complex is preferably a compound represented by the following formula (21): M(L １ ) ｎ１ (L ２ ) ｎ２ …(21)

[0312]

[0313] (In the formulas (21), (211), (212), and (213), M is a transition metal selected from the group consisting of first transition metals, second transition metals, and third transition metals; L １ is at least one ligand selected from the group consisting of a ligand represented by the formula (211), a ligand represented by the formula (212), and a ligand represented by the formula (213), n1 is 1, 2, or 3, L ２ is at least one ligand selected from the group consisting of monodentate, bidentate and tridentate ligands; n2 is 0, 1, 2, 3 or 4; CY １ Tamaki, C.Y. ２ Tamaki, C.Y. ３ Ring and CY ４each ring is independently selected from the group consisting of a carbocyclic group having 5 to 30 ring carbon atoms and a heterocyclic group having 1 to 30 ring carbon atoms; １ ~Y ４ are each independently a single bond, a double bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, *a-O-*b, *a-S-*b, *a-C(=O)-*b, *a-S(=O)-*b, *a-C(R ５ ) (R ６ )-*b, *a-C(R ５ ) = C(R ６ )-*b, *a-C(R ５ )=*b, *a-Si(R ５ ) (R ６ )-*b, *a-B(R ５ )-*b, *a-N(R ５ )-*b, and *a-P(R ５ a1, a2, and a3 are each independently 1, 2, or 3; a4 is 0, 1, 2, or 3; and when a4 is 0, CY １ Ring and CY ４ The rings are not connected to each other, and １ , T ２ , T ３ and T ４ are each independently a chemical bond, *a-O-*b, *a-S-*b, *a-B(R ７ )-*b, *a-N(R ７ )-*b, *a-P(R ７ )-*b, *a-C(R ７ ) (R ８ )-*b, *a-Si(R ７ ) (R ８ )-*b, *a-Ge(R ７ ) (R ８*a and *b are each independently a bonding position to an adjacent atom, *1, *2, *3 and *4 are bonding positions to M, and R １ ~R ８ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si(R ２５１ ) (R ２５２ ) (R ２５３ a group represented by —O—(R ２５４ a group represented by —S—(R ２５５ a group represented by —N(R ２５６ ) (R ２５７ a group represented by —C(═O)R ２５８ a group represented by —C(═O)(OR ２５９ a group represented by —S(═O) ２ (OR ２６０ ), a group represented by —O—P(═O)(OR ２６１ ) (OR ２６２ ), a group represented by —C(R ２６３ ) (R ２６４ ) (R ２６５ ), a group represented by —B(R ２６６ ) (R ２６７ a group represented by —P(R ２６８ ) (R２６９ ), a group represented by —S(═O)(R ２７０ a group represented by —S(═O) ２ (R ２７１ ), a group represented by —P(═O)(R ２７２ ) (R ２７３ ) and a group represented by —P(═S)(R ２７４ ) (R ２７５ R １ ~R ８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １ ~R ８ , and Y １ ~Y ４ one or more pairs of adjacent two or more of the following are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or not bonded to each other; b1, b2, b3, and b4 are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; R ２５１ ~R ２７５ are each independently a hydrogen atom, a halogen atom, or —O—(R ２７６ a group represented by —N(R ２７７ ) (R ２７８), a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms substituted with a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R is selected from the group consisting of a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a biphenylyl group, and a terphenylyl group; ２７６ ~R ２７８ are each independently 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0314] As used herein, a carbocyclic group having 5 to 30 ring carbon atoms refers to a monocyclic or polycyclic group having 5 to 30 ring carbon atoms containing only carbon as ring atoms. The carbocyclic group having 5 to 30 ring carbon atoms may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The carbocyclic group having 5 to 30 ring carbon atoms may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, depending on the number of substituents bonded to the carbocyclic group having 5 to 30 ring carbon atoms, various modifications are possible, such as a trivalent group or a tetravalent group.

[0315] In this specification, a heterocyclic group having 1 to 30 ring carbon atoms refers to a group which has the same structure as a carbocyclic group having 5 to 30 ring carbon atoms, but which contains, as a ring-forming atom, at least one heteroatom selected from N (nitrogen atom), O (oxygen atom), Si (silicon atom), P (phosphorus atom) and S (sulfur atom) in addition to carbon (which may have 1 to 30 carbon atoms).

[0316] In this specification, a heterocycloalkyl group having 3 to 50 ring atoms means a monovalent monocyclic group having 3 to 50 ring atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring atom, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. In this specification, a heterocycloalkylene group having 3 to 50 ring atoms means a divalent group having the same structure as a heterocycloalkyl group having 3 to 50 ring atoms.

[0317] In this specification, a cycloalkenyl group having 3 to 50 ring carbon atoms refers to a monovalent monocyclic group having 3 to 50 ring carbon atoms and having at least one double bond in the ring but not having aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. In this specification, a cycloalkenylene group having 3 to 50 ring carbon atoms refers to a divalent group having the same structure as a cycloalkenyl group having 3 to 50 ring carbon atoms.

[0318] As used herein, a heterocycloalkenyl group having 3 to 50 ring atoms is a monovalent monocyclic group having 3 to 50 ring atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring atom, and having at least one double bond within the ring. Specific examples of heterocycloalkenyl groups having 3 to 50 ring atoms include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. As used herein, a heterocycloalkenylene group having 3 to 50 ring atoms refers to a divalent group having the same structure as a heterocycloalkenyl group having 3 to 50 ring atoms.

[0319] According to one embodiment, in the compound represented by formula (21), the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms, the substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms, the substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms, and the substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms.

[0320] As used herein, a monovalent non-aromatic fused polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are fused together, which contains only carbon as ring-forming atoms, and the entire molecule has non-aromaticity. As used herein, a divalent non-aromatic fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

[0321] In this specification, a monovalent non-aromatic hetero-fused polycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are fused together and which contains, in addition to carbon as ring-forming atoms, at least one heteroatom selected from N, O, Si, P, and S, and the entire molecule is non-aromatic. In this specification, a divalent non-aromatic hetero-fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic hetero-fused polycyclic group.

[0322] In this specification, the term "biphenylyl group" refers to a "phenyl group substituted with a phenyl group." The "biphenylyl group" belongs to the category of "substituted phenyl groups" whose substituent is an "aryl group having 6 to 50 ring carbon atoms."

[0323] In this specification, the term "terphenylyl group" refers to a "phenyl group substituted with a biphenylyl group." The "terphenylyl group" belongs to the "substituted phenyl group" whose substituent is an "aryl group having 6 to 50 ring carbon atoms substituted with an aryl group having 6 to 50 ring carbon atoms."

[0324] In the compound represented by the formula (21), T １ , T ２ , T ３ and T ４ The chemical bond as is preferably a single bond.

[0325] In the compound represented by formula (21), M is preferably one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm), and more preferably platinum (Pt) or iridium (Ir).

[0326] According to one embodiment, in the compound represented by formula (21), CY １ Ring ~ CY ４The rings each independently represent benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenophene, indole, benzoborol, benzophosphole, indene, benzosilole, benzogermole, benzothiophene, benzoselenophene, benzofuran, carbazole, dibenzoborol, dibenzophosphole, fluorene, dibenzosilole, dibenzogermole, dibenzothiophene, dibenzoselenophene, dibenzofuran, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindole, azabenzoborole, azabenzophosphole, azaindene, azabenzosilole, azabenzogermole, azabenzothiophene, azabenzoselenophene, azabenzofuran, The compound may be selected from the group consisting of azacarbazole, azadibenzoborole, azadibenzophosphole, azafluorene, azadibenzosilole, azadibenzogermole, azadibenzothiophene, azadibenzoselenophene, azadibenzofuran, azadibenzothiophene 5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline.

[0327] According to one embodiment, CY in formula (211) １ Ring and CY ２ At least one of the rings, CY in formula (212) １ Ring ~ CY ３ At least one of the rings and CY in formula (213) １ Ring ~ CY ４At least one of the rings may be a carbene.

[0328] According to one embodiment, Y in formulas (211) to (213) １ ~Y ４ are each independently a single bond, a double bond, *a-O-*b, *a-S-*b, *a-C(R ５ ) (R ６ )-*b and *a-N(R ５ )-*b.

[0329] According to one embodiment, in formula (211), R １ and R ２ In formula (212), R １ ~R ３ and in formula (213), R １ ~R ４ At least one of the groups may be an electron donating group.

[0330] For example, the electron-donating group may be an isopropyl group, a tert-butyl group, and a substituent selected from the group consisting of the following formulae (10-1) to (10-61):

[0331]

[0332]

[0333] In the formulas (10-1) to (10-61), * indicates the bonding position to the adjacent atom.

[0334] In this specification, a deuterium atom is represented as D in a chemical formula, and a proton atom is represented as H or is omitted. In this specification, a methyl group may be represented as Me, a phenyl group as Ph, an isopropyl group as i-Pr, and a t-butyl group as t-Bu in a chemical formula.

[0335] According to one embodiment, R in formula (211) １ and R ２ and / or at least one of Y １ is *a-N(R ５) - * b, and R ５ may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0336] According to one embodiment, R in formula (212) １ ~R ３ and / or at least one of Y １ and Y ２ At least one of *a-N(R ５ ) - * b, and R ５ may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0337] According to one embodiment, R in formula (213) １ ~R ４ and / or at least one of Y １ ~Y ４ At least one of *a-N(R ５ ) - * b, and R ５ may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0338] (Specific Examples of Phosphorescent Metal Complexes) Specific examples of the phosphorescent metal complexes of the third embodiment include the following compounds: However, the present invention is not limited to these specific examples of compounds.

[0339]

[0340]

[0341]

[0342] (Fluorescent Material) In the third embodiment, the fluorescent material is preferably a compound that does not exhibit thermally activated delayed fluorescence. In the third embodiment, the fluorescent material is not a phosphorescent metal complex. In the third embodiment, the fluorescent material is preferably not a metal complex. In this specification, a compound used as a fluorescent material may be referred to as a third compound.

[0343] Examples of fluorescent materials include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing boron atoms, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0344] In the third embodiment, the fluorescent material is one or more compounds selected from the group consisting of third compounds represented by the following formula (41):

[0345]

[0346] (In the formula (41), the ring a, the ring b, and the ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, and L ４０１ and L ４０２ are each independently O, S, Se, or NR ４０ , C(R ４１ ) (R ４２ ), or Si(R ４３ ) (R ４４ ) and L ４０３ is B, P, or P=O, and R ４０ ~R ４４ each independently represents a ring a, a ring b, or a ring c bonded to form a substituted or unsubstituted monocycle, a ring a, a ring b, or a ring c bonded to form a substituted or unsubstituted fused ring, or a ring a, a ring b, or a ring c not bonded to the ring, ４１ and R ４２ are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, R ４３ and R４４ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. ４０ ~R ４４ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N; 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, ４５ is a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R ４０ If there are multiple R ４０ are the same or different from each other, R ４１ If there are multiple R ４１ are the same or different from each other, R ４２ If there are multiple R ４２ are the same or different from each other, R ４３ If there are multiple R ４３ are the same or different from each other, R ４４ If there are multiple R ４４ are the same or different from each other, R ４５ If there are multiple R ４５ are the same or different from each other.)

[0347] In the third embodiment, the compound represented by the formula (41) is preferably a compound represented by the following formula (410):

[0348]

[0349] (In the formula (410), the ring a, the ring b, and the ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, and R ４０１ and R ４０２ each independently represents R which bonds with the ring a, ring b, or ring c to form a substituted or unsubstituted monocycle, R which bonds with the ring a, ring b, or ring c to form a substituted or unsubstituted fused ring, or R which does not bond with the ring a, ring b, or ring c to form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N; 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.

[0350] In the third embodiment, the compound represented by the formula (41) is preferably a compound selected from the group consisting of compounds represented by the following formulas (41-1) to (41-6):

[0351]

[0352]

[0353]

[0354] (In the formula (41-1), Xa is O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３and R ４０２ Paired with R ４０２ and R ４２４ Paired with R ４２４ ~R ４２７ a set of two or more adjacent ４２７ and R ４１２ and R ４１２ and R ４１１ and one or more pairs selected from the group consisting of: R ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N; 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１１ , R ４１２ , and R ４２１ ~R ４２７ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, 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, ９０１ ~R ９０７ are each independently 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other.) (In the formula (41-2), Xa is O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４２４ Paired with R ４２４ ~R ４２７ a set of two or more adjacent４１３ and R ４１４ and R ４１４ and R ４０１ and one or more pairs selected from the group consisting of: R ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N; 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１３ , R ４１４ , and R ４２１ ~R ４２７ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the formula (41-1). Ｘ is synonymous with R ４０３ If there are multiple R ４０３ are the same or different from each other, R ４０４ If there are multiple R ４０４ are the same or different from each other, R ４０５ If there are multiple R ４０５ are the same or different.) (In the formula (41-3), Xa and Xb each independently represent O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４１５ and R ４１６ Paired with R ４１６ and R ４１２ and R ４１２ and R ４１１ and one or more pairs selected from the group consisting of: R ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N; 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１１ , R ４１２ , R ４１５ , R ４１６ , and R ４２１ ~R ４２３ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the formula (41-1). Ｘ is synonymous with R ４０３ If there are multiple R ４０３ are the same or different from each other, R ４０４ If there are multiple R ４０４ are the same or different from each other, R ４０５ If there are multiple R ４０５are the same or different.) (In the formula (41-4), Xa and Xb each independently represent O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４１８ Paired with R ４１８ and R ４１７ and R ４１２ and R ４１１ and one or more pairs selected from the group consisting of: R ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N; 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１１ , R ４１２ , R ４１７ , R ４１８ , and R ４２１ ~R ４２３ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the formula (41-1). Ｘ is synonymous with R ４０３If there are multiple R ４０３ are the same or different from each other, R ４０４ If there are multiple R ４０４ are the same or different from each other, R ４０５ If there are multiple R ４０５ are the same or different.) (In the formula (41-5), Xa and Xb each independently represent O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４１８ Paired with R ４１８ and R ４１７ Paired with R ４１３ and R ４１４ and R ４１４ and R ４０１ and one or more pairs selected from the group consisting of: R ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N; 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１３ , R ４１４, R ４１７ , R ４１８ , and R ４２１ ~R ４２３ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the formula (41-1). Ｘ is synonymous with R ４０３ If there are multiple R ４０３ are the same or different from each other, R ４０４ If there are multiple R ４０４ are the same or different from each other, R ４０５ If there are multiple R ４０５ are the same or different.) (In the formula (41-6), R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４２４ Paired with R ４２４ ~R ４２７ a set of two or more adjacent ４２７ and R ４２８ Paired with R ４２８ ~R ４３１ and R ４３１ and R ４０１ and one or more pairs selected from the group consisting of: R ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５an iminyl group represented by ═N, 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, wherein R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring; ４２１ ~R ４３１ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the formula (41-1). Ｘ is synonymous with

[0355] In the compounds represented by the formulas (41-1) to (41-5), R ４１２ and R ４１１ Paired with R ４１３ and R ４１４ Paired with R ４１５ and R ４１６ and R ４１７ and R ４１８ and

[0356] In the third embodiment, the compound represented by the formula (41) is also preferably a compound represented by the following formula (41-7):

[0357]

[0358] (In the formula (41-7), Xa is O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４２４ Paired with R ４２４ ~R ４２７ and R ４３７ ~R ４４０are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. ４０１ and R ４０２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 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; R ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４２１ ~R ４２７ and R ４３７ ~R ４４０ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the formula (41-1). Ｘ is synonymous with

[0359] (Method for producing the compound represented by formula (41)) The compound represented by formula (41) can be produced by a known method. The compound represented by formula (41) can also be produced by following a known method and using known alternative reactions and raw materials suited to the target product.

[0360] (Specific Examples of Compounds Represented by Formula (41)) Specific examples of the compounds represented by formula (41) include the following compounds: In the specific examples below, D represents a deuterium atom, Me represents a methyl group, tBu represents a tertiary butyl group, and Ph represents a phenyl group.

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the formulas is 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 ９０１ａ ) (R ９０２ａ ) (R ９０３ａ ), -O-(R ９０４ａ ), -S-(R ９０５ａ ), -N(R ９０６ａ ) (R ９０７ａ ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ａ ~R ９０７ａ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ａ When two or more R ９０１ａ are the same or different, R ９０２ａ When two or more R ９０２ａ are the same or different, R ９０３ａ When two or more R ９０３ａ are the same or different, R ９０４ａ When two or more R ９０４ａ are the same or different, R ９０５ａ When two or more R ９０５ａ are the same or different, R ９０６ａ When two or more R９０６ａ are the same or different, R ９０７ａ When two or more R ９０７ａ are the same as or different from each other.

[0370] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the formulas is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0371] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the formulas is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0372] (Maximum Peak Wavelength) In the third embodiment, the maximum peak wavelength of the phosphorescent metal complex and the maximum peak wavelength of the third compound as the fluorescent material are each independently preferably 480 nm or less, more preferably 475 nm or less. In the third embodiment, the maximum peak wavelength of the phosphorescent metal complex and the maximum peak wavelength of the third compound as the fluorescent material are each independently preferably 430 nm or more, more preferably 440 nm or more. In this specification, the maximum peak wavelength of fluorescent emission may be referred to as the maximum peak wavelength of fluorescent emission, and the maximum peak wavelength of phosphorescent emission may be referred to as the maximum peak wavelength of phosphorescent emission. In the organic EL element of the third embodiment, the phosphorescent metal complex and the fluorescent material preferably emit blue light. In this specification, blue light emission refers to light emission having a maximum peak wavelength of the emission spectrum (fluorescent spectrum or phosphorescent spectrum) in the range of 430 nm or more and 480 nm or less.

[0373] (Emission spectrum half width) In the third embodiment, the emission spectrum half width FWHM of the third compound as the fluorescent material is preferably 40 nm or less, more preferably 30 nm or less. In the third embodiment, the emission spectrum half width FWHM of the third compound as the fluorescent material is preferably 5 nm or more, more preferably 10 nm or more. FWHM is an abbreviation for full width at half maximum.

[0374] In this specification, the maximum fluorescence emission peak wavelength is the wavelength at which the compound to be measured is 10 －６ moles / liter or more, 10 －５ The FWHM is the maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in a fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of 1 mole / liter or less. The emission spectrum half width FWHM is the full width at half maximum at the maximum peak of the fluorescence spectrum. A fluorescence spectrum measuring device can be used to measure the fluorescence spectrum. For example, a fluorescence spectrum measuring device (device name: FP-8300) manufactured by JASCO Corporation can be used. Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.

[0375] The maximum phosphorescence emission peak wavelength can be measured by the following method. The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at 10 －５ mol / L or more 10 －４ The EPA solution is dissolved to a concentration of 0.01 mol / L or less, and the resulting EPA solution is placed in a quartz cell to serve as a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), and the shortest wavelength maximum of the phosphorescence spectrum is taken as the maximum phosphorescence peak wavelength. A spectrofluorometer F-7000 (manufactured by Hitachi High-Tech Science Corporation) can be used to measure phosphorescence. However, the measurement device is not limited to this, and measurements may also be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light-receiving device.

[0376] (Stokes Shift) In the third embodiment, the Stokes shift of the third compound as a fluorescent material is preferably 25 nm or less, more preferably 20 nm or less. In the third embodiment, the Stokes shift of the third compound as a fluorescent material is preferably 5 nm or more, more preferably 10 nm or more. When the Stokes shift of the third compound is 20 nm or less, excitation energy can be reduced. When the Stokes shift of the third compound is 10 nm or more, self-absorption can be suppressed and loss of efficiency can be reduced. The Stokes shift can be measured by the following method. The compound to be measured is added to 2.0 × 10 －５ The compound to be measured is dissolved in toluene at a concentration of 1000 mol / L to prepare a measurement sample. The measurement sample is placed in a quartz cell and irradiated with continuous light in the ultraviolet-visible region at room temperature (300 K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the absorption spectrum, for example, a spectrophotometer U-3900 / 3900H model manufactured by Hitachi High-Tech Science Corporation. The compound to be measured is dissolved in 4.9 x 10 －６ The sample is dissolved in toluene at a concentration of 100 mol / L to prepare a measurement sample. The measurement sample placed in a quartz cell is irradiated with excitation light at room temperature (300 K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the fluorescence spectrum, and for example, a Hitachi High-Tech Science F-7000 fluorescence spectrophotometer can be used. From these absorption and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength is calculated to determine the Stokes shift (SS). The unit of the Stokes shift SS is nm.

[0377] In the third embodiment, when at least one layer of the one or more emitting layers contains a first host material and a fluorescent material, it is preferable that when the organic EL device is caused to emit light, the fluorescent compound mainly emits light in the emitting layer.

[0378] The maximum peak wavelength of light emitted from the organic EL element is measured as follows: ２A voltage is applied to the organic EL element so that the spectral radiance spectrum obtained is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

[0379] (Compound Content in Emitting Layer) The contents of the first host material (first compound) and dopant material contained in the emitting layer are preferably within the following ranges, for example. In this specification, the compound content in the emitting layer refers to the content of the compound contained in a single layer. The content of the first host material is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of the first host material may be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99.9% by mass or less, or even 99% by mass or more and 99.9% by mass or less. The content of the dopant material is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. Note that the third embodiment does not exclude the case where at least one of the one or more emitting layers contains a material other than the first host material and the dopant material. At least one of the one or more light-emitting layers may contain only one type of first host material or two or more types of first host materials. At least one of the one or more light-emitting layers may contain only one type of dopant material or two or more types of dopant materials.

[0380] (Thickness of the Light-Emitting Layer) The thickness of the light-emitting layer in the organic EL element of the third embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity, and when the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress an increase in driving voltage. In this specification, the thickness of the light-emitting layer refers to the thickness of the single light-emitting layer when the organic EL element has one light-emitting layer, and refers to the thickness of each layer of the multiple light-emitting layers when the organic EL element has multiple light-emitting layers. In other words, when the organic EL element has multiple light-emitting layers, the thickness of each layer is preferably 5 nm or more and 50 nm or less.

[0381] The structure of the organic EL element will be further described.

[0382] (Substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor deposition films can also be used.

[0383] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include 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 metal materials (e.g., titanium nitride).

[0384] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1 mass % to 10 mass % of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 mass % to 5 mass % of tungsten oxide and 0.1 mass % to 1 mass % of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like.

[0385] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, and therefore materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0386] Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet printing can be used.

[0387] When the organic EL element is a bottom-emission type, the anode is preferably formed of a metal material having optical transparency or semi-transparency that transmits light from the light-emitting layer. In this specification, optical transparency or semi-transparency means a property that transmits 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The optically transparent or semi-transparent metal material can be appropriately selected from the materials listed in the anode section.

[0388] When the organic EL device is a top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a metal material having optical reflectivity. In this specification, optical reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having optical reflectivity can be appropriately selected from the materials listed in the anode section. The anode may be composed of only a reflective layer, or may have a multilayer structure having a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer be disposed between the reflective layer and the hole-transporting region. The conductive layer can be appropriately selected from the materials listed in the anode section.

[0389] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0390] When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used.

[0391] By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0392] When the organic EL element is a bottom-emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed of a metal material having light reflectivity. The metal material having light reflectivity can be appropriately selected from the materials listed in the section on the cathode.

[0393] When the organic EL element is a top-emission type, the cathode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the cathode section.

[0394] The organic EL element according to the third embodiment may be a bottom-emission organic EL element. The organic EL element according to this embodiment may also be a top-emission organic EL element. When the organic EL element is a bottom-emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflectivity. When the organic EL element is a top-emission type, it is preferable that the anode is a light-reflective electrode having light reflectivity, and the cathode is a light-transmitting electrode having light transparency.

[0395] (Capping Layer) When the organic EL element is a top-emission type, the organic EL element usually has a capping layer on the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain, for example, at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. A laminate obtained by stacking layers containing these substances can also be used as the capping layer.

[0396] (Hole Injection Layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, or manganese oxide. Furthermore, examples of the material with high hole injection properties include low-molecular-weight organic compounds such as 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), and 1, Examples of the aromatic amine compound include 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), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1). Furthermore, a polymer compound (such as an oligomer, dendrimer, or polymer) can also be used as the substance with high hole injection properties. Examples of such polymer compounds include 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), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD).Furthermore, polymer compounds to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0397] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), 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: NPB), Examples of aromatic amine compounds that can be used include 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 substances mentioned here are mainly 10 －６ cm ２ The hole-transporting layer may be a material having a hole mobility of 1 / Vs or more. Carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth may be used for the hole-transporting layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used. However, other materials may also be used as long as they have a higher hole-transporting property than electron-transporting property. The layer containing the material having a high hole-transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned materials are stacked.

[0398] (Electron Transport Layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds can be used. Specifically, low-molecular organic compounds such as Alq and tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq) can be used. ３ ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq ２ ), BAlq, Znq, ZnPBO, ZnBTZ, and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: OXD-8), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. The substances mentioned here are mainly 10 －６ cm ２ / Vs or more. Note that other substances may be used as the electron-transporting layer as long as they have a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be a single layer or a stack of two or more layers made of the above-mentioned substances. A polymer compound may also be used for the electron-transporting layer. For example, 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), or the like may be used.

[0399] (Electron Injection Layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF ２Alkali metals, alkaline earth metals, or compounds thereof, such as lithium oxide (LiOx), may be used. Alternatively, a material having electron transport properties containing an alkali metal, alkaline earth metal, or compound thereof, such as magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material containing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such composite materials have excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, the above-mentioned materials constituting the electron transport layer (e.g., metal complexes and heteroaromatic compounds) may be used. The electron donor may be any material that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0400] (Layer Formation Method) The method for forming each layer of the organic EL element according to any of the above-described embodiments is not limited to those specifically mentioned above, but may be any known method such as a dry film formation method such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0401] (Film Thickness) The film thickness of each layer included in the light-emitting unit of the organic EL element according to the third embodiment is not limited unless specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, it is usually preferable that the film thickness of each layer included in the light-emitting unit of the organic EL element be in the range of several nm to 1 μm.

[0402] According to the organic EL element of the third embodiment, the lifetime of the organic EL element can be extended. According to one aspect of the organic EL element of the third embodiment, by incorporating a phosphorescent complex (preferably a blue phosphorescent complex) and a compound according to the first embodiment (first compound) as a first host material in the light-emitting layer, the lifetime of the organic EL element can be extended. According to one aspect of the organic EL element of the third embodiment, by incorporating a fluorescent material (preferably a blue fluorescent material) and a compound according to the first embodiment (first compound) as a first host material in the light-emitting layer, the lifetime of the organic EL element can be extended. The organic EL element of the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0403] [Fourth Embodiment] The configuration of an organic EL element according to a fourth embodiment will be described. In the description of the fourth embodiment, the same components as those in the third embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[0404] (Light-emitting layer) In the organic EL element according to the fourth embodiment, at least one of the one or more light-emitting layers contains a first host material, a sensitizing material, and a fluorescent material. The other features are the same as those of the organic EL element according to the third embodiment. The first host material, the sensitizing material, and the fluorescent material are different materials. In the fourth embodiment, the compound used as the sensitizing material may be referred to as a second compound. That is, in the fourth embodiment, at least one of the one or more light-emitting layers contains a first host material (first compound), a sensitizing material (second compound), and a fluorescent material (third compound).

[0405] In a fourth embodiment, the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescent compounds. In one aspect of the fourth embodiment, at least one of the one or more emitting layers contains a first host material, a delayed fluorescent compound as a sensitizing material, and a fluorescent material. In this aspect, it is preferable that at least one of the one or more emitting layers does not contain a phosphorescent metal complex. In one aspect of the fourth embodiment, at least one of the one or more emitting layers contains a first host material, a phosphorescent metal complex as a sensitizing material, and a fluorescent material.

[0406] In the fourth embodiment, the first host material, the sensitizing material, and the fluorescent material are contained in a single layer. For example, when the organic EL element has one light-emitting layer, the first host material, the sensitizing material, and the fluorescent material are contained in the single light-emitting layer, and when the organic EL element has multiple light-emitting layers, the first host material, the sensitizing material, and the fluorescent material are contained in any one of the multiple light-emitting layers.

[0407] [First Host Material] In the fourth embodiment, the first host material is the compound according to the first embodiment (the compound (first compound) represented by the formula (1)).

[0408] [Fluorescent Material] In the fourth embodiment, the fluorescent material may be the same as the fluorescent material (third compound) described in the third embodiment.

[0409] [Sensitizing Material] In the fourth embodiment, the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescent compounds.

[0410] (Phosphorescent Metal Complex) In the fourth embodiment, the phosphorescent metal complex may be made of the same material as the phosphorescent metal complex described in the third embodiment.

[0411] (Delayed Fluorescent Compound) In the fourth embodiment, the delayed fluorescent compound is not a phosphorescent metal complex. In the fourth embodiment, it is preferable that the delayed fluorescent compound is not a metal complex.

[0412] In the fourth embodiment, the delayed fluorescent compound is preferably a compound represented by the following formula (H1).

[0413]

[0414] (In the formula (H1), A Ｈ is a group having at least one partial structure selected from the group consisting of the following formulae (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7), and (a-8), and D Ｈ is a group represented by the following formula (221), (222) or (223), Ｈ represents a single bond, a substituted or unsubstituted aryl ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, m is 1, 2, 3, 4, or 5, and a plurality of A Ｈ are the same or different from each other, n is 1, 2, 3, 4 or 5, and a plurality of D Ｈ are the same or different from each other.)

[0415]

[0416] (In the formulas (a-1) to (a-8), * each independently represents a bonding position to another atom in the molecule of the delayed fluorescent compound.)

[0417]

[0418]

[0419]

[0420] (R in the formula (221) ２１ ~R ２８ one or more pairs of adjacent two or more of R in the formula (222) are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ２２１ ~R ２２８ one or more pairs of adjacent two or more of R in the formula (223) are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ２３１ ~R ２３８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form a substituted or unsubstituted monocycle in the formula (221) and do not form a substituted or unsubstituted fused ring; ２１ ~R ２８ R in the formula (222) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. ２２１ ~R ２２８ and R in the formula (223) that does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring. ２３１ ~R ２３８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ 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, in the formula (222) and the formula (223), ring A, ring B, and ring C are each independently any ring structure selected from the group consisting of ring structures represented by the following formulas (224) and (225), ring A, ring B, and ring C are fused to an adjacent ring at any position, p, px, and py are each independently 1, 2, 3, or 4, when p is 2, 3, or 4, multiple rings A are the same or different from each other, when px is 2, 3, or 4, multiple rings B are the same or different from each other, when py is 2, 3, or 4, multiple rings C are the same or different from each other, * in the formulas (221) to (223) represents L Ｈ indicates the bonding position with

[0421]

[0422] (In the formula (224), r is 0, 2 or 4, and a plurality of R ２９ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and in the formula (225), X Ａ is a sulfur atom, an oxygen atom, or C(R ２９１ ) (R ２９２ ) and R ２９１ and R ２９２are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form a substituted or unsubstituted monocycle and a substituted or unsubstituted fused ring; ２９ , R ２９１ and R ２９２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ 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, ２９ are the same or different from each other, and a plurality of R ２９１ are the same or different from each other, and a plurality of R ２９２ are the same or different from each other, and a plurality of X Ａ are the same or different from each other.)

[0423] (In the delayed fluorescent compound, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , R ９０７ , R ９０８ , R ９０９ , R ９３１ , R ９３２ , R ９３３ , R ９３４ , R ９３５ , R ９３６ and R ９３７ are each independently 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R ９０８ If there are multiple R ９０８ are the same or different from each other, R ９０９ If there are multiple R ９０９ are the same or different from each other, R ９３１ If there are multiple R ９３１ are the same or different from each other, R９３２ If there are multiple R ９３２ are the same or different from each other, R ９３３ If there are multiple R ９３３ are the same or different from each other, R ９３４ If there are multiple R ９３４ are the same or different from each other, R ９３５ If there are multiple R ９３５ are the same or different from each other, R ９３６ If there are multiple R ９３６ are the same or different from each other, R ９３７ If there are multiple R ９３７ are the same or different from each other.)

[0424] In the fourth embodiment, the delayed fluorescent compound is preferably a compound represented by the following formula (H10).

[0425]

[0426] (In the formula (H10), CN is a cyano group, and L Ｈ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, １１ and D １２ are each independently a group represented by the formula (221), (222) or (223), m is 1, 2, 3, 4 or 5, nx is 0, 1, 2, 3, 4 or 5, ny is 0, 1, 2, 3, 4 or 5, nx + ny is 1, 2, 3, 4 or 5, D １１ and D １２ are the same or different from each other, and a plurality of D １１ are the same or different from each other, and a plurality of D １２ are the same or different from each other.)

[0427] In the fourth embodiment, the delayed fluorescent compound is preferably a compound represented by the following formula (H100).

[0428]

[0429] (In the formula (H100), L Ｈ , D １１ , D １２ , m, nx, and ny are L in the formula (H10), respectively. Ｈ , D １１ , D １２ , m, nx and ny are synonymous with each other, and each R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a cyano group, a nitro group, a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ 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, provided that at least one R is a substituent, and at least one R as the substituent is L of the compound represented by formula (H100). Ｈ is bonded to by a carbon-carbon bond, k is an integer of 1 or more, and the multiple R's are the same or different.

[0430] In the fourth embodiment, the delayed fluorescent compound is preferably a compound represented by the following formula (H101).

[0431]

[0432] (In the formula (H101), D １１ and D １２ are the D in the formula (H10), respectively. １１ and D １２ each R is independently defined as R in the formula (H100), m is 1, 2, 3, or 4, nx is 0, 1, 2, 3, or 4, ny is 0, 1, 2, 3, or 4, k is 1, 2, 3, or 4, nx+ny is 1, 2, 3, or 4, and m+nx+ny+k=6.

[0433] In the fourth embodiment, the delayed fluorescent compound is preferably a compound represented by the following formula (H110), (H120), or (H130).

[0434]

[0435] (In the formulae (H110), (H120) and (H130), D １１ and D １２ are the D in the formula (H10), respectively. １１ and D １２ each R is independently defined as R in the formula (H100); nx is 0, 1, 2, or 3; ny is 0, 1, 2, or 3; k is 1, 2, or 3; nx+ny is 1, 2, or 3; and nx+ny+k=4.

[0436] In the fourth embodiment, the group represented by the formula (222) in the delayed fluorescent compound is preferably any one group selected from the group consisting of groups represented by the following formulas (22A), (22B), (22C), (22D), (22E), and (22F):

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443] (In the formulae (22A), (22B), (22C), (22D), (22E) and (22F), R ２２１ ~R ２２８ are R in the formula (222), respectively. ２２１ ~R ２２８ is synonymous with R ２２９ and R ２３０ are each independently R in the formula (224). ２９ is synonymous with X Ａ is X in the formula (225). Ａ In the formulae (22A), (22B), (22C), (22D), (22E) and (22F), * indicates a bonding position.

[0444] In the organic EL element according to the fourth embodiment, when the delayed fluorescent compound is a compound represented by formula (H101), * in formulas (22A), (22B), (22C), (22D), (22E), and (22F) is bonded to the benzene ring itself explicitly shown in formula (H101).

[0445] In the delayed fluorescent compound of the fourth embodiment, X Ａ is also preferably a sulfur atom or an oxygen atom.

[0446] In the delayed fluorescent compound of the fourth embodiment, X Ａ But C(R ２９１ ) (R ２９２ ), then R ２９１ and R ２９２are each independently preferably 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and more preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0447] In the delayed fluorescent compound of the fourth embodiment, R ２１ ~R ２８ In the delayed fluorescent compound of the fourth embodiment, it is also preferable that any pair of adjacent two or more of R ２２１ ~R ２２８ In the delayed fluorescent compound of the fourth embodiment, it is also preferable that any pair of adjacent two or more of R ２３１ ~R ２３８ It is also preferred that any pair of two or more adjacent groups of the above is not bonded to each other.

[0448] In the delayed fluorescence compound of the fourth embodiment, each R is preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0449] In the delayed fluorescence compound of the fourth embodiment, each R is preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0450] R in the delayed fluorescent compound of the fourth embodiment ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 and R ２９are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0451] R in the delayed fluorescent compound of the fourth embodiment ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 and R ２９ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0452] In the delayed fluorescence compound of the fourth embodiment, R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 and R ２９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0453] In the delayed fluorescence compound of the fourth embodiment, R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 and R２９ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0454] In the compound according to the fourth embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ an unsubstituted aralkyl group having 7 to 50 carbon atoms; —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a group represented by —S(═O) ２ R ９３８ a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, ９０１ ~R ９０９ , and R ９３１ ~R ９３８ are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0455] In the compound according to the fourth embodiment, the substituent in the case of being “substituted or unsubstituted” is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0456] In the compound according to the fourth embodiment, the substituent in the case of being "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0457] In the compound according to the fourth embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0458] In this specification, when the delayed fluorescent compound is a sensitizing material, the lowest excited singlet energy of the delayed fluorescent compound is S １ (GT2), and the energy gap of the delayed fluorescent compound at 77 [K] is T ７７Ｋ (GT2) and S １ (GT2) and T ７７Ｋ The difference between (GT2) and ΔST(GT2) may be referred to as ΔST(GT2).

[0459] (Method for producing delayed fluorescent compound) The delayed fluorescent compound in the fourth embodiment can be produced by a known method. The delayed fluorescent compound can also be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0460] (Specific Examples of Delayed Fluorescence Compound) Specific examples of the delayed fluorescence compound in the fourth embodiment include the following compounds, however, the present invention is not limited to these specific examples.

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467] (Relationship between the first host material, the sensitizing material, and the fluorescent material in the emitting layer) In one aspect of the fourth embodiment, the sensitizing material is a delayed fluorescent compound. In one aspect of the fourth embodiment, at least one layer of the one or more emitting layers contains a delayed fluorescent compound as a sensitizing material, but may not contain a phosphorescent metal complex.

[0468] FIG. 4 shows an example of the relationship between the energy levels of a first host material (first compound), a delayed fluorescent compound (second compound) as a sensitizing material, and a fluorescent material (third compound) in an emitting layer. In FIG. 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first host material, and T1(M1) represents the lowest excited triplet state of the first host material. S1(M2) represents the lowest excited singlet state of the delayed fluorescent compound, and T1(M2) represents the lowest excited triplet state of the delayed fluorescent compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from S1(M2) to S1(M3) in FIG. 4 represents Förster energy transfer from the lowest excited singlet state of the delayed fluorescent compound to the lowest excited singlet state of the fluorescent material. As shown in Figure 4, when a compound with a small ΔST (M2) is used as the delayed fluorescent compound, the lowest excited triplet state T1 (M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1 (M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1 (M2) of the delayed fluorescent compound to the fluorescent material, generating the lowest excited singlet state S1 (M3). As a result, fluorescence emission from the lowest excited singlet state S1 (M3) of the fluorescent material can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0469] In one embodiment, the lowest excited singlet energy S of the delayed fluorescent compound １(GT2) and the lowest excited singlet energy S of the fluorescent material １ It is also preferable that (D) satisfies the relationship of the following mathematical formula (Mathematical Formula 4): S １ (GT2)>S １ (D) ... (Equation 4)

[0470] In one embodiment, the lowest excited singlet energy S of the first host material １ (H1) and the lowest excited singlet energy S of the delayed fluorescent compound １ It is also preferable that (GT2) satisfies the relationship of the following mathematical formula (Mathematical Formula 4A): １ (H1)>S １ (GT2) ... (Math 4A)

[0471] In one embodiment, the lowest excited singlet energy S of the first host material, the delayed fluorescent compound, and the fluorescent material １ It is also preferable that S satisfies the relationship of the following mathematical formula (Mathematical Formula 4B): １ (H1)>S １ (GT2)>S １ (D) ... (Math 4B)

[0472] In one embodiment, the energy gap T at 77 [K] of the first host material and the delayed fluorescent compound ７７Ｋ It is also preferable that T satisfies the relationship of the following formula (Formula 6): ７７Ｋ (H1)>T ７７Ｋ (GT2) ... (Equation 6)

[0473] In one embodiment, the delayed fluorescent compound has an energy gap T at 77 [K]. ７７Ｋ (GT2) and the energy gap T of the fluorescent material at 77 [K] ７７Ｋ It is also preferable that (D) satisfies the relationship of the following mathematical formula (Mathematical Formula 6A): T ７７Ｋ (GT2)>T ７７Ｋ (D) ... (Math 6A)

[0474] In one embodiment, the first host material, the delayed fluorescent compound, and the fluorescent material have an energy gap T at 77 [K]. ７７Ｋ It is also preferable that T satisfies the relationship of the following formula (Formula 6B): ７７Ｋ (H1)>T７７Ｋ (GT2)>T ７７Ｋ (D) ...(Math 6B)

[0475] In one embodiment, the sensitizing material is a phosphorescent metal complex. In one embodiment, at least one layer of the one or more light-emitting layers contains a phosphorescent metal complex as a sensitizing material, and may not contain a delayed fluorescent compound.

[0476] 5 shows an example of the relationship between the energy levels of a first host material (first compound), a phosphorescent metal complex (second compound) as a sensitizing material, and a fluorescent material (third compound) in an emitting layer. In FIG. 5 , S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first host material, and T1(M1) represents the lowest excited triplet state of the first host material. S1(M2) represents the lowest excited singlet state of the phosphorescent metal complex, and T1(M2) represents the lowest excited triplet state of the phosphorescent metal complex. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from T1(M2) to S1(M3) in FIG. 5 represents dipole-type energy transfer from the lowest excited triplet state of the phosphorescent metal complex to the lowest excited singlet state of the fluorescent material. As shown in FIG. 5 , when a phosphorescent metal complex is used as a sensitizer, the lowest excited singlet state S1(M2) of the phosphorescent metal complex can undergo intersystem crossing to the lowest excited triplet state T1(M2) due to spin-orbit interactions and heavy atom effects. Dipole-type energy transfer then occurs from the lowest excited triplet state T1(M2) of the phosphorescent metal complex to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that this mechanism can theoretically increase the internal quantum efficiency to 100%.

[0477] In one embodiment, the energy gap T at 77 [K] of the phosphorescent metal complex ７７Ｋ (GP2) and the lowest excited singlet energy S of the fluorescent material １It is also preferable that (D) satisfies the relationship of the following mathematical formula (Mathematical Formula 3): T ７７Ｋ (GP2)>S １ (D) ... (Equation 3)

[0478] In one embodiment, the energy gap T at 77 [K] of the first host material and the phosphorescent metal complex ７７Ｋ It is also preferable that T satisfies the relationship of the following formula (Formula 3A): ７７Ｋ (H1)>T ７７Ｋ (GP2) …(Math 3A)

[0479] In one embodiment, the energy gap T at 77 [K] of the first host material and the phosphorescent metal complex ７７Ｋ and the lowest excited singlet energy S of the fluorescent material. １ It is also preferable that (D) satisfies the relationship of the following mathematical formula (Mathematical Formula 3B): T ７７Ｋ (H1)>T ７７Ｋ (GP2)>S １ (D) ...(Math 3B)

[0480] The lowest excited singlet energy S of the fluorescent material １ (D) and the energy gap T of the fluorescent material at 77 [K] ７７Ｋ (D) usually satisfies the relationship of the following formula (Formula 3C): S １ (D) > T ７７Ｋ (D) ...(Math 3C)

[0481] In one embodiment, the lowest excited singlet energy S of the first host material １ (H1) and the lowest excited singlet energy S of the phosphorescent metal complex １ It is also preferable that (GP2) satisfies the relationship of the following mathematical formula (Mathematical Formula 5): S １ (H1)>S １ (GP2) ... (Equation 5)

[0482] In one embodiment, the lowest excited singlet energy S of the phosphorescent metal complex １ (GP2) and the lowest excited singlet energy S of the fluorescent material １ It is also preferable that (D) satisfies the relationship of the following mathematical formula (Mathematical Formula 5A): S １ (GP2)>S １(D) ...(Number 5A)

[0483] In one embodiment, the lowest excited singlet energy S of the first host material, the phosphorescent metal complex, and the fluorescent material １ It is also preferable that S satisfies the relationship of the following mathematical formula (Mathematical Formula 5B): １ (H1)>S １ (GP2)>S １ (D) ...(Number 5B)

[0484] When the organic EL element of the fifth embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in at least one of the one or more light-emitting layers.

[0485] (Content of Compounds in Emitting Layer) The contents of the first host material (first compound), the sensitizing material (second compound), and the fluorescent material (third compound) contained in the emitting layer are preferably within the following ranges, for example.

[0486] The content of the first host material (first compound) in the light-emitting layer is preferably 50% by mass or more, more preferably 70% by mass or more, and is preferably 95% by mass or less, more preferably 90% by mass or less.

[0487] When the sensitizing material (second compound) is a delayed fluorescent compound, the content of the delayed fluorescent compound in the light-emitting layer is preferably 5% by mass or more, more preferably 10% by mass or more, and is preferably 50% by mass or less, more preferably 30% by mass or less.

[0488] When the sensitizing material (second compound) is a phosphorescent metal complex, the content of the phosphorescent metal complex in the light-emitting layer is preferably 5% by mass or more, more preferably 10% by mass or more, and is preferably 50% by mass or less, more preferably 30% by mass or less.

[0489] The content of the fluorescent material (third compound) in the light-emitting layer is preferably 0.5% by mass or more, more preferably 1% by mass or more. The content of the fluorescent material (third compound) in the light-emitting layer is preferably 10% by mass or less, more preferably 5% by mass or less. The upper limit of the total content of the first host material (first compound), sensitizing material (second compound), and fluorescent material (third compound) in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the case where at least one layer of one or more light-emitting layers contains a material other than the first host material, sensitizing material, and fluorescent material. In the fourth embodiment, at least one layer of one or more light-emitting layers may contain only one type of first host material, sensitizing material, and fluorescent material, or two or more types of first host material, sensitizing material, and fluorescent material, respectively.

[0490] The organic EL element according to the fourth embodiment can have a longer life. According to one aspect of the organic EL element according to the fourth embodiment, the light-emitting layer contains a sensitizing material (preferably a blue-sensitizing material), a compound according to the first embodiment (first compound) as a first host material, and a fluorescent material (third compound), thereby improving the life of the organic EL element. The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0491] [Fifth Embodiment] The configuration of an organic EL element according to a fifth embodiment will be described. In the description of the fifth embodiment, the same components as those in the third and fourth embodiments will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the fifth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third and fourth embodiments can be used.

[0492] (Light-Emitting Layer) In the organic EL device according to the fifth embodiment, at least one of the one or more light-emitting layers further contains a fourth compound as a second host material. In one aspect of the organic EL device according to the fifth embodiment, at least one of the one or more light-emitting layers contains a first host material (first compound), a sensitizing material (second compound), a fluorescent material (third compound), and a fourth compound as a second host material. The first host material (first compound) and the second host material (fourth compound) are different from each other. The organic EL device according to the fifth embodiment is otherwise similar to the organic EL device according to the fourth embodiment. In the fifth embodiment, the first host material, the second host material, the sensitizing material, and the fluorescent material are different from each other. In one aspect of the fifth embodiment, at least one of the one or more light-emitting layers contains a first host material, a second host material, a delayed fluorescent compound as a sensitizing material, and a fluorescent material. In this aspect, it is preferable that at least one of the one or more light-emitting layers does not contain a phosphorescent metal complex. In one aspect of the fifth embodiment, at least one layer of the one or more emitting layers contains a first host material, a second host material, a phosphorescent metal complex as a sensitizing material, and a fluorescent material.

[0493] In the fifth embodiment, the first host material, the second host material, the sensitizing material, and the fluorescent material are contained in a single layer. For example, when the organic EL element has one light-emitting layer, the first host material, the second host material, the sensitizing material, and the fluorescent material are contained in the single light-emitting layer. When the organic EL element has multiple light-emitting layers, the first host material, the second host material, the sensitizing material, and the fluorescent material are contained in any one of the multiple light-emitting layers.

[0494] [First Host Material] In the fifth embodiment, the first host material is the compound according to the first embodiment (the compound represented by the formula (1)).

[0495] [Fluorescent Material] In the fifth embodiment, the fluorescent material may be the same as the fluorescent material (third compound) described in the third embodiment.

[0496] [Sensitizing Material] In the fifth embodiment, the phosphorescent metal complex serving as the sensitizing material may be the same material as the phosphorescent metal complex described in the third embodiment. In the fifth embodiment, the delayed fluorescent compound serving as the sensitizing material may be the same material as the delayed fluorescent compound described in the fourth embodiment.

[0497] [Second Host Material] In the fifth embodiment, the second host material is a fourth compound containing, in one molecule, one or more partial structures selected from the group consisting of partial structures represented by the following formulas (301) to (318):

[0498]

[0499]

[0500] (In the formula (301), A １１ ~A １６ are each independently a nitrogen atom, CR １１ or a carbon atom bonded to another atom or structure in the molecule of the fourth compound, １１ ~A １６ at least one of R is a carbon atom bonded to another atom or another structure in the molecule of the fourth compound; １１ If there are multiple R １１ are the same or different, and multiple R １１ one or more pairs of adjacent two or more of the following are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; and in the formula (302), １ ~A ４ are each independently a nitrogen atom, CR １２ or a carbon atom bonded to another atom or structure in the molecule of the fourth compound, １２ are each independently a hydrogen atom or a substituent, or an adjacent R １２ any one or more pairs of R are bonded to each other to form a ring, １２If there are multiple R １２ are the same or different, and multiple R １２ one or more pairs of adjacent two or more of X are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １０ is NR １３ , C(R １４ ) (R １５ ), Si(R １６ ) (R １７ ), an oxygen atom, a sulfur atom, a nitrogen atom bonded to another atom or another structure in the molecule of the fourth compound, R １８ and a carbon atom bonded to another atom or structure in the molecule of the fourth compound, or R １９ and a silicon atom bonded to another atom or another structure in the molecule of the fourth compound, １ ~A ４ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ At least one of the silicon atoms in R is bonded to another atom or another structure in the molecule of the fourth compound, １４ and R １５ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R １６ and R １７ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １１５ and R １１６ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and in the formulae (301) to (304), R１１ , R １２ , R １４ , R １５ , R １６ , R １７ , R １１５ and R １１６ , and R １３ , R １８ , R １９ and R １１７ are each independently a hydrogen atom-substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a group represented by —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -P(=O)(R ９１０ ) (R ９１１ ), a group represented by —P(═O)(OR ９１２ ) (OR ９１３ a group represented by —Ge(R ９１４ ) (R ９１５ ) (R ９１６ ), a group represented by —B(R ９１７ ) (R ９１８), a substituted or unsubstituted aralkyl group having 7 to 50 ring atoms, a halogen atom, a cyano group, a nitro group, 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, and in the formulas (303) to (318), * represents a bonding site to another atom or another structure in the molecule of the fourth compound, and when the fourth compound has a plurality of partial structures represented by the formulas (301) to (304), the plurality of partial structures represented by the formulas (301) are the same or different from each other, the plurality of partial structures represented by the formulas (302) are the same or different from each other, the plurality of partial structures represented by the formulas (303) are the same or different from each other, and the plurality of partial structures represented by the formula (304) are the same or different from each other.

[0501] (In the fourth compound, R ９０１ ~R ９１８ are each independently 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７are the same or different from each other, R ９０８ If there are multiple R ９０８ are the same or different from each other, R ９０９ If there are multiple R ９０９ are the same or different from each other, R ９１０ If there are multiple R ９１０ are the same or different from each other, R ９１１ If there are multiple R ９１１ are the same or different from each other, R ９１２ If there are multiple R ９１２ are the same or different from each other, R ９１３ If there are multiple R ９１３ are the same or different from each other, R ９１４ If there are multiple R ９１４ are the same or different from each other, R ９１５ If there are multiple R ９１５ are the same or different from each other, R ９１６ If there are multiple R ９１６ are the same or different from each other, R ９１７ If there are multiple R ９１７ are the same or different from each other, R ９１８ If there are multiple R ９１８ are the same or different from each other.)

[0502] In the formula (302), X １０ is "a nitrogen atom bonded to another atom or another structure in the molecule of the fourth compound", the formula (302) is represented by the following formula (302-1): １０ "R １８ and a carbon atom bonded to another atom or another structure in the molecule of the fourth compound, the formula (302) is represented by the following formula (302-2): １０ "R １９and a silicon atom bonded to another atom or another structure in the molecule of the fourth compound, the formula (302) is represented by the following formula (302-3). １ ~A ４ are each independently A in the formula (302). １ ~A ４ is synonymous with R １８ and R １９ are each independently R in the formula (302). １２ and * represents the point of attachment to another atom or other structure in the molecule of the fourth compound.

[0503]

[0504] In one embodiment, the second host material has at least one partial structure represented by formula (301). In one embodiment, the partial structure represented by formula (301) is at least one selected from the group consisting of partial structures represented by formulas (A11) to (A19) below.

[0505]

[0506]

[0507] (In the formulas (A11) to (A16), A １２ ~A １６ are each independently a nitrogen atom or CR １１ and R １１ is R in the formula (301). １１ and * represents a bonding site to another atom or another structure in the molecule of the fourth compound. In the formulae (A17) and (A18), A １１ ~A ２２ are each independently a nitrogen atom or CR １１ or a carbon atom bonded to another atom or structure in the molecule of the fourth compound, R １１ are each independently R in the formula (301). １１ is synonymous with A １１ ~A ２２at least one of A is a carbon atom bonded to another atom or another structure in the molecule of the fourth compound, １１ ~A １８ are each independently a nitrogen atom or CR １１ or a carbon atom bonded to another atom or structure in the molecule of the fourth compound, R １１ are each independently R in the formula (301). １１ is synonymous with X １１ and X １２ each independently represents X in the formula (302). １０ and A １１ ~A １８ Carbon atoms in X １１ and X １２ Nitrogen atom in X １１ and X １２ Carbon atoms in １１ and X １２ At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the fourth compound.

[0508] In one embodiment, the second host material has at least one partial structure represented by formula (302). In one embodiment, the partial structure represented by formula (302) is at least one selected from the group consisting of partial structures represented by formulas (B11) to (B24) below.

[0509]

[0510] (In the formulas (B11) to (B16), Ax １ ~Ax ４ are each independently a nitrogen atom or CR １２ and R １２ are each independently R in the formula (302). １２ is synonymous with X １０ is X in the formula (302). １０ * represents a bonding site to another atom or another structure in the molecule of the fourth compound, and in formula (B17), Ax １ , Ax２ and Ay １ ~Ay ４ are each independently a nitrogen atom or CR １２ or a carbon atom bonded to another atom or structure in the molecule of the fourth compound, R １２ are each independently R in the formula (302). １２ is synonymous with X １０ is X in the formula (302). １０ where Ax １ , Ax ２ and Ay １ ~Ay ４ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ At least one of the silicon atoms in the formula (B18) is bonded to another atom or another structure in the molecule of the fourth compound, １ ~Ay ８ are each independently a nitrogen atom or CR １２ or a carbon atom bonded to another atom or structure in the molecule of the fourth compound, R １２ are each independently R in the formula (302). １２ is synonymous with X １０ is X in the formula (302). １０ and Ay １ ~Ay ８ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the fourth compound.

[0511]

[0512] (In the formulas (B19) to (B24), Ay １ ~Ay ８ and Ay ９ ~Ay １２ are each independently a nitrogen atom or CR １２or a carbon atom bonded to another atom or structure in the molecule of the fourth compound, R １２ are each independently R in the formula (302). １２ is synonymous with X ９ and X １０ each independently represents X in the formula (302). １０ Ay is synonymous with １ ~Ay ８ and Ay ９ ~Ay １２ Carbon atoms in X ９ and X １０ Nitrogen atom in X ９ and X １０ Carbon atoms in ９ and X １０ At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the fourth compound.

[0513] In the fourth compound of the fifth embodiment, R １１、 R １２ and R １１５ ~R １１７ are each independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, an amino group, an unsubstituted alkylamino group having 2 to 30 carbon atoms, an unsubstituted arylamino group having 6 to 60 ring carbon atoms, a thiol group, an unsubstituted alkylthio group having 1 to 30 carbon atoms, or an unsubstituted arylthio group having 6 to 30 ring carbon atoms. １１、 R １２ and R １１５ ~R １１７are each independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an amino group, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted arylamino group having 6 to 60 ring carbon atoms, a thiol group, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms. １１、 R １２ and R １１５ ~R １１７ is more preferably a hydrogen atom.

[0514] In the fourth compound of the fifth embodiment, X １０ R in １３ ~R １９ , and X ９ R in １３ ~R １９ (X １０ R in １３ ~R １９ and the same meaning as above) are preferably each independently a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms. １０ R in １３ ~R １９ , and X ９ R in １３ ~R １９ are each independently a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms. １０ R in１３ ~R １９ , and X ９ R in １３ ~R １９ and are each independently an unsubstituted aryl group having 6 to 14 ring carbon atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0515] Examples of the partial structure represented by any one of the formulas (301) to (318) include partial structures represented by the following formulas (A101) to (A121) and (B101) to (B125). It is also preferable that the fourth compound contains at least one of the partial structures represented by the following formulas (A101) to (A121) and (B101) to (B125) in one molecule.

[0516]

[0517] In the formulae (A101) to (A107), R １０１ ~R １０６ are each independently R in the formula (301). １１ is synonymous with R １０１ ~R １０６ At least one of the R １０１ and R １０２ Group R １０２ and R １０３ Group R １０３ and R １０４ Group R １０４ and R １０５ Group R １０５ and R １０６ and R １０６ and R １０１ one or more of the pairs of may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other.

[0518]

[0519] In the formulae (A108) and (A109), R １１０ are each independently R in the formula (301).１１ is synonymous with R １１０ At least one of R is a single bond bonding to another atom or another structure in the molecule of the fourth compound, １１０ are the same or different, and multiple R １１０ one or more pairs of adjacent two or more of these are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0520]

[0521] In the formulae (A110) to (A114), R １１０ and R １１２ ~R １１４ are each independently R in the formula (301). １１ is synonymous with X １１０ each independently represents X in the formula (302). １０ where R １１０ and R １１２ ~R １１４ At least one of X is a single bond bonding to another atom or another structure in the molecule of the fourth compound, or １１０ At least one of the nitrogen atom, carbon atom, and silicon atom in the fourth compound is bonded to another atom or another structure in the molecule of the fourth compound, and a plurality of R １１０ In the formulae (A110) to (A114), a plurality of R １１０ a set of two or more adjacent １１２ and R １１３ and X １１０ R in １４ and R １５ The set (X １０ R in １４ and R １５ (same as the set of X) １１０ R in １６ and R １７ The set (X １０ R in １６ and R １７one or more pairs of (same meaning as a pair of) are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0522]

[0523] In the formulae (A115) to (A119), R １１０ and R １１２ ~R １１４ are each independently R in the formula (301). １１ where R １１０ and R １１２ ~R １１４ At least one of R is a single bond bonding to another atom or another structure in the molecule of the fourth compound, １１０ In the formulae (A115) to (A119), a plurality of R １１０ and R １１２ and R １１３ One or more of the pairs of may be bonded to each other to form a substituted or unsubstituted monocyclic ring, a substituted or unsubstituted fused ring, or are not bonded to each other.

[0524]

[0525] In the formulae (A120) and (A121), R １１０ are each independently R in the formula (301). １１ where R １１０ At least one of R is a single bond bonding to another atom or another structure in the molecule of the fourth compound, １１０ In the formulae (A120) to (A121), a plurality of R １１０ one or more pairs of adjacent two or more of these are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0526]

[0527] In the formulae (B101) to (B109), R １１４ and R １２１ ~R １３１ are each independently R in the formula (302). １２ where R １１４ and R １２１ ~R １３１ At least one of R is a single bond bonding to another atom or another structure in the molecule of the fourth compound. １２２ and R １２３ Group R １２３ and R １１４ and R １１４ and R １２１ In the formulae (B105) and (B106), one or more of the pairs of R are bonded to each other to form a substituted or unsubstituted monocycle, or to form a substituted or unsubstituted fused ring, or are not bonded to each other. １２４ and R １２５ Group R １２５ and R １２６ Group R １２６ and R １２７ Group R １２７ and R １２８ and R １２８ and R １２９ In the formula (B107), one or more of the pairs of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring, or are not bonded to each other. １２４ and R １２５ Group R １２５ and R １２６ Group R １２６ and R １２７ Group R １２７ and R １２８ Group R １２８ and R １２９ Group R １２９ and R １１４ and R １１４ and R １２４In the formulae (B108) and (B109), one or more of the pairs of R are bonded to each other to form a substituted or unsubstituted monocycle, or to form a substituted or unsubstituted fused ring, or are not bonded to each other. １２４ and R １２５ Group R １２５ and R １２６ Group R １３０ and R １３１ and R １３１ and R １２９ one or more of the pairs of may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other.

[0528]

[0529] In the formulae (B110) to (B117), R １１０ and R １３２ ~R １３５ are each independently R in the formula (302). １２ where R １１０ and R １３２ ~R １３５ At least one of R is a single bond bonding to another atom or another structure in the molecule of the fourth compound, １１０ In the formulae (B110) to (B117), a plurality of R １１０ and R １３２ and R １３３ one or more of the pairs of may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other.

[0530]

[0531] In the formulae (B118) to (B123), R １１０ are each independently R in the formula (302). １２ Xa and Xb each independently represent X in the formula (302). １０ where R １１０At least one of the nitrogen atoms, carbon atoms, and silicon atoms in Xa and Xb are single bonds bonding to other atoms or other structures in the molecule of the fourth compound, or at least one of the nitrogen atoms, carbon atoms, and silicon atoms in Xa and Xb are single bonds bonding to other atoms or other structures in the molecule of the fourth compound, and a plurality of R １１０ In the formulae (B118) to (B123), a plurality of R １１０ a pair of adjacent two or more of R in Xa １４ and R １５ and R in Xb １４ and R １５ The set (X １０ R in １４ and R １５ (same meaning as the set of Xa) and R １６ and R １７ and R in Xb １６ and R １７ The set (X １０ R in １６ and R １７ one or more pairs of (same meaning as a pair of) are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0532]

[0533] In the formulae (B124) and (B125), R １１０ are each independently R in the formula (302). １２ Xa, Xb, and Xc each independently represent X in the formula (302). １０ where R １１０ At least one of the nitrogen atoms, carbon atoms, and silicon atoms in Xa, Xb, and Xc are single bonds bonding to other atoms or other structures in the molecule of the fourth compound, or at least one of the nitrogen atoms, carbon atoms, and silicon atoms in Xa, Xb, and Xc are single bonds bonding to other atoms or other structures in the molecule of the fourth compound, and a plurality of R １１０ In the formulae (B124) and (B125), a plurality of R １１０and R in Xa, Xb, and Xc. １４ and R １５ The set (X １０ R in １４ and R １５ (same meaning as a set of Xa, Xb and Xc) and R １６ and R １７ The set (X １０ Oke R １６ and R １７ one or more pairs of (same meaning as a pair of) are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0534] In the formulae (A101) to (A121) and (B101) to (B125), R １１０ , R １０１ ~R １０６ , R １１２ ~R １１４ , R １２１ ~R １３１ and R １３２ ~R １３５ are each independently preferably a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms; and even more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0535] In the formulae (A101) to (A121) and (B101) to (B125), Xa, Xb, Xc and X １１０ R in １３ ~R １９ (X １０ R in １３ ~R １９and the like) are each independently preferably a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms; and even more preferably an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0536] In the fifth embodiment, the fourth compound preferably has at least one of (I) a cyano group, an amino group, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, or (II) a monovalent or higher residue derived from any of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted indole, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrazine, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted phenanthrene, and substituted or unsubstituted triphenylene.

[0537] In the fifth embodiment, it is more preferable that the fourth compound has (III) at least one cyano group, or (IV) at least one monovalent or higher residue derived from any of substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triphenylene.

[0538] In the fifth embodiment, it is more preferable that the fourth compound has at least one monovalent or higher residue derived from any one of substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triazine, and substituted or unsubstituted pyrimidine.

[0539] In the fifth embodiment, the fourth compound preferably has at least one monovalent or higher valent residue derived from a substituted or unsubstituted carbazole.

[0540] In the fifth embodiment, the fourth compound preferably has at least one partial structure represented by the following formula (15):

[0541]

[0542] (In the formula (15), R １５０ ~R １５８ At least one of R is a single bond bonding to another atom or another structure in the molecule of the fourth compound, and R is not a single bond. １５０ ~R １５８ are each independently a hydrogen atom-substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a group represented by —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -P(=O)(R ９１０ ) (R ９１１ a group represented by —Ge(R ９１２ ) (R ９１３ ) (R ９１４ ), a group represented by —B(R ９１５ ) (R ９１６ ) a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, 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.

[0543] In the formula (15), R １５０ is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and even more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0544] (Fourth Compound Represented by Formula (161) or (162)) In the fifth embodiment, the fourth compound is also preferably a compound represented by the following formula (161) or (162).

[0545]

[0546] (In the formula (161), Ar １６１is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, m1 is 1, 2, 3, 4, 5 or 6, R １６１ is an electron donating group, R １６１ are respectively Ar １６１ When m1 is 2 or more, a plurality of R １６１ are the same or different, provided that Ar １６１ is not an electron-accepting aromatic hydrocarbon ring or heterocycle, but Ar １６１ When Ar has a substituent, the substituent is not an electron accepting group, and １６２ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, n1 is 1, 2, 3, 4, 5 or 6, R １６２ is an electron accepting group, and R １６２ are respectively Ar １６２ When n1 is 2 or more, a plurality of R １６２ are the same or different, provided that Ar １６２ is not an electron-donating aromatic hydrocarbon ring or heterocyclic ring, but Ar １６２ When has a substituent, the substituent is not an electron-donating group.

[0547] In the formulas (161) and (162), Ar １６１ and Ar １６２ are each preferably independently a monovalent or higher valent residue derived from a compound represented by the following formula (A61) or (A62).

[0548]

[0549] In the fifth embodiment, R in the formula (161) １６１ are each independently a monovalent or higher valent residue derived from any of the compounds represented by the following formulae (DN1) to (DN6) and (DN8) to (DN10), or a group represented by the following formula (DN7):

[0550]

[0551] (In the formula (DN7), * represents Ar １６１ It represents the bonding site with the elements that make up the molecule.)

[0552] In the fifth embodiment, R in the formula (162) １６２ are preferably each independently a monovalent or higher valent residue derived from any of the compounds represented by the following formulae (AC4) to (AC18) and (AC22) to (AC23), or any of the groups represented by the following formulae (AC1) to (AC3), (AC19) to (AC21), and (AC24).

[0553]

[0554]

[0555] (In the formula (AC1), n Ａ is 1, 2 or 3, and in the formulae (AC22) and (AC23), X １ ~X ８ are each independently CR １６３ or a carbon atom bonded to another atom or structure in the molecule of the fourth compound, with the proviso that X １ ~X ８ At least one of the carbon atoms in １６２ In the formula (AC24), X １ ~X ８ are each independently a nitrogen atom or CR １６３ or Ar １６２ In the formulae (AC22) to (AC24), R １６３ If there are multiple R １６３ are the same or different, and multiple R １６３one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring １６３ are each independently R in the formula (302). １２ In the formulae (AC1) to (AC3), (AC19) to (AC21) and (AC24), * represents Ar １６２ It represents the bonding site with the elements that make up the molecule.)

[0556] In the fifth embodiment, the fourth compound is also preferably a compound represented by the following formula (130):

[0557]

[0558] (In the formula (130), X １３ is an oxygen atom, a sulfur atom, or a group represented by N—Rb, １ ~Z １２ are each independently a nitrogen atom or a group represented by C—Rc, １４ and Ar １５ are each independently 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; １４ and L １５ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; Rb and Rc each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —C(═O)R ９０８a group represented by -COOR ９０９ a group represented by -P(=O)(R ９１０ ) (R ９１１ a group represented by —Ge(R ９１２ ) (R ９１３ ) (R ９１４ ) a cyano group, a nitro group, 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, and when there are multiple Rc's, the multiple Rc's are the same or different.

[0559] In the compound represented by the formula (130), -L １４ -Ar １４ and a group represented by -L １５ -Ar １５ and the group represented by １ and Z １２ , Z ２ and Z １１ , Z ３ and Z １０ , Z ４ and Z ９ , Z ５ and Z ８ , and Z ６ and Z ７ In this case, it is also preferable that all of X are not the same group. １３ and a structure fused to the right side of a five-membered ring containing X １３ The compound represented by formula (130) is a compound having an asymmetric structure, unlike the structure in which the compound is fused to the left side of a five-membered ring containing the following:

[0560] In the compound represented by the formula (130), -L １４ -Ar １４ and a group represented by -L １５ -Ar １５ In this case, as in the above, the compound represented by the formula (130) is a compound having an asymmetric structure.

[0561] In the fifth embodiment, it is also preferable that the fourth compound is a compound represented by the following formula (120):

[0562]

[0563] (In the formula (120), Ar １１ and Ar １２ are each independently 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; １１ and L １２ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; １３ is a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring atoms, m is 0, 1, 2, or 3, and a plurality of L １３ are the same or different from each other, and X １ ~X ８ and Y １ ~Y ８ are each independently N or CRa, provided that X ５ ~X ８ One of them and Y １ ~Y ４ One of them is L １３ Each Ra is independently a hydrogen atom-substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), a halogen atom, 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, and when a plurality of Ra's are present, the plurality of Ra's are the same or different from one another, and the compound represented by the formula (120) satisfies one or both of the following (i) and (ii): (i) Ar １１ and Ar １２At least one of (ii) X is an aryl group substituted with a cyano group and having 6 to 50 ring carbon atoms, or a heterocyclic group substituted with a cyano group and having 5 to 50 ring atoms. １ ~X ４ and Y ５ ~Y ８ At least one of is CRa, and X １ ~X ４ and Y ５ ~Y ８ wherein at least one of Ra is an aryl group substituted with a cyano group and having 6 to 50 ring carbon atoms, or a heterocyclic group substituted with a cyano group and having 5 to 50 ring atoms.

[0564] In the compound represented by the formula (120), the aromatic hydrocarbon group having 6 to 50 ring carbon atoms and substituted with a cyano group, and the heterocyclic group having 5 to 50 ring atoms and substituted with a cyano group may further have a substituent other than a cyano group.

[0565] In the compound represented by the formula (120), m is preferably 0, 1 or 2, and more preferably 0 or 1. In the compound represented by the formula (120), when m is 0, X ５ ~X ８ One of them and Y １ ~Y ４ is directly bonded to one of the groups via a single bond.

[0566] In the compound represented by the formula (120), X ６ and Y ３ Pair with X ６ and Y ２ Pairs with and X ７ and Y ３ Any pair selected from the group consisting of pairs of １３ It is preferable that the carbon atom is bonded via a carbon atom bonded directly to the carbon atom.

[0567] X ６ and Y ３ The pair with L １３ When the carbon atom is bonded via an intervening group or is bonded directly, the compound represented by formula (120) is represented by formula (121) below.

[0568]

[0569] (In the formula (121), Ar １１ , Ar １２ , L １１ , L １２ , L １３ , m, X １ ~X ５ , X ７ ~X ８ , Y １ ~Y ２ and Y ４ ~Y ８ respectively represent Ar in the formula (120). １１ , Ar １２ , L １１ , L １２ , L １３ , m, X １ ~X ５ , X ７ ~X ８ , Y １ ~Y ２ and Y ４ ~Y ８ and the compound represented by the formula (121) satisfies at least one of the conditions (i) and (ii).

[0570] In the compound represented by the formula (120), -Ar １１ -L １１ and a group represented by -Ar １２ -L １２ and the groups represented by the following formula (I) are preferably different from each other.

[0571] L １３ The monocyclic hydrocarbon group having 6 or less ring carbon atoms as L is preferably at least one group selected from the group consisting of a phenylene group, a cyclopentenylene group, a cyclopentadienylene group, a cyclohexylene group, and a cyclopentylene group, and more preferably a phenylene group. １３ The monocyclic heterocyclic group having 6 or less ring atoms as represented by is preferably at least one group selected from the group consisting of a pyrrolylene group, a pyrazinylene group, a pyridinylene group, a furylene group, and a thiophenylene group.

[0572] In one embodiment, at least one of the one or more light-emitting layers may contain two or more fourth compounds having different molecular structures. By mixing compounds with different charge-transporting properties, the charge balance in the light-emitting layer is improved, and the light-emitting efficiency is expected to be improved. Furthermore, by forming an exciplex between the two or more fourth compounds (second host materials), the excitation energy is reduced, enabling lower-voltage operation than when the light-emitting layer contains only one second host material.

[0573] (Method for Producing Second Host Material) The second host material as the fourth compound can be produced by a known method. The fourth compound can also be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0574] (Specific Examples of Second Host Material) Specific examples of the second host material as the fourth compound of the fifth embodiment include the following compounds, however, the present invention is not limited to these specific examples of compounds.

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583]

[0584]

[0585]

[0586]

[0587]

[0588]

[0589]

[0590]

[0591]

[0592]

[0593]

[0594]

[0595]

[0596]

[0597]

[0598]

[0599]

[0600]

[0601]

[0602]

[0603]

[0604]

[0605] (Relationship between the first host material, the second host material, the sensitizing material, and the fluorescent material in the emitting layer) In one aspect of the fifth embodiment, the sensitizing material is a delayed fluorescent compound. In one aspect of the fifth embodiment, at least one layer of the one or more emitting layers contains a delayed fluorescent compound as a sensitizing material, but may not contain a phosphorescent metal complex.

[0606] In one aspect of the fifth embodiment, it is preferable that at least one layer of the one or more light-emitting layers satisfies at least any one of the relationships of the mathematical formula (4), the mathematical formula (4A), the mathematical formula (4B), the mathematical formula (6), the mathematical formula (6A), and the mathematical formula (6B) in the fourth embodiment. １ (H2) and the lowest excited singlet energy S of the delayed fluorescent compound １ (GT2) preferably satisfy the relationship of the following formula (Formula 41A): １ (H2)>S １ (GT2) ... (Number 41A)

[0607] In one embodiment, the lowest excited singlet energy S of the second host material, the delayed fluorescent compound, and the fluorescent material １ It is preferable that S satisfies the relationship of the following formula (Formula 41B). １ (H2)>S １ (GT2)>S １ (D) ...(Number 41B)

[0608] In one embodiment, when the sensitizing material is a delayed fluorescent compound, the energy gap T at 77 [K] of the second host material is ７７Ｋ (H2), and the energy gap T at 77 [K] of the delayed fluorescent compound ７７Ｋ It is preferable that (GT2) satisfies the relationship of the following formula (Formula 61): T ７７Ｋ (H2)>T ７７Ｋ (GT2) ... (Number 61)

[0609] In one embodiment, the second host material, the delayed fluorescent compound, and the fluorescent material have an energy gap T at 77 [K]. ７７Ｋ It is preferable that T satisfies the relationship of the following formula (Formula 61B). ７７Ｋ (H2)>T ７７Ｋ (GT2)>T ７７Ｋ (D) ...(Number 61B)

[0610] In one aspect of the fifth embodiment, the sensitizing material is a phosphorescent metal complex. In one aspect of the fifth embodiment, at least one of the one or more emitting layers may contain a phosphorescent metal complex as a sensitizing material, but may not contain a delayed fluorescent compound.

[0611] 6 shows an example of the relationship between the energy levels of a first host material (first compound), a second host material (fourth compound), a phosphorescent metal complex (second compound) as a sensitizing material, and a fluorescent material (third compound) in an emitting layer. In FIG. 6 , S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first host material, and T1(M1) represents the lowest excited triplet state of the first host material. S1(M4) represents the lowest excited singlet state of the second host material, and T1(M4) represents the lowest excited triplet state of the second host material. S1(M2) represents the lowest excited singlet state of the phosphorescent metal complex, and T1(M2) represents the lowest excited triplet state of the phosphorescent metal complex. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from T1(M2) to S1(M3) in FIG. 6 represents dipole-type energy transfer from the lowest excited triplet state of the phosphorescent metal complex to the lowest excited singlet state of the fluorescent material. As shown in FIG. 6 , when a phosphorescent metal complex is used as a sensitizer, the lowest excited singlet state S1(M2) of the phosphorescent metal complex can undergo intersystem crossing to the lowest excited triplet state T1(M2) due to spin-orbit interactions and heavy atom effects. Dipole-type energy transfer then occurs from the lowest excited triplet state T1(M2) of the phosphorescent metal complex to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing this mechanism, the internal quantum efficiency can theoretically be increased to 100%. Note that the magnitude relationship between the energy levels of S1(M1) and S1(M4) and the magnitude relationship between the energy levels of T1(M1) and T1(M4) are not limited to those shown in FIG.

[0612] In one aspect of the fifth embodiment, it is preferable that at least one layer of the one or more light-emitting layers satisfies at least any one of the relationships of the mathematical formula (3), the mathematical formula (3A), the mathematical formula (3B), the mathematical formula (3C), the mathematical formula (5), the mathematical formula (5A), and the mathematical formula (5B).

[0613] In one embodiment, when the sensitizing material is a phosphorescent metal complex, the energy gap T at 77 [K] of the second host material is ７７Ｋ (H2), and the energy gap T of the phosphorescent metal complex at 77 [K] ７７Ｋ (GP2) is expressed by the following formula (Formula 31A): T ７７Ｋ (H2)>T ７７Ｋ (GP2) ... (Number 31A)

[0614] In one embodiment, the energy gap T at 77 [K] of the second host material and the phosphorescent metal complex ７７Ｋ and the lowest excited singlet energy S of the fluorescent material. １ It is preferable that (D) and T satisfy the relationship of the following formula (Formula 31B). ７７Ｋ (H2)>T ７７Ｋ (GP2)>S １ (D) ...(Number 31B)

[0615] In one embodiment, the lowest excited singlet energy S of the second host material １ (H2) and the lowest excited singlet energy S of the phosphorescent metal complex １ It is also preferable that (GP2) satisfies the relationship of the following formula (Formula 51): S １ (H2)>S １ (GP2) ... (Equation 51)

[0616] In one embodiment, the lowest excited singlet energy S of the second host material, the phosphorescent metal complex, and the fluorescent material １ It is also preferable that S satisfies the relationship of the following formula (Formula 51B): １ (H2)>S １ (GP2)>S １ (D) ...(Number 51B)

[0617] When the organic EL element of the fifth embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in at least one of the one or more light-emitting layers.

[0618] (Contents of Compounds in Emitting Layer) The contents of the first host material (first compound), second host material (fourth compound), sensitizing material (second compound), and fluorescent material (third compound) contained in the emitting layer are preferably within the following ranges, for example.

[0619] The total content of the first host material and the second host material in the light-emitting layer is preferably 70% by mass or more, more preferably 80% by mass or more, and is preferably 90% by mass or less, more preferably 85% by mass or less.

[0620] When the sensitizing material (second compound) is a delayed fluorescent compound, the content of the delayed fluorescent compound in the light-emitting layer is preferably 5% by mass or more, more preferably 10% by mass or more, and is preferably 50% by mass or less, more preferably 30% by mass or less.

[0621] When the sensitizing material (second compound) is a phosphorescent metal complex, the content of the phosphorescent metal complex in the light-emitting layer is preferably 5% by mass or more, more preferably 10% by mass or more, and is preferably 50% by mass or less, more preferably 30% by mass or less.

[0622] The content of the fluorescent material (third compound) in the light-emitting layer is preferably 0.5% by mass or more, more preferably 1% by mass or more. The content of the fluorescent material (third compound) in the light-emitting layer is preferably 10% by mass or less, more preferably 5% by mass or less. The upper limit of the total content of the first host material (first compound), second host material (fourth compound), sensitizing material (second compound), and fluorescent material (third compound) in the light-emitting layer is 100% by mass. Note that the fifth embodiment does not exclude the inclusion of materials other than the first host material, second host material, sensitizing material, and fluorescent material in the light-emitting layer. In the fifth embodiment, the light-emitting layer may contain only one type of the first host material, second host material, sensitizing material, and fluorescent material, or two or more types of each.

[0623] The organic EL element according to the fifth embodiment can have a longer life. According to one aspect of the organic EL element according to the fifth embodiment, the light-emitting layer contains a sensitizing material (preferably a blue-sensitizing material), a compound according to the first embodiment (first compound) as a first host material, a second host material (fourth compound), and a fluorescent material (third compound), thereby improving the life of the organic EL element. The organic EL element according to the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0624] [Sixth Embodiment] The configuration of an organic EL element according to a sixth embodiment will be described. In the description of the sixth embodiment, the same components as those in the third to fifth embodiments will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the sixth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third to fifth embodiments can be used.

[0625] (Light-emitting layer) In the sixth embodiment, the compound according to the first embodiment (first compound) used as the first host material in the organic EL element according to the third embodiment is used as a sensitizing material. The sixth embodiment is otherwise similar to the organic EL element according to the third embodiment. In the sixth embodiment, at least one layer of one or more light-emitting layers contains the compound according to the first embodiment (first compound) as a sensitizing material and a fluorescent material. In the sixth embodiment, the sensitizing material and the fluorescent material are different materials. In one aspect of the sixth embodiment, the sensitizing material is a delayed fluorescent compound. In this aspect, at least one layer of one or more light-emitting layers does not contain a phosphorescent metal complex.

[0626] [Sensitizing Material] In the sixth embodiment, the sensitizing material is the compound (first compound) according to the first embodiment. In the sixth embodiment, when the sensitizing material is a delayed fluorescent compound, a compound having delayed fluorescence (for example, a compound having a donor moiety and an acceptor moiety bonded to each other in the molecule) among the compounds according to the first embodiment can be selected and used as the delayed fluorescent compound.

[0627] [Fluorescent Material] In the sixth embodiment, the fluorescent material may be the same as the fluorescent material (third compound) described in the third embodiment.

[0628] (Relationship between Sensitizing Material and Fluorescent Material in Emitting Layer) In one aspect of the sixth embodiment, the sensitizing material (first compound) is a delayed fluorescent compound. In one aspect of the sixth embodiment, at least one of the one or more emitting layers may contain a delayed fluorescent compound as a sensitizing material, but may not contain a phosphorescent metal complex.

[0629] 7 is a diagram showing an example of the relationship between the energy levels of a delayed fluorescent compound as a sensitizing material (first compound) and a fluorescent material (third compound) when the emitting layer contains the delayed fluorescent compound as a sensitizing material (first compound). In FIG. 7, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the delayed fluorescent compound, and T1(M1) represents the lowest excited triplet state of the delayed fluorescent compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from S1(M1) to S1(M3) in FIG. 7 represents Förster energy transfer from the lowest excited singlet state of the delayed fluorescent compound to the lowest excited singlet state of the fluorescent material. As shown in Figure 7, when a compound with a small ΔST (M1) is used as the delayed fluorescent compound, the lowest excited triplet state T1 (M1) can undergo reverse intersystem crossing to the lowest excited singlet state S1 (M1) due to thermal energy. Then, Förster energy transfer occurs from the lowest excited singlet state S1 (M1) of the delayed fluorescent compound to the fluorescent material, generating the lowest excited singlet state S1 (M3). As a result, fluorescence emission from the lowest excited singlet state S1 (M3) of the fluorescent material can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0630] In the sixth embodiment, when the sensitizing material is a delayed fluorescent compound, the lowest excited singlet energy S １ (GT1) and the lowest excited singlet energy S of the fluorescent material １ It is preferable that (D) satisfies the relationship of the following mathematical formula (Mathematical Formula 41): S １ (GT1)>S １ (D) ... (Equation 41)

[0631] In the sixth embodiment, when the sensitizing material is a delayed fluorescent compound, the energy gap T ７７Ｋ (GT1) and the energy gap T of the fluorescent material at 77 [K] ７７Ｋ It is also preferable that (D) satisfies the relationship of the following formula (Formula 61A): T７７Ｋ (GT1)>T ７７Ｋ (D) ...(Number 61A)

[0632] When the organic EL element of the sixth embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in at least one of the one or more light-emitting layers.

[0633] (Compound Content in Light-Emitting Layer) The contents of the sensitizing material (first compound) and the fluorescent material (third compound) contained in at least one of the one or more light-emitting layers are preferably within the following ranges, for example. The content of the sensitizing material (first compound) is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of the sensitizing material may be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99.9% by mass or less, or even 99% by mass or more and 99.9% by mass or less. The content of the fluorescent material (third compound) is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. Note that the sixth embodiment does not exclude the case where at least one of the one or more light-emitting layers contains a material other than the sensitizing material and the fluorescent material. At least one of the one or more light-emitting layers may contain only one type of sensitizing material or two or more types of fluorescent materials.

[0634] The organic EL element according to the sixth embodiment can improve the performance of the organic EL element, and can be used in electronic devices such as display devices and light-emitting devices.

[0635] [Seventh Embodiment] The configuration of an organic EL element according to a seventh embodiment will be described. In the description of the seventh embodiment, the same components as those in the third to sixth embodiments will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the seventh embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third to sixth embodiments can be used.

[0636] (Light-emitting layer) In the seventh embodiment, as in the sixth embodiment, the compound according to the first embodiment (first compound) is used as a sensitizing material. In the organic EL device according to the seventh embodiment, at least one of the one or more light-emitting layers contains the compound according to the first embodiment (first compound) as a sensitizing material, a fluorescent material, and a second host material different from the first compound. Other aspects are the same as those of the organic EL device according to the sixth embodiment. In the seventh embodiment, the second host material, the sensitizing material, and the fluorescent material are different from one another. In one aspect of the seventh embodiment, at least one of the one or more light-emitting layers contains a second host material (fourth compound), a delayed fluorescent compound as a sensitizing material (first compound), and a fluorescent material (third compound). In this aspect, at least one of the one or more light-emitting layers does not contain a phosphorescent metal complex.

[0637] [Second Host Material] In the seventh embodiment, the second host material may be the same as the second host material described in the fifth embodiment.

[0638] [Sensitizing Material] In the seventh embodiment, the same sensitizing material as the sensitizing material described in the sixth embodiment can be used.

[0639] [Fluorescent Material] In the seventh embodiment, the fluorescent material may be the same as the fluorescent material (third compound) described in the third embodiment.

[0640] (Relationship between the second host material, the sensitizing material, and the fluorescent material in the emitting layer) In one aspect of the seventh embodiment, the sensitizing material (first compound) is a delayed fluorescent compound. In one aspect of the seventh embodiment, at least one layer of the one or more emitting layers contains a delayed fluorescent compound as a sensitizing material, but may not contain a phosphorescent metal complex.

[0641] 8 is a diagram showing an example of the relationship between the energy levels of a second host material (fourth compound), a delayed fluorescent compound as a sensitizer material (first compound), and a fluorescent material (third compound) when the emitting layer contains the second host material (fourth compound), and the fluorescent material (third compound). In FIG. 8, S0 represents the ground state. S1(M4) represents the lowest excited singlet state of the second host material, and T1(M4) represents the lowest excited triplet state of the second host material. S1(M1) represents the lowest excited singlet state of the delayed fluorescent compound, and T1(M1) represents the lowest excited triplet state of the delayed fluorescent compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from S1(M1) to S1(M3) in FIG. 8 represents Förster energy transfer from the lowest excited singlet state of the delayed fluorescent compound to the lowest excited singlet state of the fluorescent material. As shown in FIG. 8, when a compound with a small ΔST(M1) is used as the delayed fluorescent compound, the lowest excited triplet state T1(M1) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M1) due to thermal energy. Then, Förster energy transfer occurs from the lowest excited singlet state S1(M1) of the delayed fluorescent compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that the use of delayed fluorescence due to this TADF mechanism can theoretically increase the internal quantum efficiency to 100%.

[0642] In one aspect of the seventh embodiment, it is preferable that at least one layer of the one or more light-emitting layers satisfies at least one of the relationships of the above-mentioned formula (41) and the above-mentioned formula (61A).

[0643] In the seventh embodiment, when the sensitizing material is a delayed fluorescent compound, the energy gap T ７７Ｋ (H2) and the energy gap T at 77 [K] of the delayed fluorescent compound ７７Ｋ It is preferable that (GT1) and T satisfy the relationship of the following formula (Formula 11). ７７Ｋ (H2)>T ７７Ｋ (GT1) ... (Equation 11)

[0644] In the seventh embodiment, when the sensitizing material is a delayed fluorescent compound, the lowest excited singlet energy S １ (H2) and the lowest excited singlet energy S of the delayed fluorescent compound １ It is also preferable that (GT1) satisfies the relationship of the following formula (Formula 42A): S １ (H2)>S １ (GT1) ... (Number 42A)

[0645] In the seventh embodiment, when the sensitizing material is a delayed fluorescent compound, the lowest excited singlet energy S １ It is also preferable that S satisfies the relationship of the following formula (Formula 42B): １ (H2)>S １ (GT1)>S １ (D) ...(Number 42B)

[0646] In the seventh embodiment, when the sensitizing material is a delayed fluorescent compound, the energy gap T ７７Ｋ It is also preferable that T satisfies the relationship of the following formula (Formula 62B): ７７Ｋ (H2)>T ７７Ｋ (GT1)>T ７７Ｋ (D) ...(Number 62B)

[0647] (Contents of Compounds in Emitting Layer) In the seventh embodiment, the contents of the second host material (fourth compound), the sensitizing material (first compound), and the fluorescent material (third compound) contained in at least one layer of the one or more emitting layers are preferably in the same ranges as the contents of the first host material, the delayed fluorescent compound (second compound) as a sensitizing material, and the fluorescent material (third compound) contained in at least one layer of the one or more emitting layers in the fourth embodiment, respectively.

[0648] The organic EL element according to the seventh embodiment can improve the performance of the organic EL element, and can be used in electronic devices such as display devices and light-emitting devices.

[0649] Eighth Embodiment (Electronic Device) An electronic device according to an eighth embodiment is equipped with the organic EL element according to any one of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lighting fixtures. The light-emitting device can be used in a display device, for example, as a backlight for a display device.

[0650] The display device as an electronic device according to the eighth embodiment is preferably an organic EL display device having organic EL elements as red, green, and blue pixels, and the blue pixels are preferably at least one of the organic EL elements according to the third, fourth, fifth, sixth, and seventh embodiments and the modified examples described below.

[0651] [Modifications of the Embodiment] The present invention is not limited to the above-described embodiment, and any modifications and improvements that can achieve the object of the present invention are included in the present invention.

[0652] For example, the number of light-emitting layers is not limited to one, and multiple light-emitting layers may be stacked. When the organic EL element has multiple light-emitting layers, it is sufficient that at least one light-emitting layer satisfies the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has multiple light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem organic EL element in which multiple light-emitting units are stacked via an intermediate layer.

[0653] Furthermore, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The barrier layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a barrier layer is disposed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and blocks holes from reaching a layer (e.g., an electron transport layer) closer to the cathode than the barrier layer. When the organic EL device includes an electron transport layer, the barrier layer is preferably provided between the light-emitting layer and the electron transport layer. When a barrier layer is disposed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and blocks electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the barrier layer. When the organic EL device includes a hole transport layer, the barrier layer is preferably provided between the light-emitting layer and the hole transport layer. Furthermore, the barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. The blocking layer prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the blocking layer (for example, the electron transport layer and the hole transport layer).The light-emitting layer and the blocking layer are preferably in contact with each other.

[0654] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope of achieving the object of the present invention.

[0655] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0656] <Compounds> The structures of the compounds represented by formula (1) used in the production of the organic EL devices according to Examples 1 to 9 are shown below.

[0657]

[0658]

[0659]

[0660]

[0661] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Examples 1 and 2 are shown below.

[0662]

[0663] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 9, Comparative Examples 1 and 2 are shown below.

[0664]

[0665]

[0666]

[0667] <Preparation of Organic EL Device> An organic EL device was prepared as follows.

[0668] Example 1 A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (indium tin oxide) transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and first, compound HT-1 and compound HI-1 were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a film thickness of 10 nm. The content of compound HT-1 in the hole injection layer was 97% by mass, and the content of compound HI-1 was 3% by mass. Next, compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a film thickness of 60 nm. Next, compound EBL-1 was vapor-deposited on the first hole-transporting layer to form a second hole-transporting layer (also referred to as an electron blocking layer) with a thickness of 5 nm. Next, compound h-host-1 as a second host material (fourth compound), compound BH1-1 as a first host material (first compound), compound PD-1 as a sensitizing material (second compound), and compound BD-1 as a fluorescent material (third compound) were co-deposited on the second hole-transporting layer to form an emitting layer with a thickness of 30 nm. In the emitting layer, the content of compound h-host-1 was 43.9% by mass, the content of compound BH1-1 was 43.9% by mass, the content of compound PD-1 was 11.0% by mass, and the content of compound BD-1 was 1.2% by mass. Next, compound HBL-1 was vapor-deposited on the emitting layer to form a hole-blocking layer with a thickness of 5 nm. Next, the compound ET-1 and Liq were co-deposited on the hole blocking layer to form an electron transport layer with a thickness of 30 nm. The content of the compound ET-1 in the electron transport layer was set to 50 mass %, and the content of Liq was set to 50 mass %. Liq is an abbreviation for (8-quinolinolato)lithium. Next, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metal aluminum (Al) was deposited on the electron injection layer to form a metal Al cathode with a thickness of 50 nm. In this manner, the organic EL device according to Example 1 was produced.The device configuration of the organic EL device according to Example 1 is shown in outline as follows: ITO(130) / HT-1:HI-1(10,97%:3%) / HT-1(60) / EBL-1(5) / h-host-1:BH1-1:PD-1:BD-1(30,43.9%:43.9%:11.0%:1.2%) / HBL-1(5) / ET-1:Liq(30,50%:50%) / LiF(1) / Al(50). In the device configuration shown in outline, the numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the figures expressed in percentage (97%:3%) indicate the contents (mass%) of Compound HT-1 and Compound HI-1 in the hole injection layer, the figures expressed in percentage (43.9%:43.9%:11.0%:1.2%) indicate the contents (mass%) of Compound h-host-1, Compound BH1-1, Compound PD-1, and Compound BD-1 in the emitting layer, and the figures expressed in percentage (50%:50%) indicate the contents (mass%) of Compound ET-1 and Liq in the electron transport layer.

[0669] [Examples 2 to 7] The organic EL elements of Examples 2 to 7 were fabricated in the same manner as the organic EL element of Example 1, except that the compound BH1-1 used in forming the light-emitting layer was changed to the compound shown in Table 1. The device configurations of the organic EL elements of Examples 6 and 7 listed in Table 2 were the same as the device configurations of the organic EL elements of Examples 6 and 7 listed in Table 1.

[0670] Comparative Example 1 The organic EL device of Comparative Example 1 was fabricated in the same manner as in Example 1, except that the compound BH1-1 used in the light-emitting layer of Example 1 was changed to a compound shown in Table 1.

[0671] [Examples 8 to 9] The organic EL devices of Examples 8 to 9 were fabricated in the same manner as the organic EL device of Example 1, except that the compound BH1-1 used to form the light-emitting layer was changed to the compound shown in Table 2.

[0672] Comparative Example 2 The organic EL device of Comparative Example 2 was fabricated in the same manner as in Example 1, except that the compound BH1-1 used in the light-emitting layer of Example 1 was changed to a compound shown in Table 2.

[0673] <Evaluation of Organic EL Device> The fabricated organic EL device was evaluated as follows. The evaluation results are shown in Tables 1 and 2.

[0674] (Lifespan (LT95)) The organic EL element thus fabricated was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the luminance reached 95% of the initial luminance (LT95 (unit: hour)), and the time required for the luminance to reach 95% of the initial luminance was measured as the lifespan. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Tables 1 and 2 show the "LT95 (relative value)" (unit: %).

[0675] The LT95 (relative value) of each example (Examples 1 to 7 and Comparative Example 1) was calculated based on the following formula (2X-1): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) x 100

[0676] The LT95 (relative value) of each example (Examples 6 to 9 and Comparative Example 2) was calculated based on the following formula (2X-2): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 2) x 100

[0677]

[0678]

[0679] The organic EL devices of Examples 1 to 7, which contained the compound represented by formula (1) (first compound) as a first host material in the light-emitting layer, had a longer life than the organic EL device of Comparative Example 1, in which the first compound was replaced with compound Ref-1. The organic EL devices of Examples 6 to 9, which contained the compound represented by formula (1) (first compound) as a first host material in the light-emitting layer, had a longer life than the organic EL device of Comparative Example 2, in which the first compound was replaced with compound Ref-2.

[0680] <Synthesis Examples> Synthesis examples of compounds BH1-1 to BH1-11 are shown below.

[0681]

[0682]

[0683]

[0684] Synthesis Example 1: Synthesis of Compound BH1-1 Compound BH1-1 was synthesized according to the following synthesis route.

[0685]

[0686] (Synthesis of Compound BH1-1) Under an argon atmosphere, a reaction vessel was charged with intermediate M1-1 (3.00 g, 8.26 mmol), intermediate M1-2 (3.07 g, 6.88 mmol), tetrakistriphenylphosphine palladium(0) (Pd(PPh ３ ) ４ ) (0.398 g, 0.344 mmol), 2 M aqueous potassium carbonate solution (10 ml), and 1,4-dioxane (70 ml) were added, and the solution in the reactor was heated and stirred at 90°C for 10 hours. After completion of the reaction, water and toluene were added to the reaction solution, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (2.66 g, yield 53%). As a result of mass spectrometry analysis, the white solid was identified as compound BH1-1.

[0687] Synthesis Example 2: Synthesis of Compound BH1-2 Compound BH1-2 was synthesized according to the following synthesis route.

[0688]

[0689] (Synthesis of Compound BH1-2) Under an argon atmosphere, a reaction vessel was charged with intermediate M2-1 (2.50 g, 6.88 mmol), intermediate M1-2 (2.56 g, 5.74 mmol), tetrakistriphenylphosphine palladium(0) (Pd(PPh ３ ) ４ ) (0.331 g, 0.287 mmol), 2 M aqueous potassium carbonate solution (10 ml), and 1,4-dioxane (60 ml) were added, and the solution in the reactor was heated and stirred at 90°C for 9 hours. After completion of the reaction, water and toluene were added to the reaction solution, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (1.96 g, yield 47%). As a result of mass spectrometry analysis, the white solid was identified as compound BH1-2.

[0690] Synthesis Example 3: Synthesis of Compound BH1-3 Compound BH1-3 was synthesized according to the following synthesis route.

[0691]

[0692] (Synthesis of Intermediate M3-2) Under an argon atmosphere, intermediate M3-1 (5.00 g, 12.6 mmol) and tetrahydrofuran (THF) (60 ml) were placed in a reactor, and the reactor was cooled to −50° C. A 1.6 M hexane solution (7.9 ml) of n-butyllithium (BuLi) was added dropwise thereto, and the mixture was stirred at −50° C. for 1 hour. Thereafter, the reactor was cooled to −70° C., and triisopropyl borate (B(Oi-Pr) ３ ) (8.7 ml, 37.7 mmol) was added dropwise and the mixture was stirred at -70°C for 1 hour. The temperature was returned to room temperature and the mixture was stirred for 3 hours, after which 1N hydrochloric acid was added thereto and the mixture was stirred for 30 minutes. After completion of the reaction, water and toluene were added to the reaction solution, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain intermediate M3-2 as a white solid (4.38 g, yield 65%).

[0693]

[0694] (Synthesis of Compound BH1-3) Under an argon atmosphere, a reaction vessel was charged with intermediate M3-2 (3.50 g, 9.64 mmol), intermediate M1-2 (3.58 g, 8.03 mmol), and tetrakistriphenylphosphine palladium(0) (Pd(PPh ３ ) ４ ) (0.464 g, 0.402 mmol), 2 M aqueous potassium carbonate solution (15 ml), and 1,4-dioxane (80 ml) were added, and the solution in the reactor was heated and stirred at 90°C for 8 hours. After completion of the reaction, water and toluene were added to the reaction solution, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (3.57 g, yield 61%). As a result of mass spectrometry analysis, the white solid was identified as compound BH1-3.

[0695] Synthesis Example 4: Synthesis of compound BH1-4 Compound BH1-4 was synthesized according to the following synthesis route.

[0696]

[0697] (Synthesis of Intermediate M4-2) Under an argon atmosphere, a reaction vessel was charged with Intermediate M4-1 (10.0 g, 39.2 mmol), 1-bromo-2-fluorobenzene (6.85 g, 23.9 mmol), and cesium carbonate (Cs ２ CO ３ ) (25.5 g, 78.3 mmol) and N,N-dimethylformamide (DMF) (130 ml) were added, and the solution in the reactor was heated and stirred at 150°C for 22 hours. After completion of the reaction, the reaction solution was filtered to obtain a crude product, which was washed with methanol and water. The washed crude product was purified by column chromatography to obtain intermediate M4-2 as a white solid (23.5 g, yield 92%).

[0698]

[0699] (Synthesis of Intermediate M4-3) Under an argon atmosphere, intermediate M4-2 (10.0 g, 24.4 mmol) and tetrahydrofuran (THF) (120 ml) were placed in a reactor, and the reactor was cooled to −50° C. A 1.6 M hexane solution (15 ml) of n-butyllithium (BuLi) was added dropwise thereto, and the mixture was stirred at −50° C. for 1 hour. Thereafter, the reactor was cooled to −70° C., and triisopropyl borate (B(Oi-Pr) ３ ) (17 ml, 73.1 mmol) was added dropwise and the mixture was stirred at -70°C for 1 hour. The temperature was returned to room temperature and the mixture was stirred for 3 hours, after which 1N hydrochloric acid was added and the mixture was stirred for 30 minutes. After the reaction was completed, water and toluene were added to the reaction solution, the organic layer was extracted, and the solvent was distilled off to obtain a crude product which was purified by column chromatography to obtain intermediate M4-3 as a white solid (8.23 g, yield 63%).

[0700]

[0701] (Synthesis of Compound BH1-4) Under an argon atmosphere, a reaction vessel was charged with intermediate M4-3 (3.20 g, 8.53 mmol), intermediate M4-4 (3.28 g, 7.11 mmol), tetrakistriphenylphosphine palladium(0) (Pd(PPh ３ ) ４) (0.411 g, 0.355 mmol), 2 M aqueous potassium carbonate solution (12 ml), and 1,4-dioxane (70 ml) were added, and the solution in the reactor was heated and stirred at 90°C for 9 hours. After completion of the reaction, water and toluene were added to the reaction solution, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (2.59 g, yield 50%). As a result of mass spectrometry analysis, the white solid was identified as compound BH1-4.

[0702] Synthesis Example 5: Synthesis of Compound BH1-5 Compound BH1-5 was synthesized according to the following synthesis route.

[0703]

[0704] (Synthesis of Intermediate M5-2) Under an argon atmosphere, a reaction vessel was charged with Intermediate M5-1 (8.00 g, 31.3 mmol), 1-bromo-2-fluorobenzene (5.48 g, 31.3 mmol), and cesium carbonate (Cs ２ CO ３ ) (20.4 g, 62.7 mmol) and N,N-dimethylformamide (DMF) (100 ml) were added, and the solution in the reactor was heated and stirred at 150°C for 24 hours. After completion of the reaction, the reaction solution was filtered to obtain a crude product, which was washed with methanol and water. The washed crude product was purified by column chromatography to obtain intermediate M5-2 as a white solid (18.0 g, yield 88%).

[0705]

[0706] (Synthesis of Intermediate M5-3) Under an argon atmosphere, intermediate M5-2 (10.0 g, 24.4 mmol) and tetrahydrofuran (THF) (120 ml) were placed in a reactor, and the reactor was cooled to −50° C. A 1.6 M hexane solution (15 ml) of n-butyllithium (BuLi) was added dropwise thereto, and the mixture was stirred at −50° C. for 1 hour. Thereafter, the reactor was cooled to −70° C., and triisopropyl borate (B(Oi-Pr) ３) (17 ml, 73.1 mmol) was added dropwise and the mixture was stirred at -70°C for 1 hour. The temperature was returned to room temperature and the mixture was stirred for 3 hours, after which 1N hydrochloric acid was added thereto and the mixture was stirred for 30 minutes. After completion of the reaction, water and toluene were added to the reaction solution, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain intermediate M5-3 as a white solid (8.88 g, yield 68%).

[0707]

[0708] (Synthesis of Compound BH1-5) Under an argon atmosphere, a reaction vessel was charged with intermediate M5-3 (2.75 g, 7.33 mmol), intermediate M4-4 (2.82 g, 6.11 mmol), tetrakistriphenylphosphine palladium(0) (Pd(PPh ３ ) ４ ) (0.353 g, 0.305 mmol), 2 M aqueous potassium carbonate solution (10 ml), and 1,4-dioxane (60 ml) were added, and the solution in the reactor was heated and stirred at 90°C for 9 hours. After completion of the reaction, water and toluene were added to the reaction solution, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (2.80 g, yield 63%). As a result of mass spectrometry analysis, the white solid was identified as compound BH1-5.

[0709] Synthesis Example 6: Synthesis of compound BH1-6 Compound BH1-6 was synthesized according to the following synthesis route.

[0710]

[0711] (Synthesis of Compound BH1-6) Under an argon atmosphere, a reaction vessel was charged with Intermediate M1-1 (3.00 g, 8.26 mmol), Intermediate M6-1 (3.06 g, 6.88 mmol), and tetrakistriphenylphosphine palladium(0) (Pd(PPh ３ ) ４) (0.398 g, 0.344 mmol), 2 M aqueous potassium carbonate solution (12 ml), and 1,4-dioxane (70 ml) were added, and the solution in the reactor was heated and stirred at 90°C for 12 hours. After completion of the reaction, water and toluene were added to the reaction solution, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (2.41 g, yield 48%). As a result of mass spectrometry analysis, the white solid was identified as compound BH1-6.

[0712] Synthesis Example 7 Synthesis of Compound BH1-7 Compound BH1-7 was synthesized according to the following synthesis route.

[0713]

[0714] (Synthesis of Compound BH1-7) Compound BH1-6 (2.63 g, 3.61 mmol) and ortho-dichlorobenzene (o-DCB) (30 ml) were placed in a flask and completely dissolved with stirring at room temperature. Benzene-d6 (15 ml) was then added to the flask and stirred at 10°C for 5 minutes. Trifluoromethanesulfonic acid (TfOH) (0.53 ml, 5.93 mmol) was then added, and the mixture was stirred at 10°C for 2 hours. 20 ml of heavy water was then added, and the mixture was stirred for an additional 15 minutes. The aqueous layer was then removed, and the remaining organic layer was concentrated. The resulting solid was purified by silica gel column chromatography to obtain a white solid (1.10 g, yield 40%). Mass spectrometry analysis identified the white solid as Compound BH1-7.

[0715] Synthesis Example 8: Synthesis of compound BH1-8 Compound BH1-8 was synthesized according to the following synthesis route.

[0716]

[0717] (Synthesis of Intermediate M8-2) Under an argon atmosphere, intermediate M8-1 (5.00 g, 12.6 mmol) and tetrahydrofuran (THF) (60 ml) were placed in a reactor, and the reactor was cooled to −50° C. A 1.6 M hexane solution (7.9 ml) of n-butyllithium (BuLi) was added dropwise thereto, and the mixture was st...

Claims

1. A compound represented by the following formula (1): (In the formula (1), Z １ , Z ２ , and Z ３ are each independently a nitrogen atom, or C(R ３１ ), where Z １ ~Z ３ At least two of R are nitrogen atoms; １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , and R １８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ２１ , R ２２ , R ２３ , R ２４ , R ２５ , R ２６ , R ２７ , and R ２８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３１ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ ), a group represented by —B(OR ９３８ ) (OR ９３９ a group represented by —O—S(═O) ２ (R ９４０ 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, provided that at least one condition selected from the group consisting of the following conditions (i), (ii), and (iii) is satisfied: Condition (i): R １ ~R ８ Condition (ii): At least one of R １１ ~R １８ Condition (iii): At least one of R ２１ ~R ２８ At least one of the four Ax's is a substituted or unsubstituted phenyl group. p is 4, and at least one pair of adjacent two or more Ax's are not bonded to each other, and each Ax is independently a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -C(R ９０１Ｂ ) (R ９０２Ｂ ) (R ９０３Ｂ a group represented by —Si(R ９０１Ａ ) (R ９０２Ａ ) (R ９０３Ａ 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, ９０１ ~R ９０７ , R ８０１ ~R ８０２ , and R ９３１ ~R ９４０ are each independently 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１Ａ , R ９０２Ａ , R ９０３Ａ , R ９０１Ｂ , R ９０２Ｂ , and R ９０３Ｂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, R ９３１ If there are multiple R ９３１ are the same or different from each other, R ９３２ If there are multiple R ９３２ are the same or different from each other, R ９３３ If there are multiple R ９３３ are the same or different from each other, R ９３４ If there are multiple R ９３４ are the same or different from each other, R ９３５ If there are multiple R ９３５ are the same or different from each other, R ９３６ If there are multiple R ９３６ are the same or different from each other, R ９３７ If there are multiple R ９３７ are the same or different from each other, R ９３８ If there are multiple R ９３８ are the same or different from each other, R ９３９ If there are multiple R ９３９ are the same or different from each other, R ９４０ If there are multiple R ９４０ are the same or different from each other, R ９０１Ａ If there are multiple R ９０１Ａ are the same or different from each other, R ９０２Ａ If there are multiple R ９０２Ａ are the same or different from each other, R ９０３Ａ If there are multiple R ９０３Ａ are the same or different from each other, R ９０１Ｂ If there are multiple R ９０１Ｂ are the same or different from each other, R ９０２Ｂ If there are multiple R ９０２Ｂ are the same or different from each other, R ９０３Ｂ If there are multiple R ９０３Ｂ are the same or different from each other.) 2. The compound according to claim 1, wherein the compound represented by formula (1) satisfies the condition (i).

3. In the compound represented by the formula (1), R １ ~R ８ The compound according to claim 1 or claim 2, wherein any pair of adjacent two or more of 4. In the compound represented by formula (1), R １１ ~R １８ The compound according to any one of claims 1 to 3, wherein any pair of adjacent groups of:

5. In the compound represented by formula (1), R ２１ ~R ２８ The compound according to any one of claims 1 to 4, wherein any pair of adjacent groups of:

6. In the compound represented by the formula (1), R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ , and R ３１ The compound according to any one of claims 1 to 5, wherein at least one of the following is a deuterium atom:

7. The compound according to any one of claims 1 to 6, wherein in the compound represented by formula (1), all of the hydrogen atoms possessed by the substituted or unsubstituted phenyl group under at least one of the conditions (i), (ii), and (iii) are deuterium atoms.

8. In the compound represented by the formula (1), Z １ ~Z ３ Two of the nitrogen atoms are nitrogen atoms, and Z １ ~Z ３ One of them is C(R ３１ 8. The compound of claim 1, wherein 9. In the compound represented by the formula (1), Z １ is a nitrogen atom, and Z ２ and Z ３ Any of Z is a nitrogen atom, and Z is not a nitrogen atom. ２ and Z ３ is C(R ３１ ) and R ３１ The compound according to any one of claims 1 to 8, wherein is a hydrogen atom.

10. In the compound represented by formula (1), Z １ ~Z ３ The compound of any one of claims 1 to 7, wherein all of are nitrogen atoms.

11. The compound represented by the formula (1) satisfies the condition (i) and R is not a substituted or unsubstituted phenyl group. １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ The compound according to any one of claims 1 to 10, wherein is a hydrogen atom.

12. The compound represented by the formula (1) satisfies the condition (i), and R １ ~R ８ At least one of R is a substituted or unsubstituted phenyl group, １ ~R ８ The compound of any one of claims 1 to 11, wherein all of the remainder are deuterium atoms.

13. The compound represented by the formula (1) does not satisfy the condition (ii), and R １１ ~R １８ The compound according to any one of claims 1 to 12, wherein all are deuterium atoms.

14. The compound represented by the formula (1) does not satisfy the condition (iii), and R ２１ ~R ２８ The compound according to any one of claims 1 to 12, wherein all are deuterium atoms.

15. The compound represented by the formula (1) does not satisfy the conditions (ii) and (iii), and R １１ ~R １８ and R ２１ ~R ２８ The compound according to any one of claims 1 to 12, wherein all are deuterium atoms.

16. In the compound represented by formula (1), each of the four Ax independently represents a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or —Si(R ９０１Ａ ) (R ９０２Ａ ) (R ９０３Ａ 16. The compound according to claim 1, wherein the aryl group is a group represented by the formula:

17. The compound according to any one of claims 1 to 16, wherein in the compound represented by formula (1), four Ax are hydrogen atoms.

18. In the compound represented by formula (1), at least one of the four Ax is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R ９０１Ａ ) (R ９０２Ａ ) (R ９０３Ａ 17. The compound according to claim 1, wherein the aryl group is a group represented by the formula:

19. The compound represented by the formula (1) satisfies the condition (i), and R １ ~R ８ The compound according to any one of claims 1 to 18, wherein at least one of 20. The compound according to any one of claims 1 to 19, wherein the compound represented by formula (1) is a compound represented by the following formula (1A): (In the formula (1A), Z １ ~Z ３ , and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ are Z in the formula (1), respectively. １ ~Z ３ , and R １ ~R ８ , R １１ ~R １８ , and R ２１ ~R ２８ is synonymous with A １ , A ２ , A ３ and A ４ each independently has the same meaning as Ax in formula (1).

21. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 20.

22. An organic electroluminescence device comprising: a cathode; an anode; and an emitting unit disposed between the cathode and the anode, wherein the emitting unit contains the compound according to any one of claims 1 to 20 as a first compound.

23. The organic electroluminescence device according to claim 22, wherein the light-emitting unit has one or more light-emitting layers, and at least one layer of the one or more light-emitting layers contains the first compound.

24. The organic electroluminescence device according to claim 23, wherein at least one layer of the one or more light-emitting layers contains the first compound as a first host material.

25. The organic electroluminescence device according to claim 24, wherein at least one layer of the one or more light-emitting layers contains the first host material and a phosphorescent metal complex or a fluorescent material.

26. The organic electroluminescence device according to claim 24, wherein at least one layer of the one or more light-emitting layers contains the first host material, a sensitizing material, and a fluorescent material.

27. The organic electroluminescence device according to claim 26, wherein the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescent compounds.

28. The organic electroluminescence device according to any one of claims 23 to 27, wherein at least one of the one or more light-emitting layers further contains a fourth compound as a second host material, and the first compound and the fourth compound are different from each other.

29. The organic electroluminescence device according to any one of claims 23 to 28, further comprising a hole transport layer between the anode and the light-emitting layer closest to the anode among the one or more light-emitting layers.

30. An organic electroluminescence device according to any one of claims 23 to 29, further comprising an electron transport layer between the cathode and the light-emitting layer closest to the cathode among the one or more light-emitting layers.

31. An electronic device equipped with the organic electroluminescence element according to any one of claims 22 to 30.

Images